EP1032564A1 - Procede de preparation de composes epoxydes thermostables - Google Patents

Procede de preparation de composes epoxydes thermostables

Info

Publication number
EP1032564A1
EP1032564A1 EP98958869A EP98958869A EP1032564A1 EP 1032564 A1 EP1032564 A1 EP 1032564A1 EP 98958869 A EP98958869 A EP 98958869A EP 98958869 A EP98958869 A EP 98958869A EP 1032564 A1 EP1032564 A1 EP 1032564A1
Authority
EP
European Patent Office
Prior art keywords
epoxides
epoxidized
compounds
olefinically unsaturated
water
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Withdrawn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
EP98958869A
Other languages
German (de)
English (en)
Inventor
Ralf Bohlander
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.)
BASF Personal Care and Nutrition GmbH
Original Assignee
Cognis Deutschland GmbH and Co KG
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 Cognis Deutschland GmbH and Co KG filed Critical Cognis Deutschland GmbH and Co KG
Publication of EP1032564A1 publication Critical patent/EP1032564A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
    • C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/32—Separation; Purification

Definitions

  • the invention relates to a work-up process for the production of thermostable epoxy compounds, in which they are first washed neutral or alkaline, the phases are separated, dried, treated with selected basic solids and then finally filtered.
  • Epoxy compounds have a wide range of applications in the production of plastics, plastic foams, surface coatings and paints. It is desirable that these substances have the highest possible epoxy oxygen content, at the same time the content of volatile components must be as low as possible in order to prevent fogging on the plastic parts. Finally, the products must be sufficiently thermostable, ie at Higher temperatures, such as occur in the production of the polymers, must not lead to undesired crosslinking of the epoxides with one another and the build-up of viscosity.
  • the object of the invention was therefore to provide a process for the preparation of thermostable epoxides which is free from the disadvantages described.
  • the invention relates to a process for the preparation of thermally stable epoxy compounds, in which olefinically unsaturated compounds are epoxidized in a manner known per se, and the resulting oxirane compounds
  • organic value phase which is characterized in that the organic value phase is then treated with solid, basic aluminum oxides, aluminum hydroxides and / or alkali silicates and filtered.
  • the epoxy compounds obtained in this way are distinguished by a higher epoxy oxygen content compared to prior art work-up processes even after exposure to temperature and show a lower tendency to crosslink during storage and to build up an undesirable viscosity.
  • the number of washing steps is reduced with the proposed method, which leads to a technical simplification and reduces the amount of waste water.
  • the invention includes the finding that higher yields are achieved when the epoxy compounds obtainable by the process according to the invention are worked up by distillation.
  • Epoxides of olefinically unsaturated fatty substances are preferably used, such as, for example, epoxides of olefinically unsaturated triglycerides, fatty acid lower alkyl esters (ie esters of fatty acids with 6 to 22 carbon atoms with alcohols with 1 to 8 carbon atoms) and / or fatty alcohols.
  • Epoxidized triglycerides based on soybean oil, linseed oil, rapeseed oil, sunflower oil, tall oil, cottonseed oil, peanut oil, palm oil or claw oil, with epoxides having been found to be optimal with regard to the color quality of the products high degree of epoxidation and low iodine number.
  • Epoxidized triglycerides are known substances which are used in other technical fields as so-called “epoxy plasticizers”. They are produced by epoxidation of unsaturated fats and oils according to the so-called “in situ performic acid process", which is described in J.Am.Chem.Soc . 67, 412 (1945).
  • olefinic double bonds of the glyceridically bonded fatty acids are converted into oxirane rings by epoxidation.
  • Particularly suitable are triglycerides with an iodine number in the range from 50 to 150 which, with extensive epoxidation of the olefinic double bonds, are converted into epoxides with a content of 3 to 10% by weight epoxy oxygen.
  • the use of epoxidized soybean oil and / or epoxidized soybean fatty acid methyl ester is preferred.
  • epoxidized fatty alcohols cf. also D.Swern in J.Am.Chem.Soc. 66, 1925 (1944).
  • epoxidized fatty substances which are to a certain extent functionalized olefins
  • epoxidized olefins having 6 to 18 carbon atoms which carry the epoxy group either at the end or inside the molecule.
  • Typical examples are ⁇ -epoxides of decene, dodecene, tetradecene, hexadecene and octadecene and corresponding technical mixtures of these olefins.
  • the basic solids for refining the epoxides are aluminum oxides, aluminum hydroxides and alkaline silicates such as, for example, Primisile, Celatome or Celite.
  • the amount of these substances used can be 0.5 to 5, preferably 1 to 3,% by weight, based on the epoxides.
  • alkali solution means, for example, aqueous sodium hydroxide or sodium carbonate solutions with a solids content in the range from 1 to 15% by weight.
  • Epoxidized soybean oil was purified using the following procedures:
  • Example 1 is according to the invention, Examples V1 to V3 are used for comparison.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Compounds (AREA)

Abstract

Procédé de préparation de composés époxydes thermostables, qui consiste à époxyder de manière connue des composés oléfiniquement insaturés, puis (a) à laver les composés d'oxirane qui en résultent à l'aide d'eau et/ou d'une solution alcaline aqueuse et (b) à séparer et à sécher la phase organique de valeur. Ledit procédé est caractérisé en ce que ladite phase organique est finalement traitée à l'aide d'oxydes d'aluminium, d'hydroxydes d'aluminium et/ou de silicates alcalins basiques solides, et ensuite filtrée.
EP98958869A 1997-11-04 1998-10-24 Procede de preparation de composes epoxydes thermostables Withdrawn EP1032564A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19748573A DE19748573A1 (de) 1997-11-04 1997-11-04 Verfahren zur Herstellung thermostabiler Epoxidverbindungen
DE19748573 1997-11-04
PCT/EP1998/006765 WO1999023085A1 (fr) 1997-11-04 1998-10-24 Procede de preparation de composes epoxydes thermostables

Publications (1)

Publication Number Publication Date
EP1032564A1 true EP1032564A1 (fr) 2000-09-06

Family

ID=7847503

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98958869A Withdrawn EP1032564A1 (fr) 1997-11-04 1998-10-24 Procede de preparation de composes epoxydes thermostables

Country Status (4)

Country Link
US (1) US6278003B1 (fr)
EP (1) EP1032564A1 (fr)
DE (1) DE19748573A1 (fr)
WO (1) WO1999023085A1 (fr)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1231894B (de) * 1964-07-21 1967-01-05 Huels Chemische Werke Ag Herstellen von Formteilen oder UEberzuegen durch Aushaerten von Polybutadienepoxiden
DE3002861C2 (de) * 1980-01-26 1981-11-12 Degussa Ag, 6000 Frankfurt Verfahren zur Herstellung von Epoxyalkanen
JPS5869207A (ja) * 1981-10-21 1983-04-25 Nippon Petrochem Co Ltd エポキシ化物の精製方法
US4772732A (en) 1986-05-08 1988-09-20 Basf Corporation Method for purification of butylene oxide

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9923085A1 *

Also Published As

Publication number Publication date
WO1999023085A1 (fr) 1999-05-14
US6278003B1 (en) 2001-08-21
DE19748573A1 (de) 1999-05-06

Similar Documents

Publication Publication Date Title
DE60104694T2 (de) Aus pflanzenölen stammende weichmacher
DE4209779C1 (fr)
WO1994017027A1 (fr) Procede de fabrication d'esters d'acides gras d'alcools inferieurs
DE3238866A1 (de) Verfahren zur reinigung eines epoxidierungsproduktes
EP1644469B1 (fr) Procede d'epuration des acides gras
US7544763B2 (en) Catalyst-free process for the manufacture of a fatty acid ester oil polyol
DE3814850A1 (de) Verfahren zur herstellung von langkettigen kohlenstoffverbindungen mit vicinalen diolgruppen
WO1996029306A1 (fr) Procede d'extraction de carotene a partir d'huile de palme
DE69830518T2 (de) Verfahren zur herstellung von hochreinen fettsäure-niedrigalkylestern
WO1999023085A1 (fr) Procede de preparation de composes epoxydes thermostables
DE2362115A1 (de) Verfahren zur abtrennung von iso- buten aus c tief 4 -kohlenwasserstoffgemischen
DE1944381B2 (de) Verfahren zur herstellung von 1,1- dihydroperfluoralkanolen
EP0943596B1 (fr) Procédé pour la préparation d'alcools gras insaturés à partir d'huiles lauriques
DE2937831C2 (fr)
US3257438A (en) Process for removing stilbene from tall oil fatty acids
DE1210850B (de) Verfahren zur Herstellung von Epoxyden
EP0033110B1 (fr) Procédé de production d'époxyalcanes
US3328430A (en) Epoxidation process
CA2020307A1 (fr) Procede de separation thermique de pate de neutralisation
DE19626458C5 (de) Verfahren zur Herstellung von Estern der schwerflüchtigen Alkohole Trismethylolpropan, Trismethylolethan und Pentaerythrit mit nativen Fettsäuren
US2166812A (en) Process for the separation of the constituents of organic mixtures containing both resin acids and fatty acids, particularly tall oil
US2275186A (en) Process for refining tall oil
DE10317204A1 (de) Carbonsäureester auf Basis von 2-Hydroxymethylnorbornan
EP1516865B1 (fr) Esters d' acides carboxyliques à base de 3-(4'-méthylcyclohexyl) butanol à bas point d' écoulement
US3391191A (en) Liquid phase decarboxylation of fatty acids to ketones

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20000422

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): BE DE FR GB NL

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: COGNIS DEUTSCHLAND GMBH & CO. KG

17Q First examination report despatched

Effective date: 20030812

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20031223