GB694961A - Improvements in or relating to the conversion of phenanthrene to anthracene - Google Patents

Improvements in or relating to the conversion of phenanthrene to anthracene

Info

Publication number
GB694961A
GB694961A GB12105/50A GB1210550A GB694961A GB 694961 A GB694961 A GB 694961A GB 12105/50 A GB12105/50 A GB 12105/50A GB 1210550 A GB1210550 A GB 1210550A GB 694961 A GB694961 A GB 694961A
Authority
GB
United Kingdom
Prior art keywords
sym
isomerization
octahydroanthracene
octahydrophenanthrene
phenanthrene
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
GB12105/50A
Inventor
Edward Teggin Borrows
Herbert Max Emil Steiner
Isaac Goodman
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.)
PETROCARBON Ltd
Original Assignee
PETROCARBON 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
Priority to BE503246D priority Critical patent/BE503246A/xx
Application filed by PETROCARBON Ltd filed Critical PETROCARBON Ltd
Priority to GB12105/50A priority patent/GB694961A/en
Priority to FR1036924D priority patent/FR1036924A/en
Priority to DEP5530A priority patent/DE857042C/en
Publication of GB694961A publication Critical patent/GB694961A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C07C15/27—Polycyclic condensed hydrocarbons containing three rings
    • C07C15/28—Anthracenes
    • 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
    • C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
    • C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
    • C07C5/2702—Catalytic processes not covered by C07C5/2732 - C07C5/31; Catalytic processes covered by both C07C5/2732 and C07C5/277 simultaneously
    • C07C5/271—Catalytic processes not covered by C07C5/2732 - C07C5/31; Catalytic processes covered by both C07C5/2732 and C07C5/277 simultaneously with inorganic acids; with salts or anhydrides of acids
    • C07C5/2718—Acids of halogen; Salts thereof; complexes thereof with organic compounds
    • C07C5/2721—Metal halides; Complexes thereof with organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
    • C07C7/17—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with acids or sulfur oxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/24—Anthracenes; Hydrogenated anthracenes

Landscapes

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

Abstract

Phenanthrene is converted to anthracene by a process which p comprises the steps of hydrogenating phenanthrene to sym.-octahydrophenanthrene, isomerizing the latter at a temperature of 5 DEG to 45 DEG C. in the presence of dispersed, finely-divided aluminium chloride as isomerization catalyst to form sym.-octahydroanthracene and dehydrogenating the latter to form anthracene. The invention also consists in a process for the isomerization of sym.-octahydrophenanthrene to sym.-octahydroanthracene in which the isomerization is carried out in the presence of dispersed finely-divided aluminium chloride as isomerization catalyst within the temperature range of 5 DEG to 45 DEG C., preferably between 15 DEG and 35 DEG C. Up to about 10 per cent of by-product formed in a previous isomerization reaction may be added to the isomerizing material. The hydrogenation of phenanthrene may be carried out in the presence of a nickel catalyst under pressure and at 100-150 DEG C. whilst the dehydrogenation of sym.-octahydroanthracene may be carried out in the presence of a palladium or platinum catalyst at atmospheric pressure or below and at a temperature between 300 DEG and 350 DEG C. The sym.-octahydrophenanthrene may be purified before subjecting it to the isomerization step and this may be effected by fractional distillation or the hydrogenation product may be purified by sulphonation and conversion of the sulphonic acid formed to a sulphonate which is crystallized out and desulphonated. The sulphonation may be effected with concentrated sulphuric acid at 70 DEG C. and the sulphonic acid dissolved in water and converted to the sodium sulphonate with caustic soda. The sulphonate is then precipitated with saturated sodium chloride solution and the precipitated salt desulphonated by hydrolysis with boiling aqueous sulphuric acid or by heating with an excess of concentrated hydrochloric acid at 160 DEG to 180 DEG C. for 6 to 8 hours in a corrosion-resistant vessel closed to the atmosphere. Sym.-octahydroanthracene may be recovered from the isomerization step by dissolving the product in an organic solvent such as toluene and immediately hydrolysing the metal chloride complex with dilute hydrochloric acid and washing, drying and fractionally distilling the toluene layer to yield a C14 fraction which on filtration and pressing or on centrifuging yields the almost pure hydrocarbon. Either the latter or the C14 fraction may be submitted to the dehydrogenation. The isomerization step is preferably carried out with anhydrous aluminium chloride in an amount of 2.5 to 5 per cent by weight of the sym.-octahydrophenanthrene and for a period of from 10 to 24 hours. Examples are given.
GB12105/50A 1950-05-15 1950-05-15 Improvements in or relating to the conversion of phenanthrene to anthracene Expired GB694961A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
BE503246D BE503246A (en) 1950-05-15
GB12105/50A GB694961A (en) 1950-05-15 1950-05-15 Improvements in or relating to the conversion of phenanthrene to anthracene
FR1036924D FR1036924A (en) 1950-05-15 1951-05-09 Improvements in processes for the conversion of phenanthrene into anthracene
DEP5530A DE857042C (en) 1950-05-15 1951-05-11 Process for converting phenanthrene into anthracene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB12105/50A GB694961A (en) 1950-05-15 1950-05-15 Improvements in or relating to the conversion of phenanthrene to anthracene

Publications (1)

Publication Number Publication Date
GB694961A true GB694961A (en) 1953-07-29

Family

ID=9998479

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12105/50A Expired GB694961A (en) 1950-05-15 1950-05-15 Improvements in or relating to the conversion of phenanthrene to anthracene

Country Status (4)

Country Link
BE (1) BE503246A (en)
DE (1) DE857042C (en)
FR (1) FR1036924A (en)
GB (1) GB694961A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3336407A (en) * 1964-02-27 1967-08-15 Sun Oil Co Catalytic conversion of 1, 2, 3, 4-tetrahydronaphthalene, indan, and other materials
US3389188A (en) * 1966-04-21 1968-06-18 Koppers Co Inc Process for preparing anthracene from phenanthrene
US4367360A (en) * 1981-09-18 1983-01-04 Koppers Company, Inc. Method for product isolation and catalyst recovery in aluminum chloride catalyzed isomerization of sym-octahydrophenanthrene to sym-octahydroanthracene
US4376223A (en) * 1982-04-26 1983-03-08 Koppers Company, Inc. Method for promoting aluminum chloride catalyzed isomerization of sym octahydrophenanthrene to sym-octahydroanthracene with aryl phenone
US4376224A (en) * 1982-04-26 1983-03-08 Koppers Company, Inc. Aluminum chloride catalyzed isomerization of sym-octahydrophenanthrene to sym-octahydroanthracene with acyl peroxide
US4384156A (en) * 1982-03-05 1983-05-17 Koppers Company, Inc. Method for promoting aluminum chloride catalyzed isomerization of sym-octahydrophenanthrene to sym-octahydroanthracene with aroyl halide
US4384152A (en) * 1979-12-22 1983-05-17 Bergwerksverband Gmbh Anthracene production from phenanthrene
US4385194A (en) * 1982-03-05 1983-05-24 Koppers Company, Inc. Method for promoting aluminum chloride catalyzed isomerization of _sym-octahydrophenanthrene to sym-octahydroanthracene with aralkyl halide

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3336407A (en) * 1964-02-27 1967-08-15 Sun Oil Co Catalytic conversion of 1, 2, 3, 4-tetrahydronaphthalene, indan, and other materials
US3389188A (en) * 1966-04-21 1968-06-18 Koppers Co Inc Process for preparing anthracene from phenanthrene
US4384152A (en) * 1979-12-22 1983-05-17 Bergwerksverband Gmbh Anthracene production from phenanthrene
US4367360A (en) * 1981-09-18 1983-01-04 Koppers Company, Inc. Method for product isolation and catalyst recovery in aluminum chloride catalyzed isomerization of sym-octahydrophenanthrene to sym-octahydroanthracene
US4384156A (en) * 1982-03-05 1983-05-17 Koppers Company, Inc. Method for promoting aluminum chloride catalyzed isomerization of sym-octahydrophenanthrene to sym-octahydroanthracene with aroyl halide
US4385194A (en) * 1982-03-05 1983-05-24 Koppers Company, Inc. Method for promoting aluminum chloride catalyzed isomerization of _sym-octahydrophenanthrene to sym-octahydroanthracene with aralkyl halide
US4376223A (en) * 1982-04-26 1983-03-08 Koppers Company, Inc. Method for promoting aluminum chloride catalyzed isomerization of sym octahydrophenanthrene to sym-octahydroanthracene with aryl phenone
US4376224A (en) * 1982-04-26 1983-03-08 Koppers Company, Inc. Aluminum chloride catalyzed isomerization of sym-octahydrophenanthrene to sym-octahydroanthracene with acyl peroxide

Also Published As

Publication number Publication date
DE857042C (en) 1952-11-27
FR1036924A (en) 1953-09-14
BE503246A (en)

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