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WO2000067902A1 - Catalyseurs stables et leurs procedes de fabrication et d'utilisation - Google Patents

Catalyseurs stables et leurs procedes de fabrication et d'utilisation Download PDF

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Publication number
WO2000067902A1
WO2000067902A1 PCT/NL2000/000286 NL0000286W WO0067902A1 WO 2000067902 A1 WO2000067902 A1 WO 2000067902A1 NL 0000286 W NL0000286 W NL 0000286W WO 0067902 A1 WO0067902 A1 WO 0067902A1
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WO
WIPO (PCT)
Prior art keywords
support material
metal
palladium
group
catalyst
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/NL2000/000286
Other languages
English (en)
Inventor
Candida Milone
Leonardus Lefferts
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.)
Koninklijke DSM NV
Original Assignee
DSM NV
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 DSM NV filed Critical DSM NV
Priority to AU46251/00A priority Critical patent/AU4625100A/en
Publication of WO2000067902A1 publication Critical patent/WO2000067902A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/58—Platinum group metals with alkali- or alkaline earth metals

Definitions

  • stable catalysts include their activity lifetime and their selectivity to the desired product.
  • a short activity lifetime i.e., high deactivation rate, means high frequency of interruption of the process to regenerate or replace the catalyst which, of course, increases operating times and costs.
  • Transition metal catalysts which are in widespread use by the petroleum and petrochemical industry, are particularly prone to deterioration during prolonged operation. Many attempts have been made to overcome this problem by trying to extend the activity lifetime of such catalysts. For example, palladium-containing supported catalysts and their use in the hydrogenation of phenol to cyclohexanone are described in German Patent Specification No. 2,045,882, and British Patent Specification No.
  • German Patent Specification No. 2,752,291 also describes the hydrogenation of phenol to give cyclohexanone.
  • catalysts consisting of carbon or charcoal particles coated with palladium and having an (inner) surface area of 100 to 2,000 m 2 /g, and a phenol containing a small amount of alkali compounds are employed.
  • Figure 3 is a graph reporting the catalytic activity of comparative catalysts tested under integral conditions .
  • group 1 or 2 metals may be mentioned individually by way of example: Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, and Ba . Of these, Na, K and Cs are preferred, with Na being particularly preferred.
  • salts and/or complexes of palladium which may be useful include: Na 2 [PdCl] 4 , PdCl 2 , PdBr 2 , Pdl 2 , H 2 PdCl 4 , K 2 [PdCl 6 ] , Pd(CH 3 COO) 2 , Pd(acac) 3 , Pd(N0 3 ) 2 , PdS0 4 and [Pd (NH 3 ) 2 ] Cl 2 , with
  • the supported material can be dried and calcined in accordance with the conditions herein discussed with respect to the drying and calcining steps in the pre- treatment stage.
  • the conditions and preferred ranges discussed herein are applicable to the respective steps for the palladium treatment stage, it should be appreciated that each of these steps are independent and as such may employ the same or, typically, different conditions than those employed in the corresponding step.
  • the use of phenols of the formula (I) is preferred to the use of phenols of the formula (II) .
  • the hydrogenation process according to the invention is preferably carried out using catalysts which can be obtained by the measures described hereinabove.
  • the products leaving the reactor are generally cooled, and the hydrogenated phenols are separated off in a liquid or solid form. They can, if appropriate, be purified further by customary methods, for example by distillation.
  • the excess of hydrogen which is generally present can be recycled to the reactor, it being preferable to discharge a small proportion.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

La présente invention concerne des catalyseurs stables d'un point de vue réactif, et leur préparation, et des procédés réactionnels utilisant ces catalyseurs. Ces catalyseurs stables sont utiles dans les réactions d'hydrogénation, en particulier dans l'hydrogénation de phénols afin de produire la cyclohexanone correspondante. La présente invention concerne également un procédé de formation d'un catalyseur à support palladium, ladite matière de support dopée par un métal par imprégnation de la matière de support à un groupe (1) ou (2) à du bicarbonate métal (solution); (séchage de la matière de support imprégnée de bicarbonate et) calcination de la matière de support traité au bicarbonate afin de former un groupe (1) ou (2) une matière de support dopée par un métal; le groupe (1) ou (2) la matière de support dopée par un métal est traitée au palladium par imprégnation complémentaire de la matière de support au moyen d'une solution de sel de palladium, par séchage et calcination. L'invention porte également sur une grande diversité de procédés catalytiques comme, par exemple, l'hydrogénation, la déshydrogénation, l'hydrogénolyse, l'oxydation, la polymérisation, l'isomérisation, la déshydrogénation et la cyclisation utilisant ces catalyseurs.
PCT/NL2000/000286 1999-05-07 2000-05-02 Catalyseurs stables et leurs procedes de fabrication et d'utilisation Ceased WO2000067902A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU46251/00A AU4625100A (en) 1999-05-07 2000-05-02 Stable catalysts and processes for making and using the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP99201421.7 1999-05-07
US13477599P 1999-05-17 1999-05-17

Publications (1)

Publication Number Publication Date
WO2000067902A1 true WO2000067902A1 (fr) 2000-11-16

Family

ID=22464939

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL2000/000286 Ceased WO2000067902A1 (fr) 1999-05-07 2000-05-02 Catalyseurs stables et leurs procedes de fabrication et d'utilisation

Country Status (1)

Country Link
WO (1) WO2000067902A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2842125A1 (fr) * 2002-07-09 2004-01-16 Sicat Methode de preparation par impregnation biphasique de nouveaux catalyseurs pour catalyse heterogene, et utilisation desdits catalyseurs
US8487140B2 (en) 2008-08-29 2013-07-16 Exxonmobil Chemical Patents Inc. Process for producing phenol
JP2015040192A (ja) * 2013-08-22 2015-03-02 宇部興産株式会社 シクロヘキサノンの製造方法及びその装置
US9061270B2 (en) 2010-02-05 2015-06-23 Exxonmobil Chemical Patents Inc. Cyclohexanone dehydrogenation catalyst and process
WO2015163221A1 (fr) * 2014-04-22 2015-10-29 宇部興産株式会社 Catalyseur d'hydrogénation, procédé de production dudit catalyseur et procédé de production de cyclohexanone ou d'un de ses dérivés faisant intervenir ledit catalyseur
US9242227B2 (en) 2010-02-05 2016-01-26 Exxonmobil Chemical Patents Inc. Dehydrogenation catalyst and process
US9249077B2 (en) 2009-07-14 2016-02-02 Exxonmobil Chemical Patents Inc. Dehydrogenation process
JP2016047504A (ja) * 2014-08-28 2016-04-07 宇部興産株式会社 水素化方法、水素化触媒の前処理方法及びこれを用いた水素化触媒
US9382171B2 (en) 2010-02-05 2016-07-05 Exxonmobil Chemical Patents Inc. Iridium-containing catalysts, their production and use

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH487107A (de) * 1966-05-20 1970-03-15 Hoechst Ag Verfahren zur Herstellung von Carbonsäurevinylestern
DE2025726A1 (en) * 1970-05-26 1971-12-09 Ljubarskij, Grigorij Dawidowitsch; Streletz, Margarita Michailowna; Sokolskij, Wazlaw Alexandrowitsch; Moskau Cyclohexanone prodn - by hydrogenation of phenol in the - presence of a promoted palladium catalyst
US4061598A (en) * 1976-06-25 1977-12-06 E. I. Du Pont De Nemours And Company Catalyst for hydrogenating anthraquinones
US5189004A (en) * 1991-11-18 1993-02-23 Union Carbide Chemicals & Plastics Technology Corporation Alkenyl alkanoate catalyst process
EP0764463A2 (fr) * 1995-09-23 1997-03-26 Basf Aktiengesellschaft Catalyseur supporté contenant du palladium pour l'hydrogénation sélective de l'acétylène dans un courant d'hydrocarbures

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH487107A (de) * 1966-05-20 1970-03-15 Hoechst Ag Verfahren zur Herstellung von Carbonsäurevinylestern
DE2025726A1 (en) * 1970-05-26 1971-12-09 Ljubarskij, Grigorij Dawidowitsch; Streletz, Margarita Michailowna; Sokolskij, Wazlaw Alexandrowitsch; Moskau Cyclohexanone prodn - by hydrogenation of phenol in the - presence of a promoted palladium catalyst
US4061598A (en) * 1976-06-25 1977-12-06 E. I. Du Pont De Nemours And Company Catalyst for hydrogenating anthraquinones
US5189004A (en) * 1991-11-18 1993-02-23 Union Carbide Chemicals & Plastics Technology Corporation Alkenyl alkanoate catalyst process
EP0764463A2 (fr) * 1995-09-23 1997-03-26 Basf Aktiengesellschaft Catalyseur supporté contenant du palladium pour l'hydrogénation sélective de l'acétylène dans un courant d'hydrocarbures

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2842125A1 (fr) * 2002-07-09 2004-01-16 Sicat Methode de preparation par impregnation biphasique de nouveaux catalyseurs pour catalyse heterogene, et utilisation desdits catalyseurs
WO2004007074A1 (fr) * 2002-07-09 2004-01-22 Sicat Methode de preparation de catalyseurs pour catalyse heterogene par impregnation en plusieurs etapes, catalyseurs et utilisation desdits catalyseurs
US8487140B2 (en) 2008-08-29 2013-07-16 Exxonmobil Chemical Patents Inc. Process for producing phenol
US9249077B2 (en) 2009-07-14 2016-02-02 Exxonmobil Chemical Patents Inc. Dehydrogenation process
US9061270B2 (en) 2010-02-05 2015-06-23 Exxonmobil Chemical Patents Inc. Cyclohexanone dehydrogenation catalyst and process
US9242227B2 (en) 2010-02-05 2016-01-26 Exxonmobil Chemical Patents Inc. Dehydrogenation catalyst and process
US9382171B2 (en) 2010-02-05 2016-07-05 Exxonmobil Chemical Patents Inc. Iridium-containing catalysts, their production and use
JP2015040192A (ja) * 2013-08-22 2015-03-02 宇部興産株式会社 シクロヘキサノンの製造方法及びその装置
WO2015163221A1 (fr) * 2014-04-22 2015-10-29 宇部興産株式会社 Catalyseur d'hydrogénation, procédé de production dudit catalyseur et procédé de production de cyclohexanone ou d'un de ses dérivés faisant intervenir ledit catalyseur
JP6075506B2 (ja) * 2014-04-22 2017-02-08 宇部興産株式会社 水素化触媒及びその製造方法、並びにそれを用いたシクロヘキサノン又はその誘導体の製造方法
JP2016047504A (ja) * 2014-08-28 2016-04-07 宇部興産株式会社 水素化方法、水素化触媒の前処理方法及びこれを用いた水素化触媒

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