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Catalyst and preparation method thereof, catalyst composition and method for preparing straight-chain alcohol from epoxy compound

A technology for epoxy compounds and catalysts, which can be applied in chemical instruments and methods, catalysts for physical/chemical processes, compounds of Group 5/15 elements of the periodic table, etc., and can solve the problems of low linear yield and difficult industrial production.

Active Publication Date: 2021-09-17
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Patent CN110922478A uses KOH as a catalyst to obtain linear alcohol by microwave heating, but the linear yield obtained by this method is not high, and it is difficult to industrialize production. Therefore, there is an urgent need for a large-scale production and high linear selectivity. catalyst

Method used

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  • Catalyst and preparation method thereof, catalyst composition and method for preparing straight-chain alcohol from epoxy compound
  • Catalyst and preparation method thereof, catalyst composition and method for preparing straight-chain alcohol from epoxy compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] (1) Preparation of catalyst

[0040] Mix divinylsilane (841.9g, 10mol), dimethylphosphine (1551.25g, 25mol), and azobisisobutyronitrile (164.21g, 1mol) into a reaction kettle, heat to 90°C, and react for 1h; then Cool to room temperature, add 5L tetrahydrofuran, ZnCl 2 (1635.6g, 12mol) stirred 1.5h, obtained target catalyst, structural formula is as follows:

[0041]

[0042] Elemental analysis: C: 27.82; H: 6.72; P: 17.96; Si: 8.16. 1H NMR (500MHz, Chloroform-d): δ7.24 (m, 1H), 4.46 (dh, 2H), 2.14 (dddd, 4H) , 1.81(s,12H), 1.21(dddd,4H).

[0043] (2) Propylene oxide prepares propanol

[0044] Propylene oxide (580.8g, 10mol), catalyst (3.456g, 0.01mol), NaBH 4 (75.66g2mol) and sodium trifluoroacetate (68g, 0.5mol) were dissolved in dichloromethane, heated to 60°C, and reacted for 1.5h to obtain the product. The selectivity of propanol was 98.97% according to gas phase analysis data.

Embodiment 2

[0046] (1) Preparation of catalyst

[0047] The preparation steps are the same as in Example 1, except that the dimethylphosphine (620.5g, 10mol) in Example 1 is changed into diphenylphosphine (6516.65g, 35mol) to obtain the target catalyst, and the structural formula is as follows:

[0048] Elemental analysis: C: 56.65; H: 5.26; P: 10.46; Si: 4.75.

[0049] 1H NMR (500MHz, Chloroform-d): δ7.63(ddt,8H),7.38(tt,4H),7.26–7.18(m,4H),6.92–6.76(m,3H),3.10(dq,4H) ,1.44(dddd,4H).

[0050] (2) Preparation of ethylene glycol from 2-hydroxypropylene oxide

[0051]2-Hydroxypropylene oxide (600.5g, 10mol), catalyst (29.69g, 0.05mol), NaBH 4 (283.73g, 7.5mol), magnesium trifluoroacetate (686.6g, 5mol) were dissolved in dichloromethane, heated to 80°C, and reacted for 1.0h to obtain the product. The yield of ethylene glycol was 99.12 %.

Embodiment 3

[0053] (1) Preparation of catalyst

[0054] The preparation steps are the same as in Example 1, except that the dimethylphosphine (620.5g, 10mol) in Example 1 is changed into diisopropylphosphine (4386.3g, 30mol) to obtain the target catalyst, and the structural formula is as follows:

[0055] Elemental analysis: C: 42.03; H: 8.63; P: 13.50; Si: 6.11.

[0056] 1H NMR (500MHz, Chloroform-d) δ3.41(m,2H),2.82(m,1H),2.72(dp,4H),2.40(td,2H),2.31(td,2H),1.29(d, 24H), 1.26–1.12(m, 4H).

[0057] (2) 2-phenyl propylene oxide prepares phenethyl alcohol

[0058] With 2-phenyl propylene oxide (1201.5g, 10mol), catalyst (11.74g, 0.025mol), NaBH 4 (118.03g, 3.12mol) and magnesium trifluoroacetate (256.8g, 1.87mol) were dissolved in toluene, heated to 85°C, and reacted for 2.0h to obtain the product. The yield of phenylethyl alcohol was 98.86% according to gas phase analysis data.

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Abstract

The invention provides a catalyst and a preparation method thereof, a catalyst composition and a method for preparing straight-chain alcohol from an epoxy compound. The structural formula of the catalyst is shown in the specification, wherein R1 and R2 are H, aryl or C1-C8 alkyl; R2 and R1 are the same or different, preferably C1-C4 alkyl and phenyl. When the catalyst, trifluoroacetate and NaBH4 are used for preparing straight-chain alcohol from an epoxy compound, the catalyst has high reaction activity and straight-chain selectivity; the method has the advantages of simple and convenient process, low cost and energy consumption, good production safety, high product quality and the like, and is particularly suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the field of catalysts and organic synthesis, in particular to a catalyst for preparing straight-chain alcohols by catalyzing epoxy compounds and a method for preparing straight-chain alcohols. Background technique [0002] The most important application of epoxy compounds is the preparation of alcohols through ring-opening reactions. These alcohols are usually used in polyurethanes and various perfume esters. In some polyester applications, because the product needs to have high-strength properties, the polymer needs to have a lower degree of branching to enhance crystallization performance; thus, alcohols with high linearity are required to act as monomers, for asymmetric epoxy compounds It is usually difficult to control the ring-opening direction of the ring-opening of , and obtain highly selective straight-linked alcohols. [0003] Patent CN110922478A uses KOH as a catalyst to obtain linear alcohol by microwave heating, b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/24C07F9/50C07C31/10C07C31/20C07C33/22C07C29/132
CPCB01J31/24B01J31/2409C07F9/5045C07F9/505C07F9/5059C07C29/132B01J2531/26B01J2231/641C07C31/10C07C31/202C07C33/22Y02P20/584
Inventor 许振成刘超黄少峰任亚鹏
Owner WANHUA CHEM GRP CO LTD