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GB1084433A - Manufacture of biphenols - Google Patents

Manufacture of biphenols

Info

Publication number
GB1084433A
GB1084433A GB3538764A GB3538764A GB1084433A GB 1084433 A GB1084433 A GB 1084433A GB 3538764 A GB3538764 A GB 3538764A GB 3538764 A GB3538764 A GB 3538764A GB 1084433 A GB1084433 A GB 1084433A
Authority
GB
United Kingdom
Prior art keywords
butyl
biphenol
phenol
yield
treatment
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
Application number
GB3538764A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
General Electric Co
Original Assignee
General Electric Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by General Electric Co filed Critical General Electric Co
Publication of GB1084433A publication Critical patent/GB1084433A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
    • C10L1/1835—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom having at least two hydroxy substituted non condensed benzene rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
    • C07C37/07—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation with simultaneous reduction of C=O group in that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C46/00—Preparation of quinones
    • C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
    • C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring
    • C07C46/08—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring with molecular oxygen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00—Quinones
    • C07C50/08—Quinones with polycyclic non-condensed quinoid structure
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/19—Hydroxy compounds containing aromatic rings
    • C08G63/193—Hydroxy compounds containing aromatic rings containing two or more aromatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

The new compounds 2,21,6,61-tetraphenyl-p,p1-diphenol and 2,21-diphenyl-p,p1-diphenol (see Division C2) are used as components in the manufacture of polycarbonate, polyester and polyepoxide resins by the known methods for making such resins, of which methods various details are given. The polyesters are those of aromatic dicarboxylic acid, e.g. ortho-, iso- or tere-phthalic acids.ALSO:A phenol, which may be substituted in one or two of the 2-, 4- and 6-positions with one or two alkyl, alkoxy, aryl or aryloxy groups, is reacted in the liquid phase with a diphenoquinone (cf. Specification 930,993) carrying alkyl, alkoxy, aryl or aryloxy substituents in the 3-, 31-, 5- and 51-positions, whereby biphenols or mixtures of biphenols are obtained. A typical reaction is <FORM:1084433/C2/1> in which R and R1 are substituents, as defined above. The reaction may be effected in the presence of an acid or basic catalyst, pyridine and homologous bases being the preferred catalysts. A solvent may also be present, and this may be an excess of the phenol. The reaction may be effected at atmospheric pressure at a temperature from 100 DEG C. up to the reflux temperature. Alternatively, the reaction may be effected in a sealed tube. The biphenols produced in the reaction may be dealkylated, if desired. In typical examples: (1) 2,6-di-t-butyl-phenol and 3,31,5,51-tetra-t-butyldiphenoquinone yield 2,21,6,61-tetra-t-butyl-p,p1-biphenol, (2) phenol and 3,31,5,51-tetra-t-butyldiphenoquinone yield a mixture containing p,p1, o,p1- and o,o1-biphenols and 2,21,6, 61-tetra - t - butyl - p,p1 - biphenol, (3) 2,6 - diphenylphenol and 3,31,5,51 - tetraphenyldiphenoquinone yield 2,21,6,61 - tetraphenyl-p, p1-biphenol, the purification of which by way of the diacetate (by treatment with acetic anhydride) is described, (4) 2-t-butyl-6-phenyl-phenol and 3,31-di-t-butyl-5,51-diphenyldiphenoquinone yield 2,21-di-t-butyl-6,61-diphenyl-p, p1-biphenol, which is then dealkylated by treatment with aluminium phenoxide or isopropoxide to yield 2,21-diphenyl-p,p1-biphenol, which is purified by way of its diacetate (by treatment with acetic anhydride), and (5) the product of Example 1 is dealkylated by treatment with aluminium isopropoxide to yield p,p1-biphenol. The use of 2,21,6,61 - tetraphenyl - p,p1 - biphenol in the manufacture of polycarbonate, polyester and epoxy resins is described (see Division C3). Examples are given also of the preparation of the following intermediates. 2 - t - Butyl - 6 - phenylphenol is prepared from o-phenylphenol and isobutylene in the presence of aluminium o-phenylphenoxide. 2 - t - Butyl - 6 - methylphenol and 2,6 - di - t-butylphenol are prepared similarly. 3,31 - Di - t - butyl - 5,51 - diphenyldiphenoquinone is prepared from 2-t-butyl-6-phenyl-phenol by treatment with oxygen in the presence of cuprous chloride and tetramethylethylene diamine. 3,31,5,51-Tetra-t-butyldiphenoquinone is prepared similarly. 3,31 - Di - t - butyl - 5,51 - dimethyldiphenoquinone is prepared from 2-t-butyl-6-methylphenol by treatment with oxygen in the presence of cuprous chloride and dimethylacetamide or pyridine.
GB3538764A 1963-09-03 1964-08-28 Manufacture of biphenols Expired GB1084433A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US30630163A 1963-09-03 1963-09-03
US30630263A 1963-09-03 1963-09-03

Publications (1)

Publication Number Publication Date
GB1084433A true GB1084433A (en) 1967-09-20

Family

ID=26975085

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3538764A Expired GB1084433A (en) 1963-09-03 1964-08-28 Manufacture of biphenols

Country Status (3)

Country Link
DE (1) DE1493767A1 (en)
GB (1) GB1084433A (en)
NL (1) NL6410238A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0131897A1 (en) * 1983-07-15 1985-01-23 Ici Americas Inc. High yield process for preparing 3,3',5,5'-tetraalkyl-4,4'-biphenol
JP2016511248A (en) * 2013-02-21 2016-04-14 シーアン リーバン ファーマシューティカル カンパニー リミテッド Novel crystal form of 3,3 ', 5,5'-tetraisopropyl-4,4'-biphenol and process for producing the same
WO2023036868A1 (en) * 2021-09-10 2023-03-16 Reuter Chemische Apparatebau E.K. (het)aryl substituted bisphenol compounds and thermoplastic resins
CN118930411A (en) * 2024-10-09 2024-11-12 北京弗莱明科技有限公司 A method for producing 4,4'-biphenyl diphenol by efficient debutylation

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0131897A1 (en) * 1983-07-15 1985-01-23 Ici Americas Inc. High yield process for preparing 3,3',5,5'-tetraalkyl-4,4'-biphenol
JP2016511248A (en) * 2013-02-21 2016-04-14 シーアン リーバン ファーマシューティカル カンパニー リミテッド Novel crystal form of 3,3 ', 5,5'-tetraisopropyl-4,4'-biphenol and process for producing the same
WO2023036868A1 (en) * 2021-09-10 2023-03-16 Reuter Chemische Apparatebau E.K. (het)aryl substituted bisphenol compounds and thermoplastic resins
CN118930411A (en) * 2024-10-09 2024-11-12 北京弗莱明科技有限公司 A method for producing 4,4'-biphenyl diphenol by efficient debutylation
CN118930411B (en) * 2024-10-09 2025-01-24 北京弗莱明科技有限公司 A method for producing 4,4'-biphenyl diphenol by efficient debutylation

Also Published As

Publication number Publication date
NL6410238A (en) 1965-03-04
DE1493767A1 (en) 1969-04-30

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