GB598298A - Improvements in or relating to production of n,n-dialkylamino alcohols - Google Patents

Improvements in or relating to production of n,n-dialkylamino alcohols

Info

Publication number
GB598298A
GB598298A GB16696/44A GB1669644A GB598298A GB 598298 A GB598298 A GB 598298A GB 16696/44 A GB16696/44 A GB 16696/44A GB 1669644 A GB1669644 A GB 1669644A GB 598298 A GB598298 A GB 598298A
Authority
GB
United Kingdom
Prior art keywords
amino
catalyst
pentanediol
pentanol
diethylamino
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
GB16696/44A
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 GB598298A publication Critical patent/GB598298A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
    • C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton

Landscapes

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

Abstract

An N,N-dialkylamino alcohol is produced by reacting a non-halogenated aliphatic polyhydric alcohol having at least one primary and at least one secondary carbinol radical with a secondary aliphatic amine in the presence of a metal oxide-containing or metal hydrogenation catalyst at a temperature of at least 120 DEG C. Reaction may be effected in liquid phase at 120-180 DEG C., but temperatures up to, for example, 250 DEG C. may be used. 1,4-Pentanediol and diethylamine yield N,N-diethyl-1-amino-4-pentanol which, with ammonia or thionyl chloride respectively gives 5-diethylamino-2-amino (or chlor) -pentane which are intermediates for the production of antimalarials. Other polyhydric alcohols used include propylene glycol, 1,2- or 1,3-butanediol, and 1,3-or 1,4-pentanediol and other secondary amines are di-methyl, -ethyl-n-propyl, -isopropyl and -butyl amines. Hydrogenation catalysts include Ni, Pt, Pd, Co and Cu, copper oxide, platinum oxide and hydrated alumina which may be on carriers. In examples, 1,4-pentanediol, diethylamine and a catalyst made by decomposition of nickel formate in mineral oil, which catalyst may first be washed with ethanol, are autoclaved while stirring at temperatures between 150 DEG and 180 DEG C., and the N,N-diethyl-1-amino-4-pentanol fraction recovered. This may be converted to 5-diethylamino-2-amino-pentane by autoclaving with anhydrous ammonia and a nickel catalyst at 200 DEG C.
GB16696/44A 1942-10-29 1944-09-01 Improvements in or relating to production of n,n-dialkylamino alcohols Expired GB598298A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US598298XA 1942-10-29 1942-10-29

Publications (1)

Publication Number Publication Date
GB598298A true GB598298A (en) 1948-02-16

Family

ID=22025545

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16696/44A Expired GB598298A (en) 1942-10-29 1944-09-01 Improvements in or relating to production of n,n-dialkylamino alcohols

Country Status (1)

Country Link
GB (1) GB598298A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4223138A (en) * 1977-04-16 1980-09-16 Bayer Aktiengesellschaft Process for the selective preparation of monohydroxyalkylated amines
CN110616236A (en) * 2019-10-14 2019-12-27 暨明医药科技（苏州）有限公司 Preparation method of (R) -N1, N1-diethyl-1, 4-pentanediamine
CN114713224A (en) * 2022-04-02 2022-07-08 厦门大学 Catalyst for preparing ethylamine by catalyzing ethanol amination and preparation method and application thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4223138A (en) * 1977-04-16 1980-09-16 Bayer Aktiengesellschaft Process for the selective preparation of monohydroxyalkylated amines
CN110616236A (en) * 2019-10-14 2019-12-27 暨明医药科技（苏州）有限公司 Preparation method of (R) -N1, N1-diethyl-1, 4-pentanediamine
CN114713224A (en) * 2022-04-02 2022-07-08 厦门大学 Catalyst for preparing ethylamine by catalyzing ethanol amination and preparation method and application thereof

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