GB842209A - Preparation of bis(hydroxyphenyl)alkyl-methanes - Google Patents

Preparation of bis(hydroxyphenyl)alkyl-methanes

Info

Publication number
GB842209A
GB842209A GB2449/57A GB244957A GB842209A GB 842209 A GB842209 A GB 842209A GB 2449/57 A GB2449/57 A GB 2449/57A GB 244957 A GB244957 A GB 244957A GB 842209 A GB842209 A GB 842209A
Authority
GB
United Kingdom
Prior art keywords
hydroxyphenyl
bis
methanes
alkyl
isoheptyl
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
GB2449/57A
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.)
ExxonMobil Technology and Engineering Co
Original Assignee
Exxon Research and Engineering Co
Esso Research and Engineering 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 Exxon Research and Engineering Co, Esso Research and Engineering Co filed Critical Exxon Research and Engineering Co
Publication of GB842209A publication Critical patent/GB842209A/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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
    • B01J31/08—Ion-exchange resins
    • B01J31/10—Ion-exchange resins sulfonated
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
    • B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
    • B01J2231/347—1,2-additions, e.g. aldol or Knoevenagel condensations via cationic intermediates, e.g. bisphenol A type processes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Bis(hydroxyphenyl)-alkyl-methanes are prepared by mixing one mole of an aldehyde containing 4 to 13 carbon atoms with at least two moles of a phenol, maintaining the mixture in liquid phase at reaction temperature in the presence of a solid acid-reacting cation-exchange organic material while removing water from the reaction mixture, mechanically separating the solid cation exchange material from the liquid reaction mixture and recovering the bis(hydroxyphenyl)-alkyl-methane. Specified cation exchange materials include the sulphonated phenolformaldehyde and polystyrene type resins. Specified bisphenols obtainable by the process include 1:1-bis(4-hydroxyphenyl)- or (2-hydroxy-5-chlorophenyl)-butane, 1:1-bis(4-hydroxyphenyl)-hexane, 1:4 bis(2-hydroxyphenyl-5-isopropylphenyl)-isooctane and bis (4-hydroxyphenyl)-isododecy-lmethane. In examples phenol is reacted, in toluene or toluene and benzene and in the presence of a sulphonated styrene-divinyl benzene copolymer, with a C8 Oxo aldehyde, a decanal, isovaleraldehyde or n-hexaldehyde to give bis (4-hydroxyphenyl)-isoheptyl-,-isononyl-, isobutyland-n-amyl-methanes. The preparation of the isoheptyl compound using boron trifluoride as catalyst is described for comparison.
GB2449/57A 1956-02-03 1957-01-23 Preparation of bis(hydroxyphenyl)alkyl-methanes Expired GB842209A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US842209XA 1956-02-03 1956-02-03

Publications (1)

Publication Number Publication Date
GB842209A true GB842209A (en) 1960-07-20

Family

ID=22183574

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2449/57A Expired GB842209A (en) 1956-02-03 1957-01-23 Preparation of bis(hydroxyphenyl)alkyl-methanes

Country Status (1)

Country Link
GB (1) GB842209A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3221061A (en) * 1961-08-01 1965-11-30 Union Carbide Corp Process for the production of 2,2-bis-(4-hydroxyphenyl) propane
EP0023325A1 (en) * 1979-07-31 1981-02-04 Bayer Ag Catalyst for the preparation of bisphenols
EP0112530A2 (en) * 1982-12-27 1984-07-04 General Electric Company Polycarbonate compositions
US5302774A (en) * 1992-08-20 1994-04-12 Bayer Aktiengesellschaft Process for the production of bisphenols
DE102009023551A1 (en) 2009-05-30 2010-12-02 Bayer Materialscience Ag Regeneration of acidic ion exchangers

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3221061A (en) * 1961-08-01 1965-11-30 Union Carbide Corp Process for the production of 2,2-bis-(4-hydroxyphenyl) propane
EP0023325A1 (en) * 1979-07-31 1981-02-04 Bayer Ag Catalyst for the preparation of bisphenols
EP0112530A2 (en) * 1982-12-27 1984-07-04 General Electric Company Polycarbonate compositions
EP0112530A3 (en) * 1982-12-27 1986-10-08 General Electric Company Polycarbonate compositions
US5302774A (en) * 1992-08-20 1994-04-12 Bayer Aktiengesellschaft Process for the production of bisphenols
DE102009023551A1 (en) 2009-05-30 2010-12-02 Bayer Materialscience Ag Regeneration of acidic ion exchangers
EP2263794A1 (en) 2009-05-30 2010-12-22 Bayer MaterialScience AG Regeneration of acid ion exchangers
US8410184B2 (en) 2009-05-30 2013-04-02 Bayer Materialscience Ag Regeneration of acidic ion exchangers

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