Method for producing muconic acids and furans from aldaric acids

Patent metadata

Field	Value
Publication number	US-9969669-B2
Application number	US-201515317983-A
Country	US
Kind code	B2
Filing date	Jun 15, 2015
Priority date	Jun 13, 2014
Publication date	May 15, 2018
Grant date	May 15, 2018

Abstract

The present invention relates to selective catalytic dehydroxylation method of aldaric acids for producing muconic acid and furan chemicals, which can be used directly in fine chemical and polymer applications (FCA/FDCA) and as intermediates in the preparation of industrially significant chemicals, such as terephthalic acid, adipic acid, caprolactone, caprolactam, nylon 6.6, 1,6-hexanediol and multiple pharmaceutical building blocks (MA/MAME).

First claim

The invention claimed is:

1. A method for producing muconic acid from aldaric acid, wherein the method is also capable of producing furan chemicals, the method comprising selective catalytic dehydroxylation of the aldaric acid by heating the aldaric acid with a solvent and a reductant in a pressurized container to temperatures between 90 to 300° C. in the presence of a transition metal catalyst for a pre-determined reaction time and purifying the resulting product(s), wherein the catalysis is directed towards muconic acid by using catalytic temperatures between 90 and 150° C. and towards furan chemicals by using catalytic temperatures between 150 and 300° C.

2. The method according to claim 1 , wherein the aldaric acid is galactaric acid having formula I:

3. The method according to claim 1 , wherein the catalysis is selectively directed towards muconic acid by using a catalytic temperature between 100 and 150° C.

4. The method according to claim 1 , wherein the catalysis is selectively directed towards furan chemicals by using catalytic temperatures between 150 and 250° C.

5. The method according to claim 1 for producing compounds having structural formulas II, III, VIII and IX by using temperatures between 90 and 150° C.

6. The method according to claim 1 for producing compounds having structural formulas IV-VII by using temperatures between 150 and 300° C.

7. The method according to claim 1 , wherein the transition metal catalyst is selected from rhenium, palladium, vanadium and molybdenum catalysts.

8. The method according to claim 1 , wherein the catalyst is methyl trioxo rhenium.

9. The method according to claim 1 , wherein the catalyst is used at a ratio of 1.0 to 10 mol-% per aldaric acid with mucic acid or mucic acid alkyl ester.

10. The method according to claim 1 , wherein the reductant is hydrogen.

11. The method according to claim 1 , wherein the solvent is selected from methanol, ethanol or butanol.

12. The method according to claim 1 , wherein the pressure inside the container is adjusted to a level of 1 to 20 bars with hydrogen gas.

13. The method according to claim 1 , wherein the reaction time is 1 minute to 70 hours.

14. The method according to claim 1 , wherein the reaction time is 1 to 70 hours when targeting towards MA/MAME and 1 minute to 60 minutes when targeting towards furan chemicals.

15. The method according to claim 1 , wherein the purification comprises filtering any solid precipitate, washing the precipitate with alcohol, drying the washed product(s) and subsequently evaporating the organic phase and using a chromatography for recovering the desired products.

16. The method according to claim 1 , wherein the transition metal catalyst is selected from rhenium catalysts.

17. The method according to claim 1 , wherein the catalysis is selectively directed towards muconic acid by using a catalytic temperature of 120° C.

Assignees

• Teknologian Tutkimuskeskus Vtt Oy

Inventors

• Asikainen Martta
• Thomas David
• Harlin Ali

Classifications

• B01J23/34

  Manganese · CPC title

• C07C51/377 Primary

  by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups {(C07C51/36 - C07C51/373 take precedence)} · CPC title

• B01J23/36

  Rhenium · CPC title

• C07C67/08

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

• C07D307/68

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen · CPC title