CN1266045A - Process for preparation of 1,1,1,3,3-pentafluoropropane - Google Patents
Process for preparation of 1,1,1,3,3-pentafluoropropane Download PDFInfo
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- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
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Abstract
A preparation method for 1,1,1,3,3-pentafluoropropane includes the following steps: (1) adding catalyst, fluohydric acid and 1,1,1,3,3-pntachloropropane in a reactor with condensation separator to make fluorination reaction, its reaction temp. is 30-150 deg.C, in the course of reaction adding chlorine gas whose adding quantity is 0.02%-0.06% of dosage of catalyst per hour; (2)feeding the gasified product obtained after separation through the condensation separator into hydrogen chloride separating tower to remove hydrogen chloride gas and make gas phase reaction in fixed bed reactor, its reaction temp. is 150-300 deg.C; (3) after gas phase reaction, adding chlorine gas to the above-mentioned material to make photochlorization reaction. Said invention is high inreeaction efficiency and high in product purity.
Description
The invention belongs to 1,1,1,3, the preparation method of 3-pentafluoropropane particularly uses 1,1,1,3, and the 3-pentachloropropane is through two step of liquid and gas continuous fluorination, preparation 1,1,1,3, the preparation method of 3-pentafluoropropane.
1,1,1,3, the 3-pentafluoropropane can be used as the multiple uses such as whipping agent of clean-out system, cooling agent, urethane industry.Because 1,1,1,3, its ODP value of 3-pentafluoropropane is zero, and atmospheric ozone layer is not had the potential destruction, the life-span in atmosphere is shorter, and the GWP value is 820, and the environmental-protecting performance of each side is all better, is the desirable candidate surrogate of HCFC141b.
About 1,1,1,3, the preparation method of 3-pentafluoropropane, existing many document records mainly contain following four big classes.The first kind telomerizes synthetic 1,1,1,3,3 with tetracol phenixin and vinylidene chloride, 3-chlordene propane, again by 1,1,1,3,3,3-chlordene propane catalytic fluorination synthetic 1,1,1,3,3-five fluoro-3-chloropropanes are at last with 1,1,1,3,3-five fluoro-3-chloropropanes are reduced to 1,1,1,3, the 3-pentafluoropropane is as described in the Chinese invention patent ublic specification of application of publication number CN1128026A; Second class synthesizes 1,1,1,3 by pentachloropropane liquid phase one-step method catalytic fluorination, and the 3-pentafluoropropane is as described in the Chinese invention patent ublic specification of application of publication number CN1130614A; The 3rd class synthesizes 1,1,1 by pentachloropropane in two steps in gas phase, 3,3-pentafluoropropane, the synthetic 1-chloro-3 of the first step elder generation gas phase, 3, the 3-trifluoro propene, second step is by 1-chloro-3,3,3-trifluoro propene gas phase fluorination synthetic 1,1,1,3, the 3-pentafluoropropane is as described in the Chinese invention patent ublic specification of application of publication number CN1206394A; The 4th class the first step gas phase is synthesized 1-chloro-3,3, the 3-trifluoro propene, and second step, the 3-trifluoro propene synthesized 1,1,1,3 in liquid phase by 1-chloro-3,3, and the 3-pentafluoropropane is as described in the Chinese invention patent ublic specification of application of publication number CN166479A.World patent WO 9800378 records 1,1,1,3 get 1,1,1,3 through optical chlorinating reaction after the direct liquid-phase fluorination of 3-pentachloropropane again, the 3-pentafluoropropane, and olefin(e) centent is about the 500PPm in the product.
The object of the present invention is to provide a kind of new production 1,1,1,3, the method for 3-pentafluoropropane, this law can fully be removed the various alkene that reaction generates, and make quality product reach environmental requirement.
The present invention 1,1,1,3, and the preparation method's of 3-pentafluoropropane technical solution is with 1,1,1,3, and 3-pentachloropropane and hydrofluoric acid are made through fluoridation, and its special character is that described fluoridation was carried out liquid phase reaction before this, is to carry out gas-phase reaction again:
1. liquid phase reaction adds catalyzer, hydrofluoric acid and 1,1,1 in being connected with the reactor of condensation separator, 3, the 3-pentachloropropane is carried out fluoridation, and temperature of reaction remains on 30～150 ℃, per hour adds 0.02%～0.06% chlorine of catalyst system therefor weight in the reaction process;
2. after the gasification product introducing hydrogenchloride knockout tower after gas-phase reaction will be separated by condensation separator was removed hydrogen chloride gas, the input fixed-bed reactor carried out gas-phase reaction, and temperature of reaction is 150～300 ℃.
For further removing contained alkene in the purpose product, the material after the described gas-phase reaction after washing, alkali cleaning, is added chlorine and carries out optical chlorinating reaction, material behind the optical chlorinating reaction gets product 1,1,1 after washing, alkali cleaning, drying, fractionation, 3, the 3-pentafluoropropane.
The used catalyzer of liquid phase reaction of the present invention has Primary Catalysts and promotor, and Primary Catalysts is the mixture of antimony pentachloride or butter of antimony and antimony pentachloride, and promotor is chlorsulfonic acid or fluosulfonic acid.
The used catalyzer of gas-phase reaction of the present invention is the mixture of aluminum fluoride and chromium hydroxide.
The present invention makes described liquid phase reaction under hydrofluoric acid is excessive, and 1,1,1,3, the mol ratio of 3-pentachloropropane and hydrofluoric acid is 1: 6.0～9.0, preferred mol ratio is 1: 7.0～8.5.
The preferred temperature of described liquid phase reaction is 50～135 ℃, and the preferred temperature of gas-phase reaction is 180～250 ℃.
The present invention requires to make fluoridation with anhydrous hydrofluoric acid, and the content of sulphur should be less than 100PPm in the hydrofluoric acid, the high inactivation that can accelerate catalyzer of sulphur content, and this inactivation is non-renewable.
1. go on foot in the liquid phase reaction 1,1,1,3,3-pentachloropropane and hydrofluoric acid reaction generate 1,1,1,3, in the time of the 3-pentafluoropropane, generate some intermediate products, material enters condensation separator that reactor connects, through separating, make the high relatively intermediate product of unreacted raw material and boiling point be back to reactor and continue reaction, product 1,1,1,3, the relative low intermediate product 1,1,1 of 3-pentafluoropropane with boiling point, 3-tetrafluoro-3-chloropropane, 1,1,1, the 3-tetrafluoeopropene, 1-chloro-3,3,3-trifluoro propene and byproduct hydrogen chloride, hydrogen fluoride, chlorine etc. are gas process hydrogenchloride knockout tower together except that behind the de-chlorine hydride, enter fixed-bed reactor and carry out and 2. go on foot gas-phase reaction, at 1,1 of this relatively small amount, 1,3-tetrafluoro-3-chloropropane, 1,1,1, the 3-tetrafluoeopropene, 1-chloro-3,3, the 3-trifluoro propene is further fluoridized and is become 1,1, and 1,3, the 3-pentafluoropropane.Sampling analysis shows, through 2. go on foot gas-phase reaction after, product 1,1,1,3, the alkene total content is less than 100PPm in the 3-pentafluoropropane.
Be further to reduce olefin(e) centent in the product, can 2. go on foot after the gas-phase reaction material with the and introduce the optical chlorinating reaction device and carry out optical chlorinating reaction.In the optical chlorinating reaction in chlorine dosage and the material mol ratio of alkene total amount be 1: 1.0～10.0, temperature of reaction is 15～80 ℃, preferred 40～50 ℃.Behind the optical chlorinating reaction, the alkene total content is less than 10PPm in the product, and crude product is after fractionation 1,1,1,3, and 3-pentafluoropropane purity reaches more than 99.5%.
In described liquid phase reaction, the temperature that should control condensation separator is 20～40 ℃, and control makes the pressure of reactor remain on 0.5～2.0Mpa by the release rate of the gasification product of condensation separator.
The present invention is owing to adopt the reactor that is connected with condensation separator, with 1,1,1,3,3-pentachloropropane and hydrofluoric acid are made liquid phase reaction, material is separated through the condensation separator continuous backflow, gaseous product reacts under fixed bed gas-solid phase mode again, makes some intermediate products further fluoridize into the purpose product, reduces olefin(e) centent in the product, improve product purity, so the present invention can extract high-purity product continuously in reaction process, and make and keep higher reactant concn in the Liquid-phase reactor always, reaction is carried out fast.After described gas-phase reaction, carry out the present invention of optical chlorinating reaction, then can further reduce olefin(e) centent in the product, product purity is further improved.
Below in detail the way state embodiments of the present invention.
Embodiment 1 is in the volume that is connected with condensation separator is 5 liters liquid phase reaction still, the adding mol ratio is 1: 1 liquid catalyst antimony pentachloride and chlorsulfonic acid mixture 400 grams, anhydrous hydrofluoric acid 300 grams, reactor slowly is warmed up to 50 ℃, be incubated 2 hours, under this temperature, press per hour 600 grams 1,1,1,3, the speed of 3-pentachloropropane and 500 gram anhydrous hydrofluoric acids adds reactor, keeping temperature of reaction is 50 ℃, feeds chlorine off and on the speed of 4 grams per hour simultaneously, and the temperature of control condensation separator is 40 ℃, and the discharging speed of control gasification product, reactor pressure is maintained in the 2Mpa.The gaseous product of drawing after the liquid phase reaction is through the sampling of hydrogenchloride knockout tower dehydrochlorination gas material this moment, and the sampling thing the results are shown in Table 1 through washing, alkali cleaning post analysis.Material behind the dehydrochlorination enters the preheater of gas-phase reaction through snubber, preheating temperature is 180 ℃, material enters fixed-bed reactor after the preheating, the gas-phase reaction temperature is 250 ℃, the residence time is 5～30 seconds, the sampling of resultant of reaction material, sample stratographic analysis after washing, alkali cleaning the results are shown in Table 2.Material after the gas-phase reaction carries out optical chlorinating reaction after washing, alkali cleaning.Optical chlorinating reaction carries out (as reactors such as white a kind of jade porcelain reactor, inner liner polytetrafluoroethylene, polypropylene) in anticorrosion reactor.Light source adopts 2 of 40 watts of common fluorescent tubes, frequency of light wave is 200～800 nanometers, reaction mass residence time in reactor is 10～30 seconds, temperature of reaction is 15 ℃, and chlorine feeding amount is per hour 0.04 liter, and material obtains high purity product 1 behind the optical chlorinating reaction after washing, alkali cleaning, drying, fractionation, 1,1,3, the 3-pentafluoropropane.Sample the results are shown in Table 3 through washing, alkali cleaning post analysis after the light chlorination.
Implementation column 2 is compared with example 1, the liquid phase reaction temperature change is 60 ℃, the gas-phase reaction temperature change is 240 ℃, and the optical chlorinating reaction temperature change is 25 ℃, per hour feed 1,1,1,3, the weight of 3-pentachloropropane and anhydrous hydrofluoric acid is respectively 600 grams and 470 grams, per hour feed 0.04 liter in chlorine, other reaction conditions is identical with example 1.Result behind liquid phase reaction, gas-phase reaction, the optical chlorinating reaction sees Table 1 respectively, table 2, table 3.
Embodiment 3 compares with example 1, the liquid phase reaction temperature change is 70 ℃, the gas-phase reaction temperature change is 230 ℃, and the optical chlorinating reaction temperature change is 35 ℃, per hour feed 1,1,1,3, the weight of 3-pentachloropropane and anhydrous hydrofluoric acid is respectively 600 grams and 440 grams, per hour feed 0.04 liter in chlorine, other reaction conditions is identical with example 1.Result behind liquid phase reaction, gas-phase reaction, the optical chlorinating reaction sees Table 1 respectively, table 2, table 3.
Embodiment 4 compares with example 1, the liquid phase reaction temperature change is 85 ℃, the gas-phase reaction temperature change is 220 ℃, and the optical chlorinating reaction temperature change is 45 ℃, per hour feed 1,1,1,3, the weight of 3-pentachloropropane and anhydrous hydrofluoric acid is respectively 600 grams and 400 grams, per hour feed 0.04 liter in chlorine, other reaction conditions is identical with example 1.Result behind liquid phase reaction, gas-phase reaction, the optical chlorinating reaction sees Table 1 respectively, table 2, table 3.
Embodiment 5 compares with example 1, the liquid phase reaction temperature change is 100 ℃, the gas-phase reaction temperature change is 210 ℃, and the optical chlorinating reaction temperature change is 55 ℃, per hour feed 1,1,1,3, the weight of 3-pentachloropropane and anhydrous hydrofluoric acid is respectively 600 grams and 370 grams, per hour feed 0.06 liter in chlorine, other reaction conditions is identical with example 1.Result behind liquid phase reaction, gas-phase reaction, the optical chlorinating reaction sees Table 1 respectively, table 2, table 3.
Embodiment 6 compares with example 1, the liquid phase reaction temperature change is 120 ℃, the gas-phase reaction temperature change is 200 ℃, and the optical chlorinating reaction temperature change is 65 ℃, per hour feed 1,1,1,3, the weight of 3-pentachloropropane and anhydrous hydrofluoric acid is respectively 600 grams and 335 grams, per hour feed 0.06 liter in chlorine, other reaction conditions is identical with example 1.Result behind liquid phase reaction, gas-phase reaction, the optical chlorinating reaction sees Table 1 respectively, table 2, table 3.
Embodiment 7 compares with example 1, the liquid phase reaction temperature change is 85 ℃, and the gas-phase reaction temperature change is 210 ℃, and the optical chlorinating reaction temperature change is 15 ℃, per hour feed 1,1,1,3, the weight of 3-pentachloropropane and anhydrous hydrofluoric acid is respectively 600 grams and 400 grams, per hour feed 0.04 liter in chlorine, the adding mol ratio is 1: 1 liquid catalyst antimony pentachloride and fluosulfonic acid mixture 400 grams in the liquid phase reaction still, and other reaction conditions is identical with example 1.Result behind liquid phase reaction, gas-phase reaction, the optical chlorinating reaction sees Table 1 respectively, table 2, table 3.
Embodiment 8 compares with example 1, the liquid phase reaction temperature change is 95 ℃, and the gas-phase reaction temperature change is 220 ℃, and the optical chlorinating reaction temperature change is 15 ℃, per hour feed 1,1,1,3, the weight of 3-pentachloropropane and anhydrous hydrofluoric acid is respectively 600 grams and 470 grams, per hour feed 0.04 liter in chlorine, the adding mol ratio is 1: 1 liquid catalyst antimony pentachloride and fluosulfonic acid mixture 400 grams in the liquid phase reaction still, and other reaction conditions is identical with example 1.Result behind liquid phase reaction, gas-phase reaction, the optical chlorinating reaction sees Table 1 respectively, table 2, table 3.
Result after table 1 liquid phase reaction
| Component | Example 1 | Example 2 | Example 3 | Example 4 | Example 5 | Example 6 | Example 7 | Example 8 |
| 1,1,1,3,3-pentafluoropropane (weight %) | 80.340 | ?82.455 | ?83.250 | ?87.560 | ?92.462 | ?92.552 | ?87.684 | ?90.546 |
| 1,1,1,3-tetrafluoro-3-chloropropane (weight %) | 16.100 | ?14.285 | ?14.040 | ?10.148 | ?5.450 | ?5.480 | ?9.569 | ?6.864 |
| 1,1,1,3-tetrafluoeopropene (weight %) | 2.400 | ?2.260 | ?2.050 | ?1.469 | ?1.258 | ?1.162 | ?1.564 | ?1.648 |
| 1-chloro-3,3,3-trifluoro propene (weight %) | 1.160 | ?1.000 | ?0.660 | ?0.823 | ?0.830 | ?0.806 | ?1.183 | ?0.942 |
Result after table 2 gas-phase reaction
| Component | Example 1 | Example 2 | Example 3 | Example 4 | Example 5 | Example 6 | Example 7 | Example 8 |
| 1,1,1,3,3-pentafluoropropane (weight %) | 99.241 | ?99.200 | ?99.123 | ?99.156 | ?99.000 | ?98.985 | ?99.036 | ?99.152 |
| 1,1,1,3-tetrafluoro-3-chloropropane (weight %) | 0.451 | ?0.350 | ?0.621 | ?0.562 | ?0.800 | ?0.762 | ?0.531 | ?0.426 |
| 1,1,1,3-tetrafluoeopropene (weight %) | 0.004 | ?0.005 | ?0.004 | ?0.005 | ?0.006 | ?0.003 | ?0.004 | ?0.006 |
| 1-chloro-3,3,3-trifluoro propene (weight %) | 0.004 | ?0.004 | ?0.004 | ?0.005 | ?0.004 | ?0.006 | ?0.004 | ?0.004 |
| Other product (weight %) | 0.300 | ?0.441 | ?0.248 | ?0.272 | ?0.190 | ?0.244 | ?0.425 | ?0.412 |
Result behind table 3 optical chlorinating reaction
| Component | Example 1 | Example 2 | Example 3 | Example 4 | Example 5 | Example 6 | Example 7 | Example 8 |
| 1,1,1,3,3-pentafluoropropane (weight %) | 99.042 | ?99.114 | ?99.058 | ?99.140 | ?98.928 | ?98.996 | ?98.940 | ?99.098 |
| 1,1,1,3-tetrafluoro-3-chloropropane (weight %) | 0.448 | ?0.325 | ?0.653 | ?0.556 | ?0.786 | ?0.722 | ?0.505 | ?0.400 |
| 1,1,1,3-tetrafluoeopropene (PPm) | 3 | ?4 | ?5 | ?4 | ?6 | ?2 | ?1 | ?5 |
| 1-chloro-3,3,3-trifluoro propene (PPm) | 5 | ?5 | ?4 | ?4 | ?5 | ?4 | ?3 | ?4 |
| Other product (weight %) | 0.510 | ?0.561 | ?0.289 | ?0.304 | ?0.286 | ?0.282 | ?0.555 | ?0.502 |
Claims (10)
1,1,1,1,3, the preparation method of 3-pentafluoropropane, with 1,1,1,3,3-pentachloropropane and hydrofluoric acid are made through fluoridation, it is characterized in that described fluoridation carried out liquid phase reaction before this, are to carry out gas-phase reaction again:
1. liquid phase reaction adds catalyzer, hydrofluoric acid and 1,1,1 in being connected with the reactor of condensation separator, 3, the 3-pentachloropropane is carried out fluoridation, and temperature of reaction remains on 30～150 ℃, per hour adds 0.02%～0.06% chlorine of catalyst system therefor weight in the reaction process;
2. after the gasification product introducing hydrogenchloride knockout tower after gas-phase reaction will be separated by condensation separator was removed hydrogen chloride gas, the input fixed-bed reactor carried out gas-phase reaction, and temperature of reaction is 150～300 ℃.
2, as claimed in claim 11,1,1,3, the preparation method of 3-pentafluoropropane, it is characterized in that the material after the described gas-phase reaction adding chlorine and carrying out optical chlorinating reaction after washing, alkali cleaning, the material behind the optical chlorinating reaction gets product 1 after washing, alkali cleaning, drying, fractionation, 1,1,3, the 3-pentafluoropropane.
3, as claimed in claim 1 or 21,1,1,3, the preparation method of 3-pentafluoropropane is characterized in that the used catalyzer of liquid phase reaction has Primary Catalysts and promotor, Primary Catalysts is the mixture of antimony pentachloride or butter of antimony and antimony pentachloride, and promotor is chlorsulfonic acid or fluosulfonic acid.
4, as claimed in claim 1 or 21,1,1,3, the preparation method of 3-pentafluoropropane is characterized in that the used catalyzer of gas-phase reaction is the mixture of aluminum fluoride and chromium hydroxide.
5, as claimed in claim 1 or 21,1,1,3, the preparation method of 3-pentafluoropropane is characterized in that liquid phase reaction 1,1,1,3, and the mol ratio of 3-pentachloropropane and hydrofluoric acid is 1: 6.0～9.0.
6, as claimed in claim 51,1,1,3, the preparation method of 3-pentafluoropropane, the mol ratio that it is characterized in that pentachloropropane and hydrofluoric acid is 1: 7.0～8.5.
7, as claimed in claim 1 or 21,1,1,3, the preparation method of 3-pentafluoropropane is characterized in that described liquid reactive temperature is 50～135 ℃, and the temperature of gas-phase reaction is 180～250 ℃.
8, as claimed in claim 1 or 21,1,1,3, the preparation method of 3-pentafluoropropane is characterized in that described condensation separator separation is meant unreacted 1,1,1,3, the 3-pentachloropropane, hydrofluoric acid, the high relatively intermediate product of boiling point that catalyzer and reaction generate is back to reactor, the reaction product 1,1 of the gasification that boiling point is low relatively, 1,3, the 3-pentafluoropropane, hydrogenchloride, 1 of hydrogen fluoride and relatively small amount, 1,1,3,-tetrafluoro-3-chloropropane, 1,1,1,3-tetrafluoeopropene and 1-chloro-3,3, the 3-trifluoro propene, chlorine is gas together and enters the hydrogenchloride knockout tower, after removing hydrogen chloride gas, the input fixed-bed reactor make 1 of relatively small amount, 1,1,3-tetrafluoro-3-chloropropane, 1,1,1,3-tetrafluoeopropene and 1-chloro-3, it is 1,1 that 3,3 trifluoro propenes are further fluoridized, 1,3, the 3-pentafluoropropane.
9, as claimed in claim 81,1,1,3, the preparation method of 3-pentafluoropropane, the temperature that it is characterized in that controlling condensation separator is 20～60 ℃, and control makes the pressure of reactor remain on 0.5～2.0MPa by the release rate of the gasification product of condensation separator.
10, as claimed in claim 21,1,1,3, the preparation method of 3-pentafluoropropane is characterized in that the total mol ratio of chlorine and alkene is 1.0～10.0: 1 in the described optical chlorinating reaction, and the optical chlorinating reaction temperature is 15～80 ℃.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102924226A (en) * | 2012-10-29 | 2013-02-13 | 浙江巍华化工有限公司 | Industrial method for continuous fluorination synthesis of benzotrifluoride product |
| CN103214342A (en) * | 2013-03-29 | 2013-07-24 | 浙江衢化氟化学有限公司 | Synthetic method of 1,1,1,3,3-perfluoropropane |
| CN105399598A (en) * | 2015-11-23 | 2016-03-16 | 淄博澳宏化工科技有限公司 | 1,1,1,3,3-perfluoropropane preparation device and preparation method |
| CN117886665A (en) * | 2023-12-11 | 2024-04-16 | 江西中欣埃克盛新材料有限公司 | Full-flow continuous process for synthesizing 1, 3-pentafluoropropane |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3818398B2 (en) * | 1995-12-29 | 2006-09-06 | ダイキン工業株式会社 | Process for producing 1,1,1,3,3-pentafluoropropane |
| JP4105232B2 (en) * | 1996-06-28 | 2008-06-25 | ザ ユニバーシティ オブ サザン ミシシッピ リサーチ ファンデーション | Ester mixture and method of using the same |
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2000
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102924226A (en) * | 2012-10-29 | 2013-02-13 | 浙江巍华化工有限公司 | Industrial method for continuous fluorination synthesis of benzotrifluoride product |
| CN102924226B (en) * | 2012-10-29 | 2015-05-27 | 浙江巍华化工有限公司 | Industrial method for continuous fluorination synthesis of benzotrifluoride product |
| CN103214342A (en) * | 2013-03-29 | 2013-07-24 | 浙江衢化氟化学有限公司 | Synthetic method of 1,1,1,3,3-perfluoropropane |
| CN103214342B (en) * | 2013-03-29 | 2015-07-08 | 浙江衢化氟化学有限公司 | Synthetic method of 1,1,1,3,3-perfluoropropane |
| CN105399598A (en) * | 2015-11-23 | 2016-03-16 | 淄博澳宏化工科技有限公司 | 1,1,1,3,3-perfluoropropane preparation device and preparation method |
| CN117886665A (en) * | 2023-12-11 | 2024-04-16 | 江西中欣埃克盛新材料有限公司 | Full-flow continuous process for synthesizing 1, 3-pentafluoropropane |
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| CN1120826C (en) | 2003-09-10 |
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