EP1718588A1 - Procede pour produire des diethers d'alkylene glycol - Google Patents

Procede pour produire des diethers d'alkylene glycol

Info

Publication number
EP1718588A1
EP1718588A1 EP05761400A EP05761400A EP1718588A1 EP 1718588 A1 EP1718588 A1 EP 1718588A1 EP 05761400 A EP05761400 A EP 05761400A EP 05761400 A EP05761400 A EP 05761400A EP 1718588 A1 EP1718588 A1 EP 1718588A1
Authority
EP
European Patent Office
Prior art keywords
microreactor
reaction
methyl
acid
alkylene glycol
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Withdrawn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
EP05761400A
Other languages
German (de)
English (en)
Inventor
Hieng Kim
Christian Wille
Klaus Forstinger
Achim Stankowiak
Gabriele Oberendfellner
Alexander Snell
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.)
Clariant Produkte Deutschland GmbH
Original Assignee
Clariant Produkte Deutschland GmbH
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 Clariant Produkte Deutschland GmbH filed Critical Clariant Produkte Deutschland GmbH
Publication of EP1718588A1 publication Critical patent/EP1718588A1/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Withdrawn legal-status Critical Current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
    • C07C41/02—Preparation of ethers from oxiranes

Definitions

  • the present invention relates to a process for the production of chain-shaped alkylene glycol diethers in the microreactor.
  • Alkylene glycol diethers have long been used as polar, inert solvents. Indirect processes such as the Williamson ether synthesis (K. Weissermel, HJ Arpe “Industrial Organic Chemistry”, 1998, page 179) or the hydrogenation of diglycol ether formal (DE-A-24 34 057) are used industrially or for their preparation described, as well as direct processes such as, for example, the insertion of alkylene oxide into a chain ether in the presence of Lewis acids such as BF 3 (US Pat. No. 4,146,736 and DE-A-26 40 505 in conjunction with DE-A-31 28 962) or SnCI 4 (DE-A-30 25 434).
  • Lewis acids such as BF 3 (US Pat. No. 4,146,736 and DE-A-26 40 505 in conjunction with DE-A-31 28 962) or SnCI 4 (DE-A-30 25 434).
  • microreactors In order to achieve a uniform product quality, the process parameters such as temperature, time and mixing must be checked. It is known from DD 246 257 A1 that miniaturized process engineering apparatuses can be used for chemical reactions. It is known to carry out certain chemical reactions in microreactors.
  • microreactors stands for micro and mini reactors, which differ due to the dimensions and structure of the microstructured reaction channels. Microreactors also include a combination of a static micromixer and a temperature-controlled retention zone connected to it (a continuous tubular reactor), e.g. understood a capillary.
  • Microreactors are constructed from stacks of structured plates and are described, for example, in the patent specification DE 39 26 466 C2.
  • the present invention was therefore based on the object of finding a process for producing chain-shaped alkylene glycol diethers in which the process parameters can be mastered well in order to achieve uniform product quality.
  • the process should also enable improved plant safety and simple, fast transfer from the laboratory scale to the technical scale.
  • the present invention relates to the use of a microreactor for the production of alkylene glycol diethers by a direct Lewis acid-catalyzed production process under pressure.
  • microreactor offers a higher level of safety (low molecular weight alkylene glycol diethers such as monoethylene glycol dimethyl ethers are toxic and carcinogenic) because the reaction volume in microreactors is particularly low compared to conventional batch processes.
  • the invention relates to a method for producing
  • Alkylene glycol diethers by reacting a linear or cyclic ether with an alkylene oxide in the presence of a Lewis acid, characterized in that the reaction is carried out continuously in a microreactor.
  • the linear or cyclic ethers, the alkylene oxide and the required Lewis acid are metered into the reactor in liquid form (if necessary under pressure).
  • the quantities are controlled, for example, via mass flow meters or a gravimetric metering control.
  • the reaction is carried out at a pressure of 0 to 30 bar (above atmospheric pressure), preferably at a pressure of 8 to 20 bar, and at a temperature of 0 ° C. to 200 ° C., preferably 20 ° C. to 150 ° C.
  • the reaction mixture with the resulting product is brought to normal pressure in a flash vessel and then worked up.
  • Suitable ethers which can be used as starting materials for the process according to the invention are various ethers with lower alkyl groups and in particular those of the general formula I:
  • R 1 is a Ci to C ⁇ 2 alkyl group
  • R 2 is a Ci to C ⁇ 2 alkyl group or a phenyl or benzyl group, or wherein R 1 and R 2 , including the oxygen atom, a ring with 5, 6 or 7 atoms form.
  • R 1 and R 2 are preferably independently of one another C 1 -C 4 -alkyl, in particular methyl or ethyl.
  • R 1 and R 2 form a ring, this corresponds to the formula where n is 2, 3 or 4.
  • a preferred cyclic compound is tetrahydrofuran.
  • R represents hydrogen, halogen, an alkyl group having 1 to 10 carbon atoms, a phenyl or a benzyl group.
  • alkylene oxides examples include ethylene oxide, propylene oxide, butylene oxide, epichlorohydrin, styrene oxide and the mixture of these compounds. Ethylene oxide and propylene oxide are particularly preferred.
  • R 2 Ci to Ci2-alkyl or a phenyl or benzyl group x is an integer from 1 to 6 y is an integer from 1 to 20.
  • R 1 and R 2 are preferably a methyl or ethyl group, in particular one Methyl group.
  • Lewis acids to be used in the process according to the invention can be very different in their composition and structure.
  • Lewis acids (individually or in combination) in the form of metal and non-metal halides such as, for example, BF 3 , AICI 3 , FeCI 3 , SnCI, PF 5 , SbF 5> , are preferably suitable; in the form of hydrogen acids, such as HBF 4 , HB0 2 ; in the form of heteropolyacids such as tungsten heteropolyacid; in the form of coordination complexes of metal and non-metal halides with organic compounds, such as haloalkylene, ethers, acid chlorides, acid esters or acid anhydrides.
  • trialkyloxonium salt complexes with identical or different alkyl groups analogous acylium salt complexes and unsaturated tertiary oxonium salts, the tertiary carboxonium salts.
  • Solvents can be used in the process according to the invention if they give advantages in the preparation of catalysts, for example to increase the solubility and / or to increase / decrease the viscosity and / or to dissipate heat of reaction.
  • inert solvents such as dichloromethane, nitromethane, benzene, toluene, acetone, ethyl acetate, or dioxane or active solvents such as methanol, ethanol, propanol, butanol, methyl glycol, methyl diglycol, methyl triglycol, or the target substances themselves such as mono-, di, tri , Tetra or polyalkylene glycol dimethyl ether.
  • alkylene glycol diethers can be produced in good yield in a continuous process in the microreactor, if appropriate in combination with further discontinuous process steps (e.g. production of starting material or catalyst mixtures, working up of the reaction mixture).
  • Microreactors such as are known from the prior art can be used, for example commercially available microreactors, such as, for example, that on Cytos TM based Selecto TM from Cellular Process Chemistry GmbH, Frankfurt am Main.
  • Microreactors with two or more reaction zones can also be used for the individual reaction steps.
  • the microreactor is made up of several stacked and interconnected platelets, on the surfaces of which there are micromechanically generated structures which, in their interaction, form reaction spaces in which chemical reactions take place.
  • the preferred microreactor is made of stainless steel; other materials such as glass, ceramics, silicon, plastics or other metals are also used.
  • a suitable microreactor is shown in the description and in FIG. 1 of DE-A-100 40 100.

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

L'invention concerne un procédé pour produire des diéthers d'alkylène glycol, ledit procédé consistant à faire réagir un éther linéaire ou cyclique avec un oxyde d'alkylène en présence d'un acide de Lewis. L'invention est caractérisée en ce que la réaction est effectuée en continu dans un microréacteur.
EP05761400A 2004-02-17 2005-02-08 Procede pour produire des diethers d'alkylene glycol Withdrawn EP1718588A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004007561A DE102004007561B3 (de) 2004-02-17 2004-02-17 Verfahren zur Herstellung von Alkylenglykoldiethern
PCT/EP2005/001236 WO2005087695A1 (fr) 2004-02-17 2005-02-08 Procede pour produire des diethers d'alkylene glycol

Publications (1)

Publication Number Publication Date
EP1718588A1 true EP1718588A1 (fr) 2006-11-08

Family

ID=34960602

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05761400A Withdrawn EP1718588A1 (fr) 2004-02-17 2005-02-08 Procede pour produire des diethers d'alkylene glycol

Country Status (5)

Country Link
US (1) US20070185353A1 (fr)
EP (1) EP1718588A1 (fr)
JP (1) JP2007522250A (fr)
DE (1) DE102004007561B3 (fr)
WO (1) WO2005087695A1 (fr)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2586971C (fr) 2004-11-12 2013-07-23 Velocys Inc. Procede utilisant la technologie de microcanal pour conduire une reaction d'alkylation ou d'acylation
DE102007057146A1 (de) 2007-11-28 2009-06-04 Evonik Goldschmidt Gmbh Verfahren zur Herstellung von Polyetheralkoholen mit DMC-Katalysatoren unter Verwendung von speziellen Additiven mit aromatischer Hydroxy-Funktionalisierung
DE102007057145A1 (de) 2007-11-28 2009-06-04 Evonik Goldschmidt Gmbh Verfahren zur Herstellung von Polyetheralkoholen mit DMC-Katalysatoren unter Verwendung von SiH-Gruppen tragenden Verbindungen als Additive
DE102008000360A1 (de) 2008-02-21 2009-08-27 Evonik Goldschmidt Gmbh Neue Alkoxysilylgruppen tragende Polyetheralkohole durch Alkoxylierung epoxidfunktioneller Alkoxysilane an Doppelmetallcyanid (DMC)-Katalysatoren, sowie Verfahren zu deren Herstellung
DE102008000903A1 (de) 2008-04-01 2009-10-08 Evonik Goldschmidt Gmbh Neue Organosiloxangruppen tragende Polyetheralkohole durch Alkoxylierung epoxidfunktioneller (Poly)Organosiloxane an Doppelmetallcyanid (DMC)-Katalysatoren, sowie Verfahren zu deren Herstellung
DE102008002713A1 (de) 2008-06-27 2009-12-31 Evonik Goldschmidt Gmbh Neue Polyethersiloxane enthaltende Alkoxylierungsprodukte durch direkte Alkoxylierung organomodifizierter alpha, omega-Dihydroxysiloxane an Doppelmetallcyanid (DMC)-Katalysatoren, sowie Verfahren zu deren Herstellung
DE102008043245A1 (de) 2008-10-29 2010-05-06 Evonik Goldschmidt Gmbh Siliconpolyether-Copolymersysteme sowie Verfahren zu deren Herstellung durch Alkoxylierungsreaktion
DE102008043343A1 (de) 2008-10-31 2010-05-06 Evonik Goldschmidt Gmbh Silikonpolyetherblock-Copolymere mit definierter Polydispersität im Polyoxyalkylenteil und deren Verwendung als Stabilisatoren zur Herstellung von Polyurethanschäumen
DE102009002371A1 (de) 2009-04-15 2010-10-21 Evonik Goldschmidt Gmbh Verfahren zur Herstellung von geruchlosen Polyetheralkoholen mittels DMC-Katalysatoren und deren Verwendung in kosmetischen und/oder dermatologischen Zubereitungen
DE102010003672A1 (de) 2010-04-07 2011-10-13 Evonik Goldschmidt Gmbh Herstellung und Verwendung von Metallsalzen von Alkyloxid- und/oder Arylalkyloxid-Oligomeren und -Polymeren mit Säureendgruppen bei der Herstellung von Polyurethansystemen
DE102010029235A1 (de) 2010-05-21 2011-11-24 Evonik Degussa Gmbh Hydrophile Polyisocyanate
DE102010039004A1 (de) 2010-08-06 2012-02-09 Evonik Goldschmidt Gmbh Silikoncopolymere mit seitenständigen über Allylglycidylether und verwandte Verbindungen angebundenen Alkylreisten und ihre Verwendung als Stabilisatoren zur Herstellug von Polyurethanweichschäumen
DE102010039140A1 (de) 2010-08-10 2012-02-16 Evonik Goldschmidt Gmbh Dispergiermittel und Verfahren zu deren Herstellung
DE102011076019A1 (de) 2011-05-18 2012-11-22 Evonik Goldschmidt Gmbh Alkoxylierungsprodukte und Verfahren zu ihrer Herstellung mittels DMC-Katalysatoren
DE102013208328A1 (de) 2013-05-07 2014-11-13 Evonik Industries Ag Polyoxyalkylene mit seitenständigen langkettigen Acyloxyresten und Verfahren zu ihrer Herstellung mittels DMC-Katalysatoren
DE102014209355A1 (de) 2014-05-16 2015-11-19 Evonik Degussa Gmbh Guanidinhaltige Polyoxyalkylene und Verfahren zur Herstellung
CN105582811B (zh) * 2014-11-16 2018-04-17 浙江创世雷博科技有限公司 一种用于硼同位素分离的原料净化方法

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2434057C2 (de) * 1974-07-16 1982-08-19 Hoechst Ag, 6000 Frankfurt Verfahren zur Herstellung von Glykoldimethyläthern
DE2640505C2 (de) * 1976-09-09 1978-08-31 Hoechst Ag, 6000 Frankfurt Verfahren zur Herstellung von Aethern
DE3025434C2 (de) * 1979-07-04 1982-09-16 Nisso Petrochemical Industry Co., Ltd., Tokyo Verfahren zur Herstellung von Alkylenglykoldiäthern
DE3128962A1 (de) * 1981-07-22 1983-02-10 Hoechst Ag, 6000 Frankfurt "verfahren zur herstellung von alkylenglykoldiethern
US4579982A (en) * 1984-03-28 1986-04-01 Union Carbide Corporation Preparation of monoalkylene glycols using two liquid phase reaction menstruum
US4760200A (en) * 1985-12-31 1988-07-26 Union Carbide Corporation Process for the production of alkylene glycols
DD246257A1 (de) * 1986-01-21 1987-06-03 Akad Wissenschaften Ddr Verfahrenstechnische mikroapparaturen und verfahren zu ihrer herstellung
DE3926466C2 (de) * 1989-08-10 1996-12-19 Christoph Dipl Ing Caesar Mikroreaktor zur Durchführung chemischer Reaktionen von zwei chemischen Stoffen mit starker Wärmetönung
US5811062A (en) * 1994-07-29 1998-09-22 Battelle Memorial Institute Microcomponent chemical process sheet architecture
DE10040100A1 (de) * 2000-08-16 2002-02-28 Clariant Gmbh Verfahren zur Herstellung von Azofarbmitteln in Mikroreaktoren
JP2003524033A (ja) * 2000-02-09 2003-08-12 クラリアント・インターナシヨナル・リミテツド ミクロリアクタ中でアゾ染料を製造する方法
EP1827678B1 (fr) * 2004-08-31 2012-07-18 Total Synthesis Ltd. Procede et appareil pour realiser des reactions chimiques a microechelle

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2005087695A1 *

Also Published As

Publication number Publication date
WO2005087695A1 (fr) 2005-09-22
DE102004007561B3 (de) 2005-10-13
US20070185353A1 (en) 2007-08-09
JP2007522250A (ja) 2007-08-09

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