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WO2000076989A2 - Procede pour faire reagir des composes organiques avec du peroxyde d'hydrogene - Google Patents

Procede pour faire reagir des composes organiques avec du peroxyde d'hydrogene Download PDF

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Publication number
WO2000076989A2
WO2000076989A2 PCT/EP2000/005319 EP0005319W WO0076989A2 WO 2000076989 A2 WO2000076989 A2 WO 2000076989A2 EP 0005319 W EP0005319 W EP 0005319W WO 0076989 A2 WO0076989 A2 WO 0076989A2
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WO
WIPO (PCT)
Prior art keywords
hydrogen peroxide
peroxide solution
ppm
organic compound
reaction
Prior art date
Application number
PCT/EP2000/005319
Other languages
German (de)
English (en)
Other versions
WO2000076989A3 (fr
Inventor
Joaquim Henrique Teles
Andreas Walch
Norbert Rieber
Gabrielle Iffland
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 AU56794/00A priority Critical patent/AU5679400A/en
Publication of WO2000076989A2 publication Critical patent/WO2000076989A2/fr
Publication of WO2000076989A3 publication Critical patent/WO2000076989A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B15/00—Peroxides; Peroxyhydrates; Peroxyacids or salts thereof; Superoxides; Ozonides
    • C01B15/01—Hydrogen peroxide
    • C01B15/013—Separation; Purification; Concentration
    • C01B15/0135—Purification by solid ion-exchangers or solid chelating agents
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B15/00—Peroxides; Peroxyhydrates; Peroxyacids or salts thereof; Superoxides; Ozonides
    • C01B15/01—Hydrogen peroxide
    • C01B15/013—Separation; Purification; Concentration
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B15/00—Peroxides; Peroxyhydrates; Peroxyacids or salts thereof; Superoxides; Ozonides
    • C01B15/01—Hydrogen peroxide
    • C01B15/022—Preparation from organic compounds
    • C01B15/023—Preparation from organic compounds by the alkyl-anthraquinone process
    • 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 invention relates to a process for reacting an organic compound with a hydrogen peroxide solution in the presence of a catalyst containing subgroup metal atoms, the amount of dissolved salts in the reaction mixture being reduced.
  • the invention further relates to methods for reducing the salt concentration in hydrogen peroxide solutions.
  • the invention further relates to an integrated method for producing a hydrogen peroxide solution based on a conventional anthraquinone method, which includes one or more steps for reducing the salt concentration.
  • epoxides can be prepared by reacting olefins and hydrogen peroxide in the presence of zeolite catalysts containing titanium atoms (see e.g. EP-A 0 100 1 19).
  • EP-A 0 230 949 also discloses that the neutralization of the catalyst with water-soluble basic substances can optionally be carried out before and / or during the epoxidation. It is stated here that 0.0001 to 0.1% by weight of such a neutralizing agent is added to the hydrogen peroxide feed in a continuous procedure.
  • the selectivity of the titanium silicalite-catalyzed olefin epoxidation can be increased by adding small amounts of non-basic salts, such as LiCl, NaNO 3 , K SO 4 and NH 4 H 2 PO 4 . It is stated that the concentration of non-basic salts in the liquid phase of the reaction zone should not be higher than 0.02M, whereas concentrations below 0.0000 IM have little or no effect on the epoxidation selectivity.
  • the primary object of the present invention was to provide a method for increasing the selectivity in the reaction of an organic compound with hydrogen peroxide, which does not have the disadvantages of the prior art.
  • the present invention relates to a process for reacting an organic compound with a hydrogen peroxide solution, characterized in that the concentration of dissolved anions and cations in the hydrogen peroxide solution used is in each case less than 100 ppm.
  • the invention relates in particular to a process in which the reaction of an organic compound takes place in the presence of a catalyst containing secondary group metal atoms.
  • An aqueous hydrogen peroxide solution is particularly preferably used in the process according to the invention.
  • the concentration of the aqueous hydrogen peroxide solution preferably used can be between 1 and 70% by weight, a concentration between 5 and 60% by weight is preferred, a concentration between 10 and 50% by weight is particularly preferred.
  • Hydroxylations such as the hydroxylation of mono-, bi- or polycyclic aromatics to mono-, di- or higher substituted hydroxy aromatics, for example the conversion of phenol and HO 2 to hydroquinone;
  • oxime formation from ketones in the presence of H 2 O and ammonia for example the preparation of cyclohexanone oxime from cyclohexanone;
  • Olefins are preferably reacted in the process according to the invention.
  • 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 contain additional functional groups such as halogen atoms, carboxyl groups, carboxylic ester functions, hydroxyl groups, ether bridges, sulfide bridges, carbonyl functions, cyano groups or nitro groups.
  • alkenes are mentioned as examples of such organic compounds with at least one C-C double bond:
  • Mixtures of the olefins mentioned can also be epoxidized by the process according to the invention.
  • Alkenes containing 2 to 8 carbon atoms are preferably used in the process according to the invention. Ethene, propene and butene are particularly preferred. The process according to the invention is particularly suitable for the epoxidation of propene to propylene oxide.
  • Catalysts are preferably used which comprise a porous oxidic material such as a zeolite.
  • Catalysts are preferably used which comprise a zeolite containing titanium, vanadium, chromium, niobium or zirconium as the porous oxidic material.
  • Zeolites containing titanium, vanadium, chromium, niobium, and zirconium with a pentasil zeolite structure in particular the types with X-ray assignment to ABW, ACO, AEI, AEL, AEN, AET, AFG, AFI, AFN, AFO, AFR, AFS, AFT, AFX, AFY, AHT, ANA, APC, APD, AST, ATN, ATO, ATS , ATT, ATV, AWO, AWW, BEA, BIK, BOG, BPH, BRE, CAN, CAS, CFI, CGF, CGS, CHA, CHI, CLO , CON, CZP, DAC, DDR, DFO, DFT, DOH, DON, EAB, EDI, EMT, EPI, ERI, ESV, EUO, FAU, FER -, GIS, GME, GOO, HEU, IFR, ISV, ITE,
  • Ti zeolites with an MFI, MEL or MFI / MEL mixed structure are to be regarded as particularly preferred for the process according to the invention.
  • the Ti-containing zeolite catalysts which are generally referred to as "TS-1", “TS-2”, “TS-3”, and Ti zeolites with a framework structure isomorphous to zeolite are also particularly preferred call.
  • a heterogeneous catalyst comprising the titanium-containing silicalite TS-1 is particularly preferably used in the process according to the invention.
  • porous oxidic material per se as the catalyst.
  • a shaped body as the catalyst which is the porous oxide Material includes. All processes according to the prior art can be used to produce the shaped body, starting from the porous oxidic material.
  • noble metals in the form of suitable noble metal components can be applied to the catalyst material.
  • This method is preferably used to produce oxidation catalysts based on titanium or vanadium silicates with a zeolite structure, it being possible to obtain catalysts which contain from 0.01 to 30% by weight of one or more noble metals from the group ruthenium, rhodium, Palladium, osmium, iridium, platinum, rhenium, gold and silver.
  • Such catalysts are described, for example, in DE-A 196 23 609.6, which is hereby fully incorporated by reference into the context of the present application with respect to the catalysts described therein.
  • the moldings can be assembled. All methods of comminution are conceivable, for example by splitting or breaking the shaped bodies, as are other chemical treatments.
  • the catalysts used can contain up to about 60% by weight of binder, based on the total mass of the catalyst.
  • the process according to the invention can be carried out with all customary reaction procedures and in all customary reactor types, for example in a suspension procedure or in a fixed bed arrangement. You can work continuously or discontinuously.
  • the reaction according to the invention is preferably carried out in a fixed bed apparatus.
  • the process according to the invention is advantageously carried out at a pressure of 1 to 100 bar.
  • suitable solvents are water, alcohols, e.g. Methanol, ethanol, iso-propanol or tert-butanol, or mixtures thereof. Mixtures of methanol and water are preferred as solvents, and methanol is particularly preferably used.
  • the process according to the invention is generally carried out at temperatures from 0 ° C. to 100 ° C., preferably at 20 to 90 ° C. and particularly preferably at 25 to 60 ° C.
  • a hydrogen peroxide solution suitable for use in the process according to the invention which contains only small amounts of dissolved salts, can be obtained in various ways. For example, you can reduce the salt concentrations in a finished, such as a commercial hydrogen peroxide solution.
  • the present invention also relates to processes for reducing the salt concentration in a hydrogen peroxide solution, and in particular to processes which are characterized in that the hydrogen peroxide solution is treated with an ion exchanger.
  • cation exchangers and anion exchangers can be used in the process according to the invention.
  • ion exchanger If only one type of ion exchanger is used, the use of at least one anion exchanger is preferred and that of a weakly basic anion exchanger is particularly preferred. If several ion exchangers are used, they can be used simultaneously or in succession. Sequential treatment with at least one cation exchanger is preferred, followed by treatment with at least one anion exchanger. A weakly basic anion exchanger is preferred as the anion exchanger.
  • ion exchangers known to the person skilled in the art can be used in the context of the present invention, for example organic ion exchangers, for example based on polystyrene, or inorganic ion exchangers, for example hydrotalcites and other phyllosilicates which can contain exchangeable carbonate, hydrogen carbonate or hydroxide groups.
  • Examples of the weakly basic anion exchangers which are particularly preferred in the context of the present invention are polystyrene resins with tertiary amine groups, for example the commercially available anion exchangers Lewatit MP62 and Lewatit MP 63 (Bayer AG) as well as Dowex MWA / 1 and Dowex AMW-500 (Dow Chemical).
  • the use of strongly basic ion exchangers for example polystyrene resins containing quaternary ammonium groups (with hydroxide counterions), is also conceivable. Examples include the commercially available exchangers Lewatit OC-1950 (Bayer AG) and Dowex 1, Dowex 2, Dowex 11, Dowex 21K and Dowex 550A (Dow Chemical).
  • the conditions in the treatment of the hydrogen peroxide solution with the ion exchanger or the ion exchangers of choice should be chosen so that the hydrogen peroxide solution obtained after this treatment contains the smallest possible amount of anions and cations.
  • the concentration of dissolved anions or cations is preferably in the
  • the present invention further relates to the use of a hydrogen peroxide solution, the concentration of dissolved salts of which has been reduced by means of a method according to the invention, in the method according to the invention for reacting an organic compound.
  • a hydrogen peroxide solution which is suitable for use in the process according to the invention and which contains only small amounts of dissolved salts can also be obtained by reducing the salt concentration already during the preparation of the hydrogen peroxide solution.
  • the present invention also relates to an integrated process for the production of hydrogen peroxide based on a conventional anthraquinone process, characterized in that it comprises the following steps: extraction of the (a) working solution with water and (b) treatment with one or more ion exchangers.
  • the water used for the extraction of the working solution preferably has a phosphate, nitrate and sodium ion content which ensures an extraction which is harmless from a safety point of view, ie generally in each case about 100 ppm to a maximum of about 150 ppm.
  • the anthraquinone process by means of which practically the entire amount of the hydrogen peroxide produced worldwide (> 2 million t / a) is produced, is based on the catalytic hydrogenation of an anthraquinone compound to the corresponding anthraquinroquinone compound, subsequent reaction thereof with oxygen to form hydrogen peroxide and subsequent separation of the hydrogen peroxide formed by extraction.
  • the catalytic cycle is closed by renewed hydrogenation of the re-formed anthraquinone compound.
  • the anthraquinone compounds used are usually dissolved in a mixture of several organic solvents.
  • the resulting solution is called a working solution.
  • this working solution is usually continuously passed through the stages of the process described above.
  • the present invention further relates to the use of a hydrogen peroxide solution produced by means of the integrated method according to the invention in the method according to the invention for the reaction of an organic compound.
  • Table 1 shows an example of typical phosphate, nitrate and sodium ion contents 6 of various commercially available aqueous hydrogen peroxide solutions:
  • Table 1 Overview of the phosphate, nitrate and sodium ion content of some commercially available aqueous hydrogen peroxide solutions
  • the hydrogen peroxide solution from Example 2 was passed at 10-20 ° C. at an empty tube speed of approx. 5 m / h over a column with a height of 80 cm and a diameter of 2 cm (corresponding to a load of 1700 g / h) , which was filled with a weakly basic anion exchanger (Lewatit MP62, Bayer AG). After this treatment, the hydrogen peroxide solution contained only 10-20 ppm phosphate and 10-16 ppm nitrate, the sodium ion and hydrogen peroxide concentrations were unchanged within the measurement accuracy.
  • Example 6 Comparative example
  • Example 4 The procedure was analogous to Example 4, with the difference that a commercial aqueous 20% hydrogen peroxide solution was used which contained 100 ppm phosphate, 30 ppm nitrate and 20 ppm sodium ions.
  • the feed amounts were 16.1 g / h (propene), 33 g / h (hydrogen peroxide solution) and 79.8 g / h (methanol).
  • Example 6 The procedure was analogous to Example 6, with the difference that the commercial aqueous 20% hydrogen peroxide solution initially at 10 to 20 ° C with an empty tube speed of about 1.3 m / h over a column with a height of 160 cm and a diameter of 2 cm (corresponding to a load of 450 g / h), which was filled with a weakly basic anion exchanger (Lewatit MP62, Bayer AG).
  • the hydrogen peroxide solution contained only 10-20 ppm phosphate and 10-16 ppm nitrate, the sodium ion and hydrogen peroxide concentrations were unchanged within the measuring accuracy.

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

Abstract

La présente invention concerne un procédé pour faire réagir des composés organiques avec une solution de peroxyde d'hydrogène, qui se caractérise en ce que la concentration en anions et cations dissous dans la solution de peroxyde d'hydrogène utilisée est chaque fois inférieure à 100 ppm. L'invention concerne en outre un procédé de réduction de la concentration en sel dans des solutions de peroxyde d'hydrogène, l'utilisation des solutions de peroxyde d'hydrogène ainsi obtenues pour faire réagir un composé organique, ainsi qu'un procédé intégré de production d'une solution de peroxyde d'hydrogène fondé sur un procédé classique faisant appel à de l'anthraquinone, lequel comporte au moins une étape pour la réduction de la concentration en sel.
PCT/EP2000/005319 1999-06-11 2000-06-08 Procede pour faire reagir des composes organiques avec du peroxyde d'hydrogene WO2000076989A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU56794/00A AU5679400A (en) 1999-06-11 2000-06-08 Method for reacting organic compounds with hydrogen peroxide

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1999126725 DE19926725A1 (de) 1999-06-11 1999-06-11 Verfahren zur Umsetzung organischer Verbindungen mit Wasserstoffperoxid
DE19926725.1 1999-06-11

Publications (2)

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WO2000076989A2 true WO2000076989A2 (fr) 2000-12-21
WO2000076989A3 WO2000076989A3 (fr) 2001-07-12

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Country Status (3)

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AU (1) AU5679400A (fr)
DE (1) DE19926725A1 (fr)
WO (1) WO2000076989A2 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1403219A1 (fr) * 2002-09-30 2004-03-31 Degussa AG Nouvelles solutions aqueuses de péroxydes d'hydrogène
US6838572B2 (en) 2002-09-30 2005-01-04 Degussa Ag Process for the epoxidation of olefins
US7169945B2 (en) 2002-11-26 2007-01-30 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
US8481765B2 (en) 2008-03-17 2013-07-09 Momentive Specialty Chemicals Inc. Method for the production of epichlorohydrin
CN106061891A (zh) * 2014-01-10 2016-10-26 阿肯马法国公司 用于植物物质脱木素的过氧化氢组合物及其用途
US10100024B2 (en) 2014-07-29 2018-10-16 Evonik Degussa Gmbh Process for the epoxidation of an olefin
US10125108B2 (en) 2015-04-28 2018-11-13 Evonik Degussa Gmbh Process for the epoxidation of propene
EP3052439B1 (fr) 2013-10-02 2019-08-07 Solvay SA Procédé de fabrication d'une solution aqueuse purifiée de peroxyde d'hydrogène

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19954055A1 (de) * 1999-11-10 2001-05-17 Basf Ag Vorrichtung und Verfahren zur Entfernung von Salzen aus Wasserstoffperoxid-Lösungen

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US4999179A (en) * 1988-12-26 1991-03-12 Mitsubishi Gas Chemical Company, Inc. Method for purifying impure aqueous hydrogen peroxide solution
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IT1247960B (it) * 1991-06-03 1995-01-05 Erba Carlo Spa Procedimento di purificazione del perossido di idrogeno
FI924124L (fi) * 1991-09-19 1993-03-20 Ube Industries Foerfarande foer rening av vaeteperoxidvattenloesning
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US5646314A (en) * 1994-11-16 1997-07-08 Arco Chemical Technology, L.P. Process for titanium silicalite-catalyzed epoxidation
WO1996034827A1 (fr) * 1995-05-04 1996-11-07 Chevron U.S.A. Inc. Zeolithe a structure mel contenant du titane en phase pure
AU6103696A (en) * 1995-06-05 1996-12-24 Startec Ventures, Inc. On-site generation of ultra-high-purity buffered hf for semi conductor processing
JP3797390B2 (ja) * 1995-11-15 2006-07-19 三菱瓦斯化学株式会社 精製過酸化水素の製造方法
EP0812836B1 (fr) * 1996-06-14 2005-03-16 Sumitomo Chemical Company, Limited Préparation de produits époxidés d'oléfines
FR2754529B1 (fr) * 1996-10-15 1998-11-06 Chemoxal Sa Procede de purification de peroxyde d'hydrogene
ES2178825T3 (es) * 1998-03-26 2003-01-01 Repsol Quimica Sa Procedimiento de eposidacion de compuestos olefinicos con peroxido de hidrogeno.

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7981391B2 (en) 2002-09-30 2011-07-19 Evonik Degussa Gmbh Aqueous hydrogen peroxide solutions and method of making same
WO2004028962A1 (fr) * 2002-09-30 2004-04-08 Degussa Ag Nouvelles solutions de peroxyde d'hydrogene aqueuses
US6838572B2 (en) 2002-09-30 2005-01-04 Degussa Ag Process for the epoxidation of olefins
EP1403219A1 (fr) * 2002-09-30 2004-03-31 Degussa AG Nouvelles solutions aqueuses de péroxydes d'hydrogène
US7722847B2 (en) 2002-09-30 2010-05-25 Evonik Degussa Gmbh Aqueous hydrogen peroxide solutions and method of making same
KR100990351B1 (ko) * 2002-09-30 2010-10-29 에보닉 데구사 게엠베하 신규의 과산화수소 수용액
US7169945B2 (en) 2002-11-26 2007-01-30 Degussa Ag Process for the epoxidation of olefins
US8481765B2 (en) 2008-03-17 2013-07-09 Momentive Specialty Chemicals Inc. Method for the production of epichlorohydrin
EP3052439B1 (fr) 2013-10-02 2019-08-07 Solvay SA Procédé de fabrication d'une solution aqueuse purifiée de peroxyde d'hydrogène
EP3052439B2 (fr) † 2013-10-02 2022-06-22 Solvay SA Procédé de fabrication d'une solution aqueuse purifiée de peroxyde d'hydrogène
CN106061891A (zh) * 2014-01-10 2016-10-26 阿肯马法国公司 用于植物物质脱木素的过氧化氢组合物及其用途
CN106061891B (zh) * 2014-01-10 2019-02-19 阿肯马法国公司 用于植物物质脱木素的过氧化氢组合物及其用途
US10100024B2 (en) 2014-07-29 2018-10-16 Evonik Degussa Gmbh Process for the epoxidation of an olefin
US10125108B2 (en) 2015-04-28 2018-11-13 Evonik Degussa Gmbh Process for the epoxidation of propene

Also Published As

Publication number Publication date
WO2000076989A3 (fr) 2001-07-12
DE19926725A1 (de) 2000-12-14
AU5679400A (en) 2001-01-02

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