GB928148A - Process for the preparation of alpha-hydroxydialdehydes - Google Patents

Process for the preparation of alpha-hydroxydialdehydes

Info

Publication number
GB928148A
GB928148A GB3672161A GB3672161A GB928148A GB 928148 A GB928148 A GB 928148A GB 3672161 A GB3672161 A GB 3672161A GB 3672161 A GB3672161 A GB 3672161A GB 928148 A GB928148 A GB 928148A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
formula
resin
hydrolysed
water
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
GB3672161A
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 GB928148A publication Critical patent/GB928148A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/20—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hydrogen atoms and substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D309/22—Radicals substituted by oxygen atoms
    • C07D309/26—Carboxaldehyde radicals
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • C07C47/19—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing hydroxy groups
    • 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
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/48—Ring-opening reactions

Landscapes

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

Abstract

a -Hydroxy-dialdehydes of the formula <FORM:0928148/IV(a)/1> where R and R1 are as defined below, are prepared by reacting an aldehyde of the formula <FORM:0928148/IV(a)/2> where R represents an unsubstituted or alkyl substituted ethylene group having both its carbon atoms in the ring and R1 represents a hydrogen atom or an alkyl group, with water in the presence of a solid cation exchange resin having functional groups in the hydrogen form and an acidity at least equal to that of an acid of pK 7. The solid cation exchange resin preferably has a porosity such that the fully water-swollen resin has a water content of at least 60% by weight, and the acidic groups are preferably sulphonic, carboxylic, phosphonic, phosphonous or iminodiacetic groups. A list of preferred aldehyde starting materials is given. The a -hydroxydialdehydes may be subsequently converted, for example by hydrogenation, to triols of the formula <FORM:0928148/IV(a)/3> where R and R1 are as defined above, In Examples: (1)-(3), acrolein dimer is hydrolysed to a -hydroxy-adipaldehyde using various types of resin and the product is hydrogenated to 1,2,6-hexanetriol; (4) methacrolein dimer is hydrolysed to 2,5-dimethyl-2-hydroxy-hexanedial. Specifications 725,161 and 789,952 are referred to.
GB3672161A 1960-10-14 1961-10-12 Process for the preparation of alpha-hydroxydialdehydes Expired GB928148A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US6252560A 1960-10-14 1960-10-14

Publications (1)

Publication Number Publication Date
GB928148A true GB928148A (en) 1963-06-06

Family

ID=22043051

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3672161A Expired GB928148A (en) 1960-10-14 1961-10-12 Process for the preparation of alpha-hydroxydialdehydes

Country Status (4)

Country Link
BE (1) BE609097A (en)
DE (1) DE1167327B (en)
GB (1) GB928148A (en)
NL (1) NL270168A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113663725A (en) * 2021-08-18 2021-11-19 山东新和成药业有限公司 Mesoporous metal organic phosphonate catalyst, preparation method thereof and application thereof in preparation of 3-hydroxypropionaldehyde

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2639297A (en) * 1946-08-30 1953-05-19 Shell Dev Preparation of 2-hydroxy-1, 6-hexanedial
US2694077A (en) * 1952-02-19 1954-11-09 Union Carbide & Carbon Corp Production of hydroxy derivatives of methacrolein dimer

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113663725A (en) * 2021-08-18 2021-11-19 山东新和成药业有限公司 Mesoporous metal organic phosphonate catalyst, preparation method thereof and application thereof in preparation of 3-hydroxypropionaldehyde
CN113663725B (en) * 2021-08-18 2024-05-10 山东新和成药业有限公司 Mesoporous metal organic phosphonate catalyst, preparation method thereof and application thereof in preparation of 3-hydroxy-propanal

Also Published As

Publication number Publication date
DE1167327B (en) 1964-04-09
NL270168A (en)
BE609097A (en)

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