WO2016019718A1 - 一种制备2-氯-1,1,1,2-四氟丙烷的方法 - Google Patents

一种制备2-氯-1,1,1,2-四氟丙烷的方法 Download PDF

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WO2016019718A1
WO2016019718A1 PCT/CN2015/072306 CN2015072306W WO2016019718A1 WO 2016019718 A1 WO2016019718 A1 WO 2016019718A1 CN 2015072306 W CN2015072306 W CN 2015072306W WO 2016019718 A1 WO2016019718 A1 WO 2016019718A1
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chloro
hcfc
tetrafluoropropane
metal halide
reaction
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吕剑
曾纪珺
张伟
韩升
唐晓博
郝志军
亢建平
杨志强
吕婧
王博
李凤仙
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西安近代化学研究所
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
    • C07C17/087—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated halogenated hydrocarbons
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B01J27/08—Halides
    • B01J27/10—Chlorides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B01J27/08—Halides
    • B01J27/12—Fluorides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
    • C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine

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  • the present invention relates to a process for the preparation of 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb), in particular to a metal halide and perfluorosulfonic acid as a catalyst, 2-chloro-3,3
  • HCFC-244bb 2-chloro-1,1,1,2-tetrafluoropropane
  • 2-chloro-3,3 A method for preparing 2-chloro-1,1,1,2-tetrafluoropropane by liquid phase fluorination of 3-trifluoropropene (HCFC-1233xf) with hydrogen fluoride.
  • HFO-1234yf 2,3,3,3-tetrafluoropropene
  • HFO-1234yf has an ozone depletion potential of zero, a greenhouse effect potential of 4, and excellent environmental performance. It is considered to be an ideal substitute for 1,1,1,2-tetrafluoroethane (HFC-134a).
  • Cide patent CN101492342 A discloses a method for synthesizing HCFC-244bb by liquid phase fluorination using hydrogen fluoride and 2-chloro-3,3,3-trifluoropropene (HCFC-1233xf) as a catalyst, which uses SbCl 5 as a catalyst.
  • the reaction temperature was 78 ° C ⁇ 91 ° C, the content of HCFC-244bb in the organic product collected after 71 h reaction was only 82.87%.
  • Chinese patent CN101607865 A discloses a method for preparing HCFC-244bb, which uses a mixture of SbCl 5 and SbCl 3 as a catalyst, and liquid phase fluorination of HCFC-1233xf to synthesize HCFC-244bb at a reaction temperature of 86 ° C to 103 ° C. After running for 129 h, the selectivity of HCFC-244bb was 57% to 98%.
  • Sb 5+ is easily converted into inactive Sb due to poor stability of the SbCl 5 catalyst. 3+ , therefore, in order to maintain the activity of the catalyst, the catalyst is subjected to oxidation treatment by introducing chlorine gas every 4 hours or so during the reaction.
  • the object of the present invention is to overcome the deficiencies in the prior art, and to provide a preparation of 2-chloro-1,1,1,2-tetrafluoropropane with high reaction selectivity, no need to pass chlorine gas in the reaction process, and long service life of the catalyst. method.
  • the technical scheme adopted by the present invention is: liquid phase fluorination of 2-chloro-3,3,3-trifluoropropene with hydrogen fluoride to synthesize 2-chlorochloride using metal halide and perfluorosulfonic acid as catalysts -1,1,1,2-tetrafluoropropane.
  • the metal halide is SbCl 5 , TiCl 4 , SnCl 4 , NbCl 5 , TaCl 5 , SbF 5 , SbCl 2 F 3 , TiF 4 , SnF 4 , NbF 5 or TaF 5
  • the perfluorosulfonic acid is FSO 3 H, CF.
  • the metal halide is preferably SbCl 5 , SbF 5 or SbCl 2 F 3
  • the perfluorosulfonic acid is preferably FSO 3 H
  • the molar ratio of the metal halide to the perfluorosulfonic acid is preferably 1:1 to 5.
  • the reaction is carried out in an atmosphere of HF.
  • the metal halide in the catalyst Prior to the reaction, is fluorinated to the corresponding fluoride or fluorochloride using HF; the corresponding metal fluoride or fluorochloride may also be added directly.
  • a metal fluoride or a fluorochloride and perfluorosulfonic acid catalyst is used to prepare HCFC-244bb by liquid phase fluorination of HCFC-1233xf.
  • the perfluorosulfonic acid can be directly used as a perfluorosulfonic acid of a commercial product, or can be obtained by treating the corresponding chlorine or brominesulfonic acid by HF.
  • the process for preparing HCFC-244bb of the present invention can be carried out batchwise or continuously.
  • HF and HCFC-1233xf are added to the reactor at one time and raised to the corresponding reaction temperature.
  • the preferred reaction conditions are a molar ratio of metal halide to perfluorosulfonic acid of 1:0.1 to 10, HCFC-1233xf.
  • the molar ratio to HF is 1:5 to 30, the molar ratio of HCFC-1233xf to metal halide is 0.5 to 5:1, the reaction temperature is 25 to 150 ° C, and the reaction time is 0.5 to 10 hours.
  • HF and HCFC-1233xf continuously enter the reactor.
  • the preferred reaction conditions are: the molar ratio of metal halide to perfluorosulfonic acid is 1:1 to 5, and the molar ratio of HCFC-1233xf to HF is 1: 1 to 5, the molar ratio of HCFC-1233xf to metal halide is 0.1 to 1:1, and the reaction temperature is 35 to 100 °C.
  • the metal ions in the metal halide are degraded due to the valence state. Low results in a decrease in catalyst activity, which can be regenerated by chlorine gas in the catalyst to restore catalytic activity.
  • the organic materials in the reaction system are first drained, and then chlorine gas and HF are introduced at 50 ° C to 150 ° C for regeneration.
  • reaction selectivity is high, and chlorine gas is not required in the reaction process, and chlorine gas chloride HCFC-1233xf is prevented from generating 2,2,3-trichloro-1,1,1-trifluoropropane and 2,3-dichloro- By-products such as 3,3,3-trifluoropropene, the reaction selectivity is 95.2%, and the highest can reach 99.5%;
  • the activity of the liquid phase fluorination catalyst is stable, and no chlorine gas is required to maintain the activity of the catalyst during the reaction.
  • the HCFC-1233xf conversion rate is above 90.0% and the HCFC-244bb selectivity is above 98.2% during continuous operation for 900 hours;
  • the activity can be recovered after the regeneration treatment.
  • HCFC-244bb was synthesized by batch liquid phase fluorination. Into a 250 mL stainless steel autoclave, 25 g of SbCl 5 , 20.8 g of FSO 3 H, and then 35 g of HF were added for fluorination treatment, and the generated HCl was removed in time to control the pressure within 0.25 MPa. The temperature was raised to 60 ° C, the temperature was kept at 1 h, and the treatment process was completed.
  • HCFC-244bb was synthesized by continuous liquid phase fluorination.
  • 500 g of SbCl 5 , 500 g of FSO 3 H, 660 g of HF were successively introduced, and the generated HCl was removed in time, the control pressure was not more than 0.25 MPa, the temperature was raised to 60 ° C, and the temperature was maintained for 2 h.
  • HCFC-1233xf and HF were continuously transported to the reactor through a metering pump.
  • the feed rate of HCFC-1233xf was 43.5 g/h, the feed rate of HF was 20 g/h, and the amount of HCFC-1233xf charged with SbCl 5
  • the molar ratio was 0.2:1
  • the reaction temperature was 58 ° C to 63 ° C, and the reaction results are shown in Table 3. It can be seen from Table 3 that the HCFC-1233xf conversion rate is maintained between 90.0%-95.2% and the HCFC-244bb selectivity is above 98.2% within 900 hours of continuous operation. Compared with the literature, it is not necessary to pass chlorine gas catalyst during the reaction. Very good stability.
  • Example 22 When the operation of Example 22 was carried out for 1010 hours, the reaction was stopped, the organic materials were drained, chlorine gas and HF were introduced at 60 ° C, and treated for 72 hours, the temperature was lowered, and the chlorine gas and hydrogen chloride in the reaction vessel were drained to complete the catalyst regeneration treatment.
  • the reactor was charged with 660 g of HF, and then HCFC-1233xf and HF were continuously fed to the reactor by means of a metering pump.
  • the feed rate of HCFC-1233xf was 43.7 g/h, and the feed rate of HF was 20.2 g/h.
  • the molar ratio of HCFC-1233xf to SbCl 5 was 0.2:1, and the reaction temperature was 58 ° C to 63 ° C.
  • the reaction results are shown in Table 4. It can be seen from Table 4 that the activity of the catalyst after regeneration is slightly increased during the continuous operation of the test for 520 h.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

本发明公开了一种制备2-氯-1,1,1,2-四氟丙烷的方法，该方法以2-氯-3,3,3-三氟丙烯为原料，包括以下步骤：以金属卤化物和全氟磺酸为催化剂，2-氯-3,3,3-三氟丙烯与氟化氢液相氟化合成2-氯-1,1,1,2-四氟丙烷；其中金属卤化物为SbCl5、TiCl4、SnCl4、NbCl5、TaCl5、SbF5、SbCl2F3、TiF4、SnF4、NbF5或TaF5，全氟磺酸为FSO3H、CF3SO3H、C2F5SO3H或C4F9SO3H，金属卤化物与全氟磺酸的摩尔比为1:0.1～10，HCFC-1233xf与HF的摩尔比为1:1～30，反应温度为25℃～150℃。本发明中制备2-氯-1,1,1,2-四氟丙烷的方法具有反应选择性高、反应过程无需通入氯气、催化剂使用寿命长等优点。本发明用于2-氯-1,1,1,2-四氟丙烷的制备。

Description

一种制备2-氯-1,1,1,2-四氟丙烷的方法 技术领域
本发明涉及一种制备2-氯-1,1,1,2-四氟丙烷(HCFC-244bb)的方法，尤其涉及以金属卤化物和全氟磺酸为催化剂，2-氯-3,3,3-三氟丙烯(HCFC-1233xf)与氟化氢液相氟化制备2-氯-1,1,1,2-四氟丙烷的方法。
背景技术
2-氯-1,1,1,2-四氟丙烷是合成2,3,3,3-四氟丙烯(HFO-1234yf)的原料。HFO-1234yf的臭氧损耗潜值为零，温室效应潜值为4，具有优良的环境性能，被认为是1,1,1,2-四氟乙烷(HFC-134a)的理想替代品。
中国专利CN101492342 A公开了一种以氟化氢和2-氯-3,3,3-三氟丙烯(HCFC-1233xf)为原料液相氟化合成HCFC-244bb的方法，该方法采用SbCl5作为催化剂，反应温度为78℃～91℃，反应71h后收集的有机产物中HCFC-244bb含量仅有82.87％。中国专利CN101607865 A公开了一种制备HCFC-244bb的方法，该方法以SbCl5和SbCl3的混合物为催化剂，液相氟化HCFC-1233xf合成HCFC-244bb，反应温度为86℃～103℃，反应运行129h，HCFC-244bb的选择性为57％～98％。上述反应中，为避免副产物特别是氯化产物的生成对分离的影响，寻求更高的选择性是关键，同时由于SbCl5催化剂的稳定性较差，Sb5+易转变为无活性的Sb3+，因此，为了保持催化剂活性，反应过程中需每4h左右通入氯气对催化剂进行氧化处理。
发明内容
本发明的目的在于克服背景技术中存在的不足，提供一种反应选择性高、反应过程无需通入氯气、催化剂使用寿命长的制备2-氯-1,1,1,2-四氟丙烷的方法。
为了实现本发明的目的，本发明采用的技术方案为：以金属卤化物和全氟磺酸为催化剂，2-氯-3,3,3-三氟丙烯与氟化氢液相氟化合成2-氯-1,1,1,2-四氟丙烷。其中金属卤化物为SbCl5、TiCl4、SnCl4、NbCl5、TaCl5、SbF5、SbCl2F3、TiF4、SnF4、NbF5或TaF5，全氟磺酸为FSO3H、CF3SO3H、C2F5SO3H或C4F9SO3H，金属卤化物与全氟磺酸的摩尔比为1:0.1～10，HCFC-1233xf与HF的摩尔比为1:1～30，反应温度为25℃～150℃。
本发明中，金属卤化物优选SbCl5、SbF5或SbCl2F3，全氟磺酸优选FSO3H，金属卤化物与全氟磺酸的摩尔比优选1:1～5。
本发明中，反应在HF的氛围中进行。反应前，需用HF将催化剂中金属卤化物氟化为相应的氟化物或氟氯化物；也可直接加入相应的金属氟化物或氟氯化物。金属氟化物或氟氯化物和全氟磺酸组成催化剂，液相氟化HCFC-1233xf制备HCFC-244bb。
本发明中，全氟磺酸，可以直接采用商业品的全氟磺酸，也可由相应的含氯或溴磺酸经HF处理得到。
本发明的制备HCFC-244bb的方法可以间歇或连续进行。在间歇方法中，HF和HCFC-1233xf一次性加入至反应器，升至相应的反应温度，优选的反应条件为金属卤化物与全氟磺酸的摩尔比为1:0.1～10，HCFC-1233xf与HF的摩尔比为1:5～30，HCFC-1233xf与金属卤化物的摩尔比为0.5～5:1，反应温度为25℃～150℃，反应时间为0.5h～10h。在连续方法中，HF和HCFC-1233xf连续进入反应器，优选的反应条件为：金属卤化物与全氟磺酸的摩尔比为1:1～5，HCFC-1233xf与HF的摩尔比为1:1～5，HCFC-1233xf与金属卤化物的摩尔比为0.1～1:1，反应温度为35℃～100℃。
本发明中催化剂长时间运行后，金属卤化物中金属离子因发生价态的降 低导致催化剂活性下降，可向催化剂中通过氯气进行再生，使其恢复催化活性。再生过程中，先将反应体系中的有机物料排净，然后于50℃～150℃通入氯气和HF进行再生。
与现有技术相比，本发明的优点在于：
(1)反应选择性高，反应过程无需通入氯气，避免了氯气氯化HCFC-1233xf生成2,2,3-三氯-1,1,1-三氟丙烷、2,3-二氯-3,3,3-三氟丙烯等副产物，反应选择性为95.2％，最高可达到99.5％；
(2)液相氟化反应催化剂活性稳定，反应过程中无需通入氯气以维持催化剂活性，在连续运行900h期间，HCFC-1233xf转化率在90.0％以上，HCFC-244bb选择性为98.2％以上；
(3)催化剂活性降低后，经再生处理后，活性可恢复。
具体实施方式
下列结合实施例对本发明进一步详述说明，但并不限制本发明的范围。
实施例1
采用间歇液相氟化合成HCFC-244bb。向250mL的不锈钢高压釜中依次投入25g SbCl5，20.8g FSO3H，再加入35g HF进行氟化处理，处理过程及时排除生成的HCl，控制压力在0.25MPa以内。升温至60℃，恒温1h，处理过程结束。
向反应釜中加入18g HCFC-1233xf，在60℃下反应5h后降温。反应产物经水洗除酸后气相色谱分析，HCFC-1233xf的转化率为95.2％，HCFC-244bb的选择性为98.5％。
实施例2～9
实施例2～9制备HCFC-244bb的方法与实施例1相同，所不同的是改变 金属卤化物、全氟磺酸、反应温度和反应时间，反应结果如表1所示。
表1
Figure PCTCN2015072306-appb-000001
实施例16～21
实施例16～21制备HCFC-244bb的方法与实施例1相同，所不同的是改 变SbCl5与FSO3H的摩尔比、HCFC-1233xf与HF的摩尔比、HCFC-1233xf的投料量、反应温度和反应时间，反应结果如表2所示。
表2
Figure PCTCN2015072306-appb-000002
实施例22
采用连续液相氟化合成HCFC-244bb。向装有蒸馏塔和回流冷凝器的2L不锈钢高压釜中依次投入500g SbCl5，500g FSO3H，660g HF，及时排除生成的HCl，控制压力不超过0.25MPa，升温至60℃，恒温2h。再通过计量泵，将HCFC-1233xf与HF连续输送至反应器中，HCFC-1233xf的进料速率为43.5g/h，HF的进料速率为20g/h，HCFC-1233xf投料量与SbCl5的摩尔比为0.2:1，反应温度为58℃～63℃，反应结果见表3。由表3可知，连续运 行900h内，HCFC-1233xf转化率维持在90.0％-95.2％之间，HCFC-244bb选择性在98.2％以上，相比对比文献，反应过程中无需通入氯气催化剂仍保持很好的稳定性。
表3
Figure PCTCN2015072306-appb-000003
Figure PCTCN2015072306-appb-000004
Figure PCTCN2015072306-appb-000005
当试验连续运行900h时，催化剂活性缓慢下降，运行至1010h，HCFC-1233xf转化率降至80.1％。
实施例23
在实施例22运行1010h时，停止反应，排尽有机物料，在60℃通入氯气及HF，处理72h，降温，排尽反应釜内的氯气及氯化氢等物料，完成催化剂再生处理。
向反应釜中打入660g HF，随后利用计量泵，将HCFC-1233xf与HF连续输送至反应器中，HCFC-1233xf的进料速率为43.7g/h，HF的进料速率为20.2g/h，HCFC-1233xf与SbCl5的摩尔比为0.2:1，反应温度为58℃～63℃，反应结果见表4。由表4可知，试验连续运行520h，再生后催化剂的活性略有提高，反应期间HCFC-1233xf转化率维持在92.6％～95.9％之间，HCFC-244bb选择性在98.7％以上。实验结果表明，本实施例所使用的催化剂经再生后，活性可以恢复。
表4
Figure PCTCN2015072306-appb-000006
Figure PCTCN2015072306-appb-000007

Claims (3)

  1. 一种制备2-氯-1,1,1,2-四氟丙烷的方法，该方法以2-氯-3,3,3-三氟丙烯为原料，包括以下步骤：以金属卤化物和全氟磺酸为催化剂，2-氯-3,3,3-三氟丙烯与氟化氢液相氟化合成2-氯-1,1,1,2-四氟丙烷；其中金属卤化物为SbCl5、TiCl4、SnCl4、NbCl5、TaCl5、SbF5、SbCl2F3、TiF4、SnF4、NbF5或TaF5，全氟磺酸为FSO3H、CF3SO3H、C2F5SO3H或C4F9SO3H，金属卤化物与全氟磺酸的摩尔比为1:0.1～10，2-氯-3,3,3-三氟丙烯与HF的摩尔比为1:1～30，反应温度为25℃～150℃。
  2. 根据权利要求1所述的制备2-氯-1,1,1,2-四氟丙烷的方法，其特征在于所述的金属卤化物为SbCl5、SbF5或SbCl2F3；全氟磺酸为FSO3H。
  3. 根据权利要求1所述的制备2-氯-1,1,1,2-四氟丙烷的方法，其特征在于所述的金属卤化物与全氟磺酸的摩尔比为1:1～5。
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