US3180904A - Process for the manufacture of olefins - Google Patents

Process for the manufacture of olefins Download PDF

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Publication number
US3180904A
US3180904A US30400A US3040060A US3180904A US 3180904 A US3180904 A US 3180904A US 30400 A US30400 A US 30400A US 3040060 A US3040060 A US 3040060A US 3180904 A US3180904 A US 3180904A
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Prior art keywords
cracking
hydrocarbons
heat
steam
cracking zone
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Expired - Lifetime
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US30400A
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English (en)
Inventor
Fischer Kurt
Hirschbeck Josef
Rummert Gunter
Rothe Adolf
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Hoechst AG
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Hoechst AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/02—Alkenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/005—Processes comprising at least two steps in series
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/11—Purification; Separation; Use of additives by absorption, i.e. purification or separation of gaseous hydrocarbons with the aid of liquids
    • 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
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/20—C2-C4 olefins
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P30/00—Technologies relating to oil refining and petrochemical industry
    • Y02P30/40—Ethylene production
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S585/00—Chemistry of hydrocarbon compounds
    • Y10S585/909—Heat considerations
    • Y10S585/91—Exploiting or conserving heat of quenching, reaction, or regeneration

Definitions

  • the present invention relates to a process for the manufacture of olefins of high purity containing 2 to 4 carbon atoms.
  • the present invention is concerned with a novel process for the manufacture of olcfins of high purity and containing 2 to 4 carbon atoms by pyrrolizing higher hydrocarbons and subsequently decomposing the reaction mixture.
  • the process of the invention avoids the disadvantages of the known methods. lt is carried out as follows: iirst a carrier gas mixture consisting essentially of steam is produced, said mixture is then admixed in a cracking zone with the hydrocarbons to be cracked, the reaction mixture leaving the cracking zone is cooled to a temperature in the range from 60() to 159 C.
  • the high boiling hydrocarbons that are not suitable for being reconducted into the cracking zone are separated by further cooling, the readily liqueiiable hydrocarbons, which are to be reconducted into the cracking zone, are separated by subsequent direct cooling, the cracked gases are freed in known manner from carbon dioxide, sulfur compounds and acetylene hydrocarbons, then compressed at Ztl-30 atmospheres gauge in order to separate low boiling hydrocarbons that are still present and are liquid at room temperature, which hydrocarbons are likewise reconducted into the cracking zone, the oleiins and carbon monoxide in the cracked gas thus treated are separated by means of solutions containing cuprous salts from hydrogen, methane and homologs thereof, which may be present, an olen concentrate is obtained from the copper salt solution, and the individual olens are isolatedy ldrogen and oxygen in a steam atmosphere.
  • a characteristic feature of the present invention consists in that the main quantity of the heat set free in the individual cooling phases of the cracked products is used for superheating and generating the steam required in the pyrolysis, while the residual amounts of heat and the main portion of the condensation heat is utilized for covering the heat requirement in the individual stages of the gas purification and decomposition.
  • hydrocarbon mixtures to be treated for example crude oil or crude oil fractions, are introduced either in liquid or vaporous form into the cracking zone where they are mixed with the simultaneously arriving carrier gas.
  • the amounts of heat required for heating the hydrocarbon mixture to be cracked and for maintaining the cracking reaction are produced by the combustion of hy-
  • lt is likewise possible, of course, to use as combustion gas in the cracking unit a hydrogen-hydrocarbon mixture of another origin, provided that it does not contain essential amounts of carbon monoxide which would lead to an increased content of carbon dioxide in the cracked gas and to-undesired and disturbing side reactions in the cracking process.
  • the working with relatively high amounts of steam as carrier and diluent presents the further advantage that the' apparatus must not be made of highly alloyed, nickel-free chromium steels the processing of Which is very difficult as it is known.
  • Materials having a low chromium content, which may also contain nickel, can be used provided that'they are stable at a temperature of about 1100 C.
  • the crackingzone is preferably formed by a tube-shaped reaction space made of such a material whichA is suitably built into a combustion chamber of ceramic construction material and insulated against the said chamber by a ceramic shield.
  • the process of the invention gives high yields of olens of high purity containing 2 to 4 carbon atoms and, moreover, it is very economical since the heat required for decomposing the cracked products is taken to a great extent from the Waste heat obtained in the cracking process, The heat leaving the cracking zone is completely utilized except for a small amount of condensation heat.
  • the process of the invention can be largely varied with respect to the starting materials and the oleiins to be obtained as iin-al products.
  • the olens cannot only be produced from Well defined hydrocarbons and hydrocarbon mixtures but also from crude and waste oils of most different origin.
  • the process is especially suitable for treating 'paraflinic oils, but it can likewise be used for other hydrocarbon mixtures containing, in addition to paratiins, also naphthenes and aromatic compounds. Oils containing a fairly small portion of aromatic hydrocarbons are preferred since the latter favor the formation of undesired residues unless they are removed by an additional device.
  • Starting materials which do not contain unvaporizable residues are advantageously vaporized in a vaporizer preceding the cracking unit and being disposed within the heat conduction of the process, and introduced into the cracking zone in the form of vapor. In many cases it is also possible to introduce liquid starting materials directly into the cracking zone. Crude oils, residue oils and waste oils often contain considerable amounts of portions which are not suitable for the production of the desired olens and ⁇ form high boiling residues. It is, therefore, of advantage not to introduce such oils directly into the cracking zone but to inject them into the hot reaction mixture in the direct cooling zone (quenching) following the heat exchange after the cracking zone.
  • the amounts of heat taken up by the quenching cycles are used in waste heat boilers for the generation of steam, which, after having been superheated in indirect heat exchangers immediately following the cracking zone, is reconducted as heat carrier to the cracking zone.
  • the reaction mixture is cooled to 50G-400 C. while the heat carrier steam is simultaneously heated to 60G-700 C.
  • Said heat exchange is preferably carried out in single or double cyclones, as described for example in German Patent 1,000551 or Belgian Patents 552,522 and 561,754, by superheating the steam which enters at a temperature of about 100 C. to 60G-700 C. while reaching high heat transfer coefficients.
  • said' heat exchangers or part of them can also be used for generating the heat carrier steam required in the cracking zone from water or preferably steam condensate.
  • the heat balance of the process of the invention is furthermore improved by the suitable intercalation of known devices for the gas purification and separation, which are arranged so that they utilize, on the one hand, the waste heat still available from the cracking unit and, on the other hand, the desired olelins are obtained in a high degree of purity, independent of the composition and amount of the cracked gases.
  • the combination in accordance with the invention of the gas purification and gas separation is, furthermore, fairly independent of possible variations in the cracking zone, ⁇ for example by the use of other starting materials or by milder or stronger cracking conditions.
  • the gas is purified and separated in several stages.
  • the cracked gases are rst freed in known manner from carbon dioxide, sulfur compounds and acetylene.
  • the .portions that are liquid at normal temperature and pressure are separated from the gas mixture by compression at 10-30 atmospheres gauge, for example 25 atmospheres gauge.
  • the oleins are separated in concentrated form from the residual gas mainly consisting of hydrogen and methane and no longer suitable of being converted into olens by washing the gas with a solvent having a selective action for olelins, and the latter are decomposed.
  • cuprous salt solutions As selective washing liquids for the separation of the olefins from the cracked gas cuprous salt solutions are preferably used, other washing liquids having a selective action such as solutions of silver nitrate or of a silverboron fluoride complex compound being likewise suitable.
  • the separation by means of cuprous salts is preferably carried out as described in Belgian Patents 564,888, 565,181 and 569,799.
  • the residual gas that is free from carbon monoxide and essentially consists of hydrogen, methane and small amounts of ethane and propane may serve as mentioned above as combustion gas for the cracking unit where it can be used instead of or in addition to hydrogen.
  • the concentrate of olefins obtained in the washing operation with the copper salt solution is decomposed by distillation in known manner. If the olefin mixture leaving the copper salt washing step still contains carbon monoxide formed in the cracking operation the latter is suitably removed by the process described in Belgian Patent 557,538. Alternatively the carbon monoxide can be separated from the oleins in the course of the olefin decomposition by distillation, usually by low temperature distillation. Since in the process of the invention the low boiling constituents of the cracked gas such as hydrogen and methane, the concentration of which in these cracked gases may largely vary, are already removed, the distillative final operation is carried out with mixtures that can be readily separated into the individual constituents. The working up in the process of the invention is also superior from an economical point of view to a total decomposition of the cracked gas by means of a multistage low temperature distillation.
  • the process of the invention permits, without additional expenditure pertaining to apparatus, to produce either ethylene alone or ethylene-l-propylene or ethylene-j-propylene-i-butylene.
  • For carrying out one or the other working method of the operational conditions must only be varied slightly.
  • butylene and propylene can be wholly or partially separated with the liquid products and reconducted into the cracking zone where they can be con- Verted into ethylene within the extremely short time of about 0.01 second due to the high dilution of the cracked gases by means of steam which is characteristic of the process of the invention.
  • the invention with its characteristic heat conduction permits to apply in the individual stages of gas purification and gas decomposition processes which entirely utilize with high economy the heat obtained in the crack- "e, redone.
  • Carbon dioxide and hydrogen sulfide can be washed out with hydroxy-alkyl amines or aminofatty acids by the Girbutol or Alkacid process by taking the heat required for the desorption and regeneration from the waste heat of the cracking operation available in the final condensers.
  • FIGURE 1 illustrates the processing of a crude oil
  • FlGURE 2 represents a liowing scheme for the processing of vaporizable hydrocarbons. As far as the latter arrangement is in conformity with the arrangement of FIGURE 1 the same numerals have been chosen.
  • the heat carrier steam mixture thus generated in reactor 3 is admixed in the cranking zone of reactor 3 designed as reaction tube with the hydrocarbon vapors produced in vaporizer 30 from the crude oil to be cracked, which vapors are introduced into the cracking zone by way of conduit 5. ln the cracking zone of reactor 3 the hydrocarbon vapors are cracked to yield a mixture of ethylene, propylene, butylenes, hydrogen, methane and smaller amounts of higher boiling hydrocarbons. Said mixture leaves reactor 3 via conduit o and travels into the indirect heat exchanger 7 (preferably designed as described in Belgian Patent 561,754) where it is cooled to about 60G-450 C., while steam entering the reactor as heat carrier by Way of conduit 4 is simultaneously heated to about 600 C.
  • the indirect heat exchanger 7 preferably designed as described in Belgian Patent 561,754
  • the mixture of the reaction products is passed via conduit 3 into the first quenching device 9 designed as washer in which it is cooled to about 350 C. in a downward cocurrent with the fresh crude oil introduced by way of conduit 1u.
  • the residues which can no longer be used in the Y cracking operation are discharged through conduit 11 and conducted to a boiler unit 31 where they serve to generate steam from the feed water introduced by way of conduit 53.
  • the mixture of the reaction products is transported via conduit 12 into the second quenching device 13 where it is cooled to a temperature that is adapted to the boiling range of the crude oil to be processed.
  • the mixture is suitably contacted in a countercurrent with a return oil obtained in the' process or with another thermostable oil.
  • the heat taken up by the oil in quenching devices 9 and 13 serves in waste heat boilers ld and 17 to vaporize water, preferably steam condensate ootained in other parts of the unit (30, 3d).
  • the steam thus generated is conducted via conduit 21 together with the steam generated in boiler unit 3l into heat exchanger 7 where it is superheated and then passed through conduit 4 into the reactor.
  • conduit 22 By way of conduit 22 the mixture of the reaction products is conducted to a direct and/ or indirect cooling system 23 in which it is cooled to normal temperature while dissipating its heat to a water circuit 24-25 whereby the cold water supplied through conduit 25 is heated to about -100" C.
  • the heated Water is transported by way of conduit 2d' to parts 41 and 43 described below, where it serves as heating agent, and then reconducted as cold water through conduit 25 into the cooling system.
  • conduit 2d They travel via conduit 2d into a separator 27 where the lighter oil layer separates from the water layer.
  • the water is discharged through conduit 28 while the oily hydrocarbons are'conducted by way of conduit 29 into vaporizer 3d which is heated via conduit 21 by means of a partial steam current from boiler unit 31 and from which the vaporous hydrocarbons are passed through conduit 5 into the reactor 3.
  • the reaction mixture is conducted through conduit 32 to the mist dispersion installation 33.
  • the mist is preferably removed by the process described in Belgian Patent 562,894 according to which the mist dispersion is combined with a compression of the reaction mixture at about 1 atmosphere gauge.
  • the gas mixture which is now tree from mist is conducted through ⁇ conduit 34 to the gas' purification zone 35 for the removal of CO2.l and H28.
  • the washing liquor to be regenerated is heated in unit 35 by indirect heat exchange.
  • the condensate obtained is passed through conduit 3S to the waste heat boilers 14 and 17, together with the condensate obtained in the hydrocarbon vaporizer 3u which travels through conduit 20, and is then conducted as heat carrier steam again to superheater 7 and reactor 3.
  • the cracked gas freed from CO2 and sulfur compounds is introduced into the purilication unit 39 where it is freed from acetylene hydrocarbons, preferablyV by selective catalytic hydrogenation (cf. German Patent 612,205
  • the undesired oleins are separated in separator 41 together with the higher boiling hydrocarbons and conducted via conduit 42 to the hydrocarbon vaporizer 30 and from there through conduit 5, together with the other vaporized hydrocarbons, into reactor 3.
  • the portions of the reaction mixture that are to be discharged and the portions that are to be reconducted can likewise be separated'from one another by fractionation or by an oil wash.
  • both working methods can be combined by iirst carrying out a rough fractionation and by removing the other component to be separated in a subsequent oil wash.
  • a further modification consists in that the indirect heat exchangers 7 and 117 installed between reactor 3 and quenching device 13 not only serve to superheat the heat carrier steam supplied but also to generate steam.
  • the working method according to FIGURE 2 which corresponds to that illustrated in FIGURE 1, unless otherwise stated, permits an elastic temperature control and heat conduction which can be further improved by treating in one unit a partial current of the hydrocarbon mixture according to FIGURE 1 and another partial current according to FIGURE 2.
  • different starting materials can be processed while the reaction products are worked up and the gases are puriiied and separated in a common unit which is connected in the same manner with both reactor units and utilizes the waste heat thereof.
  • a process for the manufacture of olciins of high purity containing 2 to 4 carbon atoms by pyrolyzing hydrocarbons and subsequently decomposing the reaction mixture which comprises superheating by means described below a carrier gas mixture consisting essentially of steam, admixing said carrier gas mixture in a cracking Zone with the hydrocarbons to be cracked, cooling the reaction mixture leaving the cracking zone to a temperature in the range from 600 to C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Water Supply & Treatment (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US30400A 1959-05-15 1960-05-16 Process for the manufacture of olefins Expired - Lifetime US3180904A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF28445A DE1203756B (de) 1959-05-15 1959-05-15 Verfahren zur kontinuierlichen Erzeugung von Olefinen

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DE (1) DE1203756B (enrdf_load_stackoverflow)
GB (1) GB947923A (enrdf_load_stackoverflow)
NL (1) NL251595A (enrdf_load_stackoverflow)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3433850A (en) * 1963-06-26 1969-03-18 Petro Tex Chem Corp Preparation of unsaturated hydrocarbons
US3475510A (en) * 1966-04-13 1969-10-28 Lummus Co Ethylene and synthesis gas process
US3862898A (en) * 1973-07-30 1975-01-28 Pullman Inc Process for the production of olefinically unsaturated hydrocarbons
US3923921A (en) * 1971-03-01 1975-12-02 Exxon Research Engineering Co Naphtha steam-cracking quench process
US4107226A (en) * 1977-10-19 1978-08-15 Pullman Incorporated Method for quenching cracked gases
EP0825245A3 (en) * 1996-08-16 1998-05-20 Stone & Webster Engineering Corporation Chemical absorption process for recovering olefins from cracked gases
ES2529841R1 (es) * 2012-02-17 2015-03-27 Uop Llc Procesos y aparatos de procesado de hidrocarburos para la preparación de mono-olefinas
CN113336619A (zh) * 2021-05-13 2021-09-03 华陆工程科技有限责任公司 一种利用羰基合成气制备乙炔气体的方法
CN114216111A (zh) * 2021-11-09 2022-03-22 北方华锦化学工业股份有限公司 全废锅流程裂解气冷却工艺

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8586811B2 (en) * 2012-02-17 2013-11-19 Uop Llc Processes and hydrocarbon processing apparatuses for preparing mono-olefins

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2429134A (en) * 1945-09-11 1947-10-14 Jasco Inc Extraction of diolefins
US2672489A (en) * 1948-07-10 1954-03-16 Gyro Process Co Pyrolysis of gaseous hydrocarbons for the production of unsaturated compounds
US2855433A (en) * 1955-05-13 1958-10-07 Phillips Petroleum Co Recovery of olefin hydrocarbons
US2878262A (en) * 1956-10-18 1959-03-17 Pure Oil Co Hydrocarbon pyrolysis process
US2889384A (en) * 1954-11-11 1959-06-02 Ici Ltd Production of olefinic gases from hydrocarbon oils
US2912475A (en) * 1955-04-28 1959-11-10 Hoechst Ag Manufacture of low molecular unsaturated hydrocarbons
US2942042A (en) * 1957-10-15 1960-06-21 Phillips Petroleum Co Ethylene purification
US2945076A (en) * 1957-04-15 1960-07-12 Gulf Research Development Co Process for producing olefins
US2953521A (en) * 1957-03-18 1960-09-20 Socony Mobil Oil Co Inc Liquid-liquid heat exchange in mixed phase hydrocarbon conversions

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1050328B (de) * 1959-02-12 Chemische Werke Hüls Aktiengesellschaft, Marl (Kr. Recklinghausen) Verfahren zum Regenerieren von Dehydrierkatalysatoren

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2429134A (en) * 1945-09-11 1947-10-14 Jasco Inc Extraction of diolefins
US2672489A (en) * 1948-07-10 1954-03-16 Gyro Process Co Pyrolysis of gaseous hydrocarbons for the production of unsaturated compounds
US2889384A (en) * 1954-11-11 1959-06-02 Ici Ltd Production of olefinic gases from hydrocarbon oils
US2912475A (en) * 1955-04-28 1959-11-10 Hoechst Ag Manufacture of low molecular unsaturated hydrocarbons
US2855433A (en) * 1955-05-13 1958-10-07 Phillips Petroleum Co Recovery of olefin hydrocarbons
US2878262A (en) * 1956-10-18 1959-03-17 Pure Oil Co Hydrocarbon pyrolysis process
US2953521A (en) * 1957-03-18 1960-09-20 Socony Mobil Oil Co Inc Liquid-liquid heat exchange in mixed phase hydrocarbon conversions
US2945076A (en) * 1957-04-15 1960-07-12 Gulf Research Development Co Process for producing olefins
US2942042A (en) * 1957-10-15 1960-06-21 Phillips Petroleum Co Ethylene purification

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3433850A (en) * 1963-06-26 1969-03-18 Petro Tex Chem Corp Preparation of unsaturated hydrocarbons
US3475510A (en) * 1966-04-13 1969-10-28 Lummus Co Ethylene and synthesis gas process
US3923921A (en) * 1971-03-01 1975-12-02 Exxon Research Engineering Co Naphtha steam-cracking quench process
US3862898A (en) * 1973-07-30 1975-01-28 Pullman Inc Process for the production of olefinically unsaturated hydrocarbons
US4107226A (en) * 1977-10-19 1978-08-15 Pullman Incorporated Method for quenching cracked gases
DE2845376A1 (de) * 1977-10-19 1979-04-26 Pullman Inc Verfahren zum abschrecken von crack-gasen
EP0825245A3 (en) * 1996-08-16 1998-05-20 Stone & Webster Engineering Corporation Chemical absorption process for recovering olefins from cracked gases
ES2529841R1 (es) * 2012-02-17 2015-03-27 Uop Llc Procesos y aparatos de procesado de hidrocarburos para la preparación de mono-olefinas
CN113336619A (zh) * 2021-05-13 2021-09-03 华陆工程科技有限责任公司 一种利用羰基合成气制备乙炔气体的方法
CN114216111A (zh) * 2021-11-09 2022-03-22 北方华锦化学工业股份有限公司 全废锅流程裂解气冷却工艺

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GB947923A (en) 1964-01-29
NL251595A (enrdf_load_stackoverflow) 1900-01-01
DE1203756B (de) 1965-10-28

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