Derivative of epichlorohydrin of natural origin

Patent metadata

Field	Value
Publication number	US-9309209-B2
Application number	US-201113876003-A
Country	US
Kind code	B2
Filing date	Sep 26, 2011
Priority date	Sep 30, 2010
Publication date	Apr 12, 2016
Grant date	Apr 12, 2016

Abstract

Derivative of epichlorohydrin of natural origin, selected from the group consisting of glycidyl ethers presenting an epoxide equivalent weight higher than or equal to 50 g/equivalent and lower than or equal to 15000 g/equivalent, of glycidyl esters, of glycidyl amides, of glycidyl imides, of glycidyl amines, and of any mixture thereof, and of which the 14 C mass content is such that the ratio 14 C/ 12 C is higher than 0.7 10 −12 .

First claim

The invention claimed is:

1. A derivative of natural origin, selected from the group consisting of glycidyl ethers,
wherein said glycidyl ethers present an epoxide equivalent weight higher than or equal to 50 g/equivalent and lower than or equal to 15000 g/equivalent, and
wherein said derivative is obtained from epichlorohydrin of natural origin and from at least one compound containing at least one active hydrogen atom, at least one part of said compound having been obtained from renewable raw materials, the natural origin of the derivative resulting in a 14 C mass content of said derivative which is such that the ratio of 14 C/ 12 C is higher than 0.7×10 −12 .

2. The derivative of natural origin according to claim 1 wherein said glycidyl ether further exhibits characteristics selected from the group consisting of
an epoxy value in equivalent per 100 g of derivative higher than or equal to 0.008 and lower than or equal to 1.0,
a dynamic viscosity at 25° C. higher than or equal to 50 mPa·s and lower than or equal to 50000, a content of hydrolysable chloride higher than or equal to 0.01% and lower than or equal to 2.2%, and any combination thereof.

3. The derivative of natural origin according to claim 2 wherein said glycidyl ether exhibits an epoxy value in equivalent per 100 g of derivative higher than or equal to 0.008 and lower than or equal to 1.0.

4. The derivative of natural origin according to claim 2 wherein said glycidyl ether exhibits a dynamic viscosity at 25° C. higher than or equal to 50 mPa·s and lower than or equal to 50000.

5. The derivative of natural origin according to claim 2 wherein said glycidyl ether exhibits a content of hydrolysable chloride higher than or equal to 0.01% and lower than or equal to 2.2%.

6. The derivative of natural origin according to claim 1 wherein said glycidyl ether is a polyglycidyl ether.

7. The derivative of natural origin according to claim 6 wherein said polyglycidyl ether is a polyglycidyl ether polymer.

8. The derivative of natural origin according to claim 1 , wherein the 14 C mass content of said derivative of natural origin is such that the ratio 14 C/ 12 C is equal to 1.2×10 −12 .

9. A method for using a derivative of epichlorohydrin of natural origin according to claim 1 .

10. A process for manufacturing the derivative of natural origin according to claim 1 comprising reacting epichlorohydrin of natural origin with at least one compound having at least one active hydrogen atom, at least one part of said compound having been obtained from renewable raw materials.

11. The process according to claim 10 , wherein said epichlorohydrin ratio 14 C/ 12 C and said compound ratio 14 C/ 12 C are such that
[ X epi ( 14 C/ 12 C) epi +X cpd ( 14 C/ 12 C) cpd ]>0.7×10 −12

wherein X epi is the fraction of C atoms from epichlorohydrin in said derivative of natural origin,
X cpd is the fraction of C atoms from said compound in said derivative of natural origin,
( 14 C/ 12 C) epi is the carbon 14 to carbon 12 isotopic ratio in said epichlorohydrin, and
( 14 C/ 12 C) cpd is the carbon 14 to carbon 12 isotopic ratio in said compound.

12. The process according to claim 11
wherein the ( 14 C/ 12 C) epi is higher than or equal to 0.2×10 −12 , and
wherein the ( 14 C/ 12 C) cpd is higher than or equal to 0.2×10 −12 .

13. The process according to claim 12 wherein the ( 14 C/ 12 C) epi s equal to 1.2×10 −12 , and wherein the ( 14 C/ 12 C) cpd is equal to 1.2×10 −12 .

14. The process according to claim 11 , wherein said epichlorohydrin is obtained by dehydrochlorination of dichloropropanol, said dichloropropanol is produced by reaction between glycerol and hydrogen chloride,
wherein at least one part of said glycerol is prepared in a conversion process of renewable raw materials, or obtained in the manufacture of biodiesel, or obtained in at least one of the manufacture of soaps, fatty acids and fatty alcohols,
wherein said conversion process of renewable raw materials is selected from the group consisting of hydrolysis, saponification, transesterification, aminolysis and hydrogenation of oils and/or fats of animal, plant and/or algae, fermentation, hydrogenation, and hydrogenolysis of mono- and polysaccharides and alcohols occurring naturally in the biomass, and any combination thereof.

15. The process according to claim 11 , wherein at least one part of said compound having at least one active hydrogen atom is obtained from renewable raw materials, and
wherein the compound having at least one active hydrogen atom is selected from the group consisting of a monoalcohol, a polyol having more than three carbon atoms, an amino alcohol, an acid mono- or polyphenol and any mixture thereof, and
wherein said polyol contains more than three carbon atoms is selected from the group consisting of a polyphenol, a sugar, a polyol derived from a sugar, an acid polyphenol, and any mixture thereof, and
wherein said polyol derived from a sugar is selected from the group consisting of an anhydrosugar, a reduction product from a sugar, a reduction product of hydroxymethylfurfural, a difuran derivative of furfural, and any mixture thereof, and
wherein said difuran derivative of furfural is selected from the group consisting of 5,5′-methylene-bis-2-furanmethanol, 5,5′-isopropylidene-bis-2-furanmethanol, and any mixture thereof.

16. The process according to claim 15 wherein said anhydrosugar is selected from the group consisting of isosorbide, isomannide, isoidide and any mixture thereof.

17. The process according to claim 16 wherein the anhydrosugar is isosorbide.

Assignees

• Gilbeau Patrick
• Solvay

Inventors

• Gilbeau Patrick

Classifications

• C07D301/26 Primary

  Y being hydrogen · CPC title

• C07D303/40

  by ester radicals · CPC title

• C07D303/18

  by etherified hydroxyl radicals · CPC title

• C07D303/08 Primary

  with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals · CPC title

• C07D303/46

  by amide or nitrile radicals · CPC title