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

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

Active Publication Date: 2022-07-12
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • A kind of catalyst and preparation method thereof, catalyst composition, and method for preparing straight-chain alcohol from epoxy compound
  • A kind of 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] Divinylsilane (841.9g, 10mol), dimethylphosphine (1551.25g, 25mol), and azobisisobutyronitrile (164.21g, 1mol) were mixed into the reaction kettle, heated to 90°C, and reacted for 1h; then Cool to room temperature, add 5L tetrahydrofuran, ZnCl 2 (1635.6g, 12mol) was stirred for 1.5h to obtain the target catalyst, and the structural formula was as follows:

[0041]

[0042] Elemental analysis: C: 27.82; H: 6.72; P: 17.96; Si: 8.16. 1HNMR (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) Preparation of propanol from propylene oxide

[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, the temperature was raised to 60°C, and the reaction was carried out for 1.5h to obtain the product. The selectivity of propanol was 98.97% by gas phase analysis data.

Embodiment 2

[0046] (1) Preparation of catalyst

[0047] The preparation procedure is the same as in Example 1, except that the dimethylphosphine (620.5g, 10mol) in Example 1 is changed to 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, the temperature was raised to 80°C, and the reaction was carried out for 1.0h to obtain the product. The yield of ethylene glycol obtained by gas analysis data was 99.12 %.

Embodiment 3

[0053] (1) Preparation of catalyst

[0054] The preparation procedure is the same as in Example 1, except that the dimethylphosphine (620.5g, 10mol) in Example 1 is changed to 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) Preparation of phenethyl alcohol from 2-phenyl propylene oxide

[0058] Combine 2-phenylene oxide (1201.5g, 10mol), catalyst (11.74g, 0.025mol), NaBH 4 (118.03 g, 3.12 mol) and magnesium trifluoroacetate (256.8 g, 1.87 mol) were dissolved in toluene, heated to 85° C., and reacted for 2.0 h to obtain the product. The yield of phenethyl alcohol was 98.86% by gas 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 wherein R 1 , R 2 is H, aryl or C 1 ‑C 8 Alkyl; R 2 with R 1 same or different, preferably C 1 ‑C 4 of alkyl and phenyl. The catalyst with trifluoroacetate and NaBH 4 It is used for preparing straight-chain alcohols from epoxy compounds, and has high reactivity and straight-chain selectivity; the method has the advantages of simple process, low cost and energy consumption, good production safety, and high quality of the obtained products, and is especially 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 catalyzing epoxy compounds to prepare straight-chain alcohols and a method for preparing straight-chain alcohols. Background technique [0002] The most important application of epoxy compounds is the preparation of alcohols by ring-opening reactions. These alcohols are commonly used in polyurethanes and various fragrance esters. In some polyester applications, due to the need for high strength properties in the product, a polymer with a lower degree of branching is required to enhance crystalline properties; thus a highly linear alcohol is required to act as a monomer. For asymmetric epoxy compounds It is usually difficult to control the ring-opening direction of , resulting in highly selective direct-linked alcohols. [0003] Patent CN110922478A utilizes KOH as a catalyst to obtain linear alcohol by microwave heating, but the linear yield obtained ...

Claims

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Application Information

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Patent Type & Authority Patents(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