EP1718588A1 - Verfahren zur herstellung von alkylenglykoldiethern - Google Patents
Verfahren zur herstellung von alkylenglykoldiethernInfo
- 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- Withdrawn
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
Description
Claims
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 (de) | 2004-02-17 | 2005-02-08 | Verfahren zur herstellung von alkylenglykoldiethern |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1718588A1 true EP1718588A1 (de) | 2006-11-08 |
Family
ID=34960602
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP05761400A Withdrawn EP1718588A1 (de) | 2004-02-17 | 2005-02-08 | Verfahren zur herstellung von alkylenglykoldiethern |
Country Status (5)
Country | Link |
---|---|
US (1) | US20070185353A1 (de) |
EP (1) | EP1718588A1 (de) |
JP (1) | JP2007522250A (de) |
DE (1) | DE102004007561B3 (de) |
WO (1) | WO2005087695A1 (de) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006053345A1 (en) | 2004-11-12 | 2006-05-18 | Velocys Inc. | Process using microchannel technology for conducting alkylation or acylation reaction |
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)
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 |
CN1175053C (zh) * | 2000-02-09 | 2004-11-10 | 克拉里安特国际有限公司 | 在微型反应器中制备偶氮着色剂的方法 |
EP1827678B1 (de) * | 2004-08-31 | 2012-07-18 | Total Synthesis Ltd. | Verfahren und vorrichtung zur durchführung von chemischen reaktionen im mikromassstab |
-
2004
- 2004-02-17 DE DE102004007561A patent/DE102004007561B3/de not_active Expired - Fee Related
-
2005
- 2005-02-08 US US10/590,187 patent/US20070185353A1/en not_active Abandoned
- 2005-02-08 EP EP05761400A patent/EP1718588A1/de not_active Withdrawn
- 2005-02-08 WO PCT/EP2005/001236 patent/WO2005087695A1/de not_active Application Discontinuation
- 2005-02-08 JP JP2006553488A patent/JP2007522250A/ja not_active Withdrawn
Non-Patent Citations (1)
Title |
---|
See references of WO2005087695A1 * |
Also Published As
Publication number | Publication date |
---|---|
US20070185353A1 (en) | 2007-08-09 |
JP2007522250A (ja) | 2007-08-09 |
WO2005087695A1 (de) | 2005-09-22 |
DE102004007561B3 (de) | 2005-10-13 |
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RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: KIM, HIENG Inventor name: OBERENDFELLNER, GABRIELE Inventor name: SNELL, ALEXANDER Inventor name: STANKOWIAK, ACHIM Inventor name: WILLE, CHRISTIAN Inventor name: FORSTINGER, KLAUS |
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Effective date: 20070503 |