US3662015A - Method of preventing double bond migration of mono-olefinic hydrocarbons in selective hydrogenation - Google Patents

Method of preventing double bond migration of mono-olefinic hydrocarbons in selective hydrogenation Download PDF

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Publication number
US3662015A
US3662015A US828186A US3662015DA US3662015A US 3662015 A US3662015 A US 3662015A US 828186 A US828186 A US 828186A US 3662015D A US3662015D A US 3662015DA US 3662015 A US3662015 A US 3662015A
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mono
hydrogenation
hydrocarbon
selective hydrogenation
double bond
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US828186A
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Youji Komatsu
Yasuhiro Furukawa
Takashi Yokomizo
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Cosmo Oil Co Ltd
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Maruzen Oil Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/08—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
    • C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
    • C07C2523/44—Palladium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
    • C07C2523/74—Iron group metals
    • C07C2523/755—Nickel

Definitions

  • the present invention relates to a method of preventing the double bond migration of mono-olefinic hydrocarbons during the selective hydrogenation of poly-unsaturated hydrocarbons of poly-olefinic and/ or acetylenic types coexisting with said mono-olefinic hydrocarbons, each of the mono-olefinic hydrocarbons and the poly-unsaturated hydrocarbons having at least four carbon atoms.
  • a poly-unsaturated hydrocarbon of the poly-olefinic and/or acetylenic type having at least four carbon atoms, coexisting with a mono-olefinc hydrocarbon having at least four carbon atoms may be hydrogenated in the presence of hydrogen using a hydrogenation catalyst such as palladium-, platiniumor nickel, to selectively convert said poly-unsaturated hydrocarbons into the corresponding mono-olefinic hydrocarbons.
  • a hydrogenation catalyst such as palladium-, platiniumor nickel
  • butene containing C -diolefins and/or C -acetylenes may be selectively hydrogenated in the presence of hydrogen using a palladium, platinum or nickel catalyst to convert said C -dio1efins and/or C acetylenes into the corresponding butenes, without loss of butenes, thereby obtaining butenes substantially free from said C -diolefins and C -acetylenes.
  • the conventional hydrogenation catalysts such as palladium, platinum and nickel, used for such selective hydrogenation processes possess the disadvantage of promoting double bond migration in addition to the desired hydrogenation of the unsaturated bonds, Accordingly, conventionally practiced selective hydrogenations employing such catalysts are inevitably accompanied by double bond migration of mono-olefinic hydrocarbons.
  • butenes e.g. l-butene, Z-butene, isobutene
  • C -diolefins e.g. 1,3-butadiene, methyl allene
  • C -acetylenes e.g. dimethyl acetylene, ethyl acetylene, vinyl acetylene
  • the basic object of the present invention is to provide a method of preventing the double bond migration of mono-olefinic hydrocarbons during the selective hydrogenation of poly-unsaturated hydrocarbons coexisting with mono-olefinic hydrocarbons, each of mono-olefinic hydrocarbons and poly-unsaturated hydrocarbons having at least four carbon atoms, in the presence of hydrogen using a palladium or nickel-hydrogenation catalyst.
  • Another object of the present invention is to provide a process for the selective hydrogenation of poly-unsaturated hydrocarbons containing mono-olefinic hydrocarbons, each of said poly-unsaturated hydrocarbons and mono-olefinic hydrocarbons having at least four carbon atoms, in the absence of the usual accompanying double bond migration.
  • Still another object of the present invention is to provide a method of inhibiting only the isomerization (double bond migration) activity of conventional hydrogenation catalysts being employed for the selective hydrogenation of poly-unsaturated hydrocarbons coexisting with monoolefinic hydrocarbons, each of said poly-unsaturated hydrocarbons and mono-olefinic hydrocarbons having at least four carbon atoms.
  • FIGS. 1, 2, 3 and 4 indicate the changes in the composition of the hydrogenation products with reference to 1,3-butadiene and l-butene, obtained by the selective hydrogenation of butenes containing 1,3-butadiene using a palladium hydrogenation catalyst at a temperature of C., a pressure of 25 kg./cm. and a hydrogen atmosphere containing 0, 10, 25 and 50 mol. percent of carbon monoxide respectively, based on the hydrogen present. All tests in FIGS. 1-4 are carried out under the same reaction conditions, e.g., feed stocks, hydrogenation catalyst employed, reaction temperature and total pressure etc., except that the content of carbon monoxide in the hydrogen is varied respectively.
  • the right axis of ordinate indicates the content of 1,3-butadiene (p.p.m.)
  • the left axis of ordinate indicates the content of l-butene (mol. percent)
  • the axis of abscissa indicates the reaction period (in hours).
  • the solid line of each figure indicates the change in l-butene content and the dotted line indicates the change in 1,3-butadiene content.
  • the poly unsaturated hydrocarbons coexisting with the monoolefinic hydrocarbons, each of which hydrocarbons having at least four carbon atoms, are selectively hydrogenated in the presence of hydrogen and 150 mol. percent of carbon monoxide, based on the hydrogen, using a palladium or nickel catalyst.
  • said polyunsaturated hydrocarbons are selectively hydrogenated and thus eliminated, and the double bond migration of said mono-olefinic hydrocarbons is effectively prevented.
  • hydrocarbon feed utilized in the selective hydrogenation of the present invention comprises a mixture of mono-olefinic hydrocarbon and a poly-unsaturated hydrocarbon, each having at least four carbon atoms.
  • the hydrocarbon feed may contain hydrocarbons having up to 16 carbon atoms.
  • the said polyunsaturated hydrocarbons are poly-olefinic hydrocarbons (e.g. di-olefins, tri-olefin's and the like) and/ or acetylenic hydrocarbon (e.g. alkynes, alkenynes).
  • the content of the poly-unsaturated hydrocarbons in the hydrocarbon feed are preferably less than about 50 mol. percent.
  • Feeds containing greater amounts of poly-unsaturated hydrocarbons may, however, be employed within the scope of the invention.
  • the hydrocarbon feed may contain parafiinic hydrocarbons, such as n-butane, pentane, hexane, etc., and inert gases, such as hydrogen, nitrogen, etc.
  • Hydrogen to be used in this invention may be either pure hydrogen or hydrogen-containing gases, such as natural gas, Platformer elf-gas, etc.
  • the rest of hydrogen being required for the selective hydrogenation of this invention may be supplied from an external source.
  • the amount of hydrogen employed in the present invention will vary depending upon the contents of the poly-unsaturated hydrocarbon in the hydrocarbon feed. It is necessary to use more than the stoichiometric amount of hydrogen needed for hydrogenating the polyunsaturated hydrocarbons into corresponding mono-olefinic hydrocarbons. In general, 1-20,000 moles of hydrogen per total mole of poly-unsaturated hydrocarbons may be employed for the selective hydrogenation.
  • the hydrogenation catalyst to be used in the present invention is a hydrogenation catalyst containing palladiurn or nickel.
  • Suitable hydrogenation catalysts are palladium or nickel metals, or the sulfides or oxides of these metals, or such metals or compounds supported on known carriers, such as alumina, silica-alumina, magnesia, titania, diatomaceous earth etc. by conventional treatment.
  • the selective hydrogenation of poly-unsaturated hydrocarbons coexisting with mono-olefinic hydrocarbons, wherein each of the poly-unsaturated and mono-olefinic hydrocarbons has at least four carbon atoms is easily carried out, without causing double bond migration in the mono-olefinic hydrocarbons, in the presence of hydrogen as aforesaid and 1-50 moi percent preferably 5-3O mole percent, of carbon monoxide, based on the hydrogen present, using a palladiumor nickel catalyst.
  • the use of carbon monoxide in an amount of less than 1 mol percent based on the hydrogen present is not desirable, since double bond migration will take place along with the selective hydrogenation. If the amount of carbon monoxide is more than 50 mole percent, other disadvantages become apparent, e.g. prolongation of the reaction period for the selective hydrogenation, of the polyunsaturated hydrocarbon take place, although the double bond migration is still prevented.
  • the carbon monoxide may be introduced to the reaction system in any manner as long as hydrogen is also present. In practical operation, it is convenient to previously mix the carbon monoxide with hydrogen in a specific ratio and then to bring the resultant carbon monoxide-hydrogen mixture into contact with the hydrocarbon feed.
  • the selective hydrogenation of the present invention is preferably carried out at a tempearture of 20-250 C. under the pressure of about atmospheric to 50 kg./crn. Under such a relatively mild reaction condition, skeletal isomerization of the mono-olefinic hydrocarbons will not take place in any substantial amount during the selective hydrogenation.
  • the hydrocarbon feed is introduced as either an upflow or downfiow to a reactor packed with the hydrogenation catalyst at an L.H.S.V. of 0.1-40 and is selectively hydrogenated therein. Although it is convenient to contact the hydrocarbon feed with the hydrogenation catalyst in a fixed bed, if necessary or desired, a moving or fluidized bed may be employed.
  • the selective hydrogenation may be carried out either in batch, semicontinuous or continuous operation. It is also possible to introduce a sulfur compound, such as hydrogen sulfide, mercaptan or carbon disulfide together with carbon monoxide to the reaction system for the purpose, of avoiding excessive hydrogenation in the process of this invention.
  • the present invention is particularly useful in carrying out the selective hydrogenation of butenes containing C diolefins and/or C -acetylenes without lowering the 1- butene content, and also in obtaining l-butene, or a fraction rich in l-butene, from l-butene mixtures with C -diolefins and/or C acetylenes by selective hydrogenation.
  • the field of the application of the present invention is not limited only to those specific examples.
  • EXAMPLE 1 The hydrocarbon feed employed was a butene-containing feed having the composition shown in Table 1. Said butene feed is a raflinate extracted from a C -fraction produced by naphtha steam cracking.
  • the hydrogenation catalyst employed was a commercial palladium catalyst (PGCC produced by Engelhard Industries, Ltd.) containing 0.1% by weight of palladium supported on alumina.
  • a vertically disposed reactor of 50 mm inner diameter was packed with 200 ml. of the palladium catalyst.
  • the butene feed mixed with p.p.m. of hydrogen sulfide at the rate of 600 mL/hr. (L.H.S.V 3.0) and hydrogen containing 25 mol. percent carbon monoxide at the rate of 60 liters (N. T.P.)/hr. at a temperature of 100 0., under a pressure of 25 kg./cm. to effect the selective hydrogenation.
  • a hydrogenation product thus obtained was analyzed by gas chromatography.
  • EXAMPLE 1a The selective hydrogenation was carried out using the same feed, catalyst and reaction conditions as those used in Example 1 except that hydrogen free from carbon monoxide was utilized.
  • the compositions of the butene feed and the hydrogenation product are given in Table 2.
  • TAB LE 2 Feed Product composition composition (mol percent) (mol percent) Propane and propylene 2. 6 2. 6 Isobutane 3. 6 6. 1 9 6 13.3 43.0 43. 1 25. 9 4. 0 14. 1 31. 4 1. 2 0.05
  • Example 2 The procedure of Example 1 was carried out except that a nickel-containing hydrogenation catalyst containing 10% by weight of nickel supported on alumina was used in place of the palladium-alumina catalyst.
  • the said nickel catalyst was prepared by the following procedure: A solution was prepared by dissolving nickel nitrate 170 g. in water 170 g.: An alumina pellet (5 x 5 mm.) 300 g. was then impregnated with the nickel nitrate solution. The impregnated alumina pellet was dried to evaporate Water. The pellet was calcined in the air at 400 C. for 5 hours and then at 650 C. for 4 hours. The calcined catalyst was reduced with hydrogen at 400 C. for 4 hours.
  • Table 3 The compositions of the butene feed and the hydrogenation product are given in Table 3.
  • Example 3 The procedure of Example 1 was carried out except that the hydrocarbon feed employed was a 0.; fraction having the composition shown in Table 4, which was produced by naphtha steam cracking, and that the rate of hydrogen containing 25 mol. percent carbon monoxide was 600 liters (N.T.P.)/hr.
  • Example 4 The procedure of Example 1 was carried out except that the hydrocarbon feed employed was a C -fraction, and that the rate of hydrogen containing 13 mol percent carbon monoxide was liters (N.T.P.)/hr.
  • the composition of the feed and product are given in Table 5.
  • Example 5 The procedure of Example 1 was carried out except that the hydrocarbon feed employed was an octene feed containing methyl heptatriene, and that the rate of hydro gen containing 13 mol percent carbon monoxide was 300 liters (N.T.P.)/hr.
  • composition of the feed and product are given in Table 6.
  • 3-methyl heptatriene is selectively hydrogenated into 3-methyl heptadiene and then successively into 3-methyl heptene, but the product content of l-octene shows little change from that of the feed.
  • higher polyolefin than C tri-olefins can be selectively hydrogenated as well with effective prevention of the double bond migration.
  • said catalyst consisting of a carrier and a member selected from the group consisting of palladium and nickel in the presence of from 1 to 50 mol percent of carbon monoxide, based upon the amount of hydrogen present.
  • hydrocarbon mixture is a mixture of compounds having from 4 to 16 carbon atoms in the molecule.
  • nickel catalyst is present in an amount of from 1.0 to 40.0 percent by weight, and the carrier is present in an amount of at least 60.0 percent by weight.
  • the carrier is a member selected from the group consisting of alumina, silica-alumina, magnesia, titania, and diatomaceous earth.
  • said sulfur compound is a member selected from the group consisting of hydrogen sulfide, mercaptan and carbon disulfide.

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US828186A 1968-05-27 1969-05-27 Method of preventing double bond migration of mono-olefinic hydrocarbons in selective hydrogenation Expired - Lifetime US3662015A (en)

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4251674A (en) * 1979-10-22 1981-02-17 Phillips Petroleum Company Method and apparatus for improving the selectivity of a process for hydrogenating acetylene to ethylene
US4520214A (en) * 1984-04-04 1985-05-28 Uop Inc. High selectivity process for dehydrogenation of paraffinic hydrocarbons
US4523045A (en) * 1984-04-04 1985-06-11 Uop Inc. Process for converting paraffins to olefins
US4523048A (en) * 1984-04-04 1985-06-11 Uop Inc. Process for the selective production of alkylbenzenes
US4705906A (en) * 1985-11-27 1987-11-10 The British Petroleum Company, P.L.C. Selective hydrogenation of acetylene
US4761509A (en) * 1987-02-24 1988-08-02 Uop Inc. High selectivity process for dehydrogenation of paraffinic hydrocarbons
US5177282A (en) * 1989-05-05 1993-01-05 Huels Aktiengesellschaft Oligomerization of olefins
US5281753A (en) * 1992-04-21 1994-01-25 Engelhard Corporation Process for the selective hydrogenation and isomerization of hydrocarbons
WO2000064846A1 (en) * 1999-04-27 2000-11-02 Phillips Petroleum Company Hydrocarbon hydrogenation catalyst and process
US6417135B1 (en) 1999-08-27 2002-07-09 Huntsman Petrochemical Corporation Advances in dehydrogenation catalysis
US6469223B2 (en) 2000-01-04 2002-10-22 Fina Technology, Inc. Selective hydrogenation of dienes
US20030229285A1 (en) * 2002-06-11 2003-12-11 Simpson David Hope Ultrasonic diagnostic micro-vascular imaging
US6747181B1 (en) * 1998-04-28 2004-06-08 Dsm N.V. Process for the hydrogenation of phenyl acetylene in a styrene-containing medium with the aid of a catalyst

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3751499A (en) * 1972-05-05 1973-08-07 Goodyear Tire & Rubber Hydrogenation process
FR2474024A1 (fr) * 1980-01-23 1981-07-24 Inst Francais Du Petrole Procede de production de butene-1 a partir d'une coupe c4 d'hydrocarbures
DE3143647A1 (de) * 1981-11-04 1983-05-11 Chemische Werke Hüls AG, 4370 Marl Verfahren zur selektiven hydrierung von mehrfach ungesaettigten kohlenwasserstoffen in kohlenwasserstoff-gemischen
US6734130B2 (en) 2001-09-07 2004-05-11 Chvron Phillips Chemical Company Lp Hydrocarbon hydrogenation catalyst composition, a process of treating such catalyst composition, and a process of using such catalyst composition
EA012189B1 (ru) * 2007-10-15 2009-08-28 Алий Байдильдаевич АУЕЗОВ Способ гидрирования полиальфаолефинов

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1244730A (fr) * 1959-01-09 1960-10-28 Bayer Ag Procédé d'hydrogénation sélective de composés non saturés en fractions c4
US3325556A (en) * 1964-05-18 1967-06-13 Universal Oil Prod Co Selective hydrogenation of acetylene in a mixture of acetylene and other unsaturated hydrocarbons
FR1498268A (fr) * 1965-09-23 1967-10-20 Inst Francais Du Petrole Procédé perfectionné d'hydrogénation sélective des dioléfines
FR1497098A (fr) * 1965-10-29 1967-10-06 Huels Chemische Werke Ag Procédé pour l'hydrogénation sélective de butadiène-(1, 3) dans un mélange d'hydrocarbures contenant d'assez grandes quantités de butène-(1), ainsi que d'assez faibles quantités de butadiène-(1, 3)
FR1513123A (fr) * 1967-03-06 1968-02-09 Catalysts & Chem Inc Hydrogénation sélective, plus particulièrement de l'acétylène

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4251674A (en) * 1979-10-22 1981-02-17 Phillips Petroleum Company Method and apparatus for improving the selectivity of a process for hydrogenating acetylene to ethylene
US4520214A (en) * 1984-04-04 1985-05-28 Uop Inc. High selectivity process for dehydrogenation of paraffinic hydrocarbons
US4523045A (en) * 1984-04-04 1985-06-11 Uop Inc. Process for converting paraffins to olefins
US4523048A (en) * 1984-04-04 1985-06-11 Uop Inc. Process for the selective production of alkylbenzenes
US4705906A (en) * 1985-11-27 1987-11-10 The British Petroleum Company, P.L.C. Selective hydrogenation of acetylene
US4761509A (en) * 1987-02-24 1988-08-02 Uop Inc. High selectivity process for dehydrogenation of paraffinic hydrocarbons
US5177282A (en) * 1989-05-05 1993-01-05 Huels Aktiengesellschaft Oligomerization of olefins
US5281753A (en) * 1992-04-21 1994-01-25 Engelhard Corporation Process for the selective hydrogenation and isomerization of hydrocarbons
US6747181B1 (en) * 1998-04-28 2004-06-08 Dsm N.V. Process for the hydrogenation of phenyl acetylene in a styrene-containing medium with the aid of a catalyst
WO2000064846A1 (en) * 1999-04-27 2000-11-02 Phillips Petroleum Company Hydrocarbon hydrogenation catalyst and process
US6417135B1 (en) 1999-08-27 2002-07-09 Huntsman Petrochemical Corporation Advances in dehydrogenation catalysis
US6700028B2 (en) 1999-08-27 2004-03-02 Huntsman Petrochemical Corporation Advances in dehydrogenation catalysis
US6469223B2 (en) 2000-01-04 2002-10-22 Fina Technology, Inc. Selective hydrogenation of dienes
US20030229285A1 (en) * 2002-06-11 2003-12-11 Simpson David Hope Ultrasonic diagnostic micro-vascular imaging

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DE1926503C3 (de) 1975-03-20
FR2009433A1 (enrdf_load_stackoverflow) 1970-02-06
DE1926503A1 (de) 1970-01-02
GB1218507A (en) 1971-01-06
DE1926503B2 (de) 1973-05-24

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