CA1217502A - Conversion of alkanes to unsaturated aldehydes - Google Patents

Conversion of alkanes to unsaturated aldehydes

Info

Publication number
CA1217502A
CA1217502A CA000425653A CA425653A CA1217502A CA 1217502 A CA1217502 A CA 1217502A CA 000425653 A CA000425653 A CA 000425653A CA 425653 A CA425653 A CA 425653A CA 1217502 A CA1217502 A CA 1217502A
Authority
CA
Canada
Prior art keywords
hydrogen
effluent
oxidation
isobutane
oxygen
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
CA000425653A
Other languages
English (en)
French (fr)
Inventor
Sargis Khoobiar
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.)
Halcon SD Group Inc
Original Assignee
Halcon SD Group Inc
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
Priority claimed from US06/368,196 external-priority patent/US4413147A/en
Priority claimed from US06/420,077 external-priority patent/US4535188A/en
Priority claimed from US06/468,524 external-priority patent/US4532365A/en
Application filed by Halcon SD Group Inc filed Critical Halcon SD Group Inc
Application granted granted Critical
Publication of CA1217502A publication Critical patent/CA1217502A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
    • C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
    • 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
    • B01J23/002—Mixed oxides other than spinels, e.g. perovskite
    • 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
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J27/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
    • B01J27/19—Molybdenum
    • B01J27/192—Molybdenum with bismuth
    • 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
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
    • B01J27/198—Vanadium
    • B01J27/199—Vanadium with chromium, molybdenum, tungsten or polonium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
    • C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
    • C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
    • 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
    • C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
    • C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
    • C07C5/333—Catalytic processes
    • C07C5/3332—Catalytic processes with metal oxides or metal sulfides
    • 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
    • C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
    • C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
    • C07C5/333—Catalytic processes
    • C07C5/3335—Catalytic processes with metals
    • C07C5/3337—Catalytic processes with metals of the platinum group
    • 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
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (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)
CA000425653A 1982-04-14 1983-04-12 Conversion of alkanes to unsaturated aldehydes Expired CA1217502A (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US06/368,196 US4413147A (en) 1982-04-14 1982-04-14 Conversion of isobutane to methacrolein
US368,196 1982-04-14
US420,077 1982-09-20
US06/420,077 US4535188A (en) 1982-04-14 1982-09-20 Conversion of isobutane to methacrolein
US06/468,524 US4532365A (en) 1982-09-20 1983-02-22 Conversion of alkanes to unsaturated aldehydes
US468,524 1983-02-22

Publications (1)

Publication Number Publication Date
CA1217502A true CA1217502A (en) 1987-02-03

Family

ID=27408852

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000425653A Expired CA1217502A (en) 1982-04-14 1983-04-12 Conversion of alkanes to unsaturated aldehydes

Country Status (8)

Country Link
AU (1) AU560458B2 (it)
BR (1) BR8301915A (it)
CA (1) CA1217502A (it)
DE (1) DE3313573C2 (it)
FR (1) FR2525212B1 (it)
GB (1) GB2118939B (it)
IT (1) IT1167404B (it)
NL (1) NL8301303A (it)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7321058B2 (en) 2000-06-14 2008-01-22 Basf Aktiengesellschaft Method for producing acrolein and/or acrylic acid

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3461782D1 (en) * 1983-02-22 1987-02-05 Halcon Sd Group Inc Conversion of propane to acrylic acid
DE3800991A1 (de) * 1988-01-15 1989-07-27 Basf Ag Verfahren zur herstellung von (alpha),(beta)-monoolefinisch ungesaettigten 3 bis 4 c-atome enthaltenden carbonsaeuren durch gasphasenoxidation
DE59603316D1 (de) * 1995-03-10 1999-11-18 Basf Ag Verfahren zur Herstellung von Acrolein, Acrylsäure oder deren Gemisch aus Propan
US6492548B1 (en) 1996-04-01 2002-12-10 Union Carbide Chemicals & Plastics Technology Corporation Process for the oxidation of alkanes
DE69713515T2 (de) * 1996-04-01 2003-01-09 Union Carbide Chemicals & Plastics Technology Corp., Danbury Verfahren zur oxidation von alkanen
DE19837517A1 (de) 1998-08-19 2000-02-24 Basf Ag Verfahren zur Herstellung von Acrolein und/oder Acrylsäure aus Propan
DE19837519A1 (de) * 1998-08-19 2000-02-24 Basf Ag Verfahren zur Herstellung von Acrolein und/oder Acrylsäure aus Propan
DE10028582A1 (de) 2000-06-14 2001-12-20 Basf Ag Verfahren zur Herstellung von Acrolein oder Acrylsäure oder deren Gemischen aus Propan
RU2285690C2 (ru) * 2000-06-20 2006-10-20 Басф Акциенгезельшафт Способ получения акролеина и/или акриловой кислоты
KR100900849B1 (ko) 2001-06-29 2009-06-04 바스프 에스이 이소부탄으로부터 메타크릴산을 제조하는 방법
KR100900848B1 (ko) * 2001-06-29 2009-06-04 바스프 에스이 이소부탄으로부터 메타크롤레인을 제조하는 방법
DE10131297A1 (de) * 2001-06-29 2003-01-09 Basf Ag Verfahren zur Herstellung von partiellen Oxidationsprodukten und/oder partiellen Ammoxidationsprodukten wenigstens eines olefinischen Kohlenwasserstoffs
DE10316039A1 (de) 2003-04-07 2004-10-21 Basf Ag Verfahren zur Herstellung von wenigstens einem partiellen Oxidations-und/oder Ammoxidationsprodukt eines Kohlenwasserstoffs
US7592483B2 (en) 2004-07-01 2009-09-22 Basf Aktiengesellschaft Preparation of acrolein or acrylic acid or a mixture thereof by heterogeneously catalyzed partial gas phase oxidation of propylene
US7601866B2 (en) 2005-03-01 2009-10-13 Basf Aktiengesellschaft Process for removing methacrolein from liquid phase comprising acrylic acid as a main constituent and target product, and methacrolein as a secondary component
US7705181B2 (en) 2005-03-01 2010-04-27 Basf Akiengesellschaft Process for removing methacrylic acid from liquid phase comprising acrylic acid as a main constituent and target product, and methacrylic acid as a secondary component
DE502006003491D1 (de) 2005-11-03 2009-05-28 Basf Se Verfahren zum stabilen betreiben eines kontinuierlich ausgeübten herstellprozesses zur erzeugung von acrolein, oder acrylsäure oder deren gemisch aus propan
KR101370749B1 (ko) 2005-11-24 2014-03-06 바스프 에스이 프로판으로부터 아크롤레인 또는 아크릴산, 또는 그의혼합물의 제조 방법
RU2430083C9 (ru) * 2005-11-24 2012-09-20 Басф Се Способ получения акриловой кислоты из пропана
MY143542A (en) * 2005-11-24 2011-05-31 Basf Se Process for preparing acrolein or acrylic acid or a mixture thereof from propane
DE102005062010A1 (de) 2005-12-22 2007-06-28 Basf Ag Verfahren der heterogen katalysierten partiellen Gasphasenoxidation von Propylen zu Acrylsäure
DE102005062026A1 (de) 2005-12-22 2007-06-28 Basf Ag Verfahren der heterogen katalysierten partiellen Gasphasenoxidation von Propylen zu Acrylsäure
DE102006024901A1 (de) 2006-05-24 2007-11-29 Basf Ag Verfahren zur Herstellung von Acrolein, oder Acrylsäure oder deren Gemisch aus Propan
DE102007006647A1 (de) 2007-02-06 2008-08-07 Basf Se Verfahren zur Regenerierung eines im Rahmen einer heterogen katalysierten partiellen Dehydrierung eines Kohlenwasserstoffs deaktivierten Katalysatorbetts
CN101790506A (zh) * 2007-08-30 2010-07-28 株式会社日本触媒 生产丙烯酸的方法
DE102007043759A1 (de) 2007-09-13 2008-09-11 Basf Se Verfahren zum Betreiben einer kontinuierlichen Abtrennung eines Zielproduktes X in Form von feinteiligem Kristallisat
BE1018537A3 (fr) 2007-09-13 2011-03-01 Basf Se Procede d'exploitation d'une separation en continu d'un produit cible x sous la forme d'un cristallisat finement divise.
DE102007043748A1 (de) 2007-09-13 2008-09-11 Basf Se Verfahren zur kontinuierlichen Abtrennung eines Zielproduktes X in Form von feinteiligem Kristallisat
DE102007043758A1 (de) 2007-09-13 2008-10-23 Basf Se Verfahren zum Betreiben einer kontinuierlichen Abtrennung eines Zielproduktes X in Form von feinteiligem Kristallisat des Zielproduktes X
DE102008044946B4 (de) 2008-08-29 2022-06-15 Evonik Superabsorber Gmbh Einsatz von Schaumkörpern in Oxidations-Reaktoren zur Herstellung ungesättigter Carbonsäuren
FR2952053B1 (fr) 2009-11-02 2011-12-16 Air Liquide Procede et dispositif de production de derives d'alcenes

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3161670A (en) * 1960-12-12 1964-12-15 Shell Oil Co Preparation of olefinic compounds
BE623670R (fr) * 1962-07-06 1963-04-16 Stamicarbon Procédé de préparation d'acroléine ou de méthacroléine par oxydation catalytique de propène ou d'isobutène
GB1426303A (en) * 1972-08-25 1976-02-25 Ube Industries Catalyst and process for oxidation of ammoxidation of olefin mixtures
GB1467865A (en) * 1973-07-27 1977-03-23 Basf Ag Catalytic oxidation or ammoxidation of a-olefins to alpha,beta- olefinically unsaturated aldehydes acids or nitriles
JPS5341648B2 (it) * 1974-12-06 1978-11-06
US4335264A (en) * 1976-07-07 1982-06-15 E. I. Du Pont De Nemours And Company High yield, low byproduct α, β-unsaturated aldehydes from olefins
US4217309A (en) * 1978-06-12 1980-08-12 Ube Industries, Ltd. Process for producing methacrolein

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7321058B2 (en) 2000-06-14 2008-01-22 Basf Aktiengesellschaft Method for producing acrolein and/or acrylic acid

Also Published As

Publication number Publication date
AU560458B2 (en) 1987-04-09
DE3313573C2 (de) 1987-05-07
FR2525212A1 (fr) 1983-10-21
IT8348091A1 (it) 1984-10-13
GB2118939B (en) 1986-04-30
DE3313573A1 (de) 1983-10-20
FR2525212B1 (fr) 1986-12-05
IT8348091A0 (it) 1983-04-13
GB2118939A (en) 1983-11-09
NL8301303A (nl) 1983-11-01
BR8301915A (pt) 1983-12-20
IT1167404B (it) 1987-05-13
AU1349283A (en) 1983-10-20
GB8310123D0 (en) 1983-05-18

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Legal Events

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