GB753741A - Process for the production of organic isocyanates - Google Patents

Process for the production of organic isocyanates

Info

Publication number
GB753741A
GB753741A GB6069/54A GB606954A GB753741A GB 753741 A GB753741 A GB 753741A GB 6069/54 A GB6069/54 A GB 6069/54A GB 606954 A GB606954 A GB 606954A GB 753741 A GB753741 A GB 753741A
Authority
GB
United Kingdom
Prior art keywords
halide
reaction
boron trifluoride
primary amine
benzene
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
GB6069/54A
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.)
Monsanto Chemicals Ltd
Monsanto Chemical Co
Original Assignee
Monsanto Chemicals Ltd
Monsanto Chemical 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 Monsanto Chemicals Ltd, Monsanto Chemical Co filed Critical Monsanto Chemicals Ltd
Publication of GB753741A publication Critical patent/GB753741A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C263/00—Preparation of derivatives of isocyanic acid
    • C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C07C209/78—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton from carbonyl compounds, e.g. from formaldehyde, and amines having amino groups bound to carbon atoms of six-membered aromatic rings, with formation of methylene-diarylamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
    • C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C265/00—Derivatives of isocyanic acid
    • C07C265/14—Derivatives of isocyanic acid containing at least two isocyanate groups bound to the same carbon skeleton

Landscapes

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

Abstract

Organic isocyanates are prepared by the reaction between a carbonyl halide and a primary organic monoamine or polyamine and/or carbamyl halide in the presence of boron trifluoride or a complex thereof yielding boron trifluoride under the reaction conditions without generating a compound with which the isocyanate reacts. The process is applicable to the preparation of alkyl-, cycloalkyl-, aralkyl-, aryl-, alkaryl- and hydroaryl mono- and polyisocyanates. From 0.5 to 3 per cent of boron trifluoride is preferably employed, based upon the weight of the primary amine, and this may be added in the form of a complex with diethyl ether, acetone, pyridine, dimethylaniline, ethyl acetate or anisole. The reaction is preferably conducted at 70-120 DEG C. in an inert organic liquid, preferably one boiling below 200 DEG C at atmospheric pressure, e.g. benzene, toluene, xylene, cymene, cyclohexane, monochloro-, dichloro- and amyl-benzene, carbon tetrachloride, tetrachloroethane, trichloro- and tetrachloroethylene. The primary amine hydrohalide and/or carbamyl halide is preferably produced in situ by treating a solution or slurry of the corresponding primary amine in an organic liquid with phosgene, carbonyl bromide or a halogen halide. After subsequent conversion to isocyanate the reaction mixture may be degassed and/or fractionally distilled. The examples describe the preparation of p:p1-diisocyanatodiphenylmethane.
GB6069/54A 1953-03-02 1954-03-02 Process for the production of organic isocyanates Expired GB753741A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US753741XA 1953-03-02 1953-03-02

Publications (1)

Publication Number Publication Date
GB753741A true GB753741A (en) 1956-08-01

Family

ID=22125290

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6069/54A Expired GB753741A (en) 1953-03-02 1954-03-02 Process for the production of organic isocyanates

Country Status (1)

Country Link
GB (1) GB753741A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2344350A1 (en) * 1976-03-19 1977-10-14 Redicon Corp DEEP STAMPING TOOLS
FR2374105A1 (en) * 1976-12-14 1978-07-13 Redicon Corp DUAL ACTION CONTAINER FORMING PRESS

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2344350A1 (en) * 1976-03-19 1977-10-14 Redicon Corp DEEP STAMPING TOOLS
FR2374105A1 (en) * 1976-12-14 1978-07-13 Redicon Corp DUAL ACTION CONTAINER FORMING PRESS

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