CN101381315B - 一种制备对氨基二苯胺的方法 - Google Patents
一种制备对氨基二苯胺的方法 Download PDFInfo
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- CN101381315B CN101381315B CN2008102243638A CN200810224363A CN101381315B CN 101381315 B CN101381315 B CN 101381315B CN 2008102243638 A CN2008102243638 A CN 2008102243638A CN 200810224363 A CN200810224363 A CN 200810224363A CN 101381315 B CN101381315 B CN 101381315B
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- liquid
- amido
- polyaniline
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- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 title abstract 8
- 238000002360 preparation method Methods 0.000 title description 8
- 239000007788 liquid Substances 0.000 claims abstract description 74
- 239000003054 catalyst Substances 0.000 claims abstract description 55
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 46
- 238000006722 reduction reaction Methods 0.000 claims abstract description 45
- 238000009833 condensation Methods 0.000 claims abstract description 39
- 230000005494 condensation Effects 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 38
- 238000000605 extraction Methods 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 239000012074 organic phase Substances 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 238000006482 condensation reaction Methods 0.000 claims abstract description 13
- 239000000047 product Substances 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- XXYMSQQCBUKFHE-UHFFFAOYSA-N 4-nitro-n-phenylaniline Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC1=CC=CC=C1 XXYMSQQCBUKFHE-UHFFFAOYSA-N 0.000 claims abstract description 7
- OIJHFHYPXWSVPF-UHFFFAOYSA-N para-Nitrosodiphenylamine Chemical compound C1=CC(N=O)=CC=C1NC1=CC=CC=C1 OIJHFHYPXWSVPF-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229920000767 polyaniline Polymers 0.000 claims description 44
- 239000008234 soft water Substances 0.000 claims description 37
- 239000000843 powder Substances 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 30
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 27
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 20
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 13
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 12
- 238000006297 dehydration reaction Methods 0.000 claims description 12
- 239000006200 vaporizer Substances 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 150000005621 tetraalkylammonium salts Chemical class 0.000 claims description 10
- CYGKLLHTPPFPHH-UHFFFAOYSA-N aniline;hydrate Chemical compound O.NC1=CC=CC=C1 CYGKLLHTPPFPHH-UHFFFAOYSA-N 0.000 claims description 8
- 239000012043 crude product Substances 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000002131 composite material Substances 0.000 claims description 5
- 229910052804 chromium Inorganic materials 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 229910052709 silver Inorganic materials 0.000 claims description 4
- 230000005587 bubbling Effects 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 2
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000000926 separation method Methods 0.000 abstract description 6
- 230000008901 benefit Effects 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 3
- 239000012071 phase Substances 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 238000005303 weighing Methods 0.000 description 19
- 238000003756 stirring Methods 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 7
- 239000002994 raw material Substances 0.000 description 6
- 239000000284 extract Substances 0.000 description 5
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical class [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 3
- 235000011130 ammonium sulphate Nutrition 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- GDDNTTHUKVNJRA-UHFFFAOYSA-N 3-bromo-3,3-difluoroprop-1-ene Chemical compound FC(F)(Br)C=C GDDNTTHUKVNJRA-UHFFFAOYSA-N 0.000 description 1
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- -1 after stirring Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229940107816 ammonium iodide Drugs 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000000998 batch distillation Methods 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000006324 decarbonylation Effects 0.000 description 1
- 238000006606 decarbonylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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CN2008102243638A CN101381315B (zh) | 2008-10-17 | 2008-10-17 | 一种制备对氨基二苯胺的方法 |
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CN101381315A CN101381315A (zh) | 2009-03-11 |
CN101381315B true CN101381315B (zh) | 2010-12-08 |
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Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102060714A (zh) * | 2010-06-25 | 2011-05-18 | 天津市有机化工一厂 | 一种制备4-氨基二苯胺的方法 |
CN102796011A (zh) * | 2012-08-25 | 2012-11-28 | 山西翔宇化工有限公司 | 一种对氨基二苯胺的制备方法 |
CN103864626B (zh) * | 2014-03-17 | 2016-04-06 | 山东尚舜化工有限公司 | 一种4-氨基二苯胺的催化加氢的生产设备及工艺 |
CN105585507B (zh) * | 2014-11-13 | 2019-04-30 | 江苏圣奥化学科技有限公司 | 4-氨基二苯胺的制备方法 |
CN104529916B (zh) * | 2014-12-25 | 2017-01-25 | 天津大学 | 从化工产品生产废料中分离高纯度吩嗪的方法 |
CN109665965A (zh) * | 2017-10-13 | 2019-04-23 | 中国石油化工股份有限公司 | 降低对氨基二苯胺生产中萃取软水用量的方法 |
CN108558675A (zh) * | 2018-04-25 | 2018-09-21 | 南通理工学院 | 一种4-氨基二苯胺的合成方法 |
CN113527111B (zh) * | 2020-04-10 | 2023-09-15 | 中国石油化工股份有限公司 | 一种常压缩合制备rt培司的方法 |
CN113402397A (zh) * | 2021-06-15 | 2021-09-17 | 中石化南京化工研究院有限公司 | 一种冷凝回流的rt培司制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1437573A (zh) * | 2000-06-21 | 2003-08-20 | 弗莱克塞斯美国公司 | 用于苯胺与硝基苯偶联的载有碱材料的沸石载体 |
CN1721390A (zh) * | 2004-07-15 | 2006-01-18 | 石光强 | 制备4-氨基二苯胺的方法 |
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Publication number | Priority date | Publication date | Assignee | Title |
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CN1437573A (zh) * | 2000-06-21 | 2003-08-20 | 弗莱克塞斯美国公司 | 用于苯胺与硝基苯偶联的载有碱材料的沸石载体 |
CN1721390A (zh) * | 2004-07-15 | 2006-01-18 | 石光强 | 制备4-氨基二苯胺的方法 |
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Free format text: FORMER OWNER: LI FENGNIAN Owner name: SHANXI XIANGYU CHEMICAL INDUSTRIAL CO., LTD. Free format text: FORMER OWNER: WANG QINGFENG Effective date: 20100511 |
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Free format text: CORRECT: ADDRESS; FROM: 044100 SHANXI XIANGYU CHEMICAL CO., LTD, XIFENG AVENUE, LINYI COUNTY, SHANXI PROVINCE TO: 044000 NO.1718, FENGXI STREET, LINYI COUNTY, SHANXI PROVINCE |
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Effective date of registration: 20100511 Address after: 044000 Shanxi Linyi wind Xi Road No. 1718 Applicant after: Shanxi Xiangyu Chemical Industries Co., Ltd. Address before: 044100 Shanxi Province Linyi County Toyoki Avenue Shanxi Xiangyu Chemical Co. Ltd. Applicant before: Wang Qingfeng Co-applicant before: Li Fengnian |
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Effective date of registration: 20180110 Address after: Bei Jing 044100 Shanxi Province Linyi County Shijiazhuang Township Village residents group ninth Patentee after: Zhang Guozhu Address before: 044000 Shanxi Province Linyi County Feng Xi Road No. 1718 Patentee before: Shanxi Xiangyu Chemical Industries Co., Ltd. |