CN102432505B - Production method of tetrachlorophthalonitrile - Google Patents
Production method of tetrachlorophthalonitrile Download PDFInfo
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- CN102432505B CN102432505B CN201010295676.XA CN201010295676A CN102432505B CN 102432505 B CN102432505 B CN 102432505B CN 201010295676 A CN201010295676 A CN 201010295676A CN 102432505 B CN102432505 B CN 102432505B
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Abstract
The invention discloses a production method of tetrachlorophthalonitrile, which belongs to the field of the manufacturing of farm insecticides. The tetrachlorophthalonitrile is white crystal powder in appearance, is an important organic intermediate, is widely used in the fields of medicines, dyes, the farm insecticides and the like, and has extremely wide purposes. The production method of the tetrachlorophthalonitrile, which is provided by the invention, comprises the following steps: using ortho-xylene, ammonia, air or oxygen, chlorine, nitrogen and a catalyst as raw materials, first, preparing phthalonitrile through an ammoxidation method in a fluidized bed, and then, using the phthalonitrile as a raw material, and producing the tetrachlorophthalonitrile through a gas phase chlorination method, namely a process that the fluidized bed is used prior to a fixed bed. The production method has the advantages of simple process, high efficiency, low cost, short conversion time, no pollution, high yield and the like, and a qualified tetrachlorophthalonitrile product can be produced.
Description
Technical field:
The invention belongs to agricultural chemicals and manufacture field, it is characterized in that the production method relating to a kind of tetrachloro phthalonitrile.
Background technology:
Tetrachloro phthalonitrile, has another name called monoethyl dintrile, and outward appearance is white crystalline powder, and molecular formula is C
8n
2cl
4, fusing point is 248 DEG C-250 DEG C.Tetrachloro phthalonitrile is a kind of important organic intermediate, and be widely used in the fields such as medicine, dyestuff, agricultural chemicals, purposes is very extensive.The present invention is that (molecular formula is for CH with o-Xylol
3c
6h
4cH
3, colourless transparent liquid, has aromatic odour, fusing point-25.2 DEG C, boiling point 144.4 DEG C, can be miscible with ethanol, ether, acetone and benzene, water insoluble, and as phthalic anhydride and other organic synthesis raw materials, mode of producing generally is extracted by certain technique from dimethylbenzene.) in fluidized-bed, produce phthalonitrile by ammonia oxygen method for raw material, the main points of this production method are: one, select catalyzer; Two, will control suitable temperature of reaction, temperature plays important effect in ammonia oxidation strong exothermal reaction, and experiment proves, the optimum temps of this reaction is 320 DEG C-440 DEG C, and when temperature is higher than 440 DEG C, over oxidation occurs; Three, control the air input of ammonia, ammonia is considered to cause in oxidative ammonolysis high reactivity and optionally principal element, and experiment proves, the mol ratio of the best is o-Xylol vapour: ammonia: oxygen (or air)=1:2-18:8-45; In addition, reaction times and pressure are also the factors of impact reaction, and experiment proves, when pressure is 0.05Mpa-0.10Mpa, carrys out obtained phthalonitrile by above-mentioned composition and engineering by fluidized-bed reactor; With obtained phthalonitrile (phthalonitrile: molecular formula C
8h
4n
2, molecular weight is 128.13, and fusing point is 138 DEG C-140 DEG C, and outward appearance is white needle-like crystals, can be used as pigment and fine chemicals intermediate.) for raw material is through the method production tetrachloro phthalonitrile of gas phase chlorination, the production essentials of the method is: one, select suitable temperature and pressure, and the temperature 230 DEG C-250 DEG C of this reaction of experiment proof, pressure are 0.01MPa-0.10Mpa is best; Two, select suitable air inlet ratio and reaction times, the mol ratio being proven air input is phthalonitrile vapour: chlorine: nitrogen=2:5-10:10-40 is for best; Three, select suitable catalyzer, first produce tetrachloro phthalonitrile by fixed bed again by fluidized-bed by above-mentioned composition and engineering.Advantage of the present invention is: technique is simple, production cost is low, pollution-free, product yield is high and quality is good.
Summary of the invention:
In order to overcome the defect that older production technique production cost is high, pollution is large, transformation time is long, the invention provides a kind of is raw material with o-Xylol, first produce phthalonitrile, produce the production method of tetrachloro phthalonitrile again, the method technique is simple, efficiency is high, cost is low, and transformation time is short, pollution-free, can produce qualified tetrachloro phthalonitrile product.
The present invention can be achieved through the following technical solutions:
A method for suitability for industrialized production tetrachloro phthalonitrile, is characterized in that being made up of following steps:
1, quantitative o-Xylol is sent into vaporizer vaporize, take vaporizer out of by air after o-Xylol vaporization and with ammonia mix in a mixer laggard enter fluidized-bed, the mol ratio of three kinds of gas (vapour) bodies is, o-Xylol vapour: ammonia: oxygen (or air)=1:2-18:8-45, temperature in fluidized-bed is adjusted to 320 DEG C-440 DEG C, pressure is 0.05Mpa-0.10Mpa, add the Vanadium Pentoxide in FLAKES accounting for gas volume total amount 0.2%-8% in reactor, the catalyzer making effective constituent makes it react, collector is sent into after gas cooling by after reaction, product phthalonitrile is obtained after condensation is dried, the yield of product is 80%-90%, purity is 99%.
2, phthalonitrile is sent into vaporizer and carry out melting vaporization, take vaporizer out of by nitrogen after phthalonitrile vaporization and with mix in a mixer in chlorine laggard enter fluidized-bed, the mol ratio of air input is phthalonitrile vapour: chlorine: nitrogen=2:5-10:10-40, add catalyst activity charcoal simultaneously, quantity is a 0.2%-8% for internal volume total amount, temperature in fluidized-bed is adjusted to 230 DEG C-280 DEG C, pressure is 0.01MPa-0.10Mpa, after completion of the reaction, after reacting, gas sends into fixed bed, keep the temperature identical with fluidized-bed and pressure, and add the catalyst activity charcoal identical with adding fluidized-bed quantity and chlorine, gas after first set reaction and chlorine are reacted again, reacted mixed gas in fixed bed is sent into collector, tetrachloro phthalonitrile is obtained through condensation post-drying.The yield of this reaction is 85%-95%, and the purity of product is 98%.In this reaction process, chlorine enters fluidized-bed and fixed bed respectively, the load of two reactors is adjusted by adjusting the quantity entering two chlorine, thus reduce the content of Perchlorobenzene, through practice test, the hexachlorobenzene content that this reaction produces only has 40ppm-100ppm, is significantly less than state specified standards.
Fixed bed interior reaction temperature described in above-mentioned steps 1 is 320 DEG C-440 DEG C, and pressure is 0.05Mpa-0.10Mpa
Temperature in above-mentioned steps 2 in fluidized-bed and fixed bed is 230 DEG C-280 DEG C, pressure is 0.01MPa-0.10Mpa.
The invention has the beneficial effects as follows: providing a kind of is raw material with o-Xylol, the production technique of tetrachloro phthalonitrile is produced by ammonia oxygen method, gas-phase chlorination, this production method has that technique is simple, efficiency is high, cost is low, transformation time is short, pollution-free, yield is high, can produce qualified tetrachloro phthalonitrile product.
Embodiment
Embodiment 1
Quantitative o-Xylol is sent into vaporizer vaporize, take vaporizer out of by air after o-Xylol vaporization and with ammonia mix in a mixer laggard enter fluidized-bed, the mol ratio of three kinds of gas (vapour) bodies is, o-Xylol vapour: ammonia: oxygen (or air)=1:2:8, temperature in fluidized-bed is adjusted to 320 DEG C, pressure is 0.05Mpa, adding the catalyzer that the Vanadium Pentoxide in FLAKES accounting for gas volume total amount 0.2% in reactor makes effective constituent makes it react, collector is sent into after gas cooling by after reaction, product phthalonitrile is obtained after condensation is dried, the yield of product is 80%-90%, purity is 99%, phthalonitrile is sent into vaporizer and carry out melting vaporization, take vaporizer out of by nitrogen after phthalonitrile vaporization and with mix in a mixer in chlorine laggard enter fluidized-bed, the mol ratio of air input is phthalonitrile vapour: chlorine: nitrogen=2:5:10, add catalyst activity charcoal simultaneously, quantity is 0.2% of an internal volume total amount, temperature in fluidized-bed is adjusted to 230 DEG C, pressure is 0.01MPa, after completion of the reaction, after reacting, gas sends into fixed bed, keep the temperature identical with fluidized-bed and pressure, and add the catalyst activity charcoal identical with adding fluidized-bed quantity and chlorine, gas after first set reaction and chlorine are reacted again, mixed gas after reaction in fixed bed is sent into collector, tetrachloro phthalonitrile is obtained through condensation post-drying.The yield of this reaction is 85%-95%, and the purity of product is 98%.
Embodiment 2
Quantitative o-Xylol is sent into vaporizer vaporize, take vaporizer out of by air after o-Xylol vaporization and with ammonia mix in a mixer laggard enter fluidized-bed, the mol ratio of three kinds of gas (vapour) bodies is, o-Xylol vapour: ammonia: oxygen (or air)=1:5:15, temperature in fluidized-bed is adjusted to 340 DEG C, pressure is 0.06Mpa, adding the catalyzer that the Vanadium Pentoxide in FLAKES accounting for gas volume total amount 1% in reactor makes effective constituent makes it react, collector is sent into after gas cooling by after reaction, product phthalonitrile is obtained after condensation is dried, the yield of product is 80%-90%, purity is 99%.Phthalonitrile is sent into vaporizer and carry out melting vaporization, take vaporizer out of by nitrogen after phthalonitrile vaporization and with mix in a mixer in chlorine laggard enter fluidized-bed, the mol ratio of air input is phthalonitrile vapour: chlorine: nitrogen=2:6:15, add catalyst activity charcoal simultaneously, quantity is 1% of an internal volume total amount, temperature in fluidized-bed is adjusted to 240 DEG C, pressure is 0.03MPa, after completion of the reaction, after reacting, gas sends into fixed bed, keep the temperature identical with fluidized-bed and pressure, and add the catalyst activity charcoal identical with adding fluidized-bed quantity and chlorine, gas after first set reaction and chlorine are reacted again, mixed gas after reaction in fixed bed is sent into collector, tetrachloro phthalonitrile is obtained through condensation post-drying.The yield of this reaction is 85%-95%, and the purity of product is 98%.
Embodiment 3
Quantitative o-Xylol is sent into vaporizer vaporize, take vaporizer out of by air after o-Xylol vaporization and with ammonia mix in a mixer laggard enter fluidized-bed, the mol ratio of three kinds of gas (vapour) bodies is, o-Xylol vapour: ammonia: oxygen (or air)=1:8:22, temperature in fluidized-bed is adjusted to 360 DEG C, pressure is 0.07Mpa, adding the catalyzer that the Vanadium Pentoxide in FLAKES accounting for gas volume total amount 2% in reactor makes effective constituent makes it react, collector is sent into after gas cooling by after reaction, product phthalonitrile is obtained after condensation is dried, the yield of product is 80%-90%, purity is 99%.Phthalonitrile is sent into vaporizer and carry out melting vaporization, take vaporizer out of by nitrogen after phthalonitrile vaporization and with mix in a mixer in chlorine laggard enter fluidized-bed, the mol ratio of air input is phthalonitrile vapour: chlorine: nitrogen=2:7:20, add catalyst activity charcoal simultaneously, quantity is 2% of an internal volume total amount, temperature in fluidized-bed is adjusted to 250 DEG C, pressure is 0.05Mpa, after completion of the reaction, after reacting, gas sends into fixed bed, keep the temperature identical with fluidized-bed and pressure, and add the catalyst activity charcoal identical with adding fluidized-bed quantity and chlorine, gas after first set reaction and chlorine are reacted again, mixed gas after reaction in fixed bed is sent into collector, tetrachloro phthalonitrile is obtained through condensation post-drying.The yield of this reaction is 85%-95%, and the purity of product is 98%.
Embodiment 4
Quantitative o-Xylol is sent into vaporizer vaporize, take vaporizer out of by air after o-Xylol vaporization and with ammonia mix in a mixer laggard enter fluidized-bed, the mol ratio of three kinds of gas (vapour) bodies is, o-Xylol vapour: ammonia: oxygen (or air)=1:11:29, temperature in fluidized-bed is adjusted to 380 DEG C, pressure is 0.08Mpa, adding the catalyzer that the Vanadium Pentoxide in FLAKES accounting for gas volume total amount 3% in reactor makes effective constituent makes it react, collector is sent into after gas cooling by after reaction, product phthalonitrile is obtained after condensation is dried, the yield of product is 80%-90%, purity is 99%.Phthalonitrile is sent into vaporizer and carry out melting vaporization, take vaporizer out of by nitrogen after phthalonitrile vaporization and with mix in a mixer in chlorine laggard enter fluidized-bed, the mol ratio of air input is phthalonitrile vapour: chlorine: nitrogen=2:8:30, add catalyst activity charcoal simultaneously, quantity is 3% of an internal volume total amount, temperature in fluidized-bed is adjusted to 260 DEG C, pressure is 0.07Mpa, after completion of the reaction, after reacting, gas sends into fixed bed, keep the temperature identical with fluidized-bed and pressure, and add the catalyst activity charcoal identical with adding fluidized-bed quantity and chlorine, gas after first set reaction and chlorine are reacted again, mixed gas after reaction in fixed bed is sent into collector, tetrachloro phthalonitrile is obtained through condensation post-drying.The yield of this reaction is 85%-95%, and the purity of product is 98%.
Embodiment 5
Quantitative o-Xylol is sent into vaporizer vaporize, take vaporizer out of by air after o-Xylol vaporization and with ammonia mix in a mixer laggard enter fluidized-bed, the mol ratio of three kinds of gas (vapour) bodies is, o-Xylol vapour: ammonia: oxygen (or air)=1:14:36, temperature in fluidized-bed is adjusted to 400 DEG C, pressure is 0.09Mpa, adding the catalyzer that the Vanadium Pentoxide in FLAKES accounting for gas volume total amount 4% in reactor makes effective constituent makes it react, collector is sent into after gas cooling by after reaction, product phthalonitrile is obtained after condensation is dried, the yield of product is 80%-90%, purity is 99%.Phthalonitrile is sent into vaporizer and carry out melting vaporization, take vaporizer out of by nitrogen after phthalonitrile vaporization and with mix in a mixer in chlorine laggard enter fluidized-bed, the mol ratio of air input is phthalonitrile vapour: chlorine: nitrogen=2:9:35, add catalyst activity charcoal simultaneously, quantity is 4% of an internal volume total amount, temperature in fluidized-bed is adjusted to 270 DEG C, pressure is 0.09MPa, after completion of the reaction, after reacting, gas sends into fixed bed, keep the temperature identical with fluidized-bed and pressure, and add the catalyst activity charcoal identical with adding fluidized-bed quantity and chlorine, gas after first set reaction and chlorine are reacted again, mixed gas after reaction in fixed bed is sent into collector, tetrachloro phthalonitrile is obtained through condensation post-drying.The yield of this reaction is 85%-95%, and the purity of product is 98%.
Embodiment 6
Quantitative o-Xylol is sent into vaporizer vaporize, take vaporizer out of by air after o-Xylol vaporization and with ammonia mix in a mixer laggard enter fluidized-bed, the mol ratio of three kinds of gas (vapour) bodies is, o-Xylol vapour: ammonia: oxygen (or air)=1:18:45, temperature in fluidized-bed is adjusted to 440 DEG C, pressure is 0.10Mpa, adding the catalyzer that the Vanadium Pentoxide in FLAKES accounting for gas volume total amount 5% in reactor makes effective constituent makes it react, collector is sent into after gas cooling by after reaction, product phthalonitrile is obtained after condensation is dried, the yield of product is 80%-90%, purity is 99%.Phthalonitrile is sent into vaporizer and carry out melting vaporization, take vaporizer out of by nitrogen after phthalonitrile vaporization and with mix in a mixer in chlorine laggard enter fluidized-bed, the mol ratio of air input is phthalonitrile vapour: chlorine: nitrogen=2:10:40, add catalyst activity charcoal simultaneously, quantity is 5% of an internal volume total amount, temperature in fluidized-bed is adjusted to 280 DEG C, pressure is 0.10Mpa, after completion of the reaction, after reacting, gas sends into fixed bed, keep the temperature identical with fluidized-bed and pressure, and add the catalyst activity charcoal identical with adding fluidized-bed quantity and chlorine, gas after first set reaction and chlorine are reacted again, mixed gas after reaction in fixed bed is sent into collector, tetrachloro phthalonitrile is obtained through condensation post-drying.The yield of this reaction is 85%-95%, and the purity of product is 98%.
Claims (3)
1. the production method of a tetrachloro phthalonitrile, the raw material used has: o-Xylol, ammonia, air or oxygen, chlorine, nitrogen, the catalyzer selected as required, it is characterized in that: step one, quantitative o-Xylol is sent into vaporizer vaporize, take vaporizer out of by air or oxygen after o-Xylol vaporization and with ammonia mix in a mixer laggard enter fluidized-bed, the mol ratio of three kinds of gases is o-Xylol vapour: ammonia: oxygen or air=1: 2-18: 8-45, temperature in fluidized-bed is adjusted to 320 DEG C-440 DEG C, pressure is 0.05Mpa-0.10Mpa, adding the catalyzer that the Vanadium Pentoxide in FLAKES accounting for gas volume total amount 0.2%-8% in reactor makes effective constituent makes it react, collector is sent into after gas cooling by after reaction, product phthalonitrile is obtained after condensation is dried, the yield of product is 80%-90%, purity is 99%, step 2, phthalonitrile is sent into vaporizer and carry out melting vaporization, take vaporizer out of by nitrogen after phthalonitrile vaporization and with mix in a mixer in chlorine laggard enter fluidized-bed, the mol ratio of air input is phthalonitrile vapour: chlorine: nitrogen=2: 5-10: 10-40, add catalyst activity charcoal simultaneously, quantity is a 0.2%-8% for internal volume total amount, temperature in fluidized-bed is adjusted to 230 DEG C-280 DEG C, pressure is that 0.01MPa-0.10Mpa reacts, after completion of the reaction, after reacting, gas sends into fixed bed, keep the temperature and pressure identical with fluidized-bed, and add the catalyst activity charcoal identical with adding fluidized-bed quantity and chlorine, gas after first set reaction and chlorine are reacted again, mixed gas after reaction in fixed bed is sent into collector, tetrachloro phthalonitrile is obtained through condensation post-drying, this reaction product yield is 85%-95%, the purity of product is 98%.
2. the production method of a kind of tetrachloro phthalonitrile according to claim 1, in its claim 1, the feature of step one is: when described fluidized-bed interior reaction temperature is 320 DEG C, and corresponding pressure is 0.05Mpa; When temperature of reaction is 340 DEG C, corresponding pressure is 0.06Mpa; When temperature of reaction is 360 DEG C, corresponding pressure is 0.07Mpa; When temperature of reaction is 380 DEG C, corresponding pressure is 0.08Mpa; When temperature of reaction is 400 DEG C, corresponding pressure is 0.09Mpa; When temperature of reaction is 440 DEG C, corresponding pressure is 0.10Mpa.
3. the production method of a kind of tetrachloro phthalonitrile according to claim 1, in its claim 1, the feature of step 2 is: when described fluidized-bed and fixed bed interior reaction temperature are 230 DEG C, and corresponding pressure is 0.01Mpa; When temperature of reaction is 240 DEG C, corresponding pressure is 0.03Mpa; When temperature of reaction is 250 DEG C, corresponding pressure is 0.05Mpa; When temperature of reaction is 260 DEG C, corresponding pressure is 0.07Mpa; When temperature of reaction is 270 DEG C, corresponding pressure is 0.09Mpa, and when temperature of reaction is 280 DEG C, corresponding pressure is 0.10Mpa.
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| CN103740125B (en) * | 2014-01-15 | 2015-06-17 | 河北铢峰凯美考科技有限公司 | Method for preparing copper phthalocyanine pigments |
| CN107935885A (en) * | 2017-11-30 | 2018-04-20 | 江苏维尤纳特精细化工有限公司 | The preparation method of tetrachloro-p-phenylene's dimethoxy nitrile of low content hexachloro-benzene |
| CN109651196B (en) * | 2018-12-27 | 2021-06-29 | 江阴苏利化学股份有限公司 | Process for tower-type continuous desublimation and material collection of chlorothalonil |
| CN112457214B (en) * | 2019-11-07 | 2023-11-24 | 鞍山七彩化学股份有限公司 | Synthesis method of 4-nitrophthalonitrile |
| CN113429317A (en) * | 2021-06-22 | 2021-09-24 | 四川金象赛瑞化工股份有限公司 | Non-liquid phase production method of phthalonitrile |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3855264A (en) * | 1970-05-18 | 1974-12-17 | Jefferson Chem Co Inc | Preparation of halogenated benzonitrile |
| CN85101962A (en) * | 1985-04-01 | 1986-09-03 | 云南省化工研究所 | Manufacture of tetra-chloro-m-phthalonitrile by chlorination of m-phthalonitrile |
| CN1401632A (en) * | 2002-09-24 | 2003-03-12 | 武汉大学 | Catalyst for preparing phthalonitrile, process for preparing such catalyst, and use thereof |
-
2010
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3855264A (en) * | 1970-05-18 | 1974-12-17 | Jefferson Chem Co Inc | Preparation of halogenated benzonitrile |
| CN85101962A (en) * | 1985-04-01 | 1986-09-03 | 云南省化工研究所 | Manufacture of tetra-chloro-m-phthalonitrile by chlorination of m-phthalonitrile |
| CN1401632A (en) * | 2002-09-24 | 2003-03-12 | 武汉大学 | Catalyst for preparing phthalonitrile, process for preparing such catalyst, and use thereof |
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