Production of furfural from xylose

Patent metadata

Field	Value
Publication number	US-2016304481-A1
Application number	US-201415103336-A
Country	US
Kind code	A1
Filing date	Dec 10, 2014
Priority date	Dec 13, 2013
Publication date	Oct 20, 2016
Grant date	—

Abstract

Described is a method for producing furfural from one or more substances selected from the group consisting of xylose, oligosaccharides comprising xylose units and polysaccha-rides comprising xylose units.

First claim

1 . Method for producing furfural comprising
providing an aqueous feed mixture comprising: (i) one or more substances selected from the group consisting of xylose, oligosaccharides comprising xylose units, and polysaccharides comprising xylose units (ii) methanesulfonic acid (iii) one or more salts wherein the total concentration of (iii) said one or more salts is in the range of from 0.5 wt.-% to 20 wt.-% based on the total weight of said aqueous feed mixture, contacting said aqueous feed mixture with an extraction liquid comprising one or more organic solvents, wherein said one or more solvents
have a higher solubility for furfural than said aqueous feed mixture and
are selected so that when said aqueous feed mixture is contacted with said extraction liquid two separate liquid phases are formed, wherein in a first liquid phase the concentration of water is higher than the concentration of said organic solvents and in a second liquid phase the concentration of said organic solvents is higher than the concentration of water
subjecting said aqueous feed mixture while contacted with said extraction liquid to a thermal treatment so that said one or more substances selected from the group consisting of xylose, oligosaccharides comprising xylose units, and polysaccharides comprising xylose units are reacted to furfural which is extracted from said aqueous feed mixture into said extraction liquid.

2 . Method according to claim 1 , wherein
the step of thermal treatment is conducted in a manner so that 80% by weight or more of said one or more salts (iii) provided in the aqueous feed mixture can be recovered.

3 . Method according to claim 1 , wherein
(iii) said one or more salts are selected from the group consisting of salts comprising a cation selected from the group consisting of cations of metals of groups I and IL and an anion selected from the group consisting of chloride, bromide, iodide, methanesulfonate, toluensulfonate, phosphate, tetrafluoroborate, trifluormethansulfonate, acetate and nitrate.

4 . Method according to claim 1 , wherein
the aqueous feed mixture comprises two or more salts (iii).

5 . Method according to claim 1 , wherein in said aqueous feed mixture
the total concentration of (i) said one or more substances selected from the group consisting of xylose, oligosaccharides comprising xylose units, and polysaccharides comprising xylose units is in the range of from 1 wt.-% to 70 wt. %, and/or the concentration of (ii) methanesulfonic acid is in the range of from 0.1 wt.-% to 5 wt.-%, and/or the total concentration of (iii) said one or more salts is in the range of from 5 wt.-% to 15 wt.-%, wherein the concentration in each case is based on the total weight of said aqueous feed mixture.

6 . Method according to claim 1 ,
wherein in said aqueous feed mixture a total concentration of yeast cells is 120*10 6 cells/ml or less.

7 . Method according to claim 1 , wherein
said one or more organic solvents in said extraction liquid are selected from the group consisting of solvents having a boiling point which is below the boiling point of furfural wherein in each case the boiling point is the boiling point at a pressure of 1000 hPa.

8 . Method according to claim 1 , wherein in said extraction liquid said one or more solvents are selected from the group consisting of tetrahydrofurane, methyl tetrahydrofurane and dimethyl tetrahydrofurane.

9 . Method according to claim 1 , wherein in the step of contacting said aqueous feed mixture with said extraction liquid the weight ratio of said aqueous feed mixture to said extraction liquid is in the range of from 95:5 to 5:95.

10 . Method according to claim 1 , wherein the thermal treatment of the aqueous feed mixture in contact with the extraction liquid is carried out
at a temperature in the range of from 80° C. to 250° C., at a pressure in the range of from 100 kPa to 3000 kPa, for a duration of from 1 seconds to 6 hours, wherein the pressure and the temperature are selected so that said coexisting first and second liquid phases are maintained.

11 . Method according to claim 1 , further comprising
processing cellulose-containing biomass so that said one or more substances selected from the group consisting of xylose, oligosaccharides comprising xylose units, and polysaccharides comprising xylose units are formed, and preparing said aqueous feed mixture comprising: (i) said formed one or more substances selected from the group consisting of xylose, oligosaccharides comprising xylose units, and polysaccharides comprising xylose units, (ii) methanesulfonic acid, and (iii) one or more salts wherein the total concentration of (iii) said one or more salts is in the range of from 0.5 wt.-% to 20 wt.-% based on the total weight of said aqueous feed mixture.

12 . Method according to claim 11 , wherein in said step of processing cellulose-containing biomass, a treatment mixture comprising cellulose-containing biomass, water, and methanesulfonic acid is subjected to a temperature in the range of from 100° C. to 210° C., at a pressure in the range of from 100 to 3000 kPa, wherein the pressure is selected so that at least a part of the water is in the liquid state.

13 . Method according to claim 1 , further comprising after completion of the thermal treatment one or both of the steps of
recovering from the first liquid phase an aqueous mixture comprising methane sulfonic acid (ii) and said one or more salts (iii), and using said recovered aqueous mixture for replenishing said aqueous feed mixture and/or recovering from said second liquid phase said one or more organic solvents and using said recovered one or more organic solvents for replenishing said extraction liquid.

14 . Method according to claim 1 , wherein
the aqueous feed mixture comprises (i) said one or more substances selected from the group consisting of xylose, oligosaccharides comprising xylose units, and polysaccharides comprising xylose units in a total concentration of from 1 to 70 wt.-%, (ii) methanesulfonic acid in a concentration of from 0.1 to 5 wt.-%, (iii) both salts selected from the group consisting of sodium chloride and sodium methanesulfonate, wherein the total concentration of sodium chloride and sodium methanesulfonate is in a range of from 0.5 to 20 wt. %, and the weight ratio of sodium chloride to sodium methanesulfonate is in the range of from 10:1 to 1:10, wherein the concentration in each case is based on the total weight of the aqueous feed mixture; the extraction liquid comprises methyl tetrahydrofurane and optionally one or more further constituents; in the step of contacting said aqueous feed mixture and said extraction liquid the weight ratio of said aqueous feed mixture to said extraction liquid is in the range of from 95:5 to 5:95, the thermal treatment the aqueous feed mixture in contact with the extraction liquid is carried out at a temperature in the range of from 130° C. to 220° C., for a duration of from 1 to 10 minutes at a pressure in the range of from 1200 kPa to 2000 kPa, wherein the pressure and the temperature are selected so that said coexisting first and second liquid phases are maintained.

15 . (canceled)

16 . Method according to claim 4 , wherein said two or more salts comprises
one salt selected from the group consisting of alkali metal chlorides and one salt selected from the group of alkali metal salts of methanesulfonic acid.

17 . Method according to claim 5 , wherein in said aqueous feed mixture
the total concentration of (i) said one or more subs

Assignees

• Basf Se

Inventors

• Koch Stefan
• Kindler Alois

Classifications

• C07D307/50 Primary

  Preparation from natural products · CPC title