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FR2987046B1 - Procede d'hydroxylation de composes aromatiques, catalyseur d'hydroxylation et son procede de preparation - Google Patents

Procede d'hydroxylation de composes aromatiques, catalyseur d'hydroxylation et son procede de preparation

Info

Publication number
FR2987046B1
FR2987046B1 FR1251496A FR1251496A FR2987046B1 FR 2987046 B1 FR2987046 B1 FR 2987046B1 FR 1251496 A FR1251496 A FR 1251496A FR 1251496 A FR1251496 A FR 1251496A FR 2987046 B1 FR2987046 B1 FR 2987046B1
Authority
FR
France
Prior art keywords
hydroxylation
preparing
same
aromatic compounds
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.)
Expired - Fee Related
Application number
FR1251496A
Other languages
English (en)
Other versions
FR2987046A1 (fr
Inventor
Thibaut Corre
Belen Albela
Laurent Bonneviot
Laurent Garel
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.)
Centre National de la Recherche Scientifique CNRS
Rhodia Operations SAS
Original Assignee
Centre National de la Recherche Scientifique CNRS
Rhodia Operations SAS
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
Priority to FR1251496A priority Critical patent/FR2987046B1/fr
Application filed by Centre National de la Recherche Scientifique CNRS, Rhodia Operations SAS filed Critical Centre National de la Recherche Scientifique CNRS
Priority to EP13704443.4A priority patent/EP2814606A1/fr
Priority to CN201810264001.5A priority patent/CN108435247A/zh
Priority to PCT/EP2013/053054 priority patent/WO2013120986A1/fr
Priority to JP2014557051A priority patent/JP6509561B2/ja
Priority to US14/378,656 priority patent/US9682909B2/en
Priority to CN201380009890.6A priority patent/CN104302395A/zh
Publication of FR2987046A1 publication Critical patent/FR2987046A1/fr
Application granted granted Critical
Publication of FR2987046B1 publication Critical patent/FR2987046B1/fr
Priority to US15/598,400 priority patent/US10173954B2/en
Priority to JP2018151151A priority patent/JP2019001711A/ja
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen
    • 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
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/20—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state
    • B01J35/23—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state in a colloidal state
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
    • B01J35/391—Physical properties of the active metal ingredient
    • B01J35/393—Metal or metal oxide crystallite size
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/40—Catalysts, in general, characterised by their form or physical properties characterised by dimensions, e.g. grain size
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/40—Catalysts, in general, characterised by their form or physical properties characterised by dimensions, e.g. grain size
    • B01J35/45—Nanoparticles
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/70—Catalysts, in general, characterised by their form or physical properties characterised by their crystalline properties, e.g. semi-crystalline
    • B01J35/77—Compounds characterised by their crystallite size
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/08—Heat treatment
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B37/00—Compounds having molecular sieve properties but not having base-exchange properties
    • C01B37/005—Silicates, i.e. so-called metallosilicalites or metallozeosilites
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B39/00—Compounds having molecular sieve and base-exchange properties, e.g. crystalline zeolites; Their preparation; After-treatment, e.g. ion-exchange or dealumination
    • C01B39/02—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof; Direct preparation thereof; Preparation thereof starting from a reaction mixture containing a crystalline zeolite of another type, or from preformed reactants; After-treatment thereof
    • C01B39/06—Preparation of isomorphous zeolites characterised by measures to replace the aluminium or silicon atoms in the lattice framework by atoms of other elements, i.e. by direct or secondary synthesis
    • C01B39/065—Galloaluminosilicates; Group IVB- metalloaluminosilicates; Ferroaluminosilicates
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B39/00—Compounds having molecular sieve and base-exchange properties, e.g. crystalline zeolites; Their preparation; After-treatment, e.g. ion-exchange or dealumination
    • C01B39/02—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof; Direct preparation thereof; Preparation thereof starting from a reaction mixture containing a crystalline zeolite of another type, or from preformed reactants; After-treatment thereof
    • C01B39/36—Pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/58—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of molecular oxygen
    • 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
    • B01J2235/00—Indexing scheme associated with group B01J35/00, related to the analysis techniques used to determine the catalysts form or properties
    • 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
    • B01J2235/00—Indexing scheme associated with group B01J35/00, related to the analysis techniques used to determine the catalysts form or properties
    • B01J2235/10—Infrared [IR]
    • 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
    • B01J2235/00—Indexing scheme associated with group B01J35/00, related to the analysis techniques used to determine the catalysts form or properties
    • B01J2235/15—X-ray diffraction
    • 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
    • B01J2235/00—Indexing scheme associated with group B01J35/00, related to the analysis techniques used to determine the catalysts form or properties
    • B01J2235/30—Scanning electron microscopy; Transmission electron microscopy
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/60—Particles characterised by their size
    • C01P2004/61—Micrometer sized, i.e. from 1-100 micrometer
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/12—Surface area
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/16—Pore diameter

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Geology (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Thermal Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Silicates, Zeolites, And Molecular Sieves (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Dispersion Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)

Abstract

La présente invention concerne un procédé d'hydroxylation d'un composé de formule (I) par réaction du composé de formule (I) avec un agent oxydant, en présence d'une zéolite titano-silicalite préparée par cristallisation précédée d'une étape de mûrissement. La présente invention concerne également une zéolite titano-silicalite et son procédé de préparation.
FR1251496A 2012-02-17 2012-02-17 Procede d'hydroxylation de composes aromatiques, catalyseur d'hydroxylation et son procede de preparation Expired - Fee Related FR2987046B1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
FR1251496A FR2987046B1 (fr) 2012-02-17 2012-02-17 Procede d'hydroxylation de composes aromatiques, catalyseur d'hydroxylation et son procede de preparation
CN201810264001.5A CN108435247A (zh) 2012-02-17 2013-02-15 用于芳香族化合物的羟基化的方法、羟基化催化剂以及用于制备羟基化催化剂的方法
PCT/EP2013/053054 WO2013120986A1 (fr) 2012-02-17 2013-02-15 Procede d'hydroxylation de composes aromatiques, catalyseur d'hydroxylation et son procede de preparation
JP2014557051A JP6509561B2 (ja) 2012-02-17 2013-02-15 芳香族化合物のヒドロキシル化のための方法、ヒドロキシル化触媒および触媒を調製するための方法
EP13704443.4A EP2814606A1 (fr) 2012-02-17 2013-02-15 Procede d'hydroxylation de composes aromatiques, catalyseur d'hydroxylation et son procede de preparation
US14/378,656 US9682909B2 (en) 2012-02-17 2013-02-15 Process for hydroxylation of aromatic compounds, hydroxylation catalyst and process for preparing same
CN201380009890.6A CN104302395A (zh) 2012-02-17 2013-02-15 用于芳香族化合物的羟基化的方法、羟基化催化剂以及用于制备羟基化催化剂的方法
US15/598,400 US10173954B2 (en) 2012-02-17 2017-05-18 Process for hydroxylation of aromatic compounds, hydroxylation catalyst and process for preparing same
JP2018151151A JP2019001711A (ja) 2012-02-17 2018-08-10 芳香族化合物のヒドロキシル化のための方法、ヒドロキシル化触媒および触媒を調製するための方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1251496A FR2987046B1 (fr) 2012-02-17 2012-02-17 Procede d'hydroxylation de composes aromatiques, catalyseur d'hydroxylation et son procede de preparation

Publications (2)

Publication Number Publication Date
FR2987046A1 FR2987046A1 (fr) 2013-08-23
FR2987046B1 true FR2987046B1 (fr) 2014-03-21

Family

ID=47716054

Family Applications (1)

Application Number Title Priority Date Filing Date
FR1251496A Expired - Fee Related FR2987046B1 (fr) 2012-02-17 2012-02-17 Procede d'hydroxylation de composes aromatiques, catalyseur d'hydroxylation et son procede de preparation

Country Status (6)

Country Link
US (2) US9682909B2 (fr)
EP (1) EP2814606A1 (fr)
JP (2) JP6509561B2 (fr)
CN (2) CN104302395A (fr)
FR (1) FR2987046B1 (fr)
WO (1) WO2013120986A1 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
UA124030C2 (uk) 2017-01-09 2021-07-07 Евонік Оперейшнс Гмбх Спосіб одержання оксидів металів за допомогою розпилювального піролізу
CN107597173B (zh) * 2017-10-11 2020-07-21 中国天辰工程有限公司 一种苯酚羟基化合成苯二酚的催化剂及其制备方法
EP3495321A1 (fr) 2017-12-07 2019-06-12 Evonik Degussa GmbH Préparation de silicates de métal en poudre, cristallins et poreux par pyrolyse par projection à la flamme
FR3075198B1 (fr) * 2017-12-15 2020-04-03 Rhodia Operations Procede d'hydroxylation d'un compose aromatique
WO2019182035A1 (fr) * 2018-03-23 2019-09-26 宇部興産株式会社 Procédé de production de composé hydroxy aromatique
WO2019225549A1 (fr) * 2018-05-21 2019-11-28 三井化学株式会社 Méthode de fabrication d'aluminosilicate modifié, aluminosilicate modifié et méthode de fabrication d'un composé dihydroxy aromatique l'utilisant
JP7443370B2 (ja) * 2018-08-24 2024-03-05 ローディア オペレーションズ マイクロポーラスアルミノチタノシリケート結晶性ゼオライト、その調製方法及び利用
EP3628642A1 (fr) * 2018-09-25 2020-04-01 Evonik Operations GmbH Procédé de fabrication de silicates de métal cristallin pulvérulent et poreux employant une pyrolyse au pistolet à flamme
SG11202110277RA (en) 2019-04-29 2021-11-29 Basf Se Molding comprising a type mfi zeolitic titanosilicate and a silica binder, its preparation process and use as catalyst
JP7556686B2 (ja) 2019-12-26 2024-09-26 日揮触媒化成株式会社 アルコキシ基を含む原料を使用しないチタノシリケートゼオライトの製造方法
CN112717998B (zh) * 2021-01-19 2022-03-11 中国科学院大连化学物理研究所 一种高活性苯酚羟基化钛硅分子筛催化剂及其制备方法
CN112871206B (zh) * 2021-01-19 2022-04-08 中国科学院大连化学物理研究所 一种低成本高活性苯酚羟基化钛硅分子筛催化剂的制备方法
CN114634404B (zh) * 2022-04-01 2023-09-15 北京化工大学 一种苯氧化制备苯酚的方法

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Also Published As

Publication number Publication date
WO2013120986A1 (fr) 2013-08-22
CN108435247A (zh) 2018-08-24
US10173954B2 (en) 2019-01-08
JP6509561B2 (ja) 2019-05-08
CN104302395A (zh) 2015-01-21
JP2019001711A (ja) 2019-01-10
US9682909B2 (en) 2017-06-20
JP2015511945A (ja) 2015-04-23
FR2987046A1 (fr) 2013-08-23
US20150299076A1 (en) 2015-10-22
EP2814606A1 (fr) 2014-12-24
US20170253547A1 (en) 2017-09-07

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