CN108530297A - 2-氯-3-甲基苯甲酸及其中间体的制备方法 - Google Patents
2-氯-3-甲基苯甲酸及其中间体的制备方法 Download PDFInfo
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- CN108530297A CN108530297A CN201710124561.6A CN201710124561A CN108530297A CN 108530297 A CN108530297 A CN 108530297A CN 201710124561 A CN201710124561 A CN 201710124561A CN 108530297 A CN108530297 A CN 108530297A
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- esterification
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Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- LWOKLXMNGXXORN-UHFFFAOYSA-N 2-chloro-3-methylbenzoic acid Chemical class CC1=CC=CC(C(O)=O)=C1Cl LWOKLXMNGXXORN-UHFFFAOYSA-N 0.000 title claims description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 35
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000001301 oxygen Substances 0.000 claims abstract description 33
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 33
- 150000008422 chlorobenzenes Chemical class 0.000 claims abstract description 29
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 15
- 239000003426 co-catalyst Substances 0.000 claims abstract description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000460 chlorine Substances 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 148
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 77
- 230000032050 esterification Effects 0.000 claims description 49
- 238000005886 esterification reaction Methods 0.000 claims description 49
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 22
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 19
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 17
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 16
- -1 chlorides phenyl formate Chemical class 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 238000004809 thin layer chromatography Methods 0.000 claims description 16
- 150000000345 2,6-xylenols Chemical class 0.000 claims description 15
- 238000004817 gas chromatography Methods 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 9
- 235000005074 zinc chloride Nutrition 0.000 claims description 9
- 239000011592 zinc chloride Substances 0.000 claims description 8
- 238000012544 monitoring process Methods 0.000 claims description 7
- JEFSTMHERNSDBC-UHFFFAOYSA-N 1,2-dimethylcyclohexa-2,4-dien-1-ol Chemical class CC1=CC=CCC1(C)O JEFSTMHERNSDBC-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 4
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical class CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229940011182 cobalt acetate Drugs 0.000 claims description 2
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 claims description 2
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 2
- SZKXDURZBIICCF-UHFFFAOYSA-N cobalt;pentane-2,4-dione Chemical compound [Co].CC(=O)CC(C)=O SZKXDURZBIICCF-UHFFFAOYSA-N 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 21
- 238000012805 post-processing Methods 0.000 abstract description 16
- 238000003912 environmental pollution Methods 0.000 abstract description 4
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 abstract 6
- 238000000034 method Methods 0.000 description 29
- 239000000047 product Substances 0.000 description 22
- 238000001514 detection method Methods 0.000 description 17
- 239000012141 concentrate Substances 0.000 description 14
- 238000011084 recovery Methods 0.000 description 14
- 239000006228 supernatant Substances 0.000 description 14
- 238000010792 warming Methods 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000012043 crude product Substances 0.000 description 11
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- JXFUQVJNPIAUTP-UHFFFAOYSA-N 2-chloro-3-formylbenzoic acid Chemical class OC(=O)C1=CC=CC(C=O)=C1Cl JXFUQVJNPIAUTP-UHFFFAOYSA-N 0.000 description 3
- NJKVZDOEWYNQIO-UHFFFAOYSA-N 2-chlorobenzene-1,3-dicarboxylic acid Chemical class OC(=O)C1=CC=CC(C(O)=O)=C1Cl NJKVZDOEWYNQIO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 239000013589 supplement Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- WNAJXPYVTFYEST-UHFFFAOYSA-N 2-Amino-3-methylbenzoate Chemical class CC1=CC=CC(C(O)=O)=C1N WNAJXPYVTFYEST-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- NZMAJUHVSZBJHL-UHFFFAOYSA-N n,n-dibutylformamide Chemical compound CCCCN(C=O)CCCC NZMAJUHVSZBJHL-UHFFFAOYSA-N 0.000 description 2
- 238000011017 operating method Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical class ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 1
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical class CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 1
- DGDAVTPQCQXLGU-UHFFFAOYSA-N 5437-38-7 Chemical class CC1=CC=CC(C(O)=O)=C1[N+]([O-])=O DGDAVTPQCQXLGU-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010054949 Metaplasia Diseases 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 239000003005 anticarcinogenic agent Substances 0.000 description 1
- IMXLQXHCHYKEEE-UHFFFAOYSA-N benzene;formic acid Chemical compound OC=O.C1=CC=CC=C1 IMXLQXHCHYKEEE-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000004320 controlled atmosphere Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 125000003929 folic acid group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 230000015689 metaplastic ossification Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
- C07C17/363—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms by elimination of carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
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CN201710124561.6A CN108530297B (zh) | 2017-03-03 | 2017-03-03 | 2-氯-3-甲基苯甲酸及其中间体的制备方法 |
Applications Claiming Priority (1)
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CN201710124561.6A CN108530297B (zh) | 2017-03-03 | 2017-03-03 | 2-氯-3-甲基苯甲酸及其中间体的制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN108530297A true CN108530297A (zh) | 2018-09-14 |
CN108530297B CN108530297B (zh) | 2021-09-24 |
Family
ID=63488557
Family Applications (1)
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CN201710124561.6A Active CN108530297B (zh) | 2017-03-03 | 2017-03-03 | 2-氯-3-甲基苯甲酸及其中间体的制备方法 |
Country Status (1)
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CN (1) | CN108530297B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111732520A (zh) * | 2019-07-30 | 2020-10-02 | 江苏超跃化学有限公司 | 一种3-甲基-2-氨基苯甲酸的制备方法 |
Citations (10)
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US5306849A (en) * | 1992-08-04 | 1994-04-26 | Bayer Aktiengesellschaft | Process for the preparation of halogenated aromatics |
CN1088572A (zh) * | 1992-11-23 | 1994-06-29 | 罗姆和哈斯公司 | 杀虫的n′-取代-n,n′-二酰肼 |
US5420364A (en) * | 1992-07-09 | 1995-05-30 | Bayer Aktiengesellschaft | Process for the preparation of halogenated aromatic compounds |
US5728773A (en) * | 1997-02-21 | 1998-03-17 | Minnesota Mining And Manufacturing Company | Fluoroelastomer composition with organo-onium and blocked-carbonate compounds |
US5874655A (en) * | 1994-05-05 | 1999-02-23 | Bayer Aktiengesellschaft | Process for the preparation of chlorinated aromatics |
CN1226895A (zh) * | 1996-06-07 | 1999-08-25 | 阿斯特拉公司 | 新的氨基酸衍生物及其作为凝血酶抑制剂的用途 |
CN101213166A (zh) * | 2005-06-28 | 2008-07-02 | 通用电气公司 | 芳族氯甲酸酯的制备方法 |
CN101648866A (zh) * | 2009-09-18 | 2010-02-17 | 刘忠春 | 一种对叔丁基苯甲酸的制备工艺 |
CN102336658A (zh) * | 2011-07-29 | 2012-02-01 | 安徽泰达新材料股份有限公司 | 一种3,5-二甲基苯甲酸的生产方法 |
CN105294419A (zh) * | 2015-11-18 | 2016-02-03 | 江苏联化科技有限公司 | 3,6-二氯-2-甲氧基苯甲酸及其中间体的合成方法 |
-
2017
- 2017-03-03 CN CN201710124561.6A patent/CN108530297B/zh active Active
Patent Citations (10)
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US5420364A (en) * | 1992-07-09 | 1995-05-30 | Bayer Aktiengesellschaft | Process for the preparation of halogenated aromatic compounds |
US5306849A (en) * | 1992-08-04 | 1994-04-26 | Bayer Aktiengesellschaft | Process for the preparation of halogenated aromatics |
CN1088572A (zh) * | 1992-11-23 | 1994-06-29 | 罗姆和哈斯公司 | 杀虫的n′-取代-n,n′-二酰肼 |
US5874655A (en) * | 1994-05-05 | 1999-02-23 | Bayer Aktiengesellschaft | Process for the preparation of chlorinated aromatics |
CN1226895A (zh) * | 1996-06-07 | 1999-08-25 | 阿斯特拉公司 | 新的氨基酸衍生物及其作为凝血酶抑制剂的用途 |
US5728773A (en) * | 1997-02-21 | 1998-03-17 | Minnesota Mining And Manufacturing Company | Fluoroelastomer composition with organo-onium and blocked-carbonate compounds |
CN101213166A (zh) * | 2005-06-28 | 2008-07-02 | 通用电气公司 | 芳族氯甲酸酯的制备方法 |
CN101648866A (zh) * | 2009-09-18 | 2010-02-17 | 刘忠春 | 一种对叔丁基苯甲酸的制备工艺 |
CN102336658A (zh) * | 2011-07-29 | 2012-02-01 | 安徽泰达新材料股份有限公司 | 一种3,5-二甲基苯甲酸的生产方法 |
CN105294419A (zh) * | 2015-11-18 | 2016-02-03 | 江苏联化科技有限公司 | 3,6-二氯-2-甲氧基苯甲酸及其中间体的合成方法 |
Non-Patent Citations (4)
Title |
---|
MATTHEW W. MARTIN等: "Novel 2-Aminopyrimidine Carbamates as Potent and Orally Active Inhibitors of Lck:Synthesis, SAR, and in Vivo Antiinflammatory Activity", 《JOURNAL OF MEDICINAL CHEMISTRY》 * |
NIMER TAHA等: "Co(II) Catalyzed Solvent Free Auto-Oxidation of Methylbenzenes to Substituted Benzoic Acids Under Phase Transfer Conditions", 《CATALYSIS LETTERS》 * |
NORBERT LUI等: "Liquid-Phase Decarboxylation of Aromatic Haloformates: A NewAccess to Chloro- and Fluoroaromati", 《JOURNAL OF ORGANIC CHEMISTRY》 * |
THOMAS B. SUNDBERG等: "Small-molecule screening identifies inhibition of salt-inducible kinases as a therapeutic strategy to enhance immunoregulatory functions of dendritic cells", 《PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA》 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111732520A (zh) * | 2019-07-30 | 2020-10-02 | 江苏超跃化学有限公司 | 一种3-甲基-2-氨基苯甲酸的制备方法 |
CN111732520B (zh) * | 2019-07-30 | 2022-08-26 | 江苏超跃化学有限公司 | 一种3-甲基-2-氨基苯甲酸的制备方法 |
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Publication number | Publication date |
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CN108530297B (zh) | 2021-09-24 |
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