GB492697A - Improvements in or relating to the manufacture of anthraquinone derivatives - Google Patents

Improvements in or relating to the manufacture of anthraquinone derivatives

Info

Publication number
GB492697A
GB492697A GB8919/37A GB891937A GB492697A GB 492697 A GB492697 A GB 492697A GB 8919/37 A GB8919/37 A GB 8919/37A GB 891937 A GB891937 A GB 891937A GB 492697 A GB492697 A GB 492697A
Authority
GB
United Kingdom
Prior art keywords
give
benzylamino
anthraquinone
dihydroxyanthraquinone
diaminoanthraquinone
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
GB8919/37A
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Publication of GB492697A publication Critical patent/GB492697A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups

Abstract

Aralkylaminoanthraquinones are obtained by reacting a nitro- or amino-anthraquinone, which may carry additional substituents, with an aralkylalcohol at an elevated temperature. Additional substituents specified are halogen, alkyl, hydroxy, alkoxy, nitro or amino groups. The reaction may be effected in an inert solvent such as nitrobenzene or o-dichlorbenzene, and at temperatures ranging from 100 DEG C. to the reflux temperature of the mass or approximately 200 DEG C. When a nitroanthraquinone is used, the presence of alkali is desirable. Monobenzylation of polyaminoanthraquinones may be effected by using an amount of benzyl alcohol only slightly in excess of the theoretical and preferably in a solvent. In examples, the following compounds are reacted with benzyl alcohol: (1) 1.8-diaminoanthraquinone to give 1.8-di-(benzylamino)anthraquinone; (2) 1.4.5.8-tetraaminoanthraquinone to give 1.5-di-(benzylamino) - 4.8 - diaminoanthraquinone (fast blue shades on cellulose acetate); (3) 1.8-diaminoanthraquinone - 4.5 - dihydroxyanthraquinone to give 1.8-di(benzylamino)-4.5-di-hydroxyanthraquinone; (4) 1-amino-2-bromo-4 - toluidoanthraquinone to give 1 - benzylamino - 2 - bromo - 4 - toluidoanthraquinone; (5) 1.8 - dimethoxy - 4.5 - diaminoanthraquinone to give 1.8-dimethoxy-4.5-di(benzylamino))- anthraquinone; (6) 1-nitro-2-methylanthraquinone (in presence of sodium carbonate) to give 1-benzylamino-2-methylanthraquinone (fast orange shades on cellulose acetate); (7) 1 - nitroanthraquinone (with sodium carbonate) to give 1-benzylaminoanthraquinone (red shades); (8) 1.8-diamino-4.5-dihydroxyanthraquinone to give 1-benzylamino-8-amino-4.5 - dihydroxyanthraquinone (reddish blue); (9) 1.8 - dihydroxy - 4.5 - dinitroanthraquinone (with sodium carbonate) to give 1.8-dihydroxy - 4 - benzylamino - 5 - nitroanthraquinone. Also in examples, 1.8 - diamino-4.5 - dihydroxyanthraquinone is reacted with b -phenyl ethyl alcohol to give 1.8-di-(b -phenyl ethylamino) - 4.5 - dihydroxy - anthraquinone. Other alkali metal carbonates or bicarbonates may replace sodium carbonate, and other aralkyl alcohols, such as b -phenyl ethyl alcohol, g -phenyl n-propyl alcohol, or m-nitrobenzyl alcohol may replace benzyl alcohol.
GB8919/37A 1936-03-25 1937-03-25 Improvements in or relating to the manufacture of anthraquinone derivatives Expired GB492697A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US492697XA 1936-03-25 1936-03-25

Publications (1)

Publication Number Publication Date
GB492697A true GB492697A (en) 1938-09-26

Family

ID=21958945

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8919/37A Expired GB492697A (en) 1936-03-25 1937-03-25 Improvements in or relating to the manufacture of anthraquinone derivatives

Country Status (1)

Country Link
GB (1) GB492697A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2726251A (en) * 1951-08-17 1955-12-06 Eastman Kodak Co 1, 8-dihydroxy-5-nitro-4-anilinoanthra-quinone compounds
US2777863A (en) * 1950-11-29 1957-01-15 Eastman Kodak Co 1, 5-dihydroxy-8-nitro-4-aminoanthraquinone compounds

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2777863A (en) * 1950-11-29 1957-01-15 Eastman Kodak Co 1, 5-dihydroxy-8-nitro-4-aminoanthraquinone compounds
US2726251A (en) * 1951-08-17 1955-12-06 Eastman Kodak Co 1, 8-dihydroxy-5-nitro-4-anilinoanthra-quinone compounds

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