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Method for preparing 1, 6-hexanediol by hydrogenating 1, 6-dimethyl adipate

A technology for the preparation of dimethyl adipate and hydrogen, which is applied in chemical instruments and methods, preparation of hydroxyl compounds, and preparation of organic compounds, etc., can solve the problems of complicated preparation process and poor selectivity of noble metal catalysts, and achieve high catalyst activity, The effect of simplification of separation or purification process and mild reaction conditions

Inactive Publication Date: 2012-03-14
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The purpose of the present invention is to provide 1, the method for preparing 1,6-hexanediol by hydrogenation of dimethyl adipate to the deficiencies in the prior art, and it is characterized in that this method has overcome 1,6-adipic acid The preparation process of the composite oxide catalyst used in the hydrogenation of dimethyl ester to alcohol is complicated, the catalytic reaction needs to be carried out under high temperature and high pressure conditions, and the selectivity of the supported noble metal catalyst is poor.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 20 parts of RuCl 3 2H 2 O, 20 parts SnCl 4 , 5 parts CoCl 2 ·6H 2 O and 1000 parts of γ-Al 2 o 3 Mix, add appropriate amount of ethanol to impregnate for 12h, dry in vacuum and calcined to get Ru-Sn-Co / Al 2 o 3 Catalyst precursor. 20 parts of Ru-Sn-Co / Al 2 o 3 Transfer to an autoclave, then add 100 parts of water as a solvent, replace it with high-purity hydrogen for 3 times, fill it with hydrogen at a pressure of 5.0Mpa, and reduce it for 2 hours at a temperature of 180°C. After cooling, add 100 parts of 1,6-adipic acid Dimethyl ester and 200 parts of methanol were replaced by hydrogen 3 times, filled with hydrogen at a pressure of 5.0Mpa, reacted at a temperature of 220°C for 10 hours, cooled to take out the reaction solution, centrifuged, and analyzed by gas chromatography. The results showed that 1,6-hexanedi The conversion rate of dimethyl ester was 99.5%, and the selectivity of 1,6-hexanediol was 99.5%.

Embodiment 2

[0031] 20 parts of RuCl 3 2H 2 O, 20 parts SnCl 2 , 30 parts CoCl 2 ·6H 2 O and 1000 parts of γ-Al 2 o 3 Mix, add appropriate amount of ethanol to impregnate for 12h, dry in vacuum and calcined to get Ru-Sn-Co / Al 2 o 3 Catalyst precursor. 30 parts of Ru-Sn-Co / Al 2 o 3 Transfer to an autoclave, then add 100 parts of water as a solvent, replace it with high-purity hydrogen for 3 times, fill it with hydrogen at a pressure of 5.0Mpa, and reduce it at a temperature of 180°C for 2 hours. After cooling, add 200 parts of 1,6-adipic acid Dimethyl ester and 200 parts of water were replaced by hydrogen 3 times, filled with hydrogen at a pressure of 3.0MPa, reacted at a temperature of 220°C for 12 hours, cooled to take out the reaction solution, centrifuged, and analyzed by gas chromatography. The results showed that 1,6-hexanedi The conversion rate of dimethyl ester was 99.0%, and the selectivity of 1,6-hexanediol was 98.5%.

Embodiment 3

[0033] 10 parts of RuCl 2 (PPh 3 ) 3 , 15 parts SnO, 5 parts CoCl 2 ·6H 2 O and 1000 parts SiO 2 Mix, add an appropriate amount of 1,4-dioxane to impregnate for 12 hours, stir overnight at room temperature, spin dry, vacuum dry, and calcinate to obtain Ru-Sn-Co / SiO 2 Catalyst precursor. 10 parts of Ru-Sn-Co / SiO 2 Transfer to an autoclave, then add 100 parts of water as a solvent, replace it with high-purity hydrogen for 3 times, fill it with hydrogen at a pressure of 5.0Mpa, and reduce it for 5 hours at a temperature of 100°C. After cooling, add 100 parts of 1,6-adipic acid Dimethyl ester and 100 parts to get 1,4-dioxane, replaced hydrogen 3 times, filled with hydrogen pressure 5.0MPa, reacted at a temperature of 150°C for 10h, cooled and took out the reaction solution, analyzed by gas chromatography, the results showed that 1 , the conversion rate of dimethyl 6-adipate was 79%, and the selectivity of 1,6-hexanediol was 34%.

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Abstract

The invention discloses a method for preparing 1, 6-hexanediol by hydrogenating 1, 6-dimethyl adipate, which is characterized by comprising the following steps and metering in parts by weight: 1000 to 10000 parts of oxide is as a carrier, 100 to 200 parts of heavy metal and 40 to 400 parts of co-catalyst metal salt are immersed for 12h at a room temperature to be pumped, filtered, vacuum dried and calcined to obtain a loaded heavy metal catalyst; 1 to 30 parts of the catalyst and 20 to 400 parts of solvent are filled into a reaction kettle, high-pure hydrogen is used for replacing oxygen in the reaction kettle for 3 to 5 times, the catalyst is activated for 2 to 8h under the temperature of 100 to 200 DEG C, pressure of 1.0 to 3.0 MPa and the blending speed of 200 to 1000 rpm, 50 to 200 parts of 1, 6-dimethyl adipate is filled into the reaction kettle after the reaction kettle is opened, the high-pure hydrogen is again used for replacing the oxygen inside the reaction kettle for 3 to 5 times to be reacted for 5 to 12h under the temperature of 150 to 220 DEG C, the pressure of 3.0 to 5.0 MPa and the blending speed of 500 to 1000rpm, and reaction solution is taken out to analyze; and the conversion rate is 60.0 to 99.9 percent, and the selectivity is 70.0 to 99.9 percent.

Description

technical field [0001] The invention relates to a method for preparing 1,6-hexanediol through hydrogenation of 1,6-dimethyl adipate, belonging to the field of organic synthesis and catalytic reaction. Background technique [0002] 1,6-Hexanediol is mainly used in the production of detergents, cosmetics, antifoaming agents, polyurethanes, coatings, polyesters, disperse fuels and plasticizers. It is a newly emerging important fine chemical raw material and is known as organic Synthetic Neolithic. Polyurethane prepared with 1,6-hexanediol, such as anti-yellowing adhesive, has good low temperature performance and low curing temperature, and is especially suitable for bonding dissimilar materials with different expansion coefficients. In the medical field, 1,6-dibromohexane, which is prepared from 1,6-hexanediol, is used to synthesize indole hormone-suppressing drugs with special curative effects on prostatitis. With the improvement of living standards, people's requirements fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C31/20C07C29/149
Inventor 李瑞祥蒋红斌陈华李贤均
Owner SICHUAN UNIV
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