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WO1999003581A1 - Procede de production d'un catalyseur a support - Google Patents

Procede de production d'un catalyseur a support Download PDF

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Publication number
WO1999003581A1
WO1999003581A1 PCT/EP1998/004058 EP9804058W WO9903581A1 WO 1999003581 A1 WO1999003581 A1 WO 1999003581A1 EP 9804058 W EP9804058 W EP 9804058W WO 9903581 A1 WO9903581 A1 WO 9903581A1
Authority
WO
WIPO (PCT)
Prior art keywords
support material
supported catalysts
preparation
alkyl
supported
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.)
Ceased
Application number
PCT/EP1998/004058
Other languages
German (de)
English (en)
Inventor
Rutger Anthony Van Santen
Hendrikus Cornelius Louis Abbenhuis
Simon Krijnen
Rob Willem Johan Maria Hanssen
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.)
Solvay GmbH
Original Assignee
Solvay 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 Solvay Deutschland GmbH filed Critical Solvay Deutschland GmbH
Priority to AU87311/98A priority Critical patent/AU8731198A/en
Publication of WO1999003581A1 publication Critical patent/WO1999003581A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/1616—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/1608—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes the ligands containing silicon
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • 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
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
    • B01J2231/72—Epoxidation
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/46—Titanium
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/48—Zirconium
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/49—Hafnium
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/50—Complexes comprising metals of Group V (VA or VB) as the central metal
    • B01J2531/56—Vanadium
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/50—Complexes comprising metals of Group V (VA or VB) as the central metal
    • B01J2531/57—Niobium
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/50—Complexes comprising metals of Group V (VA or VB) as the central metal
    • B01J2531/58—Tantalum
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
    • B01J2531/62—Chromium
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
    • B01J2531/64—Molybdenum
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
    • B01J2531/66—Tungsten
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/70—Complexes comprising metals of Group VII (VIIB) as the central metal
    • B01J2531/74—Rhenium

Definitions

  • the invention relates to a process for the preparation of a supported catalyst which contains silasesquioxane-metal complexes as catalytically active compounds, and to the use of these supported catalysts for the oxidation or epoxidation of unsaturated hydrocarbons or alcohols.
  • amorphous Ti0 2 -Si0 2 oxides can catalyze selective oxidations with organic hydroperoxides.
  • the object of the invention is to provide a heterogeneous catalyst based on silasesquioxane-metal complexes.
  • the catalyst should be characterized by a high level of economy. It should have a long service life, be thermally and air-stable and be easy to remove.
  • known crystalline or amorphous support materials based on SiO 2 with a pore diameter of 20 to 250 A, preferably 20 to 40 A, in particular 20 to 27 A, impregnated or impregnated with a silasesquioxane-metal complex solution.
  • silasesquioxane-metal complexes are understood to be the complexes which are obtained by reacting a metal compound with a silasesquioxane with defined denticity.
  • Halides, in particular chlorides, are used to prepare the complexes. or aryl compounds that do not contain a beta hydrogen atom, e.g. B. methyl, benzyl, neopentyl, xylyl, mesityl, neophile, adamantyl compounds, silyl, fluorenyl, idenyl, cyclopentadienyl compounds, the individual ligands by C 1 -C 4 - alkyl, C ⁇ -C ,, - alkylsilyl, alkoxy, aryl or arylsilyl groups can be substituted,
  • Oxides, imides, amides, alkoxides e.g. -OR, where R is hydrogen, -C jQ -alkyl, in particular methyl, ethyl, isopropyl, tert-butyl, aryl, in particular benzyl, phenyl, toluyl, naphthyl, xylyl, means
  • R is hydrogen, -C jQ -alkyl, in particular methyl, ethyl, isopropyl, tert-butyl, aryl, in particular benzyl, phenyl, toluyl, naphthyl, xylyl, means
  • their mixed compounds e.g. B.
  • SiMe 2 (CH 2 ) s CHACH 3 where A stands for OH, COOH, NH 2 , S0 3 -, COO "and s stands for 1 to 20, y stands for 2 and 3 and R 1 and R 3 can be functionalized by halogen or OH and
  • an organic solvent e.g. B. an alkylated aromatic hydrocarbon, preferably toluene, optionally in the presence of a basic compound, suspended with stirring at -80 ° C to 110 ° C.
  • an organic solvent e.g. B. an alkylated aromatic hydrocarbon, preferably toluene, optionally in the presence of a basic compound, suspended with stirring at -80 ° C to 110 ° C.
  • Pyridine is preferably used as the basic compound.
  • Metal compounds are understood to mean, in particular, compounds of titanium, zirconium, hafnium, chromium, tungsten, molybdenum, vanadium, niobium, tantalum, rhenium.
  • the by-products are separated by simple centrifugation.
  • M stands for the metals and Y for the above-mentioned radicals of the metal compound bonded to the metal, R 1 , B, n, m, q, r have the abovementioned meaning, R 2a is oxygen u 1 to 4 v 1 to 4 w 0 to 12, z. B. directly by adding acetonitrile and cleaned in a known manner, for. B. by recrystallization.
  • the metal complexes thus produced can, for. B. 4- or 6-fold coordinated metal complexes.
  • titanium complexes are prepared, wherein each titanium atom is 6-coordinate. This structural feature of the 6-fold coordination of all titanium atoms represents an important prerequisite for the hydrolysis resistance of the metal complexes and for their catalytic effectiveness.
  • silasesquioxane-titanium complexes e.g. B. [ 7 Si 7 0 12 ] -Ti ( ⁇ 5 -C 5 -H 5 ) used as a catalytic compound.
  • Amorphous support materials based on SiO 2 are to be understood as support material in the sense of the invention, which can be produced in a known manner by a sol-gel process and which are characterized by high porosity and uniform pore distribution.
  • Support material in the sense of the invention are also zeolitic support materials which are mesoporous and have a pore diameter of 20 to 100 A, e.g. B. MCM-41.
  • the carrier material is pure SiO 2 .
  • the carrier material in addition to Si0 2 also contains aluminum in oxidic form, for. B. 0.1 wt .-% aluminum or more.
  • carrier materials are used which have the following parameters.
  • the aluminum content of the support material is also important.
  • the Si / Al atomic ratio of MCM-41 can vary between 12 and 100, preferably 12 and 200.
  • the carrier material in the sense of the invention can have an aluminum content (in oxidic form) of at most 15% by weight, preferably from 0.2 to 5% by weight.
  • the carrier material is silylated before or after impregnation with the active component.
  • the support material is silylated before or after impregnation with the silasesquioxane-metal complex in order to adjust the hydrophobicity of the support material.
  • the silylation of the carrier material is carried out in a manner known per se by the silylating agent, for. B. dichlorodiphenylsilane or dichlorodimethylsilane is brought into contact with the carrier material.
  • the silylation is preferably carried out by refluxing.
  • organic solvents known per se are suitable as solvents for the impregnation or silylation.
  • Solvents in which the silasesquioxane-metal complexes used are soluble are particularly suitable for the impregnation.
  • Hexane, methylene dichloride or toluene are preferably used.
  • the silylation is preferably carried out in the presence of hexane. If appropriate, the supported catalyst can be dried after impregnation or silylation.
  • the supported catalyst produced according to the invention is characterized by a high level of economy. No leaching effect occurred in the observed test period.
  • the catalyst is thermally stable, air-stable and has a high abrasion resistance. It is easily separable from the reaction mixtures, e.g. B. by simple filtration. It was found that the catalyst had at least three reaction cycles, e.g. B. withstands an epoxidation of alkenes.
  • the supported catalyst produced according to the invention can be used both in powder form and as a lumpy shaped body.
  • the invention furthermore relates to the supported catalysts obtainable by the process according to the invention.
  • They comprise crystalline or amorphous support material based on SiO 2 with a pore diameter of 20 to 250 A, preferably 20 to 40 A, and silasesquioxane-metal complexes of the general formula II as a catalytically active compound.
  • the complexes of formula II are explained above.
  • the catalytically active compound (one can use a compound of the formula II, but if desired also more than one compound of the formula II) is then soaked or impregnated in the support material. Since the catalytically active compound is thus embedded in the pore system of the support material with mesopores, no leaching occurs.
  • a particularly preferred supported catalyst has a content of 0.2 to 15% by weight of aluminum, in particular 0.2 to 5% by weight of aluminum.
  • Aluminum-containing supported catalysts e.g. B. with more than 0.5 wt .-% aluminum are preferably silylated.
  • Supported catalysts with a content of aluminum in the support material of from 0.2% by weight are particularly advantageously silylated.
  • Preferred silylating agents are described above. In this way, supported catalysts with adjusted hydrophobicity of the support material can be obtained.
  • the supported catalysts prepared according to the invention are suitable for the oxidation or epoxidation of unsaturated hydrocarbons, preferably of alkenes or alcohols, in particular in the presence of tert.
  • unsaturated hydrocarbons preferably of alkenes or alcohols
  • tert preferably of alkenes or alcohols
  • TBHP butyl hydroperoxide
  • the catalyst is filtered off, washed three times with 20 ml of hexane each time and dried at 80 ° C. for 24 hours.
  • composition 1.2 mg Ti / g carrier Example 2;
  • 0.5 g of a supported catalyst impregnated according to Example 1 with an Si / Al ratio of 42 (atomic ratio) are refluxed for 72 hours with a solution of 70 ml of hexane and 2.5 g of dichlorodiphenylsilane.
  • the catalyst is filtered off, washed three times with 20 ml of hexane and acetone and dried at 80 ° C for 24 hours.
  • composition 1.2 mg Ti / g carrier
  • An amorphous carrier material based on Si0 2 which was produced by a sol-gel process, with a BET surface area of 759 m 2 / g, a total pore volume of 0.51 cm 3 / g and an aluminum oxide content of 2.7 wt .-% is impregnated as in Example 1 and silylated as in Example 2.
  • composition 1.2 mg Ti / g carrier

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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)
  • Catalysts (AREA)

Abstract

Selon l'invention, des catalyseurs à support sont obtenus par imprégnation ou imbibition d'un matériau support cristallin ou amorphe à base de SiO2, dont le diamètre des pores est compris entre 20 et 250 Å, avec des complexes métalliques silasesquioxane. Ces catalyseurs à support s'utilisent dans l'oxydation ou l'époxydation d'hydrocarbures insaturés ou d'alcools.
PCT/EP1998/004058 1997-07-16 1998-07-01 Procede de production d'un catalyseur a support Ceased WO1999003581A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU87311/98A AU8731198A (en) 1997-07-16 1998-07-01 Method for producing a supported catalyst

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1997130376 DE19730376A1 (de) 1997-07-16 1997-07-16 Verfahren zur Herstellung eines Trägerkatalysators
DE19730376.5 1997-07-16

Publications (1)

Publication Number Publication Date
WO1999003581A1 true WO1999003581A1 (fr) 1999-01-28

Family

ID=7835815

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/004058 Ceased WO1999003581A1 (fr) 1997-07-16 1998-07-01 Procede de production d'un catalyseur a support

Country Status (3)

Country Link
AU (1) AU8731198A (fr)
DE (1) DE19730376A1 (fr)
WO (1) WO1999003581A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7612143B2 (en) 1999-08-04 2009-11-03 Hybrid Plastics, Inc. Metallized nanostructured chemicals alloyed into polymers
US7820761B2 (en) 1999-08-04 2010-10-26 Hybrid Plastics, Inc. Metallized nanostructured chemicals as cure promoters
CN111715293A (zh) * 2014-07-18 2020-09-29 利安德化学技术有限公司 在负载型环氧化催化剂中用作活性组分的配合物

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19959525A1 (de) * 1999-12-09 2001-06-13 Bayer Ag Katalysatoren auf Basis Edelmetall- und Titan-haltiger, organisch-anorganisch Hybridmaterialien zur selektiven Oxidation von Kohlenwasserstoffen
DE10060775A1 (de) * 2000-12-07 2002-06-13 Creavis Tech & Innovation Gmbh Oligomere Silasesquioxane und Verfahren zur Herstellung von oligomeren Silasesquioxanen
US7125937B2 (en) * 2004-01-27 2006-10-24 Fina Technology, Inc. Polyorganosilsesquioxane supported metallocene catalysts

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997024344A1 (fr) * 1995-12-27 1997-07-10 Shell Internationale Research Maatschappij B.V. Preparation de composes epoxyde en utilisant un titanasilsesquioxane comme catalyseur
DE19715786A1 (de) * 1997-04-16 1998-10-22 Solvay Deutschland Verfahren zur Herstellung von Silasesquioxan-Metallkomplexen, neue Silasesquioxan-Metallkomplexe und deren Verwendung
WO1998046352A1 (fr) * 1997-04-16 1998-10-22 Solvay Deutschland Gmbh Procede pour la preparation de complexes metalliques de silasesquioxane, nouveaux complexes metalliques de silasesquioxane et leur utilisation

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997024344A1 (fr) * 1995-12-27 1997-07-10 Shell Internationale Research Maatschappij B.V. Preparation de composes epoxyde en utilisant un titanasilsesquioxane comme catalyseur
DE19715786A1 (de) * 1997-04-16 1998-10-22 Solvay Deutschland Verfahren zur Herstellung von Silasesquioxan-Metallkomplexen, neue Silasesquioxan-Metallkomplexe und deren Verwendung
WO1998046352A1 (fr) * 1997-04-16 1998-10-22 Solvay Deutschland Gmbh Procede pour la preparation de complexes metalliques de silasesquioxane, nouveaux complexes metalliques de silasesquioxane et leur utilisation

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7612143B2 (en) 1999-08-04 2009-11-03 Hybrid Plastics, Inc. Metallized nanostructured chemicals alloyed into polymers
US7820761B2 (en) 1999-08-04 2010-10-26 Hybrid Plastics, Inc. Metallized nanostructured chemicals as cure promoters
CN111715293A (zh) * 2014-07-18 2020-09-29 利安德化学技术有限公司 在负载型环氧化催化剂中用作活性组分的配合物

Also Published As

Publication number Publication date
DE19730376A1 (de) 1999-01-21
AU8731198A (en) 1999-02-10

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