EP0695299A1 - Procede de preparation d'oxazolines et d'oxazines par lots - Google Patents

Procede de preparation d'oxazolines et d'oxazines par lots

Info

Publication number
EP0695299A1
EP0695299A1 EP94914379A EP94914379A EP0695299A1 EP 0695299 A1 EP0695299 A1 EP 0695299A1 EP 94914379 A EP94914379 A EP 94914379A EP 94914379 A EP94914379 A EP 94914379A EP 0695299 A1 EP0695299 A1 EP 0695299A1
Authority
EP
European Patent Office
Prior art keywords
reaction
propanolamides
ethanolamides
oxazines
oxazolines
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.)
Withdrawn
Application number
EP94914379A
Other languages
German (de)
English (en)
Inventor
Wilhelm Barlage
Michael Beck
Wolfgang Ritter
Herbert Fischer
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0695299A1 publication Critical patent/EP0695299A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0201—Oxygen-containing compounds
    • B01J31/0211—Oxygen-containing compounds with a metal-oxygen link
    • B01J31/0212—Alkoxylates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/12—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals containing only hydrogen and carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
    • C07D265/08—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C08G73/0233—Polyamines derived from (poly)oxazolines, (poly)oxazines or having pendant acyl groups

Definitions

  • FIG. 1 A possible process sequence of the method according to the invention is shown in the attached FIG. 1.
  • the first reaction stage about 1.5 mol of alkanolamine are reacted with 1 mol of fatty acid methyl ester at a temperature of 130 to 180 ° C. to form the carboxylic acid alkanolamide.
  • the methanol formed distills off at this reaction temperature.
  • the excess alkanolamine is distilled off by slowly lowering the pressure (to at least 30 mbar) at an internal temperature of 140 to 160 ° C.
  • oxazoline or oxazine are obtained in yields of approx. 75% and obtained with a purity of approx. 95%.
  • the unreacted starting materials or by-products can be used again for subsequent batches, so that a total yield of> 90% can be achieved.

Landscapes

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

Abstract

L'invention concerne un procédé de préparation d'oxazines et d'oxazolines, selon lequel des 3-propanolamides ou des éthanolamides d'acides carboxyliques sont condensés éventuellement en présence d'un catalyseur, à des températures très élevées et à une pression réduite. Ce procédé se caractérise en ce que pendant la réaction, un courant d'azote plus lent est acheminé à travers la cuve de réaction pour expulser l'eau qui s'est formée au cours de la réaction. Les oxazolines et les oxazines formées sont extraites par distillation directement par l'intermédiaire d'un vaporisateur à couche mince.
EP94914379A 1993-04-24 1994-04-15 Procede de preparation d'oxazolines et d'oxazines par lots Withdrawn EP0695299A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19934313511 DE4313511A1 (de) 1993-04-24 1993-04-24 Verfahren zur Herstellung von Oxazolinen und Oxazinen im Batch-Verfahren
DE4313511 1993-04-24
PCT/EP1994/001173 WO1994025447A1 (fr) 1993-04-24 1994-04-15 Procede de preparation d'oxazolines et d'oxazines par lots

Publications (1)

Publication Number Publication Date
EP0695299A1 true EP0695299A1 (fr) 1996-02-07

Family

ID=6486315

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94914379A Withdrawn EP0695299A1 (fr) 1993-04-24 1994-04-15 Procede de preparation d'oxazolines et d'oxazines par lots

Country Status (4)

Country Link
EP (1) EP0695299A1 (fr)
JP (1) JPH08508724A (fr)
DE (1) DE4313511A1 (fr)
WO (1) WO1994025447A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3824982A1 (de) * 1987-11-10 1989-05-18 Henkel Kgaa 2-(11-hydroxy-8-heptadecenyl- oder 11,8- bzw. 11,9-heptadecadienyl)oxazolin, sowie verfahren zur herstellung gegebenenfalls substituierter hoeherer 2-(alkyl- bzw. alkenyl)-oxazoline

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3824982A1 (de) * 1987-11-10 1989-05-18 Henkel Kgaa 2-(11-hydroxy-8-heptadecenyl- oder 11,8- bzw. 11,9-heptadecadienyl)oxazolin, sowie verfahren zur herstellung gegebenenfalls substituierter hoeherer 2-(alkyl- bzw. alkenyl)-oxazoline
DE3914159A1 (de) * 1989-04-28 1990-10-31 Henkel Kgaa Verfahren zur herstellung von 2-alkyl- bzw. alkenyl-2-oxazolinen aus fettsaeureglyceriden
DE3914155A1 (de) * 1989-04-28 1990-10-31 Henkel Kgaa Verfahren zur herstellung von 5,6-dihydro-4h-1,3-oxazinen
DE3914133A1 (de) * 1989-04-28 1990-10-31 Henkel Kgaa Verfahren zur herstellung von 2-oxazolinen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9425447A1 *

Also Published As

Publication number Publication date
WO1994025447A1 (fr) 1994-11-10
JPH08508724A (ja) 1996-09-17
DE4313511A1 (de) 1994-10-27

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