IP Library Granted Patent US 11,534,743
Granted Patent B2
US 11,534,743 · App. 16/463,534 · Granted Dec 27, 2022

Acid composition for processing fatty acids

Inventors: Jean-Alex Laffitte (Pau, FR); Bernard Monguillon (Bayonne, FR); Vijay Srinivas (Exton, PA)
Assignee: ARKEMA FRANCE
B01J31/0225C07C67/03B01J2231/49
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Quick Facts
Patent No.
US 11,534,743
App. No.
16/463,534
Granted
Dec 27, 2022
Kind
B2
Abstract

The invention relates to a composition comprising: at least one alkane-sulphonic acid R—SO 3 H wherein R represents a saturated, linear or branched, hydrocarbon chain comprising from 1 to 4 carbon atoms, which can or cannot be substituted by at least one halogen atom; sulphuric acid; and optionally at least one solvent; of which the proportions are defined in the description. The invention also relates to the use of the composition as a fatty acid esterification catalyst.

Claims (31)

1. A composition comprising:

one or more alkane-sulphonic acids of formula R—SO 3 H wherein R represents a saturated, linear or branched, hydrocarbon chain comprising from 1 to 4 carbon atoms;

sulphuric acid;

and optionally at least one solvent;

wherein:

the proportion by weight of alkane-sulphonic acid in relation to the total weight of the alkane-sulphonic acid and sulphuric acid is comprised between 40% and 90%;

the proportion by weight of sulphuric acid in relation to the total weight of the alkane-sulphonic acid and sulphuric acid is comprised between 10% and 60%;

the proportion by weight of solvent relative to the total weight of the composition is comprised between 0% and 50%; and

the one or more alkane-sulphonic acids comprises methane-sulphonic acid.

2. The composition according to claim 1 wherein the solvent is chosen among water, alcohol and ether, alone or in combination.

3. The composition according to claim 1 wherein the solvent is water or a C 1 to C 3 alcohol, alone or in combination.

4. The composition according to claim 1 wherein the solvent is water or methanol, alone or in combination.

5. The composition according to claim 1 wherein the proportion by weight of solvent relative to the total weight of the composition is comprised between 5% and 35%.

6. A composition according to claim 1 , wherein the composition further comprises at least one corrosion inhibitor.

7. A composition according to claim 1 comprising at least one fragrance or one odorising agent, alone or in combination.

8. A method for manufacturing fatty acid esters comprising the following steps:

a/ placing at least one fatty acid into a reactor;

b/ adding at least one alcohol;

c/ heating the reaction medium;

d/ introducing the composition according to claim 1 as a catalyst;

e/ optionally, removing the water formed during the esterification reaction; and

f/ recovering the fatty acid esters

with step d being optionally performed at the same time as step a and/or step b.

9. The method according to claim 8 wherein the catalyst/fatty acid molar ratio is comprised within a range of from 0.001 to 1.

10. The composition according to claim 1 , wherein the proportion by weight of alkane-sulphonic acid in relation to the total weight of the alkane-sulphonic acid and sulphuric acid is comprised between 44% and 89%, and wherein the proportion by weight of sulphuric acid in relation to the total weight of the alkane-sulphonic acid and sulphuric acid is comprised between 11% and 56%.

11. The composition according to claim 10 , wherein the proportion by weight of solvent relative to the total weight of the composition is comprised between 5% and 35%.

12. The method of claim 8 wherein step d is performed at the same time as step a and/or step b.

13. The method according to claim 8 wherein the catalyst/fatty acid molar ratio is comprised within a range of from 0.01 to 0.5.

14. The method according to claim 8 wherein the catalyst/fatty acid molar ratio is comprised within a range of from 0.02 to 0.2.

15. The composition according to claim 1 wherein the one or more alkane-sulphonic acids, in addition to the methane-sulphonic acid, includes one or more, in any combination and in any mixture proportion, of ethane-sulphonic acid, n-propane-sulphonic acid, iso-propane-sulphonic acid, n-butanesulphonic acid, iso-butanesulphonic acid, sec-butane-sulphonic acid, tert-butanesulphonic acid.

16. The composition according to claim 1 wherein the one or more alkane-sulphonic acids is limited to the methane-sulphonic acid.

Assignments (2)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 17, 2019
From: LAFFITTE, JEAN-ALEX; MONGUILLON, BERNARD; SRINIVAS, VIJAY
To: ARKEMA FRANCE
Reel/Frame 049784/0432 →