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Selective extraction of an omega-functionalised acid after oxidative cleavage of an unsaturated fatty acid and derivatives

An unsaturated fatty acid, selective technology, applied in the field of selective extraction of ω-functionalized acids after oxidative cracking of unsaturated fatty acids and derivatives, can solve difficult and complicated removal problems

Inactive Publication Date: 2015-07-22
ARKEMA FRANCE SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the described case, the composition of the cleavage reaction product and the starting saturated product is more complex than that described in the cited document, containing a significantly larger amount of reaction by-products and non-reactive residual products, which making their removal more difficult and complex than that described in the literature

Method used

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  • Selective extraction of an omega-functionalised acid after oxidative cleavage of an unsaturated fatty acid and derivatives
  • Selective extraction of an omega-functionalised acid after oxidative cleavage of an unsaturated fatty acid and derivatives
  • Selective extraction of an omega-functionalised acid after oxidative cleavage of an unsaturated fatty acid and derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Example 1 : Extraction of 8-cyanoctanoic acid from reaction mixture R1 derived from oxidative cleavage of oleic acid nitrile

[0065] The reaction mixture R1 used was a solution (according to gas chromatographic analysis) with a composition as presented in Table 2 below.

[0066] Table 2 : combination of reaction mixture R1

[0067] Components of reaction mixture R1

weight%

mmol / g

nonanal

0.7

0.049

Heptanoic acid (A7)

1.9

0.146

Caprylic acid (A8)

1.2

0.080

Nonanoic Acid (A9)

12.4

0.785

Capric acid (A10)

0.5

0.028

7-cyanoheptanoic acid (7CHA)

1.6

0.105

8-cyanoctanoic acid (8COA)

19.8

1.169

9-Cyanononanoic Acid (9CNA)

1.0

0.053

Myristonitrile (14:0)

1.7

0.080

10-cyanodecanoic acid (10CDA)

1.2

0.062

Palmitic acid nitrile (16:0)

4.3

0.182

Stearic acid nitrile (18:0)

1.8

0.068 ...

Embodiment 2

[0085] Example 2 : Extraction of diacid (Azelaic acid: AZ) from reaction mixture R2 obtained by oxidative cleavage of oleic acid

[0086] The reaction for the oxidative cleavage of oleic acid proceeds in a similar manner to the oxidative cleavage of oleic acid nitrile (with oleic acid nitrile being replaced by oleic acid). The oleic acid used was Oleon with a purity of 75%. The reaction takes place at 70 °C with no gas flow and using pure H with 144% relative to pure oleic acid 2 o 2 .

[0087] A sample of the reaction mixture R2 derived from the oxidative cleavage of oleic acid was extracted with the following solvent mixture: acetic acid (AA) / water, corresponding to AA / water = 58 / 42 by weight.

[0088] A weight of 2.1 g of the solution (R2) derived from the oxidative cleavage was brought into contact with a weight of 24.9 g of the AA / water solvent mixture. Thus, azelaic acid, which was initially present at 36.9%, was extracted by this solvent mixture. The composition ...

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Abstract

The invention concerns a method for the selective extraction of a reaction product, originating from an oxidative cleavage of an unsaturated fatty acid or of an ester derivative or of an unsaturated nitrile derivative, said reaction product being a co-functionalised acid chosen from the C6 to C15 diacids, ester-acids and nitrile-acids, using, as the selective extraction solvent, a composition comprising a mixture of water and C1-C4 carboxylic acid. The invention also concerns the use of said method and the extraction solvent composition for the preparation of C6 to C15 amino acid, diacid or ester-acid monomers for the production of polycondensation polymers, in particular polyamides.

Description

[0001] The work carried out leading to the present invention was supported by European Union project number 241718EUROBIOREF within the Seventh Framework Program (FP7 / 2007-2013). technical field [0002] The present invention relates to the selective extraction of ω-functionalized C from reaction mixtures using specific mixtures as selective extraction solvents 6 -C 15 Aliphatic acid method, the omega-functionalized C 6 -C 15 Aliphatic acids bearing acid or ester or nitrile functional groups in the ω position, which are respectively diacids, acid-esters or acid-nitriles (or cyano acids), the reaction mixture is especially regenerated in oxidative cleavage and of industrial quality Unsaturated fatty acids or their ester derivatives (natural oils) or their nitrile derivatives are obtained after the specific mixture as selective extraction solvent is based on water with a specific water-acid ratio and at least one C 1 -C 4 carboxylic acid and more specifically C 1 -C 3 A mi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/34C07C51/34C07C51/48
CPCC07C253/34C07C51/34C07C51/48C07C55/18
Inventor M.布兰德霍斯特
Owner ARKEMA FRANCE SA
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