Hf Patents (Class 585/723)
  • Patent number: 4334115
    Abstract: A process for obtaining at least one tert-butyltoluene comprising reacting isobutylene and isobutane in the presence of hydrogen fluoride and then separating said toluene from the hydrocarbon product.
    Type: Grant
    Filed: June 18, 1981
    Date of Patent: June 8, 1982
    Assignee: Phillips Petroleum Company
    Inventor: Raymond L. Cobb
  • Patent number: 4324937
    Abstract: A hydrocarbon conversion process for the production of motor fuel blending stocks from propane and butane is disclosed. Preferably a charge stream comprising a mixture of C.sub.3 -C.sub.4 saturated hydrocarbons is split into a C.sub.3 stream passed into a dehydrogenation zone and a C.sub.4 stream passed into an isostripper column. Normal butanes are removed from the isostripper and passed into an isomerization zone, with product isobutane being concentrated by fractionation in the isostripper. Isobutane and propylene from the dehydrogenation zone are then reacted in an alkylation zone which produces C.sub.5 -plus product hydrocarbons. The effluent of the alkylation zone enters the isostripper. The product stream and a propane-containing stream are withdrawn from the isostripper, with the propane-containing stream being passed into a second separation zone. Alternative butane fractionation systems are disclosed.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: April 13, 1982
    Assignee: UOP Inc.
    Inventor: Bipin V. Vora
  • Patent number: 4320233
    Abstract: Dialkyl ether is produced by passing isoolefin, alkanol and diluent through a series of catalyst zones, cooling the effluent between zones and adding isoolefin and/or alkanol between zones.
    Type: Grant
    Filed: February 9, 1981
    Date of Patent: March 16, 1982
    Assignee: Phillips Petroleum Company
    Inventors: Donald J. Makovec, Paul D. Hann
  • Patent number: 4316998
    Abstract: HF is removed from hydrocarbon streams, e.g., a propane liquid stream from HF alkylation by water washing, the wash stream being contacted with solid caustic to remove moisture therefrom. The used wash water containing HF is combines with aqueous caustic obtained from said contacting and the admixture is used to contact HF acid soluble oil to remove HF therefrom. The thus, used aqueous stream separated from this last contacting is reacted with a calcium compound to form insoluble calcium fluoride and a supernatant aqueous liquid containing regenerated caustic. The regenerated caustic is used to remove the sulfur compounds from the alkylation hydrocarbons feed.
    Type: Grant
    Filed: July 29, 1980
    Date of Patent: February 23, 1982
    Assignee: Phillips Petroleum Company
    Inventor: Joe Van Pool
  • Patent number: 4311866
    Abstract: The reactor effluent hydrocarbon phase from an alkylation zone in which isoparaffin and olefin are contacted in the presence of HF catalyst to form alkylate product is treated by (1) separating a hydrocarbon phase from the reaction effluent; (2) separating the hydrocarbon phase in a first fractionator to produce a bottoms stream containing isoparaffin and alkylate; (3) flashing this bottoms stream to produce a flashed vapor enriched in isoparaffin and a flashed liquid enriched in alkylate; (4) subjecting this flashed liquid to a high pressure, high temperature fractionation in a second fractionator to produce isoparaffin overhead and alkylate from the kettle; and (5) passing the isoparaffin overhead as heat exchange fluid to at least one of (a) the indirect reboiling of the first fractionator kettle, (b) the indirect heating of the bottoms stream being fed from the first fractionator to the flashing step and (c) the indirect heating of the flashed liquid being fed to the second fractionator.
    Type: Grant
    Filed: September 7, 1979
    Date of Patent: January 19, 1982
    Assignee: Phillips Petroleum Company
    Inventor: Charles C. Chapman
  • Patent number: 4304947
    Abstract: An integrated process for the simultaneous alkylation of at least one isoparaffinic hydrocarbon with at least one C.sub.4 olefinic hydrocarbon and at least one isoparaffinic hydrocarbon with at least one olefinic hydrocarbon selected from the group consisting of C.sub.3, C.sub.5 and higher olefinic hydrocarbons and mixtures thereof, comprising: contacting a first alkylatable hydrocarbon comprising an isoparaffinic hydrocarbon with a first alkylating agent comprising at least one olefinic hydrocarbon selected from the group consisting of C.sub.3, C.sub.
    Type: Grant
    Filed: April 5, 1979
    Date of Patent: December 8, 1981
    Assignee: Phillips Petroleum Company
    Inventor: Thomas Hutson, Jr.
  • Patent number: 4286110
    Abstract: The reactor effluent hydrocarbon phase from an alkylation zone in which isoparaffin and olefin are contacted in the presence of HF catalyst to form an alkylate product is treated by (1) separating a hydrocarbon phase from the reacton effluent; (2) separating the hydrocarbon phase in a fractionator to produce a bottoms stream containing isoparaffin, paraffin, and alkylate and an overhead stream containing HF, isoparaffin, and paraffin; (3) flashing this bottoms stream to produce a flashed vapor enriched in isoparaffin and a liquid enriched in alkylate as compared to the bottoms stream; (4) cooling this flashed vapor to produce a condensed liquid; and (5) indirectly contacting this condensed liquid with the overhead stream thereby cooling the overhead stream and heating the condensed liquid.
    Type: Grant
    Filed: January 17, 1980
    Date of Patent: August 25, 1981
    Assignee: Phillips Petroleum Co.
    Inventor: Charles C. Chapman
  • Patent number: 4280880
    Abstract: A process for the separation of isobutane from an alkylation reaction zone hydrocarbon effluent stream comprising isobutane, n-butane, propane and alkylate is disclosed. The hydrocarbon effluent stream is charged to an isostripper column. An isobutane vapor stream from the column is condensed in indirect heat exchange with the lower liquid stream from said column comprising n-butane. The lower liquid stream is flashed in indirect heat exchange with said vapor stream at conditions to provide a vapor phase, said vapor phase being compressed and recycled to said column at a temperature to promote vapor formation therein.
    Type: Grant
    Filed: August 25, 1980
    Date of Patent: July 28, 1981
    Assignee: UOP Inc.
    Inventors: Bipin V. Vora, Anthony G. Vickers
  • Patent number: 4276439
    Abstract: A process and apparatus for the catalytic alkylation of an isoparaffin with one or more olefins. Reactant hydrocarbons are passed in contact with a liquid catalyst such as hydrofluoric acid in a reaction zone. The hydrocarbon phase is allowed to separate from the catalyst phase in a settling zone, and a portion of the hydrocarbon phase is cooled and reintroduced to the reaction zone in a separate stream from that of the feed hydrocarbons. The alkylation apparatus by which the process is carried out includes a vertical reaction vessel, which in a preferred embodiment is 2 to 6 feet in height, a settling vessel, means for fluid flow from the reaction vessel to the settling vessel, a conduit for fluid flow between the upper part of the settling vessel and the reaction zone, and means for cooling fluid in this conduit.
    Type: Grant
    Filed: October 2, 1979
    Date of Patent: June 30, 1981
    Assignee: Phillips Petroleum Company
    Inventors: Thomas Hutson, Jr., Donald J. Makovec, Alden E. Beckworth
  • Patent number: 4275032
    Abstract: A settler-soaking apparatus for treating the effluent from an acid-catalyzed alkylation reaction is disclosed which comprises three interconnected vertically aligned chambers. The uppermost chamber possesses a hydrocarbon outlet means above an acid hydrocarbon inlet means and a downspout having an acid transfer means extending through and ending in the lower end of the middlemost chamber. The latter possesses a hydrocarbon outlet means at an elevated position with respect to the end of the acid transfer means in the downspout and a lower situated acid outlet means. The lowermost chamber possesses a multitude of spaced horizontal perforate trays and an acid hydrocarbon inlet means, which is in connection with the hydrocarbon outlet means of the uppermost chamber. The middle and lowermost chamber are in open communication via a chimney which extends upwardly into said middle chamber to provide a hydrocarbon outlet means at a point above the end of said downspout.
    Type: Grant
    Filed: July 12, 1979
    Date of Patent: June 23, 1981
    Assignee: UOP Inc.
    Inventor: Robert F. Anderson
  • Patent number: 4275255
    Abstract: A hydrocarbon conversion process for the production of motor fuel blending stocks from butanes is disclosed. The butane feed stream enters a deisobutanizer column. A normal butane-rich stream removed from the deisobutanizer is passed into an isomerization zone, with isomerization zone effluent being returned to the deisobutanizer. An isobutane-rich deisobutanizer overhead stream is passed through a dehydrogenation zone which contains a depropanizer and then into an alkylation zone. The effluent of the alkylation zone is fractionated into a product stream and recycle streams passed into the deisobutanizer and the depropanizer. The utilities cost of operating the process is lowered by integration of the heat exchange required in the process.
    Type: Grant
    Filed: January 16, 1980
    Date of Patent: June 23, 1981
    Assignee: UOP Inc.
    Inventor: Bipin V. Vora
  • Patent number: 4249030
    Abstract: Propylene and butylenes are separately acid alkylated with at least one isoparaffin. Expansion and liquid-vapor separation is utilized to separate the propylene from the butylenes. The use of expansion and separation improves the energy efficiency of the alkylation process. The energy efficiency of the alkylation process is further improved by utilizing the bottoms product from the acid stripper associated with the isostripper to cool the acid being supplied to the riser reactor. The size requirements of the isostripper are also reduced by using liquid-vapor separation to remove at least a portion of the unreacted isoparaffin from the alkylated butylenes.
    Type: Grant
    Filed: August 2, 1979
    Date of Patent: February 3, 1981
    Assignee: Phillips Petroleum Company
    Inventors: Charles C. Chapman, Paul D. Hann
  • Patent number: 4243830
    Abstract: The present process is particularly adapted to those situations where a refiner lacks sufficient isobutane to completely alkylate an olefin feedstock. A field butane stream is admixed with an olefin stream, and the mixture is fractionated to provide an isobutane-olefin concentrate and a normal butane concentrate. The former is increased in pressure and reacted in contact with a hydrofluoric acid alkylation catalyst. The latter is introduced into the reaction zone wherein it is vaporized via indirect contact with the warm reaction mixture contained therein. Vaporous normal butane is recycled into the fractionation facility whereby the exothermic heat of the alkylation reaction is utilized to fractionate the first mentioned field butanes-olefin mixture. Alkylation reactions can thus be conducted at subambient temperatures resulting in improved alkylate product quality.
    Type: Grant
    Filed: August 27, 1979
    Date of Patent: January 6, 1981
    Assignee: UOP Inc.
    Inventor: Don B. Carson
  • Patent number: 4239931
    Abstract: A process for the hydrofluoric acid-catalyzed alkylation of an isoparaffin with an olefin in a gravity-flow hydrofluoric acid alkylation reaction system. The process is effected without benefit of an acid regenerator. Regeneration is effected an isostripper column, and catalyst-contaminating polymeric products of the alkylation are recovered in the normally liquid alkylate product substantially free of hydrofluoric acid.
    Type: Grant
    Filed: November 5, 1979
    Date of Patent: December 16, 1980
    Assignee: UOP Inc.
    Inventor: Michael Z. Mikulicz
  • Patent number: 4236036
    Abstract: A continuous process for alkylating an alkylatable hydrocarbon with an alkylating agent in the presence of an acid-type catalyst in which the alkylatable hydrocarbon is contacted with the alkylating agent in the presence of the catalyst at a temperature and for a time sufficient to alkylate the alkylatable hydrocarbon, the reaction product is separated into an alkylate product phase and a catalyst phase, containing catalyst-soluble oil, the catalyst phase is cooled to maintain a preselected temperature in the exothermic alkylation zone, the cooled catalyst phase is recycled to the alkylation reaction and a predetermined concentration of catalyst-soluble oil is maintained in the catalyst phase by at least periodically heating an alkylating agent to a temperature above the reaction temperature, contacting the heated alkylating agent with one of the separated recycle catalyst, separated rerun catalyst, fresh catalyst or mixture thereof and combining the resultant reaction product with separated recycle catalyst
    Type: Grant
    Filed: April 5, 1979
    Date of Patent: November 25, 1980
    Assignee: Phillips Petroleum Company
    Inventors: Rolland E. Dixon, Charles C. Chapman
  • Patent number: 4234750
    Abstract: An improvement is disclosed in a process for the acid-catalyzed alkylation of an isoparaffin with an olefin alkylating agent. The improvement relates to an alkylation process wherein the hydrocarbon phase of the alkylation reaction mixture is introduced into a common fractionation column with a field butane stream comprising olefinic materials. The improvement comprises initially clay-treating said field butane stream.
    Type: Grant
    Filed: August 27, 1979
    Date of Patent: November 18, 1980
    Assignee: UOP Inc.
    Inventor: Michael Z. Mikulicz
  • Patent number: 4225740
    Abstract: A process is provided for the alkylation of isoparaffins with olefins in the presence of an HF acid catalyst comprising separating a liquid hydrocarbon phase from the alkylation effluent, subjecting the hydrocarbon phase to HF stripping, separating the stripped hydrocarbon into a liquid and a vapor phase, fractionating the liquid phase into product streams, and pressurizing the vaporous stream prior to separation of C.sub.3 and lighter materials. The HF alkylation process utilizes indirect heat exchange of various streams and compression of HF-free vapors.
    Type: Grant
    Filed: May 17, 1979
    Date of Patent: September 30, 1980
    Assignee: Phillips Petroleum Company
    Inventors: Charles C. Chapman, Paul D. Hann
  • Patent number: 4225742
    Abstract: In the HF alkylation of isoparaffins with olefins an improved process is provided comprising charging isoparaffin, olefin(s), and HF catalyst to the upstream end of a vertically extended reaction zone, introducing the same or different olefin(s) and, optionally, isoparaffin, downstream along with a recycled alkane stream separated from the alkylation effluent under alkylation conditions to produce high octane alkylate. In a preferred embodiment, the recycle alkane stream is propane and/or normal butane.
    Type: Grant
    Filed: July 13, 1978
    Date of Patent: September 30, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Thomas Hutson, Jr.
  • Patent number: 4225741
    Abstract: A process is provided for the simultaneous and separate alkylation of an isoparaffin such as isobutane with different olefins, e.g., propylenes and butylenes in different zones with an HF acid catalyst comprising separating the hydrocarbon phase from each of the alkylation effluents, subjecting each hydrocarbon phase to separate HF stripping, fractionating the liquid phases removed from each of the HF stripping zones, pressurizing the vaporous isoparaffin stream recovered from fractionation and utilizing the pressurized vaporous streams for indirect heat exchange with HF strippers and fractionation zones prior to recycling through alkylation.
    Type: Grant
    Filed: August 1, 1979
    Date of Patent: September 30, 1980
    Assignee: Phillips Petroleum Company
    Inventors: Charles C. Chapman, Paul D. Hann
  • Patent number: 4220806
    Abstract: A process is disclosed for the alkylation of an isoparaffinic hydrocarbon with an olefin-acting alkylating agent. The isoparaffinic hydrocarbon is commingled with a first portion of said alkylating agent in a first alkylation reaction zone at alkylation reaction conditions in contact with a hydrofluoric acid catalyst. The acid phase of the effluent from the first alkylation reaction zone is separated, and the hydrocarbon phase, comprising alkylate and unreacted isoparaffin, is commingled with a second portion of said alkylating agent at alkylation reaction conditions in a second alkylation reaction zone in contact with a hydrofluoric acid catalyst separately charged thereto, the hydrofluoric acid catalyst being that separated from the effluent of the first alkylation reaction zone. The acid phase is separated from the effluent from the second alkylation reaction zone and recycled to the first alkylation reaction zone, and the alkylate product is recovered from the hydrocarbon phase.
    Type: Grant
    Filed: April 23, 1979
    Date of Patent: September 2, 1980
    Assignee: UOP Inc.
    Inventors: Michael Z. Mikulicz, James F. Himes
  • Patent number: 4218575
    Abstract: Improvements in alkylation effluent flash vaporization systems used in processes of alkylating isoparaffinic hydrocarbons with olefinic hydrocarbons in the presence of acid catalyst and an excess of isoparaffinic hydrocarbons; improvements in heat sources used in such alkylation effluent flash vaporization systems, specifically utilizing hot and compressed isoparaffinic hydrocarbon vapors generally available in such systems from such sources as fractionation (deisobutanizer) overhead or vapor flashing processes utilized in cooling the reaction step or both; improvements in alkylation effluent flash vaporization systems which reduce the load on the conventional step of retrieving excess isoparaffinic hydrocarbons from the alkylation reaction effluent for recycle to the reaction step.
    Type: Grant
    Filed: April 10, 1978
    Date of Patent: August 19, 1980
    Assignee: Stratford/Graham Engineering Corporation
    Inventor: Orlando Webb, Jr.
  • Patent number: 4218574
    Abstract: A process for the acid-catalyzed alkylation of an alkylatable hydrocarbon with an olefin-acting alkylating agent is disclosed. The alkylation reactor effluent is treated in a unitary settler-soaker vessel whereby a substantial reduction in the acid catalyst inventory of the system is effected. A novel combination soaking-settling apparatus is also disclosed.
    Type: Grant
    Filed: July 12, 1979
    Date of Patent: August 19, 1980
    Assignee: UOP Inc.
    Inventor: Robert F. Anderson
  • Patent number: 4214114
    Abstract: A process for the acid-catalyzed alkylation of an isoparaffinic hydrocarbon with an olefinic hydrocarbon is disclosed. The alkylation is effected at alkylation reaction conditions resulting in an alkylation reaction mixture containing a vapor phase generated by the exothermic heat of reaction. The vapor phase so generated has a cooling effect permitting the alkylation reaction to be effected at lower temperatures more conducive to higher quality alkylation product.
    Type: Grant
    Filed: January 26, 1979
    Date of Patent: July 22, 1980
    Assignee: UOP Inc.
    Inventor: Don B. Carson
  • Patent number: 4214115
    Abstract: A cyclic system for the alkylation of an isoparaffin, e.g., isobutane, wherein a first olefinic reactant, e.g., butylene, is used to alkylate the isoparaffin for a first period of time in an alkylation reactor and then a second olefinic reactant, e.g., propylene, is used to alkylate the isoparaffin for a second period of time in the same alkylation reactor. During the period that the isoparaffin is alkylated with the first olefinic reactant, the reactor effluent stream is continuously separated into a liquid hydrocarbon phase comprising alkylation products and unreacted isoparaffin and a liquid acid alkylation catalyst phase. The acid catalyst is continuously recycled to the reactor and the hydrocarbon phase is passed to a first surge zone or holding tank.
    Type: Grant
    Filed: May 9, 1978
    Date of Patent: July 22, 1980
    Assignee: Phillips Petroleum Company
    Inventors: Donald J. Makovec, Thomas Hutson, Jr.
  • Patent number: 4207423
    Abstract: A continuous process for the alkylation of an alkylatable hydrocarbon with an alkylating agent in the presence of an acid-type catalyst, including; contacting an alkylatable hydrocarbon with an alkylating agent in the presence of an acid-type catalyst at a temperature and pressure and for a time sufficient to alkylate the alkylatable hydrocarbon; separating the reaction effluent stream into an alkylate product phase and a catalyst phase containing catalyst-soluble oil; cooling the catalyst phase to a temperature essentially equal to the alkylation reaction temperature; recycling the cooled catalyst phase to the alkylation reaction; contacting a diolefinic hydrocabon with an acid-type catalyst at a temperature and pressure sufficient to form additional catalyst-soluble oil and combining the additional catalyst-soluble oil with the circulating catalyst phase.
    Type: Grant
    Filed: April 5, 1979
    Date of Patent: June 10, 1980
    Assignee: Phillips Petroleum Company
    Inventors: Donald J. Makovec, Donald M. Haskell
  • Patent number: 4205196
    Abstract: A method of alkylating an alkylatable hydrocarbon with different alkylating agents, at different reaction temperatures and in a single reaction zone, in which an alkylatable hydrocarbon is contacted with an acid-type catalyst and at different points in an elongated reaction zone, the reaction zone effluent is separated into a hydrocarbon phase and a catalyst recycle phase and the reaction temperatures of the various alkylating agents are maintained at different temperatures by splitting the recycle catalyst phase into an equal number of streams and adjusting the reaction temperatures by adjusting the temperatures of the recycle catalyst phase streams, the relative proportions of the recycle catalyst phase streams or both. A method of starting-up the process and apparatus for conducting the process are also disclosed.
    Type: Grant
    Filed: April 5, 1979
    Date of Patent: May 27, 1980
    Assignee: Phillips Petroleum Company
    Inventors: Donald J. Makovec, Donald M. Haskell
  • Patent number: 4195191
    Abstract: An improved isoparaffin/olefin HF alkylation process designed to function absent the commonly-utilized acid regenerator. Polymer products, formed during the alkylation reaction, are recovered with the normally liquid alkylate product, substantially free from HF, without effecting degradation in the product quality. In addition to enhanced economic considerations stemming from a reduction in equipment costs, the operational stability of the process is significantly improved.
    Type: Grant
    Filed: March 25, 1976
    Date of Patent: March 25, 1980
    Assignee: UOP Inc.
    Inventor: William G. Boney
  • Patent number: 4182925
    Abstract: In the recovery of ethane and propane from an alkylation of an isoparaffin with an olefin to prevent buildup of ethane and propane in the system, the ethane and propane are taken as a side draw from the conventional HF stripper instead of being vented from the depropanizer or the fractionator overhead accumulator. Considerable ethane, propane and HF are thus saved and equipment costs reduced, especially because fractionator wall thickness can be reduced and because of the elimination of the equipment attendant the venting of the accumulator.
    Type: Grant
    Filed: September 15, 1975
    Date of Patent: January 8, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Charles C. Chapman
  • Patent number: 4182924
    Abstract: An HF alkylation-fractionation system for the separation of the hydrocarbon phase separated from the HF alkylation effluent by passing the hydrocarbon phase first to a prefractionation zone operated at low pressure, followed by fractionation of both overhead and bottoms from the prefractionation zone at higher pressures and temperatures, and utilization of the high temperature streams obtained from the higher pressure fractionations as sources of heat for indirect heat exchange of the prefractionation zone and feed to at least one of the subsequent fractionations.
    Type: Grant
    Filed: June 12, 1978
    Date of Patent: January 8, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Charles C. Chapman
  • Patent number: 4180526
    Abstract: An olefin and isoparaffin are contacted in the presence of an acid alkylation catalyst to form an alkylate-containing alkylation effluent. The effluent is separated with the hydrocarbon phase passing to a prefractionation zone. A side stream from the prefractionation zone is passed in indirect heat exchange relationship with an interheater of an isostripper thereby providing a majority of the heat necessary to reboil the isostripper.
    Type: Grant
    Filed: July 7, 1978
    Date of Patent: December 25, 1979
    Assignee: Phillips Petroleum Company
    Inventor: Charles C. Chapman
  • Patent number: 4167531
    Abstract: In the purification of hydrocarbon streams containing HF by chemical reaction with potassium hydroxide, a small portion of the hydrocarbon stream containing HF is passed through a small test bed of solid KOH; and when excess HF is present in the hydrocarbon stream to be purified, the temperature of the test bed increases significantly and rapidly and the flow of hydrocarbon is discontinued to the main treater responsive to the temperature in the test bed thereby preventing the treater temperature from exceeding a preselected maximum allowable value. In one embodiment, the main hydrocarbon charge is by-passed around the main KOH treater and introduced into the effluent from the treater; and in another embodiment, the hydrocarbon charge is returned to a settling zone following alkylation and prior to separation facilities utilized to process the hydrocarbon phase.
    Type: Grant
    Filed: August 12, 1977
    Date of Patent: September 11, 1979
    Assignee: Phillips Petroleum Co.
    Inventor: Mack F. Potts
  • Patent number: 4167535
    Abstract: Field butanes, otherwise introduced into an isostripping column, also utilized to recover alkylate product from unreacted isobutane, are separately fractionated to provide an isobutane concentrate and a normal butane concentrate. The former is increased in pressure and reacted with the olefinic feed stream in admixture with HF-acid catalyst. The latter is introduced into the reaction zone wherein it is vaporized via indirect contact with the reaction mixture. Vaporous normal butane is introduced into the fractionation facility wherein the exothermic heat of reaction serves to separate the field butane stream. Alkylation reactions can thus be conducted at sub-ambient temperatures which results in an alkylate product of improved quality. This technique also obviates the necessity for a cooling water system, thus eliminating the possibility of HF-acid contamination of water bodies.
    Type: Grant
    Filed: April 24, 1978
    Date of Patent: September 11, 1979
    Assignee: UOP Inc.
    Inventor: Don B. Carson