EP0548104A1 - Procede de production de melanges d'oligoglycerines a teneur elevee en diglycerine - Google Patents

Procede de production de melanges d'oligoglycerines a teneur elevee en diglycerine

Info

Publication number
EP0548104A1
EP0548104A1 EP19910914912 EP91914912A EP0548104A1 EP 0548104 A1 EP0548104 A1 EP 0548104A1 EP 19910914912 EP19910914912 EP 19910914912 EP 91914912 A EP91914912 A EP 91914912A EP 0548104 A1 EP0548104 A1 EP 0548104A1
Authority
EP
European Patent Office
Prior art keywords
silicate compounds
water
condensation
formula
glycerol
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Withdrawn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
EP19910914912
Other languages
German (de)
English (en)
Inventor
Udo Hees
Reinhard Bunte
Johannes Hachgenei
Andreas Botulinski
Arno Behr
Manfred Biermann
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 EP0548104A1 publication Critical patent/EP0548104A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups

Definitions

  • the invention relates to a process for the preparation of oligoglycerol mixtures with a high diglycerol content by condensation of glycerol in the presence of silicate compounds.
  • Diglycerin has gained great importance as a starting material for the production of fatty acid esters.
  • esters are used as emulsifiers in the food industry and cosmetics and in various technical applications, for example as a lubricant or stabilizer for PVC [J.Am.Oil. Che. Soc. 66, 153 (1989)].
  • diglycerin is generally based on glycerin which is reacted with glycidol [fats, soaps, paints, 88 101 (1986)] or epichlorohydrin [EP-A-0 333 984].
  • glycidol fats, soaps, paints, 88 101 (1986)
  • epichlorohydrin EP-A-0 333 984.
  • the reaction is not very selective, and glycidol and epichlorohydrin are difficult to handle and place high demands on occupational safety.
  • glycerol can be condensed in the presence of alkali bases. In this way, however, only mixtures are obtained which, in addition to diglycerol, contain even higher homologues and not negligible amounts of unreacted glycerol. Since the diglycerin has to be separated from these mixtures by distillation, which is associated with a high expenditure of time and energy, the object of the invention was to develop an improved process according to which oligoglycerol mixtures with a high diglycerol content are made available can.
  • the invention relates to a process for the preparation of oligoglycerol mixtures with a high diglycerol content, characterized in that glycerol is condensed in the presence of silicate compounds, the water of condensation is continuously removed from the reaction mixture and the reaction is terminated as soon as that theoretically required for the formation of diglycerol Amount of water has been separated.
  • M stands for lithium, sodium or potassium
  • n stands for whole or fractional numbers greater than 0 as well
  • n 1 and x is 0 or integers from 1 to 20,
  • the amorphous alkali silicates are glassy, water-soluble salts of silicic acid which have solidified from the melt flow. Their production is described, for example, in R ⁇ MPP's Chemie Lexikon, 8th edition, Franckh-Kosmos, Stuttgart, Vol. 6, p. 4593.
  • alkali silicates with a low SiO 2: M2O or m: n ratio (“basic” water glasses), as well as those with a high m: n ratio ("neutral” or “acidic” Water glasses ") are used.
  • the ratio SiO 2: M 0 is also referred to as the" module "of the silicate.
  • the crystalline alkali metal silicates are also known substances. They have a layered structure and are accessible, for example, by sintering alkali water glass or by hydrothermal reactions [Glastechn.Ber., 37 194 (1964)].
  • crystalline alkali metal silicates which catalyze the self-condensation of glycerol in the sense of the process according to the invention, z. B. Makatit (Na S ⁇ ' 4 ⁇ g • 5 H 2 0), Kenyait (Na2Si 22 ⁇ 45 • 10 H 2 0) or Ilerit (Na 2 S ⁇ * 8 ⁇ i7 • 9 H 2 0) into consideration [American mineral. 38, 163 (1953)].
  • the silicate compounds can be used as solids or also in the form of aqueous solutions with solids contents of 1 to 80, preferably 30 to 60% by weight, based on the silicate compound.
  • the silicate compounds are used in the condensation in amounts of 1 to 10, preferably 2 to 5,% by weight, based on the glycerol.
  • the condensation of the glycerol is carried out at temperatures from 200 to 260, preferably 240 to 250 ° C.
  • glycerol and silicate compound are introduced and heated to the reaction temperature in an inert gas atmosphere.
  • the water of condensation formed is separated off, for example, using a water separator.
  • the reaction is stopped when the amount of water theoretically required for the formation of diglycerin has been separated off.
  • the catalysts are used in the form of aqueous solutions in the condensation reaction, their water content must be taken into account when calculating the theoretical amount of condensation water for diglycerol formation.
  • the reaction time is 1 to 30, preferably 3 to 15 hours.
  • the catalyst can be separated from the reaction mixture, for example by filtering or centrifuging; this can also be dispensed with for a large number of applications.
  • the diglycerin is separated from the oligoglycerol mixture formed, for example, by distillation in a high vacuum. For a large number of applications, however, the oligoglycerol mixtures according to the invention can be used without further separation.
  • VI potassium hydroxide was used instead of a silicate compound.
  • module weight ratio Si0 2 : Na 2 0
  • Tri triglycerin
  • Tetra tetraglycerin

Landscapes

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

Abstract

On peut obtenir des mélanges d'oligoglycérines à teneur élevée en diglycérine en condensant de la glycérine en présence de composés de silicate, en enlevant en continu l'eau de condensation du mélange de réaction et en interrompant la réaction dès que la quantité d'eau théoriquement requise pour former la diglycérine a été extraite.
EP19910914912 1990-09-15 1991-09-06 Procede de production de melanges d'oligoglycerines a teneur elevee en diglycerine Withdrawn EP0548104A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4029323 1990-09-15
DE19904029323 DE4029323A1 (de) 1990-09-15 1990-09-15 Vefahren zur herstellung von oligoglyceringemischen mit hohem diglyceringehalt

Publications (1)

Publication Number Publication Date
EP0548104A1 true EP0548104A1 (fr) 1993-06-30

Family

ID=6414330

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19910914912 Withdrawn EP0548104A1 (fr) 1990-09-15 1991-09-06 Procede de production de melanges d'oligoglycerines a teneur elevee en diglycerine

Country Status (5)

Country Link
EP (1) EP0548104A1 (fr)
JP (1) JPH06500773A (fr)
CA (1) CA2091687A1 (fr)
DE (1) DE4029323A1 (fr)
WO (1) WO1992005133A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2743337A1 (fr) 2012-12-14 2014-06-18 Cognis IP Management GmbH Dérivés de polyglycérol tensioactifs

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5349094A (en) * 1992-06-12 1994-09-20 Henkel Kommanditgesellschaft Auf Aktien Process for the production of oligoglycerol mixtures of increased diglycerol content
DE4409569C1 (de) * 1994-03-21 1995-08-10 Henkel Kgaa Polyglycerinpolyricinoleate
DE4420516C2 (de) * 1994-06-13 1998-10-22 Henkel Kgaa Polyglycerinpolyhydroxystearate
DK0732318T3 (da) * 1995-03-15 2004-03-29 Nexus As Fremgangsmåde til fremstilling af oligomere og/eller polymere polyolforbindelser og anvendelse deraf i fremstillingen af emulgeringsmidler og overfladeaktive midler
DE19533539A1 (de) 1995-09-11 1997-03-13 Henkel Kgaa O/W-Emulgatoren
DE19641604C1 (de) 1996-10-09 1998-03-12 Goldschmidt Ag Th Polyglycerinpartialester von Fettsäuren und mehrfunktionellen Carbonsäuren, deren Herstellung und Verwendung

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB265147A (en) * 1926-01-27 1928-02-09 Henkel & Cie Gmbh Improved manufacture of a glycerine poor in poly-glycerines and containing di-glycerine
US2487208A (en) * 1946-12-23 1949-11-08 Colgate Palmolive Peet Co Preparation of diglycerol

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9205133A1 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2743337A1 (fr) 2012-12-14 2014-06-18 Cognis IP Management GmbH Dérivés de polyglycérol tensioactifs

Also Published As

Publication number Publication date
CA2091687A1 (fr) 1992-03-16
JPH06500773A (ja) 1994-01-27
WO1992005133A1 (fr) 1992-04-02
DE4029323A1 (de) 1992-03-19

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