CN103524371A - 一种2-氨基-4-乙酰氨基苯甲醚的制备工艺 - Google Patents
一种2-氨基-4-乙酰氨基苯甲醚的制备工艺 Download PDFInfo
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- CN103524371A CN103524371A CN201310308426.9A CN201310308426A CN103524371A CN 103524371 A CN103524371 A CN 103524371A CN 201310308426 A CN201310308426 A CN 201310308426A CN 103524371 A CN103524371 A CN 103524371A
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- acetyl
- amino
- anisidine
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- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- SJWQCBCAGCEWCV-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1N SJWQCBCAGCEWCV-UHFFFAOYSA-N 0.000 title abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 60
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 30
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 16
- 238000006722 reduction reaction Methods 0.000 claims abstract description 16
- 238000001816 cooling Methods 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 238000002425 crystallisation Methods 0.000 claims abstract description 8
- 238000004821 distillation Methods 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 230000008025 crystallization Effects 0.000 claims abstract description 5
- 238000000926 separation method Methods 0.000 claims abstract description 5
- 239000007788 liquid Substances 0.000 claims abstract description 3
- SWJZZIVUGZIVNC-UHFFFAOYSA-N NC1=C(OC)C=CC(C1)(N)C(C)=O Chemical compound NC1=C(OC)C=CC(C1)(N)C(C)=O SWJZZIVUGZIVNC-UHFFFAOYSA-N 0.000 claims description 29
- 238000005516 engineering process Methods 0.000 claims description 14
- CVYZVNVPQRKDLW-UHFFFAOYSA-N 2,4-dinitroanisole Chemical compound COC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O CVYZVNVPQRKDLW-UHFFFAOYSA-N 0.000 claims description 11
- 238000005917 acylation reaction Methods 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000011084 recovery Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- 238000006073 displacement reaction Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000007086 side reaction Methods 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-UHFFFAOYSA-N 0.000 description 2
- -1 500 kilograms Chemical compound 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000008676 import Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-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
- QRPFNVOUMDGOQA-ARJAWSKDSA-N COC/C=C\C(CC([N+]([O-])=O)=C)[N+]([O-])=O Chemical compound COC/C=C\C(CC([N+]([O-])=O)=C)[N+]([O-])=O QRPFNVOUMDGOQA-ARJAWSKDSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- UARLBWMPRYEBDQ-UHFFFAOYSA-N NC1=CC=C(C=C1)OC.C(C)(=O)NC1=C(C=CC=C1O)[As](O)(O)=O Chemical compound NC1=CC=C(C=C1)OC.C(C)(=O)NC1=C(C=CC=C1O)[As](O)(O)=O UARLBWMPRYEBDQ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical compound CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005267 amalgamation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical class CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
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CN201310308426.9A CN103524371B (zh) | 2013-07-22 | 2013-07-22 | 一种2-氨基-4-乙酰氨基苯甲醚的制备工艺 |
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CN201310308426.9A CN103524371B (zh) | 2013-07-22 | 2013-07-22 | 一种2-氨基-4-乙酰氨基苯甲醚的制备工艺 |
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CN103524371A true CN103524371A (zh) | 2014-01-22 |
CN103524371B CN103524371B (zh) | 2016-08-17 |
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Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104557598A (zh) * | 2015-01-21 | 2015-04-29 | 安徽生源化工有限公司 | 2-甲氧基-5-乙酰氨基苯胺的合成工艺 |
CN104926679A (zh) * | 2015-07-17 | 2015-09-23 | 郑州西格玛化工有限公司 | 一种2-氨基-4-乙酰氨基苯甲醚的制备方法 |
CN106608838A (zh) * | 2015-11-22 | 2017-05-03 | 宁夏际华环境安全科技有限公司 | 一种2-氨基-4乙酰氨基苯甲醚生产工艺 |
CN106866449A (zh) * | 2017-03-31 | 2017-06-20 | 九江善水科技股份有限公司 | 一种利用2,4‑二硝基苯酚加氢还原副产物回收制备2‑氨基‑4‑乙酰氨基苯甲醚的方法 |
CN107746380A (zh) * | 2017-11-06 | 2018-03-02 | 宁夏中盛新科技有限公司 | 一种2‑氨基‑4‑乙酰氨基苯甲醚的工业化生产方法 |
CN110437091A (zh) * | 2019-07-31 | 2019-11-12 | 中北大学 | 一种2,4-二氨基苯甲醚选择性酰化合成2-氨基-4-乙酰胺基苯甲醚的方法和装置 |
CN111269135A (zh) * | 2019-12-12 | 2020-06-12 | 中卫市鑫三元化工有限公司 | 一种2-氨基-4-乙酰氨基苯基醚的生产工艺 |
CN114181103A (zh) * | 2021-12-21 | 2022-03-15 | 浙江工业大学 | 一种以间苯二胺为原料合成间氨基乙酰苯胺的方法 |
CN114436876A (zh) * | 2020-10-30 | 2022-05-06 | 中国科学院大连化学物理研究所 | 一种2-氨基-4-乙酰氨基苯甲醚的连续合成方法 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4670589A (en) * | 1982-11-04 | 1987-06-02 | Monsanto Company | Preparation of N-acetyl-p-aminophenol |
JPH0859585A (ja) * | 1994-08-23 | 1996-03-05 | Mitsui Toatsu Chem Inc | α−アセトアミド桂皮酸の製造法 |
CN1861562A (zh) * | 2006-06-19 | 2006-11-15 | 常州市佳森化工有限公司 | 以氯苯生产硝基苯醚、氨基苯醚和酰氨基苯醚的工艺 |
CN1861577A (zh) * | 2006-06-19 | 2006-11-15 | 常州市佳森化工有限公司 | 制备2-氨基-4-乙酰氨基苯甲醚的工艺 |
CN102452953A (zh) * | 2010-10-19 | 2012-05-16 | 程大海 | 3-氨基-4-甲氧基乙酰胺的合成工艺 |
CN103030570A (zh) * | 2011-10-08 | 2013-04-10 | 殷越 | 3-氨基-4-甲氧基乙酰胺的合成工艺 |
-
2013
- 2013-07-22 CN CN201310308426.9A patent/CN103524371B/zh not_active Expired - Fee Related
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4670589A (en) * | 1982-11-04 | 1987-06-02 | Monsanto Company | Preparation of N-acetyl-p-aminophenol |
JPH0859585A (ja) * | 1994-08-23 | 1996-03-05 | Mitsui Toatsu Chem Inc | α−アセトアミド桂皮酸の製造法 |
CN1861562A (zh) * | 2006-06-19 | 2006-11-15 | 常州市佳森化工有限公司 | 以氯苯生产硝基苯醚、氨基苯醚和酰氨基苯醚的工艺 |
CN1861577A (zh) * | 2006-06-19 | 2006-11-15 | 常州市佳森化工有限公司 | 制备2-氨基-4-乙酰氨基苯甲醚的工艺 |
CN102452953A (zh) * | 2010-10-19 | 2012-05-16 | 程大海 | 3-氨基-4-甲氧基乙酰胺的合成工艺 |
CN103030570A (zh) * | 2011-10-08 | 2013-04-10 | 殷越 | 3-氨基-4-甲氧基乙酰胺的合成工艺 |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104557598A (zh) * | 2015-01-21 | 2015-04-29 | 安徽生源化工有限公司 | 2-甲氧基-5-乙酰氨基苯胺的合成工艺 |
CN104926679A (zh) * | 2015-07-17 | 2015-09-23 | 郑州西格玛化工有限公司 | 一种2-氨基-4-乙酰氨基苯甲醚的制备方法 |
CN104926679B (zh) * | 2015-07-17 | 2016-09-21 | 郑州西格玛化工有限公司 | 一种2-氨基-4-乙酰氨基苯甲醚的制备方法 |
CN106608838A (zh) * | 2015-11-22 | 2017-05-03 | 宁夏际华环境安全科技有限公司 | 一种2-氨基-4乙酰氨基苯甲醚生产工艺 |
CN106866449A (zh) * | 2017-03-31 | 2017-06-20 | 九江善水科技股份有限公司 | 一种利用2,4‑二硝基苯酚加氢还原副产物回收制备2‑氨基‑4‑乙酰氨基苯甲醚的方法 |
CN107746380A (zh) * | 2017-11-06 | 2018-03-02 | 宁夏中盛新科技有限公司 | 一种2‑氨基‑4‑乙酰氨基苯甲醚的工业化生产方法 |
CN107746380B (zh) * | 2017-11-06 | 2020-04-07 | 宁夏中盛新科技有限公司 | 一种2-氨基-4-乙酰氨基苯甲醚的工业化生产方法 |
CN110437091A (zh) * | 2019-07-31 | 2019-11-12 | 中北大学 | 一种2,4-二氨基苯甲醚选择性酰化合成2-氨基-4-乙酰胺基苯甲醚的方法和装置 |
CN111269135A (zh) * | 2019-12-12 | 2020-06-12 | 中卫市鑫三元化工有限公司 | 一种2-氨基-4-乙酰氨基苯基醚的生产工艺 |
CN114436876A (zh) * | 2020-10-30 | 2022-05-06 | 中国科学院大连化学物理研究所 | 一种2-氨基-4-乙酰氨基苯甲醚的连续合成方法 |
CN114436876B (zh) * | 2020-10-30 | 2023-03-14 | 中国科学院大连化学物理研究所 | 一种2-氨基-4-乙酰氨基苯甲醚的连续合成方法 |
CN114181103A (zh) * | 2021-12-21 | 2022-03-15 | 浙江工业大学 | 一种以间苯二胺为原料合成间氨基乙酰苯胺的方法 |
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