METHODS FOR TREATING A METATHESIS FEEDSTOCK WITH METAL ALKOXIDES

• US 20140275681A1
• Filed: 03/11/2014
• Published: 09/18/2014
• Est. Priority Date: 03/14/2013
• Status: Active Grant

• Current Assignee: Wilmar Trading Pte., Ltd. (Wilmar International Limited)
• Original Assignee: Elevance Renewable Sciences Incorporated
• Inventors: Cohen, Steven A., Anderson, Donde R., Wang, Zhe, Champagne, Timothy M., Ung, Thay A.
• Granted Patent: US 9,944,860 B2
• Time in Patent Office: Days
• US Class Current: 585/324
• CPC Class Codes: C10G 2300/1014 of vegetal origin
• CPC Class Codes: C10G 2300/1018 of animal origin
• CPC Class Codes: C10G 25/003 Specific sorbent material, not covered by C10G25/02 or C10G25/03
• CPC Class Codes: C10G 29/16 Metal oxides
• CPC Class Codes: C10G 3/45 containing iron group metals or compounds thereof
• CPC Class Codes: Y02P 30/20 using bio-feedstock

Abstract

Various methods are provided for treating and reacting a metathesis feedstock. In one embodiment, the method includes providing a feedstock comprising a natural oil, chemically treating the feedstock with a metal alkoxide under conditions sufficient to diminish catalyst poisons in the feedstock, and, following the treating, combining a metathesis catalyst with the feedstock under conditions sufficient to metathesize the feedstock.

Claims

1. A method of metathesizing a feedstock comprising:

providing a feedstock comprising a natural oil;

chemically treating the feedstock with a metal alkoxide under conditions sufficient to diminish catalyst poisons in the feedstock through a chemical reaction of the catalyst poisons; and

following chemically treating, combining a metathesis catalyst with the feedstock under conditions sufficient to metathesize the feedstock.

2. The method of claim 1, wherein the metal alkoxide comprises a metal selected from the group consisting of aluminum, titanium, zirconium, copper, iron, cerium, and silicon.

3. The method of claim 1, wherein the metal alkoxide comprises an alkoxide selected from the group consisting of methoxide, ethoxide, n-propoxide, isopropoxide, butoxide, 2-methylpropoxide, and tert-butoxide.

4. The method of claim 1, wherein the metal alkoxide is selected from the group consisting of titanium isopropoxide, aluminum ethoxide, aluminum isopropoxide, zirconium ethoxide, and mixtures thereof.

5. The method of claim 1, wherein the metal alkoxide is added at a level of between 0.01 wt. % and 1 wt. % of the feedstock.

6. The method of claim 1, wherein the chemically treating is conducted at a reactor temperature between 25°

C. and 125°

C.

7. The method of claim 1 further comprising combining an adsorbent material with the feedstock.

8. The method of claim 7, comprising combining the adsorbent material in an amount between 0.1 and 3.0 wt. %.

9. The method of claim 7, comprising combining the adsorbent material in an amount between 0.2 and 2.0 wt. %.

10. The method of claim 1, wherein the metathesis reaction comprises a maximum theoretical conversion limit, and wherein the metathesis catalyst catalyzes the metathesis of at least 50% of the maximum theoretical conversion limit at a catalyst loading of 15 ppm/db or less.

11. The method of claim 10, wherein the metathesis catalyst catalyzes the metathesis of at least 70% of the maximum theoretical conversion limit.

12. The method of claim 10, wherein the metathesis catalyst catalyzes the metathesis of at least 85% of the maximum theoretical conversion limit.

13. The method of claim 10, wherein the metathesis catalyst catalyzes the metathesis of at least 70% of the maximum theoretical conversion limit at a catalyst loading of 5 ppm/db or less.

14. The method of claim 10, wherein the metathesis catalyst catalyzes the metathesis of at least 85% of the maximum theoretical conversion limit at a catalyst loading of 5 ppm/db or less.

15. The method of claim 1, wherein the feedstock comprises a starting peroxide value of greater than 5 meq/kg and the chemically treating decreases the starting peroxide value of the feedstock to 1 meq/kg or less.

16. The method of claim 15, wherein the chemically treating decreases the starting peroxide value of the feedstock to 0.5 meq/kg or less.

17. The method of claim 1 comprising any two or more of the following:

the combining comprises a catalyst loading of 15 ppm/db or less, 5 ppm/db or less, 3 ppm/db or less, 2 ppm/db or less, or 1 ppm/db or less;

the metathesis reaction comprises a maximum theoretical conversion limit and the metathesis catalyst catalyzes the metathesis of at least 50 wt. %, at least 70%, or at least 85% of the maximum theoretical conversion limit;

the metal alkoxide is selected from the group consisting of titanium isopropoxide, aluminum ethoxide, aluminum isopropoxide, zirconium ethoxide, and mixtures thereof;

the chemically treating is conducted at a temperature between 25°

C. and 125°

C., or between 30°

C. and 100°

C.;

the feedstock comprises a starting peroxide value of greater than 5 meq/kg, or greater than 10 meq/kg;

the chemically treating decreases the peroxide value of the feedstock to a value of 1 meq/kg or less or 0.5 meq/kg or less;

combining an adsorbent material with the feedstock to diminish the catalyst poisons in the feedstock, wherein the adsorbent material is selected from the group consisting of silica gel, bleaching clay, activated carbon, charcoal, molecular sieves, zeolites, Fuller'"'"'s earth, neutral alumina, basic alumina, Celite, aluminum sulfate, calcium carbonate, Kaolin, magnesium sulfate, potassium chloride, potassium magnesium sulfate, magnesium silicate, potassium sulfate, soda ash, sodium carbonate, and sodium sulfate;

combining an adsorbent in an amount between 0.1 and 3.0 wt. % or between 0.2 and 2.0 wt. %; and

the feedstock comprises one or more materials selected from the group consisting of algal oil, canola oil, rapeseed oil, coconut oil, corn oil, cottonseed oil, olive oil, palm oil, peanut oil, safflower oil, sesame oil, soybean oil, sunflower oil, linseed oil, palm kernel oil, tung oil, jatropha oil, mustard oil, pennycress oil, camelina oil, and castor oil, natural oil derivatives thereof, and mixtures thereof.

18. A method of metathesizing a feedstock comprising:

providing a feedstock comprising a natural oil having a starting peroxide value;

chemically treating the feedstock with a metal alkoxide for a time sufficient to reduce the starting peroxide value of the feedstock by approximately 80% or more through a chemical reaction of the peroxide poisons;

following chemically treating, combining a metathesis catalyst with the feedstock under conditions sufficient to metathesize the feedstock.

19. The method of claim 18, wherein the treating decreases the starting peroxide value of the feedstock by approximately 90% or more.

20. The method of claim 18, wherein the time is between 1 hour and 24 hours.