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Manufacture of adipic acid

A kind of technology of adipic acid and strong acid, which is applied in the preparation of carbon monoxide or formate reaction, the preparation of carboxylic acid by carbon monoxide reaction, organic chemistry, etc. It can solve the problems of lower yield and long reaction residence time, and achieve good treatment performance.

Inactive Publication Date: 2001-09-26
EI DU PONT DE NEMOURS & CO +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is known that valerolactone requires a very long reaction residence time under the reaction conditions of the prior art, so the valerolactone must be reacted in another vessel to reduce the yield, otherwise the reaction is carried out under more severe conditions

Method used

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  • Manufacture of adipic acid

Examples

Experimental program
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Effect test

example 1

[0047] The mechanically stirred autoclave of 100ml zirconium was purged with carbon monoxide, then added 87g containing 40g (273mmoles) 2-methyl glutaric acid (MGA), 0.40g 57% m aqueous solution (1.8mmolesHI), 0.31g (0.89mmoles) Ir(CO) 2 (acac) 0.53g (29mmoles) water, 0.31g (3.2mmoles) phosphoric acid, 40g (40mmoles) γ-valerolactone, 4.2g (42mmoles) t-3-pentenoic acid and 0.1g (1mmole) 4-pentene acid solution. The autoclave was charged to 10 psi with CO and then heated to 180°C. The autoclave pressure was immediately brought up to 400 psi with CO. After allowing the reaction to proceed for as long as 5 hours, let it cool to 50°C, vent and discharge the product. The autoclave was first cleaned with 80ml of 0.1% HI acetic acid solution at 200°C, then with 80ml of acetone at 20°C, and finally with 80ml of acetic acid at 20°C. The first wash was mixed into the reaction product for analysis. The subsequent washing solution is drained.

[0048] Three samples of each feed mixtu...

example 2

[0061] This example illustrates the recovery of crude adipic acid from the process of the invention when the concentration of valerolactone in the reaction mixture was 30% by weight. Hydrocarboxylation was carried out as described in Example 1, except that the concentration of valerolactone in the reaction mixture was 30% by weight. A 500 g sample of the product stream was placed in a 1 liter glass crystallizer equipped with magnetic stirring and a total reflux condenser (20°C).

[0062] The product stream mixture comprises (by weight):

[0063] 30% gamma-valerolactone

[0064] 25% adipic acid

[0065] 32% 2-methylglutaric acid

[0066] 5% citric acid

[0067] 3% valeric acid

[0068] 3% 2-Methylbutanoic acid

[0069] 1% caproic acid

[0070] 1% 3-pentenoic acid

[0071] The crystallizer contents were heated above 95°C to dissolve all solids and form a homogeneous solution. The solution was then cooled to 40°C with stirring to obtain a slurry of adipic acid crystals o...

example 3

[0077] This example illustrates the recovery of crude adipic acid from the process of the invention when the concentration of valerolactone in the reaction mixture is 50% by weight. The hydrocarboxylation reaction was carried out as described in Example 1, except that the concentration of valerolactone in the reaction mixture was 50% by weight. A 500 g sample of the product stream was placed in a 1 liter glass crystallizer equipped with a magnetic stirrer and a total reflux condenser (20°C). The product stream mixture comprises (by weight):

[0078] 50% gamma-valerolactone

[0079] 25% adipic acid

[0080] 16% 2-methylglutaric acid

[0081] 2.6% Citric Acid

[0082] 3.5% valeric acid

[0083] 1.3% 2-methylbutyric acid

[0084] 1% caproic acid

[0085] 0.6% 3-pentenoic acid

[0086] The concentration of monobasic acid impurities co-crystallized in the adipic acid crystals was 127 ppm valeric acid and 215 ppm hexanoic acid. The adipic acid crystals formed in Example 2 h...

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Abstract

This invention provides a process for the preparation of adipic acid from pentenoic acids or esters of pentenoic acids by hydrocarboxylation of a reaction mixture in which gamma-valerolactone constitutes 30 to 70% by weight of the reaction mixture.

Description

field of invention [0001] The present invention relates to a process for the preparation of adipic acid. Background of the invention [0002] One method that can be used to synthesize adipic acid is through the hydrocarboxylation of pentenoic acids and esters. In US Patent Nos. 4,788,333 and 4,788,334 Burke teaches that a process for preparing adipic acid involves the hydrocarboxylation of pentenoic acids and their esters. Pentenoic acids and their esters, especially 3-pentenoic acid and its esters, are readily obtained from butadiene and butadiene-derived starting materials by metal-catalyzed hydrocarboxylation. The preparation of adipic acid from these raw materials has the potential to provide a high-yield, high-speed and low-pollution process for the industrial preparation of adipic acid. [0003] In the hydrocarboxylation of 3-pentenoic acid and its esters (hereinafter referred to as pentenoic acid), high levels of branched products are undesirable. Burke (US Pat. No...

Claims

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Application Information

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IPC IPC(8): C07C51/14C07C51/10C07C55/14C07C67/38
CPCC07C67/38C07C51/10C07C55/14C07C69/44C07C51/14
Inventor 小H·S·布鲁纳S·L·莱恩B·E·默弗里
Owner EI DU PONT DE NEMOURS & CO
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