US3420909A - Alkylation process - Google Patents

Alkylation process Download PDF

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US3420909A
US3420909A US661776A US3420909DA US3420909A US 3420909 A US3420909 A US 3420909A US 661776 A US661776 A US 661776A US 3420909D A US3420909D A US 3420909DA US 3420909 A US3420909 A US 3420909A
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catalyst
hydrocarbon
alkylation
valence
chloride
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Louis Schmerling
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Universal Oil Products Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/76—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/08—Halides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S585/00—Chemistry of hydrocarbon compounds
    • Y10S585/929—Special chemical considerations
    • Y10S585/94—Opening of hydrocarbon ring

Definitions

  • This invention relates to a conversion process for the alkylation of alkylatable aromatic hydrocarbons into more useful compounds. More specifically, this invention is concerned with a conversion process for the alkylation of an alkylatable aromatic hydrocarbon with a saturated hydrocarbon utilizing a novel catalyst comprising aluminum chloride and the higher-valence halide of a metal which forms at least two metal halides differing in valence.
  • a specific object of this invention is to provide a novel method and a novel catalyst for alkylating alkylatable aromatic hydrocarbons to provide the desired alkylated product in high yields.
  • One embodiment of the invention relates to a process for the alkylation of an alkylatable aromatic hydrocarbon with a saturated hydrocarbon at alkylation conditions in the presence of a catalyst comprising aluminum chloride and the higher-valence halide of a metal which forms at least two metal halides differing in valence.
  • a second embodiment of this invention relates to a process for the alkylation of an alkylatable benzene hydrocarbon with a saturated hydrocarbon at alkylation conditions including a temperature in the range of about to about 200 C. and a pressure in the range of from about atmospheric to about 200 atmospheres in the presence of a catalyst comprising aluminum chloride and the higher-valence halide of a metal which forms at least two metal halides differing in valence.
  • the process of my invention is applicable to the alkylatable aromatic hydrocarbons including, for example, benzene, toluene, ortho-Xylene, meta-xylene, para-xylene, ethylbenzene, ortho-ethyltoluene, meta-ethyltoluene, paraethyltoluene, 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene, 1,3,5-trimethylbenzene, diethylbenzene, triethylbenzene, normal propylbenzene, isopropylbenzene, etc., and mixtures thereof.
  • Preferred alkylatable aromatic hydrocarbons are benzene and monoalkylated benzenes.
  • Higher molecular weight alkyl aromatic hydrocarbons are suitable. These include those aromatic hydrocarbons such as are produced by the alkylation of aromatic hydrocarbons with olefin polymers and are used as intermediates in the preparation of sulfonate surface-active agents. Such products include hexylbenzenes, nonylbenzene, dodecylbenzenes, pentadecylbenzenes, hexyltoluenes, nonyltoluenes, dodecyltoluenes, pentadecyltoluenes, etc.
  • the product is obtained as a high boiling fraction in which the alkyl group attached to the aromatic nucleus varies in size from about 0,, to C
  • suitable aromatic hydrocarbons which at specified conditions, depending upon the melting point of the aromatic chosen, would be in liquid form, would include those aromatic hydrocarbons with two or more aryl groups such as diphenyl, diphenylmethane, triphenyl, triphenylmethaue, fiuorene, stilbene, etc.
  • aromatic hydrocarbons utilizable in the scope of this invention which, because they may be normally solid at the alkylation conditions, are alkylated in a solvent, preferably an excess of the saturated hydrocarbon, include those containing condensed aromatic rings.
  • naphthalenes include naphthalenes, alkylnaphthalenes, anthracene, phenanthrene, naphthacene, rubrene, etc.
  • aromatic hydrocarbons that could be utilized in the process of this invention, the benzene hydrocarbons are preferred, and of the preferred benzene hydrocarbons, benzene itself is particularly preferred.
  • the saturated hydrocarbons acting as the alkylating agent, may be selected from diverse materials including the acyclic paraflin hydrocarbons and cycloparaflin hydrocarbons are the alkanes and cycloalkanes containing tertiary carbon atoms.
  • suitable alkylating agents include normal butane, normal pentane, isopentane, normal hexane, isohexane, normal heptane, Z-methylhexane, normal octane, etc.
  • Suitable cycloalkanes such as the cyclopentanes and cyclohexanes, including cyclopentane, methylcyclopentane, dimethylcyclopentanes, cyclohexane, methylcyclohexane, dimethylcyclohexanes, etc. Mixtures of saturated hydrocarbons may also be utilized.
  • the invention is concerned with a process for the alkylation of alkylatable aromatic hydrocarbons, said process being effected by the presence of a catalyst which possesses a high degree of hydrocarbon conversion activity and is particularly effective as an alkylation catalyst for alkylatable aromatic hydrocarbons.
  • the catalyst comprises aluminum chloride and a highervalence halide of a metal which forms at least two metal halides differing in valence.
  • Suitable metals which form at least two metal halides ditfering in valence include copper, mercury, iron, tin, cobalt, molybdenum, manganese, and chromium.
  • the various bromides and chlorides of the above metals including mercuric chloride, mercuric bromide, cupric chloride, cupric bromide, ferric chloride, ferric bromide, stannic chloride, stannic bromide, cobaltic chloride, cobaltic bromide, molybdenum trichloride, molybdenum tetrachloride, molybdenum tetrabromide, molybdenum pentabromide, manganese trichloride, manganese tribromide, chromic chloride, chromic bromide, etc., are thus utilizable in the scope of my invention.
  • a particularly preferred catalyst for use in the process of this invention is the catalyst comprising aluminum chloride and cupric chloride.
  • the aluminum chloride may be used in a catalytic amount, or preferably, in equimolar amounts with the cupric chloride.
  • the chlorides may be added separately or as a complex, Al Cl -CuCl-
  • the process of this invention utilizing the catalyst hereinbefore set forth may be effected in any suitable manner and may comprise either a batch or a continuous type operation.
  • the preferred method by which the process of this invention may be effected is a continuous type operation.
  • One particular method is the operation in which the alkylatable aromatic hydrocarbon and the saturated hydrocarbon are continuously charged to a reaction zone containing the desired catalyst, said zone being maintained at the proper operating conditions of temperature and pressure, that is, a temperature in the range of from about 0 to about 200 C. and preferably a temperature of from about 20 to about C., and a pressure including a pressure of from about atmospheric to about 200 atmospheres or more.
  • the rate at which the hydrocarbon charge is added may be varied within a relatively Wide range.
  • the reaction zone may comprise an unpacked vessel or coil or may contain a packing material.
  • the two reactants may be charged through separate lines, or, if so desired, may be admixed prior to entry into said reaction zone and charged thereto in a single stream.
  • This charge passes into the reaction zone containing the catalyst in an upward, downward, or radial flow and the alkylated product is continuously withdrawn, separated from the reactor etfiuent and recovered, while any other unreacted starting material may be recycled to form a portion of the feed stock.
  • Another continuous type operation comprises the moving bed type in which the reactants and the catalyst move either concurrently or countercurrently to each other while passing through said reaction zone.
  • Still another type operation which may be used in the batch type operation in which a quantity of the alkylatable aromatic hydrocarbon, the saturated hydrocarbon and the catalyst are placed in an appropriate apparatus such as, for example, a rotating or stirred autoclave.
  • the apparatus is then maintained at the desired temperature for a predetermined residence time at the end of which time the flask and contents thereof are cooled to room temperature (it a higher reaction was employed) and the desired reaction product is recovered by conventional means, such as, for example, by washing, drying, fractional distillation, crystallization, etc.
  • Example I In this example, 20 grams (0.2 mole) of benzene and 24 grams (0.33 mole) of isopentane were stirred and mixed at room temperature with 22 grams of catalyst In this example, 46.5 grams (0.5 mole) of toluene and 53 grams (0.62 mole) of 2,3-dimethylbutane were mixed and stirred at 25-27 C. with a catalyst comprising alu- 4 minum chloride and cupric chloride. The vigorous evolution of HCl was noted. The product was subsequently treated with ice water followed by ether extraction and a product containing two hexylbenzene isomers including 2-phenyl-2,3-dimethylbutane and 2-phenyl-3,3-dimethylbutane was recovered.
  • alkylatable aromatic hydrocarbon is a benzene hydrocarbon.
  • alkylation conditions include a temperature in the range of from about 0 to about 200 C. and a pressure in the range of from about atmospheric to about 200 atmospheres.

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

Description

United States Patent 01 Patented Jan. 7, 1969 lice 3,420,909 ALKYLATION PROCESS Louis Schmerling, Riverside, lll., assignor to Umversal Oil Products Company, Des Plaines, 11]., a corporation of Delaware No Drawing. Filed Aug. 21, 1967, Ser. No. 661,776 US. Cl. 260-671 8 Claims Int. Cl. C07c 3/56 ABSTRACT OF THE DISCLOSURE An alkylatable aromatic hydrocarbon is alkylated with a saturated hydrocarbon utilizing a catalyst comprising aluminum chloride and the higher-valence halide of a metal which forms at least two metal halides differing in valence.
Description of the invention This invention relates to a conversion process for the alkylation of alkylatable aromatic hydrocarbons into more useful compounds. More specifically, this invention is concerned with a conversion process for the alkylation of an alkylatable aromatic hydrocarbon with a saturated hydrocarbon utilizing a novel catalyst comprising aluminum chloride and the higher-valence halide of a metal which forms at least two metal halides differing in valence.
It is, therefore, an object of this invention to provide a process for the alkylation of alkylatable aromatic hydrocarbons utilizing a novel alkylation catalyst.
A specific object of this invention is to provide a novel method and a novel catalyst for alkylating alkylatable aromatic hydrocarbons to provide the desired alkylated product in high yields.
One embodiment of the invention relates to a process for the alkylation of an alkylatable aromatic hydrocarbon with a saturated hydrocarbon at alkylation conditions in the presence of a catalyst comprising aluminum chloride and the higher-valence halide of a metal which forms at least two metal halides differing in valence.
A second embodiment of this invention relates to a process for the alkylation of an alkylatable benzene hydrocarbon with a saturated hydrocarbon at alkylation conditions including a temperature in the range of about to about 200 C. and a pressure in the range of from about atmospheric to about 200 atmospheres in the presence of a catalyst comprising aluminum chloride and the higher-valence halide of a metal which forms at least two metal halides differing in valence.
The process of my invention is applicable to the alkylatable aromatic hydrocarbons including, for example, benzene, toluene, ortho-Xylene, meta-xylene, para-xylene, ethylbenzene, ortho-ethyltoluene, meta-ethyltoluene, paraethyltoluene, 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene, 1,3,5-trimethylbenzene, diethylbenzene, triethylbenzene, normal propylbenzene, isopropylbenzene, etc., and mixtures thereof. Preferred alkylatable aromatic hydrocarbons are benzene and monoalkylated benzenes. Higher molecular weight alkyl aromatic hydrocarbons are suitable. These include those aromatic hydrocarbons such as are produced by the alkylation of aromatic hydrocarbons with olefin polymers and are used as intermediates in the preparation of sulfonate surface-active agents. Such products include hexylbenzenes, nonylbenzene, dodecylbenzenes, pentadecylbenzenes, hexyltoluenes, nonyltoluenes, dodecyltoluenes, pentadecyltoluenes, etc. Very often, the product is obtained as a high boiling fraction in which the alkyl group attached to the aromatic nucleus varies in size from about 0,, to C Other suitable aromatic hydrocarbons, which at specified conditions, depending upon the melting point of the aromatic chosen, would be in liquid form, Would include those aromatic hydrocarbons with two or more aryl groups such as diphenyl, diphenylmethane, triphenyl, triphenylmethaue, fiuorene, stilbene, etc. Examples of other aromatic hydrocarbons utilizable in the scope of this invention which, because they may be normally solid at the alkylation conditions, are alkylated in a solvent, preferably an excess of the saturated hydrocarbon, include those containing condensed aromatic rings. These include naphthalenes, alkylnaphthalenes, anthracene, phenanthrene, naphthacene, rubrene, etc. Of the above-mentioned aromatic hydrocarbons that could be utilized in the process of this invention, the benzene hydrocarbons are preferred, and of the preferred benzene hydrocarbons, benzene itself is particularly preferred.
The saturated hydrocarbons, acting as the alkylating agent, may be selected from diverse materials including the acyclic paraflin hydrocarbons and cycloparaflin hydrocarbons are the alkanes and cycloalkanes containing tertiary carbon atoms. Other suitable alkylating agents include normal butane, normal pentane, isopentane, normal hexane, isohexane, normal heptane, Z-methylhexane, normal octane, etc. Suitable cycloalkanes such as the cyclopentanes and cyclohexanes, including cyclopentane, methylcyclopentane, dimethylcyclopentanes, cyclohexane, methylcyclohexane, dimethylcyclohexanes, etc. Mixtures of saturated hydrocarbons may also be utilized.
As hereinabove set forth, the invention is concerned with a process for the alkylation of alkylatable aromatic hydrocarbons, said process being effected by the presence of a catalyst which possesses a high degree of hydrocarbon conversion activity and is particularly effective as an alkylation catalyst for alkylatable aromatic hydrocarbons. The catalyst comprises aluminum chloride and a highervalence halide of a metal which forms at least two metal halides differing in valence. Suitable metals which form at least two metal halides ditfering in valence include copper, mercury, iron, tin, cobalt, molybdenum, manganese, and chromium. The various bromides and chlorides of the above metals including mercuric chloride, mercuric bromide, cupric chloride, cupric bromide, ferric chloride, ferric bromide, stannic chloride, stannic bromide, cobaltic chloride, cobaltic bromide, molybdenum trichloride, molybdenum tetrachloride, molybdenum tetrabromide, molybdenum pentabromide, manganese trichloride, manganese tribromide, chromic chloride, chromic bromide, etc., are thus utilizable in the scope of my invention.
A particularly preferred catalyst for use in the process of this invention is the catalyst comprising aluminum chloride and cupric chloride. The aluminum chloride may be used in a catalytic amount, or preferably, in equimolar amounts with the cupric chloride. The chlorides may be added separately or as a complex, Al Cl -CuCl- The process of this invention utilizing the catalyst hereinbefore set forth may be effected in any suitable manner and may comprise either a batch or a continuous type operation. The preferred method by which the process of this invention may be effected is a continuous type operation. One particular method is the operation in which the alkylatable aromatic hydrocarbon and the saturated hydrocarbon are continuously charged to a reaction zone containing the desired catalyst, said zone being maintained at the proper operating conditions of temperature and pressure, that is, a temperature in the range of from about 0 to about 200 C. and preferably a temperature of from about 20 to about C., and a pressure including a pressure of from about atmospheric to about 200 atmospheres or more. The rate at which the hydrocarbon charge is added may be varied within a relatively Wide range. The reaction zone may comprise an unpacked vessel or coil or may contain a packing material. The two reactants may be charged through separate lines, or, if so desired, may be admixed prior to entry into said reaction zone and charged thereto in a single stream. This charge passes into the reaction zone containing the catalyst in an upward, downward, or radial flow and the alkylated product is continuously withdrawn, separated from the reactor etfiuent and recovered, while any other unreacted starting material may be recycled to form a portion of the feed stock. Another continuous type operation comprises the moving bed type in which the reactants and the catalyst move either concurrently or countercurrently to each other while passing through said reaction zone.
Still another type operation which may be used in the batch type operation in which a quantity of the alkylatable aromatic hydrocarbon, the saturated hydrocarbon and the catalyst are placed in an appropriate apparatus such as, for example, a rotating or stirred autoclave. The apparatus is then maintained at the desired temperature for a predetermined residence time at the end of which time the flask and contents thereof are cooled to room temperature (it a higher reaction was employed) and the desired reaction product is recovered by conventional means, such as, for example, by washing, drying, fractional distillation, crystallization, etc.
The following examples are introduced for the purpose of illustration only with no intention of unduly limiting the broad scope of the present invention.
Example I In this example, 20 grams (0.2 mole) of benzene and 24 grams (0.33 mole) of isopentane were stirred and mixed at room temperature with 22 grams of catalyst In this example, 46.5 grams (0.5 mole) of toluene and 53 grams (0.62 mole) of 2,3-dimethylbutane were mixed and stirred at 25-27 C. with a catalyst comprising alu- 4 minum chloride and cupric chloride. The vigorous evolution of HCl was noted. The product was subsequently treated with ice water followed by ether extraction and a product containing two hexylbenzene isomers including 2-phenyl-2,3-dimethylbutane and 2-phenyl-3,3-dimethylbutane was recovered.
I claim as my invention:
1. A process for the alkylation of an alkylatable aromatic hydrocarbon with a saturated hydrocarbon at alkylation conditions in the presence of a catalyst comprising aluminum chloride and a higher-valence halide of a metal which forms at least two metal halides differing in valence.
2. Theprocess of claim 1 further characterized in that said alkylatable aromatic hydrocarbon is a benzene hydrocarbon.
3. The process of claim 1 further characterized in that said saturated hydrocarbon is an acyclic paraffin hydrocarbon.
4. The process of claim 1 further characterized in that said saturated hydrocarbon is a cycloparafiin hydrocarbon.
5. The process of claim 1 further characterized in that said alkylation conditions include a temperature in the range of from about 0 to about 200 C. and a pressure in the range of from about atmospheric to about 200 atmospheres.
6. The process of claim 1 further characterized in that said metal which forms at least two metal halides differing in valence is copper and that said halide of the metal is chloride.
7. The process of claim 6 further characterized in that said benzene hydrocarbon is benzene and that said saturated hydrocarbon is isopentane.
8. The process of claim 6 further characterized in that said benzene hydrocarbon is toluene and that said saturated hydrocarbon is 2,3-dimethylbutane.
References Cited UNITED STATES PATENTS 2,304,290 12/1942 Van Peski .a 260671 2,426,665 9/1947 Bloch 260-671 2,433,020 12/1947 Becker 260-671 3,109,038 10/1963 Myers 260671 DELBERT E. GANTZ, Primary Examiner.
C. R. DAVIS, Assistant Examiner.
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3676515A (en) * 1971-03-17 1972-07-11 Monsanto Co Process for alkylation of aromatic compounds
US4045504A (en) * 1968-10-23 1977-08-30 The Lummus Company Coupling process
US5202519A (en) * 1992-09-04 1993-04-13 Phillips Petroleum Company Isomerization process and catalyst therefor
US5238896A (en) * 1992-09-04 1993-08-24 Phillips Petroleum Company Isomerization process and catalyst therefor
US5254794A (en) * 1992-08-26 1993-10-19 Phillips Petroleum Company Isomerization catalysts and preparation thereof
US5276242A (en) * 1992-08-26 1994-01-04 Phillips Petroleum Company Alkylation process
US5292988A (en) * 1993-02-03 1994-03-08 Phillips Petroleum Company Preparation and use of isomerization catalysts

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2304290A (en) * 1938-12-16 1942-12-08 Shell Dev Alkylation process
US2426665A (en) * 1942-03-26 1947-09-02 Universal Oil Prod Co Alkylation of aromatic hydrocarbons
US2433020A (en) * 1944-08-14 1947-12-23 Standard Oil Co Catalytic alkylation of aromatic hydrocarbons by paraffins
US3109038A (en) * 1960-09-06 1963-10-29 Phillips Petroleum Co Catalytic alkylation of aromatics with paraffins

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2304290A (en) * 1938-12-16 1942-12-08 Shell Dev Alkylation process
US2426665A (en) * 1942-03-26 1947-09-02 Universal Oil Prod Co Alkylation of aromatic hydrocarbons
US2433020A (en) * 1944-08-14 1947-12-23 Standard Oil Co Catalytic alkylation of aromatic hydrocarbons by paraffins
US3109038A (en) * 1960-09-06 1963-10-29 Phillips Petroleum Co Catalytic alkylation of aromatics with paraffins

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4045504A (en) * 1968-10-23 1977-08-30 The Lummus Company Coupling process
US3676515A (en) * 1971-03-17 1972-07-11 Monsanto Co Process for alkylation of aromatic compounds
US5254794A (en) * 1992-08-26 1993-10-19 Phillips Petroleum Company Isomerization catalysts and preparation thereof
US5276242A (en) * 1992-08-26 1994-01-04 Phillips Petroleum Company Alkylation process
US5202519A (en) * 1992-09-04 1993-04-13 Phillips Petroleum Company Isomerization process and catalyst therefor
US5238896A (en) * 1992-09-04 1993-08-24 Phillips Petroleum Company Isomerization process and catalyst therefor
US5292988A (en) * 1993-02-03 1994-03-08 Phillips Petroleum Company Preparation and use of isomerization catalysts
US5358919A (en) * 1993-02-03 1994-10-25 Phillips Petroleum Company Preparation and use of isomerization catalysts

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