CN102432503B - Production method of pentachlorobenzonitrile - Google Patents
Production method of pentachlorobenzonitrile Download PDFInfo
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- CN102432503B CN102432503B CN201010295691.4A CN201010295691A CN102432503B CN 102432503 B CN102432503 B CN 102432503B CN 201010295691 A CN201010295691 A CN 201010295691A CN 102432503 B CN102432503 B CN 102432503B
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Abstract
The invention discloses a production method of pentachlorobenzonitrile, which belongs to the field of the manufacturing of farm insecticides. The pentachlorobenzonitrile is white or almost white crystal powder in appearance, is an important intermediate of the farm insecticides, and has extremely wide purposes. The production method of the pentachlorobenzonitrile, which is provided by the invention, comprises the following steps: using toluene, ammonia, air or oxygen, chlorine, nitrogen and a catalyst as raw materials, first, preparing benzonitrile through an ammoxidation method in a fixed bed, and then, using the benzonitrile as a raw material, and producing the pentachlorobenzonitrile through a gas phase chlorination method, namely a process that a fluidized bed is used prior to the 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 pentachlorobenzonitrile product can be produced.
Description
Art:
The invention belongs to agricultural chemicals and manufacture field, it is characterized in that the production method relating to a kind of pentachlorobenzonitrile.
Background technology:
Pentachlorobenzonitrile, another name pentachlorobenzene cyanogen; 2,3,4,5,6-pentachlorobenzonitrile; 2,3,4,5,6-Perchlorobenzonitrile, outward appearance is white or off-white color crystalline powder, and molecular formula is C7Cl5N, and molecular weight is 275.34.Pentachlorobenzonitrile is a kind of important pesticide intermediate, purposes is very extensive, the technique of its synthesis is more, the present invention is one wherein, with toluene (toluene, molecular formula is C7H8, it is a kind of colourless, volatile liquid with special aromatising flavour, one of aromatic hydrocarbons, its a lot of character and benzene are very alike, but toxicity is much smaller than benzene, it is a kind of conventional industrial chemicals, can be used for manufacturing explosive, agricultural chemicals, phenylformic acid, cyanobenzene, dyestuff, synthetic resins and terylene etc., it is also one of component of gasoline simultaneously, how to extract from oil.) get cyanobenzene by ammonia oxygen legal system for raw material, the main points of this production method are: one, select or produce suitable catalyzer voluntarily; Two, will control suitable temperature of reaction, temperature is more difficult control in ammonia oxidation strong exothermal reaction, facts have proved, when temperature is higher than 430 DEG C, over oxidation occurs, and cyanobenzene selectivity is declined; Three, the air input of ammonia is controlled, ammonia is considered to cause in oxidative ammonolysis high reactivity and optionally principal element, facts have proved, best mol ratio is toluene vapour: ammonia: oxygen (or air)=1: 5-10: 30-35, carrys out obtained cyanobenzene by fixed-bed reactor.With obtained cyanobenzene, (cyanobenzene, molecular formula is C7H5N, and molecular weight is 103.12, and outward appearance is colourless oil liquid, has the smell of almond, and fusing point is-12.8 DEG C, and boiling point is 190.7 DEG C, is slightly soluble in cold water, is dissolved in hot water, is soluble in ethanol, ether.) for raw material is through the method production pentachlorobenzonitrile of gas phase chlorination, the production essentials of the method is: one, select suitable temperature and pressure, prove the temperature 180 DEG C-220 DEG C of this reaction through repeatedly testing, pressure be 0.01MPa-0.10Mpa is best; Two, select suitable air inlet ratio and reaction times, the mol ratio being proven air input is cyanobenzene vapour: chlorine: nitrogen=2-3: 4-9: 6-36 for best, three, select suitable catalyzer, by fluidized-bed and fixed bed production pentachlorobenzonitrile.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 that raw material carrys out production pentachlorobenzonitrile by oxidation proceses of ammonia, gas-phase chlorination with toluene, the method has that technique is simple, production cost is low, pollution-free, product yield is high and the measured advantage of matter, and producing the raw material that this product uses has: toluene, ammonia, oxygen or air, nitrogen, chlorine and catalyzer.
The present invention can be achieved through the following technical solutions:
A method for suitability for industrialized production pentachlorobenzonitrile, is characterized in that being made up of following steps:
1, quantitative toluene is sent into vaporizer vaporize, take vaporizer out of by air after toluene vaporization and enter fixed bed after mixing in a mixer with ammonia, the mol ratio of three kinds of gas (vapour) bodies is, toluene vapour: ammonia: air=1: 5-10: 30-35, temperature in fixed bed is adjusted to 380 DEG C-430 DEG C, pressure is 0.05MPa-0.10Mpa, add the BN-98 toluene prepared by ammoxidation cyanobenzene catalyzer accounting for gas gross 0.2%, reaction 0.3-0.5 hour, collector is sent into after gas decompression cooling by after reaction, products benzene formonitrile HCN liquid is obtained after condensation, the yield of product is 90%--95%, purity is 99.5%.
2, cyanobenzene is sent into vaporizer vaporize, take vaporizer out of by nitrogen after cyanobenzene vaporization and with chlorine mix in a mixer laggard enter fluidized-bed, the mol ratio of air input is cyanobenzene: chlorine: nitrogen=2-3: 4-9: 6-36, add catalyst activity charcoal simultaneously, quantity is the 0.2%-8% of gas gross in bed, temperature in fluidized-bed is adjusted to 180 DEG C-220 DEG C, pressure is 0.01MPa-0.10Mpa, reacted gas is sent 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, after reaction terminates, mixed gas after reaction in fixed bed is sent into collector, pentachlorobenzonitrile is obtained through condensation post-drying.The yield of this reaction is 80%-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 380 DEG C-430 DEG C, and pressure is 0.01MPa-0.10Mpa,
Temperature in above-mentioned steps 2 in fluidized-bed and fixed bed is 180 DEG C-220 DEG C, pressure is 0.01MPa-0.10Mpa.
The invention has the beneficial effects as follows: provide a kind of with the toluene of large low price for raw material, by ammonia oxygen method, gas-phase chlorination production pentachlorobenzonitrile, this production method has that technique is simple, efficiency is high, and cost is low, transformation time is short, pollution-free, can produce qualified pentachlorobenzonitrile product.
Embodiment
Embodiment 1
Quantitative toluene is sent into vaporizer vaporize, take vaporizer out of by air after toluene vaporization and enter fixed bed after mixing in a mixer with ammonia, the mol ratio of three kinds of gas (vapour) bodies is, toluene vapour: ammonia: air=1: 5: 30, temperature in fixed bed is adjusted to 380 DEG C, pressure is 0.05MPa, add the BN-98 toluene prepared by ammoxidation cyanobenzene catalyzer accounting for gas gross 0.2%, reaction 0.3-0.5 hour, collector is sent into after gas decompression cooling by after reaction, products benzene formonitrile HCN liquid is obtained after condensation, the yield of product is 90%--95%, purity is 99.5%, cyanobenzene is sent into vaporizer vaporize, take vaporizer out of by nitrogen after cyanobenzene vaporization and with mix in a mixer in chlorine laggard enter fluidized-bed, the mol ratio of air input is cyanobenzene vapour: chlorine: nitrogen=2: 4: 6, add catalyst activity charcoal simultaneously, quantity is 0.2% of gas gross in bed, temperature in fluidized-bed is adjusted to 180 DEG C, pressure is 0.01MPa, 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, after reaction terminates, mixed gas after reaction in fixed bed is sent into collector, pentachlorobenzonitrile is obtained through condensation post-drying.The yield of this reaction is 80%-95%, and the purity of product is 98%.
Embodiment 2
Quantitative toluene is sent into vaporizer vaporize, take vaporizer out of by air after toluene vaporization and enter fixed bed after mixing in a mixer with ammonia, the mol ratio of three kinds of gas (vapour) bodies is, toluene vapour: ammonia: air=1: 6: 31, temperature in fixed bed is adjusted to 390 DEG C, pressure is 0.06MPa, add the BN-98 toluene prepared by ammoxidation cyanobenzene catalyzer accounting for gas gross 0.2%, reaction 0.3-0.5 hour, collector is sent into after gas decompression cooling by after reaction, products benzene formonitrile HCN liquid is obtained after condensation, the yield of product is 90%--95%, purity is 99.5%, cyanobenzene is sent into vaporizer vaporize, take vaporizer out of by nitrogen after cyanobenzene vaporization and with mix in a mixer in chlorine laggard enter fluidized-bed, the mol ratio of air input is cyanobenzene vapour: chlorine: nitrogen=2.2: 5: 12, add catalyst activity charcoal simultaneously, quantity is 0.6% of gas gross in bed, temperature in fluidized-bed is adjusted to 190 DEG C, pressure is 0.02Mpa, 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, after reaction terminates, mixed gas after reaction in fixed bed is sent into collector, pentachlorobenzonitrile is obtained through condensation post-drying.The yield of this reaction is 80%-95%, and the purity of product is 98%.
Embodiment 3
Quantitative toluene is sent into vaporizer vaporize, take vaporizer out of by air after toluene vaporization and enter fixed bed after mixing in a mixer with ammonia, the mol ratio of three kinds of gas (vapour) bodies is, toluene vapour: ammonia: air=1: 7: 32, temperature in fixed bed is adjusted to 400 DEG C, pressure is 0.07MPa, add the BN-98 toluene prepared by ammoxidation cyanobenzene catalyzer accounting for gas gross 0.2%, reaction 0.3-0.5 hour, collector is sent into after gas decompression cooling by after reaction, products benzene formonitrile HCN liquid is obtained after condensation, the yield of product is 90%--95%, purity is 99.5%, cyanobenzene is sent into vaporizer vaporize, take vaporizer out of by nitrogen after cyanobenzene vaporization and with mix in a mixer in chlorine laggard enter fluidized-bed, the mol ratio of air input is cyanobenzene vapour: chlorine: nitrogen=2.4: 6: 18, add catalyst activity charcoal simultaneously, quantity is 1% of gas gross in bed, temperature in fluidized-bed is adjusted to 200 DEG C, pressure is 0.03MPa, 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, after reaction terminates, mixed gas after reaction in fixed bed is sent into collector, pentachlorobenzonitrile is obtained through condensation post-drying.The yield of this reaction is 80%-95%, and the purity of product is 98%.
Embodiment 4
Quantitative toluene is sent into vaporizer vaporize, take vaporizer out of by air after toluene vaporization and enter fixed bed after mixing in a mixer with ammonia, the mol ratio of three kinds of gas (vapour) bodies is, toluene vapour: ammonia: air=1: 8: 33, temperature in fixed bed is adjusted to 410 DEG C, pressure is 0.08MPa, add the BN-98 toluene prepared by ammoxidation cyanobenzene catalyzer accounting for gas gross 0.2%, reaction 0.3-0.5 hour, collector is sent into after gas decompression cooling by after reaction, products benzene formonitrile HCN liquid is obtained after condensation, the yield of product is 90%--95%, purity is 99.5%, cyanobenzene is sent into vaporizer vaporize, take vaporizer out of by nitrogen after cyanobenzene vaporization and with mix in a mixer in chlorine laggard enter fluidized-bed, the mol ratio of air input is cyanobenzene vapour: chlorine: nitrogen=2.6: 7: 24, add catalyst activity charcoal simultaneously, quantity is 1.5% of gas gross in bed, temperature in fluidized-bed is adjusted to 210 DEG C, pressure is 0.04MPa, 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, after reaction terminates, mixed gas after reaction in fixed bed is sent into collector, pentachlorobenzonitrile is obtained through condensation post-drying.The yield of this reaction is 80%-95%, and the purity of product is 98%.
Embodiment 5
Quantitative toluene is sent into vaporizer vaporize, take vaporizer out of by air after toluene vaporization and enter fixed bed after mixing in a mixer with ammonia, the mol ratio of three kinds of gas (vapour) bodies is, toluene vapour: ammonia: air=1: 9: 34, temperature in fixed bed is adjusted to 420 DEG C, pressure is 0.09MPa, add the BN-98 toluene prepared by ammoxidation cyanobenzene catalyzer accounting for gas gross 0.2%, reaction 0.3-0.5 hour, collector is sent into after gas decompression cooling by after reaction, products benzene formonitrile HCN liquid is obtained after condensation, the yield of product is 90%--95%, purity is 99.5%, cyanobenzene is sent into vaporizer vaporize, take vaporizer out of by nitrogen after cyanobenzene vaporization and with mix in a mixer in chlorine laggard enter fluidized-bed, the mol ratio of air input is cyanobenzene vapour: chlorine: nitrogen=2.8: 8: 30, add catalyst activity charcoal simultaneously, quantity is 1.9% of gas gross in bed, temperature in fluidized-bed is adjusted to 220 DEG C, pressure is 0.05MPa, 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, after reaction terminates, mixed gas after reaction in fixed bed is sent into collector, pentachlorobenzonitrile is obtained through condensation post-drying.The yield of this reaction is 80%-95%, and the purity of product is 98%.
Embodiment 6
Quantitative toluene is sent into vaporizer vaporize, take vaporizer out of by air after toluene vaporization and enter fixed bed after mixing in a mixer with ammonia, the mol ratio of three kinds of gas (vapour) bodies is, toluene vapour: ammonia: air=1: 10: 35, temperature in fixed bed is adjusted to 430 DEG C, pressure is 0.10Mpa, add the BN-98 toluene prepared by ammoxidation cyanobenzene catalyzer accounting for gas gross 0.2%, reaction 0.3-0.5 hour, collector is sent into after gas decompression cooling by after reaction, products benzene formonitrile HCN liquid is obtained after condensation, the yield of product is 90%--95%, purity is 99.5%, cyanobenzene is sent into vaporizer vaporize, take vaporizer out of by nitrogen after cyanobenzene vaporization and with mix in a mixer in chlorine laggard enter fluidized-bed, the mol ratio of air input is cyanobenzene vapour: chlorine: nitrogen=3: 9: 36, add catalyst activity charcoal simultaneously, quantity is 2.4% of gas gross in bed, temperature in fluidized-bed is adjusted to 220 DEG C, pressure is 0.06Mpa, 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, after reaction terminates, mixed gas after reaction in fixed bed is sent into collector, pentachlorobenzonitrile is obtained through condensation post-drying.The yield of this reaction is 80%-95%, and the purity of product is 98%.
Claims (3)
1. the production method of a pentachlorobenzonitrile, with toluene, ammonia, oxygen or air, nitrogen, chlorine and the catalyzer selected as required are raw material, it is characterized in that: step one, quantitative toluene is sent into vaporizer vaporize, take vaporizer out of by air after toluene vaporization and enter fixed bed after mixing in a mixer with ammonia, the mol ratio of three kinds of gases is, toluene vapour: ammonia: air=1: 5-10: 30-35, temperature in fixed bed is adjusted to 380 DEG C-430 DEG C, pressure is 0.05MPa-0.10Mpa, add the BN-98 toluene prepared by ammoxidation cyanobenzene catalyzer accounting for gas gross 0.2%, reaction 0.3-0.5 hour, collector is sent into after gas decompression cooling by after reaction, products benzene formonitrile HCN liquid is obtained after condensation, the yield of product is 90%-95%, purity is 99.5%, step 2, cyanobenzene is sent into vaporizer vaporize, take vaporizer out of by nitrogen after cyanobenzene vaporization and with chlorine mix in a mixer laggard enter fluidized-bed, the mol ratio of air input is cyanobenzene vapour: chlorine: nitrogen=2-3: 4-9: 6-36, add catalyst activity charcoal simultaneously, quantity is the 0.2%-8% of gas gross in bed, temperature in fluidized-bed is adjusted to 180 DEG C-220 DEG C, pressure reacts when being 0.01MPa-0.10Mpa, 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, after reaction terminates, mixed gas after reaction in fixed bed is sent into collector, pentachlorobenzonitrile is obtained through condensation post-drying, the yield of this reaction is 80%-95%, the purity of product is 98%.
2. the production method of a kind of pentachlorobenzonitrile according to claim 1, the feature of its claim 1 step one is: when described fixed bed interior reaction temperature is 380 DEG C, and corresponding pressure is 0.05Mpa; When temperature of reaction is 390 DEG C, corresponding pressure is 0.06Mpa; When temperature of reaction is 400 DEG C, corresponding pressure is 0.07Mpa; When temperature of reaction is 410 DEG C, corresponding pressure is 0.08Mpa; When temperature of reaction is 420 DEG C, corresponding pressure is 0.09Mpa; When temperature of reaction is 430 DEG C, corresponding pressure is 0.10Mpa.
3. the production method of a kind of pentachlorobenzonitrile according to claim 1, the feature of its claim 1 step 2 is: when described fluidized-bed and fixed bed interior reaction temperature are 180 DEG C, and corresponding pressure is 0.01Mpa; When temperature of reaction is 190 DEG C, corresponding pressure is 0.02Mpa; When temperature of reaction is 200 DEG C, corresponding pressure is 0.03Mpa; When temperature of reaction is 210 DEG C, corresponding pressure is 0.04Mpa; When temperature of reaction is 220 DEG C, corresponding pressure is 0.05-0.1Mpa.
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| CN107597091B (en) * | 2017-09-25 | 2019-07-19 | 江苏苏利精细化工股份有限公司 | A kind of production method of high-purity Perchlorobenzonitrile |
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 |
| CN1273238A (en) * | 1999-05-07 | 2000-11-15 | 湖南南天实业股份有限公司 | Fixed-bed process for preparing pentachlorophenyl nitrile by catalytic chloration of phenyl nitrile |
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2010
- 2010-09-29 CN CN201010295691.4A patent/CN102432503B/en active Active
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 |
| CN1273238A (en) * | 1999-05-07 | 2000-11-15 | 湖南南天实业股份有限公司 | Fixed-bed process for preparing pentachlorophenyl nitrile by catalytic chloration of phenyl nitrile |
Non-Patent Citations (2)
| Title |
|---|
| BN-98甲苯氨氧化制苯甲腈催化剂工业应用成功;中国石化有机原料科技情报中心站;《石油炼制与化工》;20011231;第32卷(第9期);13 * |
| 甲苯氨氧化合成苯甲腈反应条件的探索;卢晗锋等;《浙江工业大学学报》;20050430;第33卷(第2期);137-140 * |
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