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US 9,468,890 B2Granted
Cycloalkylnorbornene monomers, polymers derived therefrom and their use in pervaporation
AssigneePromerus, LLC
InventorsAndrew Bell, Leah Langsdorf, Oleksandr Burtovyy
Life of this patent
Estimating the term…
Abstract
Embodiments in accordance with the present invention provide forming various polycycloalkyl polynorbornene polymers and copolymers which are useful for forming pervaporation membranes, the membranes themselves and methods of making such membranes.
Claims13
A pervaporation membrane comprising a polymer comprising a first type of repeating unit represented by formula (IA), said repeating unit is derived from a monomer of formula (I):
- wherein:
- each occurrence of X independently
- represents —CH2— or —CH2—CH2—;
- m is an integer from 0 to 5 inclusive;
- at least one of R1, R2, R3 and R4 independently represents a group of formula (A):
- wherein:
- each occurrence of Y independently
- represents —CH2— or —CH2—CH2—;
- n is 0 or 1;
- and
- R5, R6, R7 and R8 independently represents hydrogen, methyl, ethyl, linear or branched (C3-C12)alkyl, (C3-C12)cycloalkyl, (C6-C12)bicycloalkyl, (C7-C14)tricycloalkyl, (C6-C10)aryl, (C6-C10)aryl(C1-C3)alkyl, (C5-C10)heteroaryl, (C5-C10)heteroaryl(C1-C3)alkyl, hydroxy, (C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6-C12)bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10)aryloxy(C1-C3)alkyl, (C5-C10)heteroaryloxy(C1-C3)alkyl, (C6-C10)aryloxy, (C5-C10)heteroaryloxy, (C1-C6)acyloxy and halogen;
- L represents a bond;
- or
- R1 and R3 taken together with the carbon atom to which they are attached form a substituted or unsubstituted (C5-C7)cycloalkyl or (C6-C12)bicycloalkyl ring;
- remaining one or more of R1, R2, R3 and R4 independently represents hydrogen, methyl, ethyl, linear or branched (C3-C12)alkyl, (C3-C12)cycloalkyl, (C6-C12)bicycloalkyl, (C7-C14)tricycloalkyl, (C6-C10)aryl, (C6-C10)aryl(C1-C3)alkyl, (C5-C10)heteroaryl, (C5-C10)heteroaryl(C1-C3)alkyl, hydroxy, (C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6-C12)bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10)aryloxy(C1-C3)alkyl, (C5-C10)heteroaryloxy(C1-C3)alkyl, (C6-C10)aryloxy, (C5-C10)heteroaryloxy, (C1-C6)acyloxy and halogen;
- wherein each of aforementioned groups, where valence is permissible, is optionally substituted with one or more groups selected from (C1-C6)alkyl, (C3-C7)cycloalkyl, (C1-C6)perfluoroalkyl, halogen, hydroxy, acetoxy, phenyl, hydroxyphenyl, acetoxyphenyl and a group of formula (B):
- wherein:
- D is (CH2)r where r is an integer from 1 to 5 inclusive, phenylene, C6H4(CH2)s where s is an integer from 1 to 3 inclusive, or ((CH2)t—O)u where t and u independently are integers from 1 to 4 inclusive;
- E is methyl, ethyl, CF3 or C2F5;
- and
- R13 is hydrogen or (C1-C5)alkyl.
18 more elements
A method of separating butanol or phenol from a feedstock selected from a fermentation broth or a waste containing butanol or phenol comprising:
- charging the feedstock to a pervaporation module containing a pervaporation membrane formed by a polymer selected from:
- a homopolymer of 2-(bicyclo[2.2.1]hept-5-en-2-yl)bicyclo[2.2.1]heptane;
- a copolymer of 2-(bicyclo[2.2.1]hept-5-en-2-yl)bicyclo[2.2.1]heptane and hydroxyhexafluoroisopropylmethylnorbornene;
- a copolymer of 2-(bicyclo[2.2.1]hept-5-en-2-yl)bicyclo[2.2.1]heptane and norbornene;
- and
- a copolymer of 2-(bicyclo[2.2.1]hept-5-en-2-yl)bicyclo[2.2.1]heptane and 5-n-butylbicyclo[2.2.1]hept-2-ene;
- and
- collecting a permeate vapor containing butanol or phenol from the pervaporation module.
5 more elements
Dependencies are inferred from the claim text.