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WO1997047613A1 - Procede de production d'epoxydes a partir d'olefines et de peroxyde d'hydrogene ou d'hydroperoxydes a l'aide d'un catalyseur d'oxydation zeolithique - Google Patents

Procede de production d'epoxydes a partir d'olefines et de peroxyde d'hydrogene ou d'hydroperoxydes a l'aide d'un catalyseur d'oxydation zeolithique Download PDF

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Publication number
WO1997047613A1
WO1997047613A1 PCT/EP1997/002815 EP9702815W WO9747613A1 WO 1997047613 A1 WO1997047613 A1 WO 1997047613A1 EP 9702815 W EP9702815 W EP 9702815W WO 9747613 A1 WO9747613 A1 WO 9747613A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydrogen peroxide
hydroperoxides
titanium
sources
oxidation catalyst
Prior art date
Application number
PCT/EP1997/002815
Other languages
German (de)
English (en)
Inventor
Ulrich Müller
Georg Heinrich Grosch
Bernhard Hauer
Michael Schulz
Norbert Rieber
Original Assignee
Basf Aktiengesellschaft
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 Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to AU30931/97A priority Critical patent/AU3093197A/en
Priority to CA002256395A priority patent/CA2256395A1/fr
Priority to EP97925967A priority patent/EP0906298A1/fr
Priority to BR9709703A priority patent/BR9709703A/pt
Priority to JP10501127A priority patent/JP2000511912A/ja
Publication of WO1997047613A1 publication Critical patent/WO1997047613A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/19—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic hydroperoxides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/89—Silicates, aluminosilicates or borosilicates of titanium, zirconium or hafnium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids

Definitions

  • the present invention relates to an improved process for the production of epoxides from olefins and hydrogen peroxide or hydroperoxides using an oxidation catalyst based on titanium or vanadium silicates with a zeolite structure.
  • the epoxidation of ethylene, propene, allyl chloride, 2-butene, 1-octene, 1-tridecene, mesityl oxide, isoprene, 0 cyclooctene and cyclohexene by means of dilute aqueous hydrogen peroxide in the presence of a titanium silicalite in an autoclave ven carried out.
  • the hydrogen peroxide concentration in the reaction mixture can be reduced by up to 10% by weight.
  • the object of the present invention was therefore to provide a simple, efficient and, in particular, economical epoxidation process for olefins which no longer has the disadvantages of the prior art.
  • organic hydroperoxides of the formula R-O-O-H used as customary oxidizing agents for such epoxidations can be used as hydroperoxides, where R generally represents an organic radical having 1 to 30 C atoms. Cumene and diisopropylbenzene hydroperoxide are of particular interest.
  • the hydrogen peroxide sources used for the epoxidation according to the invention are aqueous hydrogen peroxide solutions, in particular technical (ie not purified) hydrogen peroxide solutions with a content of 0.1 to 10% by weight, in particular 0.15 up to 5% by weight, especially 0.2 to
  • Such technical hydrogen peroxide sources are particularly suitable as extraction solutions containing hydrogen peroxide from an anthraquinone working solution for the production of hydrogen peroxide.
  • Such technical hydrogen peroxide sources are furthermore suitable hydrogen peroxide-containing streams or residues, for example vapors or bottoms, from a hydrogen peroxide distillation, these streams or residues mostly not having been further concentrated in their H 2 0 2 content.
  • Such technical hydrogen peroxide sources are also particularly suitable extraction solutions containing fermenter broths or enzyme mixtures containing hydrogen peroxide, ie from naturally occurring or biotechnologically accessible sources.
  • the oxidation catalysts based on titanium or vanadium silicates with a zeolite structure are known from the prior art.
  • zeolites are crystalline alumino-silicates with ordered channel and cage structures, the pore openings of which are in the range of micropores which are smaller than 0.9 nm.
  • the network of such zeolites is made up of Si0 4 and A10 4 tetrahedra, which are connected via common oxygen bridges.
  • Zeolites are now also known which do not contain aluminum and in which titanium (Ti) is used instead of Si (IV) in the silicate lattice. These titanium zeolites, in particular those with an MFI-type crystal structure, and possibilities for their production are described, for example in EP-A 311 983 or EP-A 405 978.
  • silicon and titanium such materials can also contain additional elements such as aluminum, Contain zirconium, tin, iron, cobalt, nickel, gallium, boron or small amounts of fluorine.
  • the titanium of the zeolite can be partially or completely replaced by vanadium.
  • the molar ratio of titanium and / or vanadium to the sum of silicon plus titanium and / or vanadium is generally in the range from 0.01: 1 to 0.1: 1.
  • Titanium zeolites with an MFI structure are known to have a certain pattern when determining their X-ray diffraction images and also a framework vibration band in the
  • Infrared range can be identified at about 960 cm "1 and thus differ from alkali metal titanates or crystalline and amorphous Ti0 2 phases.
  • the titanium and also vanadium zeolites mentioned are prepared by adding an aqueous mixture of an SiO 2 source, a titanium or vanadium source such as titanium dioxide or a corresponding vanadium oxide and a nitrogenous organic base ( "Template compound”), for example tetrapropylammonium hydroxide, optionally with the addition of alkali metal compounds, in a pressure vessel under elevated temperature over a period of several hours or a few days, the crystalline product being formed. This is filtered off, washed, dried and fired at elevated temperature to remove the organic nitrogen base.
  • the titanium or the vanadium is at least partially in varying proportions within the zeolite framework with four, five or six-fold coordination.
  • a repeated washing treatment with sulfuric acid hydrogen peroxide solution can follow, after which the titanium or vanadium zeolite powder must be dried and fired again; this can be followed by treatment with alkali metal compounds in order to convert the zeolite from the H form into the cation form.
  • Preferred titanium or vanadium zeolites are those with a pentasil zeolite structure, in particular the types with X-ray assignment to the BEA, MOR, TON, MTW, FER, MFI, MEL or MFI / MEL mixed structure. Zeolites of this type are described, for example, in W.M. Meier and D.H. Olson, "Atlas of Zeolite Structure Types", Butterworths, 2nd Ed., London 1987. Titanium-containing zeolites with the structure of ZSM-48, ZSM-12, ferrierite or ⁇ -zeolite and mordenite are also conceivable for the present invention.
  • the process according to the invention for the preparation of epoxides can be carried out using all customary reaction procedures and in all customary reactor types, for example using the suspension procedure or in a fixed bed arrangement. You can work continuously or discontinuously.
  • the epoxidation according to the invention is expediently carried out in the liquid phase in water alone or in a mixture of water and water-miscible organic solvents.
  • organic solvents are particularly suitable alcohols such as methanol, ethanol, iso-propanol, tert. -Butanol or mixtures thereof. If such organic solvents are used in a mixture with water, their proportion of the total mixture is usually 5 to 95% by volume, in particular 30 to 85% by volume.
  • the epoxidation according to the invention is generally carried out at a temperature of from -20 to 70 ° C., in particular from -5 to 50 ° C., and at a pressure of 1 to 10 bar.
  • the olefin used can be any organic compound which contains at least one ethylenically unsaturated double bond. It can be aliphatic, aromatic or cycloaliphatic in nature, it can consist of a linear or a branched structure.
  • the olefin preferably contains 2 to 30 carbon atoms. There may be more than one ethylenically unsaturated double bond, for example in dienes or trienes.
  • the olefin can additionally contain functional groups such as halogen atoms, carboxyl groups, carboxylic ester functions, hydroxyl groups, ether bridges, sulfide bridges, carbonyl functions, cyano groups, nitro groups or amino groups.
  • Typical examples of such olefins are ethylene, propene, 5 1-butene, ice and trans-2-butene, 1, 3-butadiene, pentene, isoprene, hexene, octene, nonene, decene, undecene, dodecene, cyclopentene, cyclohexene, Dicyclopentadiene, methylene cyclopropane, vinyl cyclohexane, vinyl cyclohexene, allyl chloride, acrylic acid, methacrylic acid, crotonic acid, vinyl acetic acid, allyl alcohol, alkyl acrylates, alkyl
  • the process according to the invention is particularly suitable for the epoxidation of propene to propylene oxide.
  • the present invention it is possible to successfully epoxidize olefins far below the hydrogen peroxide concentration known in the prior art by means of titanium or vanadium silicalites. Because of the low concentration of hydrogen peroxide in the system, there are no longer any safety problems. Furthermore, hydrogen peroxide solutions can be used without disturbing stabilizers, which are necessary at high concentrations.
  • the process according to the invention has the advantage that inexpensive technical hydrogen peroxide sources can be used as feedstock; the impurities present in such sources surprisingly do not interfere with the epoxidation according to the invention.
  • the sealed autoclave (anchor stirrer, 200 rpm) was brought to a reaction temperature of 175 ° C. at a heating rate of 3 ° / min. The reaction was complete after 92 hours.
  • the cooled reaction mixture (white suspension) was centrifuged off and washed neutral with water several times. The solid obtained was dried at 110 ° C. in the course of 24 hours (weight 149 g).
  • the pure white product had a Ti content of 1.5% by weight and a residual alkali content below 100 ppm.
  • the yield on Si0 2 used was 97%.
  • the crystallites had a size of 0.05 to 0.25 ⁇ m and the product showed a typical band at approx. 960 cm 1 in the IR.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Epoxy Compounds (AREA)

Abstract

L'invention concerne un procédé de production d'époxydes à partir d'oléfines et de peroxyde d'hydrogène ou d'hydroperoxydes en phase liquide à l'aide d'un catalyseur d'oxydation à base de silicalites de titane ou de vanadium à structure zéolithique. Ce procédé se caractérise en ce que la concentration du peroxyde d'hydrogène ou des hydroperoxydes dans le mélange réactionnel lors de la réaction se situe dans une plage comprise entre 0,05 et moins de 1 % en poids.
PCT/EP1997/002815 1996-06-13 1997-05-30 Procede de production d'epoxydes a partir d'olefines et de peroxyde d'hydrogene ou d'hydroperoxydes a l'aide d'un catalyseur d'oxydation zeolithique WO1997047613A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AU30931/97A AU3093197A (en) 1996-06-13 1997-05-30 Process for producing epoxides from olefines and hydrogen peroxide or hydroperoxides using a zeolithic oxidation catalyst
CA002256395A CA2256395A1 (fr) 1996-06-13 1997-05-30 Procede de production d'epoxydes a partir d'olefines et de peroxyde d'hydrogene ou d'hydroperoxydes a l'aide d'un catalyseur d'oxydation zeolithique
EP97925967A EP0906298A1 (fr) 1996-06-13 1997-05-30 Procede de production d'epoxydes a partir d'olefines et de peroxyde d'hydrogene ou d'hydroperoxydes a l'aide d'un catalyseur d'oxydation zeolithique
BR9709703A BR9709703A (pt) 1996-06-13 1997-05-30 Processos para preparar epóxidos e óxidos de propileno
JP10501127A JP2000511912A (ja) 1996-06-13 1997-05-30 ゼオライト酸化触媒を使用してオレフィンおよび過酸化水素またはヒドロペルオキシドからエポキシドを製造する方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19623608A DE19623608A1 (de) 1996-06-13 1996-06-13 Verfahren zur Herstellung von Epoxiden aus Olefinen und Wasserstoffperoxid oder Hydroperoxiden
DE19623608.8 1996-06-13

Publications (1)

Publication Number Publication Date
WO1997047613A1 true WO1997047613A1 (fr) 1997-12-18

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Country Status (8)

Country Link
EP (1) EP0906298A1 (fr)
JP (1) JP2000511912A (fr)
KR (1) KR20000016334A (fr)
AU (1) AU3093197A (fr)
BR (1) BR9709703A (fr)
CA (1) CA2256395A1 (fr)
DE (1) DE19623608A1 (fr)
WO (1) WO1997047613A1 (fr)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6596883B2 (en) 2001-08-23 2003-07-22 Degussa Ag Process for the epoxidation of olefins
US6596881B2 (en) 2001-06-13 2003-07-22 Degussa Ag Process for the epoxidation of olefins
US6600055B2 (en) 2001-06-13 2003-07-29 Degussa Ag Process for the epoxidation of olefins
US6608219B2 (en) 2001-06-13 2003-08-19 Degussa Ag Process for the epoxidation of olefins
US6610865B2 (en) 2001-08-15 2003-08-26 Degussa Ag Process for the epoxidation of olefins
US6617465B2 (en) 2001-01-08 2003-09-09 Degussa Ag Process for the epoxidation of olefins
US6624319B2 (en) 2000-02-07 2003-09-23 Degussa Ag Process for the epoxidation of olefins
US6646141B2 (en) 2000-02-07 2003-11-11 Degussa Ag Process for the epoxidation of olefins
US6670492B2 (en) 2000-02-07 2003-12-30 Degussa Ag Process for the expoxidation of olefins
US6720436B2 (en) 2002-03-18 2004-04-13 Degussa Ag Process for the epoxidation of olefins
US6749668B2 (en) 2001-06-18 2004-06-15 Degussa Ag Process for the recovery of combustible components of a gas stream
US6838572B2 (en) 2002-09-30 2005-01-04 Degussa Ag Process for the epoxidation of olefins
US7141683B2 (en) 2002-05-02 2006-11-28 Degussa Ag Process for the epoxidation of olefins
US7169945B2 (en) 2002-11-26 2007-01-30 Degussa Ag Process for the epoxidation of olefins
CN100516020C (zh) * 2001-09-26 2009-07-22 艾米斯菲尔技术有限公司 通过二羧化物中间体制备苯氧基链烷酸、链烯酸和炔酸及其盐的方法
US7722847B2 (en) 2002-09-30 2010-05-25 Evonik Degussa Gmbh Aqueous hydrogen peroxide solutions and method of making same

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19857137A1 (de) 1998-12-11 2000-06-15 Bayer Ag Integriertes Verfahren zur Herstellung von Epoxiden aus Olefinen
DE10135296A1 (de) * 2001-07-19 2003-01-30 Basf Ag Verfahren zur Herstellung von Propylenoxid
US6562987B1 (en) * 2002-02-28 2003-05-13 Arco Chemical Technology, L.P. Method for highly exothermic epoxidation reactions
WO2017089074A1 (fr) * 2015-11-26 2017-06-01 Evonik Degussa Gmbh Procédé d'époxydation d'une oléfine
HUE055229T2 (hu) 2017-04-24 2021-11-29 Basf Se Propén visszanyerése oldószer/víz eleggyel történõ átmosással
CN114082441A (zh) * 2021-11-23 2022-02-25 江苏科技大学 一种mfi分子筛及其制备方法与应用

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EP0405978A1 (fr) * 1989-06-29 1991-01-02 Engelhard Corporation Tamis moléculaires à grands pores et leur utilisation comme catalyseurs et comme échangeurs d'ions
EP0568336A2 (fr) * 1992-04-30 1993-11-03 ARCO Chemical Technology, L.P. Procédé pour l'epoxidation d'oléfines avec des catalyseurs de type silicate riches en titan
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EP0405978A1 (fr) * 1989-06-29 1991-01-02 Engelhard Corporation Tamis moléculaires à grands pores et leur utilisation comme catalyseurs et comme échangeurs d'ions
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WO1996002323A1 (fr) * 1994-07-20 1996-02-01 Basf Aktiengesellschaft Catalyseur d'oxydation, son procede de fabrication et procede d'oxydation utilisant ce catalyseur

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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6670492B2 (en) 2000-02-07 2003-12-30 Degussa Ag Process for the expoxidation of olefins
US6624319B2 (en) 2000-02-07 2003-09-23 Degussa Ag Process for the epoxidation of olefins
US6646141B2 (en) 2000-02-07 2003-11-11 Degussa Ag Process for the epoxidation of olefins
US6617465B2 (en) 2001-01-08 2003-09-09 Degussa Ag Process for the epoxidation of olefins
US6596881B2 (en) 2001-06-13 2003-07-22 Degussa Ag Process for the epoxidation of olefins
US6600055B2 (en) 2001-06-13 2003-07-29 Degussa Ag Process for the epoxidation of olefins
US6608219B2 (en) 2001-06-13 2003-08-19 Degussa Ag Process for the epoxidation of olefins
US6749668B2 (en) 2001-06-18 2004-06-15 Degussa Ag Process for the recovery of combustible components of a gas stream
US6610865B2 (en) 2001-08-15 2003-08-26 Degussa Ag Process for the epoxidation of olefins
US6596883B2 (en) 2001-08-23 2003-07-22 Degussa Ag Process for the epoxidation of olefins
CN100516020C (zh) * 2001-09-26 2009-07-22 艾米斯菲尔技术有限公司 通过二羧化物中间体制备苯氧基链烷酸、链烯酸和炔酸及其盐的方法
US6720436B2 (en) 2002-03-18 2004-04-13 Degussa Ag Process for the epoxidation of olefins
US7141683B2 (en) 2002-05-02 2006-11-28 Degussa Ag Process for the epoxidation of olefins
US6838572B2 (en) 2002-09-30 2005-01-04 Degussa Ag Process for the epoxidation of olefins
US7722847B2 (en) 2002-09-30 2010-05-25 Evonik Degussa Gmbh Aqueous hydrogen peroxide solutions and method of making same
US7981391B2 (en) 2002-09-30 2011-07-19 Evonik Degussa Gmbh Aqueous hydrogen peroxide solutions and method of making same
US7169945B2 (en) 2002-11-26 2007-01-30 Degussa Ag Process for the epoxidation of olefins

Also Published As

Publication number Publication date
KR20000016334A (ko) 2000-03-25
CA2256395A1 (fr) 1997-12-18
BR9709703A (pt) 1999-08-10
DE19623608A1 (de) 1997-12-18
EP0906298A1 (fr) 1999-04-07
AU3093197A (en) 1998-01-07
JP2000511912A (ja) 2000-09-12

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