CN102631947B - 一种用于乙炔氢氯化的金络合物催化剂 - Google Patents
一种用于乙炔氢氯化的金络合物催化剂 Download PDFInfo
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- CN102631947B CN102631947B CN201210100688.1A CN201210100688A CN102631947B CN 102631947 B CN102631947 B CN 102631947B CN 201210100688 A CN201210100688 A CN 201210100688A CN 102631947 B CN102631947 B CN 102631947B
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- 239000003054 catalyst Substances 0.000 title claims abstract description 60
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 title claims abstract description 50
- 239000010931 gold Substances 0.000 title claims abstract description 41
- 229910052737 gold Inorganic materials 0.000 title claims abstract description 34
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000007038 hydrochlorination reaction Methods 0.000 claims abstract description 34
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 33
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims abstract description 14
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 12
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000011591 potassium Substances 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 230000000694 effects Effects 0.000 claims abstract description 8
- 239000001103 potassium chloride Substances 0.000 claims abstract description 7
- 235000011164 potassium chloride Nutrition 0.000 claims abstract description 7
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 6
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 claims abstract description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims abstract description 3
- 235000005074 zinc chloride Nutrition 0.000 claims abstract description 3
- 239000011592 zinc chloride Substances 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical class SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 22
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 22
- 239000000956 alloy Substances 0.000 claims description 6
- 229910045601 alloy Inorganic materials 0.000 claims description 6
- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 claims description 4
- 238000005660 chlorination reaction Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract description 20
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 abstract description 19
- 229910052753 mercury Inorganic materials 0.000 abstract description 19
- 230000002194 synthesizing effect Effects 0.000 abstract description 17
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 229910000510 noble metal Inorganic materials 0.000 abstract description 8
- 238000005516 engineering process Methods 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 238000006424 Flood reaction Methods 0.000 description 19
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 13
- 230000004913 activation Effects 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000010953 base metal Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000003912 environmental pollution Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000002815 homogeneous catalyst Substances 0.000 description 3
- 230000002779 inactivation Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- -1 chlorauride Chemical compound 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910001510 metal chloride Inorganic materials 0.000 description 2
- 239000010970 precious metal Substances 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- SWGDHTSWHSSMLE-UHFFFAOYSA-N 3,3-dimethylpentane-2,4-dione Chemical compound CC(=O)C(C)(C)C(C)=O SWGDHTSWHSSMLE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005997 Calcium carbide Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229910015723 MoP Inorganic materials 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- SRNVHCKWYJALIZ-UHFFFAOYSA-N [Au].[N+](=O)(O)[O-].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [Au].[N+](=O)(O)[O-].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 SRNVHCKWYJALIZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JHXKRIRFYBPWGE-UHFFFAOYSA-K bismuth chloride Chemical compound Cl[Bi](Cl)Cl JHXKRIRFYBPWGE-UHFFFAOYSA-K 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- ICAKDTKJOYSXGC-UHFFFAOYSA-K lanthanum(iii) chloride Chemical compound Cl[La](Cl)Cl ICAKDTKJOYSXGC-UHFFFAOYSA-K 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910001463 metal phosphate Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- RWRDJVNMSZYMDV-UHFFFAOYSA-L radium chloride Chemical compound [Cl-].[Cl-].[Ra+2] RWRDJVNMSZYMDV-UHFFFAOYSA-L 0.000 description 1
- 229910001630 radium chloride Inorganic materials 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- CLZWAWBPWVRRGI-UHFFFAOYSA-N tert-butyl 2-[2-[2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-5-bromophenoxy]ethoxy]-4-methyl-n-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]anilino]acetate Chemical compound CC1=CC=C(N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)C(OCCOC=2C(=CC=C(Br)C=2)N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)=C1 CLZWAWBPWVRRGI-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
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Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102631942B (zh) * | 2012-04-17 | 2014-07-23 | 清华大学 | 一种用于乙炔氢氯化反应的复合金属盐催化剂 |
CN103623837B (zh) * | 2012-08-24 | 2016-01-06 | 天津市天地创智科技发展有限公司 | 乙炔氢氯化合成氯乙烯的Ru-Co-Cu催化剂 |
CN102976360B (zh) * | 2012-11-22 | 2014-12-10 | 长沙铂鲨环保设备有限公司 | 一种含硫氰酸根的金络合物及其制备方法和应用 |
CN104338560A (zh) * | 2013-07-31 | 2015-02-11 | 中昊(大连)化工研究设计院有限公司 | 一种合成氯乙烯用的复合金属络合物催化剂 |
CN104338561B (zh) * | 2013-07-31 | 2016-05-18 | 中昊(大连)化工研究设计院有限公司 | 一种合成氯乙烯用的复方低汞络合物催化剂及其制备方法 |
CN104289233A (zh) * | 2014-08-29 | 2015-01-21 | 冯良荣 | 乙炔氢氯化制氯乙烯的硫化物催化剂 |
CN104801345B (zh) * | 2015-03-31 | 2017-09-29 | 新疆兵团现代绿色氯碱化工工程研究中心(有限公司) | 一种用于乙炔氢氯化法生产氯乙烯的负载型无汞催化剂 |
CN105148989B (zh) * | 2015-07-28 | 2018-05-22 | 浙江工业大学 | 一种多孔固体材料负载型离子液体-金催化剂及其制备和应用 |
CN106732827A (zh) * | 2017-01-03 | 2017-05-31 | 新疆兵团现代绿色氯碱化工工程研究中心(有限公司) | 一种乙炔氢氯化贵金属无汞催化剂再生的方法 |
CN107803222B (zh) * | 2017-09-29 | 2020-06-09 | 浙江工业大学 | 一种用于乙炔氢氯化反应的钌配合物催化剂 |
CN108126716B (zh) * | 2017-12-26 | 2019-11-05 | 新疆兵团现代绿色氯碱化工工程研究中心(有限公司) | 一种乙炔氢氯化非汞催化剂 |
GB201908844D0 (en) * | 2019-06-20 | 2019-08-07 | Johnson Matthey Plc | Gold containing catalyst, method of preparation and use |
CN113145130B (zh) * | 2021-03-31 | 2023-05-23 | 浙江工业大学 | 一种用于乙炔氢氯化反应的负载含铜高熵合金活性炭催化剂及其制备方法和应用 |
CN113617393A (zh) * | 2021-07-28 | 2021-11-09 | 新疆至臻化工工程研究中心有限公司 | 一种乙炔氢氯化金属有机骨架材料催化剂 |
CN114146730A (zh) * | 2021-11-25 | 2022-03-08 | 内蒙古鄂尔多斯电力冶金集团股份有限公司 | 一种乙炔氢氯化金基催化剂及其制备方法 |
Citations (3)
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CN101670293A (zh) * | 2009-03-06 | 2010-03-17 | 清华大学 | 乙炔氢氯化反应用的无汞催化剂合成、再生方法及其应用 |
CN102029189A (zh) * | 2009-09-29 | 2011-04-27 | 华东理工大学 | 用于乙炔氢氯化反应的非汞催化剂以及用该催化剂制备氯乙烯的方法 |
CN102336631A (zh) * | 2011-07-15 | 2012-02-01 | 天津大学 | 延长含金催化剂使用寿命的乙炔法制备氯乙烯的方法 |
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CN101735005A (zh) * | 2008-11-14 | 2010-06-16 | 约翰逊马西有限公司 | 催化方法的改进 |
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101670293A (zh) * | 2009-03-06 | 2010-03-17 | 清华大学 | 乙炔氢氯化反应用的无汞催化剂合成、再生方法及其应用 |
CN102029189A (zh) * | 2009-09-29 | 2011-04-27 | 华东理工大学 | 用于乙炔氢氯化反应的非汞催化剂以及用该催化剂制备氯乙烯的方法 |
CN102336631A (zh) * | 2011-07-15 | 2012-02-01 | 天津大学 | 延长含金催化剂使用寿命的乙炔法制备氯乙烯的方法 |
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