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M ontanto Technical Data Sheet ,
Febtuary 26, 1954
Monsanto Chemical Company-, Orgcnlc Chemicals Division, St. Louis 1, Mo.
AROCi.ORS*, f/fl-40*, 11U-2Q', PIIENYLCYCKOHEXANE, BICYCLOIIKXYI.
All of the above materials are Monsanto chemicals which can be of value in certain distillation problems. T hese materials are hit;!) boiling solvents |>os<assing good heat stability. The AROCLORS (a series of chlorinated polyphcnyls) are especially noted for their chemical inertness. The other chemicals may also serve as inert solvents. Consequently, these materials all find use as distillation aids where the lower boiling material is subject, to decomposition from localized overheating, and in ca<cs where distillation residues arc re>inous or solid materials which are difficult to dean out of the still pot. The Monsanto chemicals listed also find considerable application as inert media for many chemical reacimns
An example.of the value of such distillation aids is a case where a product distilling at about 78C. at 40 mm. Hg. was separated without fractionation from AROC/.OR 124? which, at the same pressure, boils a: 210'C. Another product boiling at 100-C. at 2 mm, Hg. required only moderate fi actional ion to separate it from A ROCLOR 1 242 boiling at 13SC. (at 2 mm. Hg.).
Which material to use in a given situation can be determined from the table of properties which appears on the next page. When reduced pressures are involved, further data may be obtained upon request.
AROCLOR products 1242, 1248, 1 254 and 1260 are liquids with progressively in
creasing boiling points. These liquids aa a stable heel in the still and allow ali of
the desired end product to be recovered. In cases where the distillation residue
normally tends to polymerize into gummy materials or to decompose into solids, th
liquid
compounds can be used to keep the residue as a free-flowing fluid
for easier removal. Also, by allowing better heat transfer in the fluid, excessive
decomposition and product loss can be minimized.
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In addition to the liquid ARQCLQR product?. Monsanto offers AROCI.OR 54r>0, a resinous solid which has been used to pla-ticize solid still residues to facilitate re moval. This resin cannot be recovered and is discarded with the residue. From 25ck to 30% of A ROCLOR 54K), based on total residue weight, will satisfactorily plas ticize most such residues.
When used as distillation aids, the liquid A ROCLOR compounds can be reused several times and either discarded or distilled to restore their original refined state.
Used as stable solvents for reactions conducted in an inert liquid phase, the liquid A ROCLOR compounds perform very well. Here again, the liquids can usually be used several times before discarding or re-purifying.
The other chemicals listed are included to offer a wider choice ol boiling points both at normal and at reduced pressures. The table below will help to choose the correct compound for your reaction or distillation situation. Your Monsanto representative will be glad to discuss specific problems and to provide or obtain other data needed.
Ap(Vpraoluiismtstsr) cPlohhosntyaleny*- Bhicsyiycllo- AfiO1C2L42OR AR1O24C8LOR AR1O25C4LOR AR1O26C0LOR
Wfl-20
DKiUndglsUdon 2J9.24*C. 238*!42C. 125-160#C. JJO-375'C. 365*390C. 185*420'C 340-396'C. 31 2 370'C.
Point 2.5-5.5`C. I I'C minus J9C. minus 7'C- 10'C. 31C. minus 25C- minu* JVC.
Y(SisUe5oiity 100'F.) 11.2 34.2 80*91 185*240 1800-2500 (at7:2i*078'F.) 144 55.7 C\i`
Sprsivclitfyie 250V.913S8.6a*tG 250V.91858.6a'tC. 215'3/8205'aCt . 21S.4V425J'aCt . 215.5V3285#aCt . 215.V62205aCt 215.0*0/l45'aCt. 250V.91751*C.
For further information, eontaet -
MONSANTO CHEMICAL COMPANY Organic Chtmicals Division
800 North Twvlftli BouievirJ St. Louis 1, Minouri
Pnnwd in U S.A.
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PHENYLCYCLOHEXANE
(Cj'doliexylbcnicne)
BICYCLOMEXYL (DicyclohexylI
; ! Monsanto
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Phcnylcyclohcxane and bicyclohcxyl are high boiling, col >rless, oily liquids, free from objectionable odor and relatively free from toxicity.
Structurally, phenybydohexanc is composed of one aromatic six membered carbon ring and one aliphatic (hydrogenated) six membered carbon ring.
Bicyclohexyl is composed of two aliphatic six membered carbon rings (both
saturated with hydrogen).
.
Both products are suggested for use as high boiling solvents and compa* tibilixing agents and penetrating agents.
Interesting derivatives can be made from phenylcydohexanc by sulfona' *?* tion, nitration, halogcnation and condensation with reactive chemical agents.
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PMENYLCYCLOHEXANE (Cyclohcxylbenxenc)
Phcnylcydohcxanc is a product of hydrogenation of biphenyl under proper conditions to saturate one of Me benzene rings. Therefore, phenylcyclohexanc possesses the properties of both aromatic and aliphatic nature. It is a high boiling, colorless, oily liquid, free from objectionable odor and relatively free from toxicity. Phenylcyclohexane is of interest as a high boiling solvent and compatibiliting agent and penetrating agent. It possesses good electrical resistance, and interesting derivatives can ly made from it. The physical, electrical and chemical properties of phenyleyclohexane arc described as follows:
PHYSICAL PROPERTIES
Molecular Weight: Appearance: Color: Odor: Specific Gravity(U) Pounds per Gallon (11) " Refractive Index (11) Viscosity (11) Freezing Point (U) Distillation Ranee (11)
bc/( to 95/r Flash Point, open cup (11) Flame Pcint, open cup (11) Vapor Pressure (11) (12)
Temporafure, cC.
20 30 40 50 70 . 100 136.65 163.6 186.25 221.7 240.1
160 25 Colorless Oily Liqi id
Water White Tlcasa.it
0.938 0.002 at 25/15.6:. 7.82 (Av)
1.523 0.002 at 25C. 31.2 Saybolt Seconds at 1005F.
2.5'5.5C.
239 -- 244C. 2I0F. 220F.
Pressure, rnm.Hg.
0.1 0.15 0.30 0.60 2.0 9.0 40.0 100.0 200.0 500.0 760.0.
Electrical Properties -- Typical Values (II)
Dielectric Constant at 25C. -- 60 cycles to100 lee Dielectric Constant at 100C.--60 cycles to100 kc Power Factor at 100C. -- 60 cycles Volume Resistivity at 1005C., 500 volts DC
-- 2.54 -- 2.45 -- 0.22Sc -- 50,000 x 3 0"ch/n-cm.
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COMPATIBILITY OP PHENYLCYCLOHEXANS (I I)
lohexane is not soluble in water, but is miscible at 25C. with many solvents and < are typical:
Solvent
Acetone Bcntent Carbon Tetrachloride Castor Oil Dichloromethane Ethyl Acetate Ethyl Alcohol
. '
Glycerine Hexane Mineral Oil Stoddard Solvent TiicMorobeniene
Xylene
Solubility
Miscible Miscible Miscible Miscible Miscible Miscible 44 ml. of phcnylcyclo* hexane will dissolve in 100 ml. of alcohol at
25C. Immiscible
Miscible Miscible Miscible Miscible Miscible
SOLUBILITY OF SOME ORGANIC COMPOUNDS IN PHENYLCYCLOHEXANE AT JS^C. (Il|
Solulo
Biphenyl DDT Naphthalene
Paraffin Wax Stearic Acid Pcntachlorophenol Santowax 0 Santowax M Santowax P Santowax R
`
`
Grams/100 Gms. Phenyl*
cyclohexane
55 55 33 18 13
4.7 69 14
3.4 3,3
CHEMICAL PROPERTIES
p Cycloherylbunrano Sulfonic Acid
.
P tcnylcydohexanc can be readily sulfonatcd with 100% H,SO, (9). The barium, sodium, potassium, lead
aed nickel salts of the sulfonic acid have been prepared (6).
H,SO, C,,H,,--------------- > C,H,,.C.H,SO,H + H,0
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Nitro Cycfohorylbeniene
#
A mixture of or;ho and para nitrocydohcxylbcnztnc can.bc prepared by nitration with HNOj and acetic acid
(7), UNO, and acetic anhydride (10), and fuming UNO, and H,SCh (6). The para isomer predominates. The corresponding amines can be readily obtained by reduction of the nitro compounds.
HNO,
C,,H,------------- > C8H,,.CtH4NO, + H*0
HSO
(m.p,: Ortho, 45C; Para, 57C,)
(b.p. Ortho, 1130; Para, 142&C.) at 0.5 mm.
p*Cycfohorylacetophnone The ketone derivative is obtained by condensing acetyl chloride (7) (8) or acetic anhydride (4) with phenyl* cyclohexane in the pre* nee of aluminum chloride.
AIC1 C,,H,6 4- CHjCOCl .------------- > aH,,.CEH4COCH,
(m.p. 68'9C.)
'
CMoromethyl Cyclohexylhfcniene
The chloromethyl derivative of phcnylcyclohexanc has been made by reaction with paraformaldehyde, zinc chlo ride and ltd (l) (2) (3).
C,,H,
HCI --------------------------> C,.Hll.CcH<CH:Cl paraformaldehyde
ZnCI
p*Cyclohexylbenzone Sutfonyl Chloride With chlorosulfonic acid, phcnylcyclohexanc forms paracyclohcxylbcnzene sulfonyl chloride in yields of 85r (5).
HSOjCl C,,H,,, ------------------- > C.H,,.CH,S0,C1
(m.p. 160C.)
p-Bromocyclohexylbenzene Jn an excess of phcnylcyclohexanc with an iodine catalyst bromination proceeds to the p-bromo derivative (l) (13). The bromide forms the Grignard reagent.
C,,H,
Br. ------- > CflHn.Cr.H<Br [, (m.p. 60.4C.)
(b.p. 153C.) at 10 mm.
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BIBLIOGRAPHY
(1) Bodroux and Thomassin, Bull. Soc. Chim, 6, 1411'16 (1939); C.A. 3_3, 9314 (1939). (2) Braun, Irmish, NelJes, Ber. 66, 1471 (1933); C.A. 28, 139 (1934). (3) Cludsvick, Monsanto Chemical Co., Anniston, Ala., Unpublished Report.
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B1CYCL0MEXYL (Dicyclohcxyl)
Bicyclohexyl is a product of the hydrogenation of biphenyl under proper conditions to saturate both aromatic rings. The material is a colorless oil possessing a pleasant odor. It is relatively non-toxic to higher animals.
U. S. Patent 2,448,093 L. D. Gittings) includes dicyclohcxyl as an ingredient in penetrating oil. Militaty Specifications MIL-F-7197 lists dicyclohexyl as a rubber swelling reference fluid (1).
Molecular Weight Apperance Color Odor Specific Gravity (2) Pounds per Gallon (2) Refractive Index (1) (2)
Viscosity (2)
Freezing Point (2)
Distillation Range (2) 5% to 95%
Flash Point, open cup (1)
#
Flame Point, open cup (2)
Aniline Point, C. (2) <3)
Vapor Pressure (2) (5)
Tmpp/afure, C.
20 JO 40 50 70 . 100 1J4.J5 1(51.2 184.45 220.15 238.5
PHYSICAL PROPERTIES
166.30 Clear, mobile liquid
Water white Pleasant
0.883 0.002 at 25/15.6C. 7.37 (Average)
1.4800 ri: 0.002 at 20C. 34.2 Saybolt Seconds at lOO^F
3.07 Ccntistfikcs at 100F. 1.23 Cen istokes at 210F.
-1'3C. ` 238-242C.
215F. 220F. 4S.2C'C.
Pressure, mm Hg.
' 0.1 0.2 0.4 0.8 2.5 10.5
40 100 200 500 760
BIBLIOGRAPHY
(1) Military Specification MIL-F-7197 (May 15, 1951) --Air Development Force, Wright-Pattcrson Air Force Base, Ohio.
(2) Monsanto Specification and Unpublished Data.
(3) Jo, Wood and Gamer, J. Inst. Petroleum 2SL 159-71 (1942); C.A. 37, 4886
(1943).
""
(4) Goodman and Wise, National Advisory Committee for Aeronautics, Technical
Note 2419, January 25, 1951; 2-Alkvlbiphenyl and the two isomeric 2-alkyIbicyclohexyl scries.
(5) Fenskc, Myers and Quiggle, Ind. Eng. Chem. 42, 649-53 (1950).
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