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Patent US3683592A successfully refreshed from Google Patents.
US3683592A
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Inhibition of polymerization on molecular sieves
Assignee: Union Carbide Corp
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Filing: 1964-02-27
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Granted: 1972-08-15
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Expires: 1984-02-27
Abstract
Abstract Molecular sieves are treated with organic compounds containing oxygen (in the form of a hydroxyl group or an ether linkage) to inhibit the ability of the molecular sieve to catalyze the polymerization of polymerizable unsaturated hydrocarbons, such as isobutylene, isoprene, butadiene, vinyl-acetylene and the like.
Inventors
- 👤 Gerard R Kamm
- 👤 Charles H Young
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 20:33
CPC Classifications
C; C10; C10G; C10G25/00; C10G25/02; C10G25/03; B; B01; B01J; B01J20/00; B01J20/02; B01J20/10; B01J20/16; B01J20/18; B01J20/186; B01J29/00; B01J29/04; B01J29/06; B01J29/70; B01J29/7003; C07; C07C; C07C7/00; C07C7/12; C07C7/13; Y; Y10; Y10S; Y10S585/00; Y10S585/949; Y10S585/952; Y10S95/00; Y10S95/90; Y10S95/902
Claims Analysis
Total Claims: 43
Claim 1
Independent Claim
32 words
The method for inhibiting the catalytic activity of a molecular sieve for the polymerization of unsaturated polymerizable organic compounds which comprises impregnating said molecular sieve with a polymerization inhibiting amount of phenol.
Claim 2
Independent Claim
32 words
The method for inhibiting the catalytic activity of a molecular sieve for the polymerization of unsaturated polymerizable organic compounds which comprises impregnating said molecular sieve with a polymerization inhibiting amount of 1-naphthol.
Claim 3
Independent Claim
192 words
The method for inhibiting the catalytic activity of a molecular sieve for the polymerization of unsaturated polymerizable organic compounds which comprises impregnating said molecular sieve with a polymerization inhibiting amount of a compound of the formula: wherein y is an integer having a value of from 0 to 1; z is a positive integer; m is an integer having a value of from 0 to 1; n is an integer having a value of from 0 to 1; R1, when taken alone, is a hydrocarbon radical having a valence of 1+y and containing from one to 20 carbons; R2, when taken alone, is a divalent hydrocarbon radical containing from one to 20 carbons; R3 is a divalent hydrocarbon radical containing from one to 20 carbons which can be the same as or different from R2; and R1 and R2, when taken together, form a radical having a valence of 3+y and consisting of hydrogen, from two to 20 carbons and no more than one oxygen, which radical forms a heterocyclic ring with oxygen having from 5 to 6 ring members in which any two oxygens are separated by at least one carbon.
Claim 4
Independent Claim
99 words
The method for inhibiting the catalytic activity of a molecular sieve for the polymerization of unsaturated polymerizable organic compounds which comprises impregnating said molecular sieve with a polymerization inhibiting amount of a heterocyclic ether of the formula wherein Z is a divalent group havinG no atoms other than carbon, hydrogen and oxygen which, when taken with the oxygen atom, forms a heterocyclic compound of from five to six ring members, said ring members being carbon atoms and from one to two oxygen atoms, said compound containing from three to 20 carbon atoms and from one to two oxygen atoms.
Claim 5
Independent Claim
32 words
The method for inhibiting the catalytic activity of a molecular sieve for the polymerization of unsaturated polymerizable organic compounds which comprises impregnating said molecular sieve with a polymerization inhibiting amount of furan.
Claim 6
Independent Claim
125 words
The method for inhibiting the catalytic activity of a molecular sieve for the polymerization of unsaturated polymerizable organic compounds which comprises impregnating said molecular sieve with a polymerization inhibiting amount of a compound of the formula: wherein a is an integer having a value of from 0 to 10; b is an integer having a value of from 2 to 3; c is an integer having a value of from 0 to 20; d is an integer having a value of from 0 to 10; with the proviso that when c is 0 each of a and d has a value of at least 1 and when c is 1 at least one of said a and d has a value of at least 1.
Claim 7
Independent Claim
33 words
The method for inhibiting the catalytic activity of a molecular sieve for the polymerization of unsaturated polymerizable organic compounds which comprises impregnating said molecular sieve with a polymerization inhibiting amount of isopropyl ether.
Claim 8
Independent Claim
37 words
The method for inhibiting the catalytic activity of a molecular sieve for the polymerization of unsaturated polymerizable organic compounds which comprises impregnating said molecular sieve with a polymerization inhibiting amount of the monoethyl ether of ethylene glycol.
Claim 9
Dependent Claim
32 words
As an article of manufacture, a molecular sieve containing a polymerization inhibiting amount of a hydrocarbon phenolic compound having from one to 20 carbon atoms and from one to two hydroxyl groups.
Claim 10
Dependent Claim
15 words
As an article of manufacture, a molecular sieve containing a polymerization inhibiting amount of phenol.
Claim 11
Dependent Claim
15 words
As an article of manufacture, a molecular sieve containing a polymerization inhibiting amount of 1-naphthol.
Claim 12
Dependent Claim
174 words
As an article of manufacture, a molecular sieve containing a polymerization inhibiting amount of a compound of the formula: wherein y is an integer having a value of from 0 to 1; z is a positive integer; m is an integer having a value of from 0 to 1; n is an integer having a value of from 0 to 1; R1, when taken alone, is a hydrocarbon radical having a valence of 1+y and containing from one to 20 carbons; R2, when taken alone, is a divalent hydrocarbon radical containing from one to 20 carbons; R3 is a divatent hydrocarbon radical containing from one to 20 carbons which can be the same as or different from R2; and Rand R2, when taken together, form a radical having a valence of 3+y and consisting of hydrogen, from two to 20 carbons and no more than one oxygen, which radical forms a heterocyclic ring with oxygen having from five to six ring members in which any two oxygens are separated by at least one carbon.
Claim 13
Dependent Claim
82 words
As an article of manufacture, a molecular sieve containing a polymerization inhibiting amount of a hetero-cyclic ether of the formula wherein Z is a divalent group having no atoms other than carbon, hydrogen and oxygen which, when taken with the oxygen atom, forms a heterocyclic compound of from five to six ring members, said ring members being carbon atoms and from one to two oxygen atoms, said compound containing from three to 20 carbon atoms and from one to two oxygen atoms.
Claim 14
Dependent Claim
15 words
As an article of manufacture, a molecular sieve containing a polymerization inhibiting amount of furan.
Claim 15
Dependent Claim
108 words
As an article of manufacture, a molecular sieve containing a polymerization inhibiting amount of a compound of the formula: wherein a is an integer having a value of from 0 to 10; b is an integer having a value of from 2 to 3; c is an integer having a value of from 0 to 20; d is an integer having a value of from 0 to 10; with the proviso that when c is 0 each of a and d has a value of at least 1 and when c is 1 at least one of said a and d has a value of at least 1.
Claim 16
Dependent Claim
16 words
As an article of manufacture, a molecular sieve containing a polymerization inhibiting amount of isopropyl ether.
Claim 17
Dependent Claim
19 words
As an article of manufacture, a molecular sieve containing a polymerization inhibiting amount of monoethyl ether of ethylene glycol.
Claim 18
Dependent Claim
56 words
In a process for the separation of organic compounds with a molecular sieve by contacting said sieve with said compounds and removing an enriched component, the improvement of employing a molecular sieve containing a polymerization inhibiting amount of a hydrocarbon phenolic compound having from 1 to 20 carbon atoms and from 1 to 2 hydroxy groups.
Claim 19
Dependent Claim
39 words
In a process for the separation of organic compounds with a molecular sieve by contacting said sieve with said compounds and removing an enriched component, the improvement of employing a molecular sieve containing a polymerization inhibiting amount of phenol.
Claim 20
Dependent Claim
39 words
In a process for the separation of organic compounds with a molecular sieve by contacting said sieve with said compounds and removing an enriched component, the improvement of employing a molecular sieve containing a polymerization inhibiting amount of 1-naphthol.
Claim 21
Dependent Claim
211 words
In a process for the separation of organic compounds with a molecular sieve by contacting said sieve with said compounds and removing an enriched component, the improvement of employing a molecular sieve containing a polymerization inhibiting amount of a compound of the formula: wherein y is an integer having a value of from 0 to 1; z is a positive integer; m is an integer having a value of from 0 to 1; n is an integer having a value of from 0 to 1; n is an integer having a value of from 0 to 1; R1, when taken alone, is a hydrocarbon radical having a valence of 1+y and containing from 1 to 20 carbons, R2, when taken alone, is a divalent hydrocarbon radical containing from 1 to 20 carbons; R3 is a divalent hydrocarbon radical containing from 1 to 20 carbons which can be the same as or different from R2; and R1 and R2, when taken together, form a radical having a valence of 3+y and consisting of hydrogen, from 2 to 20 carbons and no more than one oxygen, which radical forms a heterocyclic ring with oxygen having from 5 to 6 ring members in which any two oxygens are separated by at least one carbon.
Claim 22
Dependent Claim
106 words
In a process for the separation of organic compounds with a molecular sieve by contacting said sieve with said compounds and removing an enriched component, the improvement of employing a molecular sieve containing a polymerization inhibiting amount of a heterocyclic ether to the formula wherein Z is a divalent group having no atoms other than carbon, hydrogen and oxygen which, when taken with the oxygen atom, forms a heterocyclic compound of from 5 to 6 ring members, said ring members being carbon atoms and from 1 to 2 oxygen atoms, said compound containing from 3 to 20 carbon atoms and from 1 to 2 oxygen atoms.
Claim 23
Dependent Claim
39 words
In a process for the separation of organic compounds with a molecular sieve by contacting said sieve with said compounds and removing an enriched component, the improvement of employing a molecular sieve containing a polymerization inhibiting amount of furan.
Claim 24
Dependent Claim
132 words
In a process for the separation of organic compounds with a molecular sieve by contacting said sieve with said compounds and removing an enriched component, the improvement of employing a molecular sieve containing a polymerization inhibiting amount of a compound of the formula: wherein a is an integer having a value of from 0 to 10; b is an integer having a value of from 2 to 3; c is an integer having a value of from 0 to 20; d is an integer having a value of from 0 to 10; with the proviso that when c is 0 each of a and d has a value of at least 1 and when c is 1 at least one of said a and d has a value of at least 1.
Claim 25
Dependent Claim
40 words
In a process for the separation of organic compounds with a molecular sieve by contacting said sieve with said compounds and removing an enriched component, the improvement of employing a molecular sieve containing a polymerization inhibiting amount of isopropyl ether.
Claim 26
Dependent Claim
44 words
In a process for the separation of organic compounds with a molecular sieve by contacting said sieve with said compounds and removing an enriched component, the improvement of employing a molecular sieve containing a polymerization inhibiting amount of the monoethyl ether of ethylene glycol.
Claim 27
Independent Claim
65 words
The method for separating butadiene from vinyl acetylene which comprises contacting a mixture containing butadiene and vinyl acetylene in the vapor phase with a molecular sieve having a substantially uniform pore size of about 9 A and containing a polymerization inhibiting amount of a hydrocarbon phenolic compound having from one to 20 carbon atoms and from one to two hydroxyl groups and removing said butadiene.
Claim 28
Independent Claim
48 words
The method for separating butadiene from vinyl acetylene which comprises contacting a mixture containing butadiene and vinyl acetylene in the vapor phase with a molecular sieve having a substantially uniform pore size of about 9 Angstroms and containing a polymerization inhibiting amount of phenol and removing said butadiene.
Claim 29
Independent Claim
48 words
The method for separating butadiene from vinyl acetylene which comprises contacting a mixture containing butadiene and vinyl acetylene in the vapor phase with a molecular sieve having a substantially uniform pore size of about 9 Angstroms and containing a polymerization inhibiting amount of 1-naphthol and removing said butadiene.
Claim 30
Independent Claim
208 words
The method for separating butadiene from vinyl acetylene which comprises contacting a mixture containing butadiene and vinyl acetylene in the vapor phase with a molecular sieve having a substantially uniform pore size of about 9 A and containing a polymerization inhibiting amount of a compound of the formula: wherein y is an integer having a value of from 0 to 1; z is a positive integer; m is an integer having a value of from 0 to 1; n is an integer having a value of from 0 to 1; R1, when taken alone, is a hydrocarbon radical having a valence of 1+y and containing from one to 20 carbons; R2, when taken alone, is a divalent hydrocarbon radical containing from one to 20 carbons; R3 is a divalent hydrocarbon radical containing from one to 20 carbons which can be the same as or different from R2; and R1 and R2, when taken together, form a radical having a valence of 3+y and consisting of hydrogen, from 2 to 20 carbons and no more than one oxygen, which radical forms a heterocyclic ring with oxygen having from five to six ring members in which any two oxygens are separated by at least one carbon and removing said butadiene.
Claim 31
Independent Claim
115 words
The method for separating butadiene from vinyl acetylene which comprises contacting a mixture containing butadiene and vinyl acetylene in the vapor phase with a molecular sieve having a substantially uniform pore size of about 9 A and containing a polymerization inhibiting amount of a heterocyclic ether of the formula wherein Z is a divalent group having no atoms other than carbon, hydrogen and oxygen which, when taken with the oxygen atom, forms a heterocyclic compound of from five to six ring members, said ring members being carbon atoms and from one to two oxygen atoms, said compound containing from three to twenty carbon atoms and from one to two oxygen atoms and removing said butadiene.
Claim 32
Independent Claim
48 words
The method for separating butadiene from vinyl acetylene which comprises contacting a mixture containing butadiene and vinyl acetylene in the vapor phase with a molecular sieve having a substantiaLly uniform pore size of about 9 Angstroms and containing a polymerization inhibiting amount of furan and removing said butadiene.
Claim 33
Independent Claim
141 words
The method for separating butadiene from vinyl acetylene which comprises contacting a mixture containing butadiene and vinyl acetylene in the vapor phase with a molecular sieve having a substantially uniform pore size of about 9 A and containing a polymerization inhibiting amount of a compound of the formula: wherein a is an integer having a value of from 0 to 10; b is an integer having a value of from 2 to 3; c is an integer having a value of from 0 to 20; d is an integer having a value of from 0 to 10; with the proviso that when c is 0 each of a and d has a value of at least 1 and when c is 1 at least one of said a and d has a value of at least 1 and removing said butadiene.
Claim 34
Independent Claim
49 words
The method for separating butadiene from vinyl acetylene which comprises contacting a mixture containing butadiene and vinyl acetylene in the vapor phase with a molecular sieve having a substantially uniform pore size of about 9 A and containing a polymerization inhibiting amount of isopropyl ether and removing said butadiene.
Claim 35
Independent Claim
53 words
The method for separating butadiene from vinyl acetylene which comprises contacting a mixture containing butadiene and vinyl acetylene in the vapor phase with a molecular sieve having a substantially uniform pore size of about 9 Angstroms and containing a polymerization inhibiting amount of the monoethyl ether of ethylene glycol and removing said butadiene.
Claim 36
Independent Claim
46 words
The method for separating isobutene from n-butene which comprises contacting a mixture containing isobutene and n-butene in the vapor phase with a molecular sieve having a substantially uniform pore size of about five A and containing a polymerization inhibiting amount of phenol and removing said isobutene.
Claim 37
Independent Claim
46 words
The method for separating isobutene from n-butene which comprises contacting a mixture containing isobutene and n-butene in the vapor phase with a molecular sieve having a substantially uniform pore size of about 5 A and containing a polymerization inhibiting amount of 1-naphthol and removing said isobutene.
Claim 38
Independent Claim
206 words
The method for separating isobutene from n-butene which comprises contacting a mixture containing isobutene and n-butene in the vapor phase with a molecular sieve having a substantially uniform pore size of about 5 and and containing a polymerization inhibiting amount of a compound of the formula: wherein y is an integer having a value of from 0 to 1; z is a positive integer; m is an integer having a value of from 0 to 1; n is an integer having a value of from 0 to 1; R1, when taken alone, is a hydrocarbon radical having a valence of 1+y and containing from one to 20 carbons; R2, when taken alone, is a divalent hydrocarbon radical containing from one to 20 carbons; R3 is a divalent hydrocarbon radical containing from one to 20 carbons which can be the same as or different from R2; and R1 and R2, when taken together, form a radical having a valence of 3+y and consisting of hydrogen, from two to 20 carbons and no more than one oxygen, which radical forms a heterocyclic ring with oxygen having from five to six ring members in which any two oxygens are separated by at least one carbon and removing said isobutene.
Claim 39
Independent Claim
113 words
The method for separating isobutene from n-butene which comprises contacting a mixture containing isobutene and n-butene in the vapor phase with a molecular sieve having a substantially uniform pore size of about 5 A and containing a polymerization inhibiting amount of a heterocyclic ether of the formula wherein Z is a divalent group having no atoms other than carbon, hydrogen and oxygen which, when taken with the oxygen atom, forms a heterocyclic compound of from five to six ring members, said ring members being carbon atoms aNd from one to two oxygen atoms, said compound containing from three to 20 carbon atoms and from one to two oxygen atoms and removing said isobutene.
Claim 40
Independent Claim
46 words
The method for separating isobutene from n-butene which comprises contacting a mixture containing isobutene and n-butene in the vapor phase with a molecular sieve having a substantially uniform pore size of about 5 A and containing a polymerization inhibiting amount of furan and removing said isobutene.
Claim 41
Independent Claim
138 words
The method for separating isobutene from n-butene which comprises contacting a mixture containing isobutene and n-butene in the vapor phase with a molecular sieve having a substantially uniform pore size of about 5 A and containing a polymerization inhibiting amount of a compound of the formula: wherein a is an integer having a value of from 0 to 10; b is an integer having a value of from 2 to 3; c is an integer having a value of from 0 to 20; d is an integer having a value of from 0 to 10; with the proviso that when c is each of a and d has a value of at least 1 and when c is 1 at least one of said a and d has a value of at least 1 and removing said isobutene.
Claim 42
Independent Claim
47 words
The method for separating isobutene from n-butene which comprises contacting a mixture containing isobutene and n-butene in the vapor phase with a molecular sieve having a substantially uniform pore size of about 5 A and containing a polymerization inhibiting amount of isopropyl ether and removing said isobutene.
Claim 43
Independent Claim
51 words
The method for separating isobutene from n-butene which comprises contacting a mixture containing isobutene and n-butene in the vapor phase with a molecular sieve having a substantially uniform pore size of about 5 A and containing a polymerization inhibiting amount of the monoethyl ether of ethylene glycol and removing said isobutene.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1975-08-15 | 1976-02-14 | 1976-08-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1979-08-15 | 1980-02-14 | 1980-08-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1983-08-15 | 1984-02-14 | 1984-08-15 | $7700.00 | Window Closed / Lapsed |