Glycerin chlorohydrin

Glycerol (or Glycerin) Chlorohydrin and Its Nitrated Derivatives. See under Chioropropanediol and Derivatives in Vol 3, pp C265-L to C267-L. The dinicrate is described in Blatt, OSRD 2014(1944) as Glycerol Monochlorohy-drin Dinitrate or a-Dinitrochlorohydrin... 

Glycidol is obtained by epoxidation of allyl alcohol or by dehydrochlorination of the corresponding chlorohydrin, such as glycerin chlorohydrin (reaction 19.7). 

Although not in the top 50, it is an important monomer for making epoxy adhesives as well as glycerine (HO-CH2-CHOH-CH2-OH). Propylene is first chlorinated free radically at the allyl position at 500°C to give allyl chloride, which undergoes chlorohydrin chemistry as discussed previously to give epichlorohydrin. The student should review the mechanism of allyl free radical substitution from a basic organic chemistry course and also work out the mechanism for this example of a chlorohydrin reaction. 

The raw material from which dinitrochlorohydrin is produced is chlorohydrin, made by treating glycerine with hydrochloric acid at a temperature of 100-120°C under pressure [20]. The substitution product is a mixture of a- and /S-isomers. (The boiling point of a-chlorohydrin is 130°C at 18 mm Hg that of -chlorohydrin is 146°C at 18 mm Hg). 

Chlorohydrin for the manufacture of dinitrochlorohydrin must be as pure as possible and should contain the minimum amount of water, HC1 and polymerization products of glycerine, since ithe presence of these substances favours the formation of an emulsion during nitration and washing. Usually chlorohydrin was made in the explosives factory. After a single distillation the substance was transferred to the nitrating unit generally in admixture with glycerine. 

In practice, usually a mixture of chlorohydrin with 10-20% of glycerine is nitrated, to yield 165-175 parts of chlorohydrin dinitrates with nitroglycerine. 

SYNS a-CHLORHYDRlN CHLORODEOXY-GLYCEROL 1-CHLORO-2.3-DIHYDROXYPROPANE 3-CHLORO-1.2-DIHYDROXYPROPANE a-CHLOROHYDRIN l-CHLOROPROPANE-2,3-DIOL I-CHLORO-23-PROPANEDIOL 3-CHLOROPROPANE-1,2-DIOL 3-CHLORO-1.2-PROPANEDIOL 3-CHLOROPROPYLENE GYLCOL Q P, 3 -DIHYDROXY-ISOPROPYL CHLORIDE 2,3-DIHYDROXYPROPYL CHLORIDE EPIBLOC GLYCERIN-a-MONOCHLOR-HYDRIN GLYCEROL CHLOROHYDRIN GLYCEROL-a-CHLOROHYDRIN GLYCEROL-a-MONOCHLOROHYDRIN (DOT) GLYCERYL-o-CHLOROHYDRIN MONOCHLORHYDRIN MONOCHLOROHYDRIN a-MONOCHLOROHYDRIN D U-5897... 

Glycerol dinitrate ( Dinitroglyccrine") Explosive properties Manufacture of dinilroglyccrine Mixed Glycerine Esters Chlorohydrine nitrates... 

Glycerol (or Glycerin) Dichlorohydrtn and Its Nitrated Derivotives. See under Dichlorohydrin and Derivatives in Vol 5 pp D1211-L to D1212-R and in Blatt, OSRD 2014(1944), as Glycerol Di chlorohydrin Nitrate... 

Chloropropylene glycol 1-Choropropane-2,3-diol p,P -Dihydroxyisopropyl chloride 2,3-Dihydroxypropyl chloride Glycerin-a-monochlorhydrin Glycerol chlorohydrin Glycerol-a-monochlorohydrin 1,2-Propanediol, 3-chloro-Classification Nonaromatic alcohol Empirical C3H7CIO2 Formula CICH2CHOHCH2 Properties Colorless or pale yel. liq. sol. in water, DMSO, 95% ethanol, acetone, ether, polar soivs. immisc. with oils m.w. 110.54 sp.gr. 1.326 (18/15 C) vapor pressure 3.75 mm Hg (25 C) m.p. -40 C b.p. 213 C (dec.) flash pt. 58 C ref. index 1.4809 (20 C)... 

Ethoxylated Alcohols C, C Ethyl Alcohol Ethylbutanol Ethylene Chlorohydrin Ethylene Cyanohydrin Ethylene Glycol 2-Ethyl Hexanol Furfuryl Alcohol Glycerin Hexanol... 

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