CN108947857A - A kind of process for refining of 1,4- diamino -2,3- dichloroanthraquinone - Google Patents
A kind of process for refining of 1,4- diamino -2,3- dichloroanthraquinone Download PDFInfo
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- CN108947857A CN108947857A CN201810800315.2A CN201810800315A CN108947857A CN 108947857 A CN108947857 A CN 108947857A CN 201810800315 A CN201810800315 A CN 201810800315A CN 108947857 A CN108947857 A CN 108947857A
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- Prior art keywords
- diamino
- nitrae
- isosorbide
- dichloroanthraquinone
- refining
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention discloses one kind 1, 4- diamino -2, the process for refining of 3- dichloroanthraquinone, belong to organic synthesis field, include the following steps: in a reservoir, it is added 1, 4- diamino-anthraquinone leuco compound, using anhydrous nitrobenzene or o-dichlorohenzene as solvent, azodiisobutyronitrile makees catalyst, control 35 ~ 40 DEG C of dropwise addition chlorosulfuric acids of temperature, it is added dropwise, 50 ± 5 DEG C of heat preservations 5 hours or more, it pours into 350 ~ 450 parts of water, surfactant is added, it is neutralized with soda ash to neutrality, steam distillation solvent, heat filtering again, 80 DEG C of hot water washings are colourless to wash water and pH value is close neutral, discharging drying obtains 1, 4- diamino -2, 3- dichloroanthraquinone.The internal standard content of 1,4- diamino -2,3- dichloroanthraquinone product after present invention purification can improve 2.5% ~ 3.5%.
Description
Technical field
The present invention relates to a kind of Isosorbide-5-Nitrae-diamino -2,3- dichloroanthraquinone improvement techniques, belong to technical field of organic synthesis.
Background technique
Isosorbide-5-Nitrae-diamino base -2,3- dichloroanthraquinone is a kind of important disperse dyes, dyestuff title disperse violet 28, while
It is a kind of important dyestuff intermediate, can be used for dyestuff and disperse No. 26 purple synthesis, function admirable, the market demand is big, and prospect is wide
It is general.Isosorbide-5-Nitrae-diamino -2,3- dichloroanthraquinone synthesis technology is added in solvent nitrobenzene or dichloro-benzenes, chlorobenzene equal solvent
Chlorosulfuric acid is added dropwise in Isosorbide-5-Nitrae-diamino-anthraquinone leuco compound, also has been reported that Isosorbide-5-Nitrae-diamino-anthraquinone leuco compound leads to chlorine chlorine in a solvent
Change obtains, and is all finally product that filtration washing be precipitated in water phase by solvent distillation to obtain product, due to Isosorbide-5-Nitrae-diamino
Base anthraquinone leuco compound chemical content is all between 92 ~ 95%, and water phase leads to product Isosorbide-5-Nitrae-almost without how many impurity removal function
Diamino -2,3- dichloroanthraquinone real content is not high, mainly has a large amount of tar ingredients inside, although report Isosorbide-5-Nitrae-diamino
Base -2,3- dichloroanthraquinone chromatographic content has 96 ~ 99%, but internal standard content is not in fact high, generally 90 ~ 94%, due to content
It is not high, have an adverse effect to subsequent use.
Summary of the invention
The object of the present invention is to provide a kind of Isosorbide-5-Nitrae-diamino -2,3- dichloroanthraquinone process for refining, the technique is improved
The purity of 1,4- diamino -2,3- dichloroanthraquinone.
Realizing the technical solution of the object of the invention is: a kind of process for refining of Isosorbide-5-Nitrae-diamino -2,3- dichloroanthraquinone,
Include the following steps:
In a reservoir, Isosorbide-5-Nitrae-diamino-anthraquinone leuco compound, using anhydrous nitrobenzene or o-dichlorohenzene as solvent, two isobutyl of azo is added
Nitrile makees catalyst, controls 35 ~ 40 DEG C of dropwises addition chlorosulfuric acids of temperature, is added dropwise, and 50 ± 5 DEG C keep the temperature 5 hours or more, is poured into water,
Surfactant is added, is neutralized with soda ash to neutrality, steam distillation solvent, then heat filtering, 80 DEG C of hot water wash colourless to wash water
And pH value, close to neutrality, discharging drying obtains Isosorbide-5-Nitrae-diamino -2,3- dichloroanthraquinone.
Further, surfactant is in neopelex, sodium lignin sulfonate and methyl naphthalene sulfonic acid sodium
One or more of mixtures.
Further, surfactant additive amount is Isosorbide-5-Nitrae-diamino procrypsis weight 1% ~ 5 ‰.
The azodiisobutyronitrile being further added can provide free radical, there is catalytic action, be conducive to reaction and carry out completely,
Dosage is 1% ~ the 5 ‰ of 4- diamino procrypsis weight.
Compared with prior art, the invention has the advantages that Isosorbide-5-Nitrae-diamino -2,3- dichloroanthraquinone product after purification is interior
Mark content can improve 2.5% ~ 3.5%.
Specific embodiment
Embodiment 1
In 500 milliliters of four-hole boiling flasks, 400 grams of nitrobenzene are added, Isosorbide-5-Nitrae -60 grams of diamino-anthraquinone leuco compound (content is added with stirring
94.0%), 0.2 gram of azodiisobutyronitrile makees catalyst, and 35 ~ 40 degrees Celsius of 105 grams of chlorosulfuric acid of dropwise additions (content 92%) drip
Finish, is warming up to 60 DEG C and keeps the temperature 4 hours, be slowly transferred in the flask for being pre-loaded with 1700 milliliters of water, sodium lignin sulfonate is added
0.5 gram of salt, with soda ash neutralization to neutrality, steam distillation nitrobenzene, distillation is finished, and cools to 80 degrees Celsius of filterings, is washed in close
Property, it discharges, drying, detection level.Drying obtains 71.4 grams of product, internal standard content 96.5%, chromatographic content 99.2%.
Embodiment 2
In 500 milliliters of four-hole boiling flasks, 500 grams of o-dichlorohenzene are added, Isosorbide-5-Nitrae -60 grams of diamino-anthraquinone leuco compound is added with stirring and (contains
93.2%), 0.2 gram of azodiisobutyronitrile makees catalyst to amount, and 35 ~ 40 degrees Celsius of 102.5 grams of chlorosulfuric acid of dropwise additions (content 92%) are added dropwise
It finishes, is warming up to 60 DEG C and keeps the temperature 4 hours, be slowly transferred in the flask for being pre-loaded with 1800 milliliters of water, detergent alkylate is added
0.5 gram of sodium sulfonate, with soda ash neutralization to neutrality, steam distillation o-dichlorohenzene, distillation is finished, and cools to 80 degrees Celsius of filterings, water
Weakly acidic pH is washed, is discharged, drying, detection level.Drying obtains 70.2 grams of product, internal standard content 96.3%, chromatographic content 99.0%.
Claims (5)
1. a kind of Isosorbide-5-Nitrae-diamino -2,3- dichloroanthraquinone process for refining, which comprises the steps of:
In a reservoir, Isosorbide-5-Nitrae-diamino-anthraquinone leuco compound, using anhydrous nitrobenzene or o-dichlorohenzene as solvent, two isobutyl of azo is added
Nitrile makees catalyst, controls 35 ~ 40 DEG C of dropwises addition chlorosulfuric acids of temperature, is added dropwise, and 50 ± 5 DEG C keep the temperature 5 hours or more, pour into 350 ~
In 450 parts of water, surfactant is added, is neutralized with soda ash to neutrality, steam distillation solvent, then heat filtering, 80 DEG C of hot water washings
And pH value colourless to wash water obtains Isosorbide-5-Nitrae-diamino -2,3- dichloroanthraquinone close to neutrality, discharging drying.
2. process for refining as described in claim 1, which is characterized in that surfactant is neopelex, wooden
One or more of plain sodium sulfonate and methyl naphthalene sulfonic acid sodium mixture.
3. process for refining as claimed in claim 1 or 2, which is characterized in that surfactant additive amount is that Isosorbide-5-Nitrae-diamino is hidden
The 1% of colour solid quality ~ 5 ‰.
4. process for refining as described in claim 1, which is characterized in that dosage of azodiisobutyronitrile is 4- diamino leuco compound
The 1% of quality ~ 5 ‰.
5. process for refining as described in claim 1, which is characterized in that Isosorbide-5-Nitrae-diamino-anthraquinone leuco compound and chlorosulfuric acid mole
Than for 1:3.33 ~ 3 ~ 3.38.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810800315.2A CN108947857A (en) | 2018-07-20 | 2018-07-20 | A kind of process for refining of 1,4- diamino -2,3- dichloroanthraquinone |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810800315.2A CN108947857A (en) | 2018-07-20 | 2018-07-20 | A kind of process for refining of 1,4- diamino -2,3- dichloroanthraquinone |
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| CN201810800315.2A Withdrawn CN108947857A (en) | 2018-07-20 | 2018-07-20 | A kind of process for refining of 1,4- diamino -2,3- dichloroanthraquinone |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112111169A (en) * | 2020-09-17 | 2020-12-22 | 湖北彩德新材料科技有限公司 | Plastic colorant disperse violet 28 and preparation method thereof |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB271023A (en) * | 1926-01-11 | 1927-05-11 | British Dyestuffs Corp Ltd | The manufacture and production of anthraquinone intermediates |
| FR646130A (en) * | 1927-02-08 | 1928-11-07 | Ig Farbenindustrie Ag | Process for the preparation of aminoanthraquinones, their derivatives and substitution products starting from the corresponding leucoamino compounds |
| DE488684C (en) * | 1927-02-09 | 1930-01-03 | I G Farbenindustrie Akt Ges | Process for the preparation of aminoanthraquinones, their derivatives and substitution products |
| US4452742A (en) * | 1981-12-09 | 1984-06-05 | Bayer Aktiengesellschaft | Process for the preparation of 4,4'-diamino-1,1'-dianthrimides |
| US5102764A (en) * | 1989-12-15 | 1992-04-07 | Eastman Kodak Company | Styrene butylacrylate toner with magenta dye |
| CN102219704A (en) * | 2011-04-20 | 2011-10-19 | 江苏亚邦染料股份有限公司 | Improved method for synthesizing 1,4-diamino-2,3-dichloroanthraquinone |
| CN105693530A (en) * | 2014-11-27 | 2016-06-22 | 江苏华尔化工有限公司 | Synthesis method of 1,4-diamino-2,3-dichloro-dichloroanthraquinone |
-
2018
- 2018-07-20 CN CN201810800315.2A patent/CN108947857A/en not_active Withdrawn
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB271023A (en) * | 1926-01-11 | 1927-05-11 | British Dyestuffs Corp Ltd | The manufacture and production of anthraquinone intermediates |
| FR646130A (en) * | 1927-02-08 | 1928-11-07 | Ig Farbenindustrie Ag | Process for the preparation of aminoanthraquinones, their derivatives and substitution products starting from the corresponding leucoamino compounds |
| DE488684C (en) * | 1927-02-09 | 1930-01-03 | I G Farbenindustrie Akt Ges | Process for the preparation of aminoanthraquinones, their derivatives and substitution products |
| US4452742A (en) * | 1981-12-09 | 1984-06-05 | Bayer Aktiengesellschaft | Process for the preparation of 4,4'-diamino-1,1'-dianthrimides |
| US5102764A (en) * | 1989-12-15 | 1992-04-07 | Eastman Kodak Company | Styrene butylacrylate toner with magenta dye |
| CN102219704A (en) * | 2011-04-20 | 2011-10-19 | 江苏亚邦染料股份有限公司 | Improved method for synthesizing 1,4-diamino-2,3-dichloroanthraquinone |
| CN105693530A (en) * | 2014-11-27 | 2016-06-22 | 江苏华尔化工有限公司 | Synthesis method of 1,4-diamino-2,3-dichloro-dichloroanthraquinone |
Non-Patent Citations (1)
| Title |
|---|
| FREEMAN, H. S.等: "Purification procedures for synthetic dyes: part 1 -Dry column chromatography", 《DYES AND PIGMENTS》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112111169A (en) * | 2020-09-17 | 2020-12-22 | 湖北彩德新材料科技有限公司 | Plastic colorant disperse violet 28 and preparation method thereof |
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Application publication date: 20181207 |