Document jgbYGMJyjvv3VkvNpmZ57gYxR

826 C1IL0UINF COMPOUNDS, ORGANIC bciir'.ul.nehloi idc may be used to prepare benzoic acid ('/..) (N,0) '/'lie promi nence of benzol riebloridc, however, results from its extrusive use in (hr field of dyes. At one lime if was used extensively in the produefion of Malaehitr (hr-m hut has pinee Keen replaced to some extent by benzaldehyde. However, the dye industry is still the l.-ir^est ron.,;timrr. The dyes produced from benzolrieldoride appear in Table m (2). TAHI-li 111. I>ycn Mnmifnclurotl from Ihuizolrlrliliu-ide. Cln ol ilyp TriphcnylmHhniio Niiiidiciic Quinoline Aiilliini|ninc>iir Common nmno Mnlncliitn Green HoMWflitlO Quinoline Red AliV.iii in Yellow A C.l. No. 057 745 805 1014 Ollier cr>fii(.>>M''n11 AT'V-HiinrllivkuiiUiu' Wi-J)i)Hhyl.'oi]inoj)li*'iifil Quinaldino, i.so(|u:n<))iii(_' byropaflol bibliography for benzyl Chloride, clc. (1) lHal lit rill, *1111 nh, Vnl. V, |ip. 792-300; Isl. fcuppl., Vol. V, pp. 151 52. (2) Colnur Imlcx, 1021; Suppl., 1923. (3) Davcy, W,, /ms/. Petroleum, 31, 73 PS (1915). . (4) Giiisliuo'i A., ft ol., Iml. Km}. Cftcm., 38, 178- 85 (1015). (4n) Jlunlrrss, K. 11., Orjniiir Clifarixc Ominumh, Wiley, N.V., 1018, |>|>. 1100-SO, R5G 01. 879 S3, (fr) Urk, G., Her., 74H, l.%8 74 (1011). (5rt) Urif, l\it. 310,010 (June 20, J02D), N. Hrnurll and \V. C. Sprout (lo linpniid Cluunioal Irulun. hits). (0) blit. Pat. 37S,3fifi (Aiir. 10, 1032), T. 1). Wheeler (to Jmpt.-i >;d Chemical Industrieo). (7) U.S. Tat. 721,Wil (March 3, 1903), 1,. Man kwald. (8) U.S. I'nt, 1,057,153 (OH. 13, 1025), A. Geou-c (to Mnlhimm Alkali Woiks). (ft) \1.S. bat. 1,591,245 (July G, 1020), K. V). Slockclhack (lo Muthicson Alkali Works). (10) U.S. l'at. 2,211,798 (Aur. 20, 1040), 11. W. Story ami W. Fuller (lo Sornny. Vacuum Oil Co.). (11) U.S. but. 2,221,832 (Nov. 1ft, IftlO), 1>. T. ltfigrnhcrR (lo National Oil Products Co.). (12) U.S. J'at. 2,379.291 (May 15, 1945), V. J, Sown. (13) U.S. I*nt. 2,383.775 (Aur, 28, 1945), W. R Craig nml W. V. Hester (to Ul.m & Haas Co.). H. I/. Ci-auk A\i) C. b. Nianifi Chlorlnaled Diphenyls and Hclalcd Compounds. The Aroclors (trade-mark) are chemically inert materials prepared by (he ehlorinAtioii of diphenyl (biphenyl) or terphenyl or more complex polyphonyK usually with out separation of the chlorinated products into individual compounds. The form nml appearance vary from mobile oily liquids to fine while ery.stals and hard non crystalline resins. because of the many forms and properties, those products have found appliealions in many diverse fields ns in electrical insulation, nonflammable hydinulic mediums, lubricants for use at hiph temperatures and pressures, and also as constituent of adhesives, plastics, lacquers, paints, and varnishes, Commercial manufacture of the first, members of the Aroelor series was stal led in J02I), and the ot her Aroclors were developed soon afterwards. Physical nml Chemical Properties Since Aroclors arc chemically inert except under drastic conditions, they me of interest chiefly because of their physical properties (3). All Aroclors arc insoluble in V., MGAS 077871 7 1 8 L 1 0 SNOW IZ fi 31 M VD U O `U (/M n 0 ,m '0 3 H M IU 01113 TABLE I. General Properties of Some Aroclors. F___ *nd coior ' Sp r-S Di'tiVfttioa F!j*h 1 ^c1'* pCT.l.* c. Po-jr Aroclor 1221 Aroclor 1232 Aroclor 1242 Aroclor 1243 Aroclor 1Z34 Aroclor 1200 Aroclor 1202 Colorless mobile oil 1.177-1.1ST 275-320 141-150 170 Almost colorless 1.2132-1.272 mobile oil Almost colorless 1.378-1.3SS mobile oil , Yellow-tinted 1.447-1.457 mobile oil - Li^lit yellow vis 1.533-1.5,8 cous oil Soft yelluw sticky , 1.01S-I.G29 resin . Li"!,: >v!!ow sticky 1. 40-1.053 200-325 , 152-154 325-300 , 17G-1S0 340-375 , 193-19G 355-390 , None 3S5-420 400-430 | None i ( None 233 334 None None None None Crystals at 1C. --35.5 -19.0 ~7 10 31 37 Sopfol-emn.iwnc c. " -- -- " -- - "" 1.G17-1.G1S At 37.3'C. 40-42 y.'-re. At ?S VsC. 30-31 . 1.620-1.C22 47-50 31-32 1.G27-1.629 $0-93 34--35 1.630-1.631 1S5-2K) : 36-37 1.639-1.641 1SC0-2.50O j 44-4S 1.647-1 649 1.6501-1.6517 -- 72-73 - ; 90-103 Aroclor 12GS-' Opaque yellow brittle resin 1.S04-1.SU -35-450 Nooe i' None - - Aroclor 1270* White crystalline oovvJer 1.044-1.000 450-4GO j None None -- -- Aroclor HCS Transparent yellow i.712-1.723 230-320, None brittle resin None -- 60-66 1.5G4-1.667 Aroclor 5442 Transparent yellow 1.432-1.447 215-300, | 247 sticky resin > 350 46 45-50 -- Aroclor 5400 Yellow transparent . 1.740-1.745 2S0-33o None None -- 100-105.5 1.060-1.GG5 -: - "-- -- : 90-150 ' (at 130*C.) 300-400 --- Aroclor 25G5 3rown-b!ac< opaq-ie resiri 1.724-1.740 - , None None - 66-72 - -, - A.S.T.M. D20-30. * Cleveland open wp. `A.S.T.M. D07-47. - A.S.T.M. 2S-42T. Saybolt Universal, A.S.T.M. DSS-44. ' Hold point on solidification, 135-ICO'C. Hold point 0:1 solidification, 249-300"C. m CHLORINE COMPOUNDS, ORGANIC water, but the oils and resins are readily soluble in most, of I ho rmimmit ojganir sob fniand drying oils. The bard crystalline maI ('rials arc in general less soluble I liaii I lie mb and resin*. The Aroclors arc permanently l.lirrnmpla.sl ic and may b<> n-po;i(<<l)v indit'd and cooled without, undergoing condcnsalion or permanent hardening. Mov|, of the common metals and alloys have excellent resistance lo lbe Aroclors even at devatoil temperatures. However, copper and some of the copper alloys are affected lo a limited extent, and show penetration rates between 0.0011 and 0,011 in. per yea/-. Many plastic materials of const.ruction me attacked by the Aroclors, The peroral properties of tbe more important praties of the Aroclors are shown in Table ], and Table II shows the electrical properties of those Aroclors that have found application in thoolwlricnl field. ' I'roj.frty TAUL1S II. F.lcctrlral Properties of Some Aroclors. '.'S'." *,JCW lliclerlric cunslanl. (it 100 *(/. nml 1000 eyelets* KesUlivily, ohmem., ftt. iooac:. nml 500 volUd.e. I Heleetvic Mreiipth,* W. Power fnotor, % nt lOO'C. ami 1000 cyftlTM 4.0 4.0 4.0 ' 4 1-1 3 3038 4y Above Above Above Above 600 X 101 600 X 10* 500 X 10* 500 X in* Aftovc 35 Above 35 HcIimv 0.1 Ibtow 0.1 JVIotv 0.1 IJvl.nv 0 J A.S.T.M. 1)150 * A.S.T.M. HI 10-14 using a 0.100-in pftp- Manufacture The pure compounds formed by the chlorination of diphenyl, terphenyl, or Ihe more, complex polypbcnyls are. crystalline solids, some of which have very high melting points (Jl). However, mixtures conlnining a number of such compounds arc either liquids or nonerystallino resins. Chlorination of aromatic hydrocarbons to various levels not only gives several isomers of the same chlorine content but also gives appreciable proportions of the isomers of compounds of higher and lower chlorine con tents (17,23). At any given level of chlorine content, batch chlorination gives liar login's! proportion of compounds corresponding ill composition lo the average chloi iue content, while single-stage continuous chlorination gives the lowest, proportion of such compounds. As the number of stages is increased, midlist age con I humus chlorination gives compositions approaching those given by batch chlorinalion. The proportion of the various isomers and of compounds of higher and lower chlorine contents Ilian the average is also influenced by such fa cl ur.< as temperature, quantity and kind of catalyst employed, degree and type of ngitai ion, and rale of admission of I hr chlorine. hatch chlorination has been found most, suitable for the manufaelure of the Aruelors (23,2'1). The chlorinntms arc cylindrical steel towers 3 ft , in diameter and IS ((. high, which arc equipped with rliloriiie distributors at the bottom and with coils for beating and cooling tbe material undergoing reaction. Tumps provide agitation by MGNS 077873 CHLOMNK COMPOUNDS, ORGANIC H2n eirentaling I In* chnrgr. The lower half of llic rliloiiim lurs is filled wit.fi inm linoihi'.- , which have been burned I'm1 (if oil mid Minis) tin*. In (irinmii prmMiee, (lie rfilonn;i11*r,s are agilalcd 11),!)())I-hi er lead-lined vessels, and ferric, chloride is used as I he eatalysl, insiead of iron (innings. Killeen kilograms of ferric chloride is hm-cI fin niili cliaige of 0000 kilograms (Id). Haw Materials. The raw material used depends mi the grade of Arochir to lie produced; anhydrous chlorine is used as the chlorinating agent in all eases. In gennal it can he said (hat diphenyl alone gives liquid or soft sticky noneryslalline A i odors up to a chlorine content of low-melting resinous Aroelors between 00% and 0fi% chlorine content, and partly crystalline or crystalline Aroelors of much higher melting points at- chlorine contents above 00% (2d). In tin: ease of products that are solid at ordinary temperatures, the higher the proportion of lorphenyis or more complex poly- phetiyls in the mixture before chlorination, the higher the softening point and the less the crystallizing tendency of tho chlorinated product after distillation. For those Aroelors (hat are solid or partly crystalline at room temperature, the higher the chlorine content, the higher the softening point and the grealcr the tendency of the material lb crystallize (21). ' Preparation of Crude Aroelors. For the manufacture of any given grade of Aroclor, the oldurimilor is charged with (lie proper raw material or mixture of raw materials to give the desired product, and in an amount sufficient to cover the catalyst bed and to permit circulation. Then the flow of vaporized chlorine is started and the charge is circulated with tire pump. Throughout the chlorination, the temperature is kept well above the melting point of the mixture, but below lfi0C., to avoid excessive sublimation and plugging of I be line discharging the hydrogen chloride produced by lire chlorination. Samples are withdrawn for examination from time to time until the desired chlorine content has been reached. At the lower chlorine contents, .specificgravity determinations arc Used to determine the composition. After the product lias become too viscous or has reached loo high a melting point for convenient determina tion of tho specific gravity with a hydrometer at temperatures below 100C., the de gree of eblorinalion is determined by measuring tlic hold point in temperature as the material crystallizes, or by the ball-nml-ring softening-point test (8). The time re quired for chlorination is 12- 30 hr., depending upon the chlorine content of the prod uct. The anhydrous hydrogen chloride, which is evolved during tho chlorinalions, is absorbed in water in equipment of conventional design. Distillation of Crude l'roduels. Although the crude products find some applica tions, for most purposes further purification is necessary to remove the color and the traces of hyd mgen chloride and ferric chloride (13,23,24). The methods of purification are somewhat different for tho different types of Aroelors. The high-melting solid products arr distilled in retorts at atmospheric pressure and the distillate is flaked on chilled rolls. The liquid and resinous Aroelors are Mil .'il. nil elevated temperature and blown with dried air for several hours. Then a few lentils of one per ecul of lime or sodium hydroxide is stirred with the material to reaet wi(h any remaining hydro gen chloride or ferric, chloride. This is followed by butch distillation. Complete dis tillation and mixing of the distillate is necessary in order to obtain uniform material of the desired eomposit ion. If increased electrical resistivity is desired, the material is stirred at an elevated HONS 077874 CULOKtNR COMPOUNDS, OHCANIC temperature with n few tenths of a per cent of well-dried fiillcr's carl li and I lien (ill end through poper (J3,2b). Containers mu! Shipping The )i(|tii(l Arorlors arc parked ami shipped in galvanized steel drums nr in lank cars constructed of nonrust mg metals such as aluminum or fin-coated metal. The resinous Aiuclots me packed and shipped in open-lop galvanized steel drums. The high-melting solid Aroe.Iors are packed and shipped in wooden barrels. The railroad shipping classification is Itcsin Synthetic N.O.I.lt.N. Health and Safely Faclors The conventional safeguards must ho taken to protect personnel from the poison ous cfiVels of chlorine. Kxporimonlnl work on animals has indicated that prolonged exposure fo Arocfor vapor evolved at- high temperature or repeated oral ingMion of Aroclor will lead to systemic to.xie effects. Jlepeatrd bodily contact with liquid Arorlors my lead loan acne-form skin eruption, Jn the manufacture or use of Arodorx, untoward eJTeels on personnel arc prevented by draft ventilation to control the vapors rvolved nt high temperatures, together with the vise of suitable garments to prevent extensive and repeated bodily contact with the liquid products (3). Uses JClcdrical Applications, All of the uses of the Arorlors depend on their chemical stability and their physical properties, which may bo varied to suit the specific applieslion. One very important use is nr. dielectric mediums in such applications as nils for transformers ami as impregnanis for capacitors ami condensers (10,11,12,15,18,21,25). Aroclors, used either alone or in blends with other materials such as tnchlorohciizene, meet- the need for a nonflammable dielectric liquid with a high resistivity, a high dielec tric strength, nmi a relatively high dieleelrie constant in relation to a very low power factor. The fact that the dielectric constant is higher limn that of hydrocarbon oils and is morr nearly rqnnl to that of the so id insulation materials, such ns paper, results in a reduction of electrical .strains, hy substituting Aroclors, or mixtures of Arorlors with Iricldorobcnzcne, for hydrocarbon oils, it has been possible to redesign equipment with a great reduel ion in size for the same eapaeity ami voltage. At the same time the fire hazards have been eliminated. Other important electrical applications for Aroclors arc as imprognmds for col ton or asbestos-fiber insulation (22), as constituents of asphalt-base wirc-impicgn.ifmg compounds, and as plasticizers in wire-coaling compounds, particularly thn>o contain ing neoprene, rubber, or combinations of polyvinyl chloride, ethyl cellulose, and poly vinyl butyral (30 33). Also, Aroclors arc employed as sealing mediums for electrical insulators nod as impregnants for carbon radio resistors to reduce the influence of moisture. Plastics, f.nc<picrs, Paints, awl Varnishes, The Aroclors are compatible with most of the common plastic materials and resins and are soluble in paiul mid varnidi oils (3). In combination with asphalt, ethyl cellulose, chlorinated rubber, J'bolile S-5, or other plastic materials, they are used extensively in protective coatings for wood, /octal, and concrete (3,5,0,20,28). In combination with Uicroyl phosphate or dioclyl phtbnlnte they arc coplasticizcrs for polyvinyl chloride compositions (4). HGNS 077675 CULOIUNIi COMl'OUNOS, ORGANIC H.U In fmints am! varnishes (ho hard resinous Ame.lnrs are used (n imparl inrrr-a.sr-d hardness In the films, and tin: sufler resins are used lu give flexibility. The n.li- of i.fio Amelnr is similar In I lull- of (lie oil, cxrrpt fur tin; fuel. Chat il. dues not. oxidize and lose its flexibility on aging. Jo nitroeelhilose lacquers, Aroclors ;in: employed eit her alone or in rninhinatinn with oilier plasticizers and resins Co imparl, increased wrsl.her ie- sislanee, luster, adhesion, and 'decreased burning rale Id,10). The hard, white, crystalline Aroelurs of high melting point, are useful as pigments with the various plastics .1 flliesins. The resinous A roc tors are used in synthdie atlhesi ve eomposit ions m comhinalion with sueh base uui/rriitls as jmly vfuyl aeelale, clhyl eelhdu>e, cfiluriimfed millin', polyvinyl hutyral, isnprene styrene copolymer, and polyisolmtylene. Lubricants. Aroelurs 12*18 and 1254 find application as lubricants under extreme conditions such as highly oxidizing conditions, high temperatures, extreme pressures, or submerged local ions. The use of Aroelor ns (be internal lubricant for high-pie.-Mirc air compressors eliminates tho explosion hazards in this operation (1,2). The mate rials arc used also as noncombustiblc lubricants for regulating the steam valves on high-pressure turbines, and in rolling aluminum sheets. Mixtures with other oils to form iieavier-than-watcr lubricants are used in submerged locations, such as bridge rollers. Lubricants for extreme pressures are made by adding up L>% of Aroelor lo petroleum hydrocarbon oils. 'i'he liquid Aroelurs are employed as nonflammable hydraulic mediums for trans mission of pressure or volume variations. One such application is in die-easting operations with aluminum or zinc alloys, where the Aroclors replace hydrocarbon oils. The ad vantages arc absence of fire hazards when lines break, and the fact that con densed water docs not settle, in the storage tanks and cause corrosion of the equipment. Another use is as the expansion medium in thermostats. Aroclors 12<12, 1248, and 1254 have been found to give excellent service as circulating liquid hcut-transjcr medium for temperatures up to 325C. Good circulation and well-designed heating systems arc necessary to prevent local overheating (3). Carnauba wax may be extended by blending it with Aroclors in combination with cercsin and paraffin (7,19). Satisfactory waxes and polishes arc prepared without the use of carnauoa wax by blending ouricuiy (licuri) wax with Aroclors, cercsin, and paraffin. Aroclors arc ingredients of many firc-rcsislanl compositions, Tire-retarding paints usually contain antimony oxide or barium sulfate in addition lo the Aroelor. In making fireproof fiberboard, emulsified Aroclors arc added to the fiber stock (27). Modifying waxes arc added to the Aroelor in the preparation of Icxtiic-conting ma terials, Miscellaneous Applications. In addition lo the uses listed above, Aroclors am in gredients of some scaling compounds for use will* wood or canvas to give protection against moisture, mildew, or attacks of organisms. Some calking compounds and powdered metal pastes contain Aroclors. Some soil-poison and wood-preserving com positions contain Aroclors as an active ingredient. Bibliography for Chlorinated Diphenyls (1) Andrews, H. W., nod Kipp, K M , Am. Mm-hiniA, SS. 107 (1011). (2) Aroclur Incombustible Lubricants Usc/l in llijh-l'rcssure Compressors (Technical Bull. P-128), Mumtnnto Chiaiwvi) Co., SL Louis, Mo., 10IS. (3) ArocJors (Application Data Bull. P-115), Monsanto Chemical Co,, Si. loum, Mo. HONS 073836 M2 CUL01UM COMPOUNDS. ORGANIC (o Armtm* ('<,-)'\olin;<r Jor J^lyriuyl n.hri./c (Teishoicid Hull. l'-I.Jl), MouK:,m. Cl.,-,,,;, ;,| c,,, si. Mo., in is. (5) h* Use,I in in/,:,/ Uuhlur (Teclini-.nl Moll. 1`-12-1), M,nin.inl,i Clirtnicril Cm,, St. 1 .intis, Mo., 1`.) IS. (ft) A un-ton* <tx C.m din /WifeS-5 (Tcchnii nl Mull. Munwotln Chemical CV, Si 1,,mh,,, Mr,., JOtS. (7) ,lr,n7,,,s ,is IIn H.ittml ,u Suhsfiltifc Cm niiiilm IVn.r (Trclum :J Mull. J'-KIl'/, M'min.uiIm Chrniua! O'.. Si. fornix, Mo., 19-IS. (8) A.S.T.M., Sfamhnh, HM, Tart JH-A, Nwimlallii: Malc.-inls: K28 42T. (9) Mrovrotr, II. W., lUunt TcrUnoi, 2, 25-27 (1937). (10) Ruiiihnn, 1*. JI-, .'toil Maunder, S.6Y. IChr. Hen., 42, 230-39 (1930). (M) Chirk, K, M,, Tnuts. Hlcvtrochcin. Stir., 05, 51) 71 (1931). (12) Clark, V'. M../W. Hntt. Chen., 20,608 702 (1937). (K)) Fay, 3. W. J., Mini Hiclnrils, J. II., ``IinjuiunnnU Used in German I'npcr Capacitors," Oj/i>c 7VrA. ScuyYc* Hc,,t , l'U.7f;S50 (1917); lltOS I'innl Hr,,l.. No. R93. (l i) (kmtuer, II. A., and Sword, Cl. Cl., A6il/. I'aiut Varnish fsuqncr A.oe., Nn'. Arc., C'rVc., No. 55, 100 03 (J93S). (15) .l.'ickson, W., I'mr. Kmj, Nor. (/.o/o/on), 4133, I5.S 66 ()0.'l5). (1ft) Jenkins, 1(. I,., nnl Foster, R. N., fri'l. Hug, Chew., 23, 1362 65 (103)). (17) MneMidlitt, R. H., 0,cm. Huff. Vrw**, 4>. No. 3, 183 (W (JIMS). (IX) Whdr, A. JI , and S. (V, 7. VranUin !nV., 216, ft35 11 (1933). (19) Worn), O. \\\, U.fa. Chemist, 19, No. 3, 09-10) (1918). (20) U.S. 1`ui. 1,812,732 (.lour 30, 1931), J. II. Voting (lo II. U. ltnherlson Ct.). (21) U S. I'nl. 1,836,1 SO (Dec. 15, 1931), C. R. McCullough :iml R. I,. Jenkins (lo Swtinn RcM-airli; ro:iMsi|;ucd lo Monsanto Chemical Co.). (22) U S. Tal. 1,863,1-17 (June H, I0;i2), .1, II. Young (to II. II. Rohertwm Co.). (23) U S. Tills. 1,892,397; -398 (Doc. 27, 1932), R. F. Jenkins (lo Sw.irnt Hew.-trel*; rcax-ngMed lo Monsanto Ohromnl Co.). . (21) U-S. R:il. I,SOI?,400 (I)<*<:. 27, 1932), R. I,. .Jenkins nod .1. A. Siknrski (to Swmm Hcscnrrh; reassigned (< MoijnumIo Chemical (lo.). {?&) U.S. Tal*. 1,5)31,373; -155 (Oct. 17, 1933), V. M. Clark (lo General Klrrtric Co.). (26) U.N. Tal. J,991,302 (March 12, 1935), V. M. Clark (In General Klcrlric Co.). (27) U.S. Tut. 2,030,653 (l-Ylt. 11, 1930). R, Cl. Quinn (lo International Taper Co,). (28) U.S. Tut. 2,01-1,605 (.June 10, 1930), W, Koch (lo Hercules Powder Co.). (29) U.S. Tut. 2,077,700 (April 20, 1937), K. Kline (to Du Toni). (30) U.S. Tat. 2,129,157 (Sept. 0, 1938), K. \Y. Tmefitmier nnd W. C. Wilson (lo Pyroxylin Product*). (31) U.S. Tat. 2,130,261 (Sept. 13, HISS), F. M. Clark noil J. H. Koenig (in General HJeeliic Co.). (32) U S. I'itl. 2,141,910 (Dec. 27, 193S), W. C. Ilnym.-m (lo General Klcrtric Co.), (33) U S. Tal. 2.1.58,281 (May 10; 1939), J. G. Ford nnd C. V. Hill (to \Vcslmr,li<ni!o Fleclric and Mttniifnelunng Co.). C. F. Ilooni Clilorionlcd Nnphllinlcoo.s. The chloiinati'd imphlimlcnos mo of inl.ciost from hoti the (celmieal and (fie purely v.eionlific points of view, 'l'lwy j\re of consitlernlilo impnilnnrr eominerriaily aim) find many uses in (lie clicioiral, ]>elroleum, eli'o.lricftl, nml related fields. On tmilinent willi c.lilorine, nnplttlmlene (1) forms two types of derivatives. In the nlisem'o of n (dtlorimition rjilolysl, mill il inn Hikes pluee m-ross the double bonds, for min;: kucIi (Irriviilivrs as nupliiludene dirlrloride (11) ami naphthalene letrncMovide (111). In the pi< s(nre of cat.ilysl.s .such as ferric chloride or iodine, siihHlilution occurs, pivin^ rise to moJiochloroii.'iplitlmlrne.s, mainly J-cJiloronaphlhalem' (IN'), as tire first step. On further chlorination fit higher temperatures, then is next formed a mixture of tli- HONS 077877