CN106831763A - A kind of preparation method of quinacridone and its derivative - Google Patents
A kind of preparation method of quinacridone and its derivative Download PDFInfo
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- CN106831763A CN106831763A CN201611173899.2A CN201611173899A CN106831763A CN 106831763 A CN106831763 A CN 106831763A CN 201611173899 A CN201611173899 A CN 201611173899A CN 106831763 A CN106831763 A CN 106831763A
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- quinacridone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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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
- C09B48/00—Quinacridones
Abstract
The present invention relates to organic pigment synthesis field, the preparation method of a kind of quinacridone and its derivative is disclosed, step is：Dimethyl succinate self-condensation cyclization generation DMSS sodium salt in the presence of sodium methoxide, then it is acidified into DMSS；There is condensation reaction in DMSS, the intermediate product of this condensation generation directly obtains oxidation product with m-nitrobenzene sodium sulfonate oxidation dehydrogenation with aniline or substituted aniline again；Last oxidation product closed loop in the presence of polyphosphoric acids is obtained quinacridone or the crude product of its derivative, most processes to obtain quinacridone or its derivative finished product through pigmentation afterwards.
Description
Technical field
The present invention relates to organic pigment synthesis field, more particularly to a kind of quinacridone and its derivative preparation method.
Background technology
Quinacridone series organic pigment is a kind of tone by the high-grade organic pigment of orange to purple, its heat resistance, resistance to molten
Agent and resistance to migration are splendid, can be widely used in the coloring of coating, plastics, ink, melt spinning etc..
The synthetic method of quinacridone is more, patent CN1207402, CN1176978, CN1668708, CN1717455 etc.
In talk about with hydrogen peroxide oxidation 6, the method that 13- quinacridones prepare quinacridone pigment.Such as patent CN1668708
Specific method be：With hydrogen peroxide as oxidant and in the presence of 2, the 7- anthraquinone disulfonic acids as catalyst, by 6,
13- quinacridone salt is oxidized to corresponding quinacridone pigment.The method of the invention can in high yield obtain high-performance
Quinacridone pigment.
The above method is to prepare a kind of critically important method of quinacridone pigment at present.But face prepared by this process route
Material crude product particle is very thick, behind pigmentation need to carry out ball milling or kneading, energy consumption is very high, and to the pollution of environment
It is larger.
The content of the invention
In order to solve the above-mentioned technical problem, the invention provides a kind of quinacridone and its preparation method of derivative.This
Inventive method process is simple, raw material is easy to get, and can save more times, washings and reaction dissolvent, there is provided more gentle
Oxidizing temperature condition, high financial profit, good product quality.
Concrete technical scheme of the invention is：The preparation method of a kind of quinacridone and its derivative, step is：
Dimethyl succinate self-condensation cyclization generation DMSS sodium salt in the presence of sodium methoxide, then be acidified
Into the DMSS as shown in formula (I)；DMSS occurs with aniline or substituted aniline again
Condensation reaction, the intermediate product of this condensation generation directly obtains the oxygen as shown in formula (II) with m-nitrobenzene sodium sulfonate oxidation dehydrogenation
Change product；Last oxidation product closed loop in the presence of polyphosphoric acids is obtained quinacridone or the crude product of its derivative, most
Quinacridone or its derivative finished product as shown in formula (III) is processed to obtain by pigmentation.
Specific course of reaction is as follows：
Present invention process is simpler, and the condensation of DMSS and oxidation reaction simultaneously make a step, and raw material is easy to get, and can save more
Time, washings and reaction dissolvent, there is provided more gentle oxidizing temperature condition, high financial profit, good product quality, yield
It is high.
Wherein, dimethyl succinate DMS and sodium methoxide, react, in 100~110 DEG C of conditions in specific dicyandiamide solution
Lower generation Claisen condensation (Claisen) and diekmann (Dickman) annulation obtains product, its yield typically 70%~
80% or so.DMS has boiling point (200 DEG C) very high, can also be dissolved each other with arbitrary proportion with methyl alcohol.Use with dimethyl succinate
Not only as reaction raw materials but also as higher boiling atent solvent, the methyl alcohol generated in the methyl alcohol and course of reaction in sodium methoxide solution is made
It is polar latent solvent, reacts to produce DMSS by dimethyl succinate and sodium methoxide.So not only join
It is few with the raw material variety of reaction, without recycling solvent, and reaction is fast, product purity and high income, environmental pollution greatly
Improve, therefore the process of this " solvent-free " synthesis DMSS is highly utilized.
The condensation of DMSS and oxidation reaction under conditions of yield is not influenceed (yield of intermediate oxidation product be 94%,
Unlike the low yield being condensed respectively and aoxidize), it is convenient to omit the product treatment time of condensation and treatment intermediate products institute
The solvent of consumption, can directly successive reaction, i.e. two steps and make a step walk.The temperature of oxidation reaction is more gentle in this one-step method.
Ring-closure reaction only under the solvent of polyphosphoric acids PPA, with intermediate oxidation product reaction, is directly produced crude product
Quinacridone and its derivative.Methyl alcohol or other solvents need not still further be added.
Preferably, the R in formula (I), formula (I), formula (III) is hydrogen, methyl or chlorine.
Preferably, the dimethyl succinate is 3.8-4.2: 1 with the mol ratio of sodium methoxide.
Preferably, the dimethyl succinate is 100-110 DEG C with the reaction temperature of sodium methoxide.
Preferably, the DMSS is 1: 2.4-2.6 with the mol ratio of aniline or substituted aniline.
Preferably, the DMSS is 1: 0.5-0.7 with the mol ratio of m-nitrobenzene sodium sulfonate.
Preferably, oxidizing reaction temperature is 105-115 DEG C.
Because the present invention is by the condensation of DMSS and oxidation reaction and makees a step such that it is able to which the oxidation for providing more temperature is anti-
Temperature is answered, when temperature is set as 105-115 DEG C, effect is more preferable.
Preferably, the oxidation product is 1: 4-6 with the mol ratio of polyphosphoric acids.
Preferably, the oxidation product is added in polyphosphoric acids for batch format.
During significantly intermediate product must be added to PPA in batches in this course of reaction, to promote reaction
Process.And without additionally adding other solvents again in course of reaction.
Preferably, the pigmentation processing procedure is：The crude product of quinacridone or its derivative is entered to be added to
In ethanol, 95-105 DEG C of reflow treatment can obtain quinacridone or its derivative finished product.
It is compared with the prior art, the beneficial effects of the invention are as follows：
1. due to this product often step reaction all along with the change of color in reactant mixture, it is possible to intuitively it was observed that
The generation of DMSS, the generation of the process and quinacridone and its derivative of condensation oxidation one-step method.
2. the methyl alcohol for being produced in course of reaction can be recycled.
The condensation reaction of 3.DMSS and oxidation reaction are merged into a step and do, and the yield of intermediate oxidation product is 94%, not
Than the low yield being condensed respectively and aoxidize, it is possible to time-consuming and washing water consumption etc., the knot of cost efficiency is reached
Really.And the temperature of oxidation reaction is more gentle, required energy consumption is more reduced, improve economic benefit.
Specific embodiment
With reference to embodiment, the invention will be further described.
Embodiment 1
1st, the preparation of DMSS (DMSS)：
In the 1L there-necked flasks equipped with electrical heating magnetic stirring apparatus, thermocouple is loaded onto, constant pressure funnel and condenser pipe (subtract
Pressure distilling apparatus).In there-necked flask, 600g dimethyl succinates DMS (4mol), nitrogen (removing moisture content and oxygen) is added to protect
100 DEG C are warming up under shield.The sodium methoxide solution (1mol) of 180g 30% is slowly added dropwise with constant pressure funnel afterwards, during dropwise addition
Between for 4h or so, after completion of dropwise addition, then react 2h or so.After reaction terminates, product is obtained, pickling, washing, drying obtains 86g
Yellowish color substance DMSS DMSS, yield 75.4%, fusing point 154.6.1HNMR (400MHz, CDCl3), δ/
ppm：1.67 (s, 3H, OCH3), 3.38 (s, 2H, ArH), 3.86 (s, 2H, ArH) products are detected by HPLC, flow phase composition
For acetonitrile-ammonium acetate buffer, (volume ratio is that 65: 35, pH is that 4.0), Detection wavelength is 240nm, and its purity is 97.76%.
2nd, it is condensed and oxidation one-step method：
In the 1L there-necked flasks equipped with electrical heating magnetic stirring apparatus, thermocouple, and straight cold finger (condensing reflux dress are loaded onto
Put).22.8gDMSS (0.1mol), 23.3g aniline (0.25mol), 350ml ethanol solutions and a certain amount of are added in there-necked flask
Hydrochloric acid solution, stirring is warming up to the logical nitrogen of backflow, reacts 6h, reaction terminate after condensation product 2,5- hexichol amido -3,6 two
Hydrogen dimethyl terephthalate (DMT).After repacking condensation reflux unit into distilling apparatus afterwards, 50ml 30%NaOH are separately added into molten
Liquid, 13.5g m-nitrobenzene sodium sulfonates are warming up to 110 DEG C, and reaction is stopped after reaction 3h.Pickling, washing, drying obtains product 2,
5- hexichol amido terephthalic acid (TPA) 33.15g, yield is 95.2%.1HNMR (400MHz, CDCl3), δ/ppm：3.46 (s, 1H,
NH), 4.43 (s, 2H, ArH), 7.68 (s, 4H, ArH).
3rd, ring-closure reaction：
In the 1L there-necked flasks equipped with electrical heating magnetic stirring apparatus, thermocouple and condenser pipe (distilling apparatus) are loaded onto., at three mouthfuls
84.5g polyphosphoric acids PPA (0.25mol) is added in flask, 3h is interior afterwards at 100 DEG C adds 17.4g 2,5- diphenylamines in batches
Base terephthalic acid (TPA) (0.05mol), after adding material, reacts 3h at 125 DEG C, stop reaction.Washing can obtain crude product quinoline a word used for translation
Pyridine ketone 15.82g, yield 99.43%.1HNMR (400MHz, CDCl3), δ/ppm：4.0 (s, 2H, NH), 6.75 (s, 2H, ArH),
7.25 (s, 3H, ArH).Product detects that its purity is 98.49% by HPLC.
4th, pigmentation treatment：
Pigmentation treatment is carried out to crude product quinacridone, by crude product addition ethanol, 100 DEG C of reflow treatments can obtain product
Quinacridone.Its yield is between 94~96%.
Embodiment 2
1st, the preparation of DMSS (DMSS)：
In the 1L there-necked flasks equipped with electrical heating magnetic stirring apparatus, thermocouple is loaded onto, constant pressure funnel and condenser pipe (subtract
Pressure distilling apparatus).In there-necked flask, 600g dimethyl succinates DMS (4mol), nitrogen (removing moisture content and oxygen) is added to protect
100 DEG C are warming up under shield.The sodium methoxide solution (1mol) of 180g 30% is slowly added dropwise with constant pressure funnel afterwards, during dropwise addition
Between for 4h or so, after completion of dropwise addition, then react 2h or so.After reaction terminates, product is obtained, pickling, washing, drying obtains 86g
Yellowish color substance DMSS DMSS, yield 75.4%, fusing point 154.6.1HNMR (400MHz, CDCl3), δ/
ppm：1.67 (s, 3H, OCH3), 3.38 (s, 2H, ArH), 3.86 (s, 2H, ArH) products are detected by HPLC, flow phase composition
For acetonitrile-ammonium acetate buffer, (volume ratio is that 65: 35, pH is that 4.0), Detection wavelength is 240nm, and its purity is 97.76%.
2nd, it is condensed and oxidation one-step method：
In the 1L there-necked flasks equipped with electrical heating magnetic stirring apparatus, thermocouple, and straight cold finger (condensing reflux dress are loaded onto
Put).22.8gDMSS (0.1mol), 26.8g para-totuidine (0.25mol), 350ml ethanol solutions and are added in there-necked flask
Quantitative hydrochloric acid solution, stirs and is warming up to the logical nitrogen of backflow, reacts 6h, and reaction obtains condensation product 2,5- dimethylanilines after terminating
Base -3,6- dihydro dimethyl terephthalate (DMT)s.After repacking condensation reflux unit into distilling apparatus afterwards, 50ml is separately added into
30%NaOH solution, 13.5g m-nitrobenzene sodium sulfonates are warming up to 110 DEG C, and reaction is stopped after reaction 3h.Pickling, washing, drying
Obtain product 2,5- dimethylaniline terephthalic acid (TPA) 35.35g, yield 94.02%.1HNMR (400MHz, CDCl3), δ/ppm：
1.62 (s, 3H, CH3), 4.02 (s, 1H, NH), 4.52 (s, 2H, ArH), 7.57 (s, 3H, ArH).
3rd, ring-closure reaction：
In the 1L there-necked flasks equipped with electrical heating magnetic stirring apparatus, thermocouple and condenser pipe (distilling apparatus) are loaded onto., at three mouthfuls
84.5g polyphosphoric acids PPA (0.25mol) is added in flask, 3h is interior afterwards at 100 DEG C adds 18.8g 2,5- dimethyl in batches
Aniline terephthalic acid (TPA) (0.05mol), after adding material, reacts 3h at 125 DEG C, stop reaction.Washing can obtain crude product 2,
9- dimethylquinacridone 16.93g, yield 99.59%.1HNMR (400MHz, CDCl3), δ/ppm：2.35 (s, 3H, CH3),
4.12 (s, 2H, NH), 6.87 (s, 2H, ArH), 7.34 (s, 3H, ArH).Product detects that its purity is 98.73% by HPLC.
4th, pigmentation treatment：
To crude product 2,9- dimethylquinacridones carry out pigmentation treatment, by crude product add ethanol in, at 100 DEG C of backflows
Reason, can obtain product 2,9- dimethylquinacridones.Its yield is between 94~96%.
Embodiment 3
1st, the preparation of DMSS (DMSS)：
In the 1L there-necked flasks equipped with electrical heating magnetic stirring apparatus, thermocouple is loaded onto, constant pressure funnel and condenser pipe (subtract
Pressure distilling apparatus).In there-necked flask, 600g dimethyl succinates DMS (4mol), nitrogen (removing moisture content and oxygen) is added to protect
100 DEG C are warming up under shield.The sodium methoxide solution (1mol) of 180g 30% is slowly added dropwise with constant pressure funnel afterwards, during dropwise addition
Between for 4h or so, after completion of dropwise addition, then react 2h or so.After reaction terminates, product is obtained, pickling, washing, drying obtains 86g
Yellowish color substance DMSS DMSS, yield 75.4%, fusing point 154.6.1HNMR (400MHz, CDCl3), δ/
ppm：1.67 (s, 3H, OCH3), 3.38 (s, 2H, ArH), 3.86 (s, 2H, ArH) products are detected by HPLC, flow phase composition
For acetonitrile-ammonium acetate buffer, (volume ratio is that 65: 35, pH is that 4.0), Detection wavelength is 240nm, and its purity is 97.76%.
2nd, it is condensed and oxidation one-step method：
In the 1L there-necked flasks equipped with electrical heating magnetic stirring apparatus, thermocouple, and straight cold finger (condensing reflux dress are loaded onto
Put).22.8gDMSS (0.1mol), 31.9g parachloroanilinum (0.25mol), 350ml ethanol solutions and are added in there-necked flask
Quantitative hydrochloric acid solution, stirs and is warming up to the logical nitrogen of backflow, reacts 6h, and reaction obtains condensation product 2, the parachloroanilinum of 5- bis- after terminating
Base -3,6- dihydro dimethyl terephthalate (DMT)s.After repacking condensation reflux unit into distilling apparatus afterwards, 50ml is separately added into
30%NaOH solution, 13.5g m-nitrobenzene sodium sulfonates are warming up to 110 DEG C, and reaction is stopped after reaction 3h.Pickling, washing, drying
Obtain product 2, the parachloroanilinum terephthalic acid (TPA) 40.23g of 5- bis-, yield 96.71%.1HNMR (400MHz, CDCl3), δ/ppm：
3.25 (s, 1H, NH), 4.37 (s, 2H, ArH), 7.16 (s, 1H, ArH), 7.87 (s, 2H, ArH).
3rd, ring-closure reaction：
In the 1L there-necked flasks equipped with electrical heating magnetic stirring apparatus, thermocouple and condenser pipe (distilling apparatus) are loaded onto, at three mouthfuls
84.5g polyphosphoric acids PPA (0.25mol) is added in flask, 3h is interior afterwards at 100 DEG C adds 20.85g 2,5- bis- couples in batches
Chloroaniline terephthalic acid (TPA) (0.05mol), after adding material, reacts 3h at 125 DEG C, stop reaction.Washing can obtain crude product
2,9- dichloro quinacridone 18.97g, yield is 99.53%.1HNMR (400MHz, CDCl3), δ/ppm：4.08 (s, 2H, NH),
6.63 (s, 2H, ArH), 7.41 (s, 3H, ArH).Product detects that its purity is 98.81% by HPLC.
4th, pigmentation treatment：
To crude product 2,9- dichloro quinacridones carry out pigmentation treatment, by crude product add ethanol in, 100 DEG C of reflow treatments,
Product 2,9- dichloro quinacridones can be obtained.Its yield is between 94~96%.
Raw materials used in the present invention, equipment, unless otherwise noted, is the conventional raw material, equipment of this area；In the present invention
Method therefor, unless otherwise noted, is the conventional method of this area.
The above, is only presently preferred embodiments of the present invention, and not the present invention is imposed any restrictions, every according to the present invention
Any simple modification, change and equivalent transformation that technical spirit is made to above example, still fall within the technology of the present invention side
The protection domain of case.
Claims (10)
1. the preparation method of a kind of quinacridone and its derivative, it is characterised in that：Step is：
Dimethyl succinate self-condensation cyclization generation DMSS sodium salt in the presence of sodium methoxide, then be acidified
Into the DMSS as shown in formula (I)；DMSS occurs with aniline or substituted aniline again
Condensation reaction, the intermediate product of this condensation generation directly obtains the oxygen as shown in formula (II) with m-nitrobenzene sodium sulfonate oxidation dehydrogenation
Change product；Last oxidation product closed loop in the presence of polyphosphoric acids is obtained quinacridone or the crude product of its derivative, most
Quinacridone or its derivative finished product as shown in formula (III) is processed to obtain by pigmentation；Specific course of reaction is as follows：
2. the preparation method of a kind of quinacridone as claimed in claim 1 and its derivative, it is characterised in that formula (I), formula
(I), the R in formula (III) is hydrogen, methyl or chlorine.
3. the preparation method of a kind of quinacridone as claimed in claim 1 and its derivative, it is characterised in that the succinic acid
Dimethyl ester is 3.8-4.2: 1 with the mol ratio of sodium methoxide.
4. a kind of quinacridone as described in claim 1 or 3 and its preparation method of derivative, it is characterised in that the fourth
Acid dimethyl is 100-110 DEG C with the reaction temperature of sodium methoxide.
5. the preparation method of a kind of quinacridone as claimed in claim 1 and its derivative, it is characterised in that the succinyl
Dimethyl succinate is 1: 2.4-2.6 with the mol ratio of aniline or substituted aniline.
6. a kind of quinacridone as described in claim 1 or 5 and its preparation method of derivative, it is characterised in that the fourth
Two acyl dimethyl succinates are 1: 0.5-0.7 with the mol ratio of m-nitrobenzene sodium sulfonate.
7. the preparation method of a kind of quinacridone as claimed in claim 6 and its derivative, it is characterised in that oxidation reaction temperature
Spend is 105-115 DEG C.
8. the preparation method of a kind of quinacridone as claimed in claim 1 and its derivative, it is characterised in that the oxidation is produced
Thing is 1: 4-6 with the mol ratio of polyphosphoric acids.
9. the preparation method of a kind of quinacridone as claimed in claim 8 and its derivative, it is characterised in that the oxidation is produced
Thing is added in polyphosphoric acids for batch format.
10. the preparation method of a kind of quinacridone as claimed in claim 1 and its derivative, it is characterised in that the pigment
Changing processing procedure is：The crude product of quinacridone or its derivative is entered to be added in ethanol, 95-105 DEG C of reflow treatment can
Obtain quinacridone or its derivative finished product.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110204919A (en) * | 2019-07-18 | 2019-09-06 | 浙江永泉化学有限公司 | A kind of organic chemical industry's pigment production preparation facilities and method |
| CN110358366A (en) * | 2019-07-05 | 2019-10-22 | 天津科技大学 | A kind of chemical stain fluorescent ink and preparation method and applications |
| CN111019387A (en) * | 2019-12-29 | 2020-04-17 | 河北彩客化学股份有限公司 | Preparation method of 2, 9-dimethyl quinacridone violet red pigment |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1521218A (en) * | 2003-01-28 | 2004-08-18 | 余世春 | Process for preparation of quinacridone series pigments |
| WO2005085364A1 (en) * | 2004-02-20 | 2005-09-15 | Mca Technologies Gmbh | Process for the preparation of organic pigments |
| CN102584593A (en) * | 2012-01-09 | 2012-07-18 | 浙江永泉化学有限公司 | Preparation method for dimethyl succinylo succinate (DMSS) |
-
2016
- 2016-12-18 CN CN201611173899.2A patent/CN106831763A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1521218A (en) * | 2003-01-28 | 2004-08-18 | 余世春 | Process for preparation of quinacridone series pigments |
| WO2005085364A1 (en) * | 2004-02-20 | 2005-09-15 | Mca Technologies Gmbh | Process for the preparation of organic pigments |
| CN102584593A (en) * | 2012-01-09 | 2012-07-18 | 浙江永泉化学有限公司 | Preparation method for dimethyl succinylo succinate (DMSS) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110358366A (en) * | 2019-07-05 | 2019-10-22 | 天津科技大学 | A kind of chemical stain fluorescent ink and preparation method and applications |
| CN110204919A (en) * | 2019-07-18 | 2019-09-06 | 浙江永泉化学有限公司 | A kind of organic chemical industry's pigment production preparation facilities and method |
| CN111019387A (en) * | 2019-12-29 | 2020-04-17 | 河北彩客化学股份有限公司 | Preparation method of 2, 9-dimethyl quinacridone violet red pigment |
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| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170613 |