CN101955687A - Method for preparing C.I. pigment yellow 110 - Google Patents
Method for preparing C.I. pigment yellow 110 Download PDFInfo
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- CN101955687A CN101955687A CN2009101817381A CN200910181738A CN101955687A CN 101955687 A CN101955687 A CN 101955687A CN 2009101817381 A CN2009101817381 A CN 2009101817381A CN 200910181738 A CN200910181738 A CN 200910181738A CN 101955687 A CN101955687 A CN 101955687A
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- pigment yellow
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- 239000000049 pigment Substances 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000002904 solvent Substances 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000005406 washing Methods 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000004202 carbamide Substances 0.000 claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 15
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 14
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 10
- 229940117389 dichlorobenzene Drugs 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- LPUUYZVKCMCHLO-UHFFFAOYSA-N 4,5,6,7-tetrachloroisoindole-1,3-dione Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)NC(=O)C2=C1Cl LPUUYZVKCMCHLO-UHFFFAOYSA-N 0.000 claims description 3
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 abstract description 4
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 abstract 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- 238000007098 aminolysis reaction Methods 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- HQODYWHDMASLQN-UHFFFAOYSA-N O1C=COC=C1.N1=NN=CC=C1 Chemical compound O1C=COC=C1.N1=NN=CC=C1 HQODYWHDMASLQN-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
- 235000018660 ammonium molybdate Nutrition 0.000 description 1
- 239000011609 ammonium molybdate Substances 0.000 description 1
- 229940010552 ammonium molybdate Drugs 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003251 chemically resistant material Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
- FGFUBBNNYLNVLJ-UHFFFAOYSA-N indolone Natural products C1=CC=C2C(=O)C=NC2=C1 FGFUBBNNYLNVLJ-UHFFFAOYSA-N 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000002518 isoindoles Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XYQXGZLLGNQFSL-UHFFFAOYSA-N methyl 2,3,4,5-tetrachloro-6-cyanobenzoate Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C#N XYQXGZLLGNQFSL-UHFFFAOYSA-N 0.000 description 1
- -1 monoethyl dicyan Chemical compound 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Abstract
The invention discloses a method for preparing C.I. pigment yellow 110, which comprises the following steps: A, reacting tetrachlorophthalic anhydride (serving as raw material) with urea in appropriate solvent, or reacting tetrachlorophthalic anhydride with ammonia so as to generate phthalimide; B, adding a small amount of catalyst into appropriate solvent so as to react the phthalimide with para-phenylene diamine, then generating a compound; and C, reacting the compound (I) obtained in step B with condensing agent or dehydrating agent in appropriate solvent, after the reaction is completed, cooling the obtained product, then washing the obtained product sequentially by using methanol and water so as to obtain finished pigment. By using the method of the invention, the yield can reach 70 percent.
Description
Technical field
The present invention relates to a kind of preparation method of pigment, be specifically related to a kind of preparation method of C.I. Pigment Yellow 73 110.
Background technology
C.I. Pigment Yellow 73 110 molecular formula are
Above-mentioned structure is called isoindolinone.Isoindolinone pigment sees the report of u s company the earliest, and what still release this pigment the earliest is ciba-Gneigy company.This indolinone pigment is middle 1960s, continue quinacridone pigment with a kind of new pigment that grows up behind the triazine dioxin pigment.This class pigment has the heat-resisting of excellence, sun-proof, character such as weather-proof, anti-solvent and chemically-resistant material.
Isoindolinone pigment synthetic mainly contains 4 kinds of methods traditionally: (1) tetrachlorophthalic anhydride and urea generate 3-imines-4,5,6,7-tetrachloro indolone in ammonium molybdate catalysis, and the latter is condensed into pigment with diamine in high boiling solvent; (2) monoethyl dicyan and ammonia and should react and generate 3-imines-4,5,6,7-tetrachloro 1-isoindolinone, the latter be in high boiling solvent with diamine condensation formation pigment; (3) propose a kind of elder generation in patent CH363980 and synthesize the tetrachloro cyano-benzoic acid methyl ester by tetrachlorophthalic anhydride, it and methyl alcohol reaction generate 3,3-dimethoxy-4 ', 5,6,7-tetrachloro isoindole-1-ketone, the last method that forms pigment again with the diamine condensation; (4) in patent CH346218, propose again a kind of by 3,3, the method for 4,5,6,7 dichloro isoindole-1-ketone and diamine condensation in dichlorobenzene forming pigment.Method (2) wherein, (4) are production method the most commonly used.Wherein the fine price of starting raw material O-phthalic in (2) is comparatively expensive, and harsh with the ammonia react condition.Total recovery hangs down about 50%.3,3,4,5,6 of method (4), 7-tetrachloro indoles are more difficult to get and unstable being difficult for preserved yield also not high about 55%.It is that raw material is gone through this isoindole pigment of multistep synthetic with the tetrachlorophthalic tetrachlorophthalic anhydrid that patent De2321511 was arranged afterwards, and technology is comparatively optimized.Route is as follows substantially,, is separated with the logical ammonia ammonia of PCl3 chloride then, and then uses PBr through the Ursol D aminolysis by tetrachlorophthalic tetrachlorophthalic anhydrid
5Dehydration and ring obtain pigment yield better about 65%.This processing step is all harsh to control then, and reaction is difficult to control.And with DMF is that solvent is difficult to reclaim.And PCl in the chloride step
3Excessive in a large number, in causing and the time inorganic salt a lot, also have the phosphite contaminated wastewater heavier.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art, a kind of preparation method of C.I. Pigment Yellow 73 110 is provided, long to overcome in the traditional technology route, yield is not high, and cost is higher, and the process time is long, pollutes the problem that heavily waits.
Technical scheme of the present invention is: the employing tetrachloro-phthalimide be raw material (can make) by tetrachlorophthalic tetrachlorophthalic anhydrid and urea with Ursol D and little amount of catalyst direct aminolysis in solvent obtain intermediate then with PCl
5Condensation obtains pigment.
A kind of preparation method of C.I. Pigment Yellow 73 110 comprises the steps:
A, starting material use tetrachlorophthalic tetrachlorophthalic anhydrid, with urea reaction, perhaps generate phthalic imidine with ammonia gas react in appropriate solvent.This solvent can be dimethylbenzene, oil of mirbane, and chlorobenzene, the solvent dichlorobenzene, temperature suitably is 100～180 ℃, is good with 130～150 ℃ especially.
B adds little amount of catalyst and Ursol D reacting generating compound (I) structure is as follows with the tetrachloro-phthalimide of above-mentioned generation in appropriate solvent
Solvent can be used chlorobenzene, dichlorobenzene, and dimethylbenzene is with solvent dichlorobenzene the best.Catalyzer can be used KOH, K2CO3, and tosic acid etc., temperature of reaction 50-130 ℃, wherein best with 70-90 ℃.Be difficult for reaction because temperature is low, the too high reaction product of temperature is easily decomposed, and the time is controlled at 2-6h, and especially 3-4h is for well, and the time is too short, and reaction may not finished, and the foreign material change of long generation is many.
C, (I) that generate with B reacts with condensing agent or dewatering agent in appropriate solvent, and solvent is generally used trichlorobenzene, dichlorobenzene, chlorobenzene, toluene, dimethylbenzene, oil of mirbane, and rudimentary polychloroalkane, condensing agent can be used PCl
5, PBr
3, POCl
3, POBr
3, the reaction times temperature 50-130 ℃, especially is advisable with 60-100 ℃ between 0-5h.Reaction finishes postcooling and uses methyl alcohol successively, and water washing obtains finished product pigment, and yield can reach 70%.
Beneficial effect: the present invention at first separates the ammonia in the traditional technology the three steps merging of chloride aminolysis and finishes with two step aminolysis, and has avoided the use of DMF, thereby need not separate purification waste liquid (DMF+H
2O), the yield that obtains intermediate (I) is higher greater than 98%, and solvent slop can use simple separatory, and distillation obtains reclaiming.
Embodiment
The invention will be further described below in conjunction with embodiment:
Embodiment one
Get tetrachlorophthalic tetrachlorophthalic anhydrid 286g, join in the oil of mirbane of 1000ml and be warmed up to 130 ℃, stir the back and add urea 32g, react four hours postcooling to 70 ℃ adding K
2CO
32g adds Ursol D 54g, and react postcooling to 20 ℃ filtration in 5 hours and use methyl alcohol successively, water washing, oven dry obtains intermediate (I).This intermediate joined be warming up to 70 ℃ in the 1000ml dichlorobenzene, add PCl5 reaction 3h postcooling and filter and uses methyl alcohol successively, water washing, oven dry at last promptly obtains C.I. Pigment Yellow 73 110208g.
Embodiment two
Get tetrachlorophthalic tetrachlorophthalic anhydrid 286g, join in the dimethylbenzene of 1000ml and be warmed up to 144 ℃, slowly add urea 32g in the stirring, four hours postcooling to 70 of insulation reaction ℃ add K
2CO
32g adds Ursol D 54g then, and react postcooling to 20 ℃ filtration in 5 hours and use methyl alcohol successively, water washing, oven dry obtains intermediate (I).Again this intermediate is joined 1000ml1, be warming up to 70 ℃ in 1 ethylene dichloride, add PCl
5Reaction 5h postcooling filters uses methyl alcohol successively, water washing, and oven dry at last promptly obtains C.I. Pigment Yellow 73 110205g.
Embodiment three
Get tetrachlorophthalic tetrachlorophthalic anhydrid 286g, join in the oil of mirbane of 1000ml and be warmed up to 150 ℃, stir the back and add urea 32g, react four hours postcooling to 90 ℃ adding KOH 1g, add Ursol D 54g, react postcooling to 20 ℃ filtration in 3 hours and use methyl alcohol successively, water washing, oven dry obtains intermediate (I).This intermediate joined be warming up to 90 ℃ in the 1000ml chlorobenzene, add PCl
5Reaction 4h postcooling filters uses methyl alcohol successively, water washing, and oven dry at last promptly obtains C.I. Pigment Yellow 73 110203g.
Claims (10)
1. the preparation method of a C.I. Pigment Yellow 73 110 is characterized in that: comprise the steps:
A, starting material use tetrachlorophthalic tetrachlorophthalic anhydrid, with urea reaction, perhaps generate phthalic imidine with ammonia gas react in appropriate solvent;
B adds little amount of catalyst and Ursol D reacting generating compound (I) structure is as follows with the tetrachloro-phthalimide of above-mentioned generation in appropriate solvent
C, (I) that generate with B reacts with condensing agent or dewatering agent in appropriate solvent, and reaction finishes postcooling and uses methyl alcohol successively, and water washing obtains finished product pigment.
2. the preparation method of a kind of C.I. Pigment Yellow 73 110 according to claim 1 is characterized in that: solvent is a dimethylbenzene in the steps A, oil of mirbane, and chlorobenzene, the solvent dichlorobenzene, temperature is 100-180 ℃.
3. the preparation method of a kind of C.I. Pigment Yellow 73 110 according to claim 2 is characterized in that: the steps A temperature is 130-150 ℃.
4. the preparation method of a kind of C.I. Pigment Yellow 73 110 according to claim 1 is characterized in that: step B solvent chlorobenzene, dichlorobenzene, dimethylbenzene.
5. the preparation method of a kind of C.I. Pigment Yellow 73 110 according to claim 4 is characterized in that: step B solvent dichlorobenzene.
6. the preparation method of a kind of C.I. Pigment Yellow 73 110 according to claim 1 is characterized in that: step B catalyzer KOH, and K2CO3, tosic acid, temperature of reaction 50-130 ℃, the time is controlled at 2-6h.
7. the preparation method of a kind of C.I. Pigment Yellow 73 110 according to claim 6 is characterized in that: 70-90 ℃ of step B temperature of reaction, the time is controlled at 3-4h.
8. the preparation method of a kind of C.I. Pigment Yellow 73 110 according to claim 1 is characterized in that: step C solvent trichlorobenzene, dichlorobenzene, chlorobenzene, toluene, dimethylbenzene, oil of mirbane, and rudimentary polychloroalkane.
9. the preparation method of a kind of C.I. Pigment Yellow 73 110 according to claim 1 is characterized in that: step C condensing agent PCl
5, PBr
3, POCl
3, POBr
3, the reaction times between 0-5h, temperature 50-130 ℃.
10. the preparation method of a kind of C.I. Pigment Yellow 73 110 according to claim 9 is characterized in that: step C temperature is 60-100 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009101817381A CN101955687A (en) | 2009-07-16 | 2009-07-16 | Method for preparing C.I. pigment yellow 110 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009101817381A CN101955687A (en) | 2009-07-16 | 2009-07-16 | Method for preparing C.I. pigment yellow 110 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101955687A true CN101955687A (en) | 2011-01-26 |
Family
ID=43483290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2009101817381A Pending CN101955687A (en) | 2009-07-16 | 2009-07-16 | Method for preparing C.I. pigment yellow 110 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101955687A (en) |
-
2009
- 2009-07-16 CN CN2009101817381A patent/CN101955687A/en active Pending
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|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
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Application publication date: 20110126 |