CN1207264C - 一种具有高苯胺收率的硝基苯加氢制苯胺方法 - Google Patents
一种具有高苯胺收率的硝基苯加氢制苯胺方法 Download PDFInfo
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- CN1207264C CN1207264C CN 02100610 CN02100610A CN1207264C CN 1207264 C CN1207264 C CN 1207264C CN 02100610 CN02100610 CN 02100610 CN 02100610 A CN02100610 A CN 02100610A CN 1207264 C CN1207264 C CN 1207264C
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- copper
- aniline
- manufacturing process
- nitrobenzene
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title claims abstract description 68
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 38
- 239000003054 catalyst Substances 0.000 title claims description 40
- 239000010949 copper Substances 0.000 claims abstract description 78
- 239000002131 composite material Substances 0.000 claims abstract description 39
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910052802 copper Inorganic materials 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims description 46
- RIOSMNKWWSAFGT-UHFFFAOYSA-N [O--].[Cu++].[Ce+3] Chemical compound [O--].[Cu++].[Ce+3] RIOSMNKWWSAFGT-UHFFFAOYSA-N 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 27
- 238000004519 manufacturing process Methods 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 21
- 238000009472 formulation Methods 0.000 claims description 16
- 229910052684 Cerium Inorganic materials 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 8
- 238000011068 loading method Methods 0.000 claims description 8
- 208000035126 Facies Diseases 0.000 claims description 7
- 239000011148 porous material Substances 0.000 claims description 6
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 claims description 5
- 239000010436 fluorite Substances 0.000 claims description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 150000000703 Cerium Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 abstract description 5
- 238000007086 side reaction Methods 0.000 abstract description 2
- 239000011949 solid catalyst Substances 0.000 abstract 4
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 abstract 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 abstract 1
- 230000027756 respiratory electron transport chain Effects 0.000 abstract 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 20
- 238000005303 weighing Methods 0.000 description 14
- 238000005516 engineering process Methods 0.000 description 13
- 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 description 11
- 238000000975 co-precipitation Methods 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000005554 pickling Methods 0.000 description 5
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000010970 precious metal Substances 0.000 description 2
- 230000001603 reducing effect Effects 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YVNRUPSDZZZUQJ-UHFFFAOYSA-N [O].NC1=CC=CC=C1 Chemical compound [O].NC1=CC=CC=C1 YVNRUPSDZZZUQJ-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- DRVWBEJJZZTIGJ-UHFFFAOYSA-N cerium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Ce+3].[Ce+3] DRVWBEJJZZTIGJ-UHFFFAOYSA-N 0.000 description 1
- OZECDDHOAMNMQI-UHFFFAOYSA-H cerium(3+);trisulfate Chemical compound [Ce+3].[Ce+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OZECDDHOAMNMQI-UHFFFAOYSA-H 0.000 description 1
- 229910000333 cerium(III) sulfate Inorganic materials 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- -1 copper cerium oxyhydroxide Chemical compound 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 238000000247 postprecipitation Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 229910001404 rare earth metal oxide Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
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- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
实施例号 | 催化剂样品号 | 催化剂构成 掺铜氧化铈复合氧 苯胺收化物中含Cu%(m) 率,% |
1718192021222324252627282930 | 1234567891011121314 | (Cu)CeO2(7.4)共沉淀法 7.4 100.0(Cu)CeO2(7.1)氨共沉淀法 7.1 99.97(Cu)CeO2(7.4)共沉淀法 7.4 100.0(Cu)CeO2(9.3)共沉淀法 9.3 99.99(Cu)CeO2(8.2)沉淀浸渍法 8.2 100.0(Cu)CeO2(8.2)焙烧浸渍法 8.2 99.99(Cu)CeO2(7.4)/γ-Al2O3共沉淀法 7.4 99.94(Cu)CeO2(7.4)/SiO2共沉淀法 7.4 99.95(Cu)CeO2(7.4)/γ-Al2O3浸渍法 7.4 99.96(Cu)CeO2(7.4)/SiO2浸渍法 7.4 99.96(Cu)CeO2(10.8)/γ-Al2O3浸渍法 10.8 99.95(Cu)CeO2(4.3)共沉淀法 4.3 85.23(Cu)CeO2(2.1)共沉淀法 2.1 72.51(Cu)CeO2(15.3)共沉淀法 15.3 99.65 |
Claims (9)
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CN 02100610 CN1207264C (zh) | 2002-01-25 | 2002-01-25 | 一种具有高苯胺收率的硝基苯加氢制苯胺方法 |
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CN 02100610 CN1207264C (zh) | 2002-01-25 | 2002-01-25 | 一种具有高苯胺收率的硝基苯加氢制苯胺方法 |
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CN1367040A CN1367040A (zh) | 2002-09-04 |
CN1207264C true CN1207264C (zh) | 2005-06-22 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US10322992B2 (en) | 2016-12-13 | 2019-06-18 | King Abdulaziz University | Methods of making cerium oxide polyaniline composite nanospheres and methods of use |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101045213B (zh) * | 2007-04-30 | 2010-05-19 | 陕西师范大学 | 固载离子液体-纳米金属粒子催化剂及其制备和在芳胺合成中的应用 |
CN103420849B (zh) * | 2012-05-16 | 2015-04-08 | 中国石油化工股份有限公司 | 用于连续化合成4-氨基二苯胺的方法 |
CN103341362B (zh) * | 2013-07-17 | 2015-07-15 | 临邑县鲁晶化工有限公司 | 用于邻硝基乙苯加氢制邻氨基乙苯的稀土-铜催化剂 |
CN103351303B (zh) * | 2013-07-17 | 2015-05-20 | 临邑县鲁晶化工有限公司 | 邻硝基乙苯加氢生产邻氨基乙苯的连续方法 |
CN106914255B (zh) * | 2017-03-29 | 2020-03-03 | 国家纳米科学中心 | 一种非合金金属复合物及其制备方法和应用 |
CN112958097A (zh) * | 2021-02-08 | 2021-06-15 | 清华大学 | 一种用于硝基苯加氢合成苯胺的铜基负载型催化剂及其制备方法 |
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US10322992B2 (en) | 2016-12-13 | 2019-06-18 | King Abdulaziz University | Methods of making cerium oxide polyaniline composite nanospheres and methods of use |
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