Hydroformylation of triglycerides in a self-emulsifying medium

Patent metadata

Field	Value
Publication number	US-9556402-B2
Application number	US-201415035556-A
Country	US
Kind code	B2
Filing date	Nov 7, 2014
Priority date	Nov 12, 2013
Publication date	Jan 31, 2017
Grant date	Jan 31, 2017

Abstract

The invention relates to a method for the hydroformnylation of triglycerides by homogeneous catalysis in the presence of at least one substituted cyclodextrin, said method comprising a step a) of combining, under agitation, at least one catalyst, waiter, at least one unsaturated triglyceride and said substituted cyclodextrin, in the presence of gaseous hydrogen and carbon monoxide, said step being carried out in reactive conditions allowing the formation of an emulsion during the agitation and a decanting of the products once the agitation has stopped.

First claim

The invention claimed is:

1. A process for the hydroformylation of triglycerides by homogeneous catalysis in the presence of at least one substituted cyclodextrin, the process comprising:
a step a) of bringing together, with stirring, at least one catalyst, water, at least one unsaturated triglyceride and the substituted cyclodextrin, in the presence of hydrogen gas and of carbon monoxide; and
wherein the step is carried out under reaction conditions allowing the formation of an emulsion during the stirring and decanting of the reaction products once the stirring has stopped.

2. The process as claimed in claim 1 , wherein the substituted cyclodextrin is an α, β or γ-cyclodextrin.

3. The process as claimed in claim 1 , wherein the substituted cyclodextrin is a methylated cyclodextrin.

4. The process as claimed in claim 3 , wherein the methylated cyclodextrin has an average degree of substitution ranging from 0.5 to 2.

5. The process as claimed in claim 1 , wherein the substituted cyclodextrin is a hydroxypropylated cyclodextrin.

6. The process as claimed in claim 5 , wherein the hydroxypropylated cyclodextrin has an average degree of substitution ranging from 0.5 to 2.0.

7. The process as claimed in claim 1 , that wherein step a) is carried out at a temperature ranging from 40° C. to 120° C.

8. The process as claimed in claim 1 , wherein the cyclodextrin/triglyceride mole ratio is chosen in a range of from 0.2 to 4.

9. The process as claimed in claim 1 , wherein step a) is carried out under pressure of a gas comprising molecular hydrogen and carbon monoxide and in that the gas pressure is greater than or equal to 80 bar.

10. The process as claimed in claim 1 , wherein the catalyst is a complex comprising a transition metal combined with a sulfonated phosphine.

11. The process as claimed in claim 1 , wherein the triglyceride is a mixture of triglycerides, which mixture does not comprise more than 10 mol % of polyunsaturated fatty chains in the triglycerides.

12. The process as claimed in claim 1 , wherein the reaction conditions are close to, or are those of, the catalysis carried out in the presence of cyclodextrin.

13. The process as claimed in claim 1 , wherein the decanting allows the separation of an organic phase containing the reaction products and that the step of recovering the reaction products is carried out by separation of the reaction medium from the phase.

14. The process as claimed in claim 4 , wherein the methylated cyclodextrin has an average degree of substitution of 0.8.

15. The process as claimed in claim 6 , wherein the hydroxypropylated cyclodextrin has an average degree of substitution of 0.8.

16. The process as claimed in claim 7 , wherein step a) is carried out at a temperature ranging from 60° C. to 80° C.

17. The process as claimed in claim 8 , wherein the cyclodextrin/triglyceride mole ratio is 2.9.

18. The process as claimed in claim 10 , wherein the sulfonated phosphine is selected from the group consisting of TPPTS and a sulfonated phenyl(s)/biphenyl(s) phosphine.

Assignees

• Pivert
• Centre Nat De La Rech Scient (Cnrs)
• Univ D'Artois

Inventors

• Hapiot Frédéric
• Monflier Eric
• Vanbesien Théodore

Classifications

• C11C3/126

  using catalysts based principally on other metals or derivates · CPC title

• C07C67/313

  by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups · CPC title

• C11C3/00 Primary

  Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom (sulfonated fats or oils C07C309/62; factice C08H; drying oils C09F) · CPC title

• C07C67/347

  by addition to unsaturated carbon-to-carbon bonds · CPC title