US3345285A - Ethylene, butadiene production - Google Patents

Ethylene, butadiene production Download PDF

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Publication number
US3345285A
US3345285A US394581A US39458164A US3345285A US 3345285 A US3345285 A US 3345285A US 394581 A US394581 A US 394581A US 39458164 A US39458164 A US 39458164A US 3345285 A US3345285 A US 3345285A
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stream
butene
zone
ethylene
disproportionation
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US394581A
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John F Hutto
Rolland E Dixon
Joseph W Davison
Charles A Ayres
Graham A Renberg
Donald K Macqueen
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Phillips Petroleum Co
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Phillips Petroleum Co
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Priority to US394581A priority patent/US3345285A/en
Priority to FR30175A priority patent/FR1456769A/fr
Priority to BE669163D priority patent/BE669163A/xx
Priority to DE1468831A priority patent/DE1468831C3/de
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/12—Alkadienes
    • C07C11/16—Alkadienes with four carbon atoms
    • C07C11/167—1, 3-Butadiene

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  • This invention relates to hydrocarbon conversion.
  • the invention relates to a method and apparatus for combined naphtha cracking, olefin disproportionation and olefin dehydrogenation.
  • the invention relates -to the combined processing of the effluent of a cracking furnace and the effluent of an olefin dehydrogenation.
  • the invention relates to removing a heavy fraction prior to subsequent removal of lighter fractions lfrom a hydrocarbon stream.
  • the invention relates to use of a single deethanizing step and deethanizer to treat the feed to and the effluent from a propylene disproportionation.
  • the invention relates to removal of C4 paraffins from a side stream to prevent build-up in a butene dehydrogenation feed stream.
  • the invention relates to combining butylenes from a butadiene recovery section and from a disproportionation step to produce a feed to a dehydrogenation unit.
  • the invention relates to the separation of the effluent from a disproportionation reactor and recycle of appropriate products.
  • disproportionation is used to mean the conversion of a hydrocarbon into similar hydrocarbons of higher and lower numbers of carbon atoms per molecule. Such an operation is useful in many instances. For example, a more plentiful hydrocarbon can be converted to a less plentiful and, therefore, more valuable hydrocarbon.
  • the reactant comprises 1- or 2-olefins
  • a mixture of new products is obtained comprising primarily olefins having both a larger and a smaller number of carbon atoms than the feed olefin but also including some other disproportionated products, for example, saturated hydrocarbons and other converted and unconverted material.
  • Disproportionation can be accomplished using a catalyst comprising molybdenum oxide and aluminum oxide and preferably also an oxide of cobalt, or other disproportionation catalyst, to produce a disproportionated product comprising a very small quantity of saturated hydrocarbons and a relatively small amount of branched chain olefins.
  • Butadiene conventionally is produced by the dehydrogenation of butane in one or two steps.
  • the production by such a process entails a very difficult separation problem since a stream containing butane, l-butene, 2-butene and butadiene is produced.
  • Propylene often is available in excess quantities as a result of the cracking operations. Although some of the propylene can be used, for example, for alkylation, some for polymerization to polypropylene resins or for propylene tetramer for use in the manufacture of detergents, often there still remains a quantity of propylene for which it is difficult to find a use.
  • other olefins ethylene on the one hand and butene on the other hand, for example, are in demand, the ethylene for the ICC production of ethylene polymers for example and butene for the production of butadiene as indicated above. By disproportionating propylene, both ethylene and butene can be produced.
  • ethylene can be provided at such locations by the conversion of propylene by disproportionation.
  • the propylene and the C4s fed to the dehydrogenation unit both result from the cracking of naphtha in one aspect of our invention.
  • An object of our invention is to produce ethylene and butadiene -from naphtha. Another object of our invention is to reduce the separation facilities required in a combined naphtha cracking and butene dehydrogenation operation.
  • Another object of our invention is to convert propylene to more valuable higher and lower olefins.
  • Another object of our invention is to facilitate plural fractionation steps by early removal of a heavier fraction.
  • Another object of our invention is to make efficient use of separation facilities both on the feed and the effluent of a disproportionation reaction.
  • Another object of our invention is to prevent the buildup of C4 paraffins in a butene dehydrogenation feed stream.
  • Another object of our invention is to provide a feed stock for dehydrogenation.
  • Another object of our invention is to provide efficient separation of disproportionation products.
  • a hydrocarbon stream is cracked, the effluent separated to produce a feed stream suitable for feed to a dehydrogenation step and the efliuent from the dehydrogenation step is fed to the same separation apparatus.
  • a stream suitable for use as a feed to an olefin disproportionation unit and efiiuent from the disproportionation unit also is returned to the separation apparatus at the proper point.
  • fractionation of a multi-component hydrocarbon stream is facilitated by removing a heavy fraction prior to subsequent removal of lighter fractions.
  • eicient use is made of separation facilities by separating components of the eiiiuent of a disproportionation reaction in the same facilities utilized for separating components from the feed to the disproportionation reaction.
  • prevention of buildup of butane in a butadiene manufacturing system is prevented by removal of butane from a side stream of the main feed stream.
  • a first dehydrogenation feed stream is produced by naphtha cracking followed by separation of products not desired in the hydrogenation
  • a second dehydrogenation feed stream is produced by propylene disproportionation followed by separation of products not desired in the dehydrogenation and combining the first and second feed streams prior to feeding into the dehydrogenation zone.
  • build-up of propane in a disproportionation system wherein propylene and propane are recycled to the ⁇ disproportionation reaction zone by passing the disproportionated stream into a first separation Zone, removing the first separation stream which comprises substantially all of the ethylene in the disproportionated stre-am, -a second stream comprising substantially all of the butene with a minor amount of propylene and an amount of propane substantially equal to the net amount of propane entered in the process, and a third stream comprising the major proportion of the propylene and propane, transferring the second stream into a second separation zone, removing a fourth stream comprising substantially all of the butene and a fifth stream comprising substantially all of the propane in the amount in the second separated stream and recycling the third stream tot the disproportionation zone.
  • the build-up of propane in a propylene disproportionation system is avoided by passing the disproportionated stream into a separation zone, removing a stream comprising ethylene, and a stream comprising butene, and recycling a stream comprising propylene and propane, and withdrawing from the system a relatively small amount of the recycled stream.
  • dehydrogenation in a broad sense, relates to any suitable reaction producing dehydrogenated products corresponding with ⁇ the feed stream.
  • a reaction yspecifically directed toward dehydrogenation of butene to produce butadiene is included as well as a butene cracking step which also lproduces butadiene as well as other products.
  • butene produced from naphtha cracking is further cracked to produce butadiene
  • 2-butene produced from the same naphtha cracking also is cracked to produce additional butadiene
  • Z-butene resulting from the disproportionation of propylene produced in the naphtha cracking is combined in the Z-butene cracking zone.
  • Oiur invention relates to process aspects and to apparatus aspects.
  • a catalyst comprising molybdenum oxide and aluminum oxide and preferably also an oxide of cobalt, tungsten oxide o-n alumina, molybdenum oxide or tungsten oxide on silica, or on silica-alumina, tungsten carbonyl or molybdenum carbonyl on silica, alumina or silica-alumina, or other variations of these catalysts, tungsten sulfide or molybdenum sulfide on alumina or other disproportionation catalysts to produce a disproportionated product comprising a very small quantity of saturated hydrocarbons and a relatively small amount of branched chain olefins.
  • the reactant comprises 1- or 2-olefins
  • a mixture of new products comprising primarily olefins, some having a larger and some a smaller number of carbon atoms than the feed, and also including some other disproportionated products.
  • Conditions can be controlled to obtain a veryhigh efficiency of conversion to desired disproportionation products. For example, propylene can consistently be converted to ethylene and butenes with an elicency above 95 percent.
  • Any catalyst suitable yfor disproportionating olefins can be used in the practice of our invention.
  • One catalyst used in our invention comprises.y an oxide of aluminum promoted by an oxide of molybdenum and, preferably, additionally promoted by an oxide of cobalt.
  • Suitable supports include 100 percent alumina, silicaalumina wherein the amount of silica is up to about 25 Ipercent of the total support, magnesia-alumina wherein the amount of magensia is up to about 20 percent of the total support, and titania-alumina wherein 5 the amount of titania is up to about S5 percent of the total support.
  • the amount of molybdenum oxide or tungsten oxide is in the range of 0.5 to 30 percent by weight of the total catalyst composition, preferably 1 to 15 percent.
  • Cobalt oxide can be present in the molybdenum promoted catalyst in the range of to 20 percent by weight of the total catalyst, preferably l to percent. Excellent results with high conversion have been obtained with molybdenum oxide in the range of 4 to 13 percent by weight of the total catalyst.
  • the composite catalyst can -be prepared by any conventional method such as dry mixing, coprecipitation or impregnation.
  • a -100 mesh alumina having a 178 m.2/g. surface area and la 107 A. pore diameter
  • a molybdenum compound such as ammonium molybdate
  • a commercially available catalyst comprising 12.8:3.8:83.4 MoO3-CoO-Al203 having a 208 rn.2/g. surface area and and a 96 A. pore diameter is also satisfactory, the ratios being by weight.
  • a suitable heat activation treatment can be performed where necessary or desirable to give an olefin disproportionation active catalyst.
  • the process of our invention can be carried out either batchwise or continuously, using a fixed catalyst bed, or a stripper equipped reactor or other mobile catalyst contacting process as well as ⁇ any other well known contacting technique.
  • Preferred reaction conditions eg., temperature, pressure, flow rates, etc., vary somewhat depending upon the specific catalyst composition, the particular feed olefin, desired products, etc.
  • the temperature, pressure, and contact times are selected for the particular catalyst to give the desired disproportionation conversion with ,the feedstock used.
  • the disproportionation reaction can be carried out either in the presence or absence of a diluent.
  • Diluents selected from the group consisting of paraflinic and cycloparainic hydrocarbons can be employed. Suitable diluents are, for example, propane, cyclohexane, methylcyclohexane, normal pentane, nor-mal hexane, isooctane, dodecane, and the like, or mixtures thereof, including primarily those parains and cycloparans having up to l2 carbon atoms per molecule.
  • FIGURE 1 illustrates a unitized system for naphtha cracking, propylene disproportionation, and butene dehydrogenation, for the production of ethylene and butadiene, along with by-products.
  • FIGURE 2 illustrates another embodiment of the disproportionation and separation system.
  • FIGURE 3 illustrates a combination of naphtha cracking, propylene disproportionation and butene cracking, producing ethylene and butadiene and by-products.
  • FIGURE 4 illustrates a unitized system for naphtha cracking, propylene disproportionation, and butene dehydrogenation, utilizing a simplified separation system.
  • a naphtha stream is passed into naphtha cracker 11 through conduit 12 and the effluent passed to heat recovery and quench 13 through conduit 14.
  • the effluent from the naphtha cracking furnace is quenched in waste heat boilers, and a two-stage quench tower provides for subequent cooling by passing the vapors upwardly through the tower, the lower section of ⁇ which is an oil quench and the upper section a multiple water quench.
  • steam is generated in waste heat boilers in the cracking furnace stack gas system.
  • a fuel oil condenses in the quench tower and is removed as a side stream Afrom the circulating quench oil.
  • the elfluent from the quench tower is compressed and fed to debutanizer as one vapor stream and two condensate streams. This is accomplished by passing the effluent from heat recovery and quench section 13 through compressor 16 into ash chamber V17, the condensate beingpassed to debutanizer 15 through conduit 19 while the overhead is compressed in compressor 21 and passed to flash chamber22 from which the condensate is passed to debutanizer ⁇ 15 through conduit 23 and the vapor is transferred to debutanizer 15 through conduit 24.
  • a debutanized gasoline stream is removed as a bottoms product from debutanizer 15 through conduit 26.
  • the overhead is further compressed in compressor 27 and passed through an amine treating unit for the removal of CO2 and HZS.
  • the effluent from amine treater 28 is passed to caustic wash and dry unit 29 Where the eiiluent from the amine unit is caustic washed to remove the last traces of acid gases, then water washed to prevent caustic carry over.
  • the eluent from caustic wash and dry unit 29 is fed to depropanizer 30.
  • the butane and heavier bottoms product from depropanizer 30 is passed through conduit 31 to the butadiene recovery and purication unit, the iirst stage being a furfural absorber 32.
  • Butadiene is absorbed in absorber 32 and the -rich furfural passed into furfural stripper 33, furural being returned to furfural absorber 32 through conduit 34, and the butadiene rich stream passed through conduit 35 into butadiene column 36.
  • a high purity butadiene stream is taken overhead through conduit 37, and the bottoms product, comprising butenes, is passed through conduit 38 into conduit 39 which feeds butene deoiler 40.
  • the overhead from the furfural absorber is separated into two streams, one stream being passed through conduit 41 into a cold acid isobutylene removal unit 42 while the outher stream is passed through conduit 41 and conduit 43 into butene extraction column 44 which controls the build-up of butanes in the system by removal of butanes from this side stream.
  • the debutanized stream from extraction column 44 is passed through conduit 45 and recombined with the stream being fed to isobutylene removal unit 42.
  • the deoiled overhead from butene deoiler' 40 is passed into butene dehydrogenation reactor 46 and the el'luent passed through conduit 47 to the separation system for the eiiuent from naphtha cracker 12.
  • the euent from the dehydrogenation reactor is quenched in a waste heat boiler and cooled in a stack oil 'and water quench tower similar to the naphtha cracking furnace effluent heat recovery and quench system.
  • the propane and lighter fraction from depropanizer 30 is compressed in compressor 51 and passed into the primary lacetylene removal reactor 52.
  • 'Ihis unit is operated under high selectivity, lou/,conversion conditions to remove the bulk'of C2 and C3 acetylenes, piperidene, and butadiene, without significant losses of ethylene or propylene.
  • this stream again is dried to remove water formed from oxygen compounds in the acetylene removal reactor feed and then fed to cooling train 53.
  • Cooling train 53 is a series of refrigerated and recycled cooled heat exchangers and a centrifugal expander, with corresponding required auxiliary surge tanks, pumps, etc.
  • a hydrogen rich vapor and a methane rich vapor are removed as by-products, and the remainder of the stream is liqueed and sent to demethanizer 54.
  • the demethanzer overhead is recycled through the cooling train for sensible heat recovery and then is produced fas a -fuel gas-byproduct.
  • the demethanizer bottoms primarily ethane, ethylene, propane and propylene, are fed through conduit 56 into deethanizer 57.
  • the deethanizer overhead is fed through conduit 58 into secondary acetylene removal reactor 59, operated at high conversion and low selectivity, to bring the acetylene content to a low value.
  • the etlluent from the secondary acetylene removal reactor is fed to ethylene fractionator 61 'and separated into an overhead ethylene stream and a bottoms product ethane stream.
  • the ethane stream is removed through conduit 62 while the ethylene stream is passed through conduit 63 to methane stripper 64, with high purity ethylene being removed through conduit 66.
  • methane stripper 64 contains sufficient ethylene to justify reseparation, and this stream is recycled to the suction of compressor 51 through conduit 67 as shown.
  • the bottoms product from deethanizer 57 is passed through conduit 71 to an acetylene removal unit 72.
  • This unit is operated at high conversion, low selectivity, to reduce the methylacetylene Iand propadiene concentration suiliciently to prevent damage to the disproportionation catalyst.
  • the eruent from acetaylene removal unit 72 is fed to disproportionation reactor 73.
  • the effluent from reactor 73 is passed through conduit 74 to propylene splitter 76.
  • the overhead, comprising ethylene and lighter, is recycled to deethanizer 57 through conduit 77.
  • a side draw, primarily propylene and propane, is recycled through conduit 78 to the inlet of reactor 73.
  • the bottoms product, propane and heavier, is fed to depropanizer 81 through conduit 82 and the bottoms product from depropanizer 81 is fed through conduit 83 into the inlet for butene deoiler 40.
  • the effluent from the disproportionation reactor 101 is passed through conduit 102 into a fractional distillation column 103.
  • the overhead from column 103 comprising substantially al1 of the ethylene which is fed to column 103 through conduit 102, and smaller quantities of propylene and propane, is returned through conduit 104 to deethanizer 106.
  • the overhead from deethanizer 106 is passed to ethylene fractionator 107 through conduit 108.
  • the side draw of column 103 which is removed through conduit 109, comprises a very large portion of the propane and propylene fed through conduit 102, along with a minor amount of ethylene.
  • the major portion of this stream is recycled to disproportionation reactor 101 through conduit 111, combined with the bottoms y'product from deethanizer 106 which is passed through conduit 112 while a minor amount of the side draw is bled through conduit 113 to prevent buildup of propane.
  • the bottoms product from column 103 comprising substantially all of the butenes which are fed through conduit 102, along with t-race amounts of other materials, is passed through conduit 114 to a butene dehydrogenation unit.
  • the butene dehydrogenation referred to can be either a speciic dehydrogenation unit as described above in connection with FIGURE 1 or can be a butene cracking unit as described below with respect to FIG- URE 3.
  • butadiene dehydrogenation step is preferred.
  • very substantial quantities of butadiene, comprising a large part of the potentially available butadiene can lbe produced with a very much smaller investment in operating costs, by using butene cracking steps as illustrated in FIGURE 3.
  • the naphtha cracking effluent from reactor 116 is passed through conduit 117 to separation unit 118.
  • separation unit 118 a heavier stream, such as a depropanized gasoline stream and fuel oil, is rremoved as illustrated schematically by conduit 119.
  • a C4 hydrocarbon stream is passed through conduit 121 into butadiene recovery unit 7 122, similar to the butadiene recovery unit illustrated and described with respect to FIGURE 1 above.
  • l-butene is removed separately from Z-butene, the 1-butene being passed to isobutylene removal unit 124 ⁇ and to 1-butene cracking unit 123, and the 2-butene being passed through conduit 126 to 2-butene cracking unit 127.
  • the C3 hydrocarbon stream is passed to disproportionation unit 128 and the euent, after separation in unit 129, comprising primarily 2-butene, is passed through conduit 131 into Z-butene cracking unit 127.
  • the effluent from cracking unit 123 and cracking unit 127 are passed into separation unit 118.
  • Example l In an example of the operation lof our invention according to FIGURE 1, the stream fed to cracking reactor 11 comprises a wide range naphtha made from a Kuwait crude, the naphtha having a boiling range of 105 to 352 F., density of 64.3 API and comprising 72 volume percent parain (44 percent N-parain), 18 percent by volume naphtha and percent by volume aromatics, with substantially no olens.
  • the operating conditions of the various units of the system are given in Table I, and a material balance is presented in Table II, the numbers of the streams corresponding with numbers in FIGURE 1.
  • Example II In an example according to FIGURE 2, all of the conditions are the same as the conditions of FIGURE 1 for all the units not shown in FIGURE 2, including naphtha cracking, butene dehydrogenation, etc. In the portion illustrated in FIGURE 2, the conditions in the various units are given in Table III and the material balance ofthe various streams in Table IV.
  • Example III In an example according to FIGURE 3, the conditions in the various units are given in Table V and the material balance in Table VI.
  • the feed stream is the naphtha of Example I.
  • Conditions not given in Table V and material balance values not listed in Table VI are the same as corresponding values in the system of Example I.
  • Reflux drum 100 p.s.i.a., 62 F.
  • Reboiler vapor 110 p.s.i.a., 313 F. 27
  • 3rd Compressor stage
  • Absorber tower 250 ⁇ p.s.i.a.; 160 F. in, 135 F.
  • Reflux drum 100 p.s.i.a., 138 F.
  • Reboiler vapor 120 p.s.i.a., 303 F.
  • Furfural stripper
  • Reflux drum 65 p.s.i.a., 1 ⁇ 10 F.
  • Reboiler Vapor p.s.i.a., 329 F.
  • Butadiene column
  • Girdler G-73 catalyst 520 p.s.i.a., 350 F. Cooling train:
  • Inlet 485 p.s.i.a., 55 F.
  • Hydrogen separator 455 p.s.i.a., 200 F. Demethanizer:
  • Reboiler vapor 435 p.s.i.a., 52 F. Deethanizer:
  • Reboiler vapor 4410 p.s.i.a., 147 F.
  • Secondary acetylene removal unit 4410 p.s.i.a., 147 F.
  • Girdler G-58 catalyst i12/C2H2 ratio 2.0.
  • Reboiler vapors 300 p.s.i.a., 3 F. Methane stripper:
  • Reflux drum 420 p.s.i.a., 114 F.
  • Reboiler vapor 430 p.s.i.a., 239 F.
  • Propane stripper 430 p.s.i.a., 239 F.
  • Reflux drum 265 p.s.i.a., 123 F.
  • Reboiler vapor 275 p.s.i.a., 246 F.
  • Reactor conditions 460 p.s.i.a., 850 F.
  • Steam/HC ratio 1.0.
  • Product SPhtter Outlet pressure 25 p.s.i.a.
  • FIGURE 4 the operation is somewhat similar to the operation of the system illustrated in FIGURE l, but a much simpler separation system is utilized.
  • a naphtha stream is passed into naphtha cracker 131 through conduit 132 and the efuent passed to heat recovery and quench 133 through conduit 134.
  • the heat recovery and quench section 133 can be 4similar to the corresponding section 13 of FIGURE 1.
  • the eiuent from the quench tower is compressed in compressor 136 and compressor 137 and passed into ash chamber 138, the condensate from flash chamber 138 being passed to ash chamber 139.
  • the overhead from ash chamber 138 is passed through caustic Wash and dr-y unit 141 and compressor 142 into ash chamber 143.
  • the overhead from flash chamber 143 is passed through a heat exchange train 144 into a flash chamber 146.
  • the condensate from chamber 146 is passed into demethanizer 147.
  • the bottoms product from demethanizer 147 is passed into acetylene removal unit 148 and then to ethylene fractionator 149 from which an ethylene product stream is removed overhead and ethane removed from the bottom.
  • the condensate from flash chamber 143 is passed through a C3 acetylene removal unit 151 into product splitter 152.
  • the overhead from flash chamber 139 also passes through acetylene removal unit 151 into product splitter 152.
  • the overhead from product splitter 152 is passed into the stream comprising the bottoms product from demethanizer 147 and passed through acetylene removal unit 148 into ethylene fractionator 149.
  • a side draw is taken from product splitter 152 and passed to propylene disproportionation unit 153 with the product from unit 153 being returned to product splitter 152.
  • the bottoms product from product splitter 152 is passed into furfural absorber 155.
  • the rich furfnral, comprising butadiene, is passed into furfural stripper 1577 and the butadiene containing stream stripped from the furfural is passed into butadiene column 158.
  • Butadiene is removed overhead from column 158 with the bottoms product being recycled to furfural absorber 156.
  • the rafnate from absorber 6 is passed into isobutylene removal unit 158, with isobutylene being removed therefrom and the remaining stream passed to butene deoiler 159.
  • a slip stream, from conduit 161 which transports the ranate from absorber 156 to isobutylene removal unit 158, is taken through butane extractor 162.
  • Butanes are removed as a rafnate from extractor 162 while the butenes are recovered and returned to conduit 1611.
  • the overhead from butene deoiler 159 is passed into butene dehydrogenation unit 166 and a product stream is returned to compressor 136.
  • a process for olefin disproportionation comprising the steps of:
  • a process for olen disproportionation comprising the steps of passing a feed comprising propylene an-d propane into a disproportionation zone; in said disproportionation zone converting propylene to ethylene and butene; removing from said disproportionation zone a disproportionated stream comprising ethylene, propylene,
  • a process for the production of ethylene and butadiene from hydrocarbon which comprises the steps of:
  • a process for producing ethylene and butadiene comprising the steps of:

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US394581A 1964-09-04 1964-09-04 Ethylene, butadiene production Expired - Lifetime US3345285A (en)

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Application Number Priority Date Filing Date Title
GB1050558D GB1050558A (xx) 1964-09-04
US394581A US3345285A (en) 1964-09-04 1964-09-04 Ethylene, butadiene production
FR30175A FR1456769A (fr) 1964-09-04 1965-09-02 Procédé perfectionné de conversion des hydrocarbures par craquage
BE669163D BE669163A (xx) 1964-09-04 1965-09-03
DE1468831A DE1468831C3 (de) 1964-09-04 1965-09-03 Verfahren zur Herstellung von Äthylen und Butadien aus Erdolkohlenwasser stoffen

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Cited By (7)

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Publication number Priority date Publication date Assignee Title
US3485890A (en) * 1967-04-03 1969-12-23 Phillips Petroleum Co Conversion of propylene into ethylene
US4067921A (en) * 1976-12-06 1978-01-10 The Dow Chemical Company Primary adjunct, continuous diene process
US4458096A (en) * 1983-05-26 1984-07-03 Air Products And Chemicals, Inc. Process for the production of ethylene and propylene
US4676885A (en) * 1986-05-28 1987-06-30 Shell Oil Company Selective process for the upgrading of distillate transportation fuel
JP2014001171A (ja) * 2012-06-19 2014-01-09 Tosoh Corp １，３−ブタジエンの製造方法
US20160184732A1 (en) * 2012-10-30 2016-06-30 Lummus Technology Inc. Butadiene extraction process
WO2019042449A1 (zh) * 2017-09-04 2019-03-07 中国石油化工股份有限公司 乙烯的制造方法

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US2416023A (en) * 1944-09-18 1947-02-18 Phillips Petroleum Co Catalytic conversion of hydrocarbon oil
US2777801A (en) * 1951-12-03 1957-01-15 Exxon Research Engineering Co Combination crude distillation and oil refining process
US3113164A (en) * 1955-06-20 1963-12-03 Phillips Petroleum Co Dehydrogenation process and recovery of the resulting dehydrogenated products
US3172834A (en) * 1965-03-09 Process for manufacturing gasoline by blending the hydrocracked gasoline with the dehydrogenated and alkyl- ated products obtained from the hy- drocracking stage
US3261879A (en) * 1963-09-27 1966-07-19 Phillips Petroleum Co Olefin disproportionation

Patent Citations (5)

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Publication number Priority date Publication date Assignee Title
US3172834A (en) * 1965-03-09 Process for manufacturing gasoline by blending the hydrocracked gasoline with the dehydrogenated and alkyl- ated products obtained from the hy- drocracking stage
US2416023A (en) * 1944-09-18 1947-02-18 Phillips Petroleum Co Catalytic conversion of hydrocarbon oil
US2777801A (en) * 1951-12-03 1957-01-15 Exxon Research Engineering Co Combination crude distillation and oil refining process
US3113164A (en) * 1955-06-20 1963-12-03 Phillips Petroleum Co Dehydrogenation process and recovery of the resulting dehydrogenated products
US3261879A (en) * 1963-09-27 1966-07-19 Phillips Petroleum Co Olefin disproportionation

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3485890A (en) * 1967-04-03 1969-12-23 Phillips Petroleum Co Conversion of propylene into ethylene
US4067921A (en) * 1976-12-06 1978-01-10 The Dow Chemical Company Primary adjunct, continuous diene process
US4458096A (en) * 1983-05-26 1984-07-03 Air Products And Chemicals, Inc. Process for the production of ethylene and propylene
US4676885A (en) * 1986-05-28 1987-06-30 Shell Oil Company Selective process for the upgrading of distillate transportation fuel
JP2014001171A (ja) * 2012-06-19 2014-01-09 Tosoh Corp １，３−ブタジエンの製造方法
US20160184732A1 (en) * 2012-10-30 2016-06-30 Lummus Technology Inc. Butadiene extraction process
US9744475B2 (en) * 2012-10-30 2017-08-29 Lummus Technology Inc. Butadiene extraction process
WO2019042449A1 (zh) * 2017-09-04 2019-03-07 中国石油化工股份有限公司 乙烯的制造方法
US11091412B2 (en) 2017-09-04 2021-08-17 China Petroleum & Chemical Corporation Process for producing ethylene

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DE1468831A1 (de) 1969-02-20
BE669163A (xx) 1966-03-03
FR1456769A (fr) 1966-07-08
GB1050558A (xx)
DE1468831C3 (de) 1973-10-11
DE1468831B2 (de) 1973-03-15

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