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Process for the preparation of a dicarboxylic acid

A technology of dicarboxylic acid and conjugated diene, applied in the field of preparing dicarboxylic acid, can solve problems such as not very fast and not suitable for industrial application

Inactive Publication Date: 2008-03-12
SHELL INT RES MAATSCHAPPIJ BV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But neither reaction step has been found to be very fast, which makes the method less suitable for industrial applications

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1 - Semi-continuous reaction for the preparation of pentenoic acid from butadiene

[0044] Into a 1.2 liter mechanically stirred autoclave were charged 130 g pentenoic acid, 1.55 g water and 10 g tetradecane. The autoclave was purged three times with CO at 3.0 MPa. The autoclave was then pressurized to 5.0 MPa with CO, and 5 g of butadiene was added to the reactor. A solution of 0.1 mmol of palladium acetate and 0.3 mmol of 1,2-bis(di-tert-butylphosphinomethyl)benzene dissolved in 10 g of pentenoic acid was then injected as catalyst components. The syringe was flushed with an additional 10 g of pentenoic acid.

[0045] Then, butadiene and water were continuously added to the reactor at a flow rate of 60 mmol / h under stirring conditions, and the reactor was heated to 140° C. within 30 minutes. When this temperature was reached, the pressure was adjusted to 8.0 MPa, and the reactor was maintained at these conditions for 45 hours, taking samples at regular inter...

Embodiment 2

[0049] Example 2 - Semi-continuous reaction for in situ conversion of esters of butadiene and pentenoic acid

[0050] Into a 1.2 liter mechanically stirred autoclave were charged 165 g pentenoic acid, 30 g adipic acid and 3.8 g tetradecane. The autoclave was purged three times with carbon monoxide at 3.0 MPa. The autoclave was then pressurized to 1.0 MPa with carbon monoxide, and 25 g of butadiene was added. The catalyst system was then injected into the reactor: a solution of 0.5 mmol of palladium acetate and 1.0 mmol of 1,2-bis(di-tert-butylphosphinomethyl)benzene dissolved in 10 g of pentenoic acid. The syringe was flushed with an additional 10 g of pentenoic acid. Then, butadiene was continuously fed into the reactor at a flow rate of 125 mmol / h, while the reactor was heated to 105° C. within 30 minutes. When this temperature was reached, the pressure was adjusted to 8.0 MPa. The reactor was kept under agitation at these conditions for 15 hours and samples were taken at ...

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PUM

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Abstract

A process for the preparation of a saturated dicarboxylic acid, comprising the steps of (a) contacting a conjugated diene with carbon monoxide and water to obtain a mixture containing an ethylenically unsaturated acid product and one or more reversible adducts of the conjugated diene and the ethylenically unsaturated acid; and (b) reacting the ethylenically unsaturated acid product further with carbon monoxide and water to obtain the dicarboxylic acid, wherein step (a) and (b) are performed in the presence of a catalyst system including a source of palladium, a source of an anion and a bidentate phosphine ligand, and wherein in step (a) the water concentration is maintained at a range of from 0.001 to less than 3% by weight of water, calculated on the overall weight of the liquid reaction medium, and wherein in step (b) the water concentration is maintained at a range of from 3% to 50% by weight of water, calculated on the overall weight of the liquid reaction medium.

Description

technical field [0001] The present invention provides a process for the preparation of dicarboxylic acids by carbonylation of conjugated dienes. Background technique [0002] Carbonylation reactions of conjugated dienes are well known in the art. In the present specification, the term carbonylation refers to the reaction of conjugated dienes under the catalysis of transition metal complexes in the presence of carbon monoxide and water, as described, for example, in WO 04 / 103948. [0003] In WO 04 / 103948 a process for the preparation of adipic acid in a two-stage reaction from 1,3-butadiene or a mixture of 1,3-butadiene and olefinic products is disclosed. In the first stage of the disclosed process, in the presence of a carbonylation catalyst comprising a palladium compound, a source of anions, and 1,2-bis(di-tert-butylphosphinomethyl)benzene as a bidentate diphosphorus ligand The 1,3-butadiene is reacted with carbon monoxide and water for several hours until substantially ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/14C07C57/03C07C55/02C07F9/50C07C55/14B01J31/24
CPCB01J2531/824C07C51/14B01J31/24C07C57/03C07C55/14
Inventor 艾特·迪伦特芮内·恩斯特威廉·伟伯·杰格科妮莉亚·艾莉达·克罗姆
Owner SHELL INT RES MAATSCHAPPIJ BV