FR2355791A1 - Procede d'hydrodealkylation d'hydrocarbures alkyl aromatiques en presence d'un catalyseur plurimetallique - Google Patents

Procede d'hydrodealkylation d'hydrocarbures alkyl aromatiques en presence d'un catalyseur plurimetallique

Info

Publication number
FR2355791A1
FR2355791A1 FR7618961A FR7618961A FR2355791A1 FR 2355791 A1 FR2355791 A1 FR 2355791A1 FR 7618961 A FR7618961 A FR 7618961A FR 7618961 A FR7618961 A FR 7618961A FR 2355791 A1 FR2355791 A1 FR 2355791A1
Authority
FR
France
Prior art keywords
hydrodealkylation
catalyst
alumina
agglomerates
hydrocarbon
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.)
Granted
Application number
FR7618961A
Other languages
English (en)
Other versions
FR2355791B1 (fr
Inventor
Jean-Pierre Brunelle
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.)
Rhone Poulenc Industries SA
Original Assignee
Rhone Poulenc Industries SA
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 Rhone Poulenc Industries SA filed Critical Rhone Poulenc Industries SA
Priority to FR7618961A priority Critical patent/FR2355791A1/fr
Priority to GB25761/77A priority patent/GB1569658A/en
Priority to US05/808,312 priority patent/US4138443A/en
Priority to NL7706845A priority patent/NL7706845A/xx
Priority to JP7378577A priority patent/JPS532426A/ja
Priority to BE178656A priority patent/BE855956A/fr
Priority to ES459967A priority patent/ES459967A1/es
Priority to DE19772727759 priority patent/DE2727759A1/de
Publication of FR2355791A1 publication Critical patent/FR2355791A1/fr
Application granted granted Critical
Publication of FR2355791B1 publication Critical patent/FR2355791B1/fr
Granted 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • 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
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
    • C07C4/08—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule
    • C07C4/12—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene
    • C07C4/14—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene splitting taking place at an aromatic-aliphatic bond
    • C07C4/18—Catalytic processes
    • 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
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/615—100-500 m2/g
    • 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
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/63—Pore volume
    • B01J35/635—0.5-1.0 ml/g
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
    • C07C2521/04—Alumina
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/06—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of zinc, cadmium or mercury
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
    • C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
    • C07C2523/42—Platinum
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
    • C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
    • C07C2523/44—Palladium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
    • C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
    • C07C2523/46—Ruthenium, rhodium, osmium or iridium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
    • C07C2523/72—Copper
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
    • C07C2523/74—Iron group metals
    • C07C2523/745—Iron
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
    • C07C2523/74—Iron group metals
    • C07C2523/75—Cobalt
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
    • C07C2523/74—Iron group metals
    • C07C2523/755—Nickel

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention concerne un procédé d'hydrodéalkylation d'hydrocarbures alkyl aromatiques par réaction entre l'hydrocarbure et l'hydrogène sans présence de vapeur d'eau. Elle consiste à effectuer la réaction à une température comprise entre 520 degrés et 620 degrés C, sous une pression de 5 à 20 bars, le rapport molaire entre l'hydrogène et l'hydrocarbure étant compris entre 3 et 8, la vitesse spatiale étant comprise entre 3 et 8 volumes de charge liquide par volume de catalyseur et par heure et en présence d'un catalyseur constitué d'une part de rhodium et d'au moins un métal choisi dans le groupe constitué par le cuivre, le nickel, le cobalt, le fer et le zinc et éventuellement de platine et/ou de palladium et d'autre part, par un support d'alumine active ayant une surface spécifique comprise entre 100 et 350 m**2/g et un volume poreux total compris entre 0,5 et 0,8 cm**3/g, ledit support étant constitué soit par des agglomérés d'alumine active obtenue par déshydratation d'hydrate d'alumine dans un courant de gaz chaud, soit par des agglomérés de l'alumine active précédente traités par autoclavage en milieu aqueux neutre ou acide. Le procédé de l'invention s'applique notamment à l'hydrodéalkylation du toluène.
FR7618961A 1976-06-22 1976-06-22 Procede d'hydrodealkylation d'hydrocarbures alkyl aromatiques en presence d'un catalyseur plurimetallique Granted FR2355791A1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
FR7618961A FR2355791A1 (fr) 1976-06-22 1976-06-22 Procede d'hydrodealkylation d'hydrocarbures alkyl aromatiques en presence d'un catalyseur plurimetallique
US05/808,312 US4138443A (en) 1976-06-22 1977-06-20 Hydrodealkylation of alkylaromatic hydrocarbons
GB25761/77A GB1569658A (en) 1976-06-22 1977-06-20 Hydrode-alkylating alkyl-aromatic hydrocarbons
JP7378577A JPS532426A (en) 1976-06-22 1977-06-21 Hydrodealkylation of alkyllaromatic hydrocarbons
NL7706845A NL7706845A (nl) 1976-06-22 1977-06-21 Werkwijze voor de hydro-ontzlkylering van alkyl- aromaten.
BE178656A BE855956A (fr) 1976-06-22 1977-06-21 Procede d'hydrodealkylation d'hydrocarbures alkyl aromatiques en presence d'un catalyseur plurimetallique
ES459967A ES459967A1 (es) 1976-06-22 1977-06-21 Procedimiento para la hidrodesalquilacion de hidrocarburos alquil aromaticos.
DE19772727759 DE2727759A1 (de) 1976-06-22 1977-06-21 Verfahren zur hydrodealkylierung von aromatischen alkylkohlenwasserstoffen in anwesenheit eines aus mehreren metallen bestehenden katalysators

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7618961A FR2355791A1 (fr) 1976-06-22 1976-06-22 Procede d'hydrodealkylation d'hydrocarbures alkyl aromatiques en presence d'un catalyseur plurimetallique

Publications (2)

Publication Number Publication Date
FR2355791A1 true FR2355791A1 (fr) 1978-01-20
FR2355791B1 FR2355791B1 (fr) 1979-07-20

Family

ID=9174726

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7618961A Granted FR2355791A1 (fr) 1976-06-22 1976-06-22 Procede d'hydrodealkylation d'hydrocarbures alkyl aromatiques en presence d'un catalyseur plurimetallique

Country Status (8)

Country Link
US (1) US4138443A (fr)
JP (1) JPS532426A (fr)
BE (1) BE855956A (fr)
DE (1) DE2727759A1 (fr)
ES (1) ES459967A1 (fr)
FR (1) FR2355791A1 (fr)
GB (1) GB1569658A (fr)
NL (1) NL7706845A (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2414034A1 (fr) * 1978-01-06 1979-08-03 Inst Francais Du Petrole Procede de dealkylation, a la vapeur d'eau, d'hydrocarbures aromatiques
GB9306334D0 (en) * 1993-03-26 1993-05-19 Univ Dundee Catalyst
US10118243B2 (en) 2011-10-14 2018-11-06 Lincoln Global, Inc. Real time inductance monitoring in welding and cutting power supply
US11623292B2 (en) 2019-03-29 2023-04-11 Lincoln Global, Inc. Real time resistance monitoring of an arc welding circuit
JP7343044B2 (ja) * 2020-03-31 2023-09-12 三菱ケミカル株式会社 触媒、イソブチレンの製造方法、メタクリル酸の製造方法及びメタクリル酸メチルの製造方法
CN111871428B (zh) * 2020-07-22 2023-04-28 上海应用技术大学 一种用于制备d,l-薄荷醇的铑催化剂及d,l-薄荷醇的制备方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3306944A (en) * 1965-12-27 1967-02-28 Universal Oil Prod Co Process for the hydrodealkylation of alkyl aromatic hydrocarbons
FR1594541A (fr) * 1967-12-20 1970-06-08
US3595932A (en) * 1968-08-20 1971-07-27 Gdal Nossonovich Maslyansky Method of producing benzene and its low-molecular weight homologs
US3812196A (en) * 1970-11-30 1974-05-21 Mitsubishi Petrochemical Co Catalytic steam dealkylation
FR2254542B1 (fr) * 1973-12-13 1976-05-14 Inst Francais Du Petrole
US3992468A (en) * 1974-03-01 1976-11-16 Institut Francais Du Petrole, Des Carburants Et Lubrifiants Et Entreprise De Recherches Et D'activities Petrolieres Elf Process for the catalytic hydrodealkylation of alkylaromatic hydrocarbons

Also Published As

Publication number Publication date
ES459967A1 (es) 1978-05-01
US4138443A (en) 1979-02-06
BE855956A (fr) 1977-12-21
DE2727759A1 (de) 1978-01-05
NL7706845A (nl) 1977-12-27
FR2355791B1 (fr) 1979-07-20
GB1569658A (en) 1980-06-18
JPS532426A (en) 1978-01-11

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