US2920037A - Separation of normal paraffins from hydrocarbon mixtures using zeolitic molecular sieves - Google Patents

Separation of normal paraffins from hydrocarbon mixtures using zeolitic molecular sieves Download PDF

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Publication number
US2920037A
US2920037A US568809A US56880956A US2920037A US 2920037 A US2920037 A US 2920037A US 568809 A US568809 A US 568809A US 56880956 A US56880956 A US 56880956A US 2920037 A US2920037 A US 2920037A
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normal
normal paraffin
line
sorbed
desorbent
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Haensel Vladimir
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Universal Oil Products Co
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Universal Oil Products Co
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Priority to NL108239D priority Critical patent/NL108239C/xx
Application filed by Universal Oil Products Co filed Critical Universal Oil Products Co
Priority to US568809A priority patent/US2920037A/en
Priority to CA723,889A priority patent/CA1016873A/en
Priority to DE19571795548 priority patent/DE1795548B2/de
Priority to GB6684/57A priority patent/GB803184A/en
Priority to DE1418428A priority patent/DE1418428C2/de
Priority to ES0233939A priority patent/ES233939A1/es
Priority to FR1172788D priority patent/FR1172788A/fr
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
    • C10G25/02—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents with ion-exchange material
    • C10G25/03—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents with ion-exchange material with crystalline alumino-silicates, e.g. molecular sieves
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
    • C07C7/13—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers by molecular-sieve technique

Definitions

  • This invention relates to a method of separating normal parafiins from a hydrocarbon mixture containing the same. It is more specifically .concerned with a sorption-desorption process which is particularly suitable for the separation of normal paraffins from a hydrocarbon mixture containing the same.
  • Normal paraflins find use as intermediates or raw materials in the production of many petro-chemicals. Normal paraffins also find wide use as solvents. While normal parafiins are not particularly desirable for use as a motor fuel, because of their relatively low octane numbers they may readily be isomerized to isoparaflins which have substantially higher octane numbers. Since isomerization is an equilibrium reaction, it is preferred that the normal paraffins be separated from isoparaffins before subjecting the normal parafiins to isomerization. In this manner, isomerization of the normal-paraflins occurs without theequilibrium restrictions imposedby the presence of isoparaffins in the feed.
  • the process of the present invention may also be used to increase the octane number of gasolines.
  • a gasoline having an octane number of 85 F-l clear and containing normal parafiins, having an average octane number of zero would have an octane improvement from 85 to 94.5 by removal of these normal paraflins, on a strictly arithmetical basis.
  • the normal parafiins are removed from the gasoline thereby increasing the octane number.
  • the normal parafiins separated from the gasoline may be subjected to a further treatment to convert them to aromatics and/or isoparaflins which may be blended into gasoline.
  • the present invention relates to a process which comprises contacting in a sorption zone a hydrocarbon mixture containing normal paraffins with a solid sorbent-having a high sorbing power for normal paraffins, withdrawing and recovering from said sorption zone a hydrocarbon mixture of decreased normal paraffin content, anddesorbing the normal parafins sorbed on the solid sorbent by displacing them with a normal paraflin.
  • the present invention relates to a process which comprises contacting in a sorption zone a hydrocarbon mixture containing normal paraffins and isoparafiins with "a solid sorbent having a higher sorbing power for normal paraffins than for isoparaffins at a temperature within the range of from about 175 F. to'about 305 9 F., withdrawing from said sorption zone a hydrocarbon mixture of decreased normal parafiin content, discontinuing the introduction of the hydrocarbon mixture to said sorption zone and thereafter introducing a normal paraflin to said sorption zone, which normal parafiin selectively removes the sorbed normal paraifins from said solid sorbent and recovering the desorbed normal paraffins.
  • the present invention relates to a process for separating normal paraflins from a hydrocarbon mixture containing normal paraflins, isoparaffins and aromatics which comprises introducing said mixture to a sorption zone and therein contacting said mixture with a crystalline alumino-silicate at a temperature within the range of from about 175 F. to about 305 F.
  • the effluent from the sorption zone therefore, has a reduced-normal parafiin content, when compared with the charge to the sorption zone.
  • the introduction of the hydrocarbon mixture to the sorption zone is discontinued, and the normal paraffins are removed from the sorbent.
  • reformate contains a small amount of normal paraffins having relatively low octane numbers.
  • the presence of these parafiins is due to the fact that under operating conditions of reforming, the equilibrium concentration represents a fair concentration of normal paraflins.
  • the effect of the normal paraflins in the reformate is to cause a substantial depression of the octane number of the reformate.
  • the charge stocks that may be treated in accordance with my invention comprise hydrocarbon mixtures containing normal paraffins.
  • the mixture may be of normal parafiins and isoparaffins; normal paraffins and cycloparafiins', normal paraflins and aromatics; normal paraftins, isoparaffins and cycloparaflins; normal paraflins, isoparaffins and aromatics; normal paraflins, cycloparaifins and aromatics; etc.
  • the charge to the sorption zone does not contain hydrocarbons boiling below normal butane. The reason for this will be discussed further in the specification. Petroleum hydrocarbons, for example, gasolines, naphthas, etc. are mixtures containing normal paraffins, and these mixtures may be treated in accordance with the present invention.
  • the contact of the hydrocarbon mixture containing normal parafiins in the sorption zone is with a solid sorbent. which has a selective sorbing power for normal paraffins.
  • the contact is for a time sufficient to sorb a substantial amount of the normal parafiins present in the charge.
  • the sorption tower is maintained at a temperature andpressure so that the charge is maintained in the liquid phase. As will be hereinafter further elaborated upon, it is preferred to maintain the temperature in the sorption zone within the range of from about 175 F. to about 305 F. With a hydrocarbon charge mixture boiling substantially within the gasoline boiling range, the pressure in the sorption zone is within the range of from about 200 to about 1000 p.s.i.g., to keep the charge in the liquid phase.
  • any suitable solid sorbent material may be used.
  • the solid sorbent in the sorption zone is one that has a higher sorbing power for normal paraflins than for other hydrocarbons.
  • Alumino-silicates such as calcium alumino-silicate, magnesium alumino-silicate, barium alumino-silicate, sodium alumino-silicate, potassium alumino-silicate, strontium alumino-silicate', etc. are suitable solid sorbents to use although they do not necessarily provide equivalent results. Crystalline calcium aluminosilicates, which have been heated to remove the water of hydration are preferred.
  • the contact of the charge with the solid sorbent is for a time sufficient to sorb substantial quantities of the normal parafiins from the charge. After a substantial quantity of the normal paraflins are sorbed, the sorbed normal paraflins are removed and recovered from the solid sorbent.
  • the usual procedure for removal of the sorbed normal parafiins is by heating under vacuum. Such a procedure involves a considerable expenditure with respect to both initial installation and operating cost.
  • the present invention in its preferred embodiment, provides for a simple and essential isothermal operation of the sorption and desorption cycle. This results in a great saving in operating cost and the equipment necessary for the operation is simple and readily available.
  • the normal paraffin which selectively removes, or displacesthe sorbed normal paraflins may be normal buetc. although they do not necessarily produce equivalent results.
  • Normal butane is a specifically preferred displacing agent since it is readily available. Its use has further advantages, in that it is a relatively cheap refinery product, and the process using normal butane is tane, normal pentane, normal-hexane, normal heptane, more efficient, economical and far more simple than any using the higher boiling normal paraflins.
  • a lower temperature and generally a lower pressure may be used with normal butane which results in heat saving and a saving in investment and equipment.
  • the pressure preferably is within the range of from about 400 to about 600 pounds per square inch gauge!
  • the temperature is preferably only slightly below the critical temperature of normal butane and the pressure is sufficient to maintain the normal butane as-a liquid.
  • the critical temperature for normal butane is 305.6" F. and the critical pressure is 550 p.s.i.g. The temperature should, therefore, be below 305 F. and genarally within the 305 F. range and more preferably fromabout 250 F. to about 305 F.
  • the sorbed normal paraffins are removed from the sorbent material by passing into contact with the solid sorbent material a liquid normal paraffin which selectively removes the sorbed normal parafiins from the sorbent and the sorbed normal paratiins are removed and recovered.
  • the sorption zone being maintained at 'a temperature within the range of from about 175 F; to about 305 F.
  • the introduction of the charge is discontinued and liquid normal butane is introduced to the sorption zone which is maintained at conditions within ranges of temperature and pressure mentioned for the sorption cycle so that the normal butane is maintained in the liquid phase.
  • the solid sorbent material may be removed from the sorption zone and the treatment with the normal butane may take place in a separate zone. The normal butane displaces the heavier sorbed normal parafiins and the desorbed C plus sorbed paraffins are displaced from the solid sorbent and finally recovered.
  • the pressure onthe sorption tower is lowered to permit the vaporization of the normal butane from the system. Since the vaporization is conducted at nearly the critical temperature and pressure for the normal butane stream; there is essentially no heat of vaporization, and, therefore, the unit remains at essentially the same operating temperature. Following this vaporization of the normal butane, the charge may again be introduced to the sorption zone and more heavier than butane, that is more C plus normal parafiins may be sorbed on the solid sorbent material.
  • normal butane In the operation wherein normal butane is displacing the C plus normal parafiins from the solid sorbent material the efliuent from the zone, which is predominantly normal paraflins, is passed to a fractionator.- In the fractionator the normal butane is fractionated from the heavier hydrocarbons and from lighter hydrocarbons when they are present. The normal butane recovered from the fractionator may be passed to a sorption zone. to displace more C plus normal paraflins and this recycling of the normal butane in the process is an advantage. As hereinbefore mentioned, normal butane may;
  • Fractionator 2 is used since even though the charge stream has a high initial boiling point there may be some isobutane and lighter hydrocarbons dissolved in the gasoline fraction and it is desirable to remove these by fractionation prior to contact with the solid sorbent.
  • the normally gaseous material which includes hydracarbons containing from 1 to 4 carbon atoms per molecule, is separated from the hydrocarbon liquid comprising aromatic hydrocarb ons, cycloparafiins, isoparaffins and normal paraffins.
  • the temperature, pressure, and reflux ratio on the fractionator 2 are regulated so as to remove isobutane and lighter components from the charge in line 1 while re taining normal butane-in the liquid bottoms.
  • the gaseous material passes overhead through line 3 into cooler 4 wherein a portion of the material is condensed and the entire stream passes through line 5 into receiver 6.
  • receiver 6 the gas phase and the liquid phase of the overhead material separate.
  • the gases pass through line 7 from which they may be vented to the atmosphere or otherwise used;
  • the fractionator 2 has heat provided thereto by reboiler 10 and connecting lines 9 and 11.
  • Fractionator 2 and receiver 6 are operated at a sufiicient pressure to liquefy at least a portion of the overhead material so that a liquid reflux stream is available to improve'the operationin fractionator 2.
  • The'liquid reflux passes from'receiver 6 through line 8 into. upper. portion of fractionator 2.
  • the bottoms which are withdrawn from fractionator 2 through line 12 contain hydrocarbons boiling above isobutane and the hydrocarbons comprise paraflinic, isoparaffinic, cycloparaflinic and aromatic hydrocarbons.
  • the hydrocarbon mixture in line 12 may be passed through either sorption zone 19 or sorption zone 20. In this illustration it will be considered that the charge in line 12 was previously passed through sorption zone 20 and now the charge is being passed into sorption zone 19. Valve 16 in line 14 is, therefore, closed and valve 15 in line 13 is maintained open. The hydrocarbon mixture in line 12 continues through line 13, valve 15 and line 17 into sorption zone'19.
  • sorption zone 19 the hydrocarbon mixture is contacted with a crystalline calcium alumino-silicate which had previously been heated to remove the water of hydration.
  • This sorption material sorbs normal parafiins from the hydrocarbon mixture and allows the isoparafiins, cycloparaffins and aromatics to pass from the sorption zone through line 21.
  • the sorption zone is maintained at 295 F. and 550 pounds per square inch gauge.
  • the liquid volume space velocity is 1.0.
  • the efiluent from the sorption zone 19 when withdrawn through line 21 has a decreased normal paraffin content when compared with the charge in line 17.
  • the material in line 21 continues through line 23 containing open valve 25 and then through line 31.
  • the material 6 in line 31 consists predominantly of aromaticspcycloparaffins and isoparafiins and contains less than 1% normal paraffins and when tested as a motor fuel it is found to be of higher octane number and has better road performance characteristics than the charge in line 12.
  • the sorption material in sorption zone 19 picks up substantial amounts of normal parafins.
  • the charge stream in line 12 was passed through sorption zone 20 previously and that, therefore, the solid sorption material in zone 20 has substantial amounts of normal paraffins sorbed thereon. 1
  • Valve 35 in line 33 and valve 16 in line 14 are maintained closed and, therefore, a normal butane stream in line 50 continues through line 34, open valve 36 and line 18 into the lower portion of sorption zone 20 and the liquid normal butane displaces the C plus sorbed normal paraffius on the crystalline calcium aluminosilicate.
  • chamber 20 is maintained at a temperature of 295 F. and a pressure of 550 pounds per square inch gauge.
  • the efliuent from chamber 20 which is withdrawn through line 22 during this desorbing operation contains predominantly normal parafiinic hydrocarbons.
  • Liquid normal butane is continued into chamber 20 through line 18 until substantially all of the C plus sorbed normal parafiins are displaced from the solid sorbent.
  • the C plus normal paraffins continue through line 28 containing open .valve 30 and then through line 32 into fractionator 40.
  • the pressure on sorption zone 20 is then reduced to 300 pounds per square inch gauge, thereby vaporizing the liquid normal butane in chamber 201'
  • the charge in line 12 may be introduced into chamber 20 and a desorbing operation started on chamber 19. This may be accomplished by closing valve 36 in line 34 and closing valves 15 and 30 and opening valves 16 and 26. In this operation the charge passes through line 14, open valve 16 and line 18 into sorption zone 20.
  • the effluent from sorption zone 20 continues through line 22, line 24: containing open valve 26 and then through line 31 from which the material has recovered as product.
  • Sorption zone 19 is now ready for the desorption cycle.
  • valves 15 and 25 are closed and valves 35 and 29 are maintained in an open position.
  • theliquid normal butane in line 50 continues through line 33, open valve 35, line 17 and into zone 19.
  • the eflluent which comprises chiefly normal paraflinic hydrocarbons during the desorption cycle, is withdrawn through line 21, con tinues'throu'gh line 27 containing open valve 29 and then through line 32 into fractionator 40.
  • zone 19 is again ready for a sorption cycle.
  • the normal paraffins in line 32 are introduced into fractionator 40.
  • Fractionator 40 is operated as a debutanizer. Since fractionator 2 was operated so as to remove isobutane and lighter materials, normal butane is the lightest hydrocarbon material present in the feed in line 32.
  • Fractionator 40 has heat provided thereto by reboiler 52 and connecting lines 51 and 53.
  • the overhead material is withdrawn from fractionator 40 through line 41 and continues through cooler 42 wherein the entire normal butane fraction is condensed and the liquid fraction in line 43 is passed into overhead receiver 44.
  • the liquid normal butane is withdrawn from receiver 44 through line 45. A portion of this material may be used as reflux on column 40 and passes to an upper portion of fractionator 40 through line 46.
  • a portion of the normal butane in line 47 may be withdrawn through line 48 containing valve 49.
  • the remainder of the liquid normal butane stream continues through line 50 and is used as the desorbing liquid.
  • zone 20 was on a desorption cycle while zone 19 was on a sorption' cycle
  • valve 35 in line 33 was maintained closed and valve 36 was open.
  • the liquid normal butane material therefore, continued through line 34, open valve 36 and line 18 into zone 20, wherein the liquid normal butane is used to displace C and heavier paraffins.
  • a C plus normal paraflin stream is withdrawn from fractionator 40 through line 54.
  • This normal paraffin stream may be used directly as a product or may be subjected to further chemical or catalytic treatment.
  • a process for separating a normal paraffin from a hydrocarbon mixture boiling in the gasoline range containing said normal paraifin and a hydrocarbon selected from the group consisting of branched chain and cyclic hydrocarbons which comprises contacting said mixture at a pressure sufficient to maintain the same in a substantially liquid phase with a dehydrated metal aluminosilicate sorbent having pores of about 5 Angstrom units in cross-sectional diameter, capable of selectively sorbing normal paraflins and of rejecting branched chain and cyclic hydrocarbons, withdrawing a non-sorbed liquid hydrocarbon stream of decreased normal paraflin content from a resulting sorbent containing sorbed normal parafiin, thereafter contacting said sorbent containing sorbed normal paraflin with a desorbent normal paramn of at least 4 carbon atoms per molecule and of lower molecular weight than said first-mentioned normal paraflin at a pressure at which said desorbent normal paraflin is maintained in substantially liquid phase to thereby.
  • a process for separating normal pentane from a hydrocarbon mixture containing the same and isopentane which comprises contacting said mixture with a dehydrated crystalline calcium aluminosilicate containing pores having a cross-sectional diameter of about 5 angstrorn units, capable of selectively sorbing said normal pentane while rejecting said isopentane at a pressure at which said mixture is maintained in substantially liquid phase, withdrawing a hydrocarbon product of decreased normal pentane content from the resulting calcium aluminosilicate containing sorbed normal pentane, thereafter contacting the silicate containing sorbed normal pentane with normal butane at substantially the temperature maintained in the foregoing separating step and at a pressure at which said normal butane is maintained in subtantially liquid phase, and withdrawing from the resulting calcium aluminosilicate a stream comprising normal pentane displaced from said silicate by normal butane in admixture with normal butane.
  • a process for separating normal hexane from a hydrocarbon mixture containing the same and at least one other hydrocarbon selected from the group consisting of branched chain hexanes and cyclic hydrocarbons which comprises contacting said mixture with a dehydrated crystalline calcium alurninosilicate containing pores having a cross-sectional diameter of about 5 augstrom units, capable of selectively sorbing said normal hexane while rejecting said other hydrocarbon, at a pressure at which said mixture is maintained in substantially liquid phase, withdrawing a hydrocarbon stream of decreased normal hexane content from the resulting calcium aluminosilicate containing sorbed normal hexane, thereafter contacting the silicate containing sorbed normal hexane with normal butane at substantially the tempera-,

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • Water Supply & Treatment (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
US568809A 1956-03-01 1956-03-01 Separation of normal paraffins from hydrocarbon mixtures using zeolitic molecular sieves Expired - Lifetime US2920037A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
NL108239D NL108239C (enrdf_load_html_response) 1956-03-01
US568809A US2920037A (en) 1956-03-01 1956-03-01 Separation of normal paraffins from hydrocarbon mixtures using zeolitic molecular sieves
CA723,889A CA1016873A (en) 1956-03-01 1957-02-21 Process for separating normal paraffins from hydrocarbon mixtures
GB6684/57A GB803184A (en) 1956-03-01 1957-02-28 Improvements in or relating to the separation of normal paraffins from hydrocarbon mixtures
DE19571795548 DE1795548B2 (de) 1956-03-01 1957-02-28 Verfahren zur erhoehung der oktanzahl einer normalparaffinhaltigen benzinkohlenwasserstofffraktion
DE1418428A DE1418428C2 (de) 1956-03-01 1957-02-28 Kontinuierliches Verfahren zur Abtrennung eines Normalparaffins mit mehr als vier Kohlenstoffatomen aus verzweigtkettige und cyclische Kohlenwasserstoffe enthaltenden Gemischen
ES0233939A ES233939A1 (es) 1956-03-01 1957-02-28 Un procedimiento para separar una parafina normal de una mezcla de hidrocarburos
FR1172788D FR1172788A (fr) 1956-03-01 1957-03-01 Procédé de séparation des paraffines normales des mélanges d'hydrocarbures

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US568809A US2920037A (en) 1956-03-01 1956-03-01 Separation of normal paraffins from hydrocarbon mixtures using zeolitic molecular sieves

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CA (1) CA1016873A (enrdf_load_html_response)
DE (2) DE1795548B2 (enrdf_load_html_response)
ES (1) ES233939A1 (enrdf_load_html_response)
FR (1) FR1172788A (enrdf_load_html_response)
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Cited By (17)

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US2978407A (en) * 1958-05-28 1961-04-04 Exxon Research Engineering Co Molecular sieve separation process
US3007980A (en) * 1958-06-20 1961-11-07 Sun Oil Co Removal of impurities from volatile liquids
US3053913A (en) * 1959-01-21 1962-09-11 Gulf Research Development Co Separation of high molecular weight hydrocarbons with molecular sieves
US3054838A (en) * 1958-09-08 1962-09-18 California Research Corp Method for separating n-hydrocarbons using molecular sieves
US3121757A (en) * 1960-10-28 1964-02-18 Universal Oil Prod Co Vibratory sorption separation process utilizing molecular sieves
US3141748A (en) * 1961-11-20 1964-07-21 Exxon Research Engineering Co Hydrogen purification process
US3183182A (en) * 1961-09-08 1965-05-11 British Petroleum Co Prolongation of sieve capacity by controlled desulfurization
US3184518A (en) * 1960-08-22 1965-05-18 Standard Oil Co Increased efficiency in molecular sieve adsorption system
US3226914A (en) * 1962-09-04 1966-01-04 Union Carbide Corp Pressure cycle for molecular sieve separation of normal paraffins from hydrocarbon mixtures
DE1275239B (de) * 1960-12-09 1968-08-14 Bayer Ag Verfahren zur Gewinnung reiner, geradkettiger Paraffine aus hochsiedenden Erdoelfraktionen
US3426086A (en) * 1965-01-04 1969-02-04 Phillips Petroleum Co Production and/or recovery of primary haloalkanes
US4394254A (en) * 1982-04-26 1983-07-19 Texaco Inc. Method for separating straight chain hydrocarbons using zeolites having large crystals
US5510564A (en) * 1994-12-12 1996-04-23 Uop N-paraffin purification process with removal of aromatics
US20060236595A1 (en) * 2005-04-22 2006-10-26 Norikazu Nakamura Biofuel conversion process
US20100116711A1 (en) * 2008-11-12 2010-05-13 Kellogg Brown & Root Llc Systems and Methods for Producing N-Paraffins From Low Value Feedstocks
EP2186784A2 (en) 2010-01-27 2010-05-19 Shell Internationale Research Maatschappij B.V. Process for the preparation and recovery of olefins
EP2186785A2 (en) 2010-01-27 2010-05-19 Shell Internationale Research Maatschappij B.V. Process for the separation of olefins from paraffins

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DE1194084B (de) * 1959-08-29 1965-06-03 Deutsche Erdoel Ag Verfahren zur Auftrennung von Kohlen-wasserstoffgemischen
BE598183A (enrdf_load_html_response) * 1959-12-15

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GB548905A (en) * 1941-02-24 1942-10-29 Richard Maling Barrer A process for the fractionation of hydrocarbon mixtures
DE871886C (de) * 1942-07-02 1953-03-26 Linde Eismasch Ag Adsorptionsverfahren
US2522426A (en) * 1945-05-30 1950-09-12 Standard Oil Dev Co Method of extrcting hydrocarbons
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US2306610A (en) * 1941-02-24 1942-12-29 Barrer Richard Maling Fractionation of mixtures of hydrocarbons
US2376425A (en) * 1941-06-02 1945-05-22 Phillips Petroleum Co Diolefin production
US2425535A (en) * 1945-07-25 1947-08-12 Standard Oil Dev Co Separation of normal paraffins from iso-paraffins by means of activated cocoanut charcoal
US2574434A (en) * 1949-06-04 1951-11-06 Socony Vacuum Oil Co Inc Method for refining petroleum hydrocarbons
US2586889A (en) * 1949-08-23 1952-02-26 Standard Oil Dev Co Separation of straight-chain from branched-chain hydrocarbons
US2859256A (en) * 1955-01-28 1958-11-04 Texas Co Separation process involving adsorption and desorption
US2818455A (en) * 1955-03-28 1957-12-31 Texas Co Desorption of straight chain hydrocarbons from selective adsorbents
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Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2978407A (en) * 1958-05-28 1961-04-04 Exxon Research Engineering Co Molecular sieve separation process
US3007980A (en) * 1958-06-20 1961-11-07 Sun Oil Co Removal of impurities from volatile liquids
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DE1418428C2 (de) 1974-04-04
GB803184A (en) 1958-10-22
ES233939A1 (es) 1957-08-01
DE1418428B1 (de) 1970-12-10
FR1172788A (fr) 1959-02-16
CA1016873A (en) 1977-09-06
DE1795548B2 (de) 1973-08-02
DE1795548A1 (de) 1972-04-13
NL108239C (enrdf_load_html_response)

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