CN101638406B - 邻-羟甲基苯甲酸内酯的制备方法 - Google Patents
邻-羟甲基苯甲酸内酯的制备方法 Download PDFInfo
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- CN101638406B CN101638406B CN2009100342652A CN200910034265A CN101638406B CN 101638406 B CN101638406 B CN 101638406B CN 2009100342652 A CN2009100342652 A CN 2009100342652A CN 200910034265 A CN200910034265 A CN 200910034265A CN 101638406 B CN101638406 B CN 101638406B
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- 238000000034 method Methods 0.000 title abstract description 30
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 title description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000000460 chlorine Substances 0.000 claims abstract description 24
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 24
- 239000003999 initiator Substances 0.000 claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 12
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 238000010606 normalization Methods 0.000 claims abstract description 5
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
- 238000001953 recrystallisation Methods 0.000 claims description 12
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 claims description 10
- 238000004817 gas chromatography Methods 0.000 claims description 9
- 238000004454 trace mineral analysis Methods 0.000 claims description 9
- 239000012043 crude product Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 3
- 229940050176 methyl chloride Drugs 0.000 claims description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 abstract description 96
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract description 6
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 abstract description 5
- 229940095102 methyl benzoate Drugs 0.000 abstract description 4
- 238000002474 experimental method Methods 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 17
- 239000000463 material Substances 0.000 description 16
- 238000001816 cooling Methods 0.000 description 15
- 238000002425 crystallisation Methods 0.000 description 11
- IUSPXLCLQIZFHL-UHFFFAOYSA-N 5-bromo-3h-2-benzofuran-1-one Chemical compound BrC1=CC=C2C(=O)OCC2=C1 IUSPXLCLQIZFHL-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000012452 mother liquor Substances 0.000 description 8
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 5
- 239000000919 ceramic Substances 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- IUBPHMYFMUGLCN-UHFFFAOYSA-N CC1C=CC(=CC1(C)C(=O)O)Br Chemical compound CC1C=CC(=CC1(C)C(=O)O)Br IUBPHMYFMUGLCN-UHFFFAOYSA-N 0.000 description 4
- 239000005800 Kresoxim-methyl Substances 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- ZOTBXTZVPHCKPN-HTXNQAPBSA-N kresoxim-methyl Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC=C1C ZOTBXTZVPHCKPN-HTXNQAPBSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000740 bleeding effect Effects 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 0 CC=C(C)C(C)=C(*)C1=C(C)COC1=O Chemical compound CC=C(C)C(C)=C(*)C1=C(C)COC1=O 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
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- 239000007791 liquid phase Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- CAHGWVAXFJXDNI-UHFFFAOYSA-N 1,4-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2Cl CAHGWVAXFJXDNI-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 208000035126 Facies Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 239000005857 Trifloxystrobin Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DBJUEJCZPKMDPA-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O DBJUEJCZPKMDPA-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
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- 239000000975 dye Substances 0.000 description 1
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- 150000002148 esters Chemical class 0.000 description 1
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- 239000012847 fine chemical Substances 0.000 description 1
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- 239000007789 gas Substances 0.000 description 1
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- 238000002386 leaching Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- WVWZECQNFWFVFW-UHFFFAOYSA-N methyl 2-methylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C WVWZECQNFWFVFW-UHFFFAOYSA-N 0.000 description 1
- LJGIJQVMUXOHBH-UHFFFAOYSA-N methyl 4-bromo-2-(chloromethyl)benzoate Chemical class COC(=O)C1=CC=C(Br)C=C1CCl LJGIJQVMUXOHBH-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
原料名称 | 数量(g) | 含量(%) | 分子量 | 摩尔数mol |
邻-甲基苯甲酸甲酯 | 1600 | 99 | 150.18 | 10.5 |
偶氮二异丁腈 | 0.5 | 99 | 164.21 | 0.003 |
氯气 | 约360 | 99.5 | 71 | 5.0 |
苯酞 | 10 | 99.5 | 134 |
原料名称 | 数量(g) | 含量(%) | 分子量 | 摩尔数mol |
4-溴-2-甲基苯甲酸甲酯 | 1620 | 99 | 229.07 | 7.0 |
偶氮二异丁腈 | 0.5 | 99 | 164.21 | 0.003 |
氯气 | 约215 | 99.5 | 71 | 3.0 |
5-溴苯酞 | 10 | 99.5 | 213 |
Claims (6)
Priority Applications (1)
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CN2009100342652A CN101638406B (zh) | 2009-09-03 | 2009-09-03 | 邻-羟甲基苯甲酸内酯的制备方法 |
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CN2009100342652A CN101638406B (zh) | 2009-09-03 | 2009-09-03 | 邻-羟甲基苯甲酸内酯的制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN101638406A CN101638406A (zh) | 2010-02-03 |
CN101638406B true CN101638406B (zh) | 2011-09-28 |
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CN2009100342652A Active CN101638406B (zh) | 2009-09-03 | 2009-09-03 | 邻-羟甲基苯甲酸内酯的制备方法 |
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Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102070583B (zh) * | 2010-11-15 | 2012-11-28 | 江苏耘农化工有限公司 | 2-苯并[c]呋喃酮的制备方法 |
CN105418577A (zh) * | 2015-11-26 | 2016-03-23 | 苏州黄河制药有限公司 | 一种以邻苯二甲醛为原料合成盐酸多塞平的方法 |
CN110498783A (zh) * | 2019-08-02 | 2019-11-26 | 成都蓝蜻蜓生物技术有限公司 | 一种合成罗沙司他中间体的方法 |
CN112079711A (zh) * | 2020-09-17 | 2020-12-15 | 白云山东泰商丘药业有限公司 | 一种对氯甲基苯甲酸的制备方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1634906A (zh) * | 2004-10-28 | 2005-07-06 | 临海市先锋化工有限公司 | 5-溴苯酞的合成 |
-
2009
- 2009-09-03 CN CN2009100342652A patent/CN101638406B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1634906A (zh) * | 2004-10-28 | 2005-07-06 | 临海市先锋化工有限公司 | 5-溴苯酞的合成 |
Non-Patent Citations (1)
Title |
---|
张春文等.5-溴苯酚合成工艺的研究进展.《精细化工中间体》.2008,第38卷(第6期),5-7. * |
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Address after: 222523 Jiangsu city of Lianyungang province guannaxian heap Chemical Industrial Park Gang Zhen gou Patentee after: Jiangsu Gengyun Chemical Co., Ltd. Address before: 212126 Zhenjiang City, Jiangsu province Dantu District Bingzhen Rong Patentee before: Jiangsu Gengyun Chemical Co., Ltd. |
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Address after: 222523 Jiangsu city of Lianyungang province guannaxian heap ditch town of Chemical Industrial Park Patentee after: Jiangsu Gengyun Chemical Co., Ltd. Address before: 222523 Jiangsu city of Lianyungang province guannaxian heap Chemical Industrial Park Gang Zhen gou Patentee before: Jiangsu Gengyun Chemical Co., Ltd. |