# US 10,245,559 B2 · Nanofiltration membranes and methods of use

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- Number: US 10,245,559 B2
- Document ID: US10245559B2
- Status: Granted
- Kind: B2
- Application number: 15/176,110
- Filed: 2016-06-07
- Published: 2016-10-06
- Granted: 2019-04-02
- Earliest claimed: 2013-12-07
- Assignees: Novomer, Inc.
- Applicants: Novomer, Inc.
- Inventors: Robert E. Lapointe; Scott D. Allen; Han Lee; Thomas Widzinski; Jay J. Farmer
- Web page: https://patentgrep.com/patent/US10245559B2

## CPC

- B01D 67/0093: {Chemical modification}
- B01D 61/027: {Nanofiltration}
- B01D 71/56: Polyamides, e.g. polyester-amides
- B01D 71/60: Polyamines
- B01D 71/641: {Polyamide-imides}
- B01D 71/701: {Polydimethylsiloxane}
- B01D 71/76: Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74 (rubbers in general B01D71/24)
- B01D 71/82: characterised by the presence of specified groups, e.g. introduced by chemical after-treatment
- C07D 305/12: Beta-lactones
- B01D 2323/30: Cross-linking
- B01D 2323/36: Introduction of specific chemical groups
- B01D 2325/30: Chemical resistance
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention provides nanofiltration membranes with reduced chemical reactivity that can be utilized in manufacturing processes where reactive feedstocks and/or products are utilized or produced. Methods of making and using the membranes are also provided.

## Claims

### Claim 1

A method of removing catalyst from a process of carbonylating epoxide, comprising:
a) contacting epoxide with carbon monoxide in the presence of a homogenous carbonylation catalyst to provide a process stream comprising beta lactone and the homogenous catalyst;
b) flowing the process stream over a nanofiltration membrane to provide a permeate stream comprising beta lactone and a retentate stream comprising homogenous catalyst; and
c) returning the retentate stream to step (a),
wherein the concentration of the catalyst in the retentate stream is higher than the catalyst concentration in the permeate stream, and
wherein the nanofiltration membrane comprises a polysiloxane polymer, wherein the polysiloxane polymer is treated with a reagent reactive toward —OH groups.

### Claim 2 (depends on 1)

The method of claim 1, wherein the polysiloxane polymer comprises less than 500 nmol of free —Si(OH)— containing groups per gram of polysiloxane.

### Claim 3 (depends on 1)

The method of claim 1, wherein the polysiloxane polymer comprises polydimethylsiloxane.

### Claim 4 (depends on 1)

The method of claim 1, wherein the polysiloxane polymer is crosslinked.

### Claim 5 (depends on 1)

The method of claim 1, wherein the reagent is alkyl chloride, alkyl bromide, alkyl iodide, alkyl sulfonate ester, sulfonyl chloride, sulfonic acid anhydride, isocyanate, acid chloride, acid anhydride, alkyl chloroformate, aryl chloroformate, or R3SiX, wherein R is an aliphatic or aryl group and X is halogen.

### Claim 6 (depends on 1)

The method of claim 1, wherein the polysiloxane polymer comprises less than 500 nmol of free —Si(OH)— containing groups per gram of polysiloxane, and
wherein the reagent is an alkyl chloride, alkyl bromide, alkyl iodide, alkyl sulfonate ester, sulfonyl chloride, sulfonic acid anhydride, isocyanate, acid chloride, acid anhydride, alkyl chloroformate, aryl chloroformate or R3SiX, wherein R is an aliphatic or aryl group and X is halogen.

### Claim 7 (depends on 1)

The method of claim 1, wherein the nanofiltration membrane has reduced chemical activity toward a reactive feedstock or product comprising a carbonylation catalyst.

### Claim 8 (depends on 1)

The method of claim 1, wherein the nanofiltration membrane further comprises one or more solid materials acting as a support for the polysiloxane polymer.

### Claim 9 (depends on 8)

The method of claim 8, wherein the one or more solid materials is essentially free of —OH, —COOH, and —NH functional groups.