GB577581A - Improvements in or relating to the alkylation of organic compounds - Google Patents
Improvements in or relating to the alkylation of organic compoundsInfo
- 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
Links
Classifications
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- 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
- B01J10/00—Chemical processes in general for reacting liquid with gaseous media other than in the presence of solid particles, or apparatus specially adapted therefor
-
- 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
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/02—Apparatus characterised by being constructed of material selected for its chemically-resistant 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
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2455—Stationary reactors without moving elements inside provoking a loop type movement of the reactants
- B01J19/246—Stationary 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)
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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
- C07C2/54—Preparation 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
- C07C2/56—Addition to acyclic hydrocarbons
- C07C2/58—Catalytic processes
- C07C2/62—Catalytic processes with acids
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- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/02—Apparatus characterised by their chemically-resistant properties
- B01J2219/0204—Apparatus characterised by their chemically-resistant properties comprising coatings on the surfaces in direct contact with the reactive components
- B01J2219/0236—Metal based
-
- 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
- C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
- C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
- C07C2527/054—Sulfuric 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.
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)
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 |
-
1943
- 1943-12-16 GB GB21123/43A patent/GB577581A/en not_active Expired
Cited By (8)
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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