FR1224885A - Process for preparing mononitroanthraquinones - Google Patents

Process for preparing mononitroanthraquinones

Info

Publication number
FR1224885A
FR1224885A FR785511A FR785511A FR1224885A FR 1224885 A FR1224885 A FR 1224885A FR 785511 A FR785511 A FR 785511A FR 785511 A FR785511 A FR 785511A FR 1224885 A FR1224885 A FR 1224885A
Authority
FR
France
Prior art keywords
nitro
dihalo
isolated
dehydrohalogenation
tetrahydroanthraquinone
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
FR785511A
Other languages
French (fr)
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Application granted granted Critical
Publication of FR1224885A publication Critical patent/FR1224885A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/16—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C07C205/46—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group the carbon skeleton containing carbon atoms of quinone rings
    • C07C205/47—Anthraquinones containing nitro groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A nitro-2,3-dihalo-1,2,3,4-tetrahydro-anthraquinone is obtained by adding nitric acid to a solution of 2,3-dihalo-1,2,3,4-tetrahydroanthraquinone in sulphuric acid of above 93% concentration while keeping the temperature below 60 DEG C. The halo substituent may be chlorine, bromine, or iodine. The nitro-dihalo compound may be heated with aqueous caustic alkali so as to obtain by dehydrohalogenation the 1- or 2-nitroanthraquinones. The dihalo-tetrahydro compound may be obtained by subjecting a 1,4,4a,9a-tetrahydroanthraquinone, in aqueous solution adjusted to a pH of 4-8, to oxidation with gaseous oxygen at 85 DEG C.-100 DEG C., separating the resulting 1,4-dihydroanthraquinone, suspending it in a solvent inert to halogenation, and reacting it with chlorine, bromine, or iodine, or a chlorinating agent such as sulphuryl chloride, to form a 2, 3 - dihalo - 1,2,3,4 - tetrahydroanthraquinone. As solvent inert to halogenation there may be used carbon tetrachloride chloroform, nitrobenzene, chlorobenzene, or ethylene chloride. The halogenation may be effected at 0 DEG C. or below. The dihalo compound may be isolated and then redissolved in sulphuric acid for the nitration or it may be transferred directly by extraction from the organic solvent with the acid. Nitration occurs in the 5- and 6-positions. The nitrated product may be isolated by drowning in water and filtering the product, or the nitration mixture may be extracted with nitrobenzene and the extract may be used directly for the dehydrohalogenation. If the nitrated product is isolated it may be separated into the individual isomers by recrystallisation or other procedures. The 5-and 6 - nitro - 2, 3 - dichloro - 1, 2, 3, 4 - tetrahydroanthraquinones, and the corresponding dibromo compounds may thus be isolated. For the dehydrohalogenation step the caustic alkali used may be an alkali or alkaline earth metal hydroxide, preferably caustic soda or potash, and the temperature may be about 50 DEG C. If the nitro isomers are separated before dehalogenation the product is the 1- or the 2-nitro-anthraquinone, but if a mixture of the nitro isomers is used, separation after dehydrohalogenation may be effected by crystallisation or by extraction with sulphuric acid followed by dilution of the solution and fractional separation. The 1,4,4a,9a-tetrahydroanthraquinones used as starting materials may be obtained by reacting dienes with naphthoquinone. Specified dienes are butadiene and the 2-chloro-3-methyl-, 2,3-dimethoxy-, 2,3-dimethyl, 1-phenyl-, 1,4-diphenyl-, 2-chloro, 2-methyl-, 2-butyl-, 2-heptyl-, 2-phenyl-, 2-acetoxy-, 2-ethoxy-, and 2-bromoderivatives of butadiene, and 3-chloro-1,3-pentadiene, -hexadiene, and -octadiene, and cyclopentadiene. Specification 873,874 and U.S.A. Specification 2,642,445 are referred to.
FR785511A 1958-02-06 1959-02-02 Process for preparing mononitroanthraquinones Expired FR1224885A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US896911XA 1958-02-06 1958-02-06

Publications (1)

Publication Number Publication Date
FR1224885A true FR1224885A (en) 1960-06-28

Family

ID=22219071

Family Applications (1)

Application Number Title Priority Date Filing Date
FR785511A Expired FR1224885A (en) 1958-02-06 1959-02-02 Process for preparing mononitroanthraquinones

Country Status (3)

Country Link
DE (1) DE1101384B (en)
FR (1) FR1224885A (en)
GB (1) GB896911A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4176125A (en) * 1977-11-17 1979-11-27 Kawasaki Kasei Chemicals Ltd. Process for producing 1,4-dihydroanthraquinone
EP0010469A1 (en) * 1978-10-17 1980-04-30 P C U K Produits Chimiques Ugine Kuhlmann Process for preparing 5- and 6-nitro-1,2,3,4-tetrahydro-anthraquinone derivatives from 1,2,3,4-tetrahydro-anthracene-9,10-diol
EP0010470A1 (en) * 1978-10-17 1980-04-30 P C U K Produits Chimiques Ugine Kuhlmann Process for preparing 5- and 6-nitro-1,2,3,4-tetrahydro-anthraquinone derivatives from 1,2,3,4,4a,9a-hexahydro-anthracene-9,10-dione
FR2446807A1 (en) * 1979-01-19 1980-08-14 Ugine Kuhlmann NEW PROCESS FOR THE PREPARATION OF MONONITRO-TETRAHYDRO-1,2,3,4 ANTHRAQUINONES

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2751662C2 (en) * 1977-11-18 1985-10-24 Kawasaki Kasei Chemicals Ltd., Tokio/Tokyo Process for the preparation of 1,4-dihydroanthraquinones

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2642445A (en) * 1951-06-07 1953-06-16 American Cyanamid Co Halogen addition products of 1, 4-dihydroanthraquinone

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4176125A (en) * 1977-11-17 1979-11-27 Kawasaki Kasei Chemicals Ltd. Process for producing 1,4-dihydroanthraquinone
EP0010469A1 (en) * 1978-10-17 1980-04-30 P C U K Produits Chimiques Ugine Kuhlmann Process for preparing 5- and 6-nitro-1,2,3,4-tetrahydro-anthraquinone derivatives from 1,2,3,4-tetrahydro-anthracene-9,10-diol
EP0010470A1 (en) * 1978-10-17 1980-04-30 P C U K Produits Chimiques Ugine Kuhlmann Process for preparing 5- and 6-nitro-1,2,3,4-tetrahydro-anthraquinone derivatives from 1,2,3,4,4a,9a-hexahydro-anthracene-9,10-dione
FR2439180A1 (en) * 1978-10-17 1980-05-16 Ugine Kuhlmann PROCESS FOR THE PREPARATION OF NITRO-5 AND 6 DERIVATIVES OF TETRAHYDRO-1,2,3,4 ANTHRAQUINONE FROM HEXAHYDRO-1,2,3,4,4A, 9A ANTHRACENE-DIONE-9,10
FR2439179A1 (en) * 1978-10-17 1980-05-16 Ugine Kuhlmann PROCESS FOR THE PREPARATION OF NITRO-5 AND 6 DERIVATIVES OF TETRAHYDRO-1,2,3,4 ANTHRAQUINONE FROM TETRAHYDRO-1,2,3,4 ANTHRACENE-DIOL-9,10
FR2446807A1 (en) * 1979-01-19 1980-08-14 Ugine Kuhlmann NEW PROCESS FOR THE PREPARATION OF MONONITRO-TETRAHYDRO-1,2,3,4 ANTHRAQUINONES
EP0014602A1 (en) * 1979-01-19 1980-08-20 P C U K Produits Chimiques Ugine Kuhlmann Process for preparing mononitro-1,2,3,4-tetrahydro anthraquinones

Also Published As

Publication number Publication date
DE1101384B (en) 1961-03-09
GB896911A (en) 1962-05-23

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