GB747841A - Manufacture of aliphatic diamines - Google Patents

Manufacture of aliphatic diamines

Info

Publication number
GB747841A
GB747841A GB31888/53A GB3188853A GB747841A GB 747841 A GB747841 A GB 747841A GB 31888/53 A GB31888/53 A GB 31888/53A GB 3188853 A GB3188853 A GB 3188853A GB 747841 A GB747841 A GB 747841A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
glycol
ruthenium
catalyst
converted
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
GB31888/53A
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 GB747841A publication Critical patent/GB747841A/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
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
    • C07C211/36—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing at least two amino groups bound to 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
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
    • C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • 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
    • C07C209/70—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 by reduction of unsaturated amines
    • 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
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/09—Diamines
    • 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
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/09—Diamines
    • C07C211/12—1,6-Diaminohexanes

Landscapes

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

Abstract

Saturated aliphatic diamines are manufactured by heating ammonia with saturated aliphatic glycols or saturated aliphatic hydroxy amines, in the presence of a metallic ruthenium catalyst and in the presence or absence of hydrogen. The ruthenium catalyst may be present in the form of the finely-divided metal, or, when hydrogen is present, in the form of a compound of ruthenium which is reducible to the metal in situ. Alternatively, the compound may be activated by treatment with hydrogen to form the metal prior to use. Preferably the catalyst is supported on a carrier such as charcoal, silica gel or alumina. The amount of ruthenium is generally from 0.5 to 10 per cent by weight of the substrate and may vary from 1 to 20 per cent of the total weight of catalyst and support. In general, a minimum of 5 equivalents of ammonia per equivalent of substrate is used with temperatures ranging from 100 DEG to 400 DEG C. and pressures of 30-1500 atmospheres. The preferred temperature range is from 150 DEG to 250 DEG C. at a pressure of from 700 to 1500 atmospheres or more if hydrogen is used and from 400 to 1000 atmospheres or more in the absence of hydrogen. Suitable starting materials include alpha, omega straight-chain alkanediols having at least 6 carbon atoms, vicinal alkanediols, such as 1,2-propylene glycol, 1,2-butylene glycol, branched-chain alkanediols, such as 3-methylhexane diol, and polyether glycols such as triethylene glycol and dipropylene glycol; hydroxyamines such as 1-amino-propanol-2, and hydroxyamine derivatives of the above glycols may also be used. Operation may be batchwise or continuous, and in vapour phase, liquid phase or heterogeneous phase. Diluents or solvents such as others, water or hydrocarbons may be added. In examples (1) to (3) hexamethylene glycol is converted to hexamethylene diamine by the action of ammonia in the presence of a ruthenium-on-charcoal catalyst with, or without, hydrogen; (4) octamethylene glycol is converted to octamethylene diamine, and (5) decamethylene glycol is converted to decamethylene diamine using conditions similar to examples (1) to (3); (6) ethanolamine is converted to a product in which ethylene diamine and piperazine are identified.
GB31888/53A 1952-12-12 1953-11-17 Manufacture of aliphatic diamines Expired GB747841A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US747841XA 1952-12-12 1952-12-12

Publications (1)

Publication Number Publication Date
GB747841A true GB747841A (en) 1956-04-18

Family

ID=22121665

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31888/53A Expired GB747841A (en) 1952-12-12 1953-11-17 Manufacture of aliphatic diamines

Country Status (1)

Country Link
GB (1) GB747841A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1170960B (en) * 1957-06-27 1964-05-27 Dow Chemical Co Continuous process for the production of diamines and polyamines
EP0169547A2 (en) * 1984-07-25 1986-01-29 Air Products And Chemicals, Inc. Selective syntheses of substituted amines
CN105622436A (en) * 2016-03-01 2016-06-01 苏州艾缇克药物化学有限公司 Preparation method of 6-amino-1-hexanol by taking calcium carbonate as catalyst

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1170960B (en) * 1957-06-27 1964-05-27 Dow Chemical Co Continuous process for the production of diamines and polyamines
EP0169547A2 (en) * 1984-07-25 1986-01-29 Air Products And Chemicals, Inc. Selective syntheses of substituted amines
EP0169547A3 (en) * 1984-07-25 1987-01-28 Air Products And Chemicals, Inc. Selective syntheses of substituted amines
CN105622436A (en) * 2016-03-01 2016-06-01 苏州艾缇克药物化学有限公司 Preparation method of 6-amino-1-hexanol by taking calcium carbonate as catalyst

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