CN102432505A - Production method of tetrachlorophthalonitrile - Google Patents
Production method of tetrachlorophthalonitrile Download PDFInfo
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- CN102432505A CN102432505A CN201010295676XA CN201010295676A CN102432505A CN 102432505 A CN102432505 A CN 102432505A CN 201010295676X A CN201010295676X A CN 201010295676XA CN 201010295676 A CN201010295676 A CN 201010295676A CN 102432505 A CN102432505 A CN 102432505A
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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 make the field, it is characterized in that relating to a kind of working method of tetrachloro phthalonitrile.
Background technology:
Tetrachloro phthalonitrile has another name called the monoethyl dintrile, and outward appearance is a white crystalline powder, and molecular formula is C
8N
2Cl
4, fusing point is 248 ℃-250 ℃.Tetrachloro phthalonitrile is a kind of important organic intermediate, is widely used in fields such as medicine, dyestuff, agricultural chemicals, and purposes is very extensive.The present invention is that (molecular formula is CH with o-Xylol
3C
6H
4CH
3, colourless transparent liquid has aromatic odour, fusing point-25.2 ℃, and 144.4 ℃ of boiling points can be miscible with ethanol, ether, acetone and benzene, water insoluble, and as phthalic anhydride and other organic synthesis raw materials, the mode of producing is generally extracted through certain process from YLENE.) in fluidized-bed, produce phthalonitrile for raw material through ammonia oxygen method, the main points of this working method are: one, select catalyzer for use; Two, will control suitable reaction temperature, temperature plays important effect in the ammonia oxidation strong exothermal reaction, and the optimum temps that experiment showed, this reaction is 320 ℃-440 ℃, and when temperature was higher than 440 ℃, over oxidation took place; Three, the air input of control ammonia, ammonia is considered to cause in the oxidative ammonolysis high reactivity and principal element optionally, experiment showed, that the mole proportioning of the best is an o-Xylol vapour: ammonia: oxygen (or air)=1: 2-18: 8-45; In addition, reaction times and pressure also are the factors of influence reaction, experiment showed, that working as pressure is 0.05Mpa-0.10Mpa, makes phthalonitrile by above-mentioned prescription and technology through fluidized-bed reactor; With the phthalonitrile (phthalonitrile: molecular formula C that makes
8H
1N
2, molecular weight is 128.13, and fusing point is 138 ℃-140 ℃, and outward appearance is a white needle-like crystals, can be used as pigment and fine chemicals midbody.) produce tetrachloro phthalonitrile for raw material through the method for gas phase chlorination, the production main points of this method are: one, select suitable temperature and pressure, 230 ℃-250 ℃ of temperature, the pressure of this reaction of experiment proof is that 0.01MPa-0.10Mpa is best; Two, select suitable air inlet ratio and reaction times, be phthalonitrile vapour through the mole proportioning that facts have proved air input: chlorine: nitrogen=2: 5-10: 10-40 is for best; Three, select appropriate catalyst, produce tetrachloro phthalonitrile through fixed bed again through fluidized-bed earlier by above-mentioned prescription and technology.Advantage of the present invention is: technology is simple, production cost is low, pollution-free, product yield is high and quality good.
Summary of the invention:
In order to overcome the defective that older production technique production cost is high, pollution is big, transformation time is long; The invention provides a kind of is raw material with the o-Xylol, produces phthalonitrile earlier, produces the working method of tetrachloro phthalonitrile again; This method technology is simple, efficient is high; Cost is low, and transformation time is short, pollution-free, can produce qualified tetrachloro phthalonitrile product.
The present invention can realize through following technical scheme:
A kind of method of suitability for industrialized production tetrachloro phthalonitrile is characterized in that being made up of following steps:
1, quantitative o-Xylol being sent into vaporizer vaporizes; O-Xylol vaporization back is taken out of vaporizer and in mixing tank, is mixed the laggard fluidized-bed of going into ammonia by air; The mol ratio of three kinds of gas (vapour) body is toluene vapour: ammonia: oxygen (or air)=1: 2-18: 8-45 is adjusted into 320 ℃-440 ℃ with temperature in the fluidized-bed; Pressure is 0.05Mpa-0.10Mpa, adds the V that accounts for gas volume total amount 0.2%-8% in the reactor drum
2O
5The catalyzer of making effective constituent reacts it, will react and send into collector after back gas is lowered the temperature, and after the condensation oven dry, gets the product phthalonitrile, and the yield of product is 80%-90%, and purity is 99%.
2, phthalonitrile is sent into vaporizer and carries out fusion vaporization, phthalonitrile vaporization back by nitrogen take out of vaporizer and with in mixing tank, mix the laggard fluidized-bed of going in chlorine, the mol ratio of air input is a phthalonitrile vapour: chlorine: nitrogen=2: 5-10: 10-40; Add the catalyst activity charcoal simultaneously; Quantity is the 0.2%-8% of bed internal volume total amount, and it is 0.01MPa-0.10Mpa that temperature in the fluidized-bed is transferred to 230 ℃-280 ℃, pressure, after reaction finishes; To react back gas and send into fixed bed; Keep the temperature and pressure identical, and add and add identical catalyst activity charcoal and the chlorine of fluidized-bed quantity, gas and chlorine behind the first set reaction are reacted again with fluidized-bed; Reacted mixed gas in the fixed bed is sent into collector, and oven dry obtains tetrachloro phthalonitrile after condensation.The yield of this reaction is 85%-95%, and product gas purity is 98%.Chlorine gets into fluidized-bed and fixed bed respectively in this reaction process; Adjust the load of two reactor drums through the quantity of two chlorine of adjustment entering; Thereby reduce the content of Perchlorobenzene; Through practice test, the hexachlorobenzene content that this reaction produces has only 40ppm-100ppm, is significantly less than state specified standards.
Fixed bed interior reaction temperature described in the above-mentioned steps 1 is 320 ℃-440 ℃, and pressure is 0.05Mpa-0.10Mpa
Temperature in the above-mentioned steps 2 in fluidized-bed and the fixed bed is that 230 ℃-280 ℃, pressure are 0.01MPa-0.10Mpa.
The invention has the beneficial effects as follows: providing a kind of is raw material with the o-Xylol; Production technique through ammonia oxygen method, gas phase chlorination method production tetrachloro phthalonitrile; This working method has that technology is simple, efficient is high, and cost is low, and 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 vaporizes; O-Xylol vaporization back is taken out of vaporizer and in mixing tank, is mixed the laggard fluidized-bed of going into ammonia by air; The mol ratio of three kinds of gas (vapour) body is toluene vapour: ammonia: oxygen (or air)=1: 2: 8 is adjusted into 320 ℃ with temperature in the fluidized-bed; Pressure is 0.05Mpa, adds the V that accounts for gas volume total amount 0.2% in the reactor drum
2O
5The catalyzer of making effective constituent reacts it, will react and send into collector after back gas is lowered the temperature, and after the condensation oven dry, gets the product phthalonitrile, and the yield of product is 80%-90%, and purity is 99%; Phthalonitrile is sent into vaporizer carries out fusion vaporization, phthalonitrile vaporization back by nitrogen take out of vaporizer and with in mixing tank, mix the laggard fluidized-bed of going in chlorine, the mol ratio of air input is a phthalonitrile vapour: chlorine: nitrogen=2: 5: 10; Add the catalyst activity charcoal simultaneously; Quantity is 0.2% of bed internal volume total amount, and it is 0.01MPa-0. that temperature in the fluidized-bed is transferred to 230 ℃, pressure, after reaction finishes; To react back gas and send into fixed bed; Keep the temperature and pressure identical, and add and add identical catalyst activity charcoal and the chlorine of fluidized-bed quantity, gas and chlorine behind the first set reaction are reacted again with fluidized-bed; Mixed gas after the reaction in the fixed bed is sent into collector, and oven dry obtains tetrachloro phthalonitrile after condensation.The yield of this reaction is 85%-95%, and product gas purity is 98%.
Embodiment 2
Quantitative o-Xylol is sent into vaporizer vaporizes; O-Xylol vaporization back is taken out of vaporizer and in mixing tank, is mixed the laggard fluidized-bed of going into ammonia by air; The mol ratio of three kinds of gas (vapour) body is toluene vapour: ammonia: oxygen (or air)=1: 5: 15 is adjusted into 340 ℃ with temperature in the fluidized-bed; Pressure is 0.06Mpa, adds the V that accounts for gas volume total amount 1% in the reactor drum
2O
5The catalyzer of making effective constituent reacts it, will react and send into collector after back gas is lowered the temperature, and after the condensation oven dry, gets the product phthalonitrile, and the yield of product is 80%-90%, and purity is 99%.Phthalonitrile is sent into vaporizer carries out fusion vaporization, phthalonitrile vaporization back by nitrogen take out of vaporizer and with in mixing tank, mix the laggard fluidized-bed of going in chlorine, the mol ratio of air input is a phthalonitrile vapour: chlorine: nitrogen=2: 6: 15; Add the catalyst activity charcoal simultaneously; Quantity is 1% of bed internal volume total amount, and it is 0.03MPa that temperature in the fluidized-bed is transferred to 240 ℃, pressure, after reaction finishes; To react back gas and send into fixed bed; Keep the temperature and pressure identical, and add and add identical catalyst activity charcoal and the chlorine of fluidized-bed quantity, gas and chlorine behind the first set reaction are reacted again with fluidized-bed; Mixed gas after the reaction in the fixed bed is sent into collector, and oven dry obtains tetrachloro phthalonitrile after condensation.The yield of this reaction is 85%-95%, and product gas purity is 98%.
Embodiment 3
Quantitative o-Xylol is sent into vaporizer vaporizes; O-Xylol vaporization back is taken out of vaporizer and in mixing tank, is mixed the laggard fluidized-bed of going into ammonia by air; The mol ratio of three kinds of gas (vapour) body is toluene vapour: ammonia: oxygen (or air)=1: 8: 22 is adjusted into 360 ℃ with temperature in the fluidized-bed; Pressure is 0.07Mpa, adds the V that accounts for gas volume total amount 2% in the reactor drum
2O
5The catalyzer of making effective constituent reacts it, will react and send into collector after back gas is lowered the temperature, and after the condensation oven dry, gets the product phthalonitrile, and the yield of product is 80%-90%, and purity is 99%.Phthalonitrile is sent into vaporizer carries out fusion vaporization, phthalonitrile vaporization back by nitrogen take out of vaporizer and with in mixing tank, mix the laggard fluidized-bed of going in chlorine, the mol ratio of air input is a phthalonitrile vapour: chlorine: nitrogen=2: 7: 20; Add the catalyst activity charcoal simultaneously; Quantity is 2% of bed internal volume total amount, and it is 0.05Mpa that temperature in the fluidized-bed is transferred to 250 ℃, pressure, after reaction finishes; To react back gas and send into fixed bed; Keep the temperature and pressure identical, and add and add identical catalyst activity charcoal and the chlorine of fluidized-bed quantity, gas and chlorine behind the first set reaction are reacted again with fluidized-bed; Mixed gas after the reaction in the fixed bed is sent into collector, and oven dry obtains tetrachloro phthalonitrile after condensation.The yield of this reaction is 85%-95%, and product gas purity is 98%.
Embodiment 4
Quantitative o-Xylol is sent into vaporizer vaporizes; O-Xylol vaporization back is taken out of vaporizer and in mixing tank, is mixed the laggard fluidized-bed of going into ammonia by air; The mol ratio of three kinds of gas (vapour) body is toluene vapour: ammonia: oxygen (or air)=1: 11: 29 is adjusted into 380 ℃ with temperature in the fluidized-bed; Pressure is 0.08Mpa, adds the V that accounts for gas volume total amount 3% in the reactor drum
2O
5The catalyzer of making effective constituent reacts it, will react and send into collector after back gas is lowered the temperature, and after the condensation oven dry, gets the product phthalonitrile, and the yield of product is 80%-90%, and purity is 99%.Phthalonitrile is sent into vaporizer carries out fusion vaporization, phthalonitrile vaporization back by nitrogen take out of vaporizer and with in mixing tank, mix the laggard fluidized-bed of going in chlorine, the mol ratio of air input is a phthalonitrile vapour: chlorine: nitrogen=2: 8: 30; Add the catalyst activity charcoal simultaneously; Quantity is 3% of bed internal volume total amount, and it is 0.07Mpa that temperature in the fluidized-bed is transferred to 260 ℃, pressure, after reaction finishes; To react back gas and send into fixed bed; Keep the temperature and pressure identical, and add and add identical catalyst activity charcoal and the chlorine of fluidized-bed quantity, gas and chlorine behind the first set reaction are reacted again with fluidized-bed; Mixed gas after the reaction in the fixed bed is sent into collector, and oven dry obtains tetrachloro phthalonitrile after condensation.The yield of this reaction is 85%-95%, and product gas purity is 98%.
Embodiment 5
Quantitative o-Xylol is sent into vaporizer vaporizes; O-Xylol vaporization back is taken out of vaporizer and in mixing tank, is mixed the laggard fluidized-bed of going into ammonia by air; The mol ratio of three kinds of gas (vapour) body is toluene vapour: ammonia: oxygen (or air)=1: 14: 36 is adjusted into 400 ℃ with temperature in the fluidized-bed; Pressure is 0.09Mpa, adds the V that accounts for gas volume total amount 4% in the reactor drum
2O
5The catalyzer of making effective constituent reacts it, will react and send into collector after back gas is lowered the temperature, and after the condensation oven dry, gets the product phthalonitrile, and the yield of product is 80%-90%, and purity is 99%.Phthalonitrile is sent into vaporizer carries out fusion vaporization, phthalonitrile vaporization back by nitrogen take out of vaporizer and with in mixing tank, mix the laggard fluidized-bed of going in chlorine, the mol ratio of air input is a phthalonitrile vapour: chlorine: nitrogen=2: 9: 35; Add the catalyst activity charcoal simultaneously; Quantity is 4% of bed internal volume total amount, and it is 0.09MPa that temperature in the fluidized-bed is transferred to 270 ℃, pressure, after reaction finishes; To react back gas and send into fixed bed; Keep the temperature and pressure identical, and add and add identical catalyst activity charcoal and the chlorine of fluidized-bed quantity, gas and chlorine behind the first set reaction are reacted again with fluidized-bed; Mixed gas after the reaction in the fixed bed is sent into collector, and oven dry obtains tetrachloro phthalonitrile after condensation.The yield of this reaction is 85%-95%, and product gas purity is 98%.
Embodiment 6
Quantitative o-Xylol is sent into vaporizer vaporizes; O-Xylol vaporization back is taken out of vaporizer and in mixing tank, is mixed the laggard fluidized-bed of going into ammonia by air; The mol ratio of three kinds of gas (vapour) body is toluene vapour: ammonia: oxygen (or air)=1: 18: 45 is adjusted into 440 ℃ with temperature in the fluidized-bed; Pressure is 0.10Mpa, adds the V that accounts for gas volume total amount 5% in the reactor drum
2O
5The catalyzer of making effective constituent reacts it, will react and send into collector after back gas is lowered the temperature, and after the condensation oven dry, gets the product phthalonitrile, and the yield of product is 80%-90%, and purity is 99%.Phthalonitrile is sent into vaporizer carries out fusion vaporization, phthalonitrile vaporization back by nitrogen take out of vaporizer and with in mixing tank, mix the laggard fluidized-bed of going in chlorine, the mol ratio of air input is a phthalonitrile vapour: chlorine: nitrogen=2: 10: 40; Add the catalyst activity charcoal simultaneously; Quantity is 5% of bed internal volume total amount, and it is 0.10Mpa that temperature in the fluidized-bed is transferred to 280 ℃, pressure, after reaction finishes; To react back gas and send into fixed bed; Keep the temperature and pressure identical, and add and add identical catalyst activity charcoal and the chlorine of fluidized-bed quantity, gas and chlorine behind the first set reaction are reacted again with fluidized-bed; Mixed gas after the reaction in the fixed bed is sent into collector, and oven dry obtains tetrachloro phthalonitrile after condensation.The yield of this reaction is 85%-95%, and product gas purity is 98%.
Claims (5)
1. the working method of a tetrachloro phthalonitrile, it is characterized in that: with o-Xylol, ammonia, air or oxygen, chlorine, nitrogen and catalyzer is raw material, obtains finished product through following steps.
2. the working method of a kind of tetrachloro phthalonitrile according to claim 1; The characteristic of its first step is: quantitative o-Xylol is sent into vaporizer vaporize; O-Xylol vaporization back is taken out of vaporizer and in mixing tank, is mixed the laggard fluidized-bed of going into ammonia by air or oxygen; The mol ratio of three kinds of gas (vapour) body is toluene vapour: ammonia: oxygen (or air)=1: 2-18: 8-45 is adjusted into 320 ℃-440 ℃ with temperature in the fluidized-bed; Pressure is 0.05Mpa-0.10Mpa, adds the V that accounts for gas volume total amount 0.2%-8% in the reactor drum
2O
5The catalyzer of making effective constituent reacts it, will react and send into collector after back gas is lowered the temperature, and after the condensation oven dry, gets the product phthalonitrile, and the yield of product is 80%-90%, and purity is 99%.
3. the working method of a kind of tetrachloro phthalonitrile according to claim 1; The characteristic in its second step is: phthalonitrile is sent into vaporizer carries out fusion vaporization, phthalonitrile vaporization back by nitrogen take out of vaporizer and with in mixing tank, mix the laggard fluidized-bed of going in chlorine, the mol ratio of air input is a phthalonitrile vapour: chlorine: nitrogen=2: 5-10: 10-40; Add the catalyst activity charcoal simultaneously; Quantity is the 0.2%-8% of bed internal volume total amount, and it is 0.01MPa-0.10Mpa that temperature in the fluidized-bed is transferred to 230 ℃-280 ℃, pressure, after reaction finishes; To react back gas and send into fixed bed; Keep the temperature and pressure identical, and add and add identical catalyst activity charcoal and the chlorine of fluidized-bed quantity, gas and chlorine behind the first set reaction are reacted again with fluidized-bed; Mixed gas after the reaction in the fixed bed is sent into collector, and oven dry obtains tetrachloro phthalonitrile after condensation.The yield of this reaction is 85%-95%, and product gas purity is 98%.
4. the fixed bed interior reaction temperature described in the aforesaid right requirement 2 is 320 ℃-440 ℃, and pressure is 0.05Mpa-0.10Mpa
5. to require in 3 the temperature in the fluidized-bed and fixed bed be that 230 ℃-280 ℃, pressure are 0.01MPa-0.10Mpa to aforesaid right.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103740125A (en) * | 2014-01-15 | 2014-04-23 | 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 |
| CN109651196A (en) * | 2018-12-27 | 2019-04-19 | 江阴苏利化学股份有限公司 | A kind of technique of the tower rewinding of continuously sublimating of Bravo |
| CN112457214A (en) * | 2019-11-07 | 2021-03-09 | 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 |
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| 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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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103740125A (en) * | 2014-01-15 | 2014-04-23 | 河北铢峰凯美考科技有限公司 | Method for preparing copper phthalocyanine pigments |
| 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 |
| CN109651196A (en) * | 2018-12-27 | 2019-04-19 | 江阴苏利化学股份有限公司 | A kind of technique of the tower rewinding of continuously sublimating of Bravo |
| 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 |
| CN112457214A (en) * | 2019-11-07 | 2021-03-09 | 鞍山七彩化学股份有限公司 | Synthesis method of 4-nitrophthalonitrile |
| 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 |
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