GB1177557A - Arylamines - Google Patents

Arylamines

Info

Publication number
GB1177557A
GB1177557A GB57526/67A GB5752667A GB1177557A GB 1177557 A GB1177557 A GB 1177557A GB 57526/67 A GB57526/67 A GB 57526/67A GB 5752667 A GB5752667 A GB 5752667A GB 1177557 A GB1177557 A GB 1177557A
Authority
GB
United Kingdom
Prior art keywords
catalyst
amine
pka
molar ratio
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
GB57526/67A
Inventor
Irvin Bruce Van Horn
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.)
Bayer Corp
Original Assignee
Mobay Corp
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 Mobay Corp filed Critical Mobay Corp
Publication of GB1177557A publication Critical patent/GB1177557A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
    • C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
    • C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
    • 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
    • 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
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups

Landscapes

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

Abstract

1,177,557. Arylamines. MOBAY CHEMICAL CO. 19 Dec., 1967 [19 Dec., 1966], No. 57526/67. Heading C2C. Substituted arylamines are prepared by reacting an arylamine with formaldehyde with vigorous agitation in the presence of a catalyst at a molar ratio of amine to catalyst of from 1 to greater than 20, the catalyst being an acid or a salt which hydrolyses to give an acid and having a pka of from less than 1 to greater than 3À5 at a temperature of from 50-110‹ C. for a period of from 0À01 minute to 2 hours, wherein the reaction is carried out at a temperature of 65-95‹ C. for 0À01 to 5 minutes when the molar ratio of amine to catalyst is 1-20 and the pka of the catalyst is less than 3À5; the reaction is carried out at 90-110‹ C. for 2-15 minutes when the molar ratio of amine to catalyst is 1-20 and the pka of the catalyst is 3À5 or greater; the reaction is carried out at 50-90‹ C. for 1-15 minutes when the molar ratio of amine to catalyst is greater than 20 and the pka of the catalyst is less than 1; and the reaction is carried out at 90-110‹ C. for 10 mins.-2 hours when the molar ratio of amine to catalyst is greater than 20 and the pka of the catalyst is 1 or greater. The amines used as starting materials may be substituted by, for example, halogen, ether groups, or nitro groups. Long lists of suitable catalysts and starting amines are given. An example is given of the conversion of aniline to a mixture of N-(o-aminobenzyl) aniline and N-(p-aminobenzyl) amine.
GB57526/67A 1966-12-19 1967-12-19 Arylamines Expired GB1177557A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US60254966A 1966-12-19 1966-12-19

Publications (1)

Publication Number Publication Date
GB1177557A true GB1177557A (en) 1970-01-14

Family

ID=24411792

Family Applications (1)

Application Number Title Priority Date Filing Date
GB57526/67A Expired GB1177557A (en) 1966-12-19 1967-12-19 Arylamines

Country Status (5)

Country Link
BE (1) BE708233A (en)
DE (1) DE1643471A1 (en)
FR (1) FR1549767A (en)
GB (1) GB1177557A (en)
NL (1) NL6717326A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4172948A (en) 1979-01-24 1979-10-30 Atlantic Richfield Company Preparation of diphenylmethane mono and dicarbamates and polymethylene polyphenyl carbamates

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4039580A (en) * 1975-07-24 1977-08-02 The Upjohn Company Process for preparing di(aminophenyl)methanes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4172948A (en) 1979-01-24 1979-10-30 Atlantic Richfield Company Preparation of diphenylmethane mono and dicarbamates and polymethylene polyphenyl carbamates

Also Published As

Publication number Publication date
FR1549767A (en) 1968-12-13
BE708233A (en) 1968-05-02
NL6717326A (en) 1968-06-20
DE1643471A1 (en) 1971-03-11

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