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Process for purification of chlorinated alkenes

A technology for chlorinating olefins and butadienes, which can be used in chemical instruments and methods, organic chemistry, halogenated hydrocarbon preparation, etc., and can solve problems such as excessive loss of isomers

Active Publication Date: 2010-12-01
DENKA PERFORMANCE ELASTOMER LLC (N D GES DES STAATES DELAWARE)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Excessive loss of the desired isomer during recovery operations when the undesired isomer is separated from the recovered reactant stream by general distillation techniques

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Chlorine gas at a molar ratio of 0.150 was passed into a batch chlorination reactor containing a mixture of α-chloroprene and β-chloroprene. N-methylpyrrolidone was added at a level of 1% by weight relative to the weight of the organic reactants for ionic chlorination. A free radical inhibitor containing 200 molar ppm oxygen was then added. The reactor temperature was limited to below 50°C by cooling. After the reaction was depleted of chlorine, calculations showed that the ratio of the alpha to beta isomer in the product decreased by 42% to 0.01033, at which point 14% of the beta-chloroprene isomer feed was chlorinated.

Embodiment 2

[0040] The reactant streams described in Example 1 were fed continuously at the same component ratios into a stirred tank reactor of sufficient size to allow substantially complete conversion of the fed chlorine. The reactor temperature was limited to below 50°C by cooling. Chlorine vapor was fed into the organic feed stream at a molar ratio of 0.183. Under these conditions, the ratio of α-chlorinated isomer to β-chlorinated isomer in the product stream was reduced by about 39%.

Embodiment 3

[0042]Chlorine vapor at a molar ratio of 0.150 was passed into a batch chlorination reactor containing alpha-chloroprene and beta-chloroprene in a ratio of 0.00301. N-methylpyrrolidone was then added at a level of 1% by weight relative to the weight of the organic reactants for ionic chlorination. A free radical inhibitor containing 200 molar ppm oxygen was then added. The reactor temperature was limited to below 50°C by cooling. After the chlorine in the reaction is depleted, calculations show that the ratio of the α-chlorinated isomer to β-chlorinated isomer in the product stream decreases by 42% to 0.001748, at which point 14% of the β-chlorinated isomer enters material is chlorinated.

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Abstract

Purified chlorinated alkenes are produced by a process in which a mixture of i) a first chlorinated alkene that has at least one beta-chlorine substituent and no alpha-chlorine substituents and ii) a second chlorinated alkene that has at least one alpha-chlorine substituent is contacted with chlorine in an amount sufficient to further chlorinate the second chlorinated alkene, but which is insufficient to cause conversion of more than 20% of the first chlorinated alkene. The resultant reaction product may be easily enriched to provide a chlorinated alkene product wherein a) the weight percentage of chlorinated alkenes having at least one beta-chlorine substituent and no alpha-chlorine substituents, based on the total weight of the chlorinated alkenes present in the enriched chlorinated alkene product compared to b) the weight percentage of chlorinated alkenes having at least one beta-chlorine substituent and no alpha-chlorine substituents, based on the total weight of the chlorinated alkenes present in the mixture prior to chlorination is increased by at least 0.25 wt.%.

Description

field of invention [0001] The present invention relates to an improved process for producing chlorinated olefin compositions comprising chlorinated olefins having chlorine substituents at the beta carbon atoms. Background of the invention [0002] Chlorinated olefins are important industrial chemicals that are used in the manufacture of a variety of chlorinated polymers and organic chemicals. For example, chlorinated olefins can be used as monomers in polymerization reactions to produce thermoplastic and elastomeric compositions. These materials are used to make adhesives and molded and extruded products such as gaskets, hoses and thermoplastic profiles. [0003] In many cases, the production of chlorinated olefins, including chlorinated olefin monomers, involves the dehydrochlorination of chlorinated alkanes or other chlorinated alkenes as a step in a reaction sequence. A typical dehydrohalogenation process in the presence of a phase transfer catalyst is described in U.S....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/358C07C21/20C07C17/395
CPCC07C17/25C07C17/395C07C17/10C07C17/23C07C21/20C07C21/21
Inventor T·W·雷德温
Owner DENKA PERFORMANCE ELASTOMER LLC (N D GES DES STAATES DELAWARE)
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