IP Library Granted Patent US 10,053,441
Granted Patent B2
US 10,053,441 · App. 15/418,385 · Granted Aug 21, 2018

Methods for purifying 5-(halomethyl)furfural

Inventors: Alex B. Wood (Sacramento, CA); Shawn M. Browning (Sacramento, CA); Makoto N. Masuno (Elk Grove, CA); Ryan L. Smith (Sacramento, CA); John Bissell, II (Sacramento, CA)
Assignee: MICROMIDAS, INC.
C07D307/48
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Quick Facts
Patent No.
US 10,053,441
App. No.
15/418,385
Granted
Aug 21, 2018
Kind
B2
Abstract

The present disclosure provides methods for purifying a 5-(halomethyl)furfural composition, including 5-(chloromethyl)furfural, at operating conditions that decrease or minimize the decomposition or degradation of 5-(chloromethyl)furfural during the process. The methods may employ certain solvents, operating conditions, and/or techniques (e.g., gas stripping). The gaseous 5-(halomethyl)furfural produced from the process can be condensed or deposited to yield 5-(halomethyl)furfural in liquid or solid form. The solid 5-(halomethyl)furfural may be amorphous or crystalline.

Claims (17)

1. A method for purifying 5-(halomethyl)furfural, comprising:

a) providing a 5-(halomethyl)furfural composition to a purification apparatus, wherein the 5-(halomethyl)furfural composition comprises 5-(halomethyl)furfural and one or more impurities, and wherein the 5-(halomethyl)furfural composition has a mass ratio of the one or more impurities to the 5-(halomethyl)furfural;

b) providing a stripping agent to the purification apparatus, wherein the stripping agent has a vapor pressure above the vapor pressure of 5-(halomethyl)furfural; and

c) vaporizing the 5-(halomethyl)furfural in the 5-(halomethyl)furfural composition by contacting the stripping agent with the 5-(halomethyl)furfural composition to form gaseous 5-(halomethyl)furfural, wherein the gaseous 5-(halomethyl)furfural has a mass ratio of the one or more impurities to the 5-(halomethyl)furfural that is lower than the mass ratio for the 5-(halomethyl)furfural composition.

2. The method of claim 1 , further comprising condensing the gaseous 5-(halomethyl)furfural to obtain purified 5-(halomethyl)furfural in liquid form.

3. The method of claim 1 , further comprising depositing the gaseous 5-(halomethyl)furfural to obtain 5-(halomethyl)furfural in solid form.

4. The method of claim 1 , further comprising boiling the 5-(halomethyl)furfural composition in the purification apparatus to obtain a second gaseous 5-(halomethyl)furfural, wherein the second gaseous 5-(halomethyl)furfural has a mass ratio of the one or more impurities to the 5-(halomethyl)furfural that is lower than the mass ratio for the 5-(halomethyl)furfural composition.

5. The method of claim 1 , wherein the 5-(halomethyl)furfural is 5-(chloromethyl)furfural.

6. A method for purifying 5-(halomethyl)furfural, comprising:

a) providing a 5-(halomethyl)furfural composition to a purification apparatus, wherein the 5-(halomethyl)furfural composition comprises 5-(halomethyl)furfural and one or more impurities, and wherein the purification apparatus has an operating temperature of at least 140° C. and an operating pressure of at least 30 torr; and

b) boiling the 5-(halomethyl)furfural composition to obtain gaseous 5-(halomethyl)furfural, wherein the gaseous 5-(halomethyl)furfural has a mass ratio of the one or more impurities to the 5-(halomethyl)furfural that is lower than the mass ratio for the 5-(halomethyl)furfural composition.

7. The method of claim 6 , wherein the operating pressure is between 30 torr and 2000 torr.

8. The method of claim 6 , wherein the 5-(halomethyl)furfural provided to the purification apparatus has less than 30 wt % of the one or more impurities.

9. The method of claim 6 , wherein the 5-(halomethyl)furfural provided to the purification apparatus has less than 5 wt % of residual hydrochloric acid.

10. The method of claim 6 , further comprising condensing the gaseous 5-(halomethyl)furfural to obtain purified 5-(halomethyl)furfural in liquid form.

11. The method of claim 6 , further comprising depositing the gaseous 5-(halomethyl)furfural to obtain purified 5-(halomethyl)furfural in solid form.

12. The method of claim 6 , wherein the 5-(halomethyl)furfural is 5-(chloromethyl)furfural.

Assignments (3)
CHANGE OF NAME Recorded Feb 14, 2022
From: MICROMIDAS, INC.
To: ORIGIN MATERIALS OPERATING, INC.
Reel/Frame 059109/0403 →
SECURITY INTEREST Recorded Nov 12, 2019
From: MICROMIDAS, INC,
To: PM OPERATING, LTD.
Reel/Frame 050980/0661 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 30, 2017
From: WOOD, ALEX B.; BROWNING, SHAWN M.; MASUNO, MAKOTO N.; SMITH, RYAN L.; BISSELL, JOHN, II
To: MICROMIDAS, INC.
Reel/Frame 043984/0574 →
Continuity (4)
Division 14852306 · Sep 11, 2015
Continuation PCTUS2014024949 · Mar 12, 2014
Provisional Application 61785760 · Mar 14, 2013
Related Publication 20170137397A1 · May 18, 2017
Cited By (1)
US 12,281,089