Alkoxylated bio-oil polyol compositions

Patent metadata

Field	Value
Publication number	US-10793672-B2
Application number	US-201515318036-A
Country	US
Kind code	B2
Filing date	Jun 11, 2015
Priority date	Jun 11, 2014
Publication date	Oct 6, 2020
Grant date	Oct 6, 2020

Abstract

Methods are provided for producing bio-oil polyols, alkoxylating bio-oil polyols to provide polyols, and for employing the alkoxylated bio-oil polyols for making polymers or copolymers of polyesters or polyurethanes.

First claim

The invention claimed is:

1. An alkoxylated bio-oil polyol, the alkoxylated bio-oil polyol being produced by a process comprising alkoxylation of a bio-oil polyol at a temperature between about 80 degree Celsius (° C.) and about 180° C. in the presence of a cyclic alkylene oxide, the alkoxylated bio-oil polyol being characterized compared to the bio-oil polyol by one or more of: a reduced viscosity; an increased molecular weight; a lower gel permeation chromatography retention time; a weight percentage increase over a weight of the bio-oil polyol; and a reduced hydroxyl value; wherein the bio-oil is obtained from reaction of a bio-oil with a reagent polyol and the bio-oil is obtained from the pyrolysis of wood or other lignocellulosic-containing biomass.

2. The alkoxylated bio-oil polyol of claim 1 , the alkoxylated bio-oil polyol being characterized compared to the bio-oil polyol by the reduced viscosity, the reduced viscosity being a percentage of a viscosity of the bio-oil of between about 1% and less than 100%.

3. The alkoxylated bio-oil polyol of claim 1 , the alkoxylated bio-oil polyol being characterized compared to the bio-oil polyol by the increased molecular weight, the increased molecular weight being a percentage of a molecular weight of the bio-oil of between greater than 100% and less than about 200%.

4. The alkoxylated bio-oil polyol of claim 1 , the alkoxylated bio-oil polyol being characterized compared to the bio-oil polyol by the weight percentage increase over the weight of the bio-oil polyol, the weight percentage increase over the weight of the bio-oil polyol between about 1% and about 100%.

5. The alkoxylated bio-oil polyol of claim 1 , the alkoxylated bio-oil polyol being characterized compared to the bio-oil polyol by the reduced hydroxyl value, the reduced hydroxyl value being between about 1% and less than 100% of a number of free hydroxyl groups in the bio-oil polyol.

6. A method for preparing an alkoxylated bio-oil polyol, the method comprising alkoxylation of a bio-oil polyol at a temperature between about 80 degree Celsius (° C.) and about 180° C. in the presence of a cyclic alkylene oxide, wherein the bio-oil is obtained from reaction of a bio-oil with a reagent polyol and the bio-oil is obtained from the pyrolysis of wood or other lignocellulosic-containing biomass; and further wherein the alkoxylated bio-oil polyol, compared to the bio-oil polyol, is characterized by one or more of: a reduced viscosity; an increased molecular weight a lower gel permeation chromatography retention time; a weight percentage increase over a weight of the bio-oil polyol; and a reduced hydroxyl value.

7. The method of claim 6 , the reaction conditions comprising one or more of: a presence of a catalytic alkali metal hydroxide or a catalytic alkali earth metal hydroxide or oxide; a presence of a catalytic amount of potassium hydroxide; a presence of an acidified lignin a presence of a catalyst in a weight % compared to a weight of the bio-oil polyol of between about 0.01 weight % and about 5 weight %; a temperature between about 80° C. and about 180° C.; and a pressure in pounds per square inch of between about 0 and about 600.

8. The method of claim 6 , the bio-oil being produced by catalytic pyrolysis of wood or other lignocellulosic-containing biomass.

9. The method of claim 6 , further comprising reacting a bio-oil with at least one of the bio-oil and a reagent polyol in the presence of a polyol-forming catalyst to provide the bio-oil polyol.

10. The method of claim 9 , one or more of: the reagent polyol comprising one or more of: glycerol, ethylene glycol, propylene glycol, 1,3-propanediol, 2-methyl-1,3-propanediol, pentaerythritol, a sugar alcohol, an alcohol amine, a polyalkylene glycol, acidified and demethylated crude glycerol, and wet crude glycerol from steam splitting; the polyol-forming catalyst comprising tin; further comprising contacting an acidified lignin to one or more of: the bio-oil, the reagent polyol, and the polyol-forming catalyst; further comprising pyrolyzing biomass to provide the bio-oil or catalytically pyrolyzing biomass to provide the bio-oil as a catalytic bio-oil.

11. The alkoxylated bio-oil polyol of claim 1 , wherein the reagent polyol comprises one or more of: glycerol, ethylene glycol, propylene glycol, 1,3-propanediol, 2-methyl-1,3-propanediol, pentaerythritol, a sugar alcohol, an alcohol amine, a polyalkylene glycol, acidified and demethylated crude glycerol, or wet crude glycerol from steam splitting.

12. The alkoxylated bio-oil polyol of claim 1 , wherein the reagent polyol comprises glycerol.

13. The alkoxylated bio-oil polyol of claim 1 , wherein the bio-oil is reacted with the reagent polyol in the presence of a polyol-forming catalyst.

14. The alkoxylated bio-oil polyol of claim 13 , wherein the polyol-forming catalyst is tin (II) oxalate.

15. The alkoxylated bio-oil polyol of claim 1 , wherein the bio-oil is obtained from the catalytic pyrolysis of wood or other lignocellulosic-containing biomass.

16. The alkoxylated bio-oil polyol of claim 1 , wherein the bio-oil is obtained from the pyrolysis of wood.

17. The alkoxylated bio-oil polyol of claim 1 , wherein the bio-oil is a bio-oil high in lignin content.

Assignees

• Battelle Memorial Institute

Inventors

• Garbark Daniel
• Benecke Herman
• Moore Megan
• Perry Mark J
• Cafmeyer Jeffrey T

Classifications

• C08G18/4891

  modified with higher fatty oils or their acids or by resin acids · CPC title

• C08G18/4288

  modified by higher fatty oils or their acids or by resin acids · CPC title

• C08G18/4261

  prepared by oxyalkylation of polyesterpolyols · CPC title

• C08G18/4244

  containing oxygen in the form of ether groups · CPC title

• C08G18/4233

  derived from polymerised higher fatty acids or alcohols · CPC title