US4562281A
Expired / Lapsed
US
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Production of bisphenol derivatives
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1983-12-14
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Granted: 1985-12-31
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Expires: 2003-12-14
Abstract
Abstract Bisphenol derivatives of the formula (I), ##STR1## are produced by reacting a carboxylic acid, RCOOH (II), with a bisphenol of the formula (III), ##STR2## adding a halogenating agent in the presence of a dehydrohalogenating agent. The product bisphenol derivatives are useful as antioxidants.
Inventors
- 👤 Yukoh Takahashi
- 👤 Yutaka Terada
- 👤 Shinichi Yachigo
- 👤 Tamaki Ishii
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 14:06
CPC Classifications
C; C07; C07C; C07C67/00; C07C67/08
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
142 words
A method for producing bisphenol derivatives represented by the formula (I), ##STR6## wherein R represents an alkyl group having 1 to 3 carbon atoms, alkenyl group having 2 to 4 carbon atoms, phenyl group or 2-phenyl-ethenyl group, and R' represents an alkyl group having 1 to 4 carbon atoms, characterized in that a carboxylic acid represented by the formula (II), ##STR7## wherein R has the same meaning as above, is reacted at a temperature of -20° C. to 150° C. with a bisphenol represented by the formula (III), ##STR8## wherein R' has the same meaning as above, adding a halogenating agent selected from the group consisting of phosphoryl chlorides, phosphoryl bromides and toluenesulfonyl chloride to the reaction mixture, wherein the reaction is carried out in the presence of a dehydrohalogenating agent selected from the group consisting of tertiary amines and pyridine derivatives.
Claim 2
Independent Claim
142 words
A method for producing bisphenol derivatives represented by the formula (I), ##STR6## wherein R represents an alkyl group having 1 to 3 carbon atoms, alkenyl group having 2 to 4 carbon atoms, phenyl group or 2-phenyl-ethenyl group, and R' represents an alkyl group having 1 to 4 carbon atoms, characterized in that a carboxylic acid represented by the formula (II), ##STR7## wherein R has the same meaning as above, is reacted at a temperature of -20° C. to 150° C. with a bisphenol represented by the formula (III), ##STR8## wherein R' has the same meaning as above, adding a halogenating agent selected from the group consisting of phosphoryl chlorides, phosphoryl bromides and toluenesulfonyl chloride to the reaction mixture, wherein the reaction is carried out in the presence of a dehydrohalogenating agent selected from the group consisting of tertiary amines and pyridine derivatives.
Claim 3
Dependent Claim
17 words
A method as described in claim 1, wherein the halogenating agent is phosphorus oxychloride or phosphorus oxybromide.
Claim 4
Dependent Claim
17 words
A method as described in claim 1, wherein the halogenating agent is o-toluenesulfonyl chloride or p-toluenesulfonyl chloride.
Claim 5
Dependent Claim
39 words
A method as described in claim 1, wherein the carboxylic acid is one member selected from the group consisting of acetic acid, propionic acid, butyric acid, acrylic acid, methacrylic acid, crotonic acid, 3-butenoic acid, benzoic acid and cinnamic acid.
Claim 6
Dependent Claim
26 words
A method as described in claim 1, wherein the bisphenol is one member selected from the group consisting of 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 2,2'-methylenebis(6-tert-butyl-4-ethylphenol), 2,2'-methylenebis(6-tert-butyl-4-propylphenol), 2,2'-methylenebis(6-tert-butyl-4-n-butylphenol), 2,2'-methylenebis(6-tert-butyl-4-sec-butylphenol) and 2,2'-methylenebis(4,6-di-tert-butylphenol).
Claim 7
Dependent Claim
25 words
A method as described in claim 1, wherein the tertiary amine is one member selected from the group consisting of triethylamine, dimethylaniline, N,N-dimethylbenzylamine and tetramethylurea.
Claim 8
Dependent Claim
23 words
A method as described in claim 1, wherein the pyridine derivative is one member selected from the group consisting of pyridine and 4-(N,N-dimethylamino)pyridine.
Claim 9
Dependent Claim
18 words
A method as described in claim 1, wherein the molar ratio of carboxylic acid to bisphenol is 0.7-1.5:1.
Claim 10
Dependent Claim
30 words
A method as described in claim 2, wherein the amount of phosphorus oxychloride or phosphorus oxybromide used is 0.5 to 1.0 mole based on 1 mole of the carboxylic acid.
Claim 11
Dependent Claim
29 words
A method as described in claim 3, wherein the amount of o- or p-toluenesulfonyl chloride used is 0.8 to 1.6 moles based on 1 mole of the carboxylic acid.
Claim 12
Dependent Claim
28 words
A method as described in claim 2, wherein the amount of the dehydrohalogenating agent used is 2.7 to 3.6 equivalents based on 1 mole of the halogenating agent.
Claim 13
Dependent Claim
28 words
A method as described in claim 3, wherein the amount of the dehydrohalogenating agent used is 0.8 to 2.4 equivalents absed on 1 mole of the halogenating agent.
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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) | 1988-12-30 | 1989-07-01 | 1989-12-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-12-30 | 1993-07-01 | 1993-12-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-12-30 | 1997-07-01 | 1997-12-31 | $7700.00 | Window Closed / Lapsed |