Conversion of a multihydroxylated-aliphatic hydrocarbon or ester thereof to a chlorohydrin

Abstract

The present invention relates to a process for converting a multihydroxylated-aliphatic hydrocarbon or ester thereof to a chlorohydrin, more specially relates to a process for producing a chlorohydrin, an ester of a chlorohydrin, or a mixture thereof, which includes steps of: contacting a multihydroxylated-aliphatic hydrocarbon, an ester of a multihydroxylated-aliphatic hydrocarbon, or a mixture thereof with a source of an atmospheric or subatmospheric partial pressure of hydrogen chloride to produce a chlorohydrin, an ester of a chlorohydrin, or a mixture thereof, in the presence of a catalyst, wherein the catalyst: (i) is a carboxylate derivative having from two to about 20 carbon atoms and containing at least one functional group selected from the group comprising an amine, an alcohol,a halogen, an sulfhydryl, an ether, an ester, or a combination thereof, wherein the functional group is attached no closer to the acid function than the alpha carbon; or a precursor thereto; (ii) is less volatile than the chlorohydrin, ester of a chlorohydrin, or a mixture thereof; and (iii) contains heteroatom substituents.

Description

[0001] This application is a divisional application of a Chinese patent application with the application number 200580022101.8, the application date being July 18, 2005, and the invention title being 'Conversion of polyhydroxylated aliphatic hydrocarbons or their esters to chlorohydrins'. technical field [0002] The present invention relates to a process for the conversion of polyhydroxylated aliphatic hydrocarbons or esters thereof to chlorohydrins. Chlorohydrins can be used to prepare epoxides such as epichlorohydrin. Background technique [0003] Epichlorohydrin is a widely used precursor of epoxy resins. Epichlorohydrin is a monomer commonly used for the alkylation of bisphenol A; the resulting diepoxide, either as a free monomer or as an oligomeric diepoxide, can progress to high molecular weight resins such as Used in electrical laminates, can coatings, automotive topcoats and clear coats. [0004] A known method of making epichlorohydrin involves the hypochlorinati...

AI Technical Summary

Problems solved by technology

Furthermore, these reagents can cause complete chlorination of polyhydroxylated aliphatic hydrocarbons, leading to unwanted RCl by-products, as taught in Viswanathan, et al. Current Science, 1978, 21, 802-803

[0019] In summary, there are at least five major disadvantages for all the above known schemes for the preparation of chlorohydrins from glycerol or any other vicinal-diol, triol or polyhydroxylated aliphatic hydrocarbon: (1) Hydrochlorination of glycerol or any diol The atmospheric pressure process requires a large excess of HCl, usually 7-10 times molar excess

(2) A variant of the above known process is a very slow, batch type reaction which requires 24-48 hours at a temperature in excess of 100°C and no more than 80-90% conversion to the desired chlorohydrins product

(3) Exotic hydrochlorination reagents can drive the reaction by scavenging, but often produce by-products inconsistent with commercial economic production

(5) When the reaction is run at high pressure to control the evaporation of the reactor contents, the low partial pressure of HCl leads to low conversion or hindered reaction rate

All prior art infers that there is an equilibrium limit to this transformation due to the presence of water in the reaction mixture

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