Patent US4667045A successfully refreshed from Google Patents.
US4667045A
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Organosalts of metalate anions and process for the production of alkylene glycols therewith
Assignee: Union Carbide Corp
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Filing: 1984-03-28
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Granted: 1987-05-19
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Expires: 2004-03-28
Abstract
Abstract Novel vicinal dioxyalkylene organometalates comprising a cation having a hydrocarbyl-containing substituent are disclosed. The vicinal dioxyalkylene organometalates can be reacted with water to yield alkylene glycols.
Inventors
- 👤 John R. Briggs
- 👤 John H. Robson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 09:13
CPC Classifications
C; C07; C07F; C07F11/00; C07F11/005; C07C; C07C29/00; C07C29/09; C07C29/68; C07C31/00; C07C31/28; C07F13/00; C07F13/005; C07C2601/00; C07C2601/12; C07C2601/14
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
359 words
A vicinal dioxyalkylene organometalate compound of the formula: ##STR13## wherein x' is the integer 1; [(R 0 ) m Y n ] x'+ comprises a cation having a positive charge of x' selected from the group consisting of ammonium or phosphonium cations of the formulae: ##STR14## wherein Y is nitrogen or phosphorus, sulfonium cations of the formula: ##STR15## wherein Y is sulfur, and bis(hydrocarbyl-phosphine) iminiums of the formula: [(R.sub.3.sup.9 P).sub.2 N].sup.+ wherein R 5 to R 9 are the same or different and comprise hydrogen or hydrocarbyl substituent selected from the group consisting of aliphatic or aromatic substituents having from 1 to 20 carbon atoms with the proviso that at least one of R 5 to R 9 is a hydrocarbyl substituent and that at least one of R 5 to R 9 contains sufficient carbon atoms that said vicinal dioxyalkylene organometalate is soluble in an organic solvent; L is a cation which has a positive charge of X wherein X is 1, which is selected from the group consisting of: [(R.sup.0).sub.m Y.sub.n ].sup.x'+ as defined above, alkaline metal, quaternary ammonium and quaternary phosphonium cations; z is 1 to 4; a equals the amount of x'+(z-1)(x); and ##STR16## is an anion having a negative charge of a selected from the group consisting of anions of the formula [VO 4 C 2 H 4 ] -1 , [V 2 O 8 C 2 H 4 ] -4 , [C 2 H 4 O 2 WO 3 ] -2 , [(C 2 H 4 O 2 ) 2 WO 2 ] -2 , [V 2 O 8 C 2 H 5 ] -3 . ##STR17## wherein R 1 to R 4 are the same or different and are hydrogen, alkyl of between 1 and about 10 carbons, monocyclic or bicyclic aryl having up to about 12 carbons, alkaryl having 7 to about 10 carbons, monocyclic or bicyclic aralkyl having 7 to about 15 carbons, alkenyl having 2 to 3 carbons, cycloaklyl having 3 to about 8 carbons, and cyclic structures joining two of R 1 , R 2 , R 3 and R 4 having 3 to about 8 carbon atoms.
Claim 2
Dependent Claim
359 words
A vicinal dioxyalkylene organometalate compound of the formula: ##STR13## wherein x' is the integer 1; [(R 0 ) m Y n ] x'+ comprises a cation having a positive charge of x' selected from the group consisting of ammonium or phosphonium cations of the formulae: ##STR14## wherein Y is nitrogen or phosphorus, sulfonium cations of the formula: ##STR15## wherein Y is sulfur, and bis(hydrocarbyl-phosphine) iminiums of the formula: [(R.sub.3.sup.9 P).sub.2 N].sup.+ wherein R 5 to R 9 are the same or different and comprise hydrogen or hydrocarbyl substituent selected from the group consisting of aliphatic or aromatic substituents having from 1 to 20 carbon atoms with the proviso that at least one of R 5 to R 9 is a hydrocarbyl substituent and that at least one of R 5 to R 9 contains sufficient carbon atoms that said vicinal dioxyalkylene organometalate is soluble in an organic solvent; L is a cation which has a positive charge of X wherein X is 1, which is selected from the group consisting of: [(R.sup.0).sub.m Y.sub.n ].sup.x'+ as defined above, alkaline metal, quaternary ammonium and quaternary phosphonium cations; z is 1 to 4; a equals the amount of x'+(z-1)(x); and ##STR16## is an anion having a negative charge of a selected from the group consisting of anions of the formula [VO 4 C 2 H 4 ] -1 , [V 2 O 8 C 2 H 4 ] -4 , [C 2 H 4 O 2 WO 3 ] -2 , [(C 2 H 4 O 2 ) 2 WO 2 ] -2 , [V 2 O 8 C 2 H 5 ] -3 . ##STR17## wherein R 1 to R 4 are the same or different and are hydrogen, alkyl of between 1 and about 10 carbons, monocyclic or bicyclic aryl having up to about 12 carbons, alkaryl having 7 to about 10 carbons, monocyclic or bicyclic aralkyl having 7 to about 15 carbons, alkenyl having 2 to 3 carbons, cycloaklyl having 3 to about 8 carbons, and cyclic structures joining two of R 1 , R 2 , R 3 and R 4 having 3 to about 8 carbon atoms.
Claim 3
Dependent Claim
298 words
A vicinal dioxyalkylene organometalate compound of the formula: ##STR18## wherein x' is the integer 1; [(R o ) m Y n ] x'+ comprises a cation having a positive charge of x' selected from the group consisting of phosphonium cations of the formulae: ##STR19## wherein Y is phosphorus, sulfonium cations of the formula: ##STR20## wherein Y is sulfur, and bis(hydrocarbyl-phosphine) iminiums of the formula: [(R.sub.3.sup.9 P).sub.2 N].sup.+ wherein R 5 to R 9 are the same or different and comprise hydrogen or hydrocarbyl substituents selected from the group consisting of aliphatic or aromatic substituents having from about 1 to 20 carbon atoms with the proviso that at least one of R 5 to R 9 is a hydrocarbyl substituent and that at least one of R 5 to R 9 contains sufficient carbon atoms that said vicinal dioxyalkylene organometalate is soluble in an organic solvent; L is a cation which has a positive charge of X wherein X is 1, which is selected from the group consisting of: [(R.sup.0).sub.m Y.sub.n ].sup.x'+ as defined above, alkaline metal, quaternary ammonium and quaternary phosphonium cations; z is 1 to 4; a equals the amount of x'+(z-1)(x); and ##STR21## is an anion of negative charge a selected from the group consisting of anions of the formula [VO 4 C 2 H 4 ] -1 , [V 2 O 8 C 2 H 4 ] -4 , [C 2 H 4 O 2 WO 3 ] -2 , [(C 2 H 4 O 2 ) 2 WO 2 ] -2 , [V 2 O 8 C 2 H 5 ] -3 , ##STR22## wherein R 1 , R 2 , R 3 and R 4 are the same or different and are hydrogen or alkyl of between 1 and about 10 carbon atoms.
Claim 4
Dependent Claim
298 words
A vicinal dioxyalkylene organometalate compound of the formula: ##STR18## wherein x' is the integer 1; [(R o ) m Y n ] x'+ comprises a cation having a positive charge of x' selected from the group consisting of phosphonium cations of the formulae: ##STR19## wherein Y is phosphorus, sulfonium cations of the formula: ##STR20## wherein Y is sulfur, and bis(hydrocarbyl-phosphine) iminiums of the formula: [(R.sub.3.sup.9 P).sub.2 N].sup.+ wherein R 5 to R 9 are the same or different and comprise hydrogen or hydrocarbyl substituents selected from the group consisting of aliphatic or aromatic substituents having from about 1 to 20 carbon atoms with the proviso that at least one of R 5 to R 9 is a hydrocarbyl substituent and that at least one of R 5 to R 9 contains sufficient carbon atoms that said vicinal dioxyalkylene organometalate is soluble in an organic solvent; L is a cation which has a positive charge of X wherein X is 1, which is selected from the group consisting of: [(R.sup.0).sub.m Y.sub.n ].sup.x'+ as defined above, alkaline metal, quaternary ammonium and quaternary phosphonium cations; z is 1 to 4; a equals the amount of x'+(z-1)(x); and ##STR21## is an anion of negative charge a selected from the group consisting of anions of the formula [VO 4 C 2 H 4 ] -1 , [V 2 O 8 C 2 H 4 ] -4 , [C 2 H 4 O 2 WO 3 ] -2 , [(C 2 H 4 O 2 ) 2 WO 2 ] -2 , [V 2 O 8 C 2 H 5 ] -3 , ##STR22## wherein R 1 , R 2 , R 3 and R 4 are the same or different and are hydrogen or alkyl of between 1 and about 10 carbon atoms.
Claim 5
Dependent Claim
30 words
The compound of claim 1, wherein R 1 , R 2 , R 3 and R 4 are hydrogen or alkyl of between about 1 and about 10 carbon atoms.
Claim 6
Dependent Claim
19 words
The compound of claim 3, wherein R 1 , R 2 , R 3 and R 4 are hydrogen.
Claim 7
Dependent Claim
28 words
The compound of claim 3, wherein sufficient carbons are provided in at least one R 5 to R 9 substituent that the compound is substantially insoluble in water.
Claim 8
Dependent Claim
15 words
The compound of claim 5 in which the anion comprises at least one of ##STR23##
Claim 9
Dependent Claim
25 words
The compound of claim 3 in which the anion comprises an anion characterized by the formula [VO 4 C 2 H 4 ] -1 .
Claim 10
Dependent Claim
27 words
The compound of claim 3 in which the anion comprises an anion characterized by the formula [V 2 O 8 C 2 H 4 ] -4 .
Claim 11
Dependent Claim
40 words
The compound of claim 3 in which the anion comprises an anion characterized by the formula [C 2 H 4 O 2 WO 3 ] 2- or [(C 2 H 4 O 2 ) 2 WO 2 ] 2- .
Claim 12
Dependent Claim
27 words
The compound of claim 3 in which the anion comprises an anion characterized by the formula [V 2 O 8 C 2 H 5 ] 3- .
Claim 13
Dependent Claim
18 words
The compound of claim 3 in which at least one R 5 to R 9 has four carbons.
Claim 14
Dependent Claim
57 words
The compound of claims 6, 7, 8, 9 or 10, wherein [(R 0 ) m Y n ] x'+ is an ammonium or phosphonium cation of the formula: ##STR24## wherein Y is nitrogen or phosphorus, and R 5 to R 8 are hydrogen or an aliphatic or aromatic substituent of from about 1 to 20 carbon atoms.
Claim 15
Dependent Claim
39 words
The compound of claims 6, 7, 8, 9 or 10 wherein [(R 0 ) m Y n ] x'+ is selected from the group consisting of bis(triphenylphosphine) iminium, (tetra-n-propyl) ammonium, (tetra-n-hexyl) ammonium, tri-ethyl sulfonium, (tetra-n-heptyl) ammonium, and (tetra-n-octadecyl) ammonium.
Claim 16
Dependent Claim
42 words
The compound of claim 2, in which the cation has the formula [(R 3 9 P) 2 N] + wherein each R 9 is the same or different and is hydrogen or aliphatic or aromatic substituents of 1 to 20 carbon atoms.
Claim 17
Dependent Claim
48 words
The compound of claim 2, wherein [(R 0 ) m Y n ] x'+ is a sulfonium cation of the formula: ##STR25## wherein Y is sulfur and R 5 to R 7 are hydrogen or an aliphatic or aromatic substituent of from about 1 to 20 carbon atoms.
Claim 18
Dependent Claim
48 words
The compound of claim 2, wherein [(R 0 ) m Y n ] x'+ is a phosphonium cation of the formula: ##STR26## wherein Y is phosphorus, and R 5 to R 8 are hydrogen or an aliphatic or aromatic substituent of from about 1 to 20 carbon atoms.
Claim 19
Dependent Claim
29 words
The compound of claims 14 or 15, wherein [(R 0 ) m Y n ] x'+ is selected from the group consisting of bis(triphenyl phosphine) iminium and triethyl sulfonium.
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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) | 1990-05-18 | 1990-11-17 | 1991-05-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-05-18 | 1994-11-17 | 1995-05-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-05-18 | 1998-11-17 | 1999-05-19 | $7700.00 | Window Closed / Lapsed |