Process for production of ethers

A manufacturing method and composition technology, which are applied in the field of compositions with catalytic functions, can solve the problems of poor thermal stability of palladium complexes, inability to increase the conversion rate of butadiene, and inability to reduce the amount of butadiene catalyst, and achieve low Cost, effect of high catalytic activity

Inactive Publication Date: 2006-03-01
KURARAY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of phosphine-coordinated palladium complexes as catalysts for industrial telomerization has the following problems: (1) the phosphine-coordinated palladium complex has poor thermal stability, and when the telomerization product and the catalyst group are separated by evaporation Time-sharing, the complex decomposes in this step, and metallic palladium is precipitated
The present inventors also found that there is a problem that the amount of catalyst used per equivalent of butadiene cannot be reduced, or the conversion rate of butadiene cannot be increased, because the coordination of phosphorus prevents a sufficient increase in charge density on palladium.

Method used

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  • Process for production of ethers
  • Process for production of ethers
  • Process for production of ethers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Under argon atmosphere and room temperature, bis(dibenzylideneacetone)palladium (2.0 mg, 3.5 micromol), methanol (30 mL, 0.74 mol), (1.2 mg, 14 micromole), potassium methoxide (24.5 mg, 0.35 mmol), and 1,2,4-trimethylbenzene (1.0 g, internal standard). After feeding 1,3-butadiene (30 mL, 0.35 mol), the mixture was heated to 8OC. After 2 hours and 3 hours, the obtained reaction mixture was analyzed by gas chromatography (Shimadzu Corporation, GC-14B). The results are shown in Table 1.

Embodiment 2

[0084] The same reaction and operation as in Example 1 were carried out, except that 1,1-dimethylpropylisocyanate (1.4 mg, 14 micromole) was used instead of tert-butylisocyanate. The reaction mixture obtained was analyzed by gas chromatography (as described above). The results are shown in Table 1.

Embodiment 3

[0086] The same reaction and operation as in Example 1 were carried out, except that 1,1,3,3-tetramethylbutylisocyanate (1.9 mg, 14 micromole) was used instead of tert-butylisocyanate. The reaction mixture obtained was analyzed by gas chromatography (as described above). The results are shown in Table 1.

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Abstract

A process for the production of ethers, characterized by reacting a conjugated diene with an alcohol via telomerization in the presence of a catalyst composition comprising a palladium compound, an isocyanide represented by the general (I): R<1>R<2>R<3>CNC (I) and a base represented by the general formula (II): M(OR<4>)n (II) [in the formulae, each symbol is as defined in the description]. According to the process, ethers can be industrially advantageously produced by telomerization of a conjugated diene with an alcohol.

Description

technical field [0001] The present invention relates to a method for producing ethers comprising telomerization of conjugated diene compounds and alcohols, and to a catalytically functional composition used in the method. [0002] The ethers produced by the method of the present invention can be used as raw materials of various polymers, and can be used as intermediates of perfumes and the like. Background technique [0003] The telomerization reaction of the conjugated diene compound refers to the oligomerization reaction of the conjugated diene compound by introducing a nucleophilic reactant. For example, there can be mentioned a reaction in which 2 molecules of butadiene react with 1 molecule of an active hydrogen-containing compound such as acetic acid or the like to give a product such as 1-acetoxy-2,7-octadiene or the like. [0004] Palladium complexes, especially phosphine-coordinated palladium complexes, are known to exhibit high catalyst activity for the telomeriza...

Claims

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Application Information

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Patent Type & AuthorityApplications(China)
IPC IPC(8): B01J31/22C07C41/06C07C43/15C07B61/00
Inventor石野博重岩崎秀治
OwnerKURARAY CO LTD