Method of extracting 5-chloromethylfurfural with an organic solvent from cellulosic fibers and man-made non-cellulosic fibers hydrolysed together with hydrochloric acid

Patent metadata

Field	Value
Publication number	US-2025146212-A1
Application number	US-202318835930-A
Country	US
Kind code	A1
Filing date	Mar 2, 2023
Priority date	Mar 4, 2022
Publication date	May 8, 2025
Grant date	—

Abstract

A process for obtaining chemical building blocks from fabric material containing cellulose fibres such as cotton, as well as polyester fibre material, polyethylene or polypropylene fibre material, polyamide fibre material, or elastane fibre material. Said process comprises hydrolysing cellulose by a process that does not affect polyester, the polyolefins, polyamide fibre material, or elastane fibre material, and converting the hydrolysed cellulose into a useful chemical building block.

First claim

1 . A process for treating mixed fabric material, said mixed fabric material comprising cellulosic fibre material in an amount of 30-99% by weight and comprising 1-70% by weight of one or more of man-made polyester fibre material, polyethylene fibre material, polypropylene fibre material, polyamide fibre material, or elastane fibre material, said process comprising:
a. providing in a reactor:
said mixed fabric material, comprising cellulosic fibre material in an amount of 30-99% by weight and comprising 1-70% by weight of one or more of man-made polyester fibre material, polyethylene fibre material, polypropylene fibre material, polyamide fibre material or elastane fibre material,
an aqueous solution of hydrochloric acid, the aqueous solution having a concentration of hydrochloric acid of 30%-45% by weight,
an organic extraction solvent, and wherein the organic extraction solvent is chosen such that at 20° C. less than 1 g of extraction solvent dissolves in 100 ml of the aqueous HCl solution, and wherein the organic extraction solvent is further chosen such that at 20° C. at least 10 g of 5-(chloromethyl)furfural can be dissolved in 100 ml of the organic extraction solvent,
b. mixing the contents of the reactor at a temperature of between 40° C. and 110° C. for at least 30 minutes and wherein the aqueous solution and the organic extraction solvent are present in the reactor in a ratio aqueous solution:organic extraction solvent of between 1:0.5 and 1:10, c. separating the organic extraction solvent containing 5-(chloromethyl)furfural from the aqueous solution comprising hydrochloric acid.

2 . A process for treating mixed fabric material, said mixed fabric material comprising cellulosic fibre material in an amount of 30-99% by weight and comprising 1-70% by weight of one or more of man-made polyester fibre material, polyethylene fibre material, polypropylene fibre material, polyamide fibre material, or elastane fibre material, said process comprising:
a. providing in a reactor:
said mixed fabric material, comprising cellulosic fibre material in an amount of 30-99% by weight and comprising 1-70% by weight of one or more of man-made polyester fibre material, polyethylene fibre material, polypropylene fibre material, polyamide fibre material, or elastane fibre material,
an aqueous solution of hydrochloric acid, the aqueous solution having a concentration of hydrochloric acid of 36%-51% by weight,
for a time of at least 30 minutes and at a temperature of below 40° C. to at least partly hydrolyse the cellulose in the cellulose fibre material, to yield an aqueous hydrolysate and solid fibrous residue,
b. removing from the product of a. the solid fibrous residue, c. mixing the aqueous hydrolysate obtained by b. with an organic extraction solvent at a temperature of between 50° C. and 110° C. for at least 30 minutes and wherein the aqueous solution and the organic extraction solvent are present in the reactor in a ratio aqueous solution:organic extraction solvent of between 1:0.5 and 1:10, and wherein the organic extraction solvent is chosen such that at 20° C. less than 1 g of extraction solvent dissolves in 100 ml of the aqueous HCl solution and wherein the organic extraction solvent is further chosen such that at 20° C. at least 10 g of 5-(chloromethyl)furfural can be dissolved in 100 ml of the organic extraction solvent, d. separating the organic extraction solvent containing 5-(chloromethyl)furfural from the aqueous solution comprising hydrochloric acid.

3 . The process according to claim 1 , wherein after stage b. any solid matter, including solid fibre material residue, is removed from the liquid phase.

4 . The process according to claim 1 or 3 , wherein in stage b. the mixing of the contents of the reactor is conducted for a time of between 0.5 hours and 12 hours.

5 . The process according to claim 2 , wherein in stage c. the mixing of the contents of the reactor is conducted for a time of between 0.5 hours and 12 hours.

6 . The process according to claim 2 , wherein the non-liquid matter that is removed comprises one or more of polyester fibre material, polyethylene fibre material, polypropylene fibre material, polyamide fibre material, or elastane fibre material.

7 . The process according to claim 1 , wherein the organic extraction solvent comprises diisopropyl ether, ethyl acetate, pentane, hexane, heptane, octane, decane, dodecane, cyclohexane, benzene, toluene, xylene, 1,2-dichloroethane, carbon tetrachloride, trichloromethane, halogenated aromatic solvents, and mixtures thereof.

8 . The process according to claim 7 , wherein the organic extraction solvent comprises toluene, halogenated aromatic solvents, 1,2-dichloroethane, or mixtures thereof.

9 . The process according to claim 8 , wherein the halogenated aromatic solvent comprises chlorobenzene, o-dichlorobenzene, m-dichlorobenzene, p-dichlorobenzene, 1,2,3-trichlorobenzene, 1,2,4-trichlorobenzene, 1,3,5-trichlorobenzene, fluorobenzene, o-difluorobenzene, m-difluorobenzene, p-difluorobenzene, 1,2,3-trifluorobenzene, 1,2,4-trifluorobenzene, 1,3,5-trifluorobenzene, mixed halobenzene compounds, and mixtures thereof.

10 . The process according to claim 1 , wherein the cellulosic fibre comprises cotton.

11 . The process according to claim 1 , wherein the amount of mixed fabric material:aqueous solution of hydrochloric acid in a. is between 1:200 and 1:5.

12 . The process according to claim 1 , wherein the mixed fabric material comprises cellulosic fibre material in an amount of 40-98% by weight.

13 . The process according to claim 1 , wherein the mixed fabric material comprises 2-40% by weight of one or more of man-made polyester fibre material, polyethylene fibre material, polypropylene fibre material.

14 . The process according to claim 1 , wherein the 5-(chloromethyl)furfural obtained in solution in the last stage claimed is isolated from the organic extraction solvent.

15 . The process according to claim 1 , wherein the mixed fabric material comprises woven material, non-woven material, braided material or mixtures thereof.

Assignees

• Avantium Knowledge Centre Bv

Inventors

• Bueno Moron Jorge
• Gruter Gerardus Johannes Maria
• Van Klink Gerardus Petrus Maria

Classifications

• D06M2101/32

  Polyesters · CPC title

• D06M2101/06

  cellulosic · CPC title

• C08J11/24

  containing hydroxyl groups · CPC title

• C08J11/14 Primary

  by treatment with steam or water · CPC title

• C07D307/48

  Furfural · CPC title