GB936322A - Method for preparing n-alkylmorpholines - Google Patents

Method for preparing n-alkylmorpholines

Info

Publication number
GB936322A
GB936322A GB4245061A GB4245061A GB936322A GB 936322 A GB936322 A GB 936322A GB 4245061 A GB4245061 A GB 4245061A GB 4245061 A GB4245061 A GB 4245061A GB 936322 A GB936322 A GB 936322A
Authority
GB
United Kingdom
Prior art keywords
oxide
weight
morpholine
total
catalyst
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
GB4245061A
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.)
Jefferson Chemical Co Inc
Original Assignee
Jefferson Chemical Co Inc
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 Jefferson Chemical Co Inc filed Critical Jefferson Chemical Co Inc
Publication of GB936322A publication Critical patent/GB936322A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/023—Preparation; Separation; Stabilisation; Use of additives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/72—Copper
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Catalysts (AREA)

Abstract

In the preparation of N-alkyl morpholines, by reacting a morpholine with a non-tertiary alkanol in the presence of hydrogen under pressure, and a catalyst (Group IV(b), the catalyst comprises (A) a mixture of 50-90% by weight of cobalt or nickel, and 10-50% by weight of copper based on the total weight of metals, and (B) 0,5-5% by weight, based on the total, of chromium oxide, titanium oxide, thorium oxide, magnesium oxide, zinc oxide, manganese oxide, or rare earth oxides, chromium oxide being preferred. In Example I, the catalyst is prepared by calcining the coprecipitated carbonates of nickel, copper, and chromium, the resultant mixture of oxides being reduced by hydrogen.ALSO:N-alkyl morpholines are prepared by reacting a morpholine, or a C-substituted morpholine, with a non-tertiary alkanol, in the presence of hydrogen under pressure and a catalyst which comprises (A) a mixture of 50-90% by weight of cobalt or nickel and 10-50% by weight of copper based on the total weight of the metals, and (B) 0.5 to 5% by weight based on the total of chromium oxide, titanium oxide, thorium oxide, magnesium oxide, zinc oxide, manganese oxide, or rare earth oxides. The morpholine may be substituted in from 1 to 4 of the C-positions of the ring with alkyl groups containing from 1-4 carbon atoms. The proportion of non-tertiary alkanol to morpholine is from 1 to 10 moles/mole of morpholine. The non-tertiary alkanol may contain from 1 to 30 carbon atoms. The total pressure of the system is from 500-5000 p.s.i.g., which includes a partial pressure of hydrogen of 10-100 atmospheres. The reaction time is from 5 mins. to 5 hours. Examples describe the preparation of: (1) and (3) N-methylmorpholine; (2) N-ethylmorpholine; (4) 2-methyl-N-methylmorpholine; (5) N-stearylmorpholine; (6) N-cetylmorpholine; (7) N-C12-C14 alkylmorpholine; (8) N-isopropylmorpholine; and (9) N-ethyl-2,6-dimethylmorpholine. The N-alkylmorpholines may be used in the production of polyurethane foams.
GB4245061A 1960-11-28 1961-11-28 Method for preparing n-alkylmorpholines Expired GB936322A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US7187660A 1960-11-28 1960-11-28

Publications (1)

Publication Number Publication Date
GB936322A true GB936322A (en) 1963-09-11

Family

ID=22104161

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4245061A Expired GB936322A (en) 1960-11-28 1961-11-28 Method for preparing n-alkylmorpholines

Country Status (2)

Country Link
DE (1) DE1216311B (en)
GB (1) GB936322A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0017651A1 (en) * 1977-08-29 1980-10-29 The Dow Chemical Company Improved method of producing amines from alcohols, aldehydes, ketones and mixtures thereof and catalyst used
CN110713469A (en) * 2019-09-26 2020-01-21 宿州亿帆药业有限公司 Synthesis process of tridemorph
CN111675677A (en) * 2020-07-13 2020-09-18 江苏富比亚化学品有限公司 Synthesis process of N-methylmorpholine

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2543279A1 (en) * 1975-09-27 1977-04-07 Basf Ag PROCESS FOR THE PREPARATION OF N-SUBSTITUTED TETRAHYDRO-1.4-OXAZINES
DE2657476A1 (en) * 1976-12-18 1978-06-22 Basf Ag MORPHOLINE DERIVATIVES

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0017651A1 (en) * 1977-08-29 1980-10-29 The Dow Chemical Company Improved method of producing amines from alcohols, aldehydes, ketones and mixtures thereof and catalyst used
CN110713469A (en) * 2019-09-26 2020-01-21 宿州亿帆药业有限公司 Synthesis process of tridemorph
CN111675677A (en) * 2020-07-13 2020-09-18 江苏富比亚化学品有限公司 Synthesis process of N-methylmorpholine

Also Published As

Publication number Publication date
DE1216311B (en) 1966-05-12

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