GB709441A - Preparation of hexamethylenediamines - Google Patents

Preparation of hexamethylenediamines

Info

Publication number
GB709441A
GB709441A GB16073/51A GB1607351A GB709441A GB 709441 A GB709441 A GB 709441A GB 16073/51 A GB16073/51 A GB 16073/51A GB 1607351 A GB1607351 A GB 1607351A GB 709441 A GB709441 A GB 709441A
Authority
GB
United Kingdom
Prior art keywords
adipaldehyde
hydrogen
prepared
ammonia
methanol
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
GB16073/51A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and 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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB709441A publication Critical patent/GB709441A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
    • 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
    • C07C209/68—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

Landscapes

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

Abstract

Hexamethylenediamines are prepared by reacting adipaldehyde in a liquid reaction medium with a compound of formula <FORM:0709441/IV (b)/1> in which R and R1 are hydrogen or monovalent hydrocarbon radicals, present in a proportion of from 2 to 9.9 mols. per mol. of adipaldehyde, and hydrogen at temperatures in the range 25-150 DEG C. in the presence of a hydrogenation catalyst. The adipaldehyde may be prepared by the process of Specification 709,450. Suitable liquids for the reaction medium are methanol, ethanol, isopropanol, tertiary amyl alcohol, benzene and dioxane. Suitable catalysts are nickel, cobalt, iron, palladium and ruthenium and they may be supported, for example, on carbon, silica or alumina. Suitable nitrogen compounds are, for example, ammonia, methylamine, ethylamine, butylamine, dodecylamine, dimethylamine, methylethylamine, aniline, N-methylaniline, cyclohexylamine and dicyclohexylamine. In the examples adipaldehyde prepared as a solution in methanol is reacted with ammonia and hydrogen in the presence of nickel to give hexamethylenediamine, which may be isolated as the picrate.
GB16073/51A 1950-10-09 1951-07-06 Preparation of hexamethylenediamines Expired GB709441A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US709441XA 1950-10-09 1950-10-09

Publications (1)

Publication Number Publication Date
GB709441A true GB709441A (en) 1954-05-26

Family

ID=22098295

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16073/51A Expired GB709441A (en) 1950-10-09 1951-07-06 Preparation of hexamethylenediamines

Country Status (1)

Country Link
GB (1) GB709441A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111072489A (en) * 2019-12-16 2020-04-28 中国科学院大连化学物理研究所 Method for preparing hexamethylene diamine from hexamethylene dialdehyde in fixed bed reactor
CN111072488A (en) * 2019-12-16 2020-04-28 中国科学院大连化学物理研究所 Preparation process of hexamethylene diamine based on cyclohexene
CN111138257A (en) * 2019-12-16 2020-05-12 中国科学院大连化学物理研究所 Method for preparing hexanedial
CN111138295A (en) * 2019-12-16 2020-05-12 中国科学院大连化学物理研究所 Preparation process of hexamethylene diamine based on cyclohexene
CN111138255A (en) * 2019-12-16 2020-05-12 中国科学院大连化学物理研究所 Process for preparing hexanedial from cyclohexene
CN111138256B (en) * 2019-12-16 2021-07-13 中国科学院大连化学物理研究所 Preparation method of hexanediol

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111072489A (en) * 2019-12-16 2020-04-28 中国科学院大连化学物理研究所 Method for preparing hexamethylene diamine from hexamethylene dialdehyde in fixed bed reactor
CN111072488A (en) * 2019-12-16 2020-04-28 中国科学院大连化学物理研究所 Preparation process of hexamethylene diamine based on cyclohexene
CN111138257A (en) * 2019-12-16 2020-05-12 中国科学院大连化学物理研究所 Method for preparing hexanedial
CN111138295A (en) * 2019-12-16 2020-05-12 中国科学院大连化学物理研究所 Preparation process of hexamethylene diamine based on cyclohexene
CN111138255A (en) * 2019-12-16 2020-05-12 中国科学院大连化学物理研究所 Process for preparing hexanedial from cyclohexene
CN111072489B (en) * 2019-12-16 2021-05-25 中国科学院大连化学物理研究所 Method for preparing hexamethylene diamine from hexamethylene dialdehyde in fixed bed reactor
CN111138256B (en) * 2019-12-16 2021-07-13 中国科学院大连化学物理研究所 Preparation method of hexanediol

Similar Documents

Publication Publication Date Title
GB835717A (en) Preparation of substituted morpholines
GB709441A (en) Preparation of hexamethylenediamines
EP0009976A1 (en) Process for the production of amorphous aluminosilicates and their use as catalysts
CN109053460B (en) Method for catalyzing amination of benzyl alcohol compound
KR880007511A (en) Thienylethylamine, dithienylethylamine, and preparation method thereof
US2532277A (en) 1, 6 hexanediamine derivatives
US3448153A (en) Method for the preparation of 2-amino-1-alkanols
US6245932B1 (en) Cyanoethylation of cycloaliphatic vicinal primary diamines
CA1037496A (en) Synthesis of bis (2-(n-dimethylamino)ethyl) ether
US3398196A (en) Nu-secondary-alkyl trimethylene diamines
ES427156A1 (en) Alkylation of aromatic amines
US4105657A (en) Production of n-alkyl derivatives of cyclic alkylenimines
US3361818A (en) Process for preparing aminated benzenes from aminated cyclohexanes
GB1080807A (en) Heterocyclic amino-isobutyl compounds
US2765306A (en) 2-dialkylaminomethyl-5-methyl-1, 6 hexane diamines and related compounds
US4046810A (en) Process for the preparation of diphenylamine and derivatives thereof
US3641022A (en) Liquid phase process for the production of n-alkyl morpholines
JPS62249947A (en) Cyclodialkylation of amine and amide
US3340259A (en) Process for making bis diamino alkynes
US3290377A (en) Catalytic reduction of nitro compounds to amines
Zaugg et al. 2, 2-Diphenyl-1, 3-propanediamines and N-substituted derivatives
ES251786A1 (en) N-(ortho-methoxyphenoxy-ethyl)-n-propylamine
US3824252A (en) Process for preparing indole
US2515872A (en) Preparation of secondary and tertiary aromatic amines
US2885439A (en) Preparation of substituted amines