GB994920A - Hydroxy-alkylation process - Google Patents

Hydroxy-alkylation process

Info

Publication number
GB994920A
GB994920A GB19937/63A GB1993763A GB994920A GB 994920 A GB994920 A GB 994920A GB 19937/63 A GB19937/63 A GB 19937/63A GB 1993763 A GB1993763 A GB 1993763A GB 994920 A GB994920 A GB 994920A
Authority
GB
United Kingdom
Prior art keywords
specified
tert
aldehyde
butylphenol
reaction
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
GB19937/63A
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of GB994920A publication Critical patent/GB994920A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
    • C07C39/11—Alkylated hydroxy benzenes containing also acyclically bound hydroxy groups, e.g. saligenol
    • 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
    • C07C39/16—Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Polyethers (AREA)

Abstract

An acetal or other ether is used as a diluent in processes for the hydroxyalkylation of aromatic compounds by reacting them with an aldehyde containing 1-10 carbon atoms or with a ketone having an activated CO group, i.e. a ketone, such as trichloracetone, having a CO group which forms a hydrate. Specified aromatic compounds which may be treated are benzene, naphthalene, anthracene and pyridine and substitution products thereof containing alkyl, cycloalkyl, aryl, alkylaryl or arylalkyl radicals or hydroxy, amins, mercapto, aldehyde, carboxylic, nitro or sulphonic groups or chlorine or bromine atoms, but the process is particularly applicable to phenols having one or two hydrocarbon substituents in o-position to the hydroxy group. Specified phenols of this kind include 2-isopropylphenol, 2-tert.-butylphenol, 2,6 - diethylphenol and 2 - methyl - 6-tert.-butylphenol. Formaldehyde, used in any of its possible forms, is the preferred aldehyde, but reference is made also to the use of acetaldehyde, benzaldehyde and salicyl aldehyde. The reaction may be catalysed by an alkaline catalyst, specified catalysts being lithium, sodium, potassium and barium hydroxides, trimethyl benzyl ammonium hydroxide, and tetrahydroxy methyl phosphonium hydroxide. The reaction mixture may contain water in a proportion less than 0.5% and may also contain an alcohol, e.g. methanol or ethanol, in a proportion less than 5% by weight of the diluent. Specified acetals for use as diluents are methylol, diethyl formal and dimethyl acetal. Specified other ethers are tetrahydrofuran and dioxane. The reaction may be effected at 40-100 DEG C. under atmospheric, reduced or raised pressure. The reaction mixture, after separation of the desired product, may be circulated for use again. Examples are given in which 2,6-di-tert.-butyl-4-hydroxymethylphenol is produced from 2,6-di-tert.-butylphenol and trioxymethylene in the presence of methylol. Specification 893,896 is referred to.
GB19937/63A 1962-05-21 1963-05-20 Hydroxy-alkylation process Expired GB994920A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR898228A FR1331448A (en) 1962-05-21 1962-05-21 Hydroxyalkylation process

Publications (1)

Publication Number Publication Date
GB994920A true GB994920A (en) 1965-06-10

Family

ID=8779403

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19937/63A Expired GB994920A (en) 1962-05-21 1963-05-20 Hydroxy-alkylation process

Country Status (3)

Country Link
ES (1) ES288193A1 (en)
FR (1) FR1331448A (en)
GB (1) GB994920A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4238629A (en) * 1979-04-14 1980-12-09 Bayer Aktiengesellschaft Process for the preparation of a mixture of 2-and 4-hydroxybenzyl alcohol

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4238629A (en) * 1979-04-14 1980-12-09 Bayer Aktiengesellschaft Process for the preparation of a mixture of 2-and 4-hydroxybenzyl alcohol

Also Published As

Publication number Publication date
FR1331448A (en) 1963-07-05
ES288193A1 (en) 1963-08-01

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