US4684752A
Expired / Lapsed
US
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Di-ortho-substituted di-meta-halogenated para-halomethylphenols
Assignee: Huntsman Advanced Materials Americas LLC
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Filing: 1986-04-30
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Granted: 1987-08-04
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Expires: 2006-04-30
Abstract
Abstract Included is a process to prepare a 4-HALOmethyl-3,5-dihalo-2,6-disubstitutedphenol from a 4-methyl(substituted)phenol and a HALOgenating agent, in an aprotic organic diluent. The process is highly selective and efficient. For example, high purity 4-bromomethyl-3,5-dibromo-2,6-dimethylphenol can be prepared from 2,4,6-trimethylphenol and bromine, in bromochloromethane at high conversion.
Inventors
- 👤 Abel Mendoza
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 05:31
CPC Classifications
C; C07; C07C; C07C39/00; C07C39/02; C07C37/00; C07C37/62
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
30 words
A process to prepare a 4-HALOmethyl-3, 5-dihalo-2, 6-disubstitutedphenol comprising contacting a 4-methyl(substituted)phenol with a HALOgenating agnet, in an aprotic organic diluent, under conditions whereby the 4-HALOmethyl-3, 5-dihalo-2, 6-disubstitutedphenol is prepared.
Claim 2
Dependent Claim
30 words
A process to prepare a 4-HALOmethyl-3, 5-dihalo-2, 6-disubstitutedphenol comprising contacting a 4-methyl(substituted)phenol with a HALOgenating agnet, in an aprotic organic diluent, under conditions whereby the 4-HALOmethyl-3, 5-dihalo-2, 6-disubstitutedphenol is prepared.
Claim 3
Dependent Claim
90 words
The process of claim 1 wherein the 4-HALOmethyl-3, 5-dihalo-2, 6-disubstituted phenol is of the ##STR4## and the 4-methyl(substituted)phenol is of the formula ##STR5## wherein Q is separately at each occurrence in each formula C 1-12 alkyl with the carbon bonded directly to the phenol ring selected from the group consisting of primary and secondary carbons, or C 1-12 generally inertly-substituted alkyl; Q' is separately at each occurrence hydrogen, fluoro, chloro or bromo; X is separately at each occurrence fluoro, chloro or bromo; and X' is separately at each occurrence HALO,
Claim 4
Dependent Claim
15 words
The process of claim 2 wherein at least one q' is fluoro, chloro or bromo.
Claim 5
Dependent Claim
31 words
The process of claim 3 wherein the HALOgenating agent is a molecular HALOgen contacted with the 4-methyl(substituted)phenol in a mole ratio of molecular HALOgen to 4-methyl(substituted)phenol of about 5:1 or lower.
Claim 6
Dependent Claim
13 words
The process of claim 4 wherein the aprotic organic diluent is a haloalkane.
Claim 7
Dependent Claim
12 words
The process of claim 5 wherein the HALOgenating agent is elemental bromine.
Claim 8
Dependent Claim
9 words
The process of claim 6 wherein Q is methyl.
Claim 9
Dependent Claim
37 words
The process of claim 7 wherein conversion of the 4-methyl(substituted)phenol is about 65 percent or above, by weight, and selectivity of the converted product to the 4-HALOmethyl-3, 5-dihalo-2, 6-disubstitutedphenol is about 90 percent or above, by weight.
Claim 10
Dependent Claim
9 words
The process of claim 8 wherein Q' is bromo.
Claim 11
Dependent Claim
14 words
The process of claim 9 wherein the selectivity is about 95 percent or above.
Claim 12
Dependent Claim
9 words
The process of claim 2 wherein Q' is hydro.
Claim 13
Dependent Claim
26 words
The process of claim 11 wherein the HALOgenating agent is a molecular HALOgen contacted with the 4-methyl(substituted)phenol in a mole ratio of about 7:1 or lower.
Claim 14
Dependent Claim
17 words
The process of claim 12 wherein the aprotic organic diluent is a haloalkane, and X is HALO.
Claim 15
Dependent Claim
17 words
The process of claim 13 wherein the HALOgenating agent is elemental bromine, and the HALO is bromo.
Claim 16
Dependent Claim
9 words
The process of claim 14 wherein Q is methyl.
Claim 17
Dependent Claim
37 words
The process of claim 15 wherein conversion of the 2, 4, 6-trimethylphenol is about 65 percent or above, by weight, and selectivity of the converted product to 4-bromomethyl-3, 5-di-bromo-2, 6-dimethylphenol is 90 percent or above, by weight.
Claim 18
Dependent Claim
30 words
A process to prepare 4-bromomethyl-3, 5-dibromo-2, 6-dimethylphenol comprising contacting 2, 4, 6-trimethylphenol with a brominating agent in an aprotic organic diluent under conditions whereby the 4-bromomethyl-3, 5-dibromo-2, 6-dimethylphenol is prepared.
Claim 19
Dependent Claim
30 words
A process to prepare 4-bromomethyl-3, 5-dibromo-2, 6-dimethylphenol comprising contacting 2, 4, 6-trimethylphenol with a brominating agent in an aprotic organic diluent under conditions whereby the 4-bromomethyl-3, 5-dibromo-2, 6-dimethylphenol is prepared.
Claim 20
Dependent Claim
46 words
The process of claim 17 wherein the brominating agent is elemental bromine; the aprotic organic diluent is a -haloalkane; conversion of 2, 4, 6-trimethylphenol is 50 percent or above, by weight, and selectivity to the 4-bromomethyl-3, 5-dibromo-2, 6-dimethylphenol is about 95 percent or above, by weight.
Claim 21
Dependent Claim
13 words
The process of claim 18 wherein the conversion is 60 percent or above.
Claim 22
Dependent Claim
28 words
The process of claim 17 wherein the haloalkane is bromochloromethane, and upon recrystallization in methylene chloride, the purity of the 4-bromomethyl-3, 5-dibromo-2, 6-dimethylphenol is 99 percent or greater.
Claim 23
Dependent Claim
30 words
A process to prepare a 4-methyl-3, 5-dihalo-2, 6-disubstitutedphenol comprising contacting a 4-methyl(substituted)phenol with a halogenating agent, in an aprotic organic diluent, under conditions whereby the 4-methyl-3, 5-dihalo-2, 6-disubstitudphenol is prepared.
Claim 24
Dependent Claim
30 words
A process to prepare a 4-methyl-3, 5-dihalo-2, 6-disubstitutedphenol comprising contacting a 4-methyl(substituted)phenol with a halogenating agent, in an aprotic organic diluent, under conditions whereby the 4-methyl-3, 5-dihalo-2, 6-disubstitudphenol is prepared.
Claim 25
Dependent Claim
88 words
The process of claim 21 wherein the 4-methyl-3, 5-dihalo-2, 6-disubsitiuted phenol is of the formula ##STR6## and the 4-methyl(substituted)phenol is of the formula ##STR7## wherein Q is separately at each occurrence in each formula C 1-12 alkyl with the carbon bonded directly to the phenol ring selected from the group consisting of primary and secondary carbons, or C 1-12 generally inertly-subsitiuted alkyl; Q' is hydrogen, fluoro, chloro or bromo; provided that at least one Q' is hydrogen, and X is separately at each occurrence fluoro, chloro or bromo.
Claim 26
Dependent Claim
55 words
The process of claim 22 wherein the halogenating agent is a molecular HALOgen contacted with the 4-methyl(substituted)phenol in a mole ratio of molecular HALOgen to 4-methyl(substituted)phenol of about 1:1 to about 2:1; the aprotic organic diluent is a haloalkane, and the yield of the 4-methyl-3, 5-dihalo-2, 6-disubstitutedphenol is about 65 percent or above by weight.
Claim 27
Dependent Claim
16 words
The process of claim 23 wherein Q is methyl, and the molecular HALOgen is elemental bromine.
Claim 28
Dependent Claim
17 words
The process of claim 24 wherein Q' is hydro; X is bromo, and the haloalkane is bromochloromethane.
References Cited (Backward Citations)
GB411430A
Cited
GB443113A
Cited
US2841623A
Cited
US3360573A
Cited
NL6503461A
Cited
US3751488A
Cited
US3764630A
Cited
US3899540A
Cited
US3976702A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-08-03 | 1991-02-02 | 1991-08-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-08-03 | 1995-02-02 | 1995-08-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-08-03 | 1999-02-02 | 1999-08-04 | $7700.00 | Window Closed / Lapsed |