Reductive dimerization of furfural via a continuous process

Patent metadata

Field	Value
Publication number	US-2023416214-A1
Application number	US-202318465548-A
Country	US
Kind code	A1
Filing date	Sep 12, 2023
Priority date	Sep 24, 2020
Publication date	Dec 28, 2023
Grant date	—

Abstract

Described herein are methods for the continuous preparation of 1,2-di(furan-2-yl)ethane-1,2-diol from furan-2-carbaldehyde. The methods can proceed chemically or electrochemically. In certain examples, the methods further comprise the application of a static mixer. The present methods produce 1,2-di(furan-2-yl)ethane-1,2-diol in greater yield, purity, chemoselectivity, and stereoselectivity than traditional batch methods.

First claim

1 .- 21 . (canceled)

22 . A continuous flow system for preparing 1,2-di(furan-2-yl)ethane-1,2-diol from furan-2-carbaldehyde.

23 . The continuous flow system of claim 22 , wherein said system comprises:
a first reactant stream comprising said furan-2-carbaldehyde; a second reactant stream comprising a catalyst; a solvent; and a reactor column comprising a metal.

24 . The continuous flow system of claim 23 , further comprising a coolant.

25 . The continuous flow system of claim 23 , wherein said reactor column comprising a metal comprises a static mixer, wherein said metal is deposited on surfaces of said static mixer.

26 . The continuous flow system of claim 23 , wherein said reactor column comprising a metal comprises a packed bed comprising said metal.

27 . The continuous flow system of claim 23 , further comprising a column comprising an ion exchange material.

28 .- 40 . (canceled)

41 . An electrochemical continuous flow system for reductively dimerizing furan-2-carbaldehyde to prepare 1,2-di(furan-2-yl)ethane-1,2-diol.

42 . The electrochemical continuous flow system of claim 41 , wherein said system comprises an electrolytic cell having an anode and a cathode in contact with an electrolytic medium.

43 . The electrochemical continuous flow system of claim 42 , further comprising a static mixer.

44 . The electrochemical continuous flow system of claim 43 , wherein said static mixer is said cathode.

45 .- 48 . (canceled)

49 . The continuous flow system of claim 22 , further comprising stainless steel tubing.

50 . The continuous flow system of claim 26 , wherein the packed bed comprises porous catalytic particles or beads.

51 . The continuous flow system of claim 24 , wherein the coolant comprises ethylene or propylene glycol mixtures in water.

52 . The continuous flow system of claim 24 , wherein the coolant comprises antifreeze.

53 . The continuous flow system of claim 23 , wherein said metal is selected from the group consisting of Cu, Zn, Mn, Mg, Al, Ni, Pd, Rh, Ru, Co, and Pt.

54 . The continuous flow system of claim 53 , wherein said metal is Zn.

55 . The continuous flow system of claim 23 , wherein said solvent is selected from the group consisting of tetrahydrofuran, dichloromethane, toluene, acetonitrile, diethyl ether, methanol, and NN-dimethylformamide.

56 . The continuous flow system of claim 27 , wherein said ion exchange material is polystyrene sulphonate.

57 . The continuous flow system of claim 27 , wherein said ion exchange material is crosslinked.

58 . The electrochemical continuous flow system of claim 42 , further comprising an annular tube reactor containing said electrolytic cell, wherein surfaces of said annular tube reactor are said anode.

Assignees

• Boeing Co

Inventors

• Kinlen Patrick J
• Lyons William F

Classifications

• C07D307/42 Primary

  Singly bound oxygen atoms · CPC title

• B01J8/025

  in a cylindrical shaped bed · CPC title

• B01J21/063

  Titanium; Oxides or hydroxides thereof · CPC title

• B01J47/02 Primary

  Column or bed processes · CPC title

• C25B3/05

  Heterocyclic compounds · CPC title