US5712419A
Expired / Lapsed
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Method of making coupled 4,6-dibenzoylresorcinols
Assignee: General Electric Co
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Filing: 1996-12-23
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Granted: 1998-01-27
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Expires: 2016-12-23
Abstract
Abstract An improved method of making methylene-bridged 4,6-dibenzoylresorcinol dimers in a single step in high yield quantities is provided. The method heats a 4,6-dibenzoylresorcinol (DBR) with a para-aldehyde or an aromatic aldehyde in a carboxylic acid solvent in the presence of a strong acid catalyst.
Inventors
- 👤 James Edward Pickett
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 12:31
CPC Classifications
C; C07; C07C; C07C49/00; C07C49/76; C07C49/82; C07C49/83; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/72; C07C45/75
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
131 words
An improved method of making a methylene-bridged dimer of a 4,6-dibenzoylresorcinol comprising the step of: heating a mixture of a 4,6-dibenzoylresorcinol and about one-half molar equivalent or greater of an alkyl para-aldehyde or aromatic aldehyde with an acid in a solvent at a temperature between about 80° C. and reflux for a sufficient amount of time to make a methylene-bridged dimer of 4,6-dibenzoylresorcinol, said 4,6-dibenzoylresorcinol having the formula ##STR8## where Ar 1 and Ar 2 are independently substituted or unsubstituted monocyclic or polycyclic aryl groups, and said methylene-bridged dimer of 4,6-dibenzoylresorcinol having the formula ##STR9## where Ar 1 and Ar 2 are independently substituted or unsubstituted monocyclic or polycyclic aryl groups, and R is H, an aryl group or a linear or branched alkyl chain having less than about 10 carbons.
Claim 2
Dependent Claim
131 words
An improved method of making a methylene-bridged dimer of a 4,6-dibenzoylresorcinol comprising the step of: heating a mixture of a 4,6-dibenzoylresorcinol and about one-half molar equivalent or greater of an alkyl para-aldehyde or aromatic aldehyde with an acid in a solvent at a temperature between about 80° C. and reflux for a sufficient amount of time to make a methylene-bridged dimer of 4,6-dibenzoylresorcinol, said 4,6-dibenzoylresorcinol having the formula ##STR8## where Ar 1 and Ar 2 are independently substituted or unsubstituted monocyclic or polycyclic aryl groups, and said methylene-bridged dimer of 4,6-dibenzoylresorcinol having the formula ##STR9## where Ar 1 and Ar 2 are independently substituted or unsubstituted monocyclic or polycyclic aryl groups, and R is H, an aryl group or a linear or branched alkyl chain having less than about 10 carbons.
Claim 3
Dependent Claim
22 words
An improved method of making a methylene-bridged dimer of a 4,6-dibenzoylresorcinol according to claim 1 where the temperature is about 80°-180° C.
Claim 4
Dependent Claim
21 words
An improved method of making a methylene-bridged dimer of a 4,6-dibenzoylresorcinol according to claim 1 where the alkyl para-aldehyde is paraformaldehyde.
Claim 5
Dependent Claim
21 words
An improved method of making a methylene-bridged dimer of a 4,6-dibenzoylresorcinol according to claim 1 where the aromatic aldehyde is benzaldehyde.
Claim 6
Dependent Claim
22 words
An improved method of making a methylene-bridged dimer of a 4,6-dibenzoylresorcinol according to claim 1 where the solvent is a carboxylic acid.
Claim 7
Dependent Claim
21 words
An improved method of making a methylene-bridged dimer of a 4,6-dibenzoylresorcinol according to claim 5 where the solvent is acetic acid.
Claim 8
Dependent Claim
21 words
An improved method of making a methylene-bridged dimer of a 4,6-dibenzoylresorcinol according to claim 1 where the acid is sulfuric acid.
Claim 9
Dependent Claim
58 words
An improved method of making a methylene-bridged dimer of a 4,6-dibenzoylresorcinol according to claim 3 where the methylene-bridged dimer of 4,6-dibenzoylresorcinol has the formula ##STR10## where Ar 1 and Ar 2 are independently substituted or unsubstituted monocyclic or polycyclic aryl groups, and R is H, or a linear or branched alkyl chain having less than about 10 carbons.
Claim 10
Dependent Claim
23 words
An improved method of making a methylene-bridged dimer of a 4,6-dibenzoylresorcinol according to claim 8 where the methylene-bridged dimer of 4,6-dibenzoylresorcinol is bis(2,6-dihydroxy-3,5-dibenzoylphenyl)methane.
Claim 11
Dependent Claim
31 words
An improved method of making a methylene-bridged dimer of a 4,6-dibenzoylresorcinol according to claim 4 where the methylene-bridged dimer of 4,6-dibenzoylresorcinol has the formula ##STR11## where Ar 1 ═Ar 2 ═R═phenyl.
Claim 12
Dependent Claim
23 words
An improved method of making a methylene-bridged dimer of a 4,6-dibenzoylresorcinol according to claim 10 where the methylene-bridged dimer of 4,6-dibenzoylresorcinol is bis(2,6-dihydroxy-3,5-dibenzoylphenyl)phenylmethane.
Claim 13
Dependent Claim
22 words
An improved method of making a methylene-bridged dimer of a 4,6-dibenzoylresorcinol according to claim 1 where the solvent is excess aromatic aldehyde.
Claim 14
Independent Claim
53 words
A method for preparing ultraviolet light absorbers, comprising the step of mixing an admixture of a substituted or unsubstituted aryl group on a 4,6-dibenzoylresorcinol, an acid catalyst, an organic solvent, and sufficient para-aldehyde or aromatic aldehyde at a temperature and for a time sufficient to form a methylene bridged dimer of a 4,6-dibenzoylresorcinol.
Claim 15
Independent Claim
53 words
A method for preparing ultraviolet light absorbers, comprising the step of mixing an admixture of a substituted or unsubstituted aryl group on a 4,6-dibenzoylresorcinol, an acid catalyst, an organic solvent, and sufficient para-aldehyde or aromatic aldehyde at a temperature and for a time sufficient to form a methylene bridged dimer of a 4,6-dibenzoylresorcinol.
Claim 16
Dependent Claim
95 words
An improved method of making a mixed methylene-coupled DBR derivative comprising the step: heating a mixture of 4,6-dibenzoylresorcinol derivatives and about one-half molar equivalent or greater of an alkyl para-aldehyde or aromatic aldehyde with an acid in a solvent at a temperature between about 80° C. and reflux for a sufficient amount of time to make unsymmetrical substituted methylene-bridged derivatives having a formula ##STR12## where Ar 1 , Ar 2 , Ar 3 , Ar 4 are independently substituted or unsubstituted aromatic rings and R is H, C1 to C12 alkyl, or an aryl group.
Claim 17
Dependent Claim
95 words
An improved method of making a mixed methylene-coupled DBR derivative comprising the step: heating a mixture of 4,6-dibenzoylresorcinol derivatives and about one-half molar equivalent or greater of an alkyl para-aldehyde or aromatic aldehyde with an acid in a solvent at a temperature between about 80° C. and reflux for a sufficient amount of time to make unsymmetrical substituted methylene-bridged derivatives having a formula ##STR12## where Ar 1 , Ar 2 , Ar 3 , Ar 4 are independently substituted or unsubstituted aromatic rings and R is H, C1 to C12 alkyl, or an aryl group.
Claim 18
Dependent Claim
20 words
An improved method of making a mixed methylene-coupled DBR derivative according to claim 14 where the alkyl para-aldehyde is paraformaldehyde.
Claim 19
Dependent Claim
20 words
An improved method of making a mixed methylene-coupled DBR derivative according to claim 14 where the aromatic aldehyde is benzaldehyde.
Claim 20
Dependent Claim
21 words
An improved method of making a mixed methylene-coupled DBR derivative according to claim 14 where the solvent is a carboxylic acid.
Claim 21
Dependent Claim
20 words
An improved method of making a mixed methylene-coupled DBR derivative according to claim 17 where the solvent is acetic acid.
Claim 22
Dependent Claim
20 words
An improved method of making a mixed methylene-coupled DBR derivative according to claim 14 where the acid is sulfuric acid.
Claim 23
Dependent Claim
21 words
An improved method of making a mixed methylene-coupled DBR derivative according to claim 14 where the solvent is excess aromatic aldehyde.
References Cited (Backward Citations)
US3506610A
Cited
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