GB1032885A - Preparation of polyphenylolalkanes - Google Patents

Preparation of polyphenylolalkanes

Info

Publication number
GB1032885A
GB1032885A GB303663A GB303663A GB1032885A GB 1032885 A GB1032885 A GB 1032885A GB 303663 A GB303663 A GB 303663A GB 303663 A GB303663 A GB 303663A GB 1032885 A GB1032885 A GB 1032885A
Authority
GB
United Kingdom
Prior art keywords
phenols
hexenal
phenol
specified
catalyst
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
GB303663A
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.)
Union Carbide Corp
Original Assignee
Union Carbide Corp
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 Union Carbide Corp filed Critical Union Carbide Corp
Publication of GB1032885A publication Critical patent/GB1032885A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C37/20—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 using aldehydes or ketones
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Polyphenylol alkanes are prepared by condensing a monohydric phenol with an olefinically unsaturated aldehyde using as catalyst a mixture comprising 0.01 to 50 mol per cent of a boric acid and 99.99 to 50 mol per cent of an organic acid having O linked to a C atom adjacent a COOH group, e.g. citric, salicylic, lactic, tartaric or oxalic. Specified phenols are phenol, alkyl phenols and polynuclear phenols; specified aldehydes are acrolein, methacrolein, crotonaldehyde, tigladehyde, 2-pentenal, 2-ethyl-2-hexenal, 2-methyl-2-hexenal and 2-decenal. Phenols having only one active ring position, e.g. 2,6-xylenol, yield the triphenylol derivative. Tri-, penta- and hepta-phenylol derivatives of other phenols may be obtained by using excess phenol.ALSO:Polyphenylolalkanes are prepared by condensing a monohydric phenol with an olefinically unsaturated aldehyde using as catalyst a mixture comprising (a) boric acid, and (b) an organic acid containing a <FORM:1032885/C3/1> grouping, e.g. citric, salicylic, lactic, tartaric or oxalic acid. Specified phenols are phenol, alkyl phenols and the polynuclear phenols; specified aldehydes are acrolein, methacrolein, crotonaldehyde, tiglaldehyde, 2-pentenol, 2-ethyl-2-hexenal, 2-methyl-2-hexenal, and 2-decenal. The catalyst mixture is preferably equimolar but can contain from 0.01 to 50 mol. of boron compound and 99.99 to 50 mol. of organic acid. The products may be used as intermediates in the production of polyurethane foams.
GB303663A 1962-02-15 1963-01-24 Preparation of polyphenylolalkanes Expired GB1032885A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US17333262A 1962-02-15 1962-02-15

Publications (1)

Publication Number Publication Date
GB1032885A true GB1032885A (en) 1966-06-15

Family

ID=22631549

Family Applications (1)

Application Number Title Priority Date Filing Date
GB303663A Expired GB1032885A (en) 1962-02-15 1963-01-24 Preparation of polyphenylolalkanes

Country Status (2)

Country Link
DE (1) DE1259347B (en)
GB (1) GB1032885A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2338917A1 (en) * 1976-01-24 1977-08-19 Bayer Ag (4,4')-Dihydroxy-(3,3',5,5')-tetraalkyl-diphenylmethane prodn. - from dialkyl-phenol by condensing with formaldehyde using oxalic acid catalyst

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1061791B (en) * 1953-07-16 1959-07-23 Union Carbide Corp Process for the production of low molecular weight polycondensation products

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2338917A1 (en) * 1976-01-24 1977-08-19 Bayer Ag (4,4')-Dihydroxy-(3,3',5,5')-tetraalkyl-diphenylmethane prodn. - from dialkyl-phenol by condensing with formaldehyde using oxalic acid catalyst

Also Published As

Publication number Publication date
DE1259347B (en) 1968-01-25

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