CN101913980A - Production method of 1,1,1,3,3-pentachloropropane - Google Patents
Production method of 1,1,1,3,3-pentachloropropane Download PDFInfo
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- CN101913980A CN101913980A CN2010102738939A CN201010273893A CN101913980A CN 101913980 A CN101913980 A CN 101913980A CN 2010102738939 A CN2010102738939 A CN 2010102738939A CN 201010273893 A CN201010273893 A CN 201010273893A CN 101913980 A CN101913980 A CN 101913980A
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- Prior art keywords
- promotor
- vinylchlorid
- tetracol phenixin
- pentachloropropane
- primary catalysts
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- VVWFZKBKXPXGBH-UHFFFAOYSA-N 1,1,1,3,3-pentachloropropane Chemical compound ClC(Cl)CC(Cl)(Cl)Cl VVWFZKBKXPXGBH-UHFFFAOYSA-N 0.000 title abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 59
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims abstract description 50
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 230000004913 activation Effects 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 claims description 14
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical group CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 claims description 11
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 10
- 238000007701 flash-distillation Methods 0.000 claims description 8
- 239000000463 material Substances 0.000 abstract description 8
- 238000010924 continuous production Methods 0.000 abstract description 5
- 239000007788 liquid Substances 0.000 abstract description 2
- 238000002156 mixing Methods 0.000 abstract description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 8
- 230000003213 activating effect Effects 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 238000001994 activation Methods 0.000 description 21
- 239000007791 liquid phase Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FRCHKSNAZZFGCA-UHFFFAOYSA-N 1,1-dichloro-1-fluoroethane Chemical compound CC(F)(Cl)Cl FRCHKSNAZZFGCA-UHFFFAOYSA-N 0.000 description 1
- YACLCMMBHTUQON-UHFFFAOYSA-N 1-chloro-1-fluoroethane Chemical compound CC(F)Cl YACLCMMBHTUQON-UHFFFAOYSA-N 0.000 description 1
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
- 229940099364 dichlorofluoromethane Drugs 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- -1 hydrocarbons compound Chemical class 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
Images
Classifications
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a production method of 1,1,1,3,3-pentachloropropane (HCC-240fa). The 1,1,1,3,3-pentachloropropane is synthesized by continuously reacting the materials of carbon tetrachloride and chloroethylene in a tubular reactor. The method comprises the steps of firstly mixing the carbon tetrachloride with the chloroethylene and preheating the mixture to a reaction temperature, then introducing the mixture together with a catalyst into the tubular reactor for telomeric reaction, removing the unreacted carbon tetrachloride and chloroethylene through flash evaporation, and then further distilling to obtain the HCC-240fa, wherein the unreacted carbon tetrachloride and chloroethylene are recycled and the catalyst is recycled after being subjected to the activating treatment. The invention adopts the liquid as the activated system and uses the tubular reactor for reaction, thereby ensuring simple and convenient operation as well as continuous production.
Description
Technical field
The present invention relates to a kind of 1,1,1,3, the production method of 3-pentachloropropane, relating in particular to a kind of is raw material with tetracol phenixin and vinylchlorid (VnCl), successive reaction is synthetic 1,1,1,3 in tubular reactor, the production method of 3-pentachloropropane.
Background technology
1,1,1,3,3-pentachloropropane (HCC-240fa) is preparation 1,1,1,3, the intermediate of 3-pentafluoropropane (HFC-245fa).The latent value (ODP) of the atmospheric ozone consumption of HFC-245fa is zero, be a kind of fluorinated hydrocarbons compound, mainly be used as dichloromonofluoromethane (CFC-11) and 1,1 at present atmospheric ozone layer safety, the substitute of 1-chloro fluoroethane (HCFC-141b) is widely used as whipping agent, solvent and clean-out system.
In existing HCC-240fa technology of preparing, industrial main employing tetracol phenixin and vinylchlorid are raw material, under the effect of catalyzer, carry out telomerization and obtain 1,1,1,3, the 3-pentachloropropane in tank reactor.As: US6313360 discloses a kind of continuous production 1,1,1,3, the method for 3-pentachloropropane, this method adopts tank reactor, catalyst system is made up of iron powder, iron trichloride and organophosphate, because telomerization is carried out under certain pressure, iron powder is as solid materials, be difficult for continuous and quantitative and add reaction system, operational difficulty.
Summary of the invention
The objective of the invention is to overcome the deficiency that exists in the background technology, it is liquid that a kind of catalyst system is provided, easy and simple to handle, easy to implement 1,1,1,3, the continuous production method of 3-pentachloropropane.
In order to realize purpose of the present invention, catalyst system of the present invention is by Primary Catalysts, promotor and solvent composition, and wherein Primary Catalysts is FeCl
2, promotor is tributyl phosphate, triethyl phosphate or triethyl-phosphite, solvent is a tetracol phenixin, this catalyst system is a liquid phase, is transported to easily in the telomerization reactor of positive pressure operation, and can accurately measure, make 1,1,1,3, the continuous production of 3-pentachloropropane is easy and simple to handle, easy to implement.Simultaneously, because reaction mass and catalyst system are liquid phase, easily form homogeneous phase, reaction process need not to stir, so telomerization reactor selects tubular reactor for use, has reduced the volume of reactor.
The invention provides a kind of 1,1,1,3, the production method of 3-pentachloropropane, this method comprises:
A, be to mix at 1～10: 1 in molar ratio, and be preheated to 100 ℃～150 ℃ tetracol phenixin and vinylchlorid;
Tetracol phenixin after B, the preheating and vinylchlorid, enter tubular reactor with catalyzer, at reaction pressure 0.3MPa～1.5MPa, 90 ℃～140 ℃ of temperature of reaction, carry out telomerization under the condition of 5 minutes～60 minutes residence time, wherein catalyzer is by Primary Catalysts, promotor and solvent composition, and Primary Catalysts is FeCl
2, promotor is tributyl phosphate, triethyl phosphate or triethyl-phosphite, solvent is tetracol phenixin or telomerization product vinasse;
C, telomerization product remove unreacted tetracol phenixin and vinylchlorid through flash distillation, and unreacted tetracol phenixin and vinylchlorid recycle;
D, the reaction solution that removes behind tetracol phenixin and the vinylchlorid obtain 1,1,1,3 through further distillation, 3-pentachloropropane product and contain the raffinate of Primary Catalysts, promotor.
The described raffinate part discharge system that contains Primary Catalysts, promotor of step D of the present invention, another part adds iron powder and promotor carries out using as catalyst recirculation after the activation treatment to it, and the Primary Catalysts of the consumption of iron powder and promotor and the system of discharge, the amount of promotor are suitable.The material of discharge system is generally 1/20～1/3 of raffinate total amount.
The purpose of catalyst activation mainly is the FeCl that will generate in the reaction process
3Be reduced to FeCl with the Fe powder
2, reply catalytic activity.The catalyst activation process is operated under normal pressure, and the Fe powder quantitatively adds the catalyst activation device easily continuously.
Discover that the effect of promotor tributyl phosphate, triethyl phosphate or triethyl-phosphite not only can improve catalytic activity, the coking phenomenon in all right inhibited reaction liquid still-process.Therefore, the tributyl phosphate that deactivated catalyst of the present invention is used, triethyl phosphate or triethyl-phosphite can directly join in the reaction solution that removes behind tetracol phenixin and the vinylchlorid, the coking in the time of the restock promotor in the inhibited reaction liquid still-process.
The invention provides a kind ofly 1,1,1,3, the preferred version of the production method of 3-pentachloropropane comprises:
A, be to mix at 1～10: 1 in molar ratio, and be preheated to 100 ℃～150 ℃ tetracol phenixin and vinylchlorid;
Tetracol phenixin after B, the preheating and vinylchlorid, enter tubular reactor with catalyzer, at reaction pressure 0.3MPa～1.5MPa, 90 ℃～140 ℃ of temperature of reaction, carry out telomerization under the condition of 5 minutes～60 minutes residence time, wherein catalyzer is by Primary Catalysts, promotor and solvent composition, and Primary Catalysts is that FeCl2, promotor are tributyl phosphate, triethyl phosphate or triethyl-phosphite, and solvent is tetracol phenixin or telomerization product vinasse;
C, telomerization product remove unreacted tetracol phenixin and vinylchlorid through flash distillation, and unreacted tetracol phenixin and vinylchlorid recycle;
D, the reaction solution that removes behind tetracol phenixin and the vinylchlorid obtain 1,1,1,3 through further distillation, 3-pentachloropropane product and contain the raffinate of Primary Catalysts, promotor;
The described raffinate part discharge system that contains Primary Catalysts, promotor of E, step D, another part enters the catalyst activation device;
F, add iron powder and promotor tributyl phosphate, triethyl phosphate or triethyl-phosphite carry out catalyst activation treatment to the catalyst activation device, the amount of Primary Catalysts, promotor that the add-on of iron powder and promotor and step e are discharged system is suitable, and the material after the activation treatment is circulated to tubular reactor.
The invention provides a kind ofly 1,1,1,3, the more preferably scheme of the production method of 3-pentachloropropane comprises:
A, be to mix at 1～10: 1 in molar ratio, and be preheated to 100 ℃～150 ℃ tetracol phenixin and vinylchlorid;
Tetracol phenixin after B, the preheating and vinylchlorid, enter tubular reactor with catalyzer, at reaction pressure 0.3MPa～1.5MPa, 90 ℃～140 ℃ of temperature of reaction, carry out telomerization under the condition of 5 minutes～60 minutes residence time, wherein catalyzer is by Primary Catalysts, promotor and solvent composition, and Primary Catalysts is FeCl
2, promotor is tributyl phosphate, triethyl phosphate or triethyl-phosphite, solvent is tetracol phenixin or telomerization product vinasse;
C, telomerization product remove unreacted tetracol phenixin and vinylchlorid through flash distillation, and unreacted tetracol phenixin and vinylchlorid recycle;
D, remove reaction solution behind tetracol phenixin and the vinylchlorid and additional promotor mixes, enter water distilling apparatus in the lump, obtain 1,1,1,3,3-pentachloropropane product and contain the raffinate of Primary Catalysts, promotor through further distillation;
The described raffinate part discharge system that contains Primary Catalysts, promotor of E, step D, another part enters the catalyst activation device;
F, add iron powder to the catalyst activation device and carry out catalyst activation treatment, the material after the activation treatment is circulated to tubular reactor.
Reaction mass of the present invention and catalyst system are liquid phase, easily form homogeneous phase, and reaction process need not to stir, telomerization in carry out.Under the identical production capacity, volume required 2/3～3/4 of the tank reactor that is about of tubular reactor, this is those skilled in the art's a known technology general knowledge.
The tubular reactor that telomerization is used can be adiabatic tubular reactor and outer heating thermostatic type tubular reactor, preferred adiabatic tubular reactor, the more preferably adiabatic tubular reactor of liner enamel, glass or poly-PTFE.
Catalyzer of the present invention is by Primary Catalysts, promotor and solvent composition, and wherein the mol ratio of Primary Catalysts, promotor and solvent is 1: 1～10: 20～50, and Primary Catalysts is FeCl
2, promotor is tributyl phosphate, triethyl phosphate or triethyl-phosphite, when feeding intake for the first time, solvent is a tetracol phenixin, solvent is a telomerization product vinasse in the operational process continuously.During reaction, the mol ratio of control Primary Catalysts and vinylchlorid is 1: 20～100.
In the telomerization, the material mole proportioning between tetracol phenixin and the vinylchlorid is 1～10, between preferred 1.1～5 generally greater than stoichiometric number.
Change reaction raw materials, of the present invention 1,1,1,3, it is synthetic 1,1,1 that the production method of 3-pentachloropropane is equally applicable to telomerization, 3-tetrachloro propane and 1,1,1,3, the serialization production of 3-pentachloro-butane.
Of the present invention 1,1,1,3, the preparation method of 3-pentachloropropane, compared with prior art, its useful effect is: (1) catalyst system is a liquid phase, be transported to easily in the telomerization reactor of positive pressure operation, and can accurately measure, make continuous production easy and simple to handle, easy to implement; (2) adopt tubular reactor, under the identical production capacity, volume required subtracting.
Description of drawings
Fig. 1,2,3 expressions process flow diagram of the present invention.
Among the figure: 1, mixing of materials device; 2 primary heater units; 3, telomerize tubular reactor; 4, flash distillation plant; 5, water distilling apparatus; 6, catalyst activation device.
Embodiment
It is ∮ 25 * 2.5mm that present embodiment telomerization reactor 4 adopts calibers, 2 meters of length add heat pipe reactor, its technical process is:
A, be to mix at 10: 1 in molar ratio, and be preheated to 150 ℃ tetracol phenixin and vinylchlorid;
Tetracol phenixin after B, the preheating and vinylchlorid enter tubular reactor with catalyzer, and at reaction pressure 1.5MPa, 140 ℃ of temperature of reaction are carried out telomerization under the condition of 5 minutes residence time, and wherein catalyzer is by FeCl
2, tributyl phosphate and tetracol phenixin form FeCl
2, tributyl phosphate and tetracol phenixin mol ratio be 1: 10: 20, FeCl
2With the mol ratio of vinylchlorid be 1: 100;
C, telomerization product remove unreacted tetracol phenixin through flash distillation, and unreacted tetracol phenixin recycles;
D, the reaction solution that removes behind tetracol phenixin and the vinylchlorid obtain 1,1,1,3 through further distillation, 3-pentachloropropane product and contain the raffinate of Primary Catalysts, promotor.
After the present embodiment operation 5 days, the transformation efficiency 100%, 1,1,1,3 of vinylchlorid, the selectivity of 3-pentachloropropane is 98%, distillation make 1,1,1,3, the purity of 3-pentachloropropane is greater than 99.0%.
It is ∮ 25 * 2.5mm that present embodiment telomerization reactor 4 adopts caliber, the adiabatic tubular reactor that length is 2 meters, and its technical process is:
A, be to mix at 1: 1 in molar ratio, and be preheated to 100 ℃ tetracol phenixin and vinylchlorid;
Tetracol phenixin after B, the preheating and vinylchlorid enter tubular reactor with catalyzer, and at reaction pressure 0.3MPa, 90 ℃ of temperature of reaction are carried out telomerization under the condition of 60 minutes residence time, and catalyzer is by FeCl when wherein initial
2, triethyl phosphate and tetracol phenixin form FeCl
2, triethyl phosphate and tetracol phenixin mol ratio be 1: 1: 50, the circulation time catalyzer is by FeCl
2, triethyl phosphate and telomerization product vinasse form; FeCl
2With the mol ratio of vinylchlorid be 1: 20;
C, telomerization product remove unreacted tetracol phenixin and vinylchlorid through flash distillation, and unreacted tetracol phenixin and vinylchlorid recycle;
D, the reaction solution that removes behind tetracol phenixin and the vinylchlorid obtain 1,1,1,3 through further distillation, 3-pentachloropropane product and contain the raffinate of Primary Catalysts, promotor.
The described 1/3 discharge system that contains the raffinate of Primary Catalysts, promotor of E, step D, 2/3 enters the catalyst activation device;
F, add iron powder and triethyl phosphate or carry out catalyst activation treatment to the catalyst activation device, the amount of Primary Catalysts, promotor that the add-on of iron powder and promotor and step e are discharged system is suitable, and the material after the activation treatment is circulated to tubular reactor.
After the present embodiment operation 5 days, the transformation efficiency 99.8%, 1,1,1,3 of vinylchlorid, the selectivity of 3-pentachloropropane is 97.5%, distillation make 1,1,1,3, the purity of 3-pentachloropropane is greater than 99.0%.
It is ∮ 38 * 2.5mm that present embodiment telomerization reactor 4 adopts caliber, the adiabatic tubular reactor of the liner tetrafluoro that length is 2 meters, and its technical process is:
A, be to mix at 1.5: 1 in molar ratio, and be preheated to 130 ℃ tetracol phenixin and vinylchlorid;
Tetracol phenixin after B, the preheating and vinylchlorid enter tubular reactor with catalyzer, 120 ℃ of reaction pressure 0.6MPa temperature of reaction, carry out telomerization under the condition of 30 minutes residence time, and catalyzer is by FeCl when wherein initial
2, triethyl-phosphite and tetracol phenixin form FeCl
2, triethyl phosphate and tetracol phenixin mol ratio be 1: 3: 20, the circulation time catalyzer is by FeCl
2, triethyl-phosphite and telomerization product vinasse form; FeCl
2With the mol ratio of vinylchlorid be 1: 50;
C, telomerization product remove unreacted tetracol phenixin and vinylchlorid through flash distillation, and unreacted tetracol phenixin and vinylchlorid recycle;
D, remove reaction solution behind tetracol phenixin and the vinylchlorid and additional promotor mixes, enter water distilling apparatus in the lump, obtain 1,1,1,3,3-pentachloropropane product and contain the raffinate of Primary Catalysts, promotor through further distillation;
The described raffinate 1/20 discharge system that contains Primary Catalysts, promotor of E, step D, all the other enter the catalyst activation device;
F, add iron powder to the catalyst activation device and carry out catalyst activation treatment, the material after the activation treatment is circulated to tubular reactor.
After the present embodiment operation 5 days, the transformation efficiency 100%, 1,1,1,3 of vinylchlorid, the selectivity of 3-pentachloropropane is 98.5%, distillation make 1,1,1,3, the purity of 3-pentachloropropane is greater than 99.5%.
Claims (4)
1. one kind 1,1,3, the production method of 3-pentachloropropane is characterized in that this method comprises:
A, be to mix at 1～10: 1 in molar ratio, and be preheated to 100 ℃～150 ℃ tetracol phenixin and vinylchlorid;
Tetracol phenixin after B, the preheating and vinylchlorid, enter tubular reactor with catalyzer, at reaction pressure 0.3MPa～1.5MPa, 90 ℃～140 ℃ of temperature of reaction, carry out telomerization under the condition of 5 minutes～60 minutes residence time, wherein catalyzer is by Primary Catalysts, promotor and solvent composition, and Primary Catalysts is FeCl
2, promotor is tributyl phosphate, triethyl phosphate or triethyl-phosphite, solvent is tetracol phenixin or telomerization product vinasse;
C, telomerization product remove unreacted tetracol phenixin and vinylchlorid through flash distillation, and unreacted tetracol phenixin and vinylchlorid recycle;
D, the reaction solution that removes behind tetracol phenixin and the vinylchlorid obtain 1,1,1,3 through further distillation, 3-pentachloropropane product and contain the raffinate of Primary Catalysts, promotor.
2. according to claim 11,1,1,3, the production method of 3-pentachloropropane, it is characterized in that the described raffinate part discharge system that contains Primary Catalysts, promotor of step D, another part adds iron powder and promotor carries out using as catalyst recirculation after the activation treatment to it, and the Primary Catalysts of the consumption of iron powder and promotor and the system of discharge, the amount of promotor are suitable.
3. according to claim 21,1,1,3, the production method of 3-pentachloropropane is characterized in that promotor that activation treatment is used adds in the reaction solution that removes behind tetracol phenixin and the vinylchlorid.
4. according to claim 1,2,3 arbitrary described 1,1,1,3, the production method of 3-pentachloropropane is characterized in that tubular reactor is adiabatic tubular reactor.
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