CN110639497B - 一种2-氯-1,1,1,2-四氟丙烷制备2,3,3,3-四氟丙烯用的催化剂 - Google Patents
一种2-氯-1,1,1,2-四氟丙烷制备2,3,3,3-四氟丙烯用的催化剂 Download PDFInfo
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- 239000003054 catalyst Substances 0.000 title claims abstract description 46
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 title claims abstract description 30
- SMCNZLDHTZESTK-UHFFFAOYSA-N 2-chloro-1,1,1,2-tetrafluoropropane Chemical compound CC(F)(Cl)C(F)(F)F SMCNZLDHTZESTK-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 229910001635 magnesium fluoride Inorganic materials 0.000 claims abstract description 15
- HSJPMRKMPBAUAU-UHFFFAOYSA-N cerium(3+);trinitrate Chemical compound [Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O HSJPMRKMPBAUAU-UHFFFAOYSA-N 0.000 claims abstract description 10
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims abstract description 10
- 239000001095 magnesium carbonate Substances 0.000 claims abstract description 10
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims abstract description 10
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 claims abstract description 10
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims abstract description 10
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 claims abstract description 9
- 238000001035 drying Methods 0.000 claims abstract description 9
- 239000000395 magnesium oxide Substances 0.000 claims abstract description 9
- IWOUKMZUPDVPGQ-UHFFFAOYSA-N barium nitrate Chemical compound [Ba+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O IWOUKMZUPDVPGQ-UHFFFAOYSA-N 0.000 claims abstract description 8
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims abstract description 8
- NLSCHDZTHVNDCP-UHFFFAOYSA-N caesium nitrate Chemical compound [Cs+].[O-][N+]([O-])=O NLSCHDZTHVNDCP-UHFFFAOYSA-N 0.000 claims abstract description 8
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- DHEQXMRUPNDRPG-UHFFFAOYSA-N strontium nitrate Chemical compound [Sr+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O DHEQXMRUPNDRPG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000005470 impregnation Methods 0.000 claims abstract description 7
- NGDQQLAVJWUYSF-UHFFFAOYSA-N 4-methyl-2-phenyl-1,3-thiazole-5-sulfonyl chloride Chemical compound S1C(S(Cl)(=O)=O)=C(C)N=C1C1=CC=CC=C1 NGDQQLAVJWUYSF-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910001631 strontium chloride Inorganic materials 0.000 claims abstract description 5
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 claims abstract description 5
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 claims abstract description 4
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 claims abstract description 4
- 229910001626 barium chloride Inorganic materials 0.000 claims abstract description 4
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 claims abstract description 4
- FYDKNKUEBJQCCN-UHFFFAOYSA-N lanthanum(3+);trinitrate Chemical compound [La+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O FYDKNKUEBJQCCN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 description 30
- 238000002791 soaking Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 6
- 150000002736 metal compounds Chemical class 0.000 description 4
- 229910000510 noble metal Inorganic materials 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000007033 dehydrochlorination reaction Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
Classifications
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- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of rare earths
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/10—Magnesium; Oxides or hydroxides thereof
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- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
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- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/615—100-500 m2/g
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
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- Chemical Kinetics & Catalysis (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明公开了一种2‑氯‑1,1,1,2‑四氟丙烷制备2,3,3,3‑四氟丙烯用催化剂，表示为A‑B‑C/M，其中M为载体，A为活性组分，B和C为助催化剂；载体为氧化镁、氟化镁、碳酸镁、碱式碳酸镁中的一种或几种组成；活性组分为氟化铯、氯化铯、硝酸铯、氢氧化铯中的一种，以载体质量计，活性组分的含量为1％～15％；助催化剂B为氯化锶、硝酸锶、氯化钡、硝酸钡中的一种，以载体质量计，含量为0.5％～10％；助催化剂C为硝酸钇、硝酸镧、硝酸铈中的一种，以载体质量计，含量为0.1％～5％；采用共浸渍法或分步浸渍法将活性组分A、助催化剂B和C负载到载体M上，经干燥、焙烧，得到所需催化剂。本发明中的催化剂活性高，HFO‑1234yf选择性高，制备成本低，具有工业化应用价值。
Description
技术领域
本发明属于催化剂领域，具体涉及一种用于2-氯-1,1,1,2-四氟丙烷制备2,3,3,3-四氟丙烯的催化剂。
背景技术
含氟烯烃，特别是氢氟烯烃，如2,3,3,3-四氟丙烯(HFO-1234yf)是一零臭氧消耗潜值(ODP)、低GWP值的新型有机氟化物，被认为是目前广泛使用的HFCs的最佳替代品，可用作制冷剂、含氟聚合物单体等。
氯氟烷烃气相催化脱氯化氢是制备含氟烯烃的一种主要方法。如2-氯-1,1,1,2-四氟丙烷(HCFC-244bb)脱氯化氢生成HFO-1234yf。
专利US9180433B报道了Pd/MgO作为脱氯化氢催化剂，用于HCFC-244bb制备HFO-1234yf，反应温度450℃，反应初期HCFC-244bb的转化率为22.2％，HFO-1234yf的选择性仅为67.8％，反应13.5h后，HCFC-244bb的转化率即降为17.9％，HFO-1234yf的选择性则提高至97.1％，反应温度高，HCFC-244bb转化率低，反应初期HFO-1234yf选择性低，存在失活现象，并且催化剂制备过程中需使用昂贵的硝酸钯。
专利US9040759B报道了MgF2、LiCl/MgF2、K/MgF2和CsCl/MgF2作为脱氯化氢催化剂，用于HCFC-244bb制备HFO-1234yf，其中CsCl/MgF2综合性能最佳，反应温度475℃-510℃，HCFC-244bb转化率可达50％，HFO-1234yf选择性可达97％，反应温度高，HFO-1234yf的选择性尚有提升的空间。
目前HCFC-244bb制备HFO-1234yf的催化剂存在制备过程中需使用昂贵的贵金属化合物，成本高，反应温度高，HCFC-244bb转化率低和HFO-1234yf选择性尚需进一步提高的问题。
发明内容
针对现有技术存在的缺陷与不足，本发明的目的是提供一种制备过程中不需使用昂贵的贵金属化合物，成本低，反应温度低，HCFC-244bb转化率和HFO-1234yf选择性高的HCFC-244bb制备HFO-1234yf的催化剂。
为了实现本发明的目的，得到一种制备成本低、反应温度低、HCFC-244bb转化率和HFO-1234yf选择性高的催化剂，设想通过选用合适的载体、活性组分与助催化剂，通过三者的协同作用来降低反应温度、提高原料转化率和产物选择性；具体来说，载体通过选用高比表面积、具有介孔结构的氧化镁或高比表面积、具有中空介孔结构的氟化镁，可使活性组分和助催化剂在载体表面更好的分散，并使催化剂获得高的比表面积，载体选用碳酸镁或碱式碳酸镁，在后续焙烧过程中会分解释放出气体，可改善催化剂孔道结构和提高比表面积；活性组分和助催化剂B可共同调控催化剂表面酸碱性，使催化剂具有最适宜的酸碱性，既可提高原料转化率，又可改善产物选择性；催化剂C选自稀土元素化合物，可提高催化剂稳定性，延长催化剂寿命。
本发明所述的2-氯-1,1,1,2-四氟丙烷制备2,3,3,3-四氟丙烯的催化剂为负载型催化剂，催化剂可表示为A-B-C/M，其中M为载体，A为活性组分，B和C为助催化剂；载体为氧化镁、氟化镁、碳酸镁、碱式碳酸镁中的一种或几种组成，其中氧化镁具有介孔结构，比表面积大于200m2/g，氟化镁具有中空介孔结构，比表面积大于100m2/g；活性组分为氟化铯、氯化铯、硝酸铯、氢氧化铯中的一种，以载体质量计，活性组分的含量为1％～15％；助催化剂B为氯化锶、硝酸锶、氯化钡、硝酸钡中的一种，以载体质量计，含量为0.5％～10％；助催化剂C为硝酸钇、硝酸镧、硝酸铈中的一种，以载体质量计，含量为0.1％～5％；该催化剂制备步骤如下：采用共浸渍法或分步浸渍法将活性组分A、助催化剂B和C负载到载体M上，于80℃～140℃烘干，最后在380℃～450℃下焙烧，得到HCFC-244bb制备HFO-1234yf用催化剂。
与现有技术相比，本发明具有以下有益效果：
(1)现有催化剂制备过程中需使用昂贵的Pd的化合物，成本高，本发明中不需要使用昂贵的贵金属化合物，只需要使用廉价的非贵金属化合物，成本低。
(2)现有催化剂反应温度高，HCFC-244bb转化率低，HFO-1234yf选择性有待提高，本发明中催化剂反应温度低，HCFC-244bb转化率高，HFO-1234yf选择性高，可达98.5％以上。
具体实施方式
下面给出本发明的具体实施例，但并不限制本发明的范围。
催化剂性能的评价：剂量取5mL催化剂装入反应管中，待反应温度稳定在350℃后，通入HCFC-244bb，保持接触时间30s，运行100h，反应产物经水洗、碱洗吸收HCl和HF后，再经干燥，气相色谱进行分析，使用GC-2014C型气相色谱仪，色谱柱为GS-GasPro柱，氮气作载气，柱前压为80kPa，分流比为20:1，采用FID检测器，检测器温度为220℃，柱箱140℃恒温进样，采用峰面积归一化定量，得到原料转化率和HFO-1234yf的选择性数据。
实施例1
称取氟化铯0.50g、氯化锶0.20g和硝酸钇0.10g溶于适量水中配成浸渍液，然后浸渍10.00g氧化镁载体，其中氧化镁比表面积为230m2/g，具有介孔结构，于烘箱中80℃烘干，在马弗炉中380℃焙烧，制成催化剂。通过评价，HCFC-244bb转化率为52.1％，HFO-1234yf选择性为98.8％。
实施例2
称取氯化铯0.75g溶于适量水中配成浸渍液，然后浸渍10.00g氟化镁载体，其中氟化镁比表面积为108m2/g，具有中空介孔结构，于烘箱中100℃烘干，得到固体，将0.40g硝酸锶和0.25g硝酸镧溶于适量水中配成浸渍液，然后浸渍上述固体，于烘箱中100℃烘干，在马弗炉中400℃焙烧，制成催化剂。通过评价，HCFC-244bb转化率为55.3％，HFO-1234yf选择性为99.0％。
实施例3
称取硝酸铯2.50g、氯化钡1.70g和硝酸铈1.00g溶于适量水中配成浸渍液，然后浸渍20.00g碳酸镁载体，于烘箱中120℃烘干，在马弗炉中430℃焙烧，制成催化剂。通过评价，HCFC-244bb转化率为53.4％，HFO-1234yf选择性为98.6％。
实施例4
称取氢氧化铯0.20g，然后浸渍20.00g碱式碳酸镁载体，于烘箱中140℃烘干，得到固体，将0.10g硝酸钡和0.02g硝酸钇溶于适量水中配成浸渍液，然后浸渍上述固体，于烘箱中140℃烘干，在马弗炉中450℃焙烧，制成催化剂。通过评价，HCFC-244bb转化率为51.2％，HFO-1234yf选择性为98.7％。
实施例5
称取氯化铯1.50g、氯化锶1.00g和硝酸铈0.50g溶于适量水中配成浸渍液，然后浸渍10.00g氟化镁载体，其中氟化镁比表面积为108m2/g，具有中空介孔结构，于烘箱中110℃烘干，在马弗炉中420℃焙烧，制成催化剂。通过评价，HCFC-244bb转化率为57.9％，HFO-1234yf选择性为99.3％。
Claims (3)
1.一种2-氯-1,1,1,2-四氟丙烷制备2,3,3,3-四氟丙烯用的催化剂，其特征在于，所述催化剂为负载型催化剂，表示为A-B-C/M，其中M为载体，A为活性组分，B和C为助催化剂；
所述的载体M为氧化镁、氟化镁、碳酸镁、碱式碳酸镁中的一种或几种组成，其中氧化镁具有介孔结构，比表面积大于200m2/g；氟化镁具有中空介孔结构，比表面积大于100m2/g；
所述的活性组分A为氟化铯、氯化铯、硝酸铯、氢氧化铯中的一种；
所述的助催化剂B为氯化锶、硝酸锶、氯化钡、硝酸钡中的一种；
所述的助催化剂C为硝酸钇、硝酸镧、硝酸铈中的一种；
采用共浸渍法或分步浸渍法将活性组分A、助催化剂B和C负载到载体M上，于80℃～140℃烘干，最后在380℃～450℃下焙烧，得到2-氯-1,1,1,2-四氟丙烷制备2,3,3,3-四氟丙烯用催化剂。
2.根据权利要求1所述的2-氯-1,1,1,2-四氟丙烷制备2,3,3,3-四氟丙烯用的催化剂，其特征在于，以载体M质量计，活性组分A占载体M的质量比为1％～15％。
3.根据权利要求1所述的2-氯-1,1,1,2-四氟丙烷制备2,3,3,3-四氟丙烯用的催化剂，其特征在于，以载体M质量计，助催化剂B占载体M的质量比为0.5％～10％，助催化剂C占载体M的质量比为0.1％～5％。
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