Terpene-derived acids and esters and methods for preparing and using same

Patent metadata

Field	Value
Publication number	US-9682914-B2
Application number	US-201515111143-A
Country	US
Kind code	B2
Filing date	Jan 13, 2015
Priority date	Jan 13, 2014
Publication date	Jun 20, 2017
Grant date	Jun 20, 2017

Abstract

The invention relates to terpene-derived acids and esters thereof as well as to processes for synthesizing them.

First claim

What is claimed is:

1. A method of producing a compound of formula (I):

or a salt thereof, wherein R 1 is selected from the group consisting of H, unsubstituted or substituted C 1 -C 10 alkyl, and unsubstituted or substituted C 2 -C 10 alkenyl, and R 2 is selected from the group consisting of H, unsubstituted or substituted C 1 -C 10 alkyl, and COR a , in which R a is H or unsubstituted or substituted C 1 -C 10 alkyl, the method comprising:
reacting a compound having the formula IB

with ozone and subsequently with an oxidant different from ozone to obtain the compound of formula (I) wherein R 1 is H; or alternatively
reacting a compound having the formula (IB) with ozone and subsequently with a reductant to obtain a mixture comprising the compound of formula (I) wherein R 1 is H and a compound of formula (IC):

and
separating the compound of formula (I) wherein R 1 is H from the compound of formula (IC).

2. The method of claim 1 , wherein the mixture comprising the compound of formula (I) wherein R 1 is H and the compound of formula (IC) is an aqueous mixture.

3. The method of claim 2 , wherein separating the compound of formula (I) from the compound of formula (IC) is performed by:
adjusting the pH of the aqueous mixture to a first pH value that is between 6 and 10 to obtain a first organic phase that comprises the compound of formula (IC) and a first aqueous phase that comprises a salt of compound of formula (I);
separating the first aqueous phase from the first organic phase;
optionally adding an oxidant to the separated first aqueous phase;
adjusting the pH of the first aqueous solution to a second pH value that is not greater than 5 to obtain a second organic phase that comprises the compound of formula (I) wherein R 1 is H and a second aqueous phase; and
separating the second organic phase from the second aqueous phase to obtain the compound of formula (I) wherein R 1 is H.

4. The method of claim 3 , wherein the second pH value is not greater than 4.

5. The method of claim 1 , further comprising reacting the compound of formula I wherein R 1 is H, with an alcohol R b OH wherein R b is unsubstituted or substituted C 1 -C 10 alkyl or unsubstituted or substituted C 2 -C 10 alkenyl, to produce a compound of formula I wherein R 1 is unsubstituted or substituted C 1 -C 10 alkyl, or unsubstituted or substituted C 2 -C 10 alkenyl.

6. The method of claim 1 , wherein the oxidant is a peroxide.

7. The method of claim 6 , wherein the peroxide is hydrogen peroxide.

8. The method of claim 1 , wherein the reaction of the compound having the formula (IB) with ozone is carried out in the presence of a solvent.

9. The method of claim 8 , wherein the solvent comprises water, an organic solvent or a mixture there of.

10. The method of claim 1 , wherein the reaction of the compound having the formula (IB) with ozone is carried out in the absence of a solvent.

11. The method of claim 1 , further comprising performing an elimination reaction on the compound of formula (I) to obtain a compound of formula (II) or formula (III):

or a mixture thereof,
wherein R 1 is H, unsubstituted or substituted C 1 -C 10 alkyl, or unsubstituted or substituted C 2 -C 10 alkenyl.

12. The method of claim 11 , wherein the elimination reaction is performed in a solvent comprising an alcohol and an acid.

13. A method of producing a compound of formula I:

or a salt thereof, wherein R 1 is H, unsubstituted or substituted C 1 -C 10 alkyl, or unsubstituted or substituted C 2 -C 10 alkenyl, and R 2 is H, unsubstituted or substituted C 1 -C 10 alkyl, or COR a , in which R a is H or unsubstituted or substituted C 1 -C 10 alkyl, the method comprising:
providing an aqueous mixture comprising the compound of formula (I) wherein R 1 is H and a compound of formula (IC):

adjusting the pH of the aqueous mixture to a first pH value that is between 6 and 10 to obtain a first organic phase that comprises the compound of formula (IC) and a first aqueous phase that comprises a salt of compound of formula (I);
separating the first aqueous phase from the first organic phase;
optionally adding an oxidant to the separated first aqueous phase;
adjusting the pH of the first aqueous solution to a second pH value that is not greater than 5 to obtain a second organic phase that comprises the compound of formula (I) wherein R 1 is H and a second aqueous phase; and
separating the second organic phase from the second aqueous phase to obtain the compound of formula (I) wherein R 1 is H.

14. The method of claim 13 , wherein the aqueous mixture comprising the compound of formula (I) and the compound of formula (IC) is obtained by ozonolysis of a compound having the formula (IB)

Assignees

• P2 Science Inc

Inventors

• Foley Patrick
• Yang Yonghua
• Bedoukian Robert
• Killinger Thomas

Classifications

• C07C69/708

  Ethers · CPC title

• C07C67/08 Primary

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• A23V2002/00

  Food compositions, function of food ingredients or processes for food or foodstuffs · CPC title

• C07C59/125

  Saturated compounds having only one carboxyl group and containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• C07C45/40

  by oxidation with ozone; by ozonolysis · CPC title