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Method for preparing adipic acid and 2, 5-dihydroxy adipic acid from hexaldehyde saccharic acid

A technology of aldoglucaric acid and hydroxyadipic acid, which is applied in the preparation of carboxylate, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of environmental pollution, high cost, and non-green production process, and achieve Environmental friendliness and the effect of reducing production costs

Active Publication Date: 2020-06-05
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there are two patents on the preparation of adipic acid or its derivatives from hexararic acid, the first of which (CN102869642A) reports the conversion of glucaric acid into adipic acid, but in this process, corrosive Stronger glacial acetic acid is used as a solvent, and hydrohalic acid is used as a catalyst, which is highly corrosive and will inevitably pollute the environment during the production process; the second (CN105899484A) reports that galactaric acid is converted into adipic acid, However, expensive methyl rhenium trioxide is used as a catalyst and 3-pentanol is used as a hydrogen source in the process, which requires cumbersome processes such as esterification and hydrolysis. Not only is the cost high, but the production process is not green.

Method used

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  • Method for preparing adipic acid and 2, 5-dihydroxy adipic acid from hexaldehyde saccharic acid

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0036] 1. TiO 2 Preparation of supported Pd catalyst

[0037] With 1%Pd / TiO 2 The preparation of the catalyst is used as an example for non-limiting illustration.

[0038] 560mg of 10wt% Pd(NH 3 ) 4 (NO 3 ) 2 Mix the aqueous solution with 20mL deionized water, add 2g TiO 2 The carrier was stirred at room temperature for 8 hours, the solvent was evaporated to dryness by a rotary evaporator, and then dried in an oven at 120° C. for 10 hours. Calcined in air at 400°C for 3h, then in 20%H 2 +N 2 Reduction at 300℃ for 1h to get 1%Pd / TiO 2 catalyst. The loading amount of Pd is 1% (mass percentage).

[0039] 2. TiO2 2 Loaded MoO 3 Catalyst preparation

[0040] With 15% MoO 3 / TiO 2 The preparation of the catalyst is used as an example for non-limiting illustration.

[0041] Mix 552mg ammonium heptamolybdate and 20mL deionized water, add 2g TiO 2 The carrier was stirred at room temperature for 8 hours, the solvent was evaporated to dryness by a rotary evaporator, and...

Embodiment 1

[0048] Embodiment 1, prepare 2,5-dihydroxyadipic acid by glucaric acid in aqueous solution

[0049] In a 50mL autoclave, add 0.2g of 1%Pd / TiO 2 Catalyst and 15mL mass percentage content are 2% glucaric acid aqueous solution, after reaction kettle is airtight, be filled with 2MPa hydrogen gas scrubbing three times, in the reaction kettle, be filled with 2MPa hydrogen gas, put reaction kettle on heating furnace and be heated to The reaction temperature was 150° C., and the reaction was stirred for 8 hours at a rotation speed of 600 rpm. After the reaction was completed, the mixture was cooled down to room temperature in an ice-water bath, and filtered under reduced pressure. The filtrate was 2,5-dihydroxyadipic acid with a yield of 93%.

Embodiment 2

[0050] Embodiment 2, prepare 2,5-dihydroxyadipic acid by galactaric acid in aqueous solution

[0051] In a 50mL autoclave, add 0.2g of 1%Pd / TiO 2 Catalyst and 15mL of galactaric acid aqueous solution with a mass percentage of 2%. After the reactor is sealed, fill it with 2MPa hydrogen to scrub three times, then fill the reactor with 2MPa hydrogen, and place the reactor on a heating furnace for heating To the reaction temperature of 150° C., the reaction was stirred at 600 rpm for 8 h. After the reaction was completed, the mixture was cooled down to room temperature in an ice-water bath, and filtered under reduced pressure. The filtrate was 2,5-dihydroxyadipic acid with a yield of 91%.

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Abstract

The invention provides a method for preparing 2, 5-dihydroxy adipic acid and adipic acid from hexaldehyde saccharic acid. The method for preparing 2, 5-dihydroxy adipic acid comprises the following step: in the presence of a catalyst A, reacting hexaldehyde saccharic acid with hydrogen in an aqueous solution for 1 hour to obtain 2, 5-dihydroxy adipic acid. The method for preparing adipic acid comprises the following steps: 1) in the presence of a catalyst A, reacting hexanal disaccharic acid with hydrogen in an aqueous solution for 1 hour to obtain 2, 5-dihydroxy adipic acid; and 2) in the presence of a catalyst B, reacting the 2, 5-dihydroxy adipic acid for 2 to obtain adipic acid. Water is used as a reaction solvent, so that the reaction process is green, pollution-free and environment-friendly, and the production cost is reduced.

Description

technical field [0001] The invention belongs to the field of preparation of chemical raw materials, and in particular relates to a method for preparing adipic acid and 2,5-dihydroxyadipic acid from hexararic acid. Background technique [0002] Adipic acid, commonly known as fatty acid, is an important chemical raw material for the production of nylon 66. The current annual output is more than 3 million tons, ranking second among all dicarboxylic acids. The current industrial production method of more than 90% of adipic acid mainly uses cyclohexanol and cyclohexanone (KA oil) as the nitric acid oxidation method of raw materials, the oxidant nitric acid has strong corrosion to the reaction equipment, and produces a large amount of nitrogen in the production Oxygen compounds seriously pollute the environment. Therefore, the development of a green adipic acid production process has very important application value. Glucose is the constituent unit of cellulose, starch, sucrose...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/377C07C55/14C07C51/367C07C59/245
CPCC07C51/367C07C51/377C07C55/14C07C59/245
Inventor 刘海超王丰鑫
Owner PEKING UNIV
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