GB892261A - A process for the preparation of hydroxyphenyl substituted methanes - Google Patents
A process for the preparation of hydroxyphenyl substituted methanesInfo
- Publication number
- GB892261A GB892261A GB26294/60A GB2629460A GB892261A GB 892261 A GB892261 A GB 892261A GB 26294/60 A GB26294/60 A GB 26294/60A GB 2629460 A GB2629460 A GB 2629460A GB 892261 A GB892261 A GB 892261A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- branched
- alkyl group
- ring
- butyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Abstract
Resins may be obtained by reacting aldehydes or ketones with bis-phenols of the formula <FORM:0892261/IV (a)/1> where the R groups are the same or different alkyl groups having up to 8 carbon atoms and where at least one alkyl group ortho to each hydroxyl group is branched on the carbon atom bound to the ring and has at least 3 carbon atoms, Specification 806,961 is referred to.ALSO:A process for preparing a hydroxyphenyl substituted methane comprises reacting a 3,5-dialkyl-mono-hydroxybenzyl alcohol of the formula <FORM:0892261/IV (b)/1> where R1 is an alkyl group having between 3 and 8 carbon atoms inclusive and is branched on the carbon atom bound to the ring, and one of R2 and R3 is an alkyl group having up to 8 carbon atoms and the other is a hydroxymethyl group, with an alkyl phenol having the structure <FORM:0892261/IV (b)/2> where either (i) R4=R1, R5=R2, R6=R3; or (ii) any two of R4, R5 and R6 are hydrogen and the other is an alkyl group having up to 8 carbon atoms; or (iii) R4 is an alkyl group having between 3 and 8 carbon atoms inclusive and is branched on the carbon atom bound to the ring and one of R5 and R6 is an alkyl group having up to 8 carbon atoms and the other is hydrogen, in the presence of a solvent consisting essentially of a secondary or tertiary alcohol or a mixture thereof and in the presence of a catalytic amount of a base. The structure of the product depends on the structure of reactants; thus when the two components are identical, i.e. self-condensation, the product is a 2,21- or 41,41-dihydroxy-tetraalkyl-diphenyl methane, when a monoalkyl phenol is used the product is a bis-(hydroxy-dialkylbenzyl)-monoalkyl phenol and when a dialkyl phenol is used the product is a 2,21-, 4,41- or 2,41-dihydroxy-tetra-alkyl-diphenyl methane. The invention includes novel compounds of the formula <FORM:0892261/IV (b)/3> where the R groups are the same or different alkyl groups having upto 8 carbon atoms and where at least one of the alkyl groups ortho to each hydroxyl group is branched on the carbon atom bound to the ring and has at least 3 carbon atoms; <FORM:0892261/IV (b)/4> where R1, R2, R4 and R5 are alkyl groups having up to 8 carbon atoms, R1 and R4 having between 3 and 8 carbon atoms inclusive and being branched on the carbon atom bound to the ring and R4 and R5 are different from R1 and R2; <FORM:0892261/IV (b)/5> where R1 is an alkyl group having from 3 to 8 carbon atoms inclusive and is branched on the carbon atom bound to the ring and R2 and R6 are alkyl groups having up to 8 carbon atoms. The reaction takes place by heating stoichio-metric proportions of reactants, e.g. at 50 DEG C.-100 DEG C. in alcohol which may correspond to the secondary or tertiary substituent on the reactants, e.g. tert.-butanol in the case of tert. butyl substituted phenols and benzyl alcohols, using up to about 1% by weight of base, e.g. KOH, K2CO3 or an organic base, based on the benzyl alcohol. Examples describe the preparation of the 3,5,31,51-tetra-t. butyl, 3,31-di-t. amyl-5,51-dimethyl, 3,31-di-isopropyl-5,51-dimethyl, 3,5-dimethyl-31,51-di-t. butyl, 3,31,5-tri-t. butyl-51-methyl and 3,5-di-isopropyl-31,51-di-t. butyl derivatives of 4,41-dihydroxy-diphenyl-methane, and of the 3,31,5,51-tetra-t. butyl derivatives of 2,21- and 2,41-dihydroxy-diphenyl-methane. The 2,41-dihydroxy compounds may be reacted with epichlorhydrin to give monoglycidyl ethers. Specification 806,961 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US892261XA | 1959-07-30 | 1959-07-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB892261A true GB892261A (en) | 1962-03-21 |
Family
ID=22216421
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB26294/60A Expired GB892261A (en) | 1959-07-30 | 1960-07-28 | A process for the preparation of hydroxyphenyl substituted methanes |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB892261A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4173541A (en) | 1978-06-05 | 1979-11-06 | Cincinnati Milacron Chemicals Inc. | Polynuclear hindered phenols and stabilized organic materials containing the phenols |
-
1960
- 1960-07-28 GB GB26294/60A patent/GB892261A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4173541A (en) | 1978-06-05 | 1979-11-06 | Cincinnati Milacron Chemicals Inc. | Polynuclear hindered phenols and stabilized organic materials containing the phenols |
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