EP0470107A1 - Procede de production de 2-alkyl-oxazolines ou d'alkenyl-2-oxazolines a partir de glycerides d'acides gras - Google Patents

Procede de production de 2-alkyl-oxazolines ou d'alkenyl-2-oxazolines a partir de glycerides d'acides gras

Info

Publication number
EP0470107A1
EP0470107A1 EP19900906193 EP90906193A EP0470107A1 EP 0470107 A1 EP0470107 A1 EP 0470107A1 EP 19900906193 EP19900906193 EP 19900906193 EP 90906193 A EP90906193 A EP 90906193A EP 0470107 A1 EP0470107 A1 EP 0470107A1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
titanium
alkyl
fatty acid
catalysts
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Withdrawn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
EP19900906193
Other languages
German (de)
English (en)
Inventor
Jürgen FALBE
William E. Fristad
Horst Jürgen KRAUSE
Peter Neumann
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 EP0470107A1 publication Critical patent/EP0470107A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C07D263/14—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 substituted by oxygen atoms

Definitions

  • the invention relates to a method for producing
  • R 1 is an optionally hydroxy-substituted hydrocarbon radical with at least 7, in particular 7 to 21, carbon atoms in the hydrocarbon chain, by condensation of fatty acid ethanolamides or of fatty acid glycerides and 2-aminoethanol as their precursors in the presence of catalysts in the liquid phase.
  • 2-alkyl-substituted 2-oxazolines are valuable products which are used, inter alia, as solvents or plasticizers and in particular as polymerization components. Numerous processes have been described for producing this class of compound:
  • Processes of the type mentioned at the outset are suitable, yields of up to about 85% of theory, based on the starting compound, being able to be achieved.
  • M is tetravalent titanium or zirconium and R 2 is an alkyl group with at least 2, in particular 2 to 4 carbon atoms, an acyl group with at least 2, in particular 2 to 10 carbon atoms or a 2-aminoethyleneoxy group or the remainder of a beta-diketone of the general formula III
  • R 2 is an alkyl group with at least 2, in particular 2 to 4 carbon atoms, an acyl group with at least 2, in particular 2 to 10 carbon atoms or a 2-aminoethyleneoxy group or the remainder of a beta-diketone of the general formula III
  • R 3 -C CH-CO-R 4 (III)
  • the method of the invention is applicable to all fatty acid glycerides which are derived from straight-chain or branched, saturated or unsaturated fatty acids having at least 8 carbon atoms, in particular having 8 to 22 carbon atoms, including hydroxy-substituted derivatives thereof.
  • Preferred starting compounds for the process of the invention are fatty acid glycerides, in particular triglycerides, of vegetable, animal or marine origin, including technical mixtures, and derivatives thereof hardened by catalytic hydrogenation.
  • Typical representatives of the fatty acids occurring in the above-mentioned glycerides are caprylic, capric, myristic, palmitin, stearin, 12-hydroxystearin, arachine, behen, lignocerine, laurolein, myristole, palmitolein, oil -, Gadolein-, Eruca-, Ricinol-, Linol-, Linolen- and Arachidon- acid.
  • it is usually not the fatty acid glycerides that are used, but rather technical mixtures of the same as are available from natural raw materials, e.g. from lauric oils, coconut oil, palm oil, palm kernel oil,
  • titanium or zirconium compounds which can be used as catalysts in the process of the invention are known and the majority are commercially available.
  • Condensation products of titanium (IV) or zirconium (IV) tetraalkoxylates with polyfunctional alkanols with 3 to 12 carbon atoms and 2 to 6 hydroxyl groups such as glycerol, trimethylolpropane and
  • Pentaerythritol are esterification and / or transesterification catalysts which are described, for example, in US Pat. No. 4,705,764, the content of which is referred to here.
  • a suitable polyalkanol is also polyvinyl alcohol.
  • the titanium or zirconium tetra- (2-amino- ethoxylates) can be produced from titanium or zirconium tetraalkoxylates and 2-aminoethanol.
  • titanium or zirconium acetylacetonates of the general formula (IV) are used as catalysts
  • R 5 is an alkyl group having 1 to 4 carbon atoms
  • ACA is an acetylacetonate radical and m is the number 0 and n is the number 4 or m is the number 2 and n is the number 2.
  • polycondensation products of esters of titanium acid with monoalkanols with 2 to 10 are used as catalysts
  • the catalysts to be used according to the invention are used in an amount of 0.1 to 10, preferably 1 to 5, mol%, based on the fatty acid residues present.
  • the 2-alkyl- or alkenyl-substituted 2-oxazolines can be prepared directly from fatty acid glycerides by reacting them in the presence of ethanolamine at elevated temperature and at atmospheric pressure to form the fatty acid ethanolamides, water and glycerol formed and not unreacted or excess ethanolamine is virtually completely removed by distillation in vacuo and the reaction mixture is allowed to react in a second reaction stage in vacuo with a further increase in the reaction temperature.
  • the glycerides react in the presence of ethanolamine and the claimed catalysts in the first reaction stage to fatty acid ethanolamides, which react in the second reaction stage to the 2-oxazolines.
  • the ethanolamine is preferably used in a 50 to 400 mol% excess, based on the starting material.
  • a reaction temperature of less than 185 ° C. is preferably used in the first reaction stage and in the second one from 185 to 270 ° C.
  • the catalysts are preferably used in an amount of 0.1 to 10, preferably 1 to 5, mol%, based on the fatty acid residues present.
  • titanium tetraalcoholates in particular selected from the group formed from titanium tetraethylate, tetrapropylate, tetraisopropylate and tetrabutylate, are preferably used.
  • the second stage of the reaction is carried out in vacuo and the water of reaction formed is distilled together with the 2-alkyl- or alkenyl-substituted 2-oxazolines with further separation during the distillation.
  • the water of reaction can also be removed by azeotropic distillation before the 2-alkyl- or alkenyl-2-oxazolines are distilled.
  • the soy fatty acid ethanolamide thus obtained was heated in vacuo to 194 to 268 ° C., the 2-soy fatty alkenyl-2-oxazoline and water simultaneously distilling over at 160 to 194 ° C. and 0.07 hPa. Most of the water was condensed in the cold trap. In order to rid the distilled oxazoline of any entrained water, the
  • rapeseed oil the fatty acid component of which consists of approximately 40% erucic acid, was reacted with ethanolamine to give 2- (rapeseed fatty alkyl) -2-oxazoline.
  • degummed soybean oil Analogous to the preparation for example 1, degummed soybean oil was reacted with ethanolamine in the presence of titanium (IV) -diisopropoxy-bis-acetylacetonate to give 2- (soybean fatty alkenyl) -2-oxazoline.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Selon le procédé de production de 2-alkyl-oxazolines ou d'alkényl-2-oxazolines en grandes quantités, dont le groupe alkyle ou alkényle est un résidu hydrocarbure avec au moins 7 atomes de carbone, le cas échéant à substitution hydroxy, on convertit des glycérides d'acides gras ayant au moins 8 atomes de carbone avec du 2-aminoéthanol en présence de composés de titane ou de zirconium du type (M(OR2)4, où M est Ti ou Zr.
EP19900906193 1989-04-28 1990-04-19 Procede de production de 2-alkyl-oxazolines ou d'alkenyl-2-oxazolines a partir de glycerides d'acides gras Withdrawn EP0470107A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19893914159 DE3914159A1 (de) 1989-04-28 1989-04-28 Verfahren zur herstellung von 2-alkyl- bzw. alkenyl-2-oxazolinen aus fettsaeureglyceriden
DE3914159 1989-04-28

Publications (1)

Publication Number Publication Date
EP0470107A1 true EP0470107A1 (fr) 1992-02-12

Family

ID=6379734

Family Applications (2)

Application Number Title Priority Date Filing Date
EP90107492A Withdrawn EP0394854A1 (fr) 1989-04-28 1990-04-19 Procédé de préparation de 2-alkyl ou 2-alcényl-2-oxazolines au départ de glycérides d'acides gras
EP19900906193 Withdrawn EP0470107A1 (fr) 1989-04-28 1990-04-19 Procede de production de 2-alkyl-oxazolines ou d'alkenyl-2-oxazolines a partir de glycerides d'acides gras

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP90107492A Withdrawn EP0394854A1 (fr) 1989-04-28 1990-04-19 Procédé de préparation de 2-alkyl ou 2-alcényl-2-oxazolines au départ de glycérides d'acides gras

Country Status (6)

Country Link
EP (2) EP0394854A1 (fr)
JP (1) JPH04504853A (fr)
BR (1) BR9007324A (fr)
CA (1) CA2053876A1 (fr)
DE (1) DE3914159A1 (fr)
WO (1) WO1990013545A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4313511A1 (de) * 1993-04-24 1994-10-27 Henkel Kgaa Verfahren zur Herstellung von Oxazolinen und Oxazinen im Batch-Verfahren
EP0757062B1 (fr) 1995-08-01 2000-02-23 BASF Aktiengesellschaft Polymères et oligomères à terminaison 2-oxazolinyle et leur utilisation en tant qu'agents de compatibilisation
JPH09124913A (ja) 1995-11-06 1997-05-13 Nippon G Ii Plast Kk ポリフェニレンエーテル系樹脂組成物
DE19603304C2 (de) * 1996-01-25 1999-09-09 Inventa Ag Verwendung von Oxazolin-Verbindungen als Aktivator zur Auslösung der anionischen Lactampolymerisation
DE19739686A1 (de) * 1997-09-10 1999-03-11 Basf Ag Thermoplastische Formmassen auf Basis von Polyestern und Polycarbonat
JP7405015B2 (ja) * 2020-06-22 2023-12-26 日油株式会社 ワックス熱応答性向上剤およびこれを含有するワックス組成物

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1067437B (de) * 1956-05-11 1959-10-22 Rohm & Haas Company, Philadelphia, Pa. (V. St. A.) Verfahren zur Herstellung von 4,4-dialkyl-2vinyl- und 4,4-dialkyl-2-isopropenylsu'bstituierten Oxazolinen und 5,6-Dihydro-4H!-1,3-oχ3zinen sowie deren Spiranen
US3681329A (en) * 1970-05-04 1972-08-01 Allied Chem Process for the preparation of cyclic iminoethers
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

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9013545A1 *

Also Published As

Publication number Publication date
WO1990013545A1 (fr) 1990-11-15
DE3914159A1 (de) 1990-10-31
JPH04504853A (ja) 1992-08-27
CA2053876A1 (fr) 1990-10-29
BR9007324A (pt) 1992-04-28
EP0394854A1 (fr) 1990-10-31

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