Process for the synthesis of 2-chloro-1,3-butadiene and 2,3-dichloro-1,3-butadiene

The use of organic bases to form organic halide salts in the production of halogenated 1,3-butadienes simplifies and optimizes the synthesis process, improving efficiency and safety by reducing equipment needs and freshwater consumption, and enabling recycling of materials.

WO2026037737A9 Publication Date: 2026-04-16ARLANXEO DEUT GMBH
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Patent Information

Application Number
PCT/EP2025/072848
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2025-06-16
Filing Date
2025-08-08
Publication Date
2026-04-16

AI Technical Summary

Technical Problem

Existing processes for producing halogenated 1,3-butadienes from halogenated 1-butenes are complex, energy-intensive, and suffer from low reactivity, formation of difficult-to-separate suspensions, and high operational costs due to the use of phase transfer catalysts and complex equipment.

Method used

A process using organic bases, either non-polymeric or polymeric, to form organic halide salts with eliminated hydrohalogenic acid, allowing for simplified chemistry with reduced equipment and energy costs, and enabling recycling of auxiliary materials and reduced freshwater consumption.

Benefits of technology

The process achieves increased space-time-yield, reduces operational complexity, minimizes waste, and enhances safety by eliminating hazardous materials and manual handling, while optimizing synthesis and reducing freshwater use.

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Abstract

The invention relates to a process for the preparation of a halogenated 1,3-butadiene by dehydrohalogenation of a halogenated 1-butene. Preferably, 2-chloro-1,3-butadiene (CP) is prepared from 3,4-di- chloro-1-butene (3,4-DBN), or 2,3-dichloro-1,3-butadiene (DCB) is prepared from 2,3,4-trichloro-1- butene (TCB). The dehydrohalogenation is performed in the presence of an organic base, preferably selected from (i) non-polymeric organic bases and (ii) polymeric organic bases. Upon dehydrohalogenation of the halogenated 1-butene, the organic base preferably provides an organic halide salt, namely (i) a low melting organic halide salt, which is an ionic liquid; or (ii) a polymeric organic halide salt. Preferably, halogenated 1,3-butadiene is separated from the reaction mixture by in-situ distillation. Organic base is preferably recovered from (i) the low melting organic halide salt by e.g. heating and release of hydrohalogenic acid; or from (ii) the polymeric organic halide salt by e.g. reconversion of polymeric organic halide salt into polymeric organic base and an inorganic halide salt, and size-based separation of the inorganic halide salt, preferably by filtration, more preferably selected from microfiltration, ultrafiltration and nanofiltration, still more preferably by nanofiltration. After purification, recovered organic base is preferably recycled into the process.
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