EP0069943B1 - Procédé d'hydrogénation des hydrocarbures - Google Patents

Procédé d'hydrogénation des hydrocarbures Download PDF

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Publication number
EP0069943B1
EP0069943B1 EP82105941A EP82105941A EP0069943B1 EP 0069943 B1 EP0069943 B1 EP 0069943B1 EP 82105941 A EP82105941 A EP 82105941A EP 82105941 A EP82105941 A EP 82105941A EP 0069943 B1 EP0069943 B1 EP 0069943B1
Authority
EP
European Patent Office
Prior art keywords
hydrogenation
hydrocarbons
process according
anion exchangers
mixtures
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP82105941A
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German (de)
English (en)
Other versions
EP0069943A1 (fr
Inventor
Bernhard Dr. Schleppinghoff
Horst Dipl.-Ing. Reinhardt
Herbert Dipl. Ing. Tschorn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Erdoelchemie GmbH
Original Assignee
Erdoelchemie GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Erdoelchemie GmbH filed Critical Erdoelchemie GmbH
Priority to AT82105941T priority Critical patent/ATE13070T1/de
Publication of EP0069943A1 publication Critical patent/EP0069943A1/fr
Application granted granted Critical
Publication of EP0069943B1 publication Critical patent/EP0069943B1/fr
Expired legal-status Critical Current

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Classifications

    • 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
    • C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
    • C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only
    • C10G67/06—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only including a sorption process as the refining step in the absence of hydrogen
    • 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
    • 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
    • C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
    • 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
    • C10G2400/02—Gasoline

Definitions

  • the invention relates to a process for the hydrogenation of unsaturated hydrocarbons, in which these unsaturated hydrocarbons are treated with anion exchangers before a catalytic hydrogenation known per se.
  • LHSV space velocity
  • the anion exchangers which can be used according to the invention can be natural or synthetic, inorganic or organic anion exchangers.
  • natural or artificial inorganic anion exchangers are: natural or artificial scapolites or hydroxylapatites, iron oxide gels, carbon anion exchangers such as ammonium carbons, clay minerals, insoluble salts, such as phosphates, zirconium oxide hydrates, aluminum oxide and others.
  • organic anion exchangers examples include gel or macroporous styrene / divinylbenzene resins, condensation resins made from phenols and formaldehyde, cellulose anion exchangers with the functional group -OC z H 4 N (C 2 H 5 ) 2 or -OCH 2 C 6 H 4 NH 2 or another strongly basic functional group, called (meth) acrylic resins or epichlorohydrin / polyamine condensates.
  • cross-linked resins are cross-linked and thus made insoluble.
  • divinylbenzene crosslinker it is also possible, for example, to use trivinylbenzene or trivinylcyclohexane.
  • the crosslinker is generally present in an amount of about 0.3 to 80% by weight, preferably 1 to 65% by weight, particularly preferably 2 to 50% by weight, based on the total amount of the comonomers.
  • Anion exchangers with one of the matrices mentioned contain, for example, quaternary ammonium groups -NH 3 + , such as -N (CH 3 ) 3 + or -N (CH 3 ) 2 CH 2 CH 2 OH + , or tertiary amino groups -NR 2 , as functional groups -N (CH 3 ) 2 .
  • the matrices can also carry alkylene amine or imino groups or unsubstituted amino groups.
  • Anion exchangers of the types described have, for example, total capacities for ion exchange of about 0.5 to 6 val / P resin.
  • Anion exchangers in particular synthetic organic anion exchangers, are available in many variations and in a large number of types as commercial products from many manufacturers. Such anion exchangers can be used individually or as a mixture of several.
  • synthetic organic anion exchangers are preferably used.
  • Anion exchangers which have a matrix of styrene / divinylbenzene and have a gel-like or macroporous structure are used in a particularly preferred manner.
  • the anion exchangers mentioned can be loaded with various ions, for example with hydroxyl, chloride, bromide, sulfate, acetate or formate ions. Mixtures of different ion exchangers which are loaded with various of the anions mentioned by way of example can also be used. Mixtures of the same anion exchanger can also be used which the resin particles present in the mixture are loaded with various of the anions mentioned by way of example. Finally, it is also possible to use anion exchangers which, as a result of partial loading with salts of the various anions mentioned as examples, contain different anions in a resin particle.
  • Anion exchangers or mixtures of anion exchangers are preferably used in which hydroxyl ions are present as an anion, in whole or in part, on different resin particles or on the same resin particle, optionally in addition to one or more other anion (s).
  • hydroxyl ions are present as an anion, in whole or in part, on different resin particles or on the same resin particle, optionally in addition to one or more other anion (s).
  • a proportion of at least 10%, preferably at least 50%, particularly preferably 100% hydroxyl ions, based on the total number of anions may be mentioned.
  • Unsaturated hydrocarbons which are treated according to the invention include olefinic, diolefinic or acetylenic hydrocarbons, or hydrocarbons which contain one or more acetylenic bonds in addition to one or more olefinic bonds. Such unsaturated bonds can be either terminal or non-terminal. Such hydrocarbons can also be used as a pure substance fraction, as a mixture with one another or as a mixture with other substances. Such other substances can be, for example, saturated hydrocarbons, hydrogen, carbon monoxide, carbon dioxide, nitrogen or noble gases. Unsaturated or saturated hydrocarbons that can be treated according to the invention can be either branched or straight-chain. Their chain length is not critical for the implementation of the method according to the invention.
  • a chain length of 2 to 30, preferably 2 to 24, carbon atoms may be mentioned by way of example.
  • hydrocarbons and hydrocarbon mixtures mentioned are fractions such as those formed during the cracking of various cracking feedstocks or are produced from them, further fractions such as those obtained in the selective hydrogenation of cracking gasoline and cracking gasoline fractions, and furthermore fractions such as those used in the oligomerization of C 3 - and / or C 4 -olefins or olefin fractions with the aid of acidic catalysts.
  • the process according to the invention is preferably carried out by using such cracking fractions and oligomerization products with unsaturated bonds, which may also contain paraffins, naphthenes and / or aromatics as mixture components.
  • the inventive method is conducted at a temperature of for example 0 to 120 ° C, preferably 10 to 50 ° C, particularly preferably from 20 bar to 30 0 C and at a pressure of 1 to 100, preferably 1 to 15 bar, particularly preferably 1 to 5 executed in cash.
  • the hydrocarbons to be treated are at least partially in the liquid phase, for example at least 30%, preferably at least 80%, particularly preferably completely, based on the total amount of the hydrocarbons or the mixture proportions.
  • the hydrocarbons from. be driven upwards or downwards through a bed of the anion exchange particles.
  • the anion exchange particles can be arranged in a fixed bed, floating bed or in a fluidized bed.
  • the apparatus to be used to carry out the process according to the invention can be very simple, such as a cylindrical reactor without internals.
  • the anion exchanger can also be used in different beds, which are arranged, for example, on different bottoms of a cylindrical reactor. Further, between two such beds each distributor plates to secure Stel - Lung be located a uniform wetting of the different beds of anion exchanger.
  • the process according to the invention can be applied in the same way and with the same advantage to unsaturated hydrocarbons or the abovementioned mixtures which are then to be subjected to a selective hydrogenation or a full hydrogenation.
  • the bed of anion exchangers is filled with the unsaturated hydrocarbon to be treated or one of the mixtures mentioned with a space velocity LHSV (Liquid Hourly Space Velocity) of 0.1-10, preferably 0.5-5, particularly preferably 1-2 f hydrocarbons per f exchanger loaded per hour.
  • LHSV Liquid Hourly Space Velocity
  • the unsaturated hydrocarbons or the abovementioned mixtures are subjected to catalytic selective hydrogenation or full catalytic hydrogenation in a known manner.
  • the conditions for such a hydrogenation are known to the person skilled in the art.
  • 1 to 10 moles of hydrogen are used per mole of the double or triple bond to be hydrogenated.
  • it is carried out at 10 to 350 ° C and 1 to 200 bar.
  • hydrogenation catalysts are noble metal catalysts such as palladium or platinum, Raney catalysts such as Raney nickel, Raney cobalt, Raney iron or mixtures of such Raney catalysts, optionally with the addition of promoters, or sulfidic hydrogenation catalysts such as cobalt sulfides, nickel sulfides, molybdenum sulfides or Mixtures of these, called.
  • sulfidic hydrogenation catalysts such as cobalt sulfides, nickel sulfides, molybdenum sulfides or Mixtures of these, called.
  • inert carriers are SiO z , A1 2 0 3 , burnt MgO, carbonates such as CaC0 3 or BaC0 3 , sulfates such as BaS0 4 or activated carbon.
  • Such a catalytic hydrogenation can be carried out, for example, in the gas phase, the trickle phase or the liquid phase with a solid or suspended catalyst.
  • the method according to the invention is energetically and thus financially cheaper than previously known pretreatment methods. For example, the elimination of the energy-consuming and thus expensive distillation of the hydrogenation product should be mentioned.
  • the process according to the invention can be carried out in a simple and inexpensive apparatus and thus, in contrast to many previously conventional pretreatment processes, requires only a small investment.
  • the hydrogenation equipment consisted of: insert piston pump, preheater, hydrogenation reactor, cooler and separator.
  • VA reactors inner diameter 15 mm, length 700 mm with electric heating or with double jacket were used as hydrogenation reactors.
  • the lower half of the reactor (about 340 mm in length, corresponds to 60 m! Catalyst) was filled with a Pd catalyst on Al 2 O 3 .
  • the reactor room above was filled with Al 2 O 3 balls and served as an additional preheater.
  • the hydrogenation was carried out in the trickle phase with a hydrogen obtained in cracking plants with approx. 15% CH 4 at 26 bar and an LHSV (Liquid Hourly Space Velocity) of 5.
  • the bromine number (g Br z / 100 g) of the hydrogenated product was used as the criterion for the hydrogenation performance.
  • the product used was pyrolysis gasoline, which was to be selectively hydrogenated to a diene number of at most 1. This corresponds to a result of comparison measurements a reduction of the bromine number to 40-45 g Br2 / 100 g.
  • the inlet temperature was raised from 30-60 ° C. to 110-160 ° C., depending on the hydrogenation activity, the catalyst being considered deactivated if the temperature exceeded 100 ° C.
  • Untreated pyrolysis gasoline was used, as described above, for the selective hydrogenation of the diolefins.
  • the catalyst contained 5 g Pd / f on Al 2 O 3 , impregnated only on the surface. Fresh hydrogen was added to the reactor as exhaust gas was removed. The amount of exhaust gas was 200 l / h.
  • the hydrogenation was started at an inlet temperature of 60 ° C.
  • the bromine number rose after 5 days of operation to over 50 g Br ⁇ / 100 g, whereupon the inlet temperature had to be raised several times by 10-15 ° C. After a running time of 6 weeks, the inlet temperature of 110 ° C was exceeded. During the entire period were almost without exception only bromine numbers> 50 g Br 2 / g reaches 100th
  • Example 1 noble metal catalyst, 5 g Pd / run Al 2 O 3 , but soaked. As in Example 1, the inlet temperature had to be raised several times by 10-15 ° C after a week of running. After a running time of approx. 4 weeks, the inlet temperature of 110 ° C was exceeded.
  • the amount of exhaust gas had to be reduced to approx. 40 l / h and the inlet temperature to 30 ° C. After about 4 weeks, the inlet temperature was raised to 40 ° C. After 20 months of operation, the amount of exhaust gas was still 120 V / h instead of the “normal amount” of 200 l / h caused by the apparatus. After 20 weeks running, the inlet temperature was still 40 ° C, the bromine numbers varied between 38 to 45 g of Br 2/100 g, however, were generally at about 40 g Br z / 100 ml.
  • the hydrogenation equipment consisted of: insert piston pump, preheater, hydrogenation reactor, cooler and separator.
  • VA reactors 25 mm inside diameter, 700 mm length, with double jacket were used as hydrogenation reactors.
  • the reactors were filled with 400 ml of catalyst.
  • the free space above was filled with AI 2 0 3 balls. These served simultaneously as a liquid distributor and as an additional preheating zone.
  • the hydrogenation was carried out in the trickle phase with a trimer from a C 4 oligomerization (isododecene) as the starting product and with a hydrogen obtained in cracking plants with approx. 15% methane at 26 bar and an LHSV of 1.5.
  • the feed was preheated to 180 ° C and hydrogenated at a reactor temperature of 220 ° C.
  • the criterion for the hydrogenation performance the bromine number (g Br2 / 100 g) serving of the hydrogenated product.
  • a bromine number of 0.1 g Br2 / 100 g was regarded as the limit of the product specification, and exceeding this limit value was considered as deactivation of the catalyst.
  • untreated isododecene was used to fully hydrogenate the olefins in the hydrogenation apparatus.
  • the catalyst contained 18 g Pd / l on A1 2 0 3 , impregnated only on the surface. Fresh hydrogen was added to the reactor as exhaust gas was removed. The amount of exhaust gas was 200 i / h.
  • Example 5 the isododecene feed was treated with an anion exchanger before entering the hydrogenation.
  • This anion pre-cleaning was carried out in a fixed bed reactor at 20 ° C practically without pressure using an anion exchange mixture consisting of a part of weakly basic, macroporous ion exchanger based on polystyrene in the OH form (Bayer Lewatit MP 62) and a part of strongly basic, gel-like ion exchanger based on polystyrene in the CI 'form (Bayer Lewatit M 500).
  • the reactor consisted of a glass tube 350 mm long and 35 mm wide and was completely filled with the anion exchange mixture. Compared to Example 5, a considerable increase in the catalyst runtime has been achieved by treating the feed product with an anion exchanger.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Claims (7)

1. Procédé d'hydrogénation d'hydrocarbures, caractérisé en ce qu'on traite des hydrocarbures insaturés et des mélanges d'hydrocarbures constitués de fractions de craquage avec des échangeurs d'anions à une température de 0 à 120°C, sous une pression de 1 à 100 bars et à une vitesse spatiale (vitesse spatiale horaire de liquide) de 0,1 à 10 ℓd'hydrocarbures par litre d'échangeur, puis on les soumet à une hydrogénation catalytique de façon connue.
2. Procédé suivant la revendication 1, caractérisé en ce que, comme échangeurs d'anions, on utilise ceux comportant une matrice de styrène/divinyl- benzène avec une structure macroporeuse ou sous forme d'un gel.
3. Procédé suivant les revendications 1 et 2, caractérisé en ce qu'on travaille à une température de 10à 50° C.
4. Procédé suivant les revendications 1 et 2, caractérisé en ce qu'on travaille à une température de 20 à 30°C.
5. Procédé suivant les revendications 1 à 4, caractérisé en ce qu'on utilise des mélanges contenant des hydrocarbures insaturés provenant d'installations de craquage.
6. Procédé suivant les revendications 1 à 4, caractérisé en ce qu'on utilise des mélanges obtenus par hydrogénation partielle et contenant des hydrocarbures insaturés.
7. Procédé suivant les revendications 1 à 4, caractérisé en ce qu'on utilise des mélanges obtenus par oligomérisation catalytique d'oléfines en C3 et/ ou en C4 et contenant des hydrocarbures insaturés.
EP82105941A 1981-07-14 1982-07-03 Procédé d'hydrogénation des hydrocarbures Expired EP0069943B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT82105941T ATE13070T1 (de) 1981-07-14 1982-07-03 Verfahren zur hydrierung von kohlenwasserstoffen.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19813127751 DE3127751A1 (de) 1981-07-14 1981-07-14 Verfahren zur hydrierung von kohlenwasserstoffen
DE3127751 1981-07-14

Publications (2)

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EP0069943A1 EP0069943A1 (fr) 1983-01-19
EP0069943B1 true EP0069943B1 (fr) 1985-05-02

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EP82105941A Expired EP0069943B1 (fr) 1981-07-14 1982-07-03 Procédé d'hydrogénation des hydrocarbures

Country Status (6)

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US (1) US4431528A (fr)
EP (1) EP0069943B1 (fr)
JP (1) JPS5819388A (fr)
AT (1) ATE13070T1 (fr)
CA (1) CA1185272A (fr)
DE (2) DE3127751A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3338269A1 (de) * 1983-10-21 1985-05-02 Basf Ag, 6700 Ludwigshafen Verfahren zur gewinnung von isopren aus einem c(pfeil abwaerts)5(pfeil abwaerts)-kohlenwasserstoffgemisch
US6248230B1 (en) * 1998-06-25 2001-06-19 Sk Corporation Method for manufacturing cleaner fuels
SE9904197D0 (sv) * 1999-11-22 1999-11-22 Amersham Pharm Biotech Ab A method for anion exchange adsorption on matrices carrying mixed mode ligands
CN100444919C (zh) * 2004-10-22 2008-12-24 中国石化上海石油化工股份有限公司 一种分离利用甲基四氢苯酐生产废液的方法
CN100444918C (zh) * 2004-10-22 2008-12-24 中国石化上海石油化工股份有限公司 甲基四氢苯酐生产废液的分离方法
CN100448501C (zh) * 2004-11-11 2009-01-07 中国石化上海石油化工股份有限公司 甲基四氢苯酐生产过程中产生的废液的分离方法
US20070137097A1 (en) * 2005-12-16 2007-06-21 Michio Ikura Production of biodiesel from triglycerides via a thermal route

Family Cites Families (11)

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Publication number Priority date Publication date Assignee Title
US2566353A (en) * 1948-08-04 1951-09-04 Houdry Process Corp Purification of oils
US2780582A (en) * 1954-07-29 1957-02-05 Standard Oil Co Chemical refining and catalytic conversion of hydrocarbon oils
US3019199A (en) * 1957-08-29 1962-01-30 Shell Oil Co Regeneration of a nitrogen base containing ion exchanger
DE1183491B (de) * 1961-07-20 1964-12-17 Basf Ag Verfahren zum Reinigen von Olefinen
DE1275525B (de) * 1963-02-04 1968-08-22 Bayer Ag Verfahren zur vollstaendigen Hydrierung olefinischer Oligomerer aus Propylen und Butylenen
DE1568408A1 (de) * 1966-08-23 1970-03-05 Dow Chemical Co Verfahren zur Reinigung von Kohlenwasserstoffen
US3668271A (en) * 1967-10-02 1972-06-06 Mobil Oil Corp Hydrogenation of unsaturated hydrocarbons using ion exchange resin containing zero-valent metal as catalyst
AR206714A1 (es) * 1974-05-21 1976-08-13 Snam Progetti Procedimiento para eliminar compuestos acetilenicos de hidrocarburos saturados olefinicos y dienicos o mezcla de los mismos
US3953323A (en) * 1974-12-23 1976-04-27 Texaco Inc. Process for reduction of olefinic unsaturation of pyrolysis naphtha (dripolene)
IT1039740B (it) * 1975-07-08 1979-12-10 Snam Progetti Procedimento per l addizione di acidi organici a composti acetile nici contenuti in correnet i idrocar buriche inorganiche do organiche
FR2410038A1 (fr) * 1977-11-29 1979-06-22 Inst Francais Du Petrole Procede d'hydrogenation selective d'essences contenant a la fois des composes generateurs de gommes et des composes indesirables du soufre

Also Published As

Publication number Publication date
US4431528A (en) 1984-02-14
JPS5819388A (ja) 1983-02-04
EP0069943A1 (fr) 1983-01-19
ATE13070T1 (de) 1985-05-15
DE3127751A1 (de) 1983-02-03
CA1185272A (fr) 1985-04-09
DE3263386D1 (en) 1985-06-05

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