GB871804A - Improvements in the partial hydrogenation of acetylene compounds - Google Patents

Improvements in the partial hydrogenation of acetylene compounds

Info

Publication number
GB871804A
GB871804A GB3566/58A GB356658A GB871804A GB 871804 A GB871804 A GB 871804A GB 3566/58 A GB3566/58 A GB 3566/58A GB 356658 A GB356658 A GB 356658A GB 871804 A GB871804 A GB 871804A
Authority
GB
United Kingdom
Prior art keywords
cadmium
zinc
acetylene
compounds
triple
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
GB3566/58A
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB871804A publication Critical patent/GB871804A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44—Palladium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/60—Platinum group metals with zinc, cadmium or mercury
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or 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
    • C07C5/08—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds
    • C07C5/09—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds to carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/58—Platinum group metals with alkali- or alkaline earth metals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/63—Platinum group metals with rare earths or actinides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/03—Precipitation; Co-precipitation
    • 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
    • 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
    • C07C2523/06—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of zinc, cadmium or mercury
    • 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
    • C07C2523/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of rare earths
    • 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
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Partial hydrogenation (i.e. conversion of triple to double bond) of acetylene compounds (with or without a solvent) is catalysed by palladium which has been treated with an aqueous or organic solution of a salt of zinc, cadmium, mercury, gallium, indium or thallium, or mixtures thereof; the catalyst may be applied to a carrier such as calcium or barium carbonate, barium sulphate, active carbon or silica gel. The hydrogenation process is preferably carried out in presence of an amine, which term includes ammonia, aliphatic amines (e.g. methylamine), pyridine, quinoline and piperidine. Numerous metal compounds are mentioned, those specified in examples being zinc, cadmium and mercuric acetates; and thallic chlorides. In examples, almost 100% yield is generally obtained of compounds containing a double bond in place of the triple bond in the following:-2:6-dimethyloctene-2-ine-7-ol-6, butine-2-diol-1:4, 2-methylbutine-3-ol-2, 3-piperidinobutine-1, 1-ethinylcyclohexene - 1, propargyl alcohol, ethinyl-beta-ionol (obtained by reaction of beta-ionone with acetylene) and isopropenyl acetylene. Specification 804,788 is referred to.ALSO:Partial hydrogenation (i.e. conversion of triple to double bond) of acetylene compounds (with or without a solvent) is catalysed by palladium which has been treated with an aqueous or organic solution of a salt of zinc, cadmium, mercury, gallium, indium or thallium, or mixtures thereof; the catalyst may be applied to a carrier such as calcium or barium carbonate, barium sulphate, active carbon or silica gel. The hydrogenation process is preferably carried out in presence of an amine, which term includes ammonia, aliphatic amines (e.g. methylamine), pyridine, quinoline and piperidine. Numerous metal compounds are mentioned, those specified in examples being zinc, cadmium and mercuric acetates; and thallic chloride. Specification 804,788 is referred to.
GB3566/58A 1957-02-05 1958-02-04 Improvements in the partial hydrogenation of acetylene compounds Expired GB871804A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB43385A DE1115238B (en) 1957-02-05 1957-02-05 Process for the partial hydrogenation of acetylene compounds

Publications (1)

Publication Number Publication Date
GB871804A true GB871804A (en) 1961-06-28

Family

ID=6967030

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3566/58A Expired GB871804A (en) 1957-02-05 1958-02-04 Improvements in the partial hydrogenation of acetylene compounds

Country Status (6)

Country Link
BE (1) BE564339A (en)
CH (1) CH367484A (en)
DE (1) DE1115238B (en)
FR (1) FR1190949A (en)
GB (1) GB871804A (en)
NL (1) NL102759C (en)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4228088A (en) * 1977-12-19 1980-10-14 Lever Brothers Company Selective hydrogenation
US4307026A (en) 1979-06-19 1981-12-22 Lever Brothers Company Process for the selective hydrogenation of triglyceride oils with a metallic catalyst in the presence of a diamine
US5063194A (en) * 1989-08-11 1991-11-05 Basf Aktiengesellschaft Palladium catalyst
US5356851A (en) * 1992-04-02 1994-10-18 Institut Francais Du Petrole Catalyst containing a group VIII metal and a group IIIA metal deposited on a support
US5364998A (en) * 1992-04-02 1994-11-15 Institut Francais Du Petrole Process for the selective hydrogenation of hydrocarbons
US5521139A (en) * 1993-09-30 1996-05-28 Basf Aktiengesellschaft Palladium-containing fixed-bed catalyst for the hydrogenation of butyne-1,4-diol to butene-2-diol-1,2
US5714644A (en) * 1994-07-06 1998-02-03 Basf Aktiengesellschaft Process and catalyst for the selective hydrogenation of butynediol to butenediol
US5750806A (en) * 1995-07-20 1998-05-12 Basf Aktiengesellschaft Preparation of alkenes by partial hydrogenation of alkynes over fixed-bed palladium catalysts
US6365790B2 (en) 1999-12-23 2002-04-02 Basf Aktiengesellschaft Preparation of C10-C30-alkenes by partial hydrogenation of alkynes over fixed-bed supported palladium catalysts
EP1236512A1 (en) * 2001-02-28 2002-09-04 Council Of Scientific And Industrial Research Nanosized noble metal catalyst and process for selective preparation of 1,4 butenediol
US7045670B2 (en) * 2003-09-03 2006-05-16 Synfuels International, Inc. Process for liquid phase hydrogenation
EP2444155A1 (en) * 2003-09-03 2012-04-25 Synfuels International, Inc. Method of producing catalyst formulation for hydrogenation
US8921631B2 (en) 2008-12-18 2014-12-30 Saudi Basic Industries Corporation Selective catalytic hydrogenation of alkynes to corresponding alkenes
WO2016195954A1 (en) * 2015-05-29 2016-12-08 Uop Llc Process for the selective hydrogenation of acetylene to ethylene

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1180724B (en) * 1959-02-21 1964-11-05 Exxon Research Engineering Co Process for the production of alkyl aromatics by reacting polypropylenes with benzene
DE1181698B (en) * 1961-03-01 1964-11-19 Lab Riuniti Studi E Ricerche S Process for the production of methylbutenol by catalytic hydrogenation of methylbutynol
CH438269A (en) * 1963-05-10 1967-06-30 Snam Spa Hydrogenation process of acetylenic compounds miscible with water to ethylene compounds
US3450776A (en) * 1968-02-16 1969-06-17 Snam Progetti Process for the hydrogenation of water-miscible acetylene compounds into olefin compounds
DE2431929C3 (en) * 1974-07-03 1981-04-02 Basf Ag, 6700 Ludwigshafen Partial hydrogenation catalyst
IT1038403B (en) * 1975-05-23 1979-11-20 Snam Progetti PROCEDURE OF SELECTIVE HYDROGENATION IN THE GASEOUS PHASE OF MULTI-UNSATURATED COMPOUNDS
DE2525506C2 (en) * 1975-06-07 1983-09-15 Basf Ag, 6700 Ludwigshafen Process for the preparation of a catalyst containing nickel and / or cobalt and zinc oxide
FR2552078B1 (en) * 1983-09-19 1986-05-02 Inst Francais Du Petrole PROCESS FOR SELECTIVE HYDROGENATION OF ACETYLENE CONTAINED IN A MIXTURE OF ACETYLENE AND ETHYLENE
FR2553760B1 (en) * 1983-10-25 1986-05-02 Inst Francais Du Petrole PROCESS FOR SELECTIVE HYDROGENATION IN THE PRESENCE OF SOLVENT OF ACETYLENIC COMPOUNDS OF A BUTADIAN RICH C4 HYDROCARBON CUT
DE3444112A1 (en) * 1984-12-04 1986-06-05 Basf Ag, 6700 Ludwigshafen METHOD FOR PRODUCING OLEFINICALLY UNSATURATED COMPOUNDS, IN PARTICULAR ALKENOLS
ATE162785T1 (en) * 1993-10-13 1998-02-15 Hoffmann La Roche PRODUCTION OF AN INTERMEDIATE PRODUCT FOR VITAMIN A ACETATE

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE253160C (en) * 1900-01-01
DE734312C (en) * 1938-07-20 1943-04-13 Ig Farbenindustrie Ag Process for the preparation of 1,4-butenediols
DE859616C (en) * 1951-05-22 1952-12-15 Hoffmann La Roche Ag Deutsche Process for the preparation of doubly unsaturated aliphatic-cyclic 2-methylbutanal compounds

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4228088A (en) * 1977-12-19 1980-10-14 Lever Brothers Company Selective hydrogenation
US4307026A (en) 1979-06-19 1981-12-22 Lever Brothers Company Process for the selective hydrogenation of triglyceride oils with a metallic catalyst in the presence of a diamine
US5063194A (en) * 1989-08-11 1991-11-05 Basf Aktiengesellschaft Palladium catalyst
US5356851A (en) * 1992-04-02 1994-10-18 Institut Francais Du Petrole Catalyst containing a group VIII metal and a group IIIA metal deposited on a support
US5364998A (en) * 1992-04-02 1994-11-15 Institut Francais Du Petrole Process for the selective hydrogenation of hydrocarbons
US5521139A (en) * 1993-09-30 1996-05-28 Basf Aktiengesellschaft Palladium-containing fixed-bed catalyst for the hydrogenation of butyne-1,4-diol to butene-2-diol-1,2
US5714644A (en) * 1994-07-06 1998-02-03 Basf Aktiengesellschaft Process and catalyst for the selective hydrogenation of butynediol to butenediol
US5750806A (en) * 1995-07-20 1998-05-12 Basf Aktiengesellschaft Preparation of alkenes by partial hydrogenation of alkynes over fixed-bed palladium catalysts
US6365790B2 (en) 1999-12-23 2002-04-02 Basf Aktiengesellschaft Preparation of C10-C30-alkenes by partial hydrogenation of alkynes over fixed-bed supported palladium catalysts
EP1236512A1 (en) * 2001-02-28 2002-09-04 Council Of Scientific And Industrial Research Nanosized noble metal catalyst and process for selective preparation of 1,4 butenediol
US7045670B2 (en) * 2003-09-03 2006-05-16 Synfuels International, Inc. Process for liquid phase hydrogenation
EP2444155A1 (en) * 2003-09-03 2012-04-25 Synfuels International, Inc. Method of producing catalyst formulation for hydrogenation
EP2444154A1 (en) * 2003-09-03 2012-04-25 Synfuels International, Inc. Method of screening catalyst formulation for liquid-phase selective hydrogenation
US8921631B2 (en) 2008-12-18 2014-12-30 Saudi Basic Industries Corporation Selective catalytic hydrogenation of alkynes to corresponding alkenes
WO2016195954A1 (en) * 2015-05-29 2016-12-08 Uop Llc Process for the selective hydrogenation of acetylene to ethylene
US9732015B2 (en) 2015-05-29 2017-08-15 Uop Llc Process for the selective hydrogenation of acetylene to ethylene
EA033888B1 (en) * 2015-05-29 2019-12-05 Юоп Ллк Process for the selective hydrogenation of acetylene to ethylene

Also Published As

Publication number Publication date
FR1190949A (en) 1959-10-15
BE564339A (en) 1900-01-01
NL102759C (en) 1900-01-01
CH367484A (en) 1963-02-28
DE1115238B (en) 1961-10-19

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