To Recover Unsaturate Patents (Class 585/809)
  • Patent number: 4915794
    Abstract: This invention relates to a process for producing an olefin product having an enhanced alpha olefin content from an olefin feedstock containing internal olefins or a mixture of internal and alpha olefins which includes:(a) contacting the feedstock with an anthracene and a double-bond isomerization catalyst at a temperature ranging from about 150.degree. to about 275.degree. C. to form an olefin adduct with anthracene,(b) separating the adduct from the product of step (a),(c) heating the separated adduct at a temperature ranging from about 250.degree. to about 400.degree. C. to produce anthracene and an olefin product enhanced in alpha olefin content over the alpha olefin content of the feedstock, and(d) separating anthracene from the product of step (c) to produce the product enhanced in alpha olefin.Linear olefins are a preferred feedstock.
    Type: Grant
    Filed: October 27, 1988
    Date of Patent: April 10, 1990
    Assignee: Shell Oil Company
    Inventors: Lynn H. Slaugh, Howard L. Fong
  • Patent number: 4885063
    Abstract: A process and apparatus are disclosed for recovering olefins, particularly C.sub.3, C.sub.4, and C.sub.5 olefins, from gaseous mixture thereof with lower-boiling components. The olefin-containing gas mixtures is compressed and cooled to yield vapor and condensate streams, the vapor stream is further cooled forming additional condensate, both condensate streams are combined and adiabatically flash evaporated, and the remaining liquid is distilled to recover the desired olefins in a liquid bottoms products. Flash vapor, and optionally the distillation vapor product, are recycled to the compression step.
    Type: Grant
    Filed: October 19, 1988
    Date of Patent: December 5, 1989
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Robert S. Andre
  • Patent number: 4795835
    Abstract: The process relates to the removal of copper contaminants from crude polyacetylenes containing up to 30 wt. % copper impurity by contacting a melt of the polyacetylene with aqueous hydrogen chloride to form an oil phase and an aqueous acid phase, separating said phases, treating the separated oil phase with from about 1 to about 10 volumes of water until subsequent oil and water phases are formed, agitating the separated oil phase while cooling to form a particulate product and drying said particles to recover purified polyacetylene.
    Type: Grant
    Filed: March 3, 1988
    Date of Patent: January 3, 1989
    Assignee: GAF Corporation
    Inventor: Robert Schenfele
  • Patent number: 4788379
    Abstract: The process relates to the recovering of essentially pure acetylene from the gaseous out-put stream from a coal to acetylene conversion process. A plasma arc generator or other high energy type reactor can be used for the conversion to coal. The gaseous out-put stream is initially treated in an acid gas removal stage by absorbing HCN and H.sub.2 S in an organic solvent such as N-methyl pyrrolidone and scrubbing with a caustic agent such as NaOH to remove CO.sub.2. In a second stage, the gaseous out-put stream is scrubbed with the organic solvent to provide a sweet gas treatment and remove essentially pure acetylene as a product. In a third stage, the second stage gases are first hydrogenated, then desulfurized and then methanated. The out-put from the third stage is recycled to the coal to acetylene conversion process. In a fourth stage, the organic solvent from said second stage is refined and recycled to the first stage and/or second stage.
    Type: Grant
    Filed: October 1, 1982
    Date of Patent: November 29, 1988
    Assignee: GAF Corporation
    Inventors: Michael Katz, Frank Carluccio, Gil Mallari, Kevin FitzPatrick, Ashok Desai, Robert Casciano, Jane Tsai
  • Patent number: 4762897
    Abstract: In a copolymerization process of propylene, a mixture of unreacted propylene and ethylene is recovered. It is then fed to a distillation system which includes first and second distillation columns. The distillation system is operated in such a way that the temperature and pressure of the top of the second distillation column remain constant and an ethylene-propylene mixture can be recovered at a constant ethylene/propylene ratio from the top of the second distillation column. By using the thus-recovered ethylene-propylene mixture, the copolymerization reaction can be carried out under excellent control so that the ethylene-propylene copolymer can be obtained with uniform quality and properties.
    Type: Grant
    Filed: April 29, 1987
    Date of Patent: August 9, 1988
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Tadashi Asanuma, Yoshiyuki Funakoshi, Tatuo Ohoka
  • Patent number: 4735704
    Abstract: An improved process for removing free liquid from a hydrocarbon-rich gas stream is disclosed. Liquid is injected into the gas stream upstream of a chiller and downstream of an acid-gas removal system and any equipment that may affect the water content of the gas stream: compressors, columns, additional knockout drums, heat exchangers or the like. This enhances heat and mass transfer in a manner that both minimizes the formation of small droplets and encourages the coalescence of small droplets in the chiller. As a result, small droplets which would normally pass through a knockout drum and a standard mist eliminator are increased in size, prior to their arrival at a vapor-liquid separator to larger drops which are easily removed by the vapor-liquid separator, and the mist eliminator.
    Type: Grant
    Filed: May 16, 1986
    Date of Patent: April 5, 1988
    Assignee: Santa Fe Braun Inc.
    Inventors: Henry Z. Kister, James F. Litchfield
  • Patent number: 4734273
    Abstract: A process is disclosed for selectively sorbing trace amounts of oxygen from low molecular weight olefins and inert gases by contacting with high surface area particulate coal-derived activated carbon having high ash and moisture content.
    Type: Grant
    Filed: December 29, 1986
    Date of Patent: March 29, 1988
    Assignee: Shell Oil Company
    Inventor: Weston W. Haskell
  • Patent number: 4718986
    Abstract: High purity butene-1, in particular polymerization grade butene-1, is obtained by means of a two-stage fractionation of a C.sub.4 hydrocarbon stream comprising butene-1 which is substantially free from butadiene.The first stage of the fractionation process allows practically all the isobutane contained in the C.sub.4 batch to be separated as the top stream.The bottom phase of the first stage of fractionation is supplied to the second stage of fractionation thus obtaining high purity butene-1 as the top fraction, and the remaining components as the bottom phaseAccording to the process of the invention, vapors of butene-1 obtained as the top stream from the second stage of fractionation are compressed and the resultant heat of condensation is used for operating the reboilers of the two fractionation stages.
    Type: Grant
    Filed: September 4, 1986
    Date of Patent: January 12, 1988
    Assignee: Snamprogetti, S.p.A.
    Inventors: Renzo Comiotto, Bruno De Maglie
  • Patent number: 4673768
    Abstract: An improved method for the separation of polymer from hydrocarbon solvent in a process for the manufacture of poly-.alpha.-olefins is disclosed. A solution of polymer and solvent at a temperature above 130.degree. C. and a pressure above atmospheric pressure is passed through pressure reduction means into a vessel. Solvent is flashed off and the polymer forms a pool of molten polymer. The temperature of the walls of the vessel above the pressure reduction means is maintained at least 10.degree. C., and especially at least 30.degree. C., above the temperature of the walls of the remainder of the vessel. The improved method is less susceptible to the formation of gel in the polymer.
    Type: Grant
    Filed: March 7, 1986
    Date of Patent: June 16, 1987
    Assignee: Du Pont Canada Inc.
    Inventor: John N. Yeates
  • Patent number: 4558168
    Abstract: This invention relates to a process for producing a high purity butene-1 product from n-butane via a dehydrogenation process. In one embodiment of the process the n-butane is dehydrogenated over a chromia-alumina catalyst and any butadiene formed hydrogenated to monoolefins. The monoolefins are separated and the butene-1 separated from isobutylene by reacting the isobutylene with methanol to form methyl tertiary butyl ether. The methyl tertiary butyl ether is separated from the butene-1 leaving it as a high purity product. Alternatively, the dehydrogenated product from the reactor may be contacted with a solvent to extract butadiene followed by hydrogenation, separation of monoolefins and conversion to methyl tertiary butyl ether.
    Type: Grant
    Filed: June 19, 1985
    Date of Patent: December 10, 1985
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Stanley Gussow, David C. Spence, William A. Schwartz
  • Patent number: 4556461
    Abstract: A process for separating a butene-1/isobutene mixture from a C.sub.4 hydrocarbon fraction is provided which comprises subjecting the C.sub.4 hydrocarbon fraction to extractive distillation using a polar solvent to separate components predominantly containing 1,3-butadiene as an extract and obtain an overhead containing butanes, butene-1, isobutene and butene-2 as main components and being substantially free from C.sub.3 -C.sub.4 diolefinic and acetylenic hydrocarbons, feeding the overhead into a first distillation column, removing isobutane as an overhead component from the first distillation column, feeding high-boiling components from the bottom of the first distillation column to a second distillation column, removing n-butane and butene-2 from the bottom of the second distillation column, and obtaining highly pure butene-1 and isobutene from its top.
    Type: Grant
    Filed: December 1, 1982
    Date of Patent: December 3, 1985
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Shunichiro Ogura, Masamichi Soumai
  • Patent number: 4555312
    Abstract: A process for separating a butene-1/isobutene mixture from a C.sub.4 hydrocarbon fraction is provided which comprises subjecting the C.sub.4 hydrocarbon fraction to extractive distillation using a polar solvent to separate components predominantly containing 1,3-butadiene as an extract bottom and obtain an overhead containing butanes, butene-1, isobutene and butene-2 as main components and being substantially free from C.sub.3 -C.sub.4 diolefinic and acetylenic hydrocarbons, feeding the overhead into a first distillation column, removing n-butane and butene-2 as bottoms from the column, feeding low-boiling components from the top of the column into a second distillation column, removing isobutane from the top of the second distillation column, and obtaining highly pure butene-1 and isobutene from its bottom.
    Type: Grant
    Filed: November 23, 1982
    Date of Patent: November 26, 1985
    Assignee: Nippon Zeon Co. Ltd.
    Inventors: Shunichiro Ogura, Masamichi Soumai
  • Patent number: 4554390
    Abstract: A method for harvesting algae of the genus Dunaliella from suspensions thereof in brines containing sodium chloride at a concentration of about 3M or above, wherein the algal suspension is contacted with an adsorbent having a hydrophobic surface so as to adsorb the algae thereon, and the adsorbent with the algae adsorbed thereon is separated from the brine..beta.-carotene and other useful cell components may be extracted from the adsorbed algae by treatment with a suitable solvent.
    Type: Grant
    Filed: June 7, 1983
    Date of Patent: November 19, 1985
    Assignees: Commonwealth Scientific and Industrial Research Organization, Betatene Limited
    Inventors: Cyril C. Curtain, Harvey Snook
  • Patent number: 4526657
    Abstract: In a fractional distillation process in which it is desired to maintain a desired overhead product composition and bottoms product composition, a set point for the flow rate of the external reflux to the fractional distillation column is increased or decreased by an incremental amount or is left constant based on whether the concentration of the heavy key component in the overhead product stream and the concentration of the light key component in the bottoms product stream are above a high limit, below a low limit, between the high limit and low limit or some combination thereof. At the same time, a temperature set point for the fractional distillation column is increased or decreased by an incremental amount or is left constant depending on the same factors. Use of these set points for process control provides control of the overhead product composition and bottoms product composition without the use of analysis controllers.
    Type: Grant
    Filed: October 29, 1982
    Date of Patent: July 2, 1985
    Assignee: Phillips Petroleum Company
    Inventors: James W. Hobbs, Mary M. Halliday
  • Patent number: 4515661
    Abstract: A process for separating highly pure butene-2 and butene-1 from a C.sub.4 hydrocarbon fraction containing isobutane, n-butane, butene-1, butene-2, and at least one diolefinic hydrocarbon and/or at least one acetylenic hydrocarbon, which comprises, (1) as a step A, treating the C.sub.
    Type: Grant
    Filed: September 21, 1982
    Date of Patent: May 7, 1985
    Assignee: Nippon Zeon Co. Ltd.
    Inventors: Shunichiro Ogura, Masamichi Soumai
  • Patent number: 4474647
    Abstract: A C.sub.4 and/or C.sub.5 olefinic hydrocarbon cut, containing dimethyl ether and water as impurities, in a relative proportion of dimethyl ether to water of at most 5:1, is purified in a distillation zone where it is introduced at an intermediate level, distant from the top or from the bottom thereof by at least 3 theoretical plates, optionally with a stripping gas, and separated into a overhead fraction comprising an aqueous liquid phase and a hydrocarbon liquid phase at least partially recycled as reflux to the upper part of the distillation zone, and a bottom fraction formed of the purified C.sub.4 and/or C.sub.5 olefinic cut.
    Type: Grant
    Filed: April 23, 1982
    Date of Patent: October 2, 1984
    Assignee: Institut Francais du Petrole
    Inventors: Lionel Asselineau, Jacques Leonard, Jean Chodorge, Jean Gaillard
  • Patent number: 4421607
    Abstract: A process of extractive distillation for separating components easily soluble in a polar solvent from at least two hydrocarbon mixtures having different contents of the easily soluble components by extractive distillation using said polar solvent, which comprises feeding a hydrocarbon mixture containing a larger amount of the easily soluble components, as a gas, into the middle or lower portion of an extractive distillation column, feeding a hydrocarbon mixture containing a smaller amount of the easily soluble components, as a liquid, to the upper portion of the extractive distillation column, and subjecting them to extractive distillation.
    Type: Grant
    Filed: February 1, 1983
    Date of Patent: December 20, 1983
    Assignee: Nippon Zeon Co. Ltd.
    Inventor: Shunichiro Ogura
  • Patent number: 4410754
    Abstract: An olefin isomerization process useful in recovering isobutylene from mixed butylene feed streams is disclosed. Preferably, the feed stream is passed through a first reaction zone to convert some butene-1 to butene-2 and then fed to the lower part of a two-part fractionation system. The butene-2-rich bottoms is withdrawn and the overhead vapor is passed through a second reaction zone in admixture with hydrogen before entering the second or upper part of the fractionation system. The bottoms liquid of the upper part of the fractionation system flows into the lower part of the fractionation system. Isobutylene and recycle hydrogen are recovered from the overhead vapor of the upper part of the fractionation system.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: October 18, 1983
    Assignee: UOP Inc.
    Inventor: Steve A. Gewartowski
  • Patent number: 4409421
    Abstract: Pure tert.-olefins are prepared from mixtures of hydrocarbons, which contain at least one such tert.-olefin, by reaction with an alkanol to give the corresponding alkyl tert.-alkyl ethers, and subsequent cleavage of these ethers back to the corresponding pure tert.-olefins and the alkanol, and the separation of the pure tert.-olefin from the alkanol. For this, the alkanol present after the cleavage of the ether is separated from the tert.-olefin to the extent of 60 to 99% by weight by distillation, and the residual amount of alcohol in the olefin fraction is removed by adsorption from this fraction onto a synthetic ion exchanger as an absorber resin. The admixture of the alkanol to the mixture of hydrocarbons with at least one tert.-olefin is carried out partly by using the alkanol fraction arising from the separating off of the pure tert.-olefin, and partly by desorption of the alkanol from the absorber resin with the aid of the mixture of hydrocarbons containing at least 1 tert.-olefin.
    Type: Grant
    Filed: June 4, 1982
    Date of Patent: October 11, 1983
    Assignees: EC Erdolchemie GmbH, Bayer Aktiengesellschaft
    Inventors: Jens Herwig, Bruno Schulwitz, Bernhard Schleppinghoff, Hans-Volker Scheef, Peter M. Lange
  • Patent number: 4387259
    Abstract: Aromatic hydrocarbons are selectively alkylated using an alkylating mixture containing both ethylene and propylene. By employing a zeolite ZSM-12 based alkylation catalyst, essentially only the propylene from the olefin-containing alkylation mixture will react with the aromatic hydrocarbon to thereby form both an alkylaromatic product enriched in propylated alkylaromatic and a propylene-free residual olefin-containing mixture enriched in the unreacted ethylene.
    Type: Grant
    Filed: July 16, 1981
    Date of Patent: June 7, 1983
    Assignee: Mobil Oil Corporation
    Inventor: George C. Barile
  • Patent number: 4371426
    Abstract: In a fractional distillation column in which at least a first component and a second component are at least partially separated with the first component being removed principally as an overhead product and the second component being removed principally as a bottoms product and in which the heat supplied to the fractional distillation column is used as the primary control for the overhead product composition with the flow rate of external reflux to the fractional distillation column being used to control the bottoms product composition, a comparison of the actual concentration of the second component in the overhead product to the desired concentration is utilized to bias the control signal which is utilized to manipulate the flow rate of the external reflux to the fractional distillation column.
    Type: Grant
    Filed: August 17, 1981
    Date of Patent: February 1, 1983
    Assignee: Phillips Petroleum Company
    Inventors: Robert J. DiBiano, James W. Hobbs
  • Patent number: 4367363
    Abstract: The process relates to the recovering of essentially pure acetylene from the gaseous out-put stream from a coal to acetylene conversion process. A plasma arc generator or other high energy type reactor can be used for the conversion to coal. The gaseous out-put stream is initially treated in an acid gas removal stage by absorbing HCN and H.sub.2 S in an organic solvent such as N-methyl pyrrolidone and scrubbing with a caustic agent such as NaOH to remove CO.sub.2. In a second stage, the gaseous out-put stream is scrubbed with the organic solvent to provide a sweet gas treatment and remove essentially pure acetylene as a product. In a third stage, the second stage gases are first hydrogenated, then desulferized and then methanated. The out-put from the third stage is recycled to the coal to acetylene conversion process. In a fourth stage, the organic solvent from said second stage is refined and recycled to the first stage and/or second stage.
    Type: Grant
    Filed: December 23, 1980
    Date of Patent: January 4, 1983
    Assignee: GAF Corporation
    Inventors: Michael Katz, Frank Carluccio, Gil Mallari, Kevin FitzPatrick, Ashok Desai, Robert Casciano, Jane Tsai
  • Patent number: 4356339
    Abstract: A process for isolating and recovering butene-1 of high purity at a high yield is provided. The process comprises the steps of continuously passing a butane-butene fraction containing 0.1 to 15 wt % of isobutylene and 10 to 50 wt % of butene-1 through a first reactor packed with a strongly acidic cation exchange resin having an average particle size of from 0.2 to 10 mm at a temperature of from 30.degree. to 100.degree. C. and at a space velocity of liquid of from 0.1 to 50 hr.sup.-1 under a pressure of from 1 to 50 atm., dividing the output mixture flowing out of said first reactor into two flows at a division ratio in flow rate of 1.about.15:1, recirculating the first flow having the flow rate of 1.about.
    Type: Grant
    Filed: December 7, 1981
    Date of Patent: October 26, 1982
    Assignee: Nippon Oil Company, Limited
    Inventors: Masao Imaizumi, Tetsuya Takezono, Takaaki Amari, Yutaka Oguchi
  • Patent number: 4208540
    Abstract: A process for the continuous separation and recovery of isobutene from an isobutene-containing hydrocarbon mixture, comprising the steps of contacting the mixture with water to obtain a tertiary butanol-containing mixture, separating this mixture into hydrocarbon and aqueous layer, distilling the hydrocarbon layer to obtain a tertiary butanol-rich stream, dehydrating the thus obtained stream to obtain an isobutene-containing gaseous mixture and then introducing the thus obtained mixture into a distillation means to recover isobutene as the product therefrom.
    Type: Grant
    Filed: May 29, 1979
    Date of Patent: June 17, 1980
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Masao Imaizumi, Mitsuo Yasuda, Ko Sakata, Noboru Hirano
  • Patent number: 4154770
    Abstract: This invention relates to an improved process for the alkylation of olefins in an alkylation unit feed stream in order to produce a higher yield of alkylate having a higher octane number, a lower acid consumption rate, and a lower energy consumption. Such a process involves passing a feed stream comprised of olefins and paraffins through a membrane so that the olefins are separated from the paraffins. In passing through the membrane, the olefins are facilitated in their transport by an isoparaffin sweep stream and together, the olefin/isoparaffin stream is passed into an alkylation reactor. Within the reactor, the olefins react with the isoparaffins to form alkylate.
    Type: Grant
    Filed: June 28, 1978
    Date of Patent: May 15, 1979
    Assignee: Standard Oil Company (Indiana)
    Inventor: Richard D. Kaplan