US4358616A
Expired / Lapsed
US
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Process for the preparation of alkylthiomethylphenols and arylthiomethylphenols
Assignee: Bayer AG
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Filing: 1980-12-01
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Granted: 1982-11-09
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Expires: 2000-12-01
Abstract
Abstract The present invention provides a process for the preparation of an alkylthiomethylphenol or arylthiomethylphenol of the general formula ##STR1## in which m, n, R and R 1 have the meaning mentioned in the specification, in which a hydroxymethylphenol of the general formula ##STR2## is reacted with a mercaptan or thiophenol at a temperature of from 20° to 200° C., if appropriate in the presence of a diluent.
Inventors
- 👤 Karlfried Wedemeyer
- 👤 Helmut Fiege
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 02:01
CPC Classifications
C; C07; C07C; C07C323/00
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
128 words
Process for the preparation of a thio-methylphenol compound of the formula ##STR6## wherein m is 1, 2 or 3; each R is individually selected from hydrogen, alkyl, cycloalkyl, aryl, aralkyl, alkoxy, cycloalkoxy, aryloxy, halogen or nitro; or the R's taken together represent a benzene ring or a cycloalkane ring fused to the phenyl ring of formula (I); and R 1 is alkyl of 1-12 carbon atoms, alkoxy-substituted alkyl of 1-12 carbon atoms, cycloalkyl; phenyl; halogen-substituted phenyl; or aralkyl, which process comprises, in the absence of a catalyst, reacting an hydroxymethylphenol of the formula ##STR7## wherein R and m are defined as above with a mercaptan or thiophenol of the formula R.sup.1 --S--H where R 1 is defined as above, at a temperature from 50° C. to 200° C.
Claim 2
Dependent Claim
128 words
Process for the preparation of a thio-methylphenol compound of the formula ##STR6## wherein m is 1, 2 or 3; each R is individually selected from hydrogen, alkyl, cycloalkyl, aryl, aralkyl, alkoxy, cycloalkoxy, aryloxy, halogen or nitro; or the R's taken together represent a benzene ring or a cycloalkane ring fused to the phenyl ring of formula (I); and R 1 is alkyl of 1-12 carbon atoms, alkoxy-substituted alkyl of 1-12 carbon atoms, cycloalkyl; phenyl; halogen-substituted phenyl; or aralkyl, which process comprises, in the absence of a catalyst, reacting an hydroxymethylphenol of the formula ##STR7## wherein R and m are defined as above with a mercaptan or thiophenol of the formula R.sup.1 --S--H where R 1 is defined as above, at a temperature from 50° C. to 200° C.
Claim 3
Dependent Claim
17 words
Process as claimed in claim 1 wherein the process carried out in the presence of a diluent.
Claim 4
Dependent Claim
20 words
Process as claimed in claim 1 wherein the process is carried out at a temperature of up to 180° C.
Claim 5
Dependent Claim
61 words
Process as claimed in claim 1 wherein the reaction is effected in the presence of a diluent selected from at least one member of the group consisting of water, an aliphatic aromatic or cycloaliphatic hydrocarbon, which may be chlorinated, an alcohol, an ether, an ether-alcohol, a phenol, a ketone, an amide, a nitrile or a mixture of any of these diluents.
Claim 6
Dependent Claim
18 words
Process as claimed in claim 1 wherein an excess of the mercaptan (III) is employed as the diluent.
Claim 7
Dependent Claim
20 words
Process as claimed in claim 1 wherein a weight ratio of diluent to hydroxymethylphenol of 1:1 to 20:1 is employed.
Claim 8
Dependent Claim
16 words
Process as claimed in claim 1-6 wherein the hydroxymethylphenol of formula (II) is prepared in situ.
Claim 9
Dependent Claim
10 words
Process as claimed in claim 1 wherein m is 1.
Claim 10
Dependent Claim
10 words
Process as claimed in claim 1 wherein m is 2.
Claim 11
Dependent Claim
10 words
Process as claimed in claim 1 wherein m is 3.
Claim 12
Dependent Claim
10 words
Process as claimed in claim 1 wherein R is hydrogen.
Claim 13
Dependent Claim
10 words
Process as claimed in claim 1 wherein R is alkyl.
Claim 14
Dependent Claim
10 words
Process as claimed in claim 1 wherein R is cycloalkyl.
Claim 15
Dependent Claim
10 words
Process as claimed in claim 1 wherein R is aryl.
Claim 16
Dependent Claim
10 words
Process as claimed in claim 1 wherein R is aralkyl.
Claim 17
Dependent Claim
10 words
Process as claimed in claim 1 wherein R is alkoxy.
Claim 18
Dependent Claim
10 words
Process as claimed in claim 1 wherein R is cycloalkoxy.
Claim 19
Dependent Claim
10 words
Process as claimed in claim 1 wherein R is aryloxy.
Claim 20
Dependent Claim
12 words
Process as claimed in claim 1 wherein R is halogen or nitro.
Claim 21
Dependent Claim
15 words
Process as claimed in claim 1 wherein the R's taken together represent a benzene ring.
Claim 22
Dependent Claim
15 words
Process as claimed in claim 1 wherein the R's taken together represent a cycloalkane ring.
Claim 23
Dependent Claim
15 words
Process as claimed in claim 1 wherein R 1 is alkyl or alkoxy substituted alkyl.
Claim 24
Dependent Claim
11 words
Process as claimed in claim 1 wherein R 1 is cycloalkyl.
Claim 25
Dependent Claim
15 words
Process as claimed in claim 1 wherein R 1 is phenyl or halogen substituted phenyl.
Claim 26
Dependent Claim
11 words
Process as claimed in claim 1 wherein R 1 is aralkyl.
Claim 27
Dependent Claim
113 words
Process for the preparation of a thiomethylphenol compound of the formula ##STR8## wherein m is 1, 2 or 3; each R is individually selected from hydrogen, cycloalkyl, aryl, aralkyl, alkoxy, cycloalkoxy, aryloxy, halogen or nitro; or the R's taken together represent a benzene ring or a cycloalkane ring fused to the phenyl ring of formula (I); and R 1 is halogen substituted phenyl; which process comprises in the absence of a catalyst, reacting an hydromethylphenol of the formula ##STR9## wherein R and m are defined as above with a mercaptan or thiophenol of the formula R.sup.1 --S--H (III) wherein R 1 is defined as above, at a temperature from 20° to 200° C.
Claim 28
Dependent Claim
113 words
Process for the preparation of a thiomethylphenol compound of the formula ##STR8## wherein m is 1, 2 or 3; each R is individually selected from hydrogen, cycloalkyl, aryl, aralkyl, alkoxy, cycloalkoxy, aryloxy, halogen or nitro; or the R's taken together represent a benzene ring or a cycloalkane ring fused to the phenyl ring of formula (I); and R 1 is halogen substituted phenyl; which process comprises in the absence of a catalyst, reacting an hydromethylphenol of the formula ##STR9## wherein R and m are defined as above with a mercaptan or thiophenol of the formula R.sup.1 --S--H (III) wherein R 1 is defined as above, at a temperature from 20° to 200° C.
Claim 29
Dependent Claim
61 words
Process as claimed in claim 26, wherein the reaction is effected in the presence of a diluent selected from at least one member of the group consisting of water, an aliphatic, aromatic or cycloaliphatic hydrocarbon, which may be chlorinated, an alcohol, an ether, an ether-alcohol, a phenol, a ketone, an amide, a nitrile or a mixture of any of these diluents.
Claim 30
Dependent Claim
31 words
Process as claimed in claim 26 where the hydroxymethylphenol of the formula (II) is further defined by having at least one of the ortho or para-positions to the hydroxyl be hydrogen.
Claim 31
Dependent Claim
31 words
Process as claimed in claim 1 wherein the hydroxymethylphenol of the formula (II) is further defined by having at least one of the ortho- or para-positions to the hydroxyl be hydrogen.
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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) | 1985-11-08 | 1986-05-10 | 1986-11-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-11-08 | 1990-05-10 | 1990-11-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-11-08 | 1994-05-10 | 1994-11-09 | $7700.00 | Window Closed / Lapsed |