Nanofiltration membranes and methods of use

A method of carbonylating epoxide comprising the steps of:

• 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 said nanofiltration membrane comprises a co-polymer, the co-polymer comprising a monomer of Formula M4 and one or more of a monomer of Formula M5 and a group of Formula M6:
• wherein:
• each Ar2 is a trivalent aromatic moiety;
• each
• represents a bivalent linker and may be the same or different at each occurrence in the co-polymer;
• each
• represents a bivalent linker and may be the same or different at each occurrence in the co-polymer;
• n is any integer up to about 100,000;
• Z1 is —H, aliphatic, acyl, or aryl;
• Z2 is selected from the group consisting of:
• aliphatic, aryl, acyl, —C(O)ORx, —SO2Rx, and —C(O)NHRx;
• where Z1 and Z2 may optionally be taken together to form a ring;
• Rx is an optionally substituted aliphatic or optionally substituted aromatic group;
• and
• Ra is —H, or an optionally substituted radical selected from the group consisting of C1-20 aliphatic, C1-20 heteroaliphatic, 3- to 12-membered heterocyclic, and 6- to 12-membered aryl.

A method of carbonylating epoxide comprising the steps of:

• 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 said nanofiltration membrane comprises a co-polymer, the co-polymer comprising a monomer of Formula M4 and a monomer of Formula M13:
• wherein:
• each Ar2 is a trivalent aromatic moiety;
• each
• represents a bivalent linker and may be the same or different at each occurrence in the co-polymer;
• each
• represents a bivalent linker and may be the same or different at each occurrence in the co-polymer;
• n is any integer up to about 100,000;
• Z is a functional group that does not contain a nitrogen atom;
• and
• Ra is —H, or an optionally substituted radical selected from the group consisting of C1-20 aliphatic, C1-20 heteroaliphatic, 3- to 12-membered heterocyclic, and 6- to 12-membered aryl.

A method of carbonylating epoxide comprising the steps of:

• 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 said nanofiltration membrane comprises a co-polymer, the co-polymer comprising (i) a monomer of Formulae M7, M8 or M9, and (ii) a monomer of Formulae M10 or M11, and/or a group of Formulae M12 or M6:
• wherein:
• each Ar2 is a trivalent aromatic moiety;
• each
• represents a bivalent linker and may be the same or different at each occurrence in the co-polymer;
• each
• represents a bivalent linker and may be the same or different at each occurrence in the co-polymer;
• n is any integer up to about 100,000;
• Z1 is —H, aliphatic, acyl, or aryl;
• Z2 is selected from the group consisting of:
• aliphatic, aryl, acyl, —C(O)ORx, —SO2Rx, and —C(O)NHRx;
• Rx is an optionally substituted aliphatic or optionally substituted aromatic group;
• where Z1 and Z2 may optionally be taken together to form a ring;
• and
• Ra is —H, or an optionally substituted radical selected from the group consisting of C1-20 aliphatic, C1-20 heteroaliphatic, 3- to 12-membered heterocyclic, and 6- to 12-membered aryl.