CN1237575A - 由对硝基苯酚制备对氨基苯酚的液相加氢新工艺 - Google Patents
由对硝基苯酚制备对氨基苯酚的液相加氢新工艺 Download PDFInfo
- Publication number
- CN1237575A CN1237575A CN 99104692 CN99104692A CN1237575A CN 1237575 A CN1237575 A CN 1237575A CN 99104692 CN99104692 CN 99104692 CN 99104692 A CN99104692 A CN 99104692A CN 1237575 A CN1237575 A CN 1237575A
- Authority
- CN
- China
- Prior art keywords
- reduction
- novel process
- liquid
- kilograms
- aminophenol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 23
- 239000007791 liquid phase Substances 0.000 title claims abstract description 8
- 238000005984 hydrogenation reaction Methods 0.000 title abstract description 3
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title description 4
- 238000006722 reduction reaction Methods 0.000 claims abstract description 23
- 238000002425 crystallisation Methods 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 230000008025 crystallization Effects 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 239000002798 polar solvent Substances 0.000 claims abstract description 5
- 239000012452 mother liquor Substances 0.000 claims abstract description 4
- 238000000926 separation method Methods 0.000 claims abstract description 4
- 238000004148 unit process Methods 0.000 claims abstract description 3
- 238000000746 purification Methods 0.000 claims abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 8
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 15
- 238000001035 drying Methods 0.000 abstract description 6
- 238000011946 reduction process Methods 0.000 abstract description 3
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- 238000007086 side reaction Methods 0.000 abstract 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- 229910052742 iron Inorganic materials 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical class ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 99104692 CN1207267C (zh) | 1999-06-14 | 1999-06-14 | 由对硝基苯酚制备对氨基苯酚的液相加氢新工艺 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 99104692 CN1207267C (zh) | 1999-06-14 | 1999-06-14 | 由对硝基苯酚制备对氨基苯酚的液相加氢新工艺 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1237575A true CN1237575A (zh) | 1999-12-08 |
CN1207267C CN1207267C (zh) | 2005-06-22 |
Family
ID=5271798
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 99104692 Expired - Fee Related CN1207267C (zh) | 1999-06-14 | 1999-06-14 | 由对硝基苯酚制备对氨基苯酚的液相加氢新工艺 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1207267C (zh) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1328244C (zh) * | 2002-03-15 | 2007-07-25 | 南京工业大学 | 对氨基苯酚生产工艺 |
CN101696173B (zh) * | 2009-11-02 | 2012-11-07 | 浙江大学 | 邻氨基对叔丁基苯酚的合成方法 |
CN104447362A (zh) * | 2014-12-31 | 2015-03-25 | 河北冀衡(集团)药业有限公司 | 釜式连续加氢制备对氨基苯酚的反应系统及方法 |
CN107694563A (zh) * | 2017-09-12 | 2018-02-16 | 中国林业科学研究院林业新技术研究所 | 钯炭催化剂及其制备方法和应用 |
CN111302955A (zh) * | 2020-04-08 | 2020-06-19 | 江苏扬农化工集团有限公司 | 一种氨基苯酚的合成方法 |
CN115734961A (zh) * | 2020-04-27 | 2023-03-03 | 伊索美迪克公司 | 对乙酰氨基酚的连续合成方法 |
-
1999
- 1999-06-14 CN CN 99104692 patent/CN1207267C/zh not_active Expired - Fee Related
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1328244C (zh) * | 2002-03-15 | 2007-07-25 | 南京工业大学 | 对氨基苯酚生产工艺 |
CN101696173B (zh) * | 2009-11-02 | 2012-11-07 | 浙江大学 | 邻氨基对叔丁基苯酚的合成方法 |
CN104447362A (zh) * | 2014-12-31 | 2015-03-25 | 河北冀衡(集团)药业有限公司 | 釜式连续加氢制备对氨基苯酚的反应系统及方法 |
CN107694563A (zh) * | 2017-09-12 | 2018-02-16 | 中国林业科学研究院林业新技术研究所 | 钯炭催化剂及其制备方法和应用 |
CN111302955A (zh) * | 2020-04-08 | 2020-06-19 | 江苏扬农化工集团有限公司 | 一种氨基苯酚的合成方法 |
CN115734961A (zh) * | 2020-04-27 | 2023-03-03 | 伊索美迪克公司 | 对乙酰氨基酚的连续合成方法 |
Also Published As
Publication number | Publication date |
---|---|
CN1207267C (zh) | 2005-06-22 |
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TR01 | Transfer of patent right |
Effective date of registration: 20081226 Address after: No. 379, Huaibin Road, Bengbu, Anhui Patentee after: Anhui Bayi Chemical Industry Co., Ltd. Address before: No. 379, Huaibin Road, Bengbu, Anhui Patentee before: Anhui Bayi Chemical Group Co., Ltd. |
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ASS | Succession or assignment of patent right |
Owner name: ANHUI BAYI CHEMICAL ENGINEERING CO., LTD. Free format text: FORMER OWNER: ANHUI BAYI CHEMICAL ENGINEERING GROUP CO.,LTD. Effective date: 20081226 |
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CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20050622 Termination date: 20180614 |
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CF01 | Termination of patent right due to non-payment of annual fee |