GB508708A - Improvements in the manufacture and production of anthraquinone derivatives - Google Patents
Improvements in the manufacture and production of anthraquinone derivativesInfo
- Publication number
- GB508708A GB508708A GB134838A GB134838A GB508708A GB 508708 A GB508708 A GB 508708A GB 134838 A GB134838 A GB 134838A GB 134838 A GB134838 A GB 134838A GB 508708 A GB508708 A GB 508708A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aminoanthraquinone
- give
- aldehyde
- reacted
- acid
- 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
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
- C09B1/22—Dyes with unsubstituted amino groups
- C09B1/24—Dyes with unsubstituted amino groups sulfonated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
508,708. Dyes. JOHNSON, G. W. (I. G. Farbenindustrie Akt.-Ges.) Jan. 14, 1938, No. 1348. [Class 2 (iii)] 1.2-Pyridino- and 1.2-pyridono-anthraquinones and anthraquinone-acridines . are made' by 'reacting aminoanthraquinone-o-aldehydes in sulphuric or phosphoric acid with ketones containing a methylene group adjacent to the carbonyl group, with free or esterified malonic or cyanacetic acid or with one of the following: resorcinol, phloroglucinol, and alpha- or #-naphthol, 2.6- and 2.7-dihydroxynaphthalene, aminohydroxynaphthalenes, hydroxynaphthalene carboxylic acids and sulphonic acids, hydroxy anthracenes, hydroxyphenanthrenes, hydroxyazaphenanthrenes, hydroxythionaphthenes. Ketones specified are acetone, methyl ethyl ketone, acetyl acetone, acetophenone and its derivatives substituted in the aryl radical, methyl naphthyl ketones, desoxybenzoin, acetylanthracenes, acetylphenanthrenes cyclohexanonebarbituric acid, 2.5-diketopipÚrazines, hydantoines, naphthindandiones and naphthalene di-indandiones. In examples : (i.) l.aminoanthraquinone-2-aldehyde is reacted in concentrated sulphuric acid with #-naphthol to give anthraquinone- 1(N).2.2<1>(N). 1<1>-naphthacridine, which may be oxidized with chromic acid to give a substance dyeing cotton red shades; alpha-naphthol may replace the #-naphthol, and 2:6- or 2.7-dihydroxynaphthalene may react with one or two molecular proportions of 1-aminoanthraquinone-2-aldehyde ; 2-aminoanthraquinone-3-aldehyde may be reacted with #-naphthol; ,(2) 1-aminoanthraquinone-2-aldehyde is reacted with 2-hydroxynaphthalene-3 (or 5 or 6)-carboxylic acid to give anthraquinone-1(N).2.2<1>(N).1<1>-naphthacridine-31 (or 51 or 6<1>)-carboxylic acid ; (3) 1- aminoanthraquinone-2-aldehyde is reacted with 2-amino-7-naphthol in sulphuric acid to give anthraquinone-1(N).2.2<1>(N).1<1>. 7<1>-aminonaphthacridine; 1 amino-7-naphthol or 1-amino-3- naphthol may also be used; (4) 1 aminoanthraquinone-2-aldehyde is reacted with 2- hydroxyanthracene to give anthraquinone- 1(N)2.2<1>(N).1<1>-anthracene acridine, which maybe oxidized with chromic acid to give a yellowred dyestuff for cotton ; (5) 1-aminoanthraquinone.-2-aldehyde is reacted with #-naphthol in phosphoric acid to give the same product as in (1) ; (6) I-aminoanthraquinone-2-aldehyde is reacted with .barbituric acid to give anthraquinone-1(N).2.2<1>(N).1<1>-3<1>.5<1>-diaza-4<1>.6<1> dihydroxybenzacridine, which may be converted to, a dichlor derivative by reaction with phosphorus pentachloride; the barbituric acid may be replaced by 2.5-diketopiperazine, hydantoin or 1-phenylhydantoin (7) phloroglucinol is reacted with one, two, or three molecular proportions of 1-aminoanthraquinone- 2-aldehyde to give violet dyes for cotton; resorcinol may also be used; (8) 1-aminoanthraquinone-2-adehyde is reacted with perinaphthindandione or naphthalene-1.8.4.5-diindandione; (9) 1-aminoanthraquinone-2-aldehyde is reacted with acetophenone to give Py. 2-phenyl-1(N)-2-pyridinoanthraquinone ; the acetophenone may be replaced by p-amino-, p-methoxy-, p-methyl-, or m-nitro-acetophenone; (10) 1-aminoanthraquinone-2-aldehyde is reacted with 2- or 1-acetylnaphthatene to give Py.2-naphthyl-(2<1> or 1<1>)-1(N).2-pyridinoanthraquinone; (11) 1-aminoanthraquinone- 2,-aldehyde is reacted with 2-acetylanthracene to give Py.2-anthracyl-(2<1>)-1(N).2-pyridnoanthraquinone, which may be oxidized with chromic acid to give Py.2-anthraquinonyl- (2<1>)-1(N).2-pyridinoanthraquinone ; (12) 1- aminoanthraquinone-2-aldehyde is reacted with malonic acid or its esters to give anthraquinone- 1(N).2-pyridono-Py.3-carboxylic acid or with cyanacetic acid or its esters to give an anthraquinone-1(N).2-pyridono derivative.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB134838A GB508708A (en) | 1938-01-14 | 1938-01-14 | Improvements in the manufacture and production of anthraquinone derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB134838A GB508708A (en) | 1938-01-14 | 1938-01-14 | Improvements in the manufacture and production of anthraquinone derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB508708A true GB508708A (en) | 1939-07-05 |
Family
ID=9720431
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB134838A Expired GB508708A (en) | 1938-01-14 | 1938-01-14 | Improvements in the manufacture and production of anthraquinone derivatives |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB508708A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115650913A (en) * | 2022-10-12 | 2023-01-31 | 北京中医药大学 | Quinoid quinoline compound and preparation method and application thereof |
-
1938
- 1938-01-14 GB GB134838A patent/GB508708A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115650913A (en) * | 2022-10-12 | 2023-01-31 | 北京中医药大学 | Quinoid quinoline compound and preparation method and application thereof |
CN115650913B (en) * | 2022-10-12 | 2024-03-01 | 北京中医药大学 | Quinone quinoline compound and preparation method and application thereof |
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