CN100577613C - 臭氧-硝酸联用氧化含吸电子基苯环侧链的方法 - Google Patents
臭氧-硝酸联用氧化含吸电子基苯环侧链的方法 Download PDFInfo
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- CN100577613C CN100577613C CN200710161150A CN200710161150A CN100577613C CN 100577613 C CN100577613 C CN 100577613C CN 200710161150 A CN200710161150 A CN 200710161150A CN 200710161150 A CN200710161150 A CN 200710161150A CN 100577613 C CN100577613 C CN 100577613C
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- ozone
- nitric acid
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- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 229910017604 nitric acid Inorganic materials 0.000 title claims abstract description 39
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 25
- 230000003647 oxidation Effects 0.000 title claims abstract description 23
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 39
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 claims abstract description 22
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 31
- 239000005711 Benzoic acid Substances 0.000 claims description 15
- 235000010233 benzoic acid Nutrition 0.000 claims description 15
- 229960003053 thiamphenicol Drugs 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 230000008878 coupling Effects 0.000 claims description 12
- 238000010168 coupling process Methods 0.000 claims description 12
- 238000005859 coupling reaction Methods 0.000 claims description 12
- BEARMXYKACECDH-UHFFFAOYSA-N methylsulfonylmethylbenzene Chemical compound CS(=O)(=O)CC1=CC=CC=C1 BEARMXYKACECDH-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- TTWGDMXWCNPKGS-UHFFFAOYSA-N 2-nitro-4-sulfobenzoic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1[N+]([O-])=O TTWGDMXWCNPKGS-UHFFFAOYSA-N 0.000 claims description 5
- 235000011149 sulphuric acid Nutrition 0.000 claims description 4
- 239000001117 sulphuric acid Substances 0.000 claims description 4
- -1 nitro tosic acid Chemical group 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- OTVAEFIXJLOWRX-NXEZZACHSA-N thiamphenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl)C=C1 OTVAEFIXJLOWRX-NXEZZACHSA-N 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 10
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- 239000007791 liquid phase Substances 0.000 abstract description 2
- 239000007800 oxidant agent Substances 0.000 abstract description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 12
- 239000007789 gas Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 238000005868 electrolysis reaction Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000009413 insulation Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000007790 solid phase Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000007664 blowing Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Abstract
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CN200710161150A CN100577613C (zh) | 2007-12-14 | 2007-12-14 | 臭氧-硝酸联用氧化含吸电子基苯环侧链的方法 |
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CN200710161150A CN100577613C (zh) | 2007-12-14 | 2007-12-14 | 臭氧-硝酸联用氧化含吸电子基苯环侧链的方法 |
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CN101177369A CN101177369A (zh) | 2008-05-14 |
CN100577613C true CN100577613C (zh) | 2010-01-06 |
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Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103073461B (zh) * | 2013-01-11 | 2014-06-11 | 嘉兴学院 | 高价钒配合物催化体系制备2-硝基-4-甲砜基苯甲酸的方法 |
CN104262215A (zh) * | 2014-09-22 | 2015-01-07 | 锦州凯创化工科技有限公司 | 一种2-硝基-4-甲砜基苯甲酸的制备方法 |
CN105712912B (zh) * | 2014-12-02 | 2017-09-01 | 浙江省诸暨合力化学对外贸易有限公司 | 一种三酮类化合物及其中间体的制备方法 |
CN104557639B (zh) * | 2014-12-22 | 2017-05-10 | 沈阳化工研究院有限公司 | 一种制备2‑硝基‑4‑甲砜基苯甲酸的方法 |
CN104803815B (zh) * | 2015-03-25 | 2016-08-24 | 浙江嘉化能源化工股份有限公司 | 苯环上含吸电子基团的苯甲酸的工业化生产方法 |
CN105669504A (zh) * | 2016-03-07 | 2016-06-15 | 山东润博生物科技有限公司 | 一种2-硝基-4-甲砜基苯甲酸的制备方法 |
CN114213202B (zh) * | 2021-12-22 | 2024-07-05 | 石河子大学 | 一种2,4-取代苯甲酸的制备方法 |
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2007
- 2007-12-14 CN CN200710161150A patent/CN100577613C/zh active Active
Non-Patent Citations (4)
Title |
---|
2-硝基-4-甲砜基苯甲酸的合成方法. 李祥龙,庞怀林,杨剑波.精细化工中间体,第34卷第6期. 2004 |
2-硝基-4-甲砜基苯甲酸的合成方法. 李祥龙,庞怀林,杨剑波.精细化工中间体,第34卷第6期. 2004 * |
用臭氧氧化对硝基甲苯制备对硝基苯甲酸. 夏士朋.淮阴师范学院学报,第2卷第2期. 2003 |
用臭氧氧化对硝基甲苯制备对硝基苯甲酸. 夏士朋.淮阴师范学院学报,第2卷第2期. 2003 * |
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