DE4117033A1 - Prodn. of oligo:glycerol mixts. - by condensing glycerol in presence of boron cpd. and continually removing water formed - Google Patents

Prodn. of oligo:glycerol mixts. - by condensing glycerol in presence of boron cpd. and continually removing water formed

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Publication number
DE4117033A1
DE4117033A1 DE19914117033 DE4117033A DE4117033A1 DE 4117033 A1 DE4117033 A1 DE 4117033A1 DE 19914117033 DE19914117033 DE 19914117033 DE 4117033 A DE4117033 A DE 4117033A DE 4117033 A1 DE4117033 A1 DE 4117033A1
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Germany
Prior art keywords
diglycerol
glycerol
alpha
weight
mixts
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Withdrawn
Application number
DE19914117033
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German (de)
Inventor
Udo Dr Hees
Reinhard Dr Bunte
Johannes Dr Hachgenei
Christian Dr Block
Manfred Dr Biermann
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to DE19914117033 priority Critical patent/DE4117033A1/en
Publication of DE4117033A1 publication Critical patent/DE4117033A1/en
Withdrawn legal-status Critical Current

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    • 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

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

Abstract

Prodn. of oligoglycerol mixts. is effected by condensing glycerol in the presence of a B cpd. while continuously removing the H20 formed. The reaction is terminated when the amt. of H20 removed corresponds to the amt. theoretically required for diglycerol formation. The process gives prods. with a higher diglycerol content than processes using alkali metal base catalysts and with a higher content of alpha, alpha-linked diglycerol than processes using silicate catalysts. The reaction is effected at 200-260 deg.C. in the presence of 1-10 wt.% Li, Na or K metaborate or Na tetraborate. USE/ADVANTAGE - Diglycerol is useful for making fatty acid esters, which are useful as food and cosmetic emulsifiers and for industrial applications, e.g. as lubricants or stabilisers for PVC.ef

Description

Die Erfindung betrifft ein Verfahren zur Herstellung von Oligo­ glyceringemischen durch Kondensation von Glycerin in Gegenwart von Borverbindungen.The invention relates to a process for the preparation of oligo glycerol mixtures by condensation of glycerol in the presence of Boron compounds.

Diglycerin hat als Ausgangsmaterial für die Herstellung von Fett­ säureestern große Bedeutung erlangt. Derartige Ester finden Ver­ wendung als Emulgatoren in der Nahrungsmittelindustrie und der Kosmetik sowie in verschiedenen technischen Anwendungen, bei­ spielsweise als Schmierstoffe oder Stabilisatoren für PVC (J. Am. Oil. Chem. Soc. 66, 153 (1989)).Diglycerin has as a starting material for the production of fat Acid esters acquired great importance. Such esters find Ver use as emulsifiers in the food industry and the Cosmetics as well as in various technical applications, at For example, as lubricants or stabilizers for PVC (J.A. Oil., Chem. Soc., 66, 153 (1989)).

Zur Herstellung von Diglycerin wird in der Regel von Glycerin ausgegangen, das mit Glycidol (Fette, Seifen, Anstrichmitt., 88, 101 (1986)) oder Epichlorhydrin (EP 03 33 984 A1) umgesetzt wird. Die Reaktion verläuft jedoch wenig selektiv, zudem sind Glycidol und Epichlorhydrin schwer zu handhaben und stellen hohe Anforderungen an den Arbeitsschutz.For the production of diglycerol is usually of glycerol with glycidol (fats, soaps, paints., 88, 101 (1986)) or epichlorohydrin (EP 03 33 984 A1). The Reaction, however, is less selective, besides, glycidol and Epichlorohydrin difficult to handle and make high demands to occupational safety.

Alternativ hierzu kann Glycerin in Gegenwart von Alkalibasen kon­ densiert werden. In Abhängigkeit davon, ob die Kondensation zur Verknüpfung zweier primärer (alpha, alpha), zweier sekundärer (be­ ta, beta) OH-Funktionen oder einer primären und einer sekundären Hydroxylgruppe (alpha, beta) führt, unterscheidet man drei verschiedene Kondensationstypen unter denen das alpha, alpha-Diglycerin eine besondere technische Bedeutung be­ sitzt.Alternatively, glycerol in the presence of alkali bases kon be densified. Depending on whether the condensation to Linking two primary (alpha, alpha), two secondary (be ta, beta) OH functions or one primary and one secondary Hydroxyl group (alpha, beta) leads to a distinction between three  different types of condensation among which alpha, alpha-diglycerol be of special technical importance be sitting.

Die alkalische Kondensation ist jedoch mit einer Reihe von Nach­ teilen behaftet. Insbesondere sind auf diesem Wege nur Gemische erhältlich, die neben Diglycerin noch höhere Homologe sowie nicht zu vernachlässigende Mengen an nichtumgesetztem Glycerin enthal­ ten. Das Diglycerin muß aus diesen Gemischen destillativ abge­ trennt werden, was mit einem hohem Aufwand an Zeit und Energie verbunden ist. Aus diesem Grunde wird die Herstellung von Oligo­ glyceringemischen angestrebt, die einen möglichst hohen Diglyce­ rinanteil aufweisen. Führt man die Eigenkondensation des Glycerins in Gegenwart von Silicaten als Katalysatoren durch, werden zwar diglycerinreiche Oligoglycerine erhalten, der Anteil an alpha, al­ pha-verknüpften Dimeren in diesen Gemischen ist jedoch ver­ gleichsweise gering.However, the alkaline condensation is with a series of after share tainted. In particular, only mixtures are in this way available, which in addition to diglycerol even higher homologs and not negligible amounts of unreacted glycerol The diglycerol must be distilled off from these mixtures be separated, resulting in a great deal of time and energy connected is. For this reason, the production of oligo Glycerenemischen sought, the highest possible Diglyce have rinanteil. Performing the self-condensation of glycerol in the presence of silicates as catalysts, though diglycerol-rich oligoglycerols obtained, the proportion of alpha, al However, pha-linked dimers in these mixtures is ver at the same time low.

Die Aufgabe der Erfindung bestand somit darin, ein Verfahren zur Herstellung von Oligoglyceringemischen zu entwickeln, das frei von den geschilderten Nachteilen ist.The object of the invention was therefore to provide a method for Production of oligoglycerine mixtures to develop, free of the disadvantages described is.

Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Oligoglyceringemischen, das sich dadurch auszeichnet, daß man Glycerin in Gegenwart von Borverbindungen kondensiert, das Kon­ densationswasser kontinuierlich aus der Reaktionsmischung entfernt und die Reaktion abbricht, sobald die zur Bildung von Diglycerin theoretisch erforderliche Menge Wasser abgeschieden worden ist.The invention relates to a process for the preparation of Oligoglyceringemischen, which is characterized in that one Glycerol condensed in the presence of boron compounds, the Kon condensation water continuously removed from the reaction mixture and the reaction stops as soon as the formation of diglycerol theoretically required amount of water has been deposited.

Überraschenderweise wurde gefunden, daß die Verwendung von Bor­ verbindungen in der GlycerinkondensationSurprisingly, it has been found that the use of boron compounds in the Glycerinkondensation

  • - gegenüber Alkalikatalysatoren zu Oligoglyceringemischen mit einem vergleichsweise höheren Diglycerinanteil und- Compared with alkali catalysts to Oligoglyceringemischen with a comparatively higher proportion of diglycerol and
  • - gegenüber Silicatkatalysatoren zu Oligoglyceringemischen mit einem vergleichsweise höheren Gehalt an alpha,alpha-verknüpf­ tem Diglycerin- Compared to silicate catalysts to Oligoglyceringemischen with a comparatively higher content of alpha, alpha-linked diglycerol

führt.leads.

Unter Borverbindungen, die im Sinne des erfindungsgemäßen Verfah­ rens als Katalysatoren für die Glycerinkondensation in Betracht kommen, sind amorphe Alkaliborate ausgewählt aus der Gruppe, die von Lithiummetaborat, Natriummetaborat, Natriumtetraborat und Ka­ liummetaborat gebildet wird, zu verstehen. Bevorzugt ist der Ein­ satz von Natriummetaborat.Boron compounds which are used in the context of the process according to the invention as catalysts for the Glycerinkondensation into consideration come, amorphous alkali borates are selected from the group that of lithium metaborate, sodium metaborate, sodium tetraborate and Ka liummetaborat is formed to understand. Preferably, the one Set of sodium metaborate.

Die Borverbindungen können in der Kondensation in Mengen von 1 bis 10, vorzugsweise 2 bis 5 Gew.-% - bezogen auf das Glycerin - ein­ gesetzt werden. Die Temperatur, bei der die Kondensation des Gly­ cerins durchgeführt wird, kann 200 bis 260, vorzugsweise 240 bis 250°C betragen.The boron compounds may be used in the condensation in amounts of 1 to 10, preferably 2 to 5 wt .-% - based on the glycerol - a be set. The temperature at which the condensation of Gly cerins may be 200 to 260, preferably 240 to 250 ° C.

Zur Durchführung der Kondensationsreaktion werden Glycerin und Borverbindung vorgelegt und in einer Inertgasatmosphäre auf die Reaktionstemperatur erhitzt. Zur Verlagerung des Gleichgewichtes wird das entstehende Kondensationswasser beispielsweise über einen Wasserabscheider abgetrennt. Die Reaktion wird abgebrochen, wenn die zur Bildung von Diglycerin theoretisch erforderliche Menge Wasser abgeschieden worden ist. Im allgemeinen beträgt die Reak­ tionszeit 1 bis 30, vorzugsweise 3 bis 15 h. Die Abtrennung des Diglycerins aus dem gebildeten Oligoglyceringemisch erfolgt beispielsweise durch Destillation im Hochvakuum. Für eine Vielzahl von Anwendungen können jedoch die erfindungsgemäßen Oligoglyce­ ringemische ohne weitere Auftrennung eingesetzt werden.To carry out the condensation reaction, glycerol and Boron compound submitted and in an inert gas atmosphere on the Reaction temperature heated. To shift the balance For example, the resulting condensation water over a Separated water separator. The reaction is stopped when the amount theoretically required to form diglycerin Water has been separated. In general, the reac tion time 1 to 30, preferably 3 to 15 h. The separation of the Diglycerol from the oligoglycerol mixture formed takes place  for example by distillation in a high vacuum. For a variety however, applications of the invention may be the oligoglyce of the invention Ringemische be used without further separation.

Die nachfolgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern, ohne ihn darauf einzuschränken.The following examples are intended to form the subject of the invention explain it in more detail without restricting it to it.

BeispieleExamples Beispiel 1example 1

In einem 250-ml-Dreihalskolben mit Rückflußkühler, Wasserabschei­ der und Innenthermometer wurden 184 g (2 mol) Glycerin (99,5gew.-%ig) vorgelegt und mit 4,4 g (0,07 mol) Natriummetaborat (NaBO2) - entsprechend 2,4 Gew.-% bezogen auf das Glycerin - versetzt. Die Reaktionsmischung wurde in einer Stickstoffatmosphäre auf 240°C erhitzt, wobei das Kondensationswasser über den Wasserabscheider entfernt wurde. Die Reaktion wurde abgebrochen, nachdem die für die Bildung von Diglycerin erforderliche Menge abgeschieden worden war. Die Zusammensetzung des Oligoglyceringemisches wurde mittels HPLC ermittelt.In a 250 ml three-necked flask with reflux condenser, Wasserabschei and internal thermometer 184 g (2 mol) of glycerol (99.5 wt .-% strength) were introduced and with 4.4 g (0.07 mol) of sodium metaborate (NaBO 2 ) - corresponding to 2.4 wt .-% based on the glycerol - added. The reaction mixture was heated to 240 ° C in a nitrogen atmosphere, with the condensation water removed via the water separator. The reaction was stopped after the amount required for the formation of diglycerol had been removed. The composition of the oligoglycerol mixture was determined by HPLC.

Kenndaten des ProduktesCharacteristics of the product Glyceringlycerin 25 Gew.-%25% by weight Diglycerindiglycerol 37 Gew.-%37% by weight Triglycerintriglycerol 15 Gew.-%15% by weight Tetraglycerintetraglycerol 9 Gew.-%9% by weight Oligoglycerineoligoglycerins 14 Gew.-%14% by weight

Zusammensetzung der Diglycerin-FraktionComposition of the diglycerin fraction beta,beta-Diglycerinbeta, beta-diglycerol 8,9 Gew.-%8.9% by weight alpha,beta-Diglycerinalpha, beta-diglycerol 39,1 Gew.-%39.1% by weight alpha,alpha-Diglycerinalpha, alpha-diglycerol 52,0 Gew.-%52.0% by weight

Vergleichsbeispiel 1Comparative Example 1

Analog Beispiel 1 wurden 184 g Glycerin in Gegenwart von 4,4 g (0,08 mol) Kaliumhydroxid - entsprechend 2,4 Gew.-% bezogen auf das Glycerin - kondensiert.Analogously to Example 1, 184 g of glycerol in the presence of 4.4 g (0.08 mol) of potassium hydroxide - corresponding to 2.4 wt .-% based on the glycerin - condenses.

Kenndaten des ProduktesCharacteristics of the product Glyceringlycerin 32 Gew.-%32% by weight Diglycerindiglycerol 29 Gew.-%29% by weight Triglycerintriglycerol 16 Gew.-%16% by weight Tetraglycerintetraglycerol 9 Gew.-%9% by weight Oligoglycerineoligoglycerins 14 Gew.-%14% by weight

Zusammensetzung der Diglycerin-FraktionComposition of the diglycerin fraction beta,beta-Diglycerinbeta, beta-diglycerol 1,0 Gew.-%1.0% by weight alpha,beta-Diglycerinalpha, beta-diglycerol 25,9 Gew.-%25.9% by weight alpha,alpha-Diglycerinalpha, alpha-diglycerol 73,1 Gew.-%73.1% by weight

Vergleichsbeispiel 2Comparative Example 2

Analog Beispiel 1 wurden 184 g Glycerin in Gegenwart von 4,4 g (0,03 mol) Natriumsilicat (Portil(R) AW, Modul : 2,03, Fa. Henkel KGaA) - entsprechend 2,4 Gew.-% bezogen auf das Glycerin - kon­ densiert.Analogously to Example 1, 184 g of glycerol in the presence of 4.4 g (0.03 mol) of sodium silicate (Portil (R) AW, modulus: 2.03, Fa. Henkel KGaA) - corresponding to 2.4 wt .-% based on the glycerol - condensed kon.

Kenndaten des ProduktesCharacteristics of the product Glyceringlycerin 20 Gew.-%20% by weight Diglycerindiglycerol 41 Gew.-%41% by weight Triglycerintriglycerol 20 Gew.-%20% by weight Tetraglycerintetraglycerol 10 Gew.-%10% by weight Oligoglycerineoligoglycerins 9 Gew.-%9% by weight

Zusammensetzung der Diglycerin-FraktionComposition of the diglycerin fraction beta,beta-Diglycerinbeta, beta-diglycerol 22,5 Gew.-%22.5% by weight alpha,beta-Diglycerinalpha, beta-diglycerol 48,7 Gew.-%48.7% by weight alpha,alpha-Diglycerinalpha, alpha-diglycerol 28,8 Gew.-%28.8% by weight

Claims (4)

1. Verfahren zur Herstellung von Oligoglyceringemischen, dadurch gekennzeichnet, daß man Glycerin in Gegenwart von Borverbin­ dungen kondensiert, das Kondensationswasser kontinuierlich aus der Reaktionsmischung entfernt und die Reaktion abbricht, so­ bald die zur Bildung von Diglycerin theoretisch erforderliche Menge Wasser abgeschieden worden ist.1. A process for the preparation of Oligoglyceringemischen, characterized in that condensing glycerol in the presence of Borverbin applications, the condensation water continuously removed from the reaction mixture and the reaction stops, as soon as the theoretically required for the formation of diglycerol amount of water has been deposited. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man als Borverbindungen amorphe Alkaliborate ausgewählt aus der Grup­ pe, die von Lithiummetaborat, Natriummetaborat, Natriumtetra­ borat und Kaliummetaborat gebildet wird, einsetzt.2. The method according to claim 1, characterized in that as Boron compounds amorphous alkali borates selected from Grup derived from lithium metaborate, sodium metaborate, sodium tetra borate and potassium metaborate. 3. Verfahren nach den Ansprüchen 1 und 2, dadurch gekennzeichnet, daß man die Borverbindungen in Mengen von 1 bis 10 Gew.-% - bezogen auf das Glycerin - einsetzt.3. Process according to claims 1 and 2, characterized in that that the boron compounds in amounts of 1 to 10 wt .-% - based on the glycerin - uses. 4. Verfahren nach mindestens einem der Ansprüche 1 bis 3 dadurch gekennzeichnet, daß man die Kondensation bei Temperaturen von 200 bis 260°C durchführt.4. The method according to at least one of claims 1 to 3 characterized characterized in that the condensation at temperatures of 200 to 260 ° C performs.
DE19914117033 1991-05-24 1991-05-24 Prodn. of oligo:glycerol mixts. - by condensing glycerol in presence of boron cpd. and continually removing water formed Withdrawn DE4117033A1 (en)

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4409569C1 (en) * 1994-03-21 1995-08-10 Henkel Kgaa New poly:glycerol poly:ricinoleate ester(s)
EP0732318A1 (en) * 1995-03-15 1996-09-18 Nexus A/S A process of preparing oligomeric and/or polymeric polyol compounds and their use in the production of emulsifying agents and surfactants
US5840943A (en) * 1994-06-13 1998-11-24 Henkel Kommanditgesellschaft Auf Aktien Polyolpolyhydroxystearates
US6242499B1 (en) 1996-10-09 2001-06-05 Goldschmidt Ag Polyglycerol partial esters of fatty acids and polyfunctional carboxylic acids, their preparation and use
US6264961B1 (en) 1995-09-11 2001-07-24 Henkel Kommanditgesellschaft Auf Aktien Oil-water emulsifiers
EP2100871A1 (en) 2008-03-10 2009-09-16 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Catalytic method for preparing lactic acid from renewable raw materials
WO2010111570A1 (en) * 2009-03-27 2010-09-30 E. I. Du Pont De Nemours And Company Polyglycerol aldehydes
US8404779B2 (en) 2009-03-27 2013-03-26 Actamax Surgical Materials Llc Tissue adhesive and sealant comprising polyglycerol aldehyde
US9474916B2 (en) 2013-08-08 2016-10-25 Evonik Degussa Gmbh Carbamates from glycerine carbonate for pearlization

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4409569C1 (en) * 1994-03-21 1995-08-10 Henkel Kgaa New poly:glycerol poly:ricinoleate ester(s)
US5736581A (en) * 1994-03-21 1998-04-07 Henkel Kommanditgesellschaft Auf Aktien Polyglycerol polyricinoleates
US5840943A (en) * 1994-06-13 1998-11-24 Henkel Kommanditgesellschaft Auf Aktien Polyolpolyhydroxystearates
EP0732318A1 (en) * 1995-03-15 1996-09-18 Nexus A/S A process of preparing oligomeric and/or polymeric polyol compounds and their use in the production of emulsifying agents and surfactants
US6264961B1 (en) 1995-09-11 2001-07-24 Henkel Kommanditgesellschaft Auf Aktien Oil-water emulsifiers
US6242499B1 (en) 1996-10-09 2001-06-05 Goldschmidt Ag Polyglycerol partial esters of fatty acids and polyfunctional carboxylic acids, their preparation and use
EP2100871A1 (en) 2008-03-10 2009-09-16 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Catalytic method for preparing lactic acid from renewable raw materials
DE102008013474A1 (en) 2008-03-10 2009-09-24 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Catalytic process for the recovery of basic chemicals from renewable raw materials
WO2010111570A1 (en) * 2009-03-27 2010-09-30 E. I. Du Pont De Nemours And Company Polyglycerol aldehydes
CN102361911A (en) * 2009-03-27 2012-02-22 阿克塔马克斯手术器材有限责任公司 Polyglycerol aldehydes
US8404779B2 (en) 2009-03-27 2013-03-26 Actamax Surgical Materials Llc Tissue adhesive and sealant comprising polyglycerol aldehyde
US8680200B2 (en) 2009-03-27 2014-03-25 Actamax Surgical Materials Llc Polyglycerol aldehydes
USRE46234E1 (en) 2009-03-27 2016-12-13 Actamax Surgical Materials, Llc Tissue adhesive and sealant comprising polyglycerol aldehyde
US9474916B2 (en) 2013-08-08 2016-10-25 Evonik Degussa Gmbh Carbamates from glycerine carbonate for pearlization

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