GB783582A - Improvements in preparation of formamides - Google Patents

Improvements in preparation of formamides

Info

Publication number
GB783582A
GB783582A GB30484/55A GB3048455A GB783582A GB 783582 A GB783582 A GB 783582A GB 30484/55 A GB30484/55 A GB 30484/55A GB 3048455 A GB3048455 A GB 3048455A GB 783582 A GB783582 A GB 783582A
Authority
GB
United Kingdom
Prior art keywords
group
choline
primary
methyl
hydroxyethyl
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
GB30484/55A
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.)
Rohm and Haas Co
Original Assignee
Rohm and Haas 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 Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB783582A publication Critical patent/GB783582A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
    • 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
    • B01J31/0201—Oxygen-containing compounds
    • B01J31/0202—Alcohols or phenols
    • 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
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0239—Quaternary ammonium compounds
    • 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
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0271—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds also containing elements or functional groups covered by B01J31/0201 - B01J31/0231
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered

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

Formamides are prepared by reacting a nontertiary amine with carbon monoxide under a pressure of from 500 to 5000 lbs. per square inch and in the presence of an alkanol having from 1 to 4 carbon atoms and a catalyst having the formula <FORM:0783582/IV (a)/1> in which R is hydrogen, or a methyl, ethyl, propyl or butyl group and R1 is a methyl or hydroxy ethyl group. The reaction may be carried out at a temperature of between 0 DEG and 75 DEG C., preferably between 25 DEG and 50 DEG C. Specified catalysts are choline, choline methoxide, choline ethoxide, choline propoxide, choline butoxide, tetramethylammonium hydroxide and (C1-C4) alkoxides thereof. The amine reactant may be a primary alkylamine having a (C1-C8) alkyl group, a primary alkenylamine having a (C3-C18) alkenyl group, a (C7-C10) primary arylalkylamine, a primary alkanolamine having a (C2-C18) alkanol group, a secondary dialkylamine having (C1-C2) alkyl groups, a (C14-C20) secondary diarylalkylamine, a (C8-C9) secondary arylalkylalkanolamine, a (C3-C4) secondary alkylalkanolamine, a secondary heterocyclic amine having a heterocyclic group of five to six members including the amino nitrogen, a primary or secondary alkylenediamine having a (C2-C18) alkylene group, or a secondary dialkyldiamine having a (C1-C2) alkyl group on each of the nitrogen atoms and a (C2-C12) alkylene group connecting the nitrogen atoms. A list of suitable amine reactants is specified, methylamine, dimethylamine, allylamine, benzylamine and piperidine being preferred. The examples describe the preparation of N-formylpiperidine, N-formylmorpholine, N-formylethylenediamine, N : N1 - diformylethylenediamine, N : N1 - diformyldiamino-octadecane, N : N1-diformylhexamethylenediamine, N - formyl - N : N1 - dimethyldiaminoethane, N : N1 - diformyl - N : N1 - dimethyldiaminoethane, N-methyl-, N-ethyl-, N-butyl-, N-octadecyl-, N-allyl-, N-octenyl-, N-octadecenyl-, N-cyclohexyl-, N-cycloheptenyl-, N-benzyl-, N-phenylbutyl-, N-hydroxyethyl-, N-hydroxydecyl-, N-hydroxyoctadecyl-, N : N-dimethyl-, N : N-diethyl-, N : N-dibenzyl-, N : N-di-(butylbenzyl)-, N - methyl - N - hydroxyethyl- and N-benzyl-N-hydroxyethyl-formamides.
GB30484/55A 1954-11-09 1955-10-25 Improvements in preparation of formamides Expired GB783582A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US783582XA 1954-11-09 1954-11-09

Publications (1)

Publication Number Publication Date
GB783582A true GB783582A (en) 1957-09-25

Family

ID=22143528

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30484/55A Expired GB783582A (en) 1954-11-09 1955-10-25 Improvements in preparation of formamides

Country Status (1)

Country Link
GB (1) GB783582A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2973371A1 (en) * 2011-04-04 2012-10-05 Commissariat Energie Atomique Preparing a formamide compound, comprises reacting an amine compound with carbon dioxide in the presence of a catalyst and silane compound
FR2975395A1 (en) * 2011-05-16 2012-11-23 Commissariat Energie Atomique Preparing formamide compound, comprises reacting amine compound with carbon dioxide in the presence of a catalyst and a silane compound
WO2012137152A3 (en) * 2011-04-04 2012-12-27 Commissariat A L'energie Atomique Et Aux Energies Alternatives Method for preparing formamide compounds
CN112321537A (en) * 2020-11-03 2021-02-05 西南化工研究设计院有限公司 Method for synthesizing formylmorpholine through heterogeneous reaction

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2973371A1 (en) * 2011-04-04 2012-10-05 Commissariat Energie Atomique Preparing a formamide compound, comprises reacting an amine compound with carbon dioxide in the presence of a catalyst and silane compound
WO2012137152A3 (en) * 2011-04-04 2012-12-27 Commissariat A L'energie Atomique Et Aux Energies Alternatives Method for preparing formamide compounds
US8877971B2 (en) 2011-04-04 2014-11-04 Commissariat A L'energie Atomique Et Aux Energies Alternatives Method for preparing formamide compounds
FR2975395A1 (en) * 2011-05-16 2012-11-23 Commissariat Energie Atomique Preparing formamide compound, comprises reacting amine compound with carbon dioxide in the presence of a catalyst and a silane compound
CN112321537A (en) * 2020-11-03 2021-02-05 西南化工研究设计院有限公司 Method for synthesizing formylmorpholine through heterogeneous reaction

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