DE2426495B2 - Verfahren zur herstellung von aethylenglykol und methanol - Google Patents

Verfahren zur herstellung von aethylenglykol und methanol

Info

Publication number
DE2426495B2
DE2426495B2 DE19742426495 DE2426495A DE2426495B2 DE 2426495 B2 DE2426495 B2 DE 2426495B2 DE 19742426495 DE19742426495 DE 19742426495 DE 2426495 A DE2426495 A DE 2426495A DE 2426495 B2 DE2426495 B2 DE 2426495B2
Authority
DE
Germany
Prior art keywords
ethylene glycol
rhodium
reaction
methanol
concentration
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.)
Withdrawn
Application number
DE19742426495
Other languages
German (de)
English (en)
Other versions
DE2426495A1 (de
Inventor
Wellington Epler Charleston; Cropley Jean Bowman South Charleston; W.Va. Walker (V.St.A.)
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.)
Union Carbide Corp
Original Assignee
Union Carbide Corp
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 Union Carbide Corp filed Critical Union Carbide Corp
Publication of DE2426495A1 publication Critical patent/DE2426495A1/de
Publication of DE2426495B2 publication Critical patent/DE2426495B2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0241—Imines or enamines
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/20—Carbonyls
    • 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
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/1512—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by reaction conditions
    • 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
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/1512—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by reaction conditions
    • C07C29/1514—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by reaction conditions the solvents being characteristic
    • 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
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/152—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the reactor used
    • 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
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/153—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used
    • C07C29/156—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing iron group metals, platinum group metals or compounds thereof
    • C07C29/157—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing iron group metals, platinum group metals or compounds thereof containing platinum group metals or compounds thereof
    • C07C29/158—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing iron group metals, platinum group metals or compounds thereof containing platinum group metals or compounds thereof containing rhodium or compounds thereof
    • 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
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/648—Fischer-Tropsch-type reactions
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0202—Polynuclearity
    • B01J2531/0211—Metal clusters, i.e. complexes comprising 3 to about 1000 metal atoms with metal-metal bonds to provide one or more all-metal (M)n rings, e.g. Rh4(CO)12
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/822—Rhodium
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/40—Regeneration or reactivation
    • B01J31/4015—Regeneration or reactivation of catalysts containing metals
    • B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
    • B01J31/4038—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals
    • B01J31/4046—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals containing rhodium
    • 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
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
    • 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
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
DE19742426495 1973-06-19 1974-05-31 Verfahren zur herstellung von aethylenglykol und methanol Withdrawn DE2426495B2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US37135373A 1973-06-19 1973-06-19
US05/470,115 US3940432A (en) 1973-06-19 1974-05-15 Process for making ethylene glycol

Publications (2)

Publication Number Publication Date
DE2426495A1 DE2426495A1 (de) 1975-01-09
DE2426495B2 true DE2426495B2 (de) 1976-10-28

Family

ID=27005345

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19742426495 Withdrawn DE2426495B2 (de) 1973-06-19 1974-05-31 Verfahren zur herstellung von aethylenglykol und methanol

Country Status (17)

Country Link
US (1) US3940432A (enExample)
JP (1) JPS5315047B2 (enExample)
AR (1) AR214706A1 (enExample)
AU (1) AU497318B2 (enExample)
BE (1) BE815841A (enExample)
BR (1) BR7404468D0 (enExample)
CA (1) CA1031375A (enExample)
DE (1) DE2426495B2 (enExample)
ES (1) ES426807A1 (enExample)
FR (1) FR2234257B1 (enExample)
GB (1) GB1477392A (enExample)
IL (1) IL44944A (enExample)
IN (1) IN142807B (enExample)
IT (1) IT1017012B (enExample)
NL (1) NL7407383A (enExample)
SE (1) SE415561B (enExample)
ZA (1) ZA743313B (enExample)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4228094A (en) * 1976-08-19 1980-10-14 Union Carbide Corporation Ethylene glycol extraction process
GB1568427A (en) * 1976-10-21 1980-05-29 Chevron Res Process for preparing glycol and methanol
US4111975A (en) * 1977-03-30 1978-09-05 Union Carbide Corporation Catalytic process for producing polyhydric alcohols and derivatives
US4168391A (en) * 1977-12-05 1979-09-18 Celanese Corporation Production of ethanol from methanol
EP0002908B1 (en) * 1977-12-16 1982-05-12 Monsanto Company Hydroformylation of formaldehyde with rhodium catalyst
US4211719A (en) * 1978-02-13 1980-07-08 Union Carbide Corporation Catalytic process for polyhydric alcohols and derivatives
US4192777A (en) * 1978-03-01 1980-03-11 Exxon Research & Engineering Co. Preparation and use of supported potassium (or rubidium)-Group VIII-metal cluster catalysts in CO/H2 Fischer-Tropsch synthesis reactions
US4224236A (en) * 1978-04-04 1980-09-23 Hoechst Aktiengesellschaft Process for the manufacture of oxygen-containing carbon compounds from synthesis gas
DE2960477D1 (en) * 1978-04-04 1981-10-22 Hoechst Ag Process for the preparation of oxygenated hydrocarbon compounds starting from a synthesis gas
US4170606A (en) * 1978-04-06 1979-10-09 Gulf Research And Development Company Synthesis of ethylene glycol from carbon monoxide and hydrogen using an iridium complex catalyst and a pyridine base ligand
DE2941998A1 (de) * 1978-12-11 1980-06-19 Texaco Development Corp Verfahren zur gleichzeitigen herstellung von estern, von alkanolen und vicinalen glykolen
US4224235A (en) * 1978-12-11 1980-09-23 Union Carbide Corporation Rhodium catalyst regeneration by thermal treatment
US4348539A (en) * 1979-11-01 1982-09-07 Union Carbide Corporation Heteronuclear-bridged rhodium clusters
US4288380A (en) * 1979-11-01 1981-09-08 Union Carbide Corporation Heteronuclear-bridged rhodium clusters
US4265828A (en) * 1979-12-31 1981-05-05 Texaco Development Corp. Manufacture of ethylene glycol from synthesis gas
EP0033212A3 (en) * 1980-01-24 1981-09-09 The British Petroleum Company p.l.c. Process for the production of oxygenated hydrocarbons from synthesis gas
JPS5779001U (enExample) * 1980-11-04 1982-05-15
CA1172262A (en) * 1980-12-24 1984-08-07 Barbara K. Warren Process for the production of ethylene glycol
US4399233A (en) * 1982-03-11 1983-08-16 Texaco Inc. Process for preparing low molecular weight oxygenated compounds from syngas using novel catalyst system
KR930003649B1 (ko) * 1990-10-05 1993-05-08 재단법인 한국화학연구소 에틸리덴 디 아세테이트 제조용 고체촉매, 그의 제조방법 및 이를 이용한 연속식, 공정에 의한 에틸리덴 디 아세테이트의 제조방법
KR930003650B1 (ko) * 1990-10-08 1993-05-08 재단법인 한국화학연구소 에틸리덴 디 아세테이트 제조용 유기체 담지 촉매 및 이를 이용한 에틸리덴 디 아세테이트의 제조방법
WO2002087809A1 (en) * 2001-04-27 2002-11-07 Dowa Mining Co., Ltd. Copper powder for electroconductive paste excellent in resistance to oxidation and method for preparation thereof
DE102007027372A1 (de) * 2007-06-11 2008-12-18 Cognis Oleochemicals Gmbh Verfahren zur Hydrierung von Glycerin
CN102952009B (zh) * 2012-08-06 2015-07-22 刘长宝 利用乙二醇生产琥珀酸和1,4-丁二醇的方法、工艺和生产线

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1741307A (en) * 1925-09-09 1929-12-31 Selden Co Process of reducing products of carbon monoxide
GB655237A (en) * 1947-12-23 1951-07-11 Du Pont Improvements in the preparation of glycol and glycerol and their esters
US2636046A (en) * 1948-10-16 1953-04-21 Du Pont Preparation of polyfunctional compounds
US2534018A (en) * 1949-08-11 1950-12-12 Du Pont Preparation of polyfunctional compounds
US3081357A (en) * 1960-05-24 1963-03-12 Du Pont Process for producing alkanediols
US3310576A (en) * 1963-02-05 1967-03-21 Exxon Research Engineering Co Hydroformylation catalyst and process relating thereto
US3644446A (en) * 1969-07-01 1972-02-22 Union Oil Co Preparation of rhodium and iridium hydride carbonyl complexes
US3833634A (en) * 1971-12-21 1974-09-03 Union Carbide Corp Manufacture of polyfunctional compounds

Also Published As

Publication number Publication date
AU497318B2 (en) 1978-12-07
JPS5315047B2 (enExample) 1978-05-22
IL44944A (en) 1977-10-31
AU6953174A (en) 1975-12-04
BE815841A (en) 1974-12-02
US3940432A (en) 1976-02-24
GB1477392A (en) 1977-06-22
BR7404468D0 (pt) 1975-09-30
AR214706A1 (es) 1979-07-31
CA1031375A (en) 1978-05-16
NL7407383A (enExample) 1974-12-23
DE2426495A1 (de) 1975-01-09
ZA743313B (en) 1975-05-28
SE415561B (sv) 1980-10-13
FR2234257A1 (enExample) 1975-01-17
IL44944A0 (en) 1974-07-31
JPS5032117A (enExample) 1975-03-28
SE7407278L (enExample) 1974-12-20
ES426807A1 (es) 1976-09-16
IT1017012B (it) 1977-07-20
IN142807B (enExample) 1977-08-27
FR2234257B1 (enExample) 1978-01-20

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Legal Events

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8230 Patent withdrawn