CN115850995A - Preparation method of solvent yellow 33 - Google Patents
Preparation method of solvent yellow 33 Download PDFInfo
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- CN115850995A CN115850995A CN202211578313.6A CN202211578313A CN115850995A CN 115850995 A CN115850995 A CN 115850995A CN 202211578313 A CN202211578313 A CN 202211578313A CN 115850995 A CN115850995 A CN 115850995A
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- reaction
- solvent
- phthalic anhydride
- temperature
- solvent yellow
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- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 30
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims abstract description 19
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims abstract description 19
- 235000005074 zinc chloride Nutrition 0.000 claims abstract description 15
- 239000011592 zinc chloride Substances 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 12
- 238000009835 boiling Methods 0.000 claims abstract description 11
- 238000001816 cooling Methods 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 238000005406 washing Methods 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 238000005303 weighing Methods 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000012024 dehydrating agents Substances 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 239000002699 waste material Substances 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 238000001914 filtration Methods 0.000 abstract description 3
- 230000035484 reaction time Effects 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 239000002351 wastewater Substances 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 11
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920004933 Terylene® Polymers 0.000 description 1
- 229920006221 acetate fiber Polymers 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004595 color masterbatch Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention relates to a preparation method of solvent yellow 33, belonging to the technical field of chemical dye preparation. The method comprises the following steps: weighing phthalic anhydride and adding the phthalic anhydride into a reaction container; heating to the reaction temperature, dropwise adding 2-methylquinoline, and controlling the temperature of the system to be not lower than 185 ℃ during dropwise adding; after the dropwise addition is finished, preserving the heat for 1-3h at 190-240 ℃; gradient cooling, namely sequentially adding high-boiling point solvents according to requirements, cooling to room temperature, transferring the materials, and filtering to form a wet product; and (5) drying after washing by using an organic solvent to obtain a qualified product. The invention adopts a dripping mode to carry out reaction, can realize 100 percent conversion of the 2-methylquinoline and the phthalic anhydride, and has no waste of raw materials. The used high boiling point solvent can be repeatedly used, and no solvent is wasted. The reaction time is short, and the single reaction yield is high. No zinc chloride is used, and no solid base waste and waste water are generated. The obtained product has the purity of more than 98 percent, no ash and the like, and has remarkable advantages and effects compared with the prior art.
Description
Technical Field
The invention relates to a preparation method of solvent yellow 33, belonging to the technical field of chemical dye preparation.
Background
Solvent yellow 33 is an ideal colorant for various plastics, is widely applied to coloring materials such as daily plastics, bobbin materials, industrial grease, paint ink, color master batches and the like at present, and is also suitable for coloring spinning yarns of chemical fibers, terylene, nylon, acetate fibers and the like. It is also useful for the coloration of alcohol-soluble varnishes, PES, PC, polyesteramines, acrylics, cosmetics and fumes, and occasionally for the coloration of hydrocarbon solvents.
The main synthesis technology at present is to use 2-methylquinoline and phthalic anhydride to react, and (anhydrous) zinc chloride is used as a dehydrating agent to participate in the reaction. For example, as disclosed in the prior art "Lehrbuch der Organischen Chemie, veit and Co., leipzig,1913, vol.1, part 2, p.1360", a preparation method is provided, in which phthalic anhydride is used in an excess amount of 5 times the mole of 2-methylquinoline, the phthalic anhydride is used as both a reaction raw material and a reaction solvent, and anhydrous zinc chloride is added as a dehydrating agent, and the reaction is carried out at 180 to 190 ℃ for 4 hours to produce 2- (2-quinolyl) -1H-indene-1, 3 (2H) -dione, and although the excess phthalic anhydride (melting point of 131 ℃) is added to increase the fluidity of the reaction solution, the phthalic anhydride is solidified when the reaction solution is cooled to room temperature after the reaction is completed, and the treatment is very inconvenient. The great excess phthalic anhydride cannot be recovered, and the cost is also seriously increased. US1963374 discloses a preparation method in which o-dichlorobenzene is added as a reaction solvent and anhydrous zinc chloride is also used as a dehydrating agent, which solves the problem of fluidity of the reaction solution, but the reaction temperature is only 180 ℃ at most due to the limitation of the boiling point (180 ℃) of o-dichlorobenzene, and finally the reaction time is 20 hours or more. In addition, the addition of o-dichlorobenzene as a reaction solvent also increases the solvent recovery cost. In both methods provided above, anhydrous zinc chloride is used, but since zinc chloride readily absorbs water, it becomes very cumbersome to prepare anhydrous zinc chloride. Furthermore, CN103073919A discloses a solvent yellow 33 which, although anhydrous zinc chloride is not used, also employs zinc chloride as a reactant to form a mixture. The zinc chloride is used for participating in the reaction, and in order to ensure the ash content index in the final product, a large amount of water is needed for washing, so that waste and pollution are caused. Meanwhile, 2-methylquinoline is used as a solvent, so that the conversion rate of raw materials is not high, and the single output is low.
Disclosure of Invention
Based on the defects of the prior art, the invention provides a preparation method of solvent yellow 33, which does not use zinc chloride, does not generate solid base waste and wastewater, and adopts a dropwise adding mode to carry out reaction, thereby effectively solving the problems of raw material conversion rate and pollution waste.
In order to solve the problems, the invention adopts the following technical scheme:
a method of preparing solvent yellow 33, the solvent yellow 33 having the reaction formula:
the preparation method comprises the following specific steps:
step 1: weighing phthalic anhydride and adding the phthalic anhydride into a reaction container;
step 2: heating to the reaction temperature, dropwise adding 2-methylquinoline, and controlling the temperature of the system to be not lower than 185 ℃ during dropwise adding;
and step 3: after the dropwise addition is finished, preserving the heat for 1-3h at 190-240 ℃;
and 4, step 4: gradient cooling, wherein a high-boiling-point solvent is added in the cooling process, and the material is transferred and filtered after the temperature is reduced to room temperature, so as to obtain a wet product;
and 5: and (4) washing the wet product formed in the step (4) by using an organic solvent, and drying to obtain a qualified product.
Further, zinc chloride is not used as a dehydrating agent to participate in the reaction in the method.
Further, the mass ratio of the 2-methylquinoline to the phthalic anhydride to the high-boiling solvent is 1:0.9 to 1.2:5.0 to 5.1.
Further, the boiling point of the high boiling point solvent in the fourth step is not lower than 190 ℃.
Further, in the step 5, the organic solvent is methanol, ethanol, acetone and xylene.
The invention has the beneficial effects that:
according to the preparation method provided by the invention, the reaction is carried out in a dropwise adding mode, theoretically, 100% conversion of the 2-methylquinoline and the phthalic anhydride can be realized, and no raw material waste exists. The used high boiling point solvent can be repeatedly used, and no solvent is wasted. The reaction time is short, and the single reaction yield is high. No zinc chloride is used, and no solid base waste and waste water are generated. The obtained product has the purity of more than 98 percent, no ash and the like, and has remarkable advantages and effects compared with the prior art.
Detailed Description
In order to make the features of the present invention more intuitive, embodiments of the present invention are further described below, but the present invention is not limited to the following examples.
The invention relates to a preparation method of solvent yellow 33, wherein the reaction formula of the solvent yellow 33 is as follows:
example 1:
in the preparation method of solvent yellow 33 in this embodiment 1, 994.18g of phthalic anhydride with a concentration of 94% is added, stirring is started after heating and melting, the temperature is continuously increased to the reaction temperature, 1007.54g of 2-methylquinoline with a concentration of 85% is added dropwise, the temperature of the system is controlled to be not lower than 185 ℃ when dropwise adding is performed, the temperature is increased to 220 ℃ after dropwise adding is performed for reaction for 2 hours, gradient cooling is performed after reaction is performed, 5029.49g of quinoline with a boiling point of not lower than 190 ℃ is added according to requirements, the mixture is transferred to a room temperature and subjected to centrifugal filtration to obtain a wet product, and 2000.10g of ethanol is used for leaching and drying. 1252.88g of solvent yellow 33 product is finally obtained, the purity is 98.35%, no ash is detected through experimental detection, and the yield is 73.38%.
Example 2:
in the preparation method of solvent yellow 33 in this embodiment 2, 749.57g of phthalic anhydride with a concentration of 94% is added, the mixture is stirred after being heated to be molten, the temperature is continuously heated to a reaction temperature, 751.43g of 2-methylquinoline with a concentration of 85% is dropwise added, the temperature of the system is controlled to be not lower than 185 ℃ during dropwise addition, the temperature is heated to 210 ℃ after dropwise addition is completed, the reaction is carried out for 2.5 hours, gradient cooling is started after the reaction is completed, 3761.01g of quinoline with a boiling point of not lower than 190 ℃ is added according to requirements, the mixture is cooled to room temperature, a wet product is obtained by material transferring, centrifugal filtration, washing with 1578.00g of xylene, and drying. 1128.78g of solvent yellow 33 product is finally obtained, the purity is 99.20%, no ash is detected through experimental detection, and the yield is 88.73%.
Comparative example:
an experiment was carried out according to CN103073919A, in which 50.0g of phthalic anhydride, 9.2g of ordinary grade zinc chloride and 483.0g of 2-methylquinoline were weighed out and introduced into a 1000mL reaction flask with mechanical stirring and an air condenser tube. The temperature of the reaction flask was heated to 245 ℃ and kept at this temperature for 2 hours to effect a reaction. And after the reaction is finished, cooling to room temperature. The mixed product was filtered to obtain a cake and a filtrate. The filter cake was washed 3 times with 50mL of ethanol and dried at 80 ℃ for 5 hours to give 2- (2-quinolyl) -1H-indene-1, 3 (2H) -dione with a purity of 95.3%. The weight of the obtained target product was 68.2g, ash content was 0.25%, purity was 95.3%, and yield was 73.9%.
Comparison of example 1 of the present invention with CN103073919A shows that: the invention adopts dropwise addition for reaction, improves the reaction conversion rate, and has high product purity and no ash content.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope of the present invention are included in the scope of the present invention.
Claims (5)
1. A method of preparing solvent yellow 33, the solvent yellow 33 having the reaction formula:
the preparation method is characterized by comprising the following specific steps:
step 1: weighing phthalic anhydride and adding the phthalic anhydride into a reaction container;
step 2: heating to the reaction temperature, dropwise adding 2-methylquinoline, and controlling the temperature of the system to be not lower than 185 ℃ during dropwise adding;
and step 3: after the dropwise addition is finished, preserving the heat for 1-3h at 190-240 ℃;
and 4, step 4: gradient cooling, wherein a high-boiling-point solvent is added in the cooling process, and the material is transferred and filtered after the temperature is reduced to room temperature, so as to obtain a wet product;
and 5: and (4) washing the wet product formed in the step (4) by using an organic solvent, and drying to obtain a qualified product.
2. The process of claim 1, wherein the solvent yellow 33 is selected from the group consisting of: in the method, zinc chloride is not used as a dehydrating agent to participate in the reaction.
3. The method of claim 2, wherein the solvent yellow 33 is selected from the group consisting of: the mass ratio of the 2-methylquinoline to the phthalic anhydride to the high-boiling-point solvent is 1:0.9 to 1.2:5.0 to 5.1.
4. A method of producing solvent yellow 33 according to claim 3, wherein: the boiling point of the high boiling point solvent in the fourth step is not lower than 190 ℃.
5. The method of claim 4, wherein the solvent yellow 33 is selected from the group consisting of: in the step 5, the organic solvent is methanol, ethanol, acetone or xylene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211578313.6A CN115850995B (en) | 2022-12-09 | 2022-12-09 | Preparation method of solvent yellow 33 |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211578313.6A CN115850995B (en) | 2022-12-09 | 2022-12-09 | Preparation method of solvent yellow 33 |
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| Publication Number | Publication Date |
|---|---|
| CN115850995A true CN115850995A (en) | 2023-03-28 |
| CN115850995B CN115850995B (en) | 2023-12-12 |
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1331559A (en) * | 1970-08-14 | 1973-09-26 | Mitsubishi Chemical Ind Ld | Hydroxyquinophthalone colouring material |
| JPH03118365A (en) * | 1989-09-29 | 1991-05-20 | Kawasaki Steel Corp | Production of quinophthalone compound from tar base oil |
| US5468862A (en) * | 1994-04-25 | 1995-11-21 | Warner-Jenkinson Company | Synthesis of Solvent Yellow 33 (D & C Yellow 11) with excess phthalic anhydride acid as a solvent |
| CN102295837A (en) * | 2011-06-02 | 2011-12-28 | 浙江龙盛集团股份有限公司 | Preparation method for disperse yellow dye |
| CN103073919A (en) * | 2013-02-05 | 2013-05-01 | 上海煦旻化工科技发展有限公司 | Solvent yellow 33 |
| CN105669545A (en) * | 2016-03-15 | 2016-06-15 | 江苏华尔化工有限公司 | Preparation technology of dye disperse yellow 54# |
| CN108467361A (en) * | 2017-02-23 | 2018-08-31 | 江苏视科新材料股份有限公司 | A kind of quinophthalone compound, preparation method and the application as light absorbent |
-
2022
- 2022-12-09 CN CN202211578313.6A patent/CN115850995B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1331559A (en) * | 1970-08-14 | 1973-09-26 | Mitsubishi Chemical Ind Ld | Hydroxyquinophthalone colouring material |
| JPH03118365A (en) * | 1989-09-29 | 1991-05-20 | Kawasaki Steel Corp | Production of quinophthalone compound from tar base oil |
| US5468862A (en) * | 1994-04-25 | 1995-11-21 | Warner-Jenkinson Company | Synthesis of Solvent Yellow 33 (D & C Yellow 11) with excess phthalic anhydride acid as a solvent |
| CN102295837A (en) * | 2011-06-02 | 2011-12-28 | 浙江龙盛集团股份有限公司 | Preparation method for disperse yellow dye |
| CN103073919A (en) * | 2013-02-05 | 2013-05-01 | 上海煦旻化工科技发展有限公司 | Solvent yellow 33 |
| CN105669545A (en) * | 2016-03-15 | 2016-06-15 | 江苏华尔化工有限公司 | Preparation technology of dye disperse yellow 54# |
| CN108467361A (en) * | 2017-02-23 | 2018-08-31 | 江苏视科新材料股份有限公司 | A kind of quinophthalone compound, preparation method and the application as light absorbent |
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| CN115850995B (en) | 2023-12-12 |
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