IP Library Granted Patent US 11,484,052
Granted Patent B2
US 11,484,052 · App. 16/634,823 · Granted Nov 1, 2022

Vanillin and/or ethylvanillin, process for their preparations and use thereof

Inventors: Stephan Verdier (Lyons, FR); Frédéric Madelaine (Cincinnati, OH)
Assignee: RHODIA OPERATIONS
A23L27/204A61K31/11
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Quick Facts
Patent No.
US 11,484,052
App. No.
16/634,823
Granted
Nov 1, 2022
Kind
B2
Abstract

The present invention relates to a new bio-sourced vanillin and/or ethylvanillin, containing specific impurities. The invention further relates to a process for their preparations and the use of such compounds.

Claims (34)

1. A composition, comprising vanillin and/or ethylvanillin, and at least one compound selected from the group consisting of 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid, 4-hydroxy-5-methoxyisophthalaldehyde, 2,2′-(4-hydroxy-5-methoxy-1,3-phenylene)bis(2-hydroxyacetic acid), 2-hydroxy-3-methoxybenzaldehyde, 2-hydroxy-2-(2-hydroxy-3-methoxyphenyl)acetic acid, 2-(3-ethoxy-4-hydroxyphenyl)-2-hydroxyacetic acid, 2-(3-ethoxy-2-hydroxyphenyl)-2-hydroxyacetic acid, 2,2′-(5-ethoxy-4-hydroxy-1,3-phenylene)bis(2-hydroxyacetic acid), 5-ethoxy-4-hydroxyisophthalaldehyde, 3-ethoxy-2-hydroxybenzaldehyde, (E or Z)-3-(4-hydroxy-3-methoxybenzylidene)-7-methoxybenzofuran-2(3H)-one, (E or Z)-7-ethoxy-3-(3-ethoxy-4-hydroxybenzylidene)benzofuran-2(3H)-one, 4-hydroxy-3-methylbenzaldehyde, and 4-hydroxy-3,5-dimethylbenzaldehyde,

wherein the vanillin and/or ethylvanillin has a purity higher than 90% and a bio-based carbon content of between 75% and 100%, and

wherein the vanillin and/or ethylvanillin exhibits a mean isotopic 13 C deviation of from 33‰ to −23‰.

2. The composition according to claim 1 , wherein vanillin and/or ethylvanillin has a bio-based carbon content above 80%.

3. The composition according to claim 1 wherein the vanillin and/or ethylvanillin is not directly produced from lignin or biomass.

4. The composition according to claim 1 , wherein the composition comprises vanillin and the at least one compound is selected from the group consisting of 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid, 4-hydroxy-5-methoxyisophthalaldehyde, 2,2′-(4-hydroxy-5-methoxy-1,3-phenylene)bis(2-hydroxyacetic acid), 2-hydroxy-3-methoxybenzaldehyde, 2-hydroxy-2-(2-hydroxy-3-methoxyphenyl)acetic acid, (E or Z)-3-(4-hydroxy-3-methoxybenzylidene)-7-methoxybenzofuran-2(3H), 4-hydroxy-3-methylbenzaldehyde, and 4-hydroxy-3,5-dimethylbenzaldehyde.

5. The composition according to claim 1 , wherein the composition comprises vanillin having a purity higher than 95%.

6. The composition according to claim 4 , wherein the amount of the at least one compound is between 1 and 5000 ppm.

7. The composition according to claim 1 , wherein the composition comprises vanillin and is in the form of flakes, beads, prills, or powder.

8. The composition according to claim 1 , wherein the composition comprises vanillin and the composition exhibits satisfactory organoleptic properties.

9. The composition according to claim 1 , wherein the composition comprises ethylvanillin and the at least one compound is selected from the group consisting of 2-(3-ethoxy-4-hydroxyphenyl)-2-hydroxyacetic acid, 2-(3-ethoxy-2-hydroxyphenyl)-2-hydroxyacetic acid, 2,2′-(5-ethoxy-4-hydroxy-1,3-phenylene)-bis(2-hydroxyacetic acid), 5-ethoxy-4-hydroxyisophthalaldehyde, 3-ethoxy-2-hydroxybenzaldehyde, and (E or Z)-7-ethoxy-3-(3-ethoxy-4-hydroxybenzylidene)-benzofuran-2(3H)-one.

10. The composition according to claim 1 , wherein the composition comprises ethylvanillin having a purity higher than 95%.

11. The composition according to claim 9 , wherein the composition comprises ethylvanillin and the amount of the at least one compound is between 1 ppm and 5000 ppm.

12. The composition according to claim 1 , wherein the composition comprises ethylvanillin and is in the form of flakes, beads, prills or powder.

13. A process for the preparation of a composition that comprises vanillin and/or ethylvanillin having a bio-based carbon content of between 75% and 100% and exhibits a mean isotopic 13 C deviation of from −33‰ to −23‰, comprising:

(a) condensing guaiacol and/or guetol that has a bio-based carbon content is between 75% and 100%, with glyoxylic acid to obtain a condensation product, and

(b) oxidizing the condensation product,

wherein the composition further comprises:

at least one compound selected from the group consisting of 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid, 4-hydroxy-5-methoxyisophthalaldehyde, 2,2′-(4-hydroxy-5-methoxy-1,3-phenylene)bis(2-hydroxyacetic acid), 2-hydroxy-3-methoxybenzaldehyde, 2-hydroxy-2-(2-hydroxy-3-methoxyphenyl)acetic acid, 2-(3-ethoxy-4-hydroxyphenyl)-2-hydroxyacetic acid, 2-(3-ethoxy-2-hydroxyphenyl)-2-hydroxyacetic acid, 2,2′-(5-ethoxy-4-hydroxy-1,3-phenylene)bis(2-hydroxyacetic acid), 5-ethoxy-4-hydroxyisophthalaldehyde, 3-ethoxy-2-hydroxybenzaldehyde, (E or Z)-3-(4-hydroxy-3-methoxybenzylidene)-7-methoxybenzofuran-2(3H)-one, and (E or Z)-7-ethoxy-3-(3-ethoxy-4-hydroxybenzylidene)benzofuran-2(3H)-one, 4-hydroxy-3-methylbenzaldehyde, and 4-hydroxy-3,5-dimethylbenzaldehyde.

14. A process for the preparation of a composition comprising vanillin and/or ethylvanillin according to claim 1 comprising:

(a) condensing guaiacol having a bio-based carbon content of between 75% and 100%, and/or guetol having a bio-based carbon content of between 75% and 100%, with glyoxylic acid to obtain a condensation product, and

(b) oxidizing the condensation product.

15. A process according to claim 13 , wherein glyoxylic acid has a bio-based carbon content of above 50%.

16. A process according to claim 13 , wherein the mole ratio of the guaiacol and/or guetol to the glyoxylic acid is between 1.0 and 4.0.

17. A food, cosmetic or pharmaceutical composition comprising a vanillin and/or composition according to claim 1 as a flavor or fragrance.

18. A composition comprising:

vanillin and/or ethylvanillin having a bio-based carbon content of between 75% and 100% and exhibits a mean isotopic 13 C deviation of from −33‰ to −23‰; and

at least one compound selected from the group consisting of 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid, 4-hydroxy-5-methoxyisophthalaldehyde, 2,2′-(4-hydroxy-5-methoxy-1,3-phenylene)bis(2-hydroxyacetic acid), 2-hydroxy-3-methoxybenzaldehyde, 2-hydroxy-2-(2-hydroxy-3-methoxyphenyl)acetic acid, 2-(3-ethoxy-4-hydroxyphenyl)-2-hydroxyacetic acid, 2-(3-ethoxy-2-hydroxyphenyl)-2-hydroxyacetic acid, 2,2′-(5-ethoxy-4-hydroxy-1,3-phenylene)bis(2-hydroxyacetic acid), 5-ethoxy-4-hydroxyisophthalaldehyde, 3-ethoxy-2-hydroxybenzaldehyde, (E or Z)-3-(4-hydroxy-3-methoxybenzylidene)-7-methoxybenzofuran-2(3H)-one, and (E or Z)-7-ethoxy-3-(3-ethoxy-4-hydroxybenzylidene)benzofuran-2(3H)-one, 4-hydroxy-3-methylbenzaldehyde, and 4-hydroxy-3,5-dimethylbenzaldehyde.

19. A composition according to claim 18 , wherein the vanillin and/or ethylvanillin is present in an amount of more than 50% of the total weight of the composition.

20. A composition according to claim 18 , wherein the vanillin and/or ethylvanillin is present in an amount of more than 90% of the total weight of the composition.

21. A composition according to claim 18 , wherein at least compound is present in an amount of from 1 ppm to 5000 ppm of the total weight of the composition.

22. A composition according to claim 18 , wherein at least compound is present in an amount of from 1 ppm to 100 ppm based on the total weight of vanillin and/or ethylvanillin.

23. A composition according to claim 18 , wherein said composition comprises vanillin and ethylvanillin and the vanillin/ethylvanillin molar ratio is equal to 2.

24. A product composition, comprising a vanillin and/or ethylvanillin composition according to claim 1 , wherein the product composition is selected from the group consisting of food products, beverages, cosmetic formulations, pharmaceutical formulations, and fragrances.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2024
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 066374/0642 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2023
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 065488/0365 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 21, 2021
From: VERDIER, STEPHAN; MADELAINE, FRÉDÉRIC
To: RHODIA OPERATIONS
Reel/Frame 054978/0569 →