GB1272592A - Vapour phase oxidation of hydroxy compounds - Google Patents

Vapour phase oxidation of hydroxy compounds

Info

Publication number
GB1272592A
GB1272592A GB2142268A GB2142268A GB1272592A GB 1272592 A GB1272592 A GB 1272592A GB 2142268 A GB2142268 A GB 2142268A GB 2142268 A GB2142268 A GB 2142268A GB 1272592 A GB1272592 A GB 1272592A
Authority
GB
United Kingdom
Prior art keywords
glyoxal
glycol
compounds
present
formaldehyde
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
GB2142268A
Inventor
Brian Keith Howe
Francis Robert Frederick Hardy
Douglas Alfred Clarke
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.)
Evonik LCL Ltd
Original Assignee
Laporte Chemicals Ltd
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 Laporte Chemicals Ltd filed Critical Laporte Chemicals Ltd
Priority to GB2142268A priority Critical patent/GB1272592A/en
Priority to NO184469A priority patent/NO133034C/no
Priority to NL6906866A priority patent/NL168487C/en
Priority to CH684269A priority patent/CH535193A/en
Priority to SE637769A priority patent/SE363816B/xx
Priority to FR6914418A priority patent/FR2007925A1/fr
Priority to DE19691967147 priority patent/DE1967147C2/en
Priority to BE732584D priority patent/BE732584A/xx
Priority to BR20855169A priority patent/BR6908551D0/en
Priority to ES366867A priority patent/ES366867A1/en
Priority to DE19691923048 priority patent/DE1923048C3/en
Publication of GB1272592A publication Critical patent/GB1272592A/en
Priority to JP8137872A priority patent/JPS4930807B1/ja
Priority to US05/451,228 priority patent/US3948997A/en
Priority to NLAANVRAGE8104458,A priority patent/NL175291C/en
Expired 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/835—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with germanium, tin or lead
    • 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
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/843—Arsenic, antimony or bismuth
    • 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
    • C07C45/38—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 being a primary hydroxyl group
    • 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
    • C07C45/39—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 being a secondary hydroxyl group
    • 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
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
    • 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
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/783—Separation; Purification; Stabilisation; Use of additives by gas-liquid treatment, e.g. by gas-liquid absorption
    • 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
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
    • 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
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • 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
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/17—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/185—Saturated compounds containing keto groups bound to acyclic carbon atoms containing —CHO groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/40—Two or more oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Paper (AREA)

Abstract

1,272,592. Oxidizing hydroxy compounds to carbonyl compounds. LAPORTE CHEMICALS Ltd. 6 Aug., 1969 [6 May, 1968], No. 21422/68. Heading C2C. Carbonyl compounds are prepared by the vapour phase oxidation of corresponding hydroxy compounds by contacting at elevated temperature a gaseous mixture containing oxygen and the hydroxy compound with a catalyst containing as essential constituents one or more of Cu and Ag with P as a promoter. Au, As, Sb and/or Sn may also be present. The catalyst may be a mixture of particulate ingredients or may be an alloy, the surface of which may be oxidized prior to use. It may be supported. The oxygen may be introduced at more than one point along the reaction. A diluent gas may be present. The reaction product after removal of readily condensable products may be recycled. Examples oxidize ethylene glycol to glyoxal with some glycollic aldehyde, glycollic acid and formaldehyde, propylene - 1,2 - glycol to methylglyoxal and acetol, butene-2,3-diol to diacetyl and acetoin, and cyclohexan - 1,2 - diol to cyclohexan - 1,2- dione. Reference is also made to the oxidation of C 1-6 aliphatic alcohols, cyclohexanol and benzyl alcohol. In the oxidation of ethylene glycol to glyoxal, unreacted glycol may be removed by cooling the reaction gases to a temperature below the condensation point of ethylene glycol but above that of glyoxal. The glycol reacts with some of the glyoxal to give 2,3-dihydroxydioxan. After separating the condensed material, which may be recycled, an aqueous solution of glyoxal may be formed from the remaining reaction gases. Formaldehyde may be removed from this solution by purging with a gas at elevated temperature and acidic impurities, mainly glycollic acid, by treatment with a weakly basic anion exchange resin in the free base form. Glyoxal prepared as above may be reacted with urea to give 4, 5-dihydroxy-2-ketoimidazolidine. If formaldehyde is also present the 1- and 1,3 - methylol - 4,5 - dihydroxy - 2 - ketoimidazolidines are formed or if an alkanol is also present the 0-alkylmethylol compounds.
GB2142268A 1968-05-06 1968-05-06 Vapour phase oxidation of hydroxy compounds Expired GB1272592A (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
GB2142268A GB1272592A (en) 1968-05-06 1968-05-06 Vapour phase oxidation of hydroxy compounds
NO184469A NO133034C (en) 1968-05-06 1969-05-05
NL6906866A NL168487C (en) 1968-05-06 1969-05-05 METHOD FOR OXIDIZING DIOLS IN THE VAPOR PHASE TO THE COMPATIBLE DICARBONYL COMPOUNDS.
CH684269A CH535193A (en) 1968-05-06 1969-05-05 Process for the preparation of carbonyl compounds
BE732584D BE732584A (en) 1968-05-06 1969-05-06
FR6914418A FR2007925A1 (en) 1968-05-06 1969-05-06
DE19691967147 DE1967147C2 (en) 1968-05-06 1969-05-06 Process for the production of glyoxal by vapor phase oxidation of ethylene glycol
SE637769A SE363816B (en) 1968-05-06 1969-05-06
BR20855169A BR6908551D0 (en) 1968-05-06 1969-05-06 A CATALYTIC OXIDATION PROCESS OF HYDROXY COMPOUNDS
ES366867A ES366867A1 (en) 1968-05-06 1969-05-06 Vapour phase oxidation of hydroxy compounds
DE19691923048 DE1923048C3 (en) 1968-05-06 1969-05-06 Process for the preparation of dicarbonyl compounds by vapor phase oxidation of an aliphatic diol or of cyclohexane-1,2-diol
JP8137872A JPS4930807B1 (en) 1968-05-06 1972-08-14
US05/451,228 US3948997A (en) 1968-05-06 1974-03-14 Vapour phase oxidation process
NLAANVRAGE8104458,A NL175291C (en) 1968-05-06 1981-09-29 METHOD FOR OXIDIZING DIOLS IN THE VAPOR PHASE TO THE COMPATIBLE DICARBONYL COMPOUNDS.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2142268A GB1272592A (en) 1968-05-06 1968-05-06 Vapour phase oxidation of hydroxy compounds

Publications (1)

Publication Number Publication Date
GB1272592A true GB1272592A (en) 1972-05-03

Family

ID=10162679

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2142268A Expired GB1272592A (en) 1968-05-06 1968-05-06 Vapour phase oxidation of hydroxy compounds

Country Status (11)

Country Link
JP (1) JPS4930807B1 (en)
BE (1) BE732584A (en)
BR (1) BR6908551D0 (en)
CH (1) CH535193A (en)
DE (2) DE1923048C3 (en)
ES (1) ES366867A1 (en)
FR (1) FR2007925A1 (en)
GB (1) GB1272592A (en)
NL (1) NL168487C (en)
NO (1) NO133034C (en)
SE (1) SE363816B (en)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2634439A1 (en) * 1975-07-31 1977-02-10 American Cyanamid Co METHOD FOR MANUFACTURING GLYOXAL
EP0007570A1 (en) * 1978-07-24 1980-02-06 BASF Aktiengesellschaft Process for the preparation of glyoxal from ethylene glycol
US4258216A (en) * 1975-07-31 1981-03-24 American Cyanamid Company Vapor phase oxidation process for glyoxal
JPS5838227A (en) * 1981-09-01 1983-03-05 Mitsui Toatsu Chem Inc Preparation of aldehyde
EP0091060A2 (en) * 1982-04-08 1983-10-12 BASF Aktiengesellschaft Process for producing formaldehyde
US4439625A (en) * 1982-09-29 1984-03-27 E. I. Du Pont De Nemours And Company Production of formaldehyde
US4503261A (en) * 1982-07-22 1985-03-05 Basf Aktiengesellschaft Preparation of glyoxal
US4511739A (en) * 1979-06-02 1985-04-16 Basf Aktiengesellschaft Continuous preparation of glyoxal
US4555583A (en) * 1982-08-30 1985-11-26 Mitsui Toatsu Chemicals, Incorporated Preparation process for glyoxal
US4599459A (en) * 1984-08-31 1986-07-08 Masanao Hirose Method for the ultrasonic treatment of a dilute alcoholic solution
US4851584A (en) * 1987-04-15 1989-07-25 Basf Aktiengesellschaft Preparation of carbonyl compounds
WO2007132011A1 (en) * 2006-05-17 2007-11-22 Basf Aktiengesellschaft Method for producing vicinal dioxo compounds by oxidation of vicinal dihydroxy compounds on a structured catalyst packing
DE102008002535A1 (en) 2007-06-25 2009-01-02 Basf Se Producing vicinal dioxo compounds, preferably glyoxal, useful as cross linker functionalized polymers, comprises gas phase oxidation of vicinal dihydroxy compounds in presence of gases containing oxygen on a catalyst comprising e.g. gold
US8461396B2 (en) 2010-10-01 2013-06-11 Basf Se Process for purifying aqueous glyoxal solutions
WO2022058188A1 (en) 2020-09-17 2022-03-24 Basf Se Process for the production of glyoxal

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5490109A (en) * 1977-12-24 1979-07-17 Basf Ag Manufacture of fatty hydroxycarbonyl compound etherified with fatty group
DE2803318A1 (en) * 1978-01-26 1979-08-09 Basf Ag METHOD FOR MANUFACTURING GLYOXAL
DE3012004A1 (en) * 1980-03-28 1981-10-15 Hoechst Ag, 6000 Frankfurt METHOD FOR PRODUCING METHYLGLYOXAL
DE3643469A1 (en) * 1986-12-19 1988-06-30 Basf Ag METHOD FOR PRODUCING CARBONYL COMPOUNDS
CN101472873A (en) * 2006-05-17 2009-07-01 巴斯夫欧洲公司 Temperature adjustment in oxidation reactions of hydrocarbons
DE102008018480B4 (en) 2007-04-13 2020-10-15 Basf Se Process for the preparation of vicinal dioxo compounds by oxidation of vicinal dihydroxy compounds
CN102272084A (en) 2008-12-29 2011-12-07 巴斯夫欧洲公司 Method for cleaning aqueous glyoxal solutions
EP2621878B1 (en) 2010-10-01 2016-06-01 Basf Se Process for purifying aqueous glyoxal solutions

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1497817A (en) * 1918-08-13 1924-06-17 Seth B Hunt Process of making acetone and other ketones
US2051266A (en) * 1935-03-23 1936-08-18 Shell Dev Catalytic oxidation of polyhydric alcohols
US2462107A (en) * 1943-05-03 1949-02-22 Ninol Dev Co Process for preparation of diacetyl
FR1060331A (en) * 1951-08-02 1954-04-01 Basf Ag Process for obtaining ureins from ethanedial
US3049446A (en) * 1960-02-05 1962-08-14 Sun Chemical Corp Process for the manufacture of urea, glyoxal and formaldehye reaction product useful for improving cellulosic textile materials

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2634439A1 (en) * 1975-07-31 1977-02-10 American Cyanamid Co METHOD FOR MANUFACTURING GLYOXAL
US4258216A (en) * 1975-07-31 1981-03-24 American Cyanamid Company Vapor phase oxidation process for glyoxal
EP0007570A1 (en) * 1978-07-24 1980-02-06 BASF Aktiengesellschaft Process for the preparation of glyoxal from ethylene glycol
US4282374A (en) * 1978-07-24 1981-08-04 Basf Aktiengesellschaft Preparation of glyoxal from ethylene glycol
US4511739A (en) * 1979-06-02 1985-04-16 Basf Aktiengesellschaft Continuous preparation of glyoxal
JPS5838227A (en) * 1981-09-01 1983-03-05 Mitsui Toatsu Chem Inc Preparation of aldehyde
EP0091060A2 (en) * 1982-04-08 1983-10-12 BASF Aktiengesellschaft Process for producing formaldehyde
EP0091060A3 (en) * 1982-04-08 1986-07-23 Basf Aktiengesellschaft Process for producing formaldehyde
US4503261A (en) * 1982-07-22 1985-03-05 Basf Aktiengesellschaft Preparation of glyoxal
US4555583A (en) * 1982-08-30 1985-11-26 Mitsui Toatsu Chemicals, Incorporated Preparation process for glyoxal
EP0104666A2 (en) * 1982-09-29 1984-04-04 E.I. Du Pont De Nemours And Company Production of formaldehyde
EP0104666A3 (en) * 1982-09-29 1985-10-23 E.I. Du Pont De Nemours And Company Production of formaldehyde
US4439625A (en) * 1982-09-29 1984-03-27 E. I. Du Pont De Nemours And Company Production of formaldehyde
US4599459A (en) * 1984-08-31 1986-07-08 Masanao Hirose Method for the ultrasonic treatment of a dilute alcoholic solution
US4851584A (en) * 1987-04-15 1989-07-25 Basf Aktiengesellschaft Preparation of carbonyl compounds
WO2007132011A1 (en) * 2006-05-17 2007-11-22 Basf Aktiengesellschaft Method for producing vicinal dioxo compounds by oxidation of vicinal dihydroxy compounds on a structured catalyst packing
DE102008002535A1 (en) 2007-06-25 2009-01-02 Basf Se Producing vicinal dioxo compounds, preferably glyoxal, useful as cross linker functionalized polymers, comprises gas phase oxidation of vicinal dihydroxy compounds in presence of gases containing oxygen on a catalyst comprising e.g. gold
US8461396B2 (en) 2010-10-01 2013-06-11 Basf Se Process for purifying aqueous glyoxal solutions
WO2022058188A1 (en) 2020-09-17 2022-03-24 Basf Se Process for the production of glyoxal

Also Published As

Publication number Publication date
JPS4930807B1 (en) 1974-08-16
DE1923048C3 (en) 1980-06-19
CH535193A (en) 1973-03-31
DE1923048A1 (en) 1969-11-20
NO133034C (en) 1976-02-25
DE1923048B2 (en) 1979-07-19
DE1967147B1 (en) 1979-06-13
NL168487C (en) 1982-04-16
DE1967147C2 (en) 1980-02-14
NL6906866A (en) 1969-11-10
BE732584A (en) 1969-11-06
BR6908551D0 (en) 1973-01-04
ES366867A1 (en) 1971-06-16
NO133034B (en) 1975-11-17
SE363816B (en) 1974-02-04
FR2007925A1 (en) 1970-01-16
NL168487B (en) 1981-11-16

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