Reductive dimerization of furfural via a continuous process

Patent metadata

Field	Value
Publication number	US-2022089557-A1
Application number	US-202117370697-A
Country	US
Kind code	A1
Filing date	Jul 8, 2021
Priority date	Sep 24, 2020
Publication date	Mar 24, 2022
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 . A method for continuously preparing 1,2-di(furan-2-yl)ethane-1,2-diol from furan-2-carbaldehyde

2 . The method of claim 1 , wherein said method proceeds in a continuous flow system.

3 . The method of claim 1 , comprising:
introducing a first reactant stream comprising said furan-2-carbaldehyde into a reactor column comprising a metal; introducing a second reactant stream comprising a catalyst into said reactor column; contacting said first reactant stream with said second reactant stream to form a mixture; and passing said mixture through said column to produce said 1,2-di(furan-2-ypethane-1,2-diol; wherein said method proceeds in the presence of a solvent.

4 . The method of claim 3 , wherein said reactor column comprising said metal comprises a packed bed comprising said metal.

5 . The method of claim 3 , wherein said reactor column comprising a metal comprises a static mixer wherein said metal is deposited on surfaces of said static mixer.

6 . (canceled)

7 . (canceled)

8 . (canceled)

9 . The method of claim 3 , wherein said catalyst is a transition metal salt or a rare earth metal salt.

10 . (canceled)

11 . (canceled)

12 . (canceled)

13 . (canceled)

14 . The method of claim 3 , wherein said method further comprises contacting said mixture with an ion exchange material.

15 . (canceled)

16 . (canceled)

17 . (canceled)

18 . (canceled)

19 . (canceled)

20 . (canceled)

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 . (canceled)

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 . The method of claim 1 , wherein said method proceeds by an electrochemical process.

29 . The method of claim 28 , wherein said electrochemical process comprises reductively dimerizing furan-2-carbaldehyde to prepare 1,2-di(furan-2-ypethane-1,2-diol by passing a direct electrical current through an electrolytic cell having an anode and a cathode in contact with an electrolytic medium.

30 . The method of claim 29 , wherein said electrolytic medium comprises an initial electrolysis medium comprising furan-2-carbaldehyde, water, and at least one salt.

31 . (canceled)

32 . (canceled)

33 . (canceled)

34 . The method of claim 29 , wherein said cathode is a static mixer.

35 . (canceled)

36 . The method of claim 29 , wherein an annular tube reactor contains said electrolytic cell, wherein surfaces of said annular tube reactor are said anode.

37 . (canceled)

38 . The method of claim 29 , wherein said electrolytic cell is a parallel plate reactor.

39 . An electrochemical process comprising a static mixer.

40 . The electrochemical process of claim 39 , wherein said process is for continuously preparing 1,2-di(furan-2-yl)ethane-1,2-diol from furan-2-carbaldehyde.

41 . An electrochemical continuous flow system for reductively dimerizing furan-2-carbaldehyde to prepare 1,2-di(furan-2-ypethane-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 , comprising a static mixer, wherein said static mixer is said cathode.

44 . (canceled)

45 . (canceled)

46 . (canceled)

47 . (canceled)

48 . (canceled)

Assignees

• Boeing Co

Inventors

• Kinlen Patrick J
• Lyons William F

Classifications

• C25B9/77

  having diaphragms · CPC title

• B01J19/243

  spirally, concentrically or zigzag wound · CPC title

• C25B11/046

  Alloys · CPC title

• C25B11/042

  Electrodes formed of a single material · CPC title

• C25B3/05

  Heterocyclic compounds · CPC title