DE4222183A1 - Process for the preparation of polyalkyl ethers - Google Patents
Process for the preparation of polyalkyl ethersInfo
- Publication number
- DE4222183A1 DE4222183A1 DE19924222183 DE4222183A DE4222183A1 DE 4222183 A1 DE4222183 A1 DE 4222183A1 DE 19924222183 DE19924222183 DE 19924222183 DE 4222183 A DE4222183 A DE 4222183A DE 4222183 A1 DE4222183 A1 DE 4222183A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- catalysts
- carbon atoms
- olefins
- group
- 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- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
- C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
-
- 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
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
Abstract
Description
Die Erfindung betrifft ein Verfahren zur Herstellung von Polyolalkylethern durch sauer katalysierte Umsetzung von Verbindungen, die mindestens zwei Hydroxylgruppen aufweisen, mit kurzkettigen Olefinen.The invention relates to a method for producing Polyolalkyl ethers by acid catalyzed reaction of Compounds which have at least two hydroxyl groups, with short chain olefins.
Polyolalkylether, wie beispielsweise Glycerin- oder Trimethy lolpropanether, stellen wichtige Rohstoffe für die Herstel lung von Netzmitteln [US 2 932 670], Emulgatoren [DE 11 00 035 A1] oder Kalkseifendispergatoren [US 3 350 460] dar.Polyolalkyl ethers, such as glycerol or trimethyl lolpropane ether, are important raw materials for the manufac wetting agents [US 2 932 670], emulsifiers [DE 11 00 035 A1] or lime soap dispersants [US 3,350,460].
Während die Herstellung langkettiger Produkte üblicherweise über den Weg der WILLIAMSON′schen Ethersynthese erfolgt, sind Verfahren zur Herstellung kurzkettiger Species mit erhebli chen Schwierigkeiten belastet.While producing long chain products usually via the path of WILLIAMSON’s ether synthesis Process for the production of short-chain species with erhebli Chen difficulties.
Klassische Methoden zur Herstellung von Dialkylethern gehen von Alkoholen aus, die in Gegenwart von konzentrierter Schwe felsäure unter drastischen Bedingungen umgesetzt werden. Die selektive Herstellung von gemischten Dialkylethern ist auf diese Weise nicht möglich; zudem werden durch Eliminierung leicht Olefine als unerwünschte Nebenprodukte gebildet [Orga nikum, VEB Verlag der Wissenschaften, 15. Aufl., Berlin, 1977, S. 244f].Classic methods for the production of dialkyl ethers go from alcohols in the presence of concentrated sweat rock acid can be implemented under drastic conditions. The selective production of mixed dialkyl ethers is on not possible this way; also through elimination easily olefins formed as undesirable by-products [Orga nikum, VEB Publishing House of Sciences, 15th edition, Berlin, 1977, pp. 244f].
Von Takana et al. ist aus Tetrahedr. Lett., 29, 1823 (1988) ein Verfahren zur Herstellung von Glycerin-tert.Butylether bekannt, bei dem man Glycerinacetal mit dem selbstentzündli chen Trimethylaluminium umsetzt. Dishong et al. beschreiben in J. Am. Chem. Soc. 105, 586 (1983) eine zweistufige Synthese ausgehend von tert.Butanol und dem hochgiftigen Epichlor hydrin. Montanari und Tundo berichten schließlich in J. Org. Chem. 47, 1298 (1982) über die Herstellung von Glycerin- tert.Butylether durch Umsetzung des nur sehr schwer zugäng lichen tert.Butylglycidylethers mit Ameisensäure.By Takana et al. is from Tetrahedr. Lett., 29, 1823 (1988) a process for the preparation of glycerol tert-butyl ether known in which one glycerin acetal with the auto-inflammatory Chen trimethyl aluminum. Dishong et al. describe in J. Am. Chem. Soc. 105, 586 (1983) a two-step synthesis based on tert-butanol and the highly toxic epichlor hydrine. Montanari and Tundo finally report in J. Org. Chem. 47, 1298 (1982) on the production of glycerol tert-Butyl ether due to the implementation of the very difficult to access Lichen tert-butylglycidyl ether with formic acid.
Die Aufgabe der Erfindung bestand somit darin, ein verbesser tes Verfahren zur Herstellung von Polyolalkylethern zur Ver fügung zu stellen, das frei von den geschilderten Nachtei len ist.The object of the invention was therefore to improve Process for the preparation of polyol alkyl ethers for ver to provide that free of the described nightlife len is.
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Polyolalkylethern, bei dem man Polyhydroxyverbindungen, ausgewählt aus der Gruppe, die vonThe invention relates to a method for producing of polyol alkyl ethers, in which polyhydroxy compounds, selected from the group by
- a) Alkylenglycolen,a) alkylene glycols,
- b) Glycerin,b) glycerol,
- c) Oligoglycerinen,c) oligoglycerols,
- d) Trimethylolpropan,d) trimethylolpropane,
- e) Pentaerythrit,e) pentaerythritol,
- f) 1,12-Dodecandiol undf) 1,12-dodecanediol and
- g) Sorbitg) sorbitol
gebildet wird, in Gegenwart von sauren Katalysatoren bei Tem peraturen von 50 bis 120°C und Drücken von 5 bis 25 bar mit Olefinen der Formel (I) umsetzt,is formed in the presence of acidic catalysts at Tem temperatures from 50 to 120 ° C and pressures from 5 to 25 bar with Reacting olefins of the formula (I),
in der R1 für einen linearen oder verzweigten Alkylrest mit 1 bis 6 Kohlenstoffatomen und R2 für Wasserstoff oder ebenfalls einen Alkylrest mit 1 bis 6 Kohlenstoffatomen steht.in which R 1 represents a linear or branched alkyl radical having 1 to 6 carbon atoms and R 2 represents hydrogen or likewise an alkyl radical having 1 to 6 carbon atoms.
Überraschenderweise wurde gefunden, daß sich Polyhydroxyver bindungen mit kurzkettigen α-Olefinen in Gegenwart schwach saurer Katalysatoren unter milden Reaktionsbeding ungen und in hohen Ausbeuten verethern lassen.Surprisingly, it was found that polyhydroxyver bonds with short-chain α-olefins in the presence weakly acidic catalysts under mild reaction conditions and etherified in high yields.
Unter Alkylenglycolen sind in diesem Zusammenhang Ethylen glycol, Propylenglycol und deren höhere Homologen mit einem durchschnittlichen Kondensationsgrad von 2 bis 12 zu verste hen. In this context, alkylene glycols are ethylene glycol, propylene glycol and their higher homologues with one to understand average degree of condensation from 2 to 12 hen.
Oligoglycerine, die im Sinne des erfindungsgemäßen Verfahrens als Polyhydroxyverbindungen in Betracht kommen, stellen Ei genkondensationsprodukte des Glycerins dar und können eben falls einen durchschnittlichen Kondensationsgrad von 2 bis 5 aufweisen.Oligoglycerols that are used in the process of the invention Suitable polyhydroxy compounds are egg gene condensation products of glycerol and can if an average degree of condensation of 2 to 5 exhibit.
Typische Beispiele für kurzkettige Olefine, die im Sinne des erfindungsgemäßen Verfahrens eingesetzt werden können, sind Propen sowie die isomeren Butene, Pentene, Hexene, Heptene, Octene und insbesondere Isobuten.Typical examples of short-chain olefins, which in the sense of process according to the invention can be used Propene and the isomeric butenes, pentenes, hexenes, heptenes, Octenes and especially isobutene.
Das molare Einsatzverhältnis von Polyhydroxyverbindung und Olefin kann dabei 1 : 1 bis 1 : 10 betragen. Als optimal hat es sich erwiesen, die Reaktionspartner in einem solchen Ver hältnis einzusetzen, daß auf jeweils ein Mol Hydroxylgruppen in der Polyhydroxyverbindung 1,1 bis 2 Mol Olefin entfällt.The molar ratio of polyhydroxy compound and The olefin can be 1: 1 to 1:10. As optimal it has been shown that the reactants in such a ver ratio use that to one mole of hydroxyl groups 1.1 to 2 mol of olefin are omitted in the polyhydroxy compound.
Die sauren Katalysatoren können im Reaktionsgemisch löslich oder unlöslich sein. Typische Beispiele für homogene, lös liche Katalysatoren sind p-Toluolsulfonsäure, Sulfoessig säure, Sulfobernsteinsäure, Sulfotriacetin und Dodecylbenzol sulfonsäure.The acidic catalysts can be soluble in the reaction mixture or be insoluble. Typical examples of homogeneous, soluble Liche catalysts are p-toluenesulfonic acid, sulfoacetic acid acid, sulfosuccinic acid, sulfotriacetin and dodecylbenzene sulfonic acid.
Typische Beispiele für unlösliche Katalysatoren sind saure
Ionenaustauscher wie etwa Amberlyst® 15 oder Dowex®
50W×2. Des weiteren kommen als heterogene Katalysatoren Zeo
lithe in Betracht, die natürlicher oder synthetischer Her
kunft sein können. Typische Beispiele sind die natürlich
vorkommenden Mineralien Clinoptilolith, Erionit oder Chaba
sit. Bevorzugt sind jedoch synthetische Zeolithe, beispiels
weise
Zeolith X Na86 [(AlO2)86(SiO2)106] · 264 H2O
Zeolith Y Na56 [(AlO2)56(SiO2)136] · 250 H2O
Zeolith L K9 [(AlO2)9(SiO2)27] · 22 H2O
Mordenit Na8 [(AlO2)8(SiO2)40] · 24 H2O
und insbesondere
Zeolith A Na12 [(AlO2)12(SiO2)12] · 27 H2O.Typical examples of insoluble catalysts are acidic ion exchangers such as Amberlyst® 15 or Dowex® 50W × 2. Further suitable heterogeneous catalysts are zeolites, which can be of natural or synthetic origin. Typical examples are the naturally occurring minerals clinoptilolite, erionite or chaba sit. However, synthetic zeolites are preferred, for example
Zeolite X Na 86 [(AlO 2 ) 86 (SiO 2 ) 106 ] · 264 H 2 O
Zeolite Y Na 56 [(AlO 2 ) 56 (SiO 2 ) 136 ] · 250 H 2 O
Zeolite LK 9 [(AlO 2 ) 9 (SiO 2 ) 27 ] · 22 H 2 O
Mordenite Na 8 [(AlO 2 ) 8 (SiO 2 ) 40 ] · 24 H 2 O
and in particular zeolite A Na 12 [(AlO 2 ) 12 (SiO 2 ) 12 ] · 27 H 2 O.
Die Einsatzmenge der sauren Katalysatoren kann dabei 0,1 bis 3, vorzugsweise 0,5 bis 2 Gew.-% - bezogen auf Polyhydroxy verbindung - betragen.The amount of acid catalysts used can be 0.1 to 3, preferably 0.5 to 2 wt .-% - based on polyhydroxy connection - amount.
Die Umsetzung kann unter milden Reaktionsbedingungen, d. h. bei Temperaturen von 50 bis 120, vorzugsweise 70 bis 90°C und Drücken von 5 bis 25, vorzugsweise 10 bis 15 bar innerhalb von 10 bis 25 h durchgeführt werden. Falls gewünscht, kann das rohe Umsetzungsprodukt anschließend destillativ gereinigt werden, wobei der Einsatz von Kurzweg-, Fallfilm- oder Dünn schichtverdampfern bevorzugt ist.The reaction can be carried out under mild reaction conditions, e.g. H. at temperatures of 50 to 120, preferably 70 to 90 ° C and Pressures from 5 to 25, preferably 10 to 15 bar within from 10 to 25 hours. If desired, can the crude reaction product is then purified by distillation be, the use of short path, falling film or thin layer evaporators is preferred.
Die nach dem erfindungsgemäßen Verfahren erhältlichen Polyolalkylether können als Lösungsmittel bzw. Lösungsver mittler, beispielsweise in Reinigungsmitteln, Farben und Lacken sowie als Treibstoffadditive zur Verbesserung der Klopffestigkeit von Ottomotorenbenzin eingesetzt werden. Those obtainable by the process according to the invention Polyolalkyl ethers can be used as solvents or solvents medium, for example in cleaning agents, paints and Paints and as fuel additives to improve the Knock resistance of gasoline petrol can be used.
Die folgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern, ohne ihn darauf einzuschränken.The following examples are intended to be the subject of the invention explain in more detail without restricting it.
In einem 1-l-Autoklaven wurden 98 g (1 mol) Glycerin und 760 mg (2 mmol) p-Toluolsulfonsäure vorgelegt und bei einer Tem peratur von 90°C und einem Druck von 10 bar mit 268 g (4,8 mol) Isobuten umgesetzt. Nach einer Reaktionszeit von 1 h wurde der Reaktor abgekühlt und entspannt. Es wurden 216 g Glycerin-tert.Butylether erhalten, in dem noch geringe Mengen gelöstes Isobuten enthalten waren.98 g (1 mol) of glycerol and 760 were in a 1-liter autoclave mg (2 mmol) p-toluenesulfonic acid submitted and at a tem temperature of 90 ° C and a pressure of 10 bar with 268 g (4.8 mol) implemented isobutene. After a reaction time of 1 h the reactor was cooled and let down. There were 216 g Get glycerol tert-butyl ether, in which still small amounts dissolved isobutene were included.
Das Rohprodukt wurde in eine Kurzwegdestillationsapparatur überführt. Bei einer Manteltemperatur von 200°C und einem verminderten Druck von 0,001 mbar wurden 164,8 g eines klaren Destillats und 44,5 g gelbgefärbten Sumpfproduktes erhalten. Die Zusammensetzung der Fraktionen ist Tab. 1 zu entnehmen.The crude product was in a short path distillation apparatus transferred. At a jacket temperature of 200 ° C and one reduced pressure of 0.001 mbar, 164.8 g of a clear Distillate and 44.5 g of yellow-colored bottom product obtained. The composition of the fractions is shown in Table 1.
Beispiel 1 wurde unter Einsatz von 1 g saurem Ionenaustau scher (Amberlyst®, Fa. Fluka) wiederholt, der nach Abschluß der Reaktion abfiltriert wurde. Die Zusammensetzung des Gly cerin-tert.Butylethers nach der Destillation ist in Tab. 2 zusammengefaßt:Example 1 was carried out using 1 g of acidic ion exchange shear (Amberlyst®, Fa. Fluka) repeated after completion the reaction was filtered off. The composition of the Gly cerin-tert-butyl ether after the distillation is in Tab. 2 summarized:
Beispiel 1 wurden unter Einsatz von 120 g (1 mol) Trimethy lolpropan und 1 g Sulfobernsteinsäure wiederholt. Die Zusam mensetzung des Trimethylolpropan-tert.Butylethers nach der Destillation ist in Tab. 3 zusammengefaßt:Example 1 was made using 120 g (1 mol) of trimethyl lolpropane and 1 g of sulfosuccinic acid repeated. The Together Preparation of the trimethylolpropane tert-butyl ether after the Distillation is summarized in Tab. 3:
Beispiel 1 wurden unter Einsatz von 136 g (1 mol) Pentaery thrit, 336 g (6 mol) Isobuten und 1,5 g Dodecylbenzolsul fonsäure wiederholt. Die Zusammensetzung des Pentaerythrit- tert.Butylethers nach der Destillation ist in Tab. 4 zusam mengefaßt:Example 1 was made using 136 g (1 mol) of pentaery thritol, 336 g (6 mol) of isobutene and 1.5 g of dodecylbenzenesul fonic repeated. The composition of the pentaerythritol tert-Butyl ether after the distillation is together in Tab. 4 quantified:
Claims (7)
- a) Alkylenglycolen,
- b) Glycerin,
- c) Oligoglycerinen,
- d) Trimethylolpropan,
- e) Pentaerythrit,
- f) 1,12-Dodecandiol und
- g) Sorbit
- a) alkylene glycols,
- b) glycerol,
- c) oligoglycerols,
- d) trimethylolpropane,
- e) pentaerythritol,
- f) 1,12-dodecanediol and
- g) sorbitol
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19924222183 DE4222183A1 (en) | 1992-07-06 | 1992-07-06 | Process for the preparation of polyalkyl ethers |
PCT/EP1993/001643 WO1994001389A1 (en) | 1992-07-06 | 1993-06-28 | Method of preparing polyol alkyl ethers |
EP93915718A EP0650470A1 (en) | 1992-07-06 | 1993-06-28 | Method of preparing polyol alkyl ethers |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19924222183 DE4222183A1 (en) | 1992-07-06 | 1992-07-06 | Process for the preparation of polyalkyl ethers |
Publications (1)
Publication Number | Publication Date |
---|---|
DE4222183A1 true DE4222183A1 (en) | 1994-01-13 |
Family
ID=6462603
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19924222183 Withdrawn DE4222183A1 (en) | 1992-07-06 | 1992-07-06 | Process for the preparation of polyalkyl ethers |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0650470A1 (en) |
DE (1) | DE4222183A1 (en) |
WO (1) | WO1994001389A1 (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5476971A (en) * | 1995-01-13 | 1995-12-19 | Arco Chemical Technology, L.P. | Glycerine ditertiary butyl ether preparation |
EP0747339A1 (en) * | 1995-06-08 | 1996-12-11 | Nippon Shokubai Co., Ltd. | Process for production of (poly)alkylene glycol monoalkyl ether |
US5731476A (en) * | 1995-01-13 | 1998-03-24 | Arco Chemical Technology, L.P. | Poly ether preparation |
US6417408B2 (en) * | 1996-12-06 | 2002-07-09 | Nippon Shokubai Co., Ltd. | Production process for (poly)alkylene glycol monoalkyl ether |
WO2005010131A1 (en) | 2003-06-24 | 2005-02-03 | Michiel Arjaan Kousemaker | Method for producing an oxygen-containing compound used as fuel additive, in particular in diesel fuels, gasoline and rapeseed methyl ester |
WO2006106124A1 (en) * | 2005-04-07 | 2006-10-12 | Basf Aktiengesellschaft | Production of (co)surfactants by reacting polyols with olefins |
WO2018055065A1 (en) | 2016-09-21 | 2018-03-29 | Cepsa S.A.U. | Solketal-ethers, production method and uses thereof |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5308365A (en) * | 1993-08-31 | 1994-05-03 | Arco Chemical Technology, L.P. | Diesel fuel |
DE69416077T2 (en) * | 1993-10-15 | 1999-07-15 | Fina Research | Process for the preparation of glycerin ethers |
DE4445635A1 (en) * | 1994-12-21 | 1996-06-27 | Veba Oel Ag | Process for the preparation of polyol alkyl ethers |
DE19738072A1 (en) * | 1997-09-01 | 1999-03-04 | Huels Chemische Werke Ag | Process for the preparation of cyclopropanecarboxylic acid esters of lower alcohols |
US6217589B1 (en) | 1999-10-27 | 2001-04-17 | Scimed Life Systems, Inc. | Retrieval device made of precursor alloy cable and method of manufacturing |
WO2007112100A2 (en) * | 2006-03-24 | 2007-10-04 | The University Of Utah Research Foundation | Highly fluorinated oils and surfactants and methods of making and using same |
US20090240086A1 (en) * | 2008-03-18 | 2009-09-24 | Barsa Edward A | Preparation of glycerol tert-butyl ethers |
NL1036154C (en) * | 2008-11-05 | 2010-05-06 | Criss Cross Technology B V | A motor fuel additive with enhanced properties, and processes for the production thereof. |
CN115703699A (en) * | 2021-08-06 | 2023-02-17 | 深圳有为技术控股集团有限公司 | Novel tertiary butyl ether substituted polyhydric alcohol and acrylate type compound thereof |
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Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5476971A (en) * | 1995-01-13 | 1995-12-19 | Arco Chemical Technology, L.P. | Glycerine ditertiary butyl ether preparation |
US5731476A (en) * | 1995-01-13 | 1998-03-24 | Arco Chemical Technology, L.P. | Poly ether preparation |
EP0747339A1 (en) * | 1995-06-08 | 1996-12-11 | Nippon Shokubai Co., Ltd. | Process for production of (poly)alkylene glycol monoalkyl ether |
US5741948A (en) * | 1995-06-08 | 1998-04-21 | Nippon Shokubai Co., Ltd. | Process for production of (poly) alkylene glycol monoalkyl ether |
AU702870B2 (en) * | 1995-06-08 | 1999-03-11 | Nippon Shokubai Co., Ltd. | Process for production of (poly)alkylene glycol monoalkyl ether |
US6417408B2 (en) * | 1996-12-06 | 2002-07-09 | Nippon Shokubai Co., Ltd. | Production process for (poly)alkylene glycol monoalkyl ether |
WO2005010131A1 (en) | 2003-06-24 | 2005-02-03 | Michiel Arjaan Kousemaker | Method for producing an oxygen-containing compound used as fuel additive, in particular in diesel fuels, gasoline and rapeseed methyl ester |
EP2204434A1 (en) | 2003-06-24 | 2010-07-07 | Biovalue Holding BV | Process for making an oxygenate as an additive in fuels, particularly in diesel fuels, gasoline and rapeseed methyl ester |
WO2006106124A1 (en) * | 2005-04-07 | 2006-10-12 | Basf Aktiengesellschaft | Production of (co)surfactants by reacting polyols with olefins |
US7807615B2 (en) | 2005-04-07 | 2010-10-05 | Basf Aktiengesellschaft | Production of (co)surfactants by reacting polyols with olefins |
JP4778552B2 (en) * | 2005-04-07 | 2011-09-21 | ビーエーエスエフ ソシエタス・ヨーロピア | Production of (co) surfactant by reaction of polyol and olefin |
WO2018055065A1 (en) | 2016-09-21 | 2018-03-29 | Cepsa S.A.U. | Solketal-ethers, production method and uses thereof |
Also Published As
Publication number | Publication date |
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EP0650470A1 (en) | 1995-05-03 |
WO1994001389A1 (en) | 1994-01-20 |
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