US1895203A - Production of anthraquinone azines - Google Patents
Production of anthraquinone azines Download PDFInfo
- Publication number
- US1895203A US1895203A US501745A US50174530A US1895203A US 1895203 A US1895203 A US 1895203A US 501745 A US501745 A US 501745A US 50174530 A US50174530 A US 50174530A US 1895203 A US1895203 A US 1895203A
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- US
- United States
- Prior art keywords
- production
- azines
- anthraquinone
- parts
- melt
- 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 - Lifetime
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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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/44—Azines of the anthracene series
- C09B5/46—Para-diazines
- C09B5/48—Bis-anthraquinonediazines (indanthrone)
Definitions
- the present invention relates to improvements in the production of N-dihydro- 1.2.1.2-anthraquinoneazines.
- potassium formate potassium acetate, and the like, in the presence, if required, of an inert diluent, or to add alcoholates or phenolates, such as sodium butylate, sodium phenolate, and the like.
- salts of low fatty acids namel of formic, acetic or propionic acid
- salts of the latter kind comprise, for example, alkali metal salts of butyric acid (normal or iso-), valeric acid, stearic and palmitic acid.
- the caustic alkali melt may be carried out with an addition of oxidizing agents or also in the absence of such agents, and preferably with fused caustic potash-soda.
- Example 1 15 parts of dehydrated sodium acetate are stirred into 200 parts of a mixture, in molecular porportions, of caustic potash and soda at a temperature of about 200 Cl, 20 parts of soap being then added. Thereupon 75 parts of ,B-aminoanthraquinone are introduced, and the mixture is stirred at a tem- The I our hands.
- the potassium isobutyrate may be replaced by potassium butyrate which gives an equally good result.
- N-dihydro- 1.22.1-anthraquinoneazines which comprises subjecting a 2-aminoanthraquinone to the action of a caustic potash-soda melt in the presence of a salt of a low fatty acid in conjunction with a salt of a fatty acid containing at least 5 carbon atoms.
- N-dihydro- 1.22.1 anthraquinoneazine which comprises subjecting a 2-aminoanthraquinone to the action of a caustic alkali melt in the presence of a salt of a low fatty acid in conjunction with an alkali metal salt of a valeric acid.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Jan. 24, 1933 UNITED STATES PATENT OFFICE PAUL NAWIASKY AND LUDWIG EIFFLAENDER, OF LUDWIG-SHAFEN-ON TI-IE-RHINE,
GERMANY, ASSIGNORS TO GENERAL ANILINE WORKS, 1110., OF NEW YORK, N; Y
CORPORATION OF DELAWARE PRODUCTION OF ANTHRAQ'O'INONE AZINES No Drawing. Application filed December 11, 1930, Serial No. 501,745, and in Germany October 8, 1926.
The present invention relates to improvements in the production of N-dihydro- 1.2.1.2-anthraquinoneazines.
This application is a continuation-in-part of my copending application Ser. No. 229,258 for improvements in the production of N- dihydro-1.2.1.2j-anthraquinoneazines, filed October 27, 1927. V i
It is known that the valuable blue dyestufi N-dihydro-1.2.1.2-anthraquinoneazine can be obtained by the action of fused caustic alkali on 2-aminoanthraquinone, with or without the addition of oxidizing agents, the melt being poured into water and oxidized with air. In order to improve the yield, it has also been proposed to add to the melt, salts of low fatty acids, such for example as.
potassium formate, potassium acetate, and the like, in the presence, if required, of an inert diluent, or to add alcoholates or phenolates, such as sodium butylate, sodium phenolate, and the like. i
We have now found that still better yields of the said dyestufi' or of its derivatives when starting from substituted 2-amino-anthraquinone, may be obtained if salts of low fatty acids, namel of formic, acetic or propionic acid, are ad ed to the caustic alkali melt in conjunction with salts of fatty acids containing at least 4 carbon atoms. Salts of the latter kind comprise, for example, alkali metal salts of butyric acid (normal or iso-), valeric acid, stearic and palmitic acid.
According to the present invention the caustic alkali melt may be carried out with an addition of oxidizing agents or also in the absence of such agents, and preferably with fused caustic potash-soda.
The following examples will further illustrate the nature of the said invention, but the invention is not limited thereto. parts are by weight.
' Example 1 15 parts of dehydrated sodium acetate are stirred into 200 parts of a mixture, in molecular porportions, of caustic potash and soda at a temperature of about 200 Cl, 20 parts of soap being then added. Thereupon 75 parts of ,B-aminoanthraquinone are introduced, and the mixture is stirred at a tem- The I our hands.
perature of from 200 to 210 C. until the production of the dyestuff ceases'to increase.
The separation of the dyestuif is effected in the usual manner.
i Ewample 2 parts of dehydrated sodium acetate are. introduced into a melt of 2,000 parts of caustic potash-soda at a temperature of 250 G, 45 parts of potassium isobutyrate being then added and the mixture stirred until uniform distribution has taken place. The mixture is then cooled down to a temperature of 210 C. and 500 parts of ,B-aminoanthraquinone are introduced in such a way that the temperature does not rise above 230 C. The whole mixture is maintained at a temperature of 225 C. until the production of dyestuif ceases to increase and ,B-aminoanthraquino'ne can no longer be detected. The melt is then 70 treated in the usual way.
The potassium isobutyrate may be replaced by potassium butyrate which gives an equally good result.
What we claim is 1. The process of producing N-dihydro- 1.2.2.1-anthraquinoneazines, which comprises subjecting a 2-aminoanthraquinone to the action of a caustic alkali melt in the presence of a salt of a low fatty acid in conjunction with asalt of a fatty acid containing at 7 least- 5 carbon atoms. I
2. The process of producing N-dihydro- 1.22.1-anthraquinoneazines, which comprises subjecting a 2-aminoanthraquinone to the action of a caustic potash-soda melt in the presence of a salt of a low fatty acid in conjunction with a salt of a fatty acid containing at least 5 carbon atoms.
3. The process of producing N-dihydro- 1.22.1 anthraquinoneazine, which comprises subjecting a 2-aminoanthraquinone to the action of a caustic alkali melt in the presence of a salt of a low fatty acid in conjunction with an alkali metal salt of a valeric acid.
In testimony whereof we have hereunto set PAUL NAWIASKY.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1895203X | 1926-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1895203A true US1895203A (en) | 1933-01-24 |
Family
ID=7748098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US501745A Expired - Lifetime US1895203A (en) | 1926-10-08 | 1930-12-11 | Production of anthraquinone azines |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1895203A (en) |
-
1930
- 1930-12-11 US US501745A patent/US1895203A/en not_active Expired - Lifetime
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