Method for the treatment of a composition comprising natural vanillin

Patent metadata

Field	Value
Publication number	US-12152002-B2
Application number	US-202017627153-A
Country	US
Kind code	B2
Filing date	Jul 30, 2020
Priority date	Jul 30, 2019
Publication date	Nov 26, 2024
Grant date	Nov 26, 2024

Abstract

The present invention relates to a process for treating a composition comprising natural vanillin by separating a compound of formula (I).

First claim

The invention claimed is:

1. A process for treating a composition (C) resulting from a process for producing natural vanillin, the vanillin comprising natural vanillin and vanillyl alcohol, said treatment process comprising:
a step (i) of forming a composition (C1) comprising natural vanillin and a compound of formula (I) formed via an etherification or esterification reaction from said vanillyl alcohol present in composition (C):

wherein n is equal to 0 or 1, and R is chosen from a linear or branched, saturated or unsaturated alkyl group, optionally substituted with at least one hydroxyl, alkoxy or amine group, or R is a group of formula —(W—O) m —X, wherein W is a linear or branched alkyl chain comprising from 1 to 4 carbon atoms and the average molecular weight of the —(W—O) m —X group is between 200 and 3000 g/mol and X is chosen from H and a unit of formula (II), and

a step (ii) of recovering said natural vanillin and/or a step of recovering said compound of formula (I) present in composition (C1).

2. The treatment process of claim 1 , wherein step (i) is carried out in the presence of a compound chosen from the group consisting of ROH, RCOOH, and HO—(W—O) m —H, wherein R is chosen from a linear or branched, saturated or unsaturated alkyl group, optionally substituted with at least one hydroxyl, alkoxy or amine group and W is a linear or branched alkyl chain comprising from 1 to 4 carbon atoms and the average molecular weight of the HO—(W—O) m —H compound is between 200 and 3000 g/mol.

3. The treatment process of claim 1 , wherein step (i) also enables the formation of a compound of formula (III), according to the following formula, from vanillic acid present in composition (C):

wherein n is equal to 0 or 1, and R is chosen from a linear or branched, saturated or unsaturated alkyl group, optionally substituted with at least one hydroxyl, alkoxy or amine group, or a group of formula —(W—O) m —X, wherein W is a linear or branched alkyl chain comprising from 1 to 4 carbon atoms and the average molecular weight of the —(W—O) m —X group is between 200 and 3000 g/mol and X is chosen from H and a unit of formula (IV)

4. The treatment process of claim 1 , wherein step (i) is an etherification reaction carried out in the presence of a compound of formula ROH, R being a butyl group, and wherein step (ii) is a step of recovering natural vanillin and of recovering a compound of formula (I) having n=0 and R being a butyl group.

5. The treatment process of claim 1 , wherein the natural vanillin obtained at the end of step (ii) comprises less than 500 ppm of vanillyl alcohol.

6. The treatment process of claim 1 , wherein the composition of the natural vanillin obtained at the end of step (ii) comprises less than 200 ppm of 4-((4-hydroxy-3-methoxybenzyl)oxy)-3-methoxybenzaldehyde or 4-hydroxy-3-(4-hydroxy-3-methoxybenzyl)-5-methoxybenzaldehyde.

7. The treatment process of claim 1 , comprising an additional step (iii) wherein the natural vanillin obtained at the end of step (ii) is shaped in the form of crystals, beads, pearls, or powder.

8. The treatment process of claim 1 , having a purification yield of greater than or equal to 90% relative to the amount of natural vanillin in composition (C).

9. The treatment process of claim 1 , wherein the vanillin titer in the natural vanillin composition obtained at the end of step (ii) or (iii) is greater than or equal to 95%.

10. The treatment process of claim 1 , wherein the natural vanillin obtained at the end of step (ii) or (iii) has a color of less than or equal to 400 Hazen.

11. A composition comprising:
a compound of formula (I)

wherein n is equal to 0 or 1, and R is chosen from a linear or branched, saturated or unsaturated alkyl group comprising from 1 to 10 carbon atoms, optionally substituted with at least one hydroxyl, alkoxy or amine group, or R is a group of formula —(W—O) m —X, wherein W is a linear or branched alkyl chain comprising from 1 to 4 carbon atoms and the average molecular weight of the —(W—O) m —X group is between 200 and 3000 g/mol and X is chosen from H and a unit of formula (II); and
4-((4-hydroxy-3-methoxybenzyl)oxy)-3-methoxybenzaldehyde and/or 4-hydroxy-3-(4-hydroxy-3-methoxybenzyl)-5-methoxybenzaldehyde in an amount less than 200 ppm and greater than or equal to 0.01 ppm.

12. The composition of claim 11 , wherein the compound of formula (I) is naturally produced.

13. The composition of claim 11 , wherein the amount of 4-((4-hydroxy-3-methoxybenzyl)oxy)-3-methoxybenzaldehyde and/or 4-hydroxy-3-(4-hydroxy-3-methoxybenzyl)-5-methoxybenzaldehyde is greater than or equal to 0.1 ppm.

14. The composition of claim 11 , wherein n=0 and R=ethyl or butyl.

15. The treatment process of claim 1 , wherein the recovering of step (ii) further comprises separating the natural vanillin from the compound of formula (I).

16. The treatment process of claim 1 , wherein the recovered natural vanillin has a purification yield of greater than or equal to 75%.

17. The treatment process of claim 1 , wherein, when the compound of formula (I) is recovered, the compound of formula (I) has a natural vanillin content less than or equal to 200 ppm.

18. The treatment process of claim 1 , wherein R is an alkyl group comprising from 1 to 10 carbon atoms.

Assignees

• Specialty Operations France

Inventors

• Garel Laurent
• Djillali Rachid

Classifications

• C12P7/24

  containing a carbonyl group · CPC title

• C07C45/85

  by treatment giving rise to a chemical modification (by chemisorption C07C45/79) · CPC title

• C11D3/50

  Perfumes · CPC title

• A61Q13/00

  Formulations or additives for perfume preparations (essential oils or perfumes per se C11B9/00) · CPC title

• A61Q1/00

  Make-up preparations; Body powders; Preparations for removing make-up · CPC title