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o o Copyright. 1955 and 1958, by Union Carbide Corporation. CONFIDENTIAL: Of l-astrict Court 91-114 5 04925& SL Organic Chlorine Compounds.............. Tables: Physical Properties........... Solubility Data................... Kthylene Dichloride........................... Chlorasol Fumigant and Solvent . . . Propylene Dichloride.......................... Trichloretliane...................................... Butyl Chloride...................................... 2-Ethylhexyl Chloride...................... Dichlorethyl Ether............................... Dichlorisopropyl Ether....................... Triglycol Dichloride............................. Ethylene Chlorhydrin........................... Epichlorhydrin..................................... Advantages of Chlorinated Solvents. Handling and Storage of Chlorinated Compounds Physiological Properties.............. Shipping Data............................... Specifications and Test Methods. Constant Boiling Mixtures........... Physical Property Charts............. Bibliography.................................. Other Chemicals Produced by Carbide . Sales Offices and Telephone Numbers. . Outside Bad UNION CARBIDE CHEMICALS COMPANY Division of UNION CARBIDE Corporation 30 East 42nd Street, New York 17, N, Y. CONFIDENTIAL: Subject to Protective Order of 14th Judicial District Court No. 91-1145 049257 SE Organic CHLORINE COMPOUNDS This equipment is used to process organic chlorine compounds and their derivatives at Carbide's South Charleston, West Virginia plant. CONFIDENTIAL Subject to Protective Order of 14th Judicial District Court 2 No. 91-1145 SL 49258 M Most chlorine compounds are stable, non-flammable liquids. Thev find many applications as solvents, extractants, intermediates, and fumigants. Organic chlorine compounds generally have a powerful solvent ac tion for oils, fats, waxes, greases, gums, and resins but are insoluble in water. They are good non-polar solvents for many hydrocarbons, alkaloids, and synthetic rubber and only partially dissolve highly polar derivatives such as sugars, proteins, inorganic acids, and glycerol. The addition of a small amount of ethanol to many chlorinated hydrocarbons produces an active solvent mixture for cellulose nitrate. The lower boiling chlorinated solvents are useful as extractants. Their narrow boiling range and low boiling points permit their easv recoverv from the extracted materials. Organic chlorine compounds are used in the synthesis of pharma ceuticals. insecticides, synthetic rubbers, and resins. Some chlorine com pounds are effective fumigants. Carbide offers 11 organic compounds in commercial quantities. This book contains information on their uses, physical and physiological prop erties, shipping regulations, handling and storage, and specifications and test methods. This information will be of value to purchasing agents, manage ment personnel, and research chemists. Research groups will particularly find this book of interest in improving standard products and developing better ones to expand present markets or open new ones. Samples are avail able for laboratory investigations. It is not possible to mention in this book all the applications of these organic chlorine compounds. Technical Representatives located in 28 prin cipal industrial cities throughout the country have the necessary knowledge and experience to assist you with the development of these chemicals. They can also aid purchasing agents and production engineers in dav-to-day prob lems of shipping and storing these and other organic chemicals. Routine check, as shown here at an organic chlorine production still, helps maintain consistent standards of high quality. CONF IDENTIAL: Subject to Protective Order of 14th Cubic ial District Court No. 91-1145 3 PHYSICAL PROPERTIES Ethylene Dichloride Propylene Dichloride 1,1,2-Trichlorethane Molecular Weight 98.97 112.99 133.42 Specific Gravity. 20 20 C. 1.2554 1.1583 1.4432 ^ *P- >rAt. 0.00146 0.00131 0.00154 Boiling Point, C. 760 mm. 50 mm. 10 mm. 83.5 96.3 113.7 15 25 41 -13 -5 11 Butyl Chloride 2-Ethylhexyl Chloride 92.57 148.67 0.8875 0.8833 0.00111 0.00086 78.6 173.0 10 89 -18 55 Dichlorethyl Ether Dichlorisopropyl Ether Triglyeol Dichloride 143.02 171.07 187.07 1.2220 1,1135 1.1974 0.00118 0.00107 0.00110 179.2 187.0 240.9 96 104 151 64 68 114 Ethylene Chlorhydrin Epichlorhydrin 80.52 92.53 1.2045 1.1761 0.00107 0.00120 128.7 115.2 60 45 32 16 S LUBILITT DATA Ethylene Dichloride Propylene Dichloride 1,1,2-Trichlorethane Butyl Chloride 2-Ethylhexyl Chloride Dichlorethyl Ether Dichlorisopropyl Ether Triglycol Dichloride BAKELITE Vinyl Resin* AYAF VYHH SS S5 Cellulose Acetate SA 1 SS S SS 11 E 1 1 SS SA S SW 1 S SW PSA NitrocellU' lose SA SA E 1 1 SA 1 SA Subject'C?"FlDEXTXAL: f 14th Judicial0^1;* ,^er N. uli,Lrict 91-1145' C~ ourt 4 SL 049260 ETHYLENE DICHLORIDE (Ethylene Chloride ; 1,2-Dichlorethane) CICH2CH2CI Ethylene dichloride's excellent solvent power and resistance to hy drolysis make it useful as an extractant for oils rfnd fats. Vegetable oils are effectively extracted from expeller cakes through the use of ethylene dichloride. Ethylene dichloride is used to concentrate vitamins A and D from cod and shark liver oils. In this way, odorless and tasteless products are prepared. Its boiling point is high enough to permit the use of low-pressure equipment. Ethylene dichloride is also useful in the vapor-phase degreasing of metal articles. An excellent solvent for all standard low-viscosity types of cellulose acetate (up to 61 per cent combined acetic acid) is a 9 to 1 mixture of eth ylene dichloride and ethanol. Ethylene dichloride is also a valuable solvent in compounding polysulfide rubbers and Buna N synthetic rubbers for cements and coatings. Ethylene dichloride is a useful scouring and spotting agent for the removal of tar, paint, and brand marks from wool. When incorporated into soaps and scouring compounds, it assists in the removal of grease. Wettingout and penetrating compounds can also incorporate ethylene dichloride. Its solvent action on the natural waxes assists in the degumming of silk and cotton. Ethylene dichloride lends itself readily to a number of valuable syn theses, as both chlorine atoms can be replaced by other groups. Such an example is its condensation with sodium cyanide to form succinonitrile. followed by hydrolysis with aqueous hydrochloric acid to produce succinic acid. With polysulfides, oil and gasoline-resistant rubber-like materials are formed. Ethylene polysulfide, a useful polymer lubricant, is prepared from ethylene dichloride and sodium polysulfide.1 Vinyl chloride is produced from ethylene dichloride and aqueous caustic at an elevated temperature and pressure.'1 The condensation products of dioleyl- and dilauryldiethylene triamine with ethylene dichloride are useful antifoaming agents for steam boilers and generators.3 Literature Cited 1 B. A. Perkins (to Rockwell Manufacturing CoJ U.S. Pat ent 2,474.859 (July 5, 1949) = R. J. Koll (to Diamond Alkali Co.), U.S. Patent 2.539.307 (January 23, 1951) 3 P. G. Bird, A. L. Jacoby (to National Aluminate Corp.i, U.S. Patent 2,580,880 (January 1, 1952) CONFIDENTIAL: Subject to Protective Order of 14th Judicial District Court No. 91-1145 SL 049261 "CHLORASOL" FUMIGANT AND SOLVENT (Solvent EDM) Chlorasol fumigant and solvent is a mixture containing 75 per cent by volume ethylene dichloride and 25 per cent by volume carbon tetrachlor ide. It is not flammable under conditions of ordinary use. Chlorasol solvent readily dissolves oils, waxes, gums, and tars, and is an active solvent component in industrial cleaning compounds, tvpe clean ers. spotting solvents, and similar specialty products. It is also used in clean ing textiles and in removing oils and greases from machinery. Chlorasol fumigant is an effective fumigant for grain, and clothes moths; grain weevils; grain, flour, and carpet beetles; the rice weevil; and book lice --- as well as their larvae and eggs. Its vapors penetrate stored grain, rolled rugs, upholstered furniture, cartons, sacks, and stacked mate rial. It is non-flammable under ordinary conditions of use and evaporates quickly at a room temperature of 70F. or higher. The rate of evaporation Fumigating grain stored in the hold of a grain transport. Chlo rasol fumigant is effective in pre venting grain infestation during storage in grain transports, bins, and silos. m _ confidential Subject to I'rofpnHof 14 th Jlo'-:- - ,., Order.- -j-.t Court 7 SL 049262 and the depth of penetration increase as the temperature increases. Chlorasol fumigant is fast acting and is quickly and easily removed by adequate ventilation. Chlorasol fumigant can be applied either directly to grain in the storage bin, grain car, or silo or by mixing it with the stream of grain coming into the terminal elevator. When fumigating grain, the storage bins and elevators must be reasonably airtight for the fumigant to be completely effective. Individual sections of mill machinery can be fumigated by spray ing or pouring the liquid onto the grain as it is fed into the machine. In this way, the sections likely to be infested can be individually treated. When used in accordance with directions, residues df Chlorasol fumigant on treated grain are exempt from the tolerance requirements of the Federal Food, Drug, and Cosmetic Act. In buildings and warehouses, Chlorasol fumigant is particularly suited for the fumigation of various commodities that have become infested while in storage. It may be used simply yet effectively by pouring the liquid into shallow pans or travs near the ceiling of the room to be fumigated. In more permanent installations, the liquid can be piped into the trays from storage tanks. Furniture can be satisfactorily fumigated with Chlorasol fumigant in an atmospheric vault. Fabrics and furs are fumigated in airtight vaults and when properly used, Chlorasol fumigant has no effect on the hair, pelts, dyes, buttons, or other parts of the garment. CHLORASOL fumigant is one of the few effective fumigants that can be safely used on seeds. Expo sures up to 72 hours have no effect upon seed germination. PROPYLENE DICHLORIDE (1,2-Dichloropropane) CH3CHCICH2CI Propylene dichloride is used as an extraction solvent where its high boiling point offers special processing advantages. Its stability, ease of recovery, and solvent characteristics make it valuable for the preparation of highly concentrated lactic acid. Propylene dichloride is used in the preparation of cleaning and scouring compounds, spot-removing agents, and in the pyrolytic production of chlorhydrocarbons,1 It is also an inter mediate in the manufacture of alcohols, amines, nitriles, and acids. Literature Cited 1 E. K. Morris (to Dow Chemical Co.), U.S. Patent 2,588.867 (March 11. 1952) - CONFIDENTIAL: Subject to Protective Order 8 of 14th Judicial District Court !3c. 0/*92b3 Many of the organic chloride compounds such as propylene dichloride are used in specialty dry cleaning formulations. Literature Cited 1J. L. Amos (to Dow Chemical CoJ, U.S. Patent 2,610.214 (September 9, 1952) m 1,1,2-TRICHLORETHANE (1,1,2-Trichloroethane ) CICH2CHCI2 Trichlorethane's excellent solvent properties make it a valuable component of spotting or cleaning fluids. It is also a suitable freezing-point depressant in fire extinguisher fluids based on carbon tetrachloride. Vinvlidene chloride (CHj = CCI2), which can be polymerized to lorm a valuable group of resins, is prepared bv splitting hydrogen chloride from trichlorethane.1 CONFIDENTIAL: Subject to Protective Order of 14th Judicial District Court No 9 SL 049264 Butyl chloride is an effective deworming agent in veterinary medicine. BUTYL CHLORIDE (l-Chlorobutane) CH3CH2CH2CH2CI 2-ETHYLHEXYL CHLORIDE CH3CH2CH2CH2CH(C3H5)CH2CI Both butyl chloride and 2-ethvlhexvl chloride are used as alkylat ing agents for the modification of phenols, amines, cellulose, starch, and other materials. Such modification usually leads to derivatives with greater oil and organic solvent solubility and lower water solubility than the parent unalkvlated compound. These derivatives are of value in extraction processes and as petroleum additives and plasticizers. Butvl chloride is an effective anthelmintic (deworming agent) in veterinary medicine. It is used in the manufacture of tin stabilizers for vinyl resins. CONFIDENTIAL: Subject to Protective Order of 14th Judicial District Court 1: o. 91-.U45 10 SL 049265 2-Ethvlhexyl chloride is used as an instrument fluid because of its clarity, low viscosity, high boiling point, and low vapor pressure at normal temperatures. It is particularly useful in aircraft instruments because of its extremely low freezing point (--135C.) and its stability over a wide tem perature range. 2-Ethylhexvl chloride is also an intermediate for various surface active agents of the alkyl-aryl sulfonic acid type. Literature Cited 1 H. A. Bruson (to Rohm and Haas Co.). U.S. Patent 2,098.203 (November 2. 1937) 2 H. A. Bruson I to Rohm and Haas Co,), U.S. Patent 2,115,192 < April 26. 1938) DICHLORETHYL ETHER [2,2'-Dichloroethyl Ether, Di( 2-Chloroethyl) Ether] CICHsCHaOCHaCH^CI Dichlorethvl ether is a colorless liquid with a chloroform-like odor. It is extremely resistant to hydrolysis. This chlorinated ether is a particularly good solvent for fats, waxes, or greases. The solvent action of dichlorethyl ether makes it a useful scouring agent for textiles. When used either in the scouring bath or as a pre-spotter, dichlorethyl ether aids in removing paint and tar brand marks from raw wool, and oil and grease spots from cloth. Since the solvent is retained by the goods throughout the process, hand spotting in many cases is eliminated. Dichlorethyl ether is an intermediate in the manufacture of alkyl aryl ether sulfate or sulfonate-type (R^^OCsH^CjHiSOs) anionic sur face active agents, us The advantage of the use of this chlorinated ether is its ability to introduce only two ethylene oxide linkages into the molecule and thereby controlling the hydrophobic-hydrophilic balance of the resulting detergent. These surface active agents are good emulsifiers for oils, fats, and greases and have excellent detergent, lathering, and rinsing qualities. They are also good emulsifiers for cosmetic preparations and their excellent deter gent and lathering properties make them well suited for shampoo and cleans ing cream bases. Metal cleaning operations are another important application for surface active agents of this type. Dichlorethyl ether is a solvent for the separation of butadiene from butylene by extractive distillation. It is also used for the recovery of ethylene :oi- FlDFNTIftL: Subject to Protective Order of 14th Judi ial District Court No 91-1145 49^6 0 Lotions and cleansing creams are formulated from alkyl aryl ether sulfonates derived from dichlorethyl ether. Chlorex solvent is used in a process for the purification of naphthenic crude oils. oxide after the oxidation of ethylene.' A mixture of nitrobenzene and di chlorethyl ether makes an effective solvent in the fractionation of waxcontaining mixtures.4 Dichlorethyl ether, sold as Chlorex solvent, is used as a selective solvent in the production of high-grade lubricants from Mid-Continent and other naphthenic crude oils. The abilitv of dichlorethyl ether to scavenge lead deposits in en gines makes it an important component of anti-knock compounds.5 This chlorinated ether is used in the syntheses of morpholine and N-substituted morpholine derivatives. It is an intermediate in the produc tion of divinyl ether, a basic anesthetic. Dichlorethyl ether is also a raw material in the svntheses of resins and plasticizers, textile chemicals, phar maceuticals, insecticides, rubber chemicals, and lubricating-oil additives. a C. J. Thomas I to Phillips Petro leum Co.). Ll.S. Patent 2,622.088 (December 16, 1952) J E. W. Clarke (to Atlantic Re fining Co.), Ll.S. Patent 2,604,432 (July 22. 1952) '> G. Calingaert (to Ethyl Corp.). U.S. Patent 2,496,983 (Febru ary 7, 1950) DICHLORISOPROPYL ETHER (2,2'-Dichlorodiisopropyl Ether) CICH2(CH3)CHOCH(CH3)CH3CI The properties of dichlorisopropyl ether are very similar to those of dichlorethyl ether. However, this chlorinated isopropyl ether is less sol- cor;? j : jat.: Subioct to loetective Order of 14th Judicial District Court No. 91-1145 $ 12 04 9 Literature Cited 1 P. P. Regna, I. A. Solomons (to Chas. Pfizer & Co. Inc.), U.S. Patent 2,556,375 (June 12. 1951) uble in water, and has a higher boiling point and a lower volatility than dichlorethyl ether. It is miscible with petroleum, vegetable or animal oils, and many organic liquids. It is an excellent extractant for butadiene, fats, vitamins, waxes, and greases. In textile processes where high temperatures are encountered, dichlorisopropyl ether assists the action of soap solutions without causing excessive loss by vaporization from the hot solutions. The excellent solvent action of dichlorisopropyl ether is advantageous in paint and varnish re movers, spotting agents, and cleaning solutions. Dichlorisopropyl ether is employed as a solubility depressant in the extraction of the antibiotic bac itracin from fermentation broths.1 It offers numerous possibilities as an inter mediate in the manufacture of dyes, resins, and pharmaceuticals, - Products made fronvdichlorisopropyl ether are generally less soluble in water and more soluble in oil than those made from dichlorethyl ether, a difference caused by the two additional methyl groups in its molecule. Literature Cited L. Coes, Jr, (to Norton Co.), U.S. Patent 2,456,921 (Decem ber 21, 1948) TRIGLYCOL DICHLORIDE [2 (2-Chloroethoxy) Ethyl 2'-Chloroethyl Ether, Triethylene Glycol Dichloride] CICH2CH2OCH2CH2OCH2CH2CI Triglycol dichloride is a water-insoluble liquid with a high boiling point. Its solvent properties are similar to those of dichlorethyl ether. Triglycol dichloride is a useful solvent and extractant because of its high solvent power for oils and hydrocarbons. In chemical reactions, the chlorine atoms of triglycol dichloride can be replaced by other groups to form a number of compounds such as ethers, esters, thiols, and N-substituted amines and amides. Compounds of this type are useful intermediates for the manufacture of dyes, resins, detergents, and insecticides. Triglycol dichloride is of particular interest in the manufacture of the alkyl aryl ether sulfonate type-detergents (R O OC iH OC 2H 4OC jH <S0 j) , similar to those described on page 11. Triglycol dichloride is used as a cross-linking and hardening agent for aromatic amine-formaldehyde resins used in bonding abrasives to grind ing wheels.1 CONFIDENTIAL: Subject: to Protective Order of 14th Judicial District Court No. 91-1145 SL 049268 13 f ETHYLENE CHLORHYDRIN (2-Chloroethanol) CICH2CH2OH The principal use of ethylene chlorhydrin is for the introduction of the hydroxyethyl group (-CH2CH2OH) into other organic compounds. Resulting derivatives boil about 100C. higher tljan the corresponding ethyl compounds and are more soluble in water. Ethylene chlorhydrin reacts with the salts of organic acids to form glycol esters; with sodium cyanide, it yields ethylene cyanohydrin which can be dehydrated to acrylonitrile. Ethyl ene cyanohydrin can also be hydrolyzed to ieto-hydroxy propionic acid which in turn can be oxidized to malonic acid or dehydrated to acrylic acid. Eth ylene chlorhydrin reacted with brombenzene, by means of the Grignard reaction, produces phenvlethanol (synthetic oil of rose). Ethylene chlorhvdrin is also used in the synthesis of choline (2hydroxyethyl trimethylammonium hydroxide) a member of the Vitamin B group, which is generallv considered to be an essential ingredient in chicken feed to aid in the production of eggs. The reaction of ethylene chlorhydrin and thiophenol produces phenyl vinyl sulfone.1 Sodium terephthalate and ethylene chlorhydrin can be refluxed with sodium iodide and heated in a stream of hydrogen to produce polyesters.2 The isolation of styrene may be accomplished by azeotropic distillation with ethylene chlorhydrin.3 Literature Cited 1 E. F. Landau, E. P. Irany (to Celanese Corp. of America). U.S. Patent 2.554,576 (May 29. 1951) ! J, G. Napier < to Celanese Corp. of America), U.S. Patent 2,551,732 (May 8, 1951) 3K. H. Engel (to Allied Chemi cal and Dye Corp.), U.S. Pat ent 2,465.717 (March 29, 1949) Ethylene chlorhydrin is an inter mediate for choline, a componen of the vitamin B complex whicl is essential to the liver functiot and good egg production. CONFIDENTIAL: Sub j: -t to Protective Order of 14th 14 District Court Wo* 91`ii45 SL 049269 Carbide's Research and Development Center at South Charleston, West Virginia--the birthplace of many new chemicals--was first completed in 1949. A new Development and Engineering Center is being built adjacent to present extensive research facilities. ADVANTAGES OF CHLORINATED SOLVENTS Non-Flammability One of the chief values of chlorinated solvents is their low order of flammability. Their fire hazard is small as shown by these comparative ratings of the Underwriters' Laboratories Standard of Classification: Triehlorethane................. Kerosene (100F. Flash) Ethylene Dichloride. . . . Ethanol............................. Gasoline.......................... Ethyl Ether....................... 3 30 to 40 60 to 70 60 to 70 90 to 100 100 Non-Flammable at Ordinary Temperatures Moderately Flammable Moderately Flammable Moderately Flammable Flammable Flammable Ethylene dichloride and propylene dichloride will burn, but only with difficulty. A much greater concentration is required in the air to form an explosive mixture with them than with other solvents: Benzene.................. Gasoline................. Ethyl Ether.............. Ethylene Dichloride Explosive Limit 1.41% in air, by volume 1.5% in air, by volume 1.71% in air, by volume 16.2% in air, by volume CONFIDENTIAL: Subject to Protective Order of 14th Judicial District Court No. 91-1145 SL 049272 % Epichlorhydrin is an inter mediate in the manufacture of tough, durable epoxy resin castings and embedding materials. (3-Chloro-l,2-Propylene Oxide, 1 -Chloro-2,3-Epoxypropane) CH2CHCH2CI \/ o Epichlorhydrin's reactive chlorine and epoxide groups and its com plete miscibility with ethers, alcohols, acetone, benzene, acetates, and carbon-tetrachloride make it a useful raw material for a wide variety of syntheses. The epoxide group combines exothermically with the active hy drogen atoms in many alcohols, phenols, carboxylic acids, amines, and mercaptans. The chlorine atom reacts with amines, amides, acid salts, and alkali metal phenolates and alcoholates. Epichlorhydrin is a primary raw material in the manufacture of epoxy resins -- important materials for adhesives, surface coatings, resinous castings for tools and dies and for "potting" electrical components. In the 0* Of 14th Judici,a,, rr,*.:r*\^v Order No, 9j.-i7^!r'LC^ Cdijft 15 o manufacture of these epoxy resins, epichlorhydrin is condensed with di- hydric phenols1'5 or phenolic resins* to yield materials ranging from liquids to solids depending on the ratios of epichlorhydrin to the phenol component. The resins may then be converted by amine* or acid curing agents to strong, tough, durable, and solvent and moisture resistant solids. Condensates of epichlorhydrin with polyethylene amines such as diethylene triamine and tetraethylene pentamine also yield resinous mate rials. These are useful as ion exchange resins,4 resins for improving the wet strength of paper,* and resins for promoting the adhesion of lacquers to cellulose films.* , Epichlorhydrin is an intermediate in the manufacture of an anti- spasmodic7 and other pharmaceuticals, detergents and wetting agents, 8*10 and textile softeners. It is used in the preparation of dyestuff intermediates, plasticizers, and stabilizers. It is used directly as a stabilizer for chlorinated solvents and insecticides and chlorine containing polymers. Epichlorhydrin is a raw material for the manufacture of a host of other chemicals. Literature Cited 1 P. Castan: U.S. Patent 2324,483 (July 20, 1943) 2 M. DeGroote (to Petrolite Corp., Ltd.) VS. Patent 2376,624 (April 13, 1937) 3 M. Steindorff, B. Balls, G. Horst, R. Michel (to General Aniline and Film Corp.), U.S. Patent 2,213,477 (September 3, 1940) 4 J. R. Dudley and L. A. Lundberg (to American Cyanamid Co.) U.S. Patent 2,469,683 (May 10, 1949) M. W. .Michael (to American Cyanamid Co.) U-S. Patent 2,543,666 (February 27, 1951) 9J. H. Daniel, Jr. and C. C. Landes (to American Cyanamid Co.) U.S. Patent 2,595,935 (May 6, 1952) 5 J. H. Daniel, Jr. and C. G. Landes (to American Cyanamid Co.) U.5. Patent 2,573,956 (November 6, 1951) r H. L. Yale et. al., J. AM. CHEM. SOC. 72,3710-16 (1950) * N. B. Tucker (to the Procter and Gamble Co.) U.S. Patent 22289,391 (July 14, 1942) * A. S. Richardson (to the Proc ter and Gamble Co.) U.S. Pat ent 2383,737 (August 28, 1945) 1#H. B. iTbcker (to the Procter and Gamble Co.) U.S. Patent 23343f7-4November 16. 1943) 'Available from Union Carbide Chemicals Company. CONFIDENT^7-,- 16 of SubjecIt; t.o r> r- +. ' Order It th judicial L> j. s t r i n f- Nc trict Si-1145 Court The presence of ethylene dichloride in the air can be detected by its characteristic sweet, ethereal odor long before its concentration approaches 6.2 per cent. The addition of carbon tetrachloride renders ethylene and propylene dichlorides safe, with regard to fire hazard, under ordinary con ditions of storage or use. A mixture of 75 per cent ethylene dichloride and 25 per cent carbon tetrachloride by volume is classed as "Non-Flammable" by Underwriters' Laboratories and by the U. S. Bureau of Explosives. This mixture is not approved for use as a fire-extinguishing liquid. Stability Ethylene dichloride has the lowest acidity specification and is the most stable of the chlorinated hydrocarbons. It is resistant to hy drolysis and oxidation in the presence of air, water, or metals at tempera tures up to 100C. In the absence of air and water, it is stable up to I60C. Trichlorethane is stable in the presence of air at ordinary temperatures and in the absence of air and water up to 110C. The following table summarizes the resistance of various chlorinated solvents to loss of chlorine in aqueous solutions of acids, bases, and reducing and oxidizing agents. In comparing the figures given, only large differences should be considered significant. Inhibitors can be added to chlorinated solvents to minimize the development of acidity. These inhibitors are usually weak nitrogen bases such as the pyridines. Comparative Stability Chlorinated Compound 8.4% Sodium Bicarbonate 6% Acotic Acid Iron Powdar 2% Hydrogon Poroxida Mg. of Chlorida ion por 100 ml. of Compound Rofluxod for 48 Hour*: Ethylone Dichlorido Propylono Dichlorido Trichlorothano 1732 225 2160 55 30 12 64 23 1982 342 188 106.4 Dichlorofhyi Ethor Dlehioritopropyl Ethor Triglycol Dichlorido 348 694 78 632 135 284 71 320 263 557 99 895 Butyl Chlorldo Ethylono Chlorhydrin 293 3080 145 2160 64 167 650 1188 Carbon Totrachlorido M 10 1860 9 Subiect- < n nrn).n,,, * of 7, -- ^ecLive Order ^ Julcial District Court No. 91-1145 IS St 4$ 1 tjflSP ()f RoCOl'PrY Narrow boiling range and complete volatility simplify the removal of chlorhydrocarbons from extracted material and facilitate economical recovery of the solvent. No "heavy-ends" are left in the extract or in the residue. Boiling range and heat of vaporization of chlorhydrocarbons are low enough to permit easy distillation without using excessive temperatures and to give minimum loss on handling. HANDLING AND STORAGE OF CHLORINATED COMPOUNDS In using organic chlorine compounds, particular attention must be given to adequate ventilation. Prolonged or repeated breathing of vapors or contact with skin and eyes must be avoided. Additional precautions may be necessary with particular compounds. Physiological properties and tox icity information are given on pages 20 and 21. From the data given on page 17 in the section on "Advantages of Chlorinated Solvents", it is evident that chlorinated solvents have a low order of flammability and their fire hazard is small. These compounds react in varying degrees with different metals. For safety reasons and to avoid contamination, care must be taken in the selection of storage containers and piping, pumps, and other processing equipment. Steel drums or tanks coated with a baked phenolic resin have been found to be the most satisfactory type of storage container for chlorinated compounds. Butyl chloride and ethylene chlorhydrin should be stored only in these resin coated containers. Aluminum should never be used for the storage of chlorinated compounds. When freshly distilled and of a low acid content, most of the chlori nated compounds can also be stored in containers constructed of mild steel, 18-8 stainless steel, nickel, galvanized iron, or tinned iron. If the acidity increases, however, due to prolonged storage, the rate of attack on unprotected metals may be appreciable with subsequent contamination of the solvent. Steel piping is generally satisfactory for the transfer of chlorinated compounds. If corrosion of the lines or discoloration of the material are to be-avoided during prolonged storage or recycling, then the lines should be drained after use. If this procedure proves impractical, baked phenolic resin coated steel pipes are recommended to minimize contamination. Additional information on the storage and handling of chlorinated compounds may be found in the following Manufacturing Chemists' Associ ation pamphlets -- Ethylene Dichloride SD-18 and Carbon Tetrachloride SD-3. CONFIDENTIAL: Subjee t to Protective Order of 14th judicial District Court No. 91"11^ 5 SL 49274 19 PHYSI LOGICAL PROPERTIES 6 These organic chlorine compounds differ greally from one another in their toxicity as indicated by the table on the right. As a general rule, the major hazard in their industrial applications and use is from vapor inhalation. Penetration through the skin by those compounds with a single skin absorption dose for rabbits of 1 milliliter per kilogram or less is hazardous. None of these chlorine compounds is highly irritating to the skin, but like many solvents, they would have a solvent action on the skin. Additional information on physiological 'properties may be obtained from the literature referred to on page 42. Hand ling and storage of chlorine compounds are discussed on page 19. Toxicity is only one indication of the existence of hazard in handling a chemical. Other factors, such as physical properties, and extent of exposure are equally important in determining the hazard. These tabular data on the next page indicate relative toxicity to animals. The results of animal experiments may be indicative of the effects to be expected on human subjects, but they cannot be freely applied to humans. Definitions: The National Research Council defines toxicity as the capacity of a substance to produce injury. Hazard is the probability that injury will result from the use of the substance in the quantity and manner proposed. The term, LD60 refers to that quantity of chemical which kills 50 per cent of exposed animals. For uniformity, dosage is ex pressed in grams or milliliters per kilogram of animal body weight. Single skin absorption refers to a 24-hour skin contact with the liquid chemical. Single inhalation refers to a single continuous breathing of a certain concentration of chemical for a given period of time. Primary irritation refers to the skin response following a 4-hour uncovered skin exposure.' Eye injury refers to surface damage produced by the liquid chemical. The word poison is used as defined by the Manufacturing Chemists' Association and the Interstate Commerce Commission. Legal responsibility is assumed only for the fact that all studies reported here and all opinions are those of qualified experts. Ethylene Dichloride CHLORASOL Fumigant and Solvent (Solvent EDM) Propylene Dichloride ** 1,1,2-Triehlorethane Butyl Chloride 2-Ethylhexyl Chloride Dlchlorethyl Ether CKLOREX Solvent Dichlorisopropyl Ether Triglycol Dichlorldo *Ethylona Chlorhydrin *Epichlorhydrin * Poison. ** Not to be confused with methyl chloroform (1,1,1 ,-trichlorethane). CONFIDENTIAL: Subject to Protective OtdeT of 14th Judicial District Court 20 No. 91-1145sl_ 049275 5 Single Oral LDio Dose Rati fl./kg. , 0.77 1.64 2.27 1.14 Single Skin Absorption, LDto Dos* Rabbit* ml./kg. Sinaia Inhalation Rat* Saturated Vapors 3.89 5.99 8.75 3.73 200 ppm., 1 hr, killed 1 of 10. 2 min, killed 1 of 6. 5 min, killed 6 of 6. 15 min. killed 1 of 6. 30 min. killed 3 of 6. 1 hr. killed 6 of 6. ' 500 ppm., 4 hr*, killed 1 of 6. 8 hr*, killed 4 of 6. Primary Irritation, Rabbits' Skin None None None Minor 2.67 - >" 0.105 0.24 0.25 0.089 0.09 20 ml./kg. killed 1 of 4. 15.8 0.72 0.72 15 min. killed none of 6. 30 min. killed 6 of 6. 2 hr*, killed 2 of 6. 8 hr*, killed 2 of 6. 1 hr. killed none of 6. 2 hr*, killed 2 of 2. 1 hr, killed none of 6. 2 hr*, killed 2 of 2. 3.00 1.41 0.105 1.3 4 hr*, killed none of 6. 8 hr*, killed 6 of 6. 8 hr*, killed none of 4. 30 *ec. killed none of 6. 10 min. killed 6 of 6. 250 ppm,, 4 hr*, killed none of 6. 8 hr*, killed 4 of 6. Mild Minor Minor Minor None Minor None Minor Eye Injury, Rabbits Minor Minor Minor Minor Minor None None None Minor None None Moderate -T 7s \ ot^gT rv , -o '* I i1 0V" -p 'I ,,..},4-f k- ^ \7 ` <* c * . -t " 01s xVA5 f l^tn J ^0. 91 o $ 04 9^6 21 SHIPPING DATA This table presents the various data that pertain to Carbide's chlorinated compounds as they are shipped commercially. The table gives the pounds per gal lon for each chlorinated compound, its flash point, and net container contents in pounds; and it indicates the various labels that are required by law to be on each container. Chlorinated Compound Ethylene Dichloride CHIORASOL Fumigant and Solvent Propylene Dichloride 1,1,2-Trichlorethane Pound* per gal. at 20 C. Coefficient of Expansion at 55 C. Flash Point, F. Open Cup 10.45 11.12 9.64 0.00121 0.00122 0.00118 70 No Flash 70 11.94 0.00082 No Flash Container contents ore sub/ect to change. Butyl Chloride 2-Ethylhexyl Chloride Dichiorethyl Ether CHLOREX Solvent Dichlorisopropyl Ether Triglycol Dichloride 7.38 7.33 0.00131 0.00101 15 140 10.17 10.17 9.29 9.97 0.00100 0.00100 0.00098 0.00095 185 185 185 250 AD, Ethylene Chlorhydrin Epichlorhydrin 10.03 9.84 0.00092 0.00104 140 105 TOC- <<> ve 22 CO' v,-\ecv' SM^tVi 3U ,ct^ tI ni5 VV^ 9v ^o- SL 049277 0 Net Container Contents and Type of Containers 1-gal. Can 5-gal. Drum 55-gal. Drum Labels Required Freight Description Bureau of Explosives Description on Container 10.0 lb.; tin 11.0 lb.; tin 9.5 lb.; tin 1 2.0 lb.; tin 50 lb.; ICC 17E iron drum 55 lb.; ICC 17E doublecoated, resin-lined iron drum 45 lb.; ICC 17E doublecoated, modified phenolic resin-lined iron drum 60 lb.; ICC 17E doublecoated, resin-lined iron drum 570 lb.; ICC 17E iron drum with "Garlock" gasket 600 lb.; ICC 17E doublecoated, resin-lined iron drum with "Garlock" gasket 520 lb.; ICC 17E doublecoated, modified phenolic resin-lined iron drum with "Garlock" gasket 650 lb.; ICC 17E doublecoated, resin-lined iron drum with fiber gasket Red None Red None Ethylene Dichloride Same Insecticides, Noibn, O/T Agricultural None Propylene Dichloride (Flammable Liquid NOS) Flam. Liq. NOS Trichlorethane None 7.0 lb.; tin 7,0 lb.; tin --1 10.0 lb.; tin 10.0 lb.; tin 9.0 lb.; tin 9.5 lb.; tin 35 lb.; ICC 17E iron drum 35 lb.; ICC 17E iron drum 400 lb.; ICC 17C iron drum with fiber gasket 400 lb.; ICC 17E iron drum with "Garlock" gasket Red None 50 lb.; ICC 17E iron drum 50 lb.; ICC 17E iron drum 45 lb.; ICC 17E iron drum 50 lb.,- ICC 17E doublecoated, epoxy-phenolic resin-lined iron drum 560 lb.; ICC 17E iron drum with "Garlock" gasket 560 lb.; ICC 17E iron drum with "Garlock" gasket 510 lb.; ICC 17E iron drum with "Garlock" gasket 550 lb.; ICC 17E doublecoated, epoxy-phenolic resin-lined iron drum with polyethylene gasket None None None None Chemicals, Noibn Chemicals, Noibn Dichloroethyl Ether Dichloroethyl Ether Paint and Varnish Solvent, Noibn Paint and Varnish Solvent, Noibn Same None None None None None 10.0 lb.; tin 9.5 lb.; tin 50 lb.,- ICC 17E doublecoated, epoxy-phenolic resin-lined iron drum 45 lb.; ICC 17E iron drum 550 lb.; ICC 17E doublecoated, epoxy-phenoiic resin-lined iron drum vdth polythylene gasket 540 lb.; ICC 17E iron drum with fiber gasket Poison B Ethylene Chlorhydrin Poison B Epichlorhydrin Poison B Poisonous Liquid NOS vO ^ ntX* t yO V^ SL 049278 23 SPECIFICATIONS AND TEST METHODS The following table (pages 24 and 25) gives the specifications for Carbide's organic chlorine compounds when this book was printed. Improve ments are constantly being made in all products Carbide manufactures. Consequently, these speci fications are subject to change. For the latest specifications on any of these products, please contact the Sales Office nearest you. Our rep resentatives will be glad to furnish the informa tion. A list of the addresses of these offices is on the outside back cover. To use this table, look in the left-hand vertical column for the product and in the top horizontal column to find the requirement. At the intersec tion are the specification limits and a key to the corresponding specification method or quality control test. For example, the water requirement for ethylene dichloride is 0.03 per cent by weight, maximum, using the method Gl. This method is found under the "key" column on page 28, which gives the specific sample size for determining water in ethylene dichloride when the general method G is used. The test methods used in determining the specifications of Carbide's products are either A.S.T.M. tests or recognized tests that have been improved or simplified in our laboratories. ' Chlorinated Compound Ethylene Dichloride b Chlorasoi Fumigant mim a* Solvent EDM Propylono Dichloride 1,1,2-Trichlorethane Butyl Chloride b Dichlorethyl Ether Chlorix Solventb Dichlorisopropyl Ether Triglycol Dichloride Ethylene Chlorhydrln b Epichlorhydrin b < Specific Gravity, 20 20 C. Limits Method Limits Method Limits Method Limits Method 1.2550 to 1.2570 A 1.334 to 1.339 B 1.157 to 1.160 B 1.425 to 1.445 B Limits Method Limits Method Limits Method Limits Method Limits Method Limits Method Limits Method 0.885 to 0.889 B 1.219 to 1.224 B AN 1.219 to 1.224 B 1.113 to 1.119 B 1.195 to 1.200 B 1.202 to 1.208 B 1.180 to 1.185 B No turbidity at temperature indie* to C't D, CoUrt. ot ** 54 04 92?g 24 Distillation at 760 mm. Hg % by wt. max. as hydro chloric acid Cold Test* Water % by wt. Nonvolatile* max. g./lOO ml. Color Pt-Co unit*. max. Odor Suspended Matter ----________ ** vF Shall distill entirely within a l.5C. range including 83.5C. C Ibp 75.0C., min. Dp 85.0C., max. C Ibp 94.0C., min. Dp 98.0C., max. C Ibp 1 10.0C., min. Dp 1 1 5.0C., max. C Shall distill entirely within a 1.5C. range including 78.4C, C ibp 175C., min. Dp 1 81 "C., max. D Ibp 175C., min. Dp 181 C., max. 5 ml. 95 ml. D 180C., min. 1 90C., max. C Ibp 230C., min. Dp 245C., max. C Ibp 12A.0C., min. Dp 1 32.0C., max. C Ibp 11 3.0C., min. Dp n8.0C., max. c 0.001 El 0.001 --20C. F 0.03 G1 0.05 E2 0.005 E3 0.02 --5C. F G2 E7 0.005 E6 0.005 --20C. 0.10 G3 0.10 E4 0.005 F --30C. G3 0.10 E4 0.01 F G3 0.10 E5 0.03 G2 0.2 E8 0.02 G4 E8 0.10 G5 0.001 max. H 0.005 max. 10 1 15 H 0.005 max. t H 1 15 1 15 0.005 max. H 1 15 1 30 1 150 1 40 1 100 1 20' 1 15 1 Non-residual J Non-residual J Mild J Mild and non-residual J Substantially free K Substantially free K Substantially free K Substantially free K Substantially free K Substantially free K Substantially free K Substantially free K Substantially free K Substantially free' K b ,S#< also Chart of Miscellaneous Specification Requirements, p. 26, c If shipped in glass; otherwise this requirement will not be Included. Ts VJ,*.. -'ri' we cc^' vi0'=0 . c^ 'tfi si 04g 25 28q MISCELLANE US SPECIFICATION REQUIREMENTS ETHYLENE DICHLORIDE BUTYL CHLORIDE "Chlorex" SOLVENT ETHYLENE CHLORHYDRIN EPICHLORHYDRIN TRIGLYCOL DICHLORIDE 26 Requirement Limit* Method Requirement Limit* Method Requirement Limits Method Requirement Limits Method , Ethylene Dichloride 99.0% by wt., min. L Tendency to Hydrolyze 1 *t extraction 1.0 ml,, max. 2nd extraction 0.1 ml,, max. 3rd extraction 0.1 ml., max. M Butanol 0.8% by wt. max. O Ethylene Dichloride 1.0% by wt. max. This requirement i* limited by the distillation range. D Ethylene Chlorhydrin 98.0% by wt., min. P1 Water Solubility Miscible in all proportions Q Ammoniacal Silver Nitrate Te*t No Coloration N Requirement Limit* Method Epichlorhydrin 98.0% by wt., min. R Requirement Limit* Method Total Chlorine 3 7 to 38% by wt. S ____ ______ . A' * V* ^ r J*GC <* C)V *` S1.0A9281 Modern analytical equipment helps maintain the high quality of Carbide's products. TEST METHODS KIY A MITHOD SPECIFIC GRAVITY E Determine at 20C. by means of a 60-ml. 'rPyrex"glass pycnometer calibrated to give the apparent specific gravity at 20/20C. Main tain the constant temperature bath at 20 + 0.05C. SPECIFIC GRAVITY Determine at 20C. by means of a hydro meter calibrated to give the apparent specific gravity at 20/20C. and capable of being easily read to the nearest 0.0005 unit. Main tain the constant temperature bath at 20 0.05C. DISTILLATION Conduct the distillation test in accordance with the American Society for Testing Mate rials Tentative Methods of Test for Distillation Range of Lacquer Solvents and Diluents (ASTM Designation; D 1078) except to use a 100-ml. standard distillation flask as speci fied in ASTM D 86, and to use a gas burner as the source of heat. Use the proper ASTM El E2 E3 E4 E5 E6 E7 E8 E9 METH D thermometer, or an equivalent thermometer of suitable range, calibrated for 100-mm. im mersion. graduated in 0.2C. units, and cap able of being easily read to 0,1C. Conduct the distillation at 760 mm. or ap ply the boiling point correction given in the Physical Properties Table on page 5. DISTILLATION Conduct the distillation test in accordance with the American Society for Testing Mate rials Tentative Methods of Test for Distillation Range of Lacquer Solvents and Diluents (ASTM Designation D 1078) except to use a gas burner as the source of heat. Use the proper ASTM thermometer, or an equivalent thermometer of suitable range, calibrated for 100-mm. immersion, graduated in 0.2C. units, and capable of being easily read to 0.1C. Conduct the distillation at 760 mm. or ap ply the boiling point correction given in the Physical Properties Table on page 5. ACIDITY Measure the specified amount of sample in a graduate and transfer to a 250-ml. Erlenmeyer flask. Add a few drops of 1.0 per cent alcoholic solution of phenolphthalein indicator and titrate with standard alcoholic potassium hydroxide to a pink end-point permanent for at least 15 seconds. Calculation ml. KOH x factor = acidity, % by weight Sample and Reagent Sample, ml. 116 55 63 60 65 82 51 61 25* Normality of KOH 0.02 0.02 0.02 0.1 0.1 0.1 0.02 0.1 0.02 Factor 0.0005 0.001 0.001 0.005 0.005 0.005 0.001 0.005 0.002 * Transfer the sample to a 150-ml. separatory funnel; wash with 100 ml. of neutral distilled water and determine the acidity of the aqueous layer. ^co to r t y. -yV e nS-T' '' 27 o*- SL 049282 MITHOD COLD TEST Transfer 25 ml. of the sample to a 150-mm. test tube and immerse the tube in a suitable cold bath maintained at approximately 15C. below the temperature limit given in the spec ification. Stir the sample continuously with a suitable thermometer until the specified temperature is reached. Examine the contents of the tube for evidence of cloudiness or turbidity. WATER Reagent -- Transfer 487 ml. of freshly distilled anhydrous pyridine to a 4-liter bottle having a 29/42 ground-glass neck. Add 154 g. of reagent-grade iodine, stopper securely, and place on a mechanical roller for 30 min. or until the iodine is completely in solution. Dilute the contents of the bottle to 3500 ml. with anhydrous c.p. methanol. By means of a suitable glass tube extending to the bottom of the bottle add 115 g. of refrigerant-grade sulfur dioxide dried by passing through con centrated sulfuric acid. Allow the contents of the bottle to cool and fit the bottle with a 50-ml. automatic buret having a 29/42 ground-glass joint. Protect all vents open to the air with Ascarite tubes. Much of the accu racy of the method is lost if an ordinary buret is used without special precautions. Standardization -- Place 25 ml. of sub stantially dry methanol in a 125 ml. glassstoppered Erlenmeyer flask and titrate with the reagent to the first permanent reddishbrown end-point. Do not confuse the light yellow color formed during the addition of the first few ml. of reagent with the true end point. . Introduce 1 or 2 drops (0.03 to 0.05 g.) of distilled water weighed to the nearest 0.1 mg. by means of a suitable weighing pipet. Again titrate to the same reddish-brown end point. Make several check determinations. Calculation g. water X 100 = factor = g. water consumed ml. titration by 100 ml. of reagent KIT G1 G2 G3 ' G4 G5 H MITHOD Procedure -- For the sample proceed as directed above to the addition of water. Pipet the prescribed amount of the sample into the flask and immediately titrate with the reagent to the same reddish-brown end-point as that observed in the standardization. ml. titration X factor = water, % by weight ml. of sample X sp. gr. of sample Sample, ml. 100 50 25 15 10 NONVOLATILE MATTER From a graduate introduce 100 ml. of sample into a 125 ml. platinum evaporating dish which has been heated to constant weight at 105 to 110C,, cooled in a desiccator, and weighed to the nearest 0.1 mg. Evaporate the sample to dryness on a hot water bath and place the dish in an oven maintained at 105 to 110C. for 30 minutes or until constant weight is attained. Cool the dish in a desiccator and weigh the residue to the nearest 0.1 mg. Calculation g. residue = nonvolatile matter, g. per 100 ml. COLOR Prepare suitable platinum-cobalt color standards according to the method described in the American Public Health Association's "Standard Methods for the Examination of Water and Sewage", 8th edition (1936). Transfer 100 ml. of the sample to one ol two matched tail-form Nessler tubes. Fill the second tube to the mark with the platinumcobalt standard representing the maximum limit permitted by the specification. Substitute 0.005 per cent potassium dichromate solution for the platinum-cobalt standard, if specified. Compare the colors of the sample and the standard by viewing vertically down through 28 ct CO v t>is'' 3^d--C'nl .u45 \VO- ' s^* 0 fc92.8^ MITHOO KIY [he tubes against a white background. If the exact color of the sample is desired, replace the standard in the second tube with other standards until a satisfactory match is obtained. ODOR Pour a few' ml. of the sample on a clean filter paper and observe the odor at once. If specified, allow the sample to evaporate in air at room temperature and notice whether any residual odor remains on the paper. SUSPENDED MATTER Invert a bottle of the sample and examine by transmitted light. ETHYLENE DICHLORIDE Prepare a sodium methylate solution by adding short pieces of sodium wire to 500 ml. of anhydrous methanol until effervescence ceases. Handle the sodium wire with caution! Transfer 75 ml. of this solution to each of two 250-ml. Erlenmeyer flasks fitted with a 24/40 standard-taper joint. Reserve one of the flasks as a blank and into the other flask introduce 1.2 to 1.4 g. of the sample weighed to the nearest 0.1 mg. by means of a suitable weighing pipet. Attach the flasks to 500-mm. brine-cooled "'West" condensers fitted with 24/40 standardtaper joints, heat to boiling by means of a 500-watt electric mantle, and allow to reflux for one hour. Remove the mantles and allow the flask to cool to room temperature. Wash down the inside walls of each condenser with 50 ml. of distilled water and catch the rinsings in the flask. Add 1 ml. of a 1.0 per cent alcoholic solu tion of phenolphthalein indicator and then add a slight excess of 2 N nitric acid. Neutral ize the excess with powdered calcium carbon ate. Add one ml. of 10 per cent potassium chromate and titrate with standard 0.15 N silver nitrate to the first permanent reddish tinge. Calculation (A-B)N X 9.896 = Ethylene Dichloride, % g. sample by weight M MITH 0 A = ml. of N normal AgNOj required for the sample B = ml. of N normal AgN'Oj required for the blank TENDENCY TO HYDROLYZE Transfer 200 ml. of distilled water to a 500-ml. separatory funnel, add 200 ml. of the sample, and shake vigorously for 10 minutes. Allow the mixture to separate into two layers, and transfer 100 ml. of the upper (water) layer to one of two 250-ml. Erlenmeyer flasks. Discard the remainder of the upper layer. To the second Erlenmeyer flask add 100 ml. of distilled water and reserve as the blank. Add 3 to 4 drops of a 0.04 per cent alco holic solution of bromothymol blue indicator to each flask and titrate with standard 0.01 N barium hydroxide to the first permanent bluish end-point. Make two subsequent water extrac tions of the sample layer by adding 200 ml. of distilled water to the contents of the sep aratory funnel each time and repeating the above procedure. Calculation A-B = ml. of reagent per extraction A = ml. of N normal Ba(OH) j required for sample B = ml. of N normal Ba(OH)2 required for blank AMMONIACAL SILVER NITRATE TEST Ammoniacal Silver Nitrate SolutionAdd a 10 per cent aqueous solution of am monium hydroxide dropwise to 100 ml, of a 5 per cent aqueous solution of silver nitrate until the precipitate which first forms is almost but not entirely dissolved. Filter the solution and store the filtrate in a dark col ored bottle. CAUTION! Ammoniacal silver nitrate reagent readily forms explosive compounds on stand ing. Do not store this reagent but prepare a fresh quantity for each series of determina tions. Neutralize the excess reagent and rinse all glassware used with concentrated hydro chloric acid immediately after completing the test. CONFIDENTIAL: Subject to Protective Order of 14th :/ el District Court Si 4g ^84 METHOD Procedure -- Transfer 10 ml. of the re agent to a 150-mm. test tube, add 10 ml. of the sample, and mix thoroughly. Allow the mixture to stand in the dark for 20 minutes at 20C- and examine visually for any evidence of coloration in both layers. The lower layer may be turbid from the suspension of water in the sample, but no coloration should be present. BUTANOL Phthallc anhydride-pyridine reagent -- Add 42 g. of c.p. phthalic anhydride to 300 ml. of freshly distilled pyridine contained in a one-quart glass-stoppered brown bottle. Shake the bottle vigorously until complete solution is effected. The reagent preferably should stand overnight before using; however, the solution may be heated under hot tap water until a slight cooling of the reagent occurs, indicating complete reaction. Procedure -- Prepare a sufficient number of heat-resistant pressure bottles to make all blank and sample determinations in duplicate. Carefully pipet 25 ml. of the phthalic anhy dride-pyridine reagent into each of the bottles, using the same pipet for each transfer. Do not allow the reagent to come in contact with the rubber gasket. Before capping purge the bottles for 2 minutes with a gentle stream of nitrogen by means of a glass tube inserted through the neck of the bottle and clamped so that the opening is just above the surface of the^liquid. Reserve two of the bottles as blanks. Into each of the other bottles, introduce 25 ml. of the sample by means of a suitable transfer pipet. Stopper the bottles and wrap each securely in a canvas bag. Place the samples and blanks as close together as pos sible in a water bath maintained at 982C. for 60 minutes. Maintain sufficient water in the bath to just cover the liquid in the bottles. Remove the bottles from the bath and allow them to cool in air to room temperature. When the bottles have cooled, loosen the wrappers, uncap to release any pressure, and then re move the wrappers. To each bottle add exactly 50 ml. of stand ard 0.5 N sodium hydroxide, using the same 30 KEY METHOD pipet for each addition. Be sure to allow the f same drainage time for each bottle as this amount is not considered in the final calcula tions. Add 5 drops of a 1.0 per cent pyridine solution of phenolphthalein indicator and ti trate with standard 0.5 N sodium hydroxide to a pink end-point permanent for at least 15 seconds. Agitate the contents of the bottle vigorously during the titration. Calculation (B-A)N X 7.41 --------------------= butanol, % by weight 25 X sp.gr. * A= ml. of N normal NaOH required for the sample B= average ml. of N normal NaOH required for the blank ETHYLENE CHLORHYDRIN | Prepare a sufficient number of heatresistant pressure bottles to make all blank and sample determinations in duplicate. To each of the bottles, add 50 ml. of 0.5 N sodium hydroxide from a buret and exactly 10 ml. of i 0.1 N hydrochloric acid by means of a transfer pipet. Reserve two of the bottles for blanks. Into each of the other bottles, introduce the prescribed amount of sample weighed to the nearest 0.1 mg. by means of a suitable j weighing pipet. Fit the bottles with pressure stoppers, wrap each securely in a canvas bag, and place the samples and blanks as close together as possible in a hot water bath main tained at a temperature of 982C. for 45 minutes. Remove the bottles from the bath and allow them to cool in air to room temoerature. When the bottles have cooled, loosen the wrappers and uncap carefully to release any pressure. Wash down the inside walls of each bottle with a few ml. of distilled water. Carefully wash any liquid on the stopper into the bottle. Add 6 to 8 drops of phenolphthalein indi cator and neutralize the excess caustic by the dropwise addition of 2 N nitric acid until the pink color just disappears. Add 1 ml. excess acid and slowly add powdered calcium car bonate until effervescence ceases. Add about 40 ml. of fresh 1.0 per cent aqueous starch t CONFIDENTIAL: Subject to Protective Ottier , Of 14t.h Judicial District Cburt i!o. 91-1.145 SL 049285 MITHOD KIT METHOD solution and titrate with standard 0.1 N silver nitrate until approximately 3 ml. of reagent has been added. Add 25 drops of a 0.05 per cent methanolic solution of dichlorofluorescein indicator and continue the titration to the first permanent pink end-point, swirling the con tents of the flask vigorously during the titra tion. Calculation (A-B)N XF M ---------------- = chlorhydrin, % by weight g. sample A = ml. of N normal AgNO.i required for sample B = average ml. of N normal AgNOs required for blank F = factor Sample and Conditions them to cool in air to room temperature. When the bottles have cooled, loosen the wrappers, uncap to release anv pressure, and then remove the wrappers. To each bottle add exactly 10 ml. of 0.1 \ hydrochloric acid and 2 drops of a 1.0 per cent alcoholic solution of phenolphthalein in dicator. Add sufficient 2 N nitric acid to just discharge the red color. Slowly add powdered calcium carbonate until effervescence ceases. Add 40 ml. of fresh starch solution and 25 drops of a 0.05 per cent methanolic solu tion of dichlorofluorescein indicator; titrate with standard 0.1 N silver nitrate to a per manent pink end-point, swirling the contents of the bottle vigorously during the titration. Calculation (A-B)N X 9.25 --------------------= epichlorhvdrin, 9, by wt. g. sample Sample, g. 0.4 to 0.7 Factor 8.05 WATER SOLUBILITY A = ml. of N normal AgNCb required for the sample B = ml. of N normal AgNOa required for the blank Transfer 25 ml. of sample to a 125-ml. Erlenmeyer flask and add 25 ml. of distilled water in 5-ml. portions, shaking the flask well after each addition. Maintain the temperature of the solution at 25C. Add 25 ml. of the sample to 25 ml. of distilled water in the same manner. The sample is completely miscible if there is no cloudiness or turbidity at any time. EPICHLORHYDRIN Add from a buret exactly 75 ml. of 0.5 N alcoholic potassium hydroxide to each of three clean dry heat-resistant pressure bottles. Re serve one of the bottles for a blank. Into each of the other bottles introduce 0.5 to 0.8 g. of the sample weighed to the nearest 0.1 mg. by means of a suitable weighing pipet. Stopper the bottles and swirl the contents to effect solution. Wrap the blank and samples in canvas bags or pieces of cloth and place them on a steam bath at 98 + 2C. for 45 minutes. Re move the bottles from the bath and allow TOTAL CHLORINE Sodium methylate, approximately 4 N--Carefully add sodium or sodium wire to anhydrous methanol until hydrogen no longer is evolved. Adjust the concentration with ad ditional methanol if necessary. Standard 0.5 N sodium methylat in pyridine--Prepare this reagent at least one day before using. Transfer 125 ml. of the 4 N sodium methylate to a 1000-ml. volumetric flask containing 125 ml. of anhydrous meth anol. Dilute to the mark with redistilled pyr idine. This reagent readily absorbs carbon diox ide from the air, and is best preserved and used in a 50-ml. automatic buret. All vents open to the air must have protective Ascarite tubes. Standardize this reagent daily as described be low. Transfer 50 ml. of freshly distilled pyri dine to each of four 250-ml. glass-stoppered Erlenmeyer flasks. Reserve two of the flasks for the blank determination. Into each of the other flasks introduce 1.4 cd is: Subject t'*'of 14th Juclic No. U!;ocr ,J -* D J. s L r i c t Court 91-1145 SL 0*9286 MITHOD to 2.0 g, of Bureau of Standards benzoic acid weighed to the nearest 0.1 mg. by means of a tared watch glass. Stopper the flasks and swirl to effect complete solution. Add 2 or 3 drops of 1.0 per cent solution of thymolphthalein indicator in pyridine to each flask and titrate immediately with the sodium methylatepyridine reagent to the first blue end-point. Standard sodium methylate-pyridine W N, normality of the sodium 0.1221 x (C-D)_ ~ methylate-pyridine C -- ml. of NaOCH3 required for the benzoic acid D = average ml. of NaOCH 3 required for the blank W = g. of certified benzoic acid used AN/At = 0.0005 per C. for 0.5 N NaOCH 3 Procedure--Prepare a sufficient number of clean, dry, heat-resistant pressure bottles to make all blank and sample determinations in duplicate. Pipet 25 ml. of anhydrous ethylene diamine into each of the bottles using the same pipet for each transfer. Reserve two of the bot tles for the blank determination, taking care to uncap and expose the contents to the air for the same length of time as the samples. KIY ! MITHOD I Into each of the other bottles introduce 0.9 to 1.9 g. of the sample weighed to the near est 0.1 mg. by means of a suitable weighing pipet. Fit each bottle with a pressure stopper and wrap securely in a fabric bag. Place the samples and blanks as close together as pos sible in a steam bath maintained at 98 2C. for 30 minutes. Maintain sufficient water in the bath to just cover the liquid in the bottles. Remove the bottles from the bath and allow them to cool in air to room temperature. When the bottles have cooled, loosen the bags, uncap to release any pressure, and then remove the bags. To each bottle add 50 ml. of redistilled pyridine, 2 or 3 drops of 1.0 per cent thymolphthalein indicator in pyridine and ti trate with standard 0.5 N sodium methylatepyridine to the first blue end point. Calculation (A-B)N x 3.55 total chlorine, per cent by g. sample weight A = ml. of N normal sodium methylatepyridine required for the sample B = average ml. of N normal sodium methy late-pyridine required for the blank Sub jecc io Of 14 h J U d i c i n C::der o-'surict Court No. 91-1145 32 0A9287 sk* COMPONENTS AZEOTROPE CONSTANT BOILING MIXTURES * At 50 mm. Ho b At tOO mm. Hg Compound Boiling Point, C. at 760 mm. Hg Boiling Point, C. at 760 mm. Hg Composition, % by wt. in azeotrope Butyl chloride Water Dichlorothyl othor Ethylene glycol 78.6 100.0 96* 123* 68.0 92.7* 93 7 Dichlorothyl othor 2-Ethylhexanol Dichlorothyl othor 3-Hoptanol Dichlorothyl othor Water Dichlarisopropyl other Water Epichlorhydrin ' Propanol Epichlorhydrin Toluene Epichlorhydrin Water Ethylene chlorhydrin Vinyl 2-chlorethyl ether Ethylene chlorhydrin Water Ethylene chlorhydrin Water Ethylene chlorhydrin Water Ethylene dichlorido Carbon tetrachloride Ethylene dichlorido Ethanol Ethylene dichlorido Ethanol Water Ethylene dichlorido Isopropanol Ethylene dichlorido Isopropanol Water Ethylene dichlorido Methanol Ethylene dichlorido Trichlorethylene Ethylene dichlorido Water 96* 109* 179.2 156.4 179.2 100.0 187.0 100.0 115.2 97.2 115.2 110.6 115.2 100.0 128.7 109.1 60* 38* 75 b 51.6b 128.7 100.0 83.5 76.5 83.5 78.3 83.5 78.3 100.0 83.5 82.3 83.5 82.3 100.0 83.5 64.5 83.5 87.1 83.5 100.0 96" 141.2 98 98.5 96 108.3 88.5 108.8 37.1 * 51.1 b 97.8 75.3 71.0 67.8 72.7 69.7 59.5 82.3 71.6 90 10 28 72 34.5 65.5 37.4 62.6 23 77 26 74 74 26 3 97 39.8 60.2 40.7 59.3 42.3 57.7 22 78 66.5 33.5 77.1 15.7 7.2 60.8 39.2 73.3 19.0 7.7 65 35 59.1 40.9 91.8 8.2 2-Ethylhoxyl chloride 2-Ethylbutanol 2-Ethylhexyl chloride 2-Ethylbutanol 2-Ethylhexyl chloride Water 89* 77* 106.9 b 92 b 173.0 100.0 77* 92 b 97.3 39 61 32 68 45 55 Propylene dichlorido Water 96.3 100.0 78.4 89.4 10.6 Trichlorethane Water 113.7 100.0 86.0 83.6 16.4 Triglycol dichlorido Water 240.9 rmo..-.. 99.7 6.0 94.0 4. . , Of 14 th .711i SL 049288;^ ' ^ 1 Order 9* 1- tri 1145 Cl Cour? PHYSICAL PROPERTY CHARTS VAPOR PRESSURE, mm. Hg 0 34 10 20 30 40 50 60 70 80 90 [T)f$priAl!f 160 Subiect to Protec ive Order TEMPERATUREof*Ct4^h Judicial Di or Let Court No. 91-1145 SL 049289 Chart 2 Vapor Pressures at Various Temperatures Chart 3 Specific Gravity at Various Temperatures SPECIFIC GRAVITY, t/2 0 TEMPERATURE, "C. CONFIDENTIAL Subject to Pi fctive Order `pi ^ x 1 c i v-ourt 36 of 14tn J MO 1C,, t-j o. y i i i 13 SL 049291 Chart 4 Specific Gravity of Carbon Tetrachloride Mixtures and Vinyl Chloride Mixtures a oo0 CvJ O ^ cvj .' CVl -* OJ 35 ao: o o u. oO 111 lli a. a. tn in 9 (I) CARBON TETRACHLORIDE, PER CENT BY WEIGHT (2) VINYL CHLORIDE , mol PER CENT Chart 5 Specific Gravity of Solutions of Dichlorethyl Ether and o o IM CM > < oc o a Ll. O HQI. to 9 10 20 30 40 50 60 70 orr 01CHL0RETHYL ETHER, PER CENT |3YoVtGi|*T Fr urt of BO. ^'Usl 37 O4 93 93 CllCirt 6 Solubility of Chlorinated Compounds in Water at Various Temperatures CHLORINE COMPOUND,PERCENT BY WEIGHT Chart 7 Solubility of Water in Chlorinated Compounds at Various Temperatures e> Hi S z UJ o oc LU 0. a: HI < s 38 TEMPERATURE, -C, of 14th ^dida Order -.0,93 9 Chart 8 Viscosities at Various Temperatures 9 Chart 9 Boiling Points of Ethylene Dichloride-Carbon Tetrachloride Mixtures 0'c c10 Chart 10 Comparative Evaporation Rates PER CENT EVAPORATED 0 20 40 60 80 100 120 140 160 180 200 TIME, MINUTES Chart 11 Freezing Points of Trichlorethane-Carbon Tetrachloride Mixtures TEMPERATURE, *C. to 40 20 30 40 50 60 70 80 90 100 TRICHLORETHANE, PER CENT SBY1ub4WjteEhcIGt'JH. fu. dic\>iavol cDeicst:4-vroicOt rdCeorurt f 1 No. 91-1140 sL 049295 f9 Chart 12 Dichlorethyl Ether: Heat of Vaporization vs. Vapor Pressure 100 HO 120 130 140 150 160 170 180 190 200 210 220 HEAT OF VAPORIZATION, B.t.u.PER POUND Chart 13 Refractive Index of Carbon Tetrachloride Mixtures CP 41 Selected References to CHL RINATED COMPOUNDS The following selected references are in addition to the "Literature Cited" given for the individual Chlorinated Compounds in the technical literature. FUMIGATION Bibliographv of Ethvlene Dichloride; W. A. Gersdorff; U. S. DEPT. AGR. Misc. Pub. No. 117 (February, 1932). Insecticidal Fumigation of Farm Stored Grain: T. F. Winburn; AM. MILLER (August, 1940). How to Know and Control Stored-Grain Insects: M. D. Farrar, T. F. Winburn, W. P. Flint; UNIV. ILLINOIS AGR. EXP'T. STA. Cir. 512 (January, 1941). Control of Insect Pests of Grain in Elevator Storage: R. T. Cotton, G. B. Wagner; U. S. DEPT. AGR. FAR MERS' BULL. No. 1880 (August, 1941). Advances in Entomology: C. H. Richardson; CHEM. ENG. NEWS, 20 (February, 1942). Industrial Fumigation Against Insects: E. A. Back; U. S. DEPT. AGR. CIR. No. 369 (August, 1942). Control of Insects in Fourteen Thousand Corn Bins: M. D. Farrar, W. P. Hint; J. ECON. ENTOMOL. 35, 615 (October, 1942). Evaluation of Fumigants for Control of Insects Attacking Wheat and Corn in Steel Bins: H. H. Walkden ana R. B. Schwitzgebel; U. S. DEPT. OF AGR. TECH. BULL. No. 1045, (September, 1951). New Information on Physiological Effects of Trichloroethvlene and Ethvlene Dichloride: H. H. Schrenk; IND. AND ENG. CHEM. 44, (Sup) 119A-120A + (April, 1952). PHYSIOLOGICAL ACTION Acute Response of Guinea Pigs to Vapors of Some New Commercial Organic Compounds--Ethylene Dichloride: R. R. Savers, W. P. Yant, C. P. Waite, F. A. Pattv; PUBLIC HEALTH REPORTS Reprint No. 1349, 45, 225 (January, 1930), Acute Response of Guinea Pigs to Vapors of Some New Commercial Organic Compounds--VII Dichlorethvl Ether: H. H. Schrenk, F. A. Patty, W. P. Yant; PUBLIC HEALTH REPORTS Reprint No. 1602, 48, 1389 (November, 1933). Single Dose Toxicity of Some Glycols and Derivatives: H. F. Smvth, Jr,, J. Seaton, L, Fisher; J. IND. HYG. TOXICOL'. 23, 259 (June, 1941 Toxicology of 1,2-Dichloropropane: L. A. Heppel; J. PHARMACOL. 87, (1) 11-17 (May, 1946). The Toxicology of 1,2-Dichloroethane. III. Its Acute Toxicitv and the Effect of Protective Agents: L. A. Heppel. et al.; J. PHARMACOL. EXP. THERAP. 84, No. 1, 53-63 (Mav, 1945). SOLVENT EXTRACTION Production of Lubricating Oils by Extraction with Di chlorethyl Ether: J. M. Page, Jr.. C, C. Buchler, and S. H. Diggs; IND. ENG. CHEM. 25. No. 4, 418-421 (1933), Critical Solution Temperatures of Paraffins with Nitro benzene and B.-B'-Dicnlorethyl Ether: H. M. Woodburn. K, Smith, and H. Tetewskv; IND. ENG. CHEM. 36 No. 6. 588-590 (1944). Studies in Selective Extraction and Adsorption. 1. Selective Solvents for Ethvlene Chlorohydrin: Ch. Weizmann, et al.; J, SOC. CHEM. IND. 67, 203-205, (May, 1948). The System Acetone-Water--1,1.2-Trichlorethane: R. E. Treybal, L. D. Weber, and J. F, Dalev; IND. ENG. CHEM. 38, No. 8, 817-821 (1946). Solvents for Extracting Nicotine From Aqueous Solutions: C. 0. Badgett; IND. ENG. CHEM. 42, No. 12, 2530-2531 (1950). Solvent Extraction of Oilseed: E. P. Cofield, Jr.; CHEMI CAL ENGINEERING. 127-140, (January, 1951). OTHER USES Use of Ethylene Dichloride in Lacquer Formulations: R. B. Frazier, E. W. Reid; IND, ENG. CHEM. 22, 604 (June, 1930). A New Preparation and Some Reactions of Di-(B-Chlorethyl) Sulfate: C. M. Suter, P. B. Evans; J. AM. CHEM. SOC. 60, 536 (March, 1938). The Efficacy of n-Butyl Chloride for the Removal of Intestinal Nematodes, Especially Whipworms, From Dogs: P. D. Harwood, et al.; THE NORTH AMERICAN VETERINARIAN, 21, No. 1, (January, 1940). Synthesis of Taurine and n-Methyltaurine: J, W. Schick and E. F. Degering; IND. ENG, CHEM. 39, No. 7. 906-909 (1947). Polvsulfide Liquid Polymers: J. S. Jorczak and E. M. Fettes; IND. ENG. CHEM. 43, No. 2, 324-328 (1951). Chemically Modified Wools of Enhanced Stability: W. B. Geiger et al; IND. ENG. CHEM., 34, 1398 (1942). Note Upon the Toxicity of Ethylene Chlorhydrin by Skin Absorption: H. F. Smvth, Jr., C. P. Carpenter; J. IND. HYG. TOXICOL. 27, (3) 93 (March, 1945). Reaction of Butyl Chloride with Methyl Amine: 0. Westphal and D. Jerchel; BER 73B, 1002-11 (1940). API Toxicological Review, B.B'-Dichlorethyl Ether (Chlorex), AMERICAN PETROLEUM INSTITUTE, Dept, of Safety, New York 20, N. Y., (March, 1948). The General Theory of the Wurtz Reaction showing Reaction of Amylsodium with Butyl and other Chlorides: A. A. Morton, J, B. Davidson, and B. L. Hakan; JOUR. AMER. CHEM. SOC. 64, 2242-7 (1942). Toxicological Studies of Compounds Investigated For Use as Inhibitors of Biological Processes. II. Toxicity of Reaction of Butyl Chloride with Toluene and with Ethylene Chlorohvdrin: A, M. Ambrose; ARCH. IND. Benzene: J. H. Simmons and H. Hart; JOUR. AMER. HYG. OCCUPATIONAL MED. 2, 591-597, (November, CHEM. SOC., 66, 1309-1312 (1944). 1950). Si 49297 oAS"ubject vc, - `-A'Tl AL: 42 4th Judic ^1 ; ve Order Uiotrict Cour No. Butyl Chloride Exchange? Chlorine with Aluminum Chloride: C. W, Wallace and J. E. Willard; JOUR. AMER. CHEM. SOC., 72, 5275-5281 (1950). Preparation of Butvlin Chlorides: K. C. Eberly. et al. ito Firestone Tire and Rubber Co.). U. S. PATENT 2.560,042 (1951). Butyl Amine from Butyl Chloride and Ammonia: H. F. Oxley, E. B. Thomas, and F. S. Nichols (to Celanese Corp. of America); U. S. PATENT 2,550,020 (1951). Sulfonated Detergents from Naphthalene, Butyl Chlo ride. Zinc Chloride, and Zinc Oxide: C. Amanov; FRENCH PATENTS 971,988 and 971,989 (1951). Toluene, Sodium, Butyl Chloride, and Chlorotriethoxysilane Reacted to Give Crude Butyltriethoxysilane: K. Hiratsuka; JAPANESE PATENT 5330 (1951). Butyl Chloride Used As a Solubilizing Agent in Lubri cating Oil: W. T. Stewart and A. Goldsmith (to California Research Corp.) U. S. PATENT 2.620,309 (1952). Chemical and Biological Studies of 1,2-Dichlorethane in Wheat: S. Dzierzgowski and B. Roczniki; PANSTWOWEGO BAKLADU HIG., 3, 361-369 (1952). The Effect of Butyl Chloride on the Polymerization of Stvrene: R, A. Gregg and F. R. Mavo; JOUR. AMER. CHEM. SOC. 75, 3530-3 (1953). Dibutylin Dichloride from Butyl Chloride, Stannic Chloride and Sodium: H. J. Passino (to Metal and Thermit Co.); U. S. PATENT 2,665,286 (1954). A Copolymer of Vinyl Pyridine and Acrylonitrile is Reacted with Butyl Chloride to Obtain Better Dying Properties: G. E. Ham (to Chemstrand Corp.); U. S. PATENT 2,676,952 (1954). Nitrogen-Containing Condensation Products Having Sur face-Active Properties (condensation of dichlorethyfether with amines): H. Krzikalla, K. Scholler, W. Pannivitz and H. Denner (to Badishe Anilin and Soda Fabrik); GERMAN PATENT 767,843 (January 18, 1954). The Application of Some Anthelmintics in Veterinary Practice (including butvl chloride): R. B. Griffiths; JOUR. PHARM. AND PHARMACOL.. 6, 921-943 (1954). Sized Alkaline Paper (condensation product ot epichlorhvdrin and a higher aliphatic amine): W. F. Rey nolds, Jr. (to American Cvanamid Co.); U, S. PATENT 2.694,629 (November 16, 1954). Sizing Glass Filaments (reaction product of epichlorhvdrin and octadecyl amine): J. C. Pullman and W. F. Reynolds. Jr. (to American Cyanamid Co.) U. S. PATENT 2,694,655 (November 18, 1954). Polyaminopolyureas (derived from alkvlenepolvamines, propylene dichloride, and urea); R. S. Yost and R, W. Auten (to Rohm and Haas Co.); U. S. PATENT 2.696,504 (1954). Ion Exchange Resins Containing Quaternary Ammonium Hydroxide Groups (dichlorethane is used): C. F. D'Alelio (to KoppeTs Company); U. S. PATENTS 2,697,079 and 2,697,080 (December 14, 1954). t Etherification of Starch (with ethylene chlorhydrin to make a textile thickener, printing gum, or a binder for molding sand) M. A. Staerkle and E. Meier (to Blattman and Co.) U. S. PATENT 2,698,936 (Jan. 4, 1955). Paper-Sized with a Polymerized Alkylene Imine (epichtorhydrin is used): C. G. Landes and W. F. Reynolds, Jr. (to American Cyanamid Co.) U. S. PATENT 2,698,793 (January 4, 1955). Nonflammable Paint Strippers 1. Relative Efficiencies of Chlorinated Solvents ana Binary Solutions (dichlorethane is used in a paint stripper) B, Berkeley, D. Schoenholz, and J. R. Sheehy; PROC. CHEM. SPECIALTIES MFRS. ASSOC., pages 29-37, (May, 1955). Water-Resistant Mineral Wool (using water-soluble con densation product of a fatty amine and epichlorhydrin) C. G. Landes (to American Cyanamid Co.); U. S. PATENT 2,714,746 (August 2, 1955), ANALYSIS AND HANDLING Simultaneous Determination of Ethylene and Propylene Chlorohydrins. W. A. Cannon; BIBLIOG. ANAL. CHEM. 22, 928-929 (July, 1950). Chemical Safetv Data Sheet SD-18, Ethylene Dichloride; MANUFACTURING CHEMISTS' ASSOC., Washington 5, D. C. Nothing contained herein shall be construed to constitute a permission or recom mendation to practice any invention covered by any patent without a license from the patent owner. OTHER AVAILABLE LITERATURE 0<G0 In addition to this booklet, literature is available on more than 400 synthetic organic chemicals which Union Carbide Chemicals Company produces. Separate booklets and reprints about any specific group of chemicals or individual chemicals may interest you. Your inquiry is invited. C" u ,'Ov ," TV \ A 0< 9^ 98 -a> -. 'S 7p 'V V A 43 A UNION CARBIDE CHEMICALS COMPANY Produces over 40% ALCOHOLS Amyl Alcohol, Primary (mixed isomers) Anhydrol Proprietary Solvent Butanol iso-Decanol Diisobutyl Carbinol Ethanol (All Formulas) 2-Ethylbutanol 2-Ethylhexanol Heptadecanol 1- Hexanol Isobutanol Isopropanol Methanol Methyl Amyl Alcohol 2- Methyl-l-Pentanol Synasol Proprietary Solvent Tetradecanol 2,6,8-Trimethyl*4-Nonanol Undecanol (3, 9-diethyl-6- tridecanol) ALDEHYDES Acetaldehyde Acetaldol Acrolein Acrolein Dimer (2-formyl-3,4- dihydro-2H-pyran) Butyraldehyde Crotonaldehyde Formaldehyde Glutaraldehyde Glyoxal 2-Hydroxyadipaldehyde Isobutyraldehyde Methacrolein Paraldehyde Propionaldehyde Pyruvic Aldehyde GLYCOLS AND TRIOLS Carboseal Anti-Leak Diethylene Glycol Dipropylene Glycol 2,2-Diethyl-l,3-Propanadiol 2-Ethyl-2-Butyl-l,3-Propanediol Ethylene Glycol 2-Ethyl-l,3-Hexanediol 44 1,2,6-Hexanetriol Hexylene Glycol 1,5-Pentanediol Propylene Glycol Triethylene Glycol POLYALKYLENE GLYCOLS Carbowax Polyethylene Glycols 200, 300, 400, and 600 (liquids) Carbowax Polyethylene Glycols 1000, 1500, 1540, 4000, 6000 and 20M (sblids) Carbowax Methoxy Polyethylene Glycols 350, 550, and 750 Polypropvlene Glycols 150, 425, 1025, and 2025 "Niox" Polyols "UCON" FLUIDS AND LUBRICANTS "CELLOSIZE" HYDROXYETHYl CELLULOSE "POLYOX" WATER-SOLUBLE RESINS SOLVENT RECOVERY PLANTS AND "COLUMBIA" ACTIVATED CARBON ETHERS AND OXIDES Butyl Ether Carboxide Fumigant Chlorex Solvent Dibutyl Carbitol Dibutyl Cellosolve Dicblorethyl Ether Dichlorisopropyl Ether Diethyl Carbitol 1,4-Dioxane 2-Ethoxy-3,4-Dihydro-2H* Pyran Ethylene Oxide Ethyl Ether Hexyl Ether Isopropyl Ether Propylene Oxide Vinyi Ethers "FLEXOL" PLASTICIZERS Flexol Plasticizer A-26 Flexol Plasticizer B-400 Flexol Plasticizer CC-55 Flexol Plasticizer DOP Flexol Plasticizer 3G11 Flexol Plasticizer 3GO Flexol Plasticizer 4GO Flexol Plasticizer 8N8 Flexol Plasticizer R-2II Flexol Plasticizer TOF Flexol Plasticizer 426 Flexol Plasticizer 810 Flexol Plasticizer 10-10 Flexol Plasticizer 10-A ANHYDRIDES Acetic Anhydride Butyric Anhydride Propionic Anhydride Allylidene Diacetate Amyl Acetate, Primary (mixed isomers) Butyl Acetate Butyl Acrylate Butyl Carbitol Acetate Butyl Cellosolve Acetate Carbitol Acetate Cellosolve Acetate Decyl Acrylate Di(2-Ethylhexyl) Maleate Diethyl Maleate Diethyl Succinate Diethyl Sulfate Ethyl Acetate Ethyl Acetoacetate Ethylene Carbonate Ethyl Formate 2-Ethylhexyl Acetate Ethyl Silicates Glycol Diacetate Isobutyl Acetate Isopropyl Acetate Methoxytriglycol Acetate Methyl Amyl Acetate Methyl Cellosolve Acetate Propylene Carbonate ^ Ov.' o order Subjo; of 14th Judic la 1 Diotr let Ho. 91-1145 Court SL 049299 CSynthetic Organic Chemicals Sucrose Octa Acetate Tetraethyl Orthosilicate Vinvl Acetate METALLIC SALTS Niaproof Aluminum Acetate, Basic Aluminum Formo Acetate Copper Acetate (Cupric) Potassium Acetate Sodium Acetate Sodium Diacetate Zinc Acetate KETONES Acetone Diacetone Alcohol Diethyl Ketone Diisobutyl Ketone Ethyl Butyl Ketone Isobutyl Heptyl Ketone (2,6, 8-trimethyl-4-nonanone) %iophorone Mesityl Oxide Methyl Acetone, Synthetic Methyl n-Amyl Ketone Methyl Ethyl Ketone Methyl Isobutyl Ketone Methyl Propyl Ketone 2,4-Pentanedione ACETALS ACIDS Acetic Acid Acrylic Acid (glacial and 30% aqueous solutions) Butyric Acid Crotonic Acid 2-Ethylbutyric Acid 2-Ethylhexoic Acid 2,4-Hexadienoic Acid GLYCOL-ETHERS l-Butoxyethoxy-2 -Propanol Butyl Carbitol utyl Cellosolve arbitol Solvent Cellosolve Solvent Ethoxytriglycol Hexyl Carbitol Hexyl Cellosolve Methoxytriglycol Methyl Carbitol Methyl Cellosolve NITROGEN COMPOUNDS Butyl Benzoate Ethylbenzene aZp/ia-Methvlbenzyl Ether 2-Methvl-5-Ethyl Pyridine Phenol (U.S.P.) Phenyl Methyl Carbinol N-Phenyl Morpholine Picolinea Styrene Acetonitrile N-Acetyl Ethanolamine Acrylonitrile / Amine 220 N-Aminoethyl Ethanolamine N-Aminoethyl Piperazine Butyl Amine Dibutyl Amine Diethanolamine Diethyl Amine Diethylamino Propylamine Diethylene Triamine N,N-Diethyl Ethanolamine Di(2-Ethylhexyl) Amine Diisopropanolamine Diisopropyl Amine Dimethylamino Propylamine Dimethyl Ethanolamine Ethyl Amine Ethylene Cyanohydrin Ethylene Diamine 2-Ethylhexyl Amine N-Ethyl Morpholine N-Hydroxyethyl Piperazine Isopropyl Amine N-Methyl Diethanolamine N-Methyl Piperazine Mixed Isopropanolamine Monoethanolamine Monoisopropanolamine Morpholine Piperazine ^Propylene Diamine Tetraethylene Pentamine Triethanolamine Triethyl Amine Triethylene Tetramine Triisopropanolamine ARYL CHEMICALS Acetoacet-Arylamides Acetophenone Aryl Ethanolamines COiE Subject: * SULFUR COMPOUNDS Kromfax Solvent Mercaptoethanol "TERGITOl" SURFACE ACTIVE AGENTS HYDROCARBONS "CRAG" AGRICULTURAL CHEMICALS DYNEL ACRYLIC FIBERS "CARBOSEAL" ANTI.LEAK INDUSTRIAL FUMIGANTS SORBIC, FUNGISTAT FOR FOODS "MORLEX" CORROSION INHIBITORS MONOMERS Arcylic Acid and Esters Acrylic Acid (glacial and 30% aqueous solutions) Ethyl Acrylate 2-Ethylhexyl Acrylate Butyl Acrylate Vinyl Esters Vinyl Acetate Vinyl Butyrate Vinyl 2-Ethylhexoate Vinyl Propionate Maleic Esters Diethylhexyl Maleate Diethyl Maleate Vinyl Ethers Vinyl Butyl Ether Vinyl 2-Chlorethyl Ether T Vinyl Ethyl Ether Order 'nutrict coutt SL r 49300 I144 tb no. 91 -1145 UNION CARBIDE CHEMICALS COMPANY UNION DIVISION OF IcanbiocI CORPORATION 30 East 42nd Stre t, New York 17, New York SALES OFFICES: Albany 7, N. Y..................... 90 State St...................................................Albany 5-3507 Atlanta 3, Ga........................ 41 Marietta St., N. W............................. JAckson 4-5081 Baltimore 1. Md................... 210 North Charles St............................. SAratoga 7-7365 Boston 94, Mass................... 300 1st Ave., Needham Hts....................Hlllcrest 4-5400 Buffalo 2, N. Y....................1812 Liberty Bank Building................................ MAdison6932 Charlotte 2, N. C................. 112 South Tryon St................................FRanklin 5-3383 Chicago 1, 111........................ 230 North Michigan Ave....................... Financial 6-3300 Cincinnati 6, Ohio...............2506 May St.................................................. 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EXpress 1-3800 St. Louis 5, Mo.................... 10 South Brentwood Blvd..................... PArkview 6-0324 San Francisco 6, Calif........ 22 Battery St............................................... YUkon 2-1360 Seattle 4, Wash................... 3404 Fourth Ave., South......................................... MAin6247 Tulsa 24, Okla...................... 2901 South Harvard..............................Riverside 2-5524 MANUFACTURING PLANTS: Institute ........... Niagara Falls. . . Seadrift............ . . West Virginia , .New York . .Texas Whiting.......... South Charleston.. Texas Gty........... Torrance.............. .......... Indiana Warahou** Stookm In Principal Cltlaa .West Virginia .Texas . California IN CANADA: Carbide Chemicals Company Division of Union Carbide Canada Limited Calgary, Alberta................... 215 10th Avenue, West............................ AMhurst2-9546 Montreal 25, Quebec............ 1425.Mountain St.........................................Victor5-3174 Toronto 7, Ontario...............40 St. Qair Ave., East............................... WAlnut4-5461 OUTSIDE UNITED STATES AND CANADA: Union Carbide International Company Division of Union Carbide Corporation New York 17, N. Y,, U.S.A.. .30 East 42nd St.......................MUrray Hill 7-8000 Printed In U.S.A. CT., Subject i'..' -' V1 of 14 th JuclicL Ko : .. - M769C ccur1 SL 049301