IP Library Granted Patent US 11,566,010
Granted Patent B2
US 11,566,010 · App. 17/237,132 · Granted Jan 31, 2023

Single step process for production of 2-methyltetrahydrofuran from furfuryl alcohol

Inventors: Arrey B. Enyong (Lakeland, TN); Shridhar G. Hegde (Germantown, TN)
Assignee: Penn A. Kem, LLC
C07D307/08B01D39/2003B01J21/04B01J21/18B01J23/44B01J38/00C07C29/17
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,566,010
App. No.
17/237,132
Granted
Jan 31, 2023
Kind
B2
Abstract

Provided is a single step process for producing 2-methyltetrahydrofuran from furfuryl alcohol with high conversion rate and high selectivity towards 2-methyltetrahydrofuran.

Claims (19)

1. A process for producing 2-methyltetrahydrofuran from furfuryl alcohol, comprising the following step:

a) contacting furfuryl alcohol with hydrogen in presence of a catalytic system in a liquid solvent to obtain a reaction mixture comprising 2-methyltetrahydrofuran and the catalytic system,

wherein the catalytic system comprises a supported metal catalyst and a Lewis acid,

wherein the Lewis acid is chosen from aluminium triflate, boron trifluoride, bis(oxalato)boric acid, cyanuric chloride, iron trichloride, iron trichloride hexahydrate, iron(II) dodecyl sulfate, iron(III) dodecyl sulfate, lithium tetrafluoroborate, magnesium bromide, magnesium triflate, scandium triflate, silver triflate, tin tetrachloride, tin tetrachloride pentahydrate, zinc tetrafluoroborate, zinc triflate and mixtures thereof.

2. The process according to the claim 1 , wherein the amount of Lewis acid is 0.001 mole to 0.20 mole equivalents with respect to furfuryl alcohol.

3. The process according to the claim 1 , wherein the supported metal catalyst comprises a metal chosen from chromium, manganese, iron, cobalt, nickel, copper, zinc, molybdenum, ruthenium, rhodium, palladium, tin, platinum and mixtures thereof.

4. The process according to claim 3 , wherein the supported metal catalyst comprises a support chosen from alumina (Al 2 O 3 ), carbon, hydrotalcite, silica (SiO 2 ), titania (TiO 2 ) and mixtures thereof.

5. The process according to the claim 3 , wherein the content of metal in the supported metal catalyst relative to the support is 0.1 wt % to 10 wt %.

6. The process according to the claim 1 , wherein the amount of supported metal catalyst is 1 wt % to 25 wt % with respect to furfuryl alcohol.

7. The process according to the claim 1 , wherein the liquid solvent is chosen from acetonitrile, dichloroethane, dimethylformamide (DMF), ethanol, ethyl acetate, isopropanol, methanol, methyl tert-butyl ether (MTBE), 2-methyltetrahydrofuran, tetrahydrofuran (THF) and mixtures thereof.

8. The process according to the claim 1 , wherein the weight ratio liquid solvent:furfuryl alcohol is 1:10 to 10:1.

9. The process according to the claim 1 , wherein, during step a), the pressure is 0.5 bar to 10 bar.

10. The process according to the claim 1 , wherein, during step a), the temperature is 0° C. to 100° C.

11. The process according to the claim 1 , wherein step a) is carried out in batch mode, in semi-batch mode or continuously.

12. The process according to the claim 1 , further comprising the following steps:

b) separating the catalytic system from the reaction mixture to recover on the one hand the catalytic system and on the other hand a mixture comprising MeTHF, and

c) recycling all or part of the catalytic system recovered at the end of step b) into step a).

13. The process according to the claim 1 , wherein the supported metal catalyst comprises a support chosen from alumina, silica, titania, and mixtures thereof.

14. The process according to the claim 13 , wherein the support is alumina.

Assignments (2)
CHANGE OF NAME Recorded Nov 13, 2025
From: PENN A KEM LLC
To: MINASOLVE LLC
Reel/Frame 073543/0241 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 10, 2022
From: ENYONG, ARREY B.; HEGDE, SHRIDHAR G.
To: PENN A KEM, LLC
Reel/Frame 060771/0624 →
Continuity (1)
Related Publication 20220340536A1 · Oct 27, 2022