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A kind of catalyst for preparing (s)-3-hydroxytetrahydrofuran and its preparation and use method

A technology of hydroxytetrahydrofuran and catalysts, which is applied in organic chemical methods, chemical instruments and methods, physical/chemical process catalysts, etc., and can solve problems such as difficulty in extraction and separation, reduced output, and high water solubility

Active Publication Date: 2021-07-06
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] This route uses ethyl (S)-3-hydroxybutyrate as a raw material, reduces it with tetrahydrofuran-sodium borohydride system, and then removes hydrogen chloride and cyclizes (S)-3-hydroxytetrahydrofuran under acidic conditions. The operation is simple and the route Shorter, but there are also defects: the reduction product contains hydroxyl groups, which is more water-soluble, and it is more difficult to extract and separate, which reduces the yield
This method is suitable for the preparation of racemic 3-hydroxytetrahydrofuran, and it uses a catalyst for dehydration under the condition that the racemic body may occur at 150-200 ° C, but in the process of applying this method to prepare optically pure 3-hydroxytetrahydrofuran restricted in

Method used

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  • A kind of catalyst for preparing (s)-3-hydroxytetrahydrofuran and its preparation and use method
  • A kind of catalyst for preparing (s)-3-hydroxytetrahydrofuran and its preparation and use method
  • A kind of catalyst for preparing (s)-3-hydroxytetrahydrofuran and its preparation and use method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] (1) Preparation of catalyst:

[0038] (1-1) 38m1TiCI 4 Dissolve in 500ml water, add 28% ammonia water dropwise until the pH of the solution is 8.4, wash with deionized water after suction filtration until there is no C1 - exists, the resulting Ti(OH) 4 The filter cake was dried in an oven at 120°C for 24 hours, and then calcined at 500°C for 5 hours to obtain TiO 2 .

[0039] (1-2) Take 4.7922g (0.06mol) TiO 2 Add 6.7mL 1mol / LH 3 PO 4 , immersion and stirring in a water bath at 80°C until evaporated to dryness, then dried at 100°C, then heated to 600°C within 3 hours, and calcined at 600°C for 4 hours to obtain a molar ratio of P / TiO 2 = 1:9 PO 4 3- / TiO 2 catalyst. Lower the temperature and cool down, crush the tablets into pieces and sieve with 30-50 meshes.

[0040] (2) Preparation of (S)-3-hydroxytetrahydrofuran: the above-mentioned 30-50 mesh molar ratio P / TiO 2 = 1:9 PO 4 3- / TiO 2 Catalyst 2.0g is loaded into the batch type fixed-bed reactor, and t...

Embodiment 2

[0042] (1) Preparation of catalyst: get the TiO prepared according to Example 1 (1-1) 2 4.7922g (0.06mol) add 40.0mL1mol / LH 3 PO 4 , heated in a water bath at 80°C, dipped and stirred until evaporated to dryness, then dried at 110°C, then heated to 600°C within 3 hours, and calcined at 600°C for 5 hours to obtain the molar ratio P / TiO 2 = 6:9 PO 4 3- / TiO 2 catalyst. Lower the temperature and cool down, crush the tablets into pieces and sieve with 30-50 meshes.

[0043] (2) Preparation of (S)-3-hydroxytetrahydrofuran: the above-mentioned 30-50 mesh molar ratio P / TiO 2 = 6:9 PO 43- / TiO 2 Catalyst 2.0g is loaded into the batch type fixed-bed reactor, and the rest is filled with quartz sand. After the system checks the seal, when the volumetric space velocity is 8h -1 N 2 The temperature of the catalytic bed was programmed to 150°C under gas flow. Then inject 96% (S)-1,2,4-butanetriol into the system, and the mass space velocity of (S)-1,2,4-butanetriol is 0.9h -1 ,...

Embodiment 3

[0045] (1) Preparation of catalyst: get the TiO prepared according to Example 1 (1-1) 2 4.7922g (0.06mol) add 60.0mL1mol / LH 3 PO 4 , heated in a water bath at 80°C, dipped and stirred until evaporated to dryness, then dried at 120°C, then heated to 650°C within 3 hours, and calcined at 650°C for 4 hours to obtain the molar ratio P / TiO 2 = 9:9 PO 4 3- / TiO 2 catalyst. Lower the temperature and cool down, crush the tablets into pieces and sieve with 30-50 meshes.

[0046] (2) Preparation of (S)-3-hydroxytetrahydrofuran: the above-mentioned 30-50 mesh molar ratio P / TiO 2 = 9:9 PO 4 3- / TiO 2 Catalyst 2.0g is loaded into the batch type fixed-bed reactor, and the rest is filled with quartz sand. After the system checks the seal, when the volumetric space velocity is 6h -1 N 2 The temperature of the catalytic bed was programmed to 100°C under gas flow. Then inject 96% (S)-1,2,4-butanetriol into the system, and the mass space velocity of (S)-1,2,4-butanetriol is 1.3h -1...

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Abstract

The invention discloses a catalyst for preparing (S)-3-hydroxytetrahydrofuran and a preparation and use method thereof. The catalyst is H 3 PO 4 Modified tetravalent metal oxides. The catalyst can catalyze the one-step reaction of (S)-1,2,4-butanetriol to obtain (S)-3-hydroxytetrahydrofuran, the reaction operation is simple, the production cost is low, the environment is friendly, and compared with the conventional preparation method, the catalyst has higher yield and can remain optically pure.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and in particular relates to a method for preparing (S)-3-hydroxytetrahydrofuran. Background technique [0002] (S)-3-Hydroxytetrahydrofuran It is an important intermediate in the synthesis of anti-AIDS drugs Amprenavir and Fosamprenavir, and can also be used in the synthesis of fine organic chemicals. [0003] Regarding the synthesis of (S)-3-hydroxytetrahydrofuran, most of the current chemical synthesis methods use (S)-4-chloro-3-hydroxybutyric acid ethyl ester as raw material, after reduction, dehydrochlorination in acidic conditions The target product is synthesized by cyclosynthesis. Although the synthesis steps of this method are short, the required raw materials are expensive and the cost is high, so it is difficult to realize industrialization. The synthetic route is as follows: [0004] [0005] This route uses ethyl (S)-3-hydroxybutyrate as a raw material, reduces it wi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J27/18C07D307/20
CPCB01J27/1802B01J27/1813C07B2200/07C07D307/20
Inventor 余定华王文娟
Owner NANJING TECH UNIV