GB1017618A - Process for the preparation of hydroxyaldehydes and derivatives thereof - Google Patents

Process for the preparation of hydroxyaldehydes and derivatives thereof

Info

Publication number
GB1017618A
GB1017618A GB18935/64A GB1893564A GB1017618A GB 1017618 A GB1017618 A GB 1017618A GB 18935/64 A GB18935/64 A GB 18935/64A GB 1893564 A GB1893564 A GB 1893564A GB 1017618 A GB1017618 A GB 1017618A
Authority
GB
United Kingdom
Prior art keywords
aldehyde
give
reaction
paraformaldehyde
hydroxypivalic
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
GB18935/64A
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.)
Snam SpA
Original Assignee
Snam SpA
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 Snam SpA filed Critical Snam SpA
Publication of GB1017618A publication Critical patent/GB1017618A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/75—Reactions with formaldehyde
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
    • C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
    • 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)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A b -hydroxy-aldehyde is prepared by reacting, under anhydrous conditions, formaldehyde in a polymeric form with an aliphatic aldehyde having at least one hydrogen atom attached to the a -carbon atom in the presence of an alkaline catalyst. The preferred catalysts are the alcoholates, carbonates, bicarbonates or organic salts of alkali or alkaline earth metals, a mono-, di- or tri-substituted aliphatic amine or an aromatic or quaternary ammonium base. The process is particularly applicable to the reaction between trioxymethylene and iso-butyraldehyde to give hydroxypivalic aldehyde along with some 2,2-dimethylpropane-1,3-diol and its monoisobutyric and mono-hydroxypivalic esters as by-products. The hydroxyaldehydes may be oxidized to the corresponding hydroxy acids, for example, using oxygen and an oxidation catalyst such as Ag/Cu in basic solution. Glycols may also be made by hydrogenation of the hydroxy aldehydes. Examples are given of (a) the reaction between paraformaldehyde and isobutyraldehyde to give hydroxypivalic aldehyde which is catalytically hydrogenated to give neopentyl glycol; (b) the reaction between paraformaldehyde and iso valerylaldehyde to give 2-isopropyl-hydracrylic aldehyde and (c) the reaction between paraformaldehyde and 2-methylbutyric aldehyde to give 2-methyl-2-ethyl - 3 - hydroxypropionic aldehyde.
GB18935/64A 1963-05-07 1964-05-06 Process for the preparation of hydroxyaldehydes and derivatives thereof Expired GB1017618A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT956963 1963-05-07

Publications (1)

Publication Number Publication Date
GB1017618A true GB1017618A (en) 1966-01-19

Family

ID=11132306

Family Applications (1)

Application Number Title Priority Date Filing Date
GB18935/64A Expired GB1017618A (en) 1963-05-07 1964-05-06 Process for the preparation of hydroxyaldehydes and derivatives thereof

Country Status (3)

Country Link
BE (1) BE647588A (en)
GB (1) GB1017618A (en)
NL (1) NL6405068A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1793512A1 (en) * 1968-09-27 1972-02-10 Basf Ag Process for the preparation of 2,2-dimethyl-3-hydroxypropanal
JPS511686B1 (en) * 1969-11-15 1976-01-20
FR2383908A1 (en) * 1977-03-16 1978-10-13 Basf Ag PROCESS FOR PREPARATION OF VINYLLACTIC ACID AND ITS ESTERS
US5144088A (en) * 1991-04-26 1992-09-01 Aristech Chemical Corporation Manufacture of neopentyl glycol (I)
US5146012A (en) * 1991-04-26 1992-09-08 Aristech Chemical Corporation Manufacture of neopentyl glycol (III)
WO1992022521A1 (en) * 1991-06-17 1992-12-23 Aristech Chemical Corporation Manufacture of neopentyl glycol (iia)
US5185478A (en) * 1991-06-17 1993-02-09 Aristech Chemical Corporation Manufacture of neopentyl glycol (IIA)
US5532417A (en) * 1991-04-26 1996-07-02 Aristech Chemical Corporation Manufacture of neopentyl glycol (IV)
WO1997016401A1 (en) * 1995-11-03 1997-05-09 Union Carbide Chemicals & Plastics Technology Corporation Reaction mixtures containing substituted hydrocarbon diols and processes for the preparation thereof
CN114728870A (en) * 2019-11-07 2022-07-08 伊士曼化工公司 Recovery of the constituent oxo diols

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4855515A (en) * 1987-08-12 1989-08-08 Eastman Kodak Company Process for the production of neopentyl glycol
CA2072485C (en) * 1991-06-28 2002-11-19 Jeffrey S. Salek Manufacture of neopentyl glycol (iv)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1793512A1 (en) * 1968-09-27 1972-02-10 Basf Ag Process for the preparation of 2,2-dimethyl-3-hydroxypropanal
JPS511686B1 (en) * 1969-11-15 1976-01-20
FR2383908A1 (en) * 1977-03-16 1978-10-13 Basf Ag PROCESS FOR PREPARATION OF VINYLLACTIC ACID AND ITS ESTERS
US5144088A (en) * 1991-04-26 1992-09-01 Aristech Chemical Corporation Manufacture of neopentyl glycol (I)
US5146012A (en) * 1991-04-26 1992-09-08 Aristech Chemical Corporation Manufacture of neopentyl glycol (III)
US5532417A (en) * 1991-04-26 1996-07-02 Aristech Chemical Corporation Manufacture of neopentyl glycol (IV)
WO1992022521A1 (en) * 1991-06-17 1992-12-23 Aristech Chemical Corporation Manufacture of neopentyl glycol (iia)
US5185478A (en) * 1991-06-17 1993-02-09 Aristech Chemical Corporation Manufacture of neopentyl glycol (IIA)
WO1997016401A1 (en) * 1995-11-03 1997-05-09 Union Carbide Chemicals & Plastics Technology Corporation Reaction mixtures containing substituted hydrocarbon diols and processes for the preparation thereof
CN114728870A (en) * 2019-11-07 2022-07-08 伊士曼化工公司 Recovery of the constituent oxo diols

Also Published As

Publication number Publication date
NL6405068A (en) 1964-11-09
BE647588A (en) 1964-11-06

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