IP Library Granted Patent US 11,318,423
Granted Patent B2
US 11,318,423 · App. 16/846,960 · Granted May 3, 2022

Processes for separation of aromatic compounds using a thin film composite membrane

Inventors: Sudipto Majumdar (Newark, DE); Ning Shangguan (Cherry Hill, NJ); Robert Daniel Lousenberg (Wilmington, DE); Kenneth Evan Loprete (Philadelphia, PA)
Assignee: Compact Membrane Systems Inc.
B01D69/125B01D53/228B01D69/02B01D71/36B01D71/82B01D67/0093B01D69/10B01D2257/702B01D2323/08B01D2323/30B01D2325/04B01D2325/20
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Quick Facts
Patent No.
US 11,318,423
App. No.
16/846,960
Granted
May 3, 2022
Kind
B2
Abstract

This invention discloses a method for separation of an aromatic compound from a mixture comprising an alkane using an improved thin-film composite membrane. The membrane is particularly useful for separation of benzene from cyclohexane, which have similar boiling points. The membrane comprises a more mechanically durable and defect-free separation layer as a result of its fabrication from an ionomer solution that is substantially free of dissolved ionic species not associated with the ionomer.

Claims (18)

1. A method of separating an aromatic compound from a mixture comprising an alkane using a thin-film composite membrane; the method comprising:

a) providing a thin-film composite membrane having a feed side and a permeate side; the thin-film composite membrane comprising:

i) a substrate comprising a porous-layer support; and

ii) a separation layer comprising an ionomer comprising sulfonate groups, selected from: silver sulfonate, sulfonic acid, or non-silver sulfonate; said separation layer is predominantly laminar, in direct contact to said substrate, and substantially free of ionic species not associated with the ionomer;

b) exposing the thin-film composite membrane to water or water vapor; and

c) exposing the feed side to a flowing first mixture comprising an aromatic compound and an alkane; and

d) providing a driving force and producing a flowing second mixture at the permeate side having a higher concentration of aromatic compound to alkane than the flowing first mixture at the feed side.

2. The method of claim 1 wherein the aromatic compound is selected from a group consisting of: benzene, toluene, or xylene.

3. The method of claim 1 wherein the flowing first mixture comprises an alkane selected from a group consisting of: ethane, propane, pentane, or cyclohexane.

4. The method of claim 1 wherein the cation of the non-silver sulfonate group is selected from: Li + , Na + , K + , ammonium, alkyl ammonium, or mixtures therefrom.

5. The method of claim 1 wherein the ionomer is comprised of repeat units A and B in which A is a polymerized derivative of a fluorinated monomer and B comprises silver sulfonate groups.

6. The method of claim 5 wherein repeat unit A is selected from a group consisting of: tetrafluoroethylene, chlorotrifluoroethylene, trifluoroethylene, vinyl fluoride, or vinylidene fluoride.

7. The method of claim 5 wherein a precursor to the repeat unit B is a monomer of structure CF 2 ═CFOR f SO 2 F wherein R f is a perfluoroalkylene group of 1 to 10 carbon atoms.

8. The method of claim 7 , wherein the perfluoroalkylene group comprises ether oxygens.

9. The method of claim 1 wherein a precursor to the ionomer in the separation layer is a copolymer comprising tetrafluoroethylene and CF 2 ═CFOCF 2 CF 2 SO 2 F.

10. The method of claim 1 wherein a precursor to the ionomer in the separation layer is a copolymer comprising tetrafluoroethylene and CF 2 ═CFOCF 2 CF(CF 3 )OCF 2 CF 2 SO 2 F.

11. The method of claim 1 wherein the ionomer has an equivalent weight that is less than 800-grams/mole.

12. The method of claim 1 wherein the separation layer has a thickness that is less than 2-μm and is predominantly laminar wherein at least 50% of the gas-separation layer extends on top of the substrate comprising a porous-layer support and is not interpenetrating into the substrate comprising a porous-layer support.

Assignments (2)
CONFIRMATORY LICENSE Recorded Nov 4, 2020
From: COMPACT MEMBRANE SYSTEMS, INC.
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 054302/0360 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 24, 2020
From: MAJUMDAR, SUDIPTO; SHANGGUAN, NING; LOUSENBERG, ROBERT DANIEL; LOPRETE, KENNETH EVAN
To: COMPACT MEMBRANE SYSTEMS, INC.
Reel/Frame 052488/0699 →
Continuity (3)
Continuation In Part 16381333 · Apr 11, 2019
Provisional Application 62789276 · Jan 7, 2019
Related Publication 20200238224A1 · Jul 30, 2020