GB577581A - Improvements in or relating to the alkylation of organic compounds - Google Patents

Improvements in or relating to the alkylation of organic compounds

Info

Publication number
GB577581A
GB577581A GB21123/43A GB2112343A GB577581A GB 577581 A GB577581 A GB 577581A GB 21123/43 A GB21123/43 A GB 21123/43A GB 2112343 A GB2112343 A GB 2112343A GB 577581 A GB577581 A GB 577581A
Authority
GB
United Kingdom
Prior art keywords
olefin
alkylation
feed
isobutane
tubes
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
Application number
GB21123/43A
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.)
Texaco Development Corp
Original Assignee
Texaco Development Corp
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 Texaco Development Corp filed Critical Texaco Development Corp
Publication of GB577581A publication Critical patent/GB577581A/en
Expired legal-status Critical Current

Links

Classifications

    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J10/00Chemical processes in general for reacting liquid with gaseous media other than in the presence of solid particles, or apparatus specially adapted therefor
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/02Apparatus characterised by being constructed of material selected for its chemically-resistant properties
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24Stationary reactors without moving elements inside
    • B01J19/2455Stationary reactors without moving elements inside provoking a loop type movement of the reactants
    • B01J19/246Stationary reactors without moving elements inside provoking a loop type movement of the reactants internally, i.e. the mixture circulating inside the vessel such that the upward stream is separated physically from the downward stream(s)
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/56Addition to acyclic hydrocarbons
    • C07C2/58Catalytic processes
    • C07C2/62Catalytic processes with acids
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/02Apparatus characterised by their chemically-resistant properties
    • B01J2219/0204Apparatus characterised by their chemically-resistant properties comprising coatings on the surfaces in direct contact with the reactive components
    • B01J2219/0236Metal based
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/02Sulfur, selenium or tellurium; Compounds thereof
    • C07C2527/053Sulfates or other compounds comprising the anion (SnO3n+1)2-
    • C07C2527/054Sulfuric acid or other acids with the formula H2Sn03n+1

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

<PICT:0577581/IV/1> <PICT:0577581/IV/2> An organic compound containing a replaceable hydrogen atom is alkylated in liquid phase in the presence of a liquid alkylation catalyst in a mechanically agitated reaction zone by introducing the alkylating agent by multi-point ignition in finely-divided form through a large number, in excess of ten, of small feed openings, each of a diameter less than 1/4 inch, spaced throughout a region of the reaction zone confining at least about 1/10 th, and preferably about 1/4 or more, of the volume of the agitated mixture to prevent local accumulation of unreacted alkylating agent. The feed openings may be down to capillary size and spaced throughout 1/4 -\ba1/2 or more of the length of the recirculating passage where a mixer having a recirculating flow is used. The compound to be alkylated, such as an isoparaffin, may be injected in the same way, for example by mixing with the alkylating agent such as an olefin. Ratios of isoparaffin to olefin at the point of entry of 1500-2,000,000 : 1 or higher are obtainable. Contact times may be reduced, for example to 1-5 mins. Alkylation of isobutane, isopentane or isohexane with ethylene, propylene, butenes, pentenes, hexenes or higher olefins or olefin polymers, with alkyl esters such as chlorides, sulphates, fluorides, or aliphatic alcohols and ethers such as tertiary butyl or isopropyl alcohol or butyl ether, alkylation of normal paraffins, and of aromatics and hydroxy - aromatics such as benzene, toluene, xylene, phenol or cresol, for example of benzene with ethylene or chlorinated kerosene to produce ethyl benzene or "keryl benzene," are reactions specified. Alkylation catalysts include sulphuric, hydrofluoric, chlorsulphonic and fluorsulphonic acids, A1C13-hydrocarbon complexes and BF3nH2O. Multi-stage alkylation may be used with split olefin feed between the stages. A pump 14, Fig. 1, causes circulation of the reactor contents through and around an interior tube 13. The olefin, if desired together with part or all of the isobutane feed, is fed under pressure to the annular jacket 12, the inner wall of which is perforated or of porous material such as alundum so that multi-point injection occurs. A liner having 1/16 -\ba1/8 in. perforations spaced 1-6 ins. apart is satisfactory. Pressure pulsations applied to jacket 12 may be used to prevent clogging. The reactor contents are stratified, acid being recycled, and hydrocarbon neutralized, stabilized and fractionated, isobutane being also recycled. In modifications, Figs. 2 and 3 (not shown), the feed is injected through a perforated or porous cylinder pointed at its lower end and located within the interior tube through and around which the acid is circulated, additional cylinders being mounted outside this tube if desired, or annular injectors disposed above one another surround the tube, other injectors being located within it. The feed openings may be provided on one face or the edges only if desired, and the feed members are so spaced that alkylating agent from one has substantially reacted by the time the circulating stream reaches the next. In the pump and time tank reactor, Fig. 4, the olefin, preferably with part of the isobutane, is fed to chambers 127, 128 surrounding perforate pipes 123, 125 through which the acid reaction stream circulates. A combined alkylator and chiller 107 comprises a casing 131 through which a refrigerant such as propane is circulated. The circulating stream passes through tubes 132 between headers 130, 133, and the olefin is fed by lines 119, 120 through tubes 140 located within tubes 132 and connected by headers 138, 139. The tubes 140 are porous or perforated for passage of the olefin into the stream.
GB21123/43A 1943-02-24 1943-12-16 Improvements in or relating to the alkylation of organic compounds Expired GB577581A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US577581XA 1943-02-24 1943-02-24

Publications (1)

Publication Number Publication Date
GB577581A true GB577581A (en) 1946-05-23

Family

ID=22012581

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21123/43A Expired GB577581A (en) 1943-02-24 1943-12-16 Improvements in or relating to the alkylation of organic compounds

Country Status (1)

Country Link
GB (1) GB577581A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1546070A2 (en) * 2002-08-19 2005-06-29 Catalytic Distillation Technologies Pulse flow reaction
WO2012152600A1 (en) * 2011-05-09 2012-11-15 Versalis S.P.A. Ammoximation reactor for cyclohexanone oxime production
US8927770B2 (en) 2011-05-10 2015-01-06 Salpem, S.P.A. High-yield process for the synthesis of urea
WO2016148971A1 (en) * 2015-03-13 2016-09-22 Chevron U.S.A. Inc. Pneumatically agitated ionic liquid alkylation using vaporization to remove reaction heat
US10023529B2 (en) * 2010-04-30 2018-07-17 Asaki Kasei Chemicals Corporation Apparatus for removing catalyst surface substances
US10486131B2 (en) 2017-10-26 2019-11-26 Chevron U.S.A. Inc. Integrated reactor system for ionic liquid-catalyzed hydrocarbon conversion

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1546070A2 (en) * 2002-08-19 2005-06-29 Catalytic Distillation Technologies Pulse flow reaction
EP1546070A4 (en) * 2002-08-19 2009-11-25 Catalytic Distillation Tech Pulse flow reaction
US10023529B2 (en) * 2010-04-30 2018-07-17 Asaki Kasei Chemicals Corporation Apparatus for removing catalyst surface substances
WO2012152600A1 (en) * 2011-05-09 2012-11-15 Versalis S.P.A. Ammoximation reactor for cyclohexanone oxime production
US10525429B2 (en) 2011-05-09 2020-01-07 Versalis S.P.A. Ammoximation reactor for cyclohexanone oxime production
US8927770B2 (en) 2011-05-10 2015-01-06 Salpem, S.P.A. High-yield process for the synthesis of urea
WO2016148971A1 (en) * 2015-03-13 2016-09-22 Chevron U.S.A. Inc. Pneumatically agitated ionic liquid alkylation using vaporization to remove reaction heat
US10486131B2 (en) 2017-10-26 2019-11-26 Chevron U.S.A. Inc. Integrated reactor system for ionic liquid-catalyzed hydrocarbon conversion

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