Polymers and membranes for separation of polar organic compounds from aqueous mixtures and methods of using

Patent metadata

Field	Value
Publication number	US-2016264692-A1
Application number	US-201615066697-A
Country	US
Kind code	A1
Filing date	Mar 10, 2016
Priority date	Mar 10, 2015
Publication date	Sep 15, 2016
Grant date	—

Abstract

A polymer having a contact angle with water that is greater than or equal to 90° and a contact angle with 1,3-propane diol that is less than 90°. A pervaporation membrane comprising the polymer and a process for purifying a fermentation broth using a pervaporation membrane comprising the polymer is also described.

First claim

1 . A polymer having a contact angle with water that is greater than or equal to 90° and a contact angle with 1,3-propane diol that is less than 90°.

2 . The polymer of claim 1 , wherein the polymer comprises repeating units derived from allylcyclohexylamine or tributyl phosphate.

3 . The polymer of claim 2 , wherein the polymer comprises allylcyclohexylamine functionalized polysiloxane.

4 . The polymer of claim 2 , wherein the polymer comprises a repeating unit derived from an allylcyclohexylamine based acrylate.

5 . The polymer of claim 2 , wherein the polymer comprises a repeating unit derived from an imidazolium functionalized acrylate monomer having a dibutyl phosphate counter ion.

6 . A pervaporation membrane comprising a polymer having a contact angle with water that is greater than or equal to 90° and a contact angle with 1,3-propane diol that is less than 90°.

7 . The pervaporation membrane of claim 6 , wherein the polymer comprises repeating units derived from allylcyclohexylamine or tributyl phosphate.

8 . The pervaporation membrane of claim 7 , wherein the polymer comprises allylcyclohexylamine functionalized polysiloxane.

9 . The pervaporation membrane of claim 8 , wherein the membrane further comprises styrene-butyl acrylate copolymer.

10 . The pervaporation membrane of claim 7 , wherein the polymer comprises a repeating unit derived from an allylcyclohexylamine based acrylate

11 . The pervaporation membrane of claim 7 , wherein the polymer comprises a repeating unit derived from an imidazolium functionalized acrylate monomer having a dibutyl phosphate counter ion.

12 . The pervaporation membrane of claim 6 , wherein the membrane has a separation factor of 1,3-propane diol relative to water of greater than or equal to 5.

13 . The pervaporation membrane of claim 12 , wherein the membrane has a separation factor of 1,3-propane diol relative to glycerin greater than or equal to 1.5.

14 . The process for purifying a fermentation broth comprising:
contacting the broth with a pervaporation membrane under pervaporation conditions to produce a product comprising 1,3-propane diol wherein the pervaporation membrane comprises a polymer having a contact angle with water that is greater than or equal to 90° and a contact angle with 1,3-propane diol that is less than 90° and the fermentation broth comprises 1,3-propane diol.

15 . The process of claim 14 , further comprising removing solids from the fermentation broth prior to contact with the pervaporation membrane.

16 . The process of claim 14 , further comprising distilling the product comprising 1,3-propane diol.

17 . The process of claim 14 , wherein the pervaporation membrane has an upstream side and a downstream side and a gauge pressure on the upstream side is less than 10 atmospheres and absolute pressure on the downstream side is less than 50 millimeters of Hg.

18 . The process of claim 14 , wherein the temperature of the fermentation broth is 15 to 50° C.

19 . The process of claim 14 , wherein the pervaporation membrane has a mass uptake of pure water less than 1% and a mass uptake of pure 1,3-propane diol greater than 2.5%.

20 . The process of claim 14 , wherein the pervaporation membrane has a separation factor of 1,3-propane diol relative to water greater than or equal to 5.

21 . The process of claim 14 , wherein the polymer comprises repeating units derived from allylcyclohexylamine or tributyl phosphate.

22 . The process of claim 21 , wherein the polymer comprises allylcyclohexylamine functionalized polysiloxane.

23 . The process of claim 22 , wherein the membrane further comprises a styrene-butyl acrylate copolymer.

24 . The process of claim 21 , wherein the polymer comprises a repeating unit derived from an allylcyclohexylamine based acrylate.

25 . The process of claim 21 , wherein the polymer comprises a repeating unit derived from an imidazolium functionalized acrylate monomer having a dibutyl phosphate counter ion.

Assignees

• Univ Connecticut

Inventors

• Parnas Richard Steven
• Asandei Alexandru

Classifications

• B01D61/362

  Pervaporation · CPC title

• C08G77/388

  containing nitrogen · CPC title

• C07C29/76

  by physical treatment · CPC title

• B01D71/60

  Polyamines · CPC title

• C08F30/02 Primary

  containing phosphorus · CPC title