CN86106303A - With the hydroxyl acetonitrile is the cyanidization agent synthesis of dispersive dyestuff contacning cyano - Google Patents
With the hydroxyl acetonitrile is the cyanidization agent synthesis of dispersive dyestuff contacning cyano Download PDFInfo
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- CN86106303A CN86106303A CN 86106303 CN86106303A CN86106303A CN 86106303 A CN86106303 A CN 86106303A CN 86106303 CN86106303 CN 86106303 CN 86106303 A CN86106303 A CN 86106303A CN 86106303 A CN86106303 A CN 86106303A
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- dyestuff
- cyanidization agent
- cyanidization
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Abstract
Finish the cyaniding substitution reaction with organic cyanide with phase transfer catalytic technology as cyanidization agent, reach the part cyaniding by control cyanidization agent consumption, thereby once obtain the composite dye be made up of two dyestuffs, this is a principal character of the present invention.
The present invention is that preceding dyestuff mixes mutually with cyanidization agent, acid binding agent, phase-transfer catalyst, and operation is easy, safety, technical process short, does not produce cupric, cyanide bearing waste solution simultaneously.In process of production equipment there is not particular requirement.
The used cyanidization agent of the present invention---hydroxyl acetonitrile is formaldehyde and the addition of hydrogenation cyanogen and prepare the easy steady quality of its production method.
Description
The invention belongs to fine chemistry industry dyestuff composite part
Patent description:
(1) general formula of azoic dyestuff involved in the present invention is:
D-A-N＝N-B
In the formula: A: aryl
B: coupling component
D: be positioned at azo-group adjacent cyano group
(2), be used as organic cyanidization agent with nitrile compound shown in the following general formula
G-CN
In the formula: G:H or
X:H, halogen atom
Y: a negative electricity group
R:H or alkyl, aryl
(3) dyestuff of preparation shown in (1), the copper catalyst consumption is 0.01-1.0mol/mol(copper catalyst/preceding dyestuff)
(4) use organic bases, weakly alkaline metal oxide or weakly alkaline inorganic salt and be used as acid binding agent.
(5) with quaternary ammonium salt, crown ether phase-transfer catalyst as this reaction.
Patents state:
The present invention relates to the preparation method of the azoic dyestuff of a cyano group of class azo-group ortho position existence.Can obtain such dyestuff according to this method.
There is the azoic dyestuff of cyano group in the ortho position of azo-group, can prepare by the halogen atom that cyano group replaces corresponding halogen dyestuff, and known method is that the applied metal prussiate is as cyanidization agent.And the present invention uses nonvirulent organic cyanide, carries out cyanogenation in the presence of acid binding agent.
The preparation of virtue halogen azoic dyestuff (preceding dyestuff) is carried out according to a conventional method.
Be converted into cyano group by halogen, along with chloro dyestuff, iodo dyestuff, bromo dyestuff, and more and more easy.If two halogens are positioned at the azo-group ortho position, then two halogens all may be converted into cyano group.
Particularly suitable cyanidization agent-organic cyanide of the present invention is the cyanalcohol of aldehydes or ketones.As: formaldehyde cyanalcohol (OHCH
2CN), propyl alcohol cyanogen (CH
3CH(OH) acetone cyanohydrin (CH CN),
3)
2C(OH) CN.Theirs is synthetic all very easy.
Copper catalyst can be monovalence copper or cupric compound, is preferably the monovalence copper compound, as cuprous chloride, cuprous bromide, cuprous cyanide.Its consumption is 0.1-1.0mol/mol.
Alkaline matter all can be acid binding agent, and organic bases, weakly alkaline metal oxide or weakly acidic inorganic acid salt all can be made acid binding agent, as: pyridine, ammonium acetate, Sodium phosphate dibasic, sodium acetate, yellow soda ash etc.
The medium of reaction is very big to the reaction influence.In organic solvent, react to be better than in water and react.Solvent can use separately also can mix with water and use.Solvent commonly used has: dimethyl formamide, chlorobenzene, methyl-phenoxide, oil of mirbane etc.Its consumption is 1-15 a times of preceding dyestuff weight.
Adding phase-transfer catalyst is one of characteristics of the present invention, and quaternary ammonium salt, crown ether etc. all can be used as phase-transfer catalyst, and its consumption is the 1.0-30% of preceding dyestuff weight.
Dyestuff involved in the present invention is a composite dye, and it is to be composited by two dye components, by the consumption of control cyanidization agent, can reach this purpose in reaction.
Chemical reaction that the present invention narrates is simple to operate, and it is by halogen dyestuff (preceding dyestuff) and cyanidization agent, acid binding agent, phase-transfer catalyst, copper catalyst, and Hybrid Heating is in 60-120 ℃ in reaction medium, and reaction proceeds to terminal point.Optimal reaction temperature depends on the structure of employed cyanidization agent, solvent, preceding dyestuff.After reaction is carried out, separate, and obtain the cyano-containing dyestuff by usual method.
The remarkable advantage of the inventive method is to use organic cyanide than using metal cyanides safety, and metal cyanides is poisonous, and generates the hydrogenation cyanogen of severe toxicity under the effect of acid rapidly.Because it is acid that waste water from dyestuff mostly is greatly, and make its dangerous increasing, and use organic cyanide not have this problem.
Normally used metal cyanides-cuprous cyanide makes to occur dyestuff copper content height and copper-containing wastewater problem in the production.Another advantage of the present invention is that copper content need not to remove process for copper at acceptability limit in the dyestuff, does not produce contained waste liquid.
Use metal cyanides can produce cyanide bearing waste solution simultaneously, if reduce in the waste liquid, cyanogen content then needs except that cyanogen process in the dyestuff.The present invention has then saved and has removed cyanogen process, does not contain cryanide ion in the waste liquid simultaneously.This also is another excellent place of the present invention.
The present invention chats and disperses blue S-RBL(DISPERSE BLUE S-RSL) its preparation method is as follows:
15 restrain preceding dyestuff, 150 gram methyl-phenoxides, and 0.43 gram cuprous bromide, the hydroxyl acetonitrile of 1.5 gram quaternary ammonium salts and stoichiometric quantity, the yellow soda ash mixing is warming up to 60-100 ℃, reacts 2-8 hour, and tlc analysis carries out steam distillation after reaching terminal point, and solvent is steamed.Dye suspension separates in water, washes to such an extent that disperse blue S-REL, and yield is 90%
In the formula: X:-CH
3-NO
2
B: coupling component
Annotate: the used hydroxyl acetonitrile of the present invention is its 40% aqueous solution.
Sum up:
In the presence of phase transfer catalyst, copper catalyst, acid binding agent, solvent, deposit the Dispers ozoic dyestuff of cyano group at the azo group ortho position with organic cyanide effect preparation by corresponding halogen dyestuff, its handling safety, easy, with short production cycle does not produce simultaneously that to contain the cyanogen contained waste liquid be a kind of comparatively desirable Process for the cyanation.
Claims (4)
1, make catalyzer with copper in halogen dyestuff (preceding dyestuff), using organic bases, weakly alkaline metal oxide or weakly alkaline inorganic salt is acid binding agent, is organic cyanidization agent with nonvirulent organic cyanide.Doing under the condition of phase-transfer catalyst with quaternary ammonium salt, crown ether.Temperature is between 60～120 ℃, to prepare the composite dye of being made up of two dyestuffs.
2, composite dye as claimed in claim 1 is characterized in that: can once obtain in reaction.
3, it is characterized in that as claim 1,2 described composite dyes: compound ratio can be with 0～100%.
4, composite dye as claimed in claim 1 is characterized in that: used cyanidization agent is nonvirulent organic cyanide-hydroxyl acetonitrile.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 86106303 CN86106303A (en) | 1986-09-20 | 1986-09-20 | With the hydroxyl acetonitrile is the cyanidization agent synthesis of dispersive dyestuff contacning cyano |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 86106303 CN86106303A (en) | 1986-09-20 | 1986-09-20 | With the hydroxyl acetonitrile is the cyanidization agent synthesis of dispersive dyestuff contacning cyano |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN86106303A true CN86106303A (en) | 1988-03-30 |
Family
ID=4803145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 86106303 Pending CN86106303A (en) | 1986-09-20 | 1986-09-20 | With the hydroxyl acetonitrile is the cyanidization agent synthesis of dispersive dyestuff contacning cyano |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN86106303A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103627201A (en) * | 2013-10-26 | 2014-03-12 | 浙江山峪染料化工有限公司 | Method for producing disperse red 343 |
| CN115093344A (en) * | 2022-06-14 | 2022-09-23 | 绍兴市上虞金冠化工有限公司 | Preparation method of cyano-containing azo disperse dye or intermediate |
-
1986
- 1986-09-20 CN CN 86106303 patent/CN86106303A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103627201A (en) * | 2013-10-26 | 2014-03-12 | 浙江山峪染料化工有限公司 | Method for producing disperse red 343 |
| CN103627201B (en) * | 2013-10-26 | 2015-08-26 | 浙江山峪染料化工有限公司 | A kind of method of producing Disperse Red 343 |
| CN115093344A (en) * | 2022-06-14 | 2022-09-23 | 绍兴市上虞金冠化工有限公司 | Preparation method of cyano-containing azo disperse dye or intermediate |
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| WD01 | Invention patent application deemed withdrawn after publication |