US5136097A
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US
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Process for the preparation of sulfonylmethanes and derivatives thereof
Assignee: Hydro-Québec
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Filing: 1990-04-05
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Granted: 1992-08-04
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Expires: 2010-04-05
Abstract
Abstract The invention relates to a process for the synthesis of sulfonylmethanes and derivatives thereof of the formula M[(RSO 2 ) 2 CH] m (I), in which M represents H, an alkali metal or alkaline earth metal or NR' 4 , R' and R are monovalent organic radicals and m represents the valence of M. The process comprises reacting an ionic carbide with a sulfonyl halide, hydrolyzing the product obtained, adding a compound M y Y m , in which Y represents an anion capable of reacting with the cation of the ionic carbide to the reaction medium before or after hydrolysis to give a compound which can be separated from compound (I), and y represents the valence of Y.
Inventors
- 👤 Michel Armand
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 23:57
CPC Classifications
C; C07; C07C; C07C315/00
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
277 words
A process for the synthesis of sulfonylmethane or derivatives thereof of the formula I: M[(RSO.sub.2).sub.2 CH].sub.m wherein M is at least one member selected from the group consisting of hydrogen, alkali metal, alkaline earth metal, quaternary ammonium anion NR' 4 , wherein moiety R' are at least one member selected from the group consisting of C 1 -C 8 aliphatic, C 3 -C 8 aryl and C 3 -C 8 alicyclic, wherein R is at least one member selected from the group consisting of C 1 -C 8 aliphatic, C 3 -C 8 aryl and C 3 -C 8 alicyclic, and wherein m represents the valence of M; said process comprising the steps of: (a) reacting an ionic carbide with a sulfonyl halide of the general formula RSO 2 X in a polar aprotic solvent, wherein said ionic carbide is at least one member selected from the group consisting of aluminum carbide, beryllium carbide, thorium carbide and uranium carbide, and wherein X is at least one member of the group consisting of Cl and F, and wherein R is as defined above; (b) hydrolyzing the product obtained from said reaction; (c) adding a compound of the formula M y Y m to the reaction mixture before or after said hydrolysis step, wherein M and m are as defined above, and Y is an anion capable of forming an insoluable compound with a cation of said ionic carbide and wherein y represents the valence of Y, M y Y m being an acid H y Y m when M is H and the compound to be synthesized is a sulfonylmethane of the formula (RSO 2 )CH 2 .
Claim 2
Dependent Claim
277 words
A process for the synthesis of sulfonylmethane or derivatives thereof of the formula I: M[(RSO.sub.2).sub.2 CH].sub.m wherein M is at least one member selected from the group consisting of hydrogen, alkali metal, alkaline earth metal, quaternary ammonium anion NR' 4 , wherein moiety R' are at least one member selected from the group consisting of C 1 -C 8 aliphatic, C 3 -C 8 aryl and C 3 -C 8 alicyclic, wherein R is at least one member selected from the group consisting of C 1 -C 8 aliphatic, C 3 -C 8 aryl and C 3 -C 8 alicyclic, and wherein m represents the valence of M; said process comprising the steps of: (a) reacting an ionic carbide with a sulfonyl halide of the general formula RSO 2 X in a polar aprotic solvent, wherein said ionic carbide is at least one member selected from the group consisting of aluminum carbide, beryllium carbide, thorium carbide and uranium carbide, and wherein X is at least one member of the group consisting of Cl and F, and wherein R is as defined above; (b) hydrolyzing the product obtained from said reaction; (c) adding a compound of the formula M y Y m to the reaction mixture before or after said hydrolysis step, wherein M and m are as defined above, and Y is an anion capable of forming an insoluable compound with a cation of said ionic carbide and wherein y represents the valence of Y, M y Y m being an acid H y Y m when M is H and the compound to be synthesized is a sulfonylmethane of the formula (RSO 2 )CH 2 .
Claim 3
Dependent Claim
34 words
The process of claim 1, wherein hydrolysis of process step (b) is accomplished by reaction with at least one member selected from the group consisting of water, hydrochloric acid, sulfuric acid and phosphoric acid.
Claim 4
Dependent Claim
12 words
The process of claim 1, wherein said ionic carbide is aluminum carbide.
Claim 5
Dependent Claim
9 words
The process of claim 1, wherein R is chlorinated.
Claim 6
Dependent Claim
9 words
The process of claim 1, wherein R is fluorinated.
Claim 7
Dependent Claim
15 words
The process of claim 1, wherein R is a perfluorinated C 1 -C 4 alkyl.
Claim 8
Dependent Claim
19 words
The process of claim 1, wherein said compound M y Y m is a salt of an alkali metal.
Claim 9
Dependent Claim
21 words
The process according to claim 1, wherein the compound M y Y m is a salt of an alkaline earth metal.
Claim 10
Dependent Claim
49 words
The process of claim 1, wherein M y Y m is a salt of a quaternary ammonium anion NR' 4 wherein R' are at least one member selected from the group consisting of C 1 -C 8 aliphatic, C 3 -C 8 aryl and C 3 -C 8 alicyclic.
Claim 11
Dependent Claim
19 words
The process of claim 1, wherein the compound M y Y m is a non-volatile acid H y Y.
Claim 12
Dependent Claim
25 words
The process of claim 1, wherein said polar aprotic solvent is at least one member selected from the group consisting of ethers, amides and dimethylsulfoxide.
Claim 13
Dependent Claim
31 words
The process of claim 11, wherein said polar aprotic solvent is at least one member selected from the group consisting of tetrahydrofuran, dimethoxyethane, glymes, dimethylformamide, dimethylpyrrolidone, tetramethylurea, dimethyleneurea, tetraethylsulfonamide and dimethylsulfoxide.
Claim 14
Dependent Claim
35 words
The process of claim 10, wherein the sulphonylmethane is further reacted with a member selected from the group consisting of a metal, metal oxide, metal hydroxide and metal carbonate, thereby yielding the corresponding metal/sulphonylmethane salt.
Claim 15
Dependent Claim
25 words
The process of claim 10, wherein said nonvolatile acid is at least one member selected from the group consisting of sulfuric acid and phosphoric acid.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1995-08-04 | 1996-02-03 | 1996-08-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-08-04 | 2000-02-03 | 2000-08-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-08-04 | 2004-02-03 | 2004-08-04 | $7700.00 | Window Closed / Lapsed |