CN106008239A - Production method of solvent blue 35 - Google Patents
Production method of solvent blue 35 Download PDFInfo
- Publication number
- CN106008239A CN106008239A CN201610341367.9A CN201610341367A CN106008239A CN 106008239 A CN106008239 A CN 106008239A CN 201610341367 A CN201610341367 A CN 201610341367A CN 106008239 A CN106008239 A CN 106008239A
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- China
- Prior art keywords
- solvent blue
- production method
- butylamine
- reaction
- dihydroxyanthraquinone
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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
- 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
- C09B1/285—Dyes with no other substituents than the amino groups
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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 a production method of solvent blue 35, and belongs to the field of chemical engineering materials. The production method comprises the concrete production and operation steps of at normal temperature, sequentially adding 1, 4-dihydroxy anthraquinone, n-butylamine, aromatic acids and water into a reaction kettle provided with a stirring and backflow device; performing stirring heating to 75 to 85 DEG C; performing heat insulation reaction for 2 to 4 hours; after the reaction is completed, cooling the materials to be below 40 DEG C; performing filtering, hot water washing, drying and discharging to obtain a solvent blue 35 product. The 1, 4-dihydroxy anthraquinone and the n-butylamine are used as the raw materials; aromatic acids are used as catalysts; reaction is taken in a water phase; sodium hydrosulfite, sodium hudroxide and 1, 4-dihydroxy anthraquinone leuco bodies are not used; meanwhile, the consumption of the n-butylamine is also reduced. The production method has the advantages that the production flow process is short; the operation is simple; the cost is low; meanwhile, the product quality is good; the yield is high.
Description
Technical field
The invention belongs to chemical material field, be specifically related to the production method of a kind of solvent blue 35.
Background technology
Solvent blue 35, chemical entitled Isosorbide-5-Nitrae-two (1-butylamine base) anthraquinone, call solvent blue 2N,
It is the solvent dye of a kind of function admirable, is primarily adapted for use in ABS, PC, HIPS, PMMS etc.
The coloring of various kinds of resin is it can also be used to the dope dyeing of polyster fibre.Solvent blue 35 molecular formula
For C22H26N2O2, molecular weight is 350.46, and structural formula is:
Existing main production process is with Isosorbide-5-Nitrae-dihydroxyanthraquinone as raw material, reduces with sodium hydrosulfite
Agent, n-butylamine is that raw material also serves as solvent, and in aqueous alkali, reaction prepares, and reacts mistake after terminating
Filter, washes away unreacted n-butylamine and tar with hot water, dries to obtain finished product, during the method reaction
Between long, n-butylamine consume height, by-product and the tar of generation are higher, alkalescence sulfur-containing waste water many,
Yield is low, and only about 75%.
Another also have a kind of solvent method, as State Intellectual Property Office announce in June, 2015 by river
Su Daobo Chemical Co., Ltd. declares, Application No. 201310713954.2, and title is
The technical scheme that the patent of invention of " a kind of method preparing solvent blue 35 " is used, i.e. with
Isosorbide-5-Nitrae-dihydroxyanthraquinone, Isosorbide-5-Nitrae-dihydroxyanthraquinone leuco compound and n-butylamine are raw material, anhydrous slufuric acid
Sodium is dehydrant, and acetic acid is catalyst, reacts in ethanol as solvent, and reaction terminates
After, steam ethanol, n-butylamine mixed solvent, add aqueous alkali isolation, filter, wash, dry
Finished product, but in this technical scheme, technological process is long, alkalescence sulfur-containing waste water is many, the ethanol of recovery,
N-butylamine mixed solution dehydration difficulty, proportioning is wayward, it is difficult to apply mechanically, containing a large amount of in waste water
Ethanol and butylamine, COD is the highest, it is difficult to biochemical treatment.
Summary of the invention
It is an object of the invention to provide the production method of a kind of solvent blue 35, with Isosorbide-5-Nitrae-dihydroxy
Base anthraquinone, n-butylamine are raw material, with aromatic acid as catalyst, react, do not use in aqueous phase
Sodium hydrosulfite, Caustic soda and Isosorbide-5-Nitrae-dihydroxyanthraquinone leuco compound, decrease the consumption of n-butylamine simultaneously,
To solve above-mentioned the problems of the prior art.
For achieving the above object, the present invention is by the following technical solutions:
The production method of a kind of solvent blue 35 in the present invention, its concrete production operation method is: often
Under temperature, successively Isosorbide-5-Nitrae-dihydroxyanthraquinone, n-butylamine, aromatic acid and water are joined equipped with stirring
And in the reactor of reflux, stirring heats up as 75～85 DEG C, insulation reaction 2～4h, instead
Should be cooled to after terminating less than 40 DEG C carry out filtering, hot wash (wash water recycling),
Dry discharging, obtain solvent blue 35 product.
Preferably, described Isosorbide-5-Nitrae-dihydroxyanthraquinone and n-butylamine mass ratio be 1:(1.43～
1.71)。
Preferably, described Isosorbide-5-Nitrae-dihydroxyanthraquinone and water quality are than for 1:(3.33～5.71).
Preferably, described aromatic acid quality is the 1.43% of Isosorbide-5-Nitrae-dihydroxyanthraquinone quality.
Preferably, the wash water in described hot wash recycles.
The beneficial effects of the present invention is:
(1) not using sodium hydrosulfite and Caustic soda, the alkaline waste water without sulfur-bearing pollutes；
(2) aromatic acid is catalyst, and the response time is 2h, and normal process is 5h, produces effect
Rate is high；
(3) not using Isosorbide-5-Nitrae-dihydroxyanthraquinone leuco compound is raw material, and cost of material is low；
(4) not using organic solvent, post processing is simple, and low cost, production operation is easier；
(5) n-butylamine consumption is only normal process n-butylamine consumption 49.3～58.9% (quality hundred
Proportion by subtraction), greatly reduce unreacted n-butylamine cost recovery；
(6) reaction yield is high, reaches more than 85%, far above the yield of normal process 75%.
Detailed description of the invention
Being described principle and the feature of the present invention in conjunction with example in detail below, example is only
For explaining the present invention, it is not intended to limit the scope of the present invention.
Chemical reaction of the present invention is:
The production method of a kind of solvent blue 35 in the present invention, concrete production operation step is: often
Under temperature, successively Isosorbide-5-Nitrae-dihydroxyanthraquinone, n-butylamine, aromatic acid and water are joined equipped with stirring
Mix and in the reactor of reflux, be heated with stirring to 75～85 DEG C, insulation reaction 2～4h,
Wherein, Isosorbide-5-Nitrae-dihydroxyanthraquinone and n-butylamine mass ratio are 1:(1.43～1.71), Isosorbide-5-Nitrae-dihydroxy
Anthraquinone and water quality are than for 1:(3.33～5.71), described aromatic acid quality is Isosorbide-5-Nitrae-dihydroxy
The 1.43% of base anthraquinone quality.Reaction be cooled to after terminating less than 40 DEG C carry out filtering, hot water wash
Wash (wash water recycling), dry discharging, obtain solvent blue 35 product.
Embodiment 1
At a 500ml four-hole boiling flask equipped with motor stirrer, thermometer and reflux condenser
In, addition 35g1,4-dihydroxyanthraquinone, 50g n-butylamine, 200g water, 0.5g aromatic acid,
Being heated with stirring to 85 DEG C, insulation reaction 2h, reaction is cooled to less than 40 DEG C after terminating and takes out
Filter, and with hot water, filter cake is washed three times, obtain 44.1g solvent blue 35 product, content after drying
98.4%, yield 86.5%.
Embodiment 2
At a 500ml four-hole boiling flask equipped with motor stirrer, thermometer and reflux condenser
In, addition 35g1,4-dihydroxyanthraquinone, 55g n-butylamine, 200g water, 0.5g aromatic acid,
Being heated with stirring to 80 DEG C, insulation reaction 2h, reaction is cooled to less than 40 DEG C after terminating and takes out
Filter, and with hot water, filter cake is washed three times, obtain 43.5g solvent blue 35 product, content after drying
98.6%, yield 85.3%.
Embodiment 3
At a 500ml four-hole boiling flask equipped with motor stirrer, thermometer and reflux condenser
In, addition 35g1,4-dihydroxyanthraquinone, 60g n-butylamine, 200g water, 0.5g aromatic acid,
Being heated with stirring to 85 DEG C, insulation reaction 2h, reaction is cooled to less than 40 DEG C after terminating and takes out
Filter, and washes filter cake three times with hot water, after drying 45g solvent blue 35 product, content 98.2%,
Yield 88.2%.
Embodiment 4
At a 500ml four-hole boiling flask equipped with motor stirrer, thermometer and reflux condenser
In, addition 35g1,4-dihydroxyanthraquinone, 50g n-butylamine, 200g water, 0.5g aromatic acid,
Being heated with stirring to 75 DEG C, insulation reaction 4h, reaction is cooled to less than 40 DEG C after terminating and takes out
Filter, and with hot water, filter cake is washed three times, obtain 44.5g solvent blue 35 product, content after drying
99.2%, yield 87.3%.
Comparative example
At a 500ml four-hole boiling flask equipped with motor stirrer, thermometer and reflux condenser
In, addition 20g1,4-dihydroxyanthraquinone, 58g n-butylamine, 8g liquid caustic soda, 4.4g sodium hydrosulfite,
50g water, is heated with stirring to 85～88 DEG C, insulation reaction 5h, and reaction is cooled to 40 DEG C after terminating
Hereinafter carry out sucking filtration, and with hot water, filter cake is washed three times, after drying, obtain 22.5g solvent blue 35
Product, content 98.1%.
Skilled person will appreciate that of the industry, the present invention is not restricted to the described embodiments, on
State the principle that the present invention is simply described described in embodiment and description, without departing from the present invention
On the premise of spirit and scope, the present invention also has various changes and modifications, and these change and change
Enter to both fall within scope of the claimed invention.Claimed scope is by appended power
Profit claim and equivalent thereof define.
Claims (5)
1. the production method of a solvent blue 35, it is characterised in that its concrete production operation walks
Suddenly it is: under room temperature successively Isosorbide-5-Nitrae-dihydroxyanthraquinone, n-butylamine, aromatic acid and water to be added
In the reactor equipped with stirring and reflux, being heated with stirring to 75～85 DEG C, insulation is anti-
Answering 2～4h, reaction is cooled to less than 40 DEG C and carries out filtering, hot wash, dries out after terminating
Material, obtains solvent blue 35 product.
The production method of a kind of solvent blue 35 the most according to claim 1, its feature exists
In, described Isosorbide-5-Nitrae-dihydroxyanthraquinone and n-butylamine mass ratio are 1:(1.43～1.71).
The production method of a kind of solvent blue 35 the most according to claim 1, its feature exists
In, described Isosorbide-5-Nitrae-dihydroxyanthraquinone and water quality than for 1:(3.33～5.71).
The production method of a kind of solvent blue 35 the most according to claim 1, its feature exists
In, described aromatic acid quality is the 1.43% of Isosorbide-5-Nitrae-dihydroxyanthraquinone quality.
The production method of a kind of solvent blue 35 the most according to claim 1, its feature exists
In, the wash water in described hot wash recycles.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610341367.9A CN106008239A (en) | 2016-05-20 | 2016-05-20 | Production method of solvent blue 35 |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610341367.9A CN106008239A (en) | 2016-05-20 | 2016-05-20 | Production method of solvent blue 35 |
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| CN106008239A true CN106008239A (en) | 2016-10-12 |
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| CN201610341367.9A Pending CN106008239A (en) | 2016-05-20 | 2016-05-20 | Production method of solvent blue 35 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112176738A (en) * | 2020-11-04 | 2021-01-05 | 季德虎 | Plastic colorant 2N blue and preparation method thereof |
| CN112521767A (en) * | 2020-12-22 | 2021-03-19 | 安徽清科瑞洁新材料有限公司 | Preparation method of low-pollution diarylamine anthraquinone solvent blue 35 dye |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2727045A (en) * | 1952-12-13 | 1955-12-13 | American Cyanamid Co | Preparation of alkylaminoanthraquinones |
| DE2209984A1 (en) * | 1972-03-02 | 1973-09-06 | Basf Ag | N,n'-disubstd 1,4-diaminoanthraquinone prepn - in (poly) glycol (monoalkyl ether) as solvent |
| FR2694564A1 (en) * | 1992-08-07 | 1994-02-11 | Sepia Chim Sa | Prepn. of concn. colouring solns. based on 1,4-dialkyl amino-anthraquinone - useful in the colour identification of petroleum prods. |
| CN102584596A (en) * | 2012-01-17 | 2012-07-18 | 宜兴市聚金信化工有限公司 | Method for preparing age inhibitor 3100 |
| CN103319379A (en) * | 2013-07-02 | 2013-09-25 | 湘潭市开元化学有限公司 | Process for synthesizing anthraquinone compound |
-
2016
- 2016-05-20 CN CN201610341367.9A patent/CN106008239A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2727045A (en) * | 1952-12-13 | 1955-12-13 | American Cyanamid Co | Preparation of alkylaminoanthraquinones |
| DE2209984A1 (en) * | 1972-03-02 | 1973-09-06 | Basf Ag | N,n'-disubstd 1,4-diaminoanthraquinone prepn - in (poly) glycol (monoalkyl ether) as solvent |
| FR2694564A1 (en) * | 1992-08-07 | 1994-02-11 | Sepia Chim Sa | Prepn. of concn. colouring solns. based on 1,4-dialkyl amino-anthraquinone - useful in the colour identification of petroleum prods. |
| CN102584596A (en) * | 2012-01-17 | 2012-07-18 | 宜兴市聚金信化工有限公司 | Method for preparing age inhibitor 3100 |
| CN103319379A (en) * | 2013-07-02 | 2013-09-25 | 湘潭市开元化学有限公司 | Process for synthesizing anthraquinone compound |
Non-Patent Citations (3)
| Title |
|---|
| KIKUCHI, MASASHI等: "Direct alkylamination of 1,4-dihydroxyanthraquinone in the presence of sodium dithionite", 《CHEMISTRY LETTERS》 * |
| KIKUCHI, MASASHI等: "The structure determination of leucoanthraquinones by proton and carbon-13 nuclear magnetic resonance spectroscopy", 《DYES AND PIGMENTS》 * |
| PETERS, ARNOLD T.等: "Intermediates and dyes. IV. Condensation of 2,3-thianaphthenedicarboxylic anhydride with hydrocarbons and phenols", 《JOURNAL OF THE CHEMICAL SOCIETY》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112176738A (en) * | 2020-11-04 | 2021-01-05 | 季德虎 | Plastic colorant 2N blue and preparation method thereof |
| CN112521767A (en) * | 2020-12-22 | 2021-03-19 | 安徽清科瑞洁新材料有限公司 | Preparation method of low-pollution diarylamine anthraquinone solvent blue 35 dye |
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Application publication date: 20161012 |