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0 M , THE MERCK INDEX AN ENCYCLOPEDIA OF CHEMICALS. DRUGS. AND BIOLOGICALS TENTH EDITION Martha Windholz. Editor Susan Budavari, Co-Editor Rosemary F. Blumetti. Associate Editor Elizabeth S. Otterbein, Assistant Editor ,F48.;2. Published by MERCK & CO., INC. RAHWAY. N.J.. U.S.A. 1983

n-Propylbenzene 15.35%a N 23.70%. aldehyde + ammo- n. Schwoegler, U.S. w pressure catalytic nd, Cassis, J. Am. ic hydrogenation of :)at. 3,117,162 (1964 ria odor. dfl 0.719; it. closed cup: 10'F =ther. Keep tightly H. F. Smyth et aL. c crystals, mp 157- ts chloroform. Keep i sensitizer. opane. C~Ht=; mol _H=CH=CHs. Prepd zylmagnesium chlo- ;yn. coll. vol. I, 471 , 159.2'; bp,, 135.7'; ~6.8'; bpa 43.4'; bp ly sol in water (0.0~ : t rats: 6040 mg/kg, ' «coL 2, 327 (1964). solvent for cellulose ; •pane. C3H7Br; mol %. CH3CH CH3Br. : bp 71'; n? 1.4341. :ohol, etc. id pn tster. C7- 10.84:.. 1 24.58%. bp 143'; no 1.4005. . ether. LD, orally ^t al, Food Cosmet. pana C3HTCI; mol o. CH3CH=CH,CI. presence of ZnC12. " to -123'; bp 46- water; miscible with rbonochloridic acid C4H7 00 ; mol wt 0 26.1R. C3H70- 16'. Gradually dec chloroform, ether. o eyes and mucous irylamino)-2,4,6- tri- diacetylamino)-2,4,- Pulmidol. Ct,Hti- '_.20%, 1 59.40%a N ,ropyl 3-acetamido- Brit. pat. 898,780 ue me -1). hylenL. .aethyleth- 4.37 0. H=C=CH- ie refining of gaso- line. Catalytic or thermal cracking of hydrocarbons always yields propylene. If necessary, it can be obtained by catalyt- ic dehydrogenation of propane. Reviewa.• R. F. Goldstein. The Petroleum Chemicals Industry (New York-London. 1949) p 114 sqq.; Sherwood. Ind. Chemist 1960, 542-546; Chim. et Ind 1961, 576-587; Haney, "Ethylene, Propylene and I-Butene" in Vinyl and Diene Monomers, E. C. Leonard, Ed. (Interscience, New York, 1971) pp 577-689; M. R. Schoenberg et aL. in Kirk-Othmer Encyclopedia of Chemical Technology vol. 19 (Wiley-Interscience, New York, 3rd ed., 1982) pp 228-246. Flammable gas. Burns wjth yellow sooty flame. d 1.49 (air = 1.0). mp (triple pt) -185'. bpr,0 -48'. Critical temp 91.8'. Critical pressure 45.6 atm. Heat of fusion 717.6 cal/mol. Liquefies at 7-8 atm. d240 (liq) 0.5139. Flammable limits in air: 2.4-10.3% (by volume). Latent heat of vapor- ization at bp: 104.62 cal/g. Dipole moment 0.35. np40 1.3567. Surface tension at 90': 16.70 dynes/cm. Shipped as a liquefied gas in low pressure steel cylinders under its own vapor pressure of about 136 pounds per square inch. Con- taminants are propane. ethane, carbon dioxide. USE: In polymerized form as polypropylene plastic. Raw material in the manuf of acetone, isopropylbenzene, isoprop- anol, isopropyl halides, propylene oxide. Caution: Simple asphyxiant. High concns cause unconsciousness. 7751. Propylene Chlorohydrin. 2-Chloro-I-propanol; 2chloropropyl alcohol. CsHrC1O; mol wt 94.54. C 38.11% H 7.46%, CI 37.50%a, 0 16.92%. CH CHCICH=OH. Colorless liquid; pleasant odor. d~ 1.103; bp 133-134'; no 1.4362. Sol in water, alcohol, etc. LDs. orally in rats: 0.22 ml/kg; by skin penetration in rabbits: 0.48 ml/kg, Smyth et aL. Am. Ind Hyg. Assoc. J. 30, 470 (1969). USE: In prepn of propylene oxide (q.v.). 7752. sec-Propylene Chlorohydrin. t-Chloro-l-propan- ol; 1-chloroisopropyl alcohol. C3H,CIO; mol wt 94.54. C 38.11%, H 7.46%, Cl 37.50% 0 16.92%. GCH=CH(OH)- CHj. Colorless liquid. dls 1.115; bp 126-127'; np 1.4392. Sol in water, alcohol, etc. 7753. Propylenediamine. 1,2-Propanediamine. C3HtsNr mol wt 74.13. C 48.61%, H 13.60%, N 37.80%. CH3CH- (NH=)CH=NH=. Prepd from propylene dibromide and alco- holic ammonia at 10(`. Extremely hygroscopic, strongly alkaline liq. Rapidly ab- sorbs moisture to form a hemihydrate. dts 0.878 in anhydr form. bp 119-120'. Very sot in water. Keep tightly closed. USE: In conjunction with cupric sulfate it is a very sensi- tive reagent for mercury. 7754. Propylene Dibromide. !,2-Dibromopropana C3- H,Br=; mol wt 201.91. C 17.84%, H 3.00'°Jo, Br 79.16%. CH3CHBrCH2Br. Prepd from propyl bromide and Br in the I presence of AICIs or AIBrs. Colorless liquid. mp -55'; bp 140-142'; no 1.5203; d" 1.933. Slightly sol in water; miscible with organic solvents. 7755. Propylene Dichloride. 1,2-Dichloropropane. Cs- H,Clr; mol wt 112.99. C 31.89%, H 5.35% Cl 62.76%. CH3CHCICH=CI. Prepd from propyl chloride and Sb=Cls. Flammable, mobile liq. Odor of chloroform. dfl 1.159; bp 95-96'. Sies below -70'. np 1.4388. Flash point (ASTM open cup) 21' (70'F). Despite the low flash pt it does not catch fire readily in industrial applications. Fire pt 38'. Slightly sol in water; miscible with organic solvents. LD, orally in rats: 1.19 ml /kg, H. F. Smyth et aL, Am. Ind Hyg. Assoc. l. 30, 470 (1969). USE: Oil and fat solvent: in dry cleaning fluids; in degreas- ing. In insecticidal fumigant mixtures. Caution: May be ir- ritating to eyes, mucous membranes, and in high concns, narcotic. Has caused liver, kidney necrosis in exptl animals. ~ 7756. Propylene Glycol. !,2-Propanediol: methyl glycol; 1.2-dihydroxypropane. C3HtOt; mol wt 76.09. C 47.35%. H 10.60%, 0 42.05%. CHsCHOHCH=OH. Prepn from glycerol: Raschig, Prahl. Ber. 61, 185 (1928). Prepn of le- vorotatory propylene glycol from hydroxyacelone by yeast reduction: Levene, Walti, Org. Syn. coil. vol. 11, 545 (1943). Synthesis of S-(+)-form: C. Melchiorre, Chem. Ind. (L.on- don) 1976, 218. Manuf from propylene oxide by hydration: Faith, Keyes & Clark's Industrial Chemicals. F. A. Lowen- heim, M. K. Moran, Eds. (Wiley-Interscience, New York, 4th ed., 1975) pp 688-691. Taken internally, propylene gly- col is harmless, probably because its oxidation yields pyruvic and acetic acids, cf. Whitmore, Organic Chemistry (New York, 1951). Review on toxicity, metabolism and biochem- istry: Ruddick. ToxicoL AppL PharmaooL 21, 102 (1972). dl-Form, hygroseopie, viscous liquid. Slightly acrid taste. df 1.036; freezes at -59; bp7, 188.2'; bpn 168.1'; bpm 149.7'; bpt,, 132.0'; bpW 119.9^, bpp 111.2'; bpm 96.4'; bpts 83.2'; bps 70.8'; bpt4 45.5'. Flash pt, open cup: 2i0'F (99°C). Miscible with water, acetone, chloroform. Sol in ether. Will dissolve many essential oils, but is immiscible with fixed oils. It is a good solvent for rosin. Under ordi- nary conditions propylene glycol is stable, but at high temps it tends to oxidize giving rise to products such as propional- dehyde, lactic acid, pyruvic acid and acetic acid. LD,, orally in rats: 25 ml/kg, W. Bartsch et aL, Arrneimittel-Forsch. 26, 1581 (1976). /-Form, bpu 88-90', bp~ 187-189'. [a]~° -15.0'. d-Form, bp 94-%'. [a] + 15.84% (neat). d2s 1.04. USE: As nontoxic antifreeze in breweries and dairy estab- lishments. Solvent for pharmaceuticals. Substitute for eth- ylene glycol and glycerol. In the manuf of synthetic resins. As inhibitor of fermentation and mold growth. As mist to disinfect air. As emulsifier in foods. TttERM CAT: Pharmaeeutic aid (humectant; solvent). THERAP CAT (vET): Glucogenic (orally) in ruminants. As a solvent for drugs. 7757. Propylene Oxide. Methylorimne; propene oxide. CsHiO; mol wt 58.08. C 62.04%, H I0.41%a 0 27.55%. Re- sults from the action of KOH (aq) on propylene chlorohy- drin. Revieax Holden in Glycols, G. O. Cutme, F. John- ston, Eds., A.C.S. Monograph Series no. 114 (Reinhold, New York, 1952) pp 250-261; Faith, Keyes & Clark's In- dustrial Chemicals~ F. A. Lowenheim, M. K. Moran, Eds. (Wiley-Interscience, New York, 4th ed., 1975) pp 692-697; R. O. Kirk, T. J. Dempsey in Kirk-Othmer Encyclopedia of Chemical Technology vol. 19 (Wiley-Interscience, New York, 3rd ed., 1982) pp 246-274. / 0\ v -CH3 Colorless ethereal liquid. Extremely flammablee dO4 0.859; fp -112.13'; bp 34.23'. Flash pt, closed cup: -31'F (-35'C). Soly in water (20'): 40.5% by wt; soly of water in propylene oxide: 12.8% by wt; miscible with alcohol, ether. LD,* orally in rats: 1.14 g/kg, H. F. Smyth et aL. J. Ind. Hyg. Toxicot. 23, 259 (1941). USE: Chemical intermediate in prepn of polyethers to form polyurethanes; in prepn of propylene and dipropylene gly- cols; in prepn of lubricants, surfactants, oil demulsifiers. Also as solvent; fumigant; soil sterilant. 7758. Propyl Ether. l,l '-Orybispropanr dipropyl ether. C6H,O; mol wt 102.17. C 70.53%, H 13.81%, 0 15.66%. C3H7OC3H.t. Obtained by heating propyl alcohol with benz- enesulfonic acid. Mobile liquid. Extremely flammable. dm 0.7360; mp -122'; bp 89-91'; no 1.3807. Flash pt, open cup: -5'F (-20'C). Slightly sol in water; sol in alcohol, ether. Highly volatile. Tends to form explosive peroxides. esp when an- hydr. Do not allow to evaporate to near dryness. 7759. Propyl Formate. Formic acid prnpyt ester. C4- HtO=: mol wt 88.10. C 54.53%, H 9.15%. 0 36.32%. HCOOCtH7. Colorless liquid; pleasant odor. da' 0.901: mp -93'; bp 81-82'. Flash pt, closed cup: 27'F (-3'C). np 1.3771. Sol in 45 parts water; misc with alcohol, ether. LD„ orally in rats: 3980 mg/kg, P. M. Jenner et at.. Food Cosmet. ToxicoL 2, 327 (1964). 7760. Propyl Gallate. .1.4,5-Trihyd%ryben:oic acid pro- pyl ester: n-propyl gallate: gallic acid propyl ester; PG; Pro- gallin P: Tenox PG. C10Ht=Os; mol wt 212.20. C 56.60%, H 5.70%, 0 37.70%. Spectrophotometric determn: C. S. Sas- try et al., Talanta 29, 917 (1982). Effects on survival of Sacrharomyct Food Prot. 46. Augustin, S. I Crystals, ml in alcohol = cottonseed oil g/100 g. Da Synergic with g/kg, Patty's D. Clayton. I York, 3rd ed., USE: Antio: waxes, transfo 7761. Prop atnine; 1-cych oxyephedrine; 155.28. C 77. hydrogenation catalyst and g J. Am. Ckem. 746 (1948 to : d/-Form, oit 92-93'; volatil: slightly sol in its aq solns a, chloroform. et dl-Form h. 128'. Sol in N d-Fotm, oil d-Form hy. + 14.73'. Sol /-Form, oily l-Fotm ethy yl-1-(metdyta: barbital coml: Maliasin. l-Form hyd -14.74'. So1 iHERAP CAT: 7762. Prop. H" CI ; mol w CHr~H=CHCI aldehyde. Liquid. dt* many organic + et aL. Arch. b, 7763. Prop 170.01. C 21 Prepd by heat, phorus. Colorless or -98'; bp 102- cible with alco 7764. Prop acetic acid pru propyl ester; t piodone; Dion, H 2.48%, 1 51 combe, Brit. Tomich et a/., insult the cross index before using this section. Con.vult the cross index be ore using this 8869813