DD151744A5 - Verfahren zur herstellung von 2-nitro-5(substituierter-phenoxy)-benzoesaeuren und deren salzen - Google Patents

Verfahren zur herstellung von 2-nitro-5(substituierter-phenoxy)-benzoesaeuren und deren salzen Download PDF

Info

Publication number: DD151744A5
Authority: DD; German Democratic Republic
Prior art keywords: substituted phenoxy; acid; nitro; substituted; benzoic acid
Prior art date: 1979-06-22

Application number

DD80222087A

Other languages

German (de)

English (en)

Inventor

Robert W Etherington

Robert Theissen

Original Assignee

Mobil Oil Corp

Priority date (The priority date 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 date listed.)

1979-06-22

Filing date

1980-06-23

Publication date

1981-11-04

1980-06-23 Application filed by Mobil Oil Corp filed Critical Mobil Oil Corp

1981-11-04 Publication of DD151744A5 publication Critical patent/DD151744A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 31
150000003839 salts Chemical class 0.000 title claims abstract description 16
238000002360 preparation method Methods 0.000 title claims abstract description 9
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical class O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 title 1
-1 2-nitro-5- (substituted phenoxy) benzoic acids Chemical class 0.000 claims abstract description 37
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 12
150000001875 compounds Chemical class 0.000 claims abstract description 10
229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
229910052794 bromium Inorganic materials 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 16
239000012141 concentrate Substances 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
239000013256 coordination polymer Substances 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 37
239000004480 active ingredient Substances 0.000 abstract description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 9
230000002363 herbicidal effect Effects 0.000 abstract description 7
239000007858 starting material Substances 0.000 abstract description 4
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 abstract 1
229930003836 cresol Natural products 0.000 abstract 1
239000007787 solid Substances 0.000 description 21
239000000047 product Substances 0.000 description 17
235000008504 concentrate Nutrition 0.000 description 14
239000007788 liquid Substances 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
238000005859 coupling reaction Methods 0.000 description 10
239000002904 solvent Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000013543 active substance Substances 0.000 description 9
239000000126 substance Substances 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
238000009472 formulation Methods 0.000 description 8
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
230000003647 oxidation Effects 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 5
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 5
IJFXRHURBJZNAO-UHFFFAOYSA-N meta--hydroxybenzoic acid Natural products OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
235000010233 benzoic acid Nutrition 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
230000008878 coupling Effects 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000000428 dust Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
235000014666 liquid concentrate Nutrition 0.000 description 3
229910017604 nitric acid Inorganic materials 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000002002 slurry Substances 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000007921 spray Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
ONKRUAQFUNKYAX-UHFFFAOYSA-N 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 ONKRUAQFUNKYAX-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
240000007049 Juglans regia Species 0.000 description 2
235000009496 Juglans regia Nutrition 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
241000208125 Nicotiana Species 0.000 description 2
235000002637 Nicotiana tabacum Nutrition 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
239000000440 bentonite Substances 0.000 description 2
229910000278 bentonite Inorganic materials 0.000 description 2
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
235000012343 cottonseed oil Nutrition 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
229910001882 dioxygen Inorganic materials 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
235000013312 flour Nutrition 0.000 description 2
239000007789 gas Substances 0.000 description 2
150000005171 halobenzenes Chemical class 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000000802 nitrating effect Effects 0.000 description 2
238000006396 nitration reaction Methods 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000002245 particle Substances 0.000 description 2
230000000361 pesticidal effect Effects 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000001103 potassium chloride Substances 0.000 description 2
235000011164 potassium chloride Nutrition 0.000 description 2
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
229910052903 pyrophyllite Inorganic materials 0.000 description 2
238000010992 reflux Methods 0.000 description 2
150000004760 silicates Chemical class 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
238000005507 spraying Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
235000020234 walnut Nutrition 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
FBKFIAIRSQOXJR-UHFFFAOYSA-N 1,2,3-trichloro-5-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Cl)=C(Cl)C(Cl)=C1 FBKFIAIRSQOXJR-UHFFFAOYSA-N 0.000 description 1
XILPLWOGHPSJBK-UHFFFAOYSA-N 1,2-dichloro-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Cl)C(Cl)=C1 XILPLWOGHPSJBK-UHFFFAOYSA-N 0.000 description 1
FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 1
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
TYCQLNBCQSJWGJ-UHFFFAOYSA-N 2,6,6-trichlorocyclohexa-1,3-diene Chemical compound ClC1=CC(Cl)(Cl)CC=C1 TYCQLNBCQSJWGJ-UHFFFAOYSA-N 0.000 description 1
DNUYOWCKBJFOGS-UHFFFAOYSA-N 2-[[10-(2,2-dicarboxyethyl)anthracen-9-yl]methyl]propanedioic acid Chemical compound C1=CC=C2C(CC(C(=O)O)C(O)=O)=C(C=CC=C3)C3=C(CC(C(O)=O)C(O)=O)C2=C1 DNUYOWCKBJFOGS-UHFFFAOYSA-N 0.000 description 1
CSXRLIIXUVVUTK-UHFFFAOYSA-N 2-chloro-1-(3-methylphenoxy)-4-(trifluoromethyl)benzene Chemical compound CC1=CC=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CSXRLIIXUVVUTK-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
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101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 1
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101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
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229930195725 Mannitol Natural products 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
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ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
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150000001263 acyl chlorides Chemical class 0.000 description 1
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125000001931 aliphatic group Chemical group 0.000 description 1
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150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
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238000009835 boiling Methods 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical group CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
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239000012467 final product Substances 0.000 description 1
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239000003205 fragrance Substances 0.000 description 1
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239000010440 gypsum Substances 0.000 description 1
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238000010438 heat treatment Methods 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
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238000002329 infrared spectrum Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003999 initiator Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
229910052622 kaolinite Inorganic materials 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229940070765 laurate Drugs 0.000 description 1
239000010410 layer Substances 0.000 description 1
150000002672 m-cresols Chemical class 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
235000011160 magnesium carbonates Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
150000007522 mineralic acids Chemical group 0.000 description 1
150000005338 nitrobenzoic acids Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229920000223 polyglycerol Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000004323 potassium nitrate Substances 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
239000010802 sludge Substances 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/33—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups or etherified hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/16—Separation; Purification; Stabilisation; Use of additives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C203/00—Esters of nitric or nitrous acid
- C07C203/02—Esters of nitric acid
- C07C203/10—Esters of nitric acid having nitrate groups bound to carbon atoms of six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/34—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms of the carbon skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

DD80222087A 1979-06-22 1980-06-23 Verfahren zur herstellung von 2-nitro-5(substituierter-phenoxy)-benzoesaeuren und deren salzen DD151744A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US5125479A	1979-06-22	1979-06-22
US6750879A	1979-08-17	1979-08-17

Publications (1)

Publication Number	Publication Date
DD151744A5 true DD151744A5 (de)	1981-11-04

Family

ID=26729219

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80222087A DD151744A5 (de)	1979-06-22	1980-06-23	Verfahren zur herstellung von 2-nitro-5(substituierter-phenoxy)-benzoesaeuren und deren salzen

Country Status (10)

Country	Link
EP (1)	EP0022610B1 (da)
KR (1)	KR860000581B1 (da)
AU (1)	AU544426B2 (da)
BR (1)	BR8003563A (da)
CA (1)	CA1176649A (da)
DD (1)	DD151744A5 (da)
DE (1)	DE3071736D1 (da)
DK (1)	DK157006C (da)
ES (1)	ES492627A0 (da)
IL (1)	IL60271A (da)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0063873A1 (en) *	1981-04-28	1982-11-03	Imperial Chemical Industries Plc	Haloalkoxy-substituted diphenyl ethers; their use as herbicides and in herbicidal compositions and processes of making them
US4405805A (en) *	1981-07-27	1983-09-20	Rhone-Poulenc, Inc.	Process for recovering and purifying herbicidal phenoxybenzoic acid derivatives
US4594440A (en) *	1981-07-27	1986-06-10	Rhone:Pulenc, Inc.	Process for recovering and purifying herbicidal phenoxybenzoic acid derivatives
US4484008A (en) *	1982-09-30	1984-11-20	Ppg Industries, Inc.	Process improvement for diphenyl ether production
DE3624913A1 (de) *	1986-07-23	1988-01-28	Hoechst Ag	Verfahren zur herstellung von 2.2-bis(3-nitrophenyl)-hexafluorpropan sowie das dabei als zwischenprodukt auftretende 2.2-bis(4-carboxy-3-nitrophenyl)hexafluorpropan
GB8628109D0 (en) *	1986-11-25	1986-12-31	Ici Plc	Chemical process
US5446197A (en) *	1994-10-04	1995-08-29	Basf Corporation	Method of purifying acifluorfen
US5910604A (en) *	1995-09-13	1999-06-08	Zeneca Limited	Purification process
GB9518704D0 (en) *	1995-09-13	1995-11-15	Zeneca Ltd	Chemical process
US6028219A (en) *	1995-09-13	2000-02-22	Zeneca Limited	Process for the nitration of diphenylethers
CN103787890A (zh) *	2014-02-28	2014-05-14	江苏省激素研究所股份有限公司	一种三氟羧草醚的合成方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1293540A (en) *	1968-12-31	1972-10-18	Coalite Chem Prod Ltd	Preparation of diaryl ethers and thioethers
US3941830A (en) *	1971-02-11	1976-03-02	Mobil Oil Corporation	Substituted phenoxybenzoic acids and esters thereof
JPS5610883B2 (da) *	1973-12-27	1981-03-11
US4031131A (en) *	1975-09-29	1977-06-21	Rohm And Haas Company	Process for preparing phenoxybenzoic acids

1980
- 1980-05-20 DE DE8080301648T patent/DE3071736D1/de not_active Expired
- 1980-05-20 EP EP80301648A patent/EP0022610B1/en not_active Expired
- 1980-05-30 CA CA000353102A patent/CA1176649A/en not_active Expired
- 1980-06-06 AU AU59117/80A patent/AU544426B2/en not_active Ceased
- 1980-06-09 IL IL60271A patent/IL60271A/xx unknown
- 1980-06-09 BR BR8003563A patent/BR8003563A/pt unknown
- 1980-06-20 ES ES492627A patent/ES492627A0/es active Granted
- 1980-06-20 DK DK263180A patent/DK157006C/da not_active IP Right Cessation
- 1980-06-20 KR KR1019800002436A patent/KR860000581B1/ko not_active Expired
- 1980-06-23 DD DD80222087A patent/DD151744A5/de unknown

Also Published As

Publication number	Publication date
ES8105692A1 (es)	1981-06-01
KR860000581B1 (ko)	1986-05-17
CA1176649A (en)	1984-10-23
DK263180A (da)	1980-12-23
IL60271A0 (en)	1980-09-16
ES492627A0 (es)	1981-06-01
EP0022610B1 (en)	1986-09-03
KR830002701A (ko)	1983-05-30
AU544426B2 (en)	1985-05-30
EP0022610A1 (en)	1981-01-21
IL60271A (en)	1984-08-31
DK157006B (da)	1989-10-30
DK157006C (da)	1990-04-02
AU5911780A (en)	1981-01-08
DE3071736D1 (en)	1986-10-09
BR8003563A (pt)	1981-01-05

Publication	Publication Date	Title
DE2406475C2 (de)	1983-04-28	5-Acetamido-2,4-dimethyltrifluormethansulfonanilid und dessen landwirtschaftlich geeignete Salze, Verfahren zur Herstellung dieser Verbindungen und diese Verbindungen enthaltende Mittel
DE2632581C2 (de)	1982-07-15	Substituierte Nitrodiphenylether, Verfahren zu ihrer Herstellung und diese enthaltende herbizide Mittel
DE60203595T2 (de)	2005-11-03	Stabilisierte o-iodoxybenzoesäurezusammensetzungen und verfahren zu ihrer herstellung
DD151744A5 (de)	1981-11-04	Verfahren zur herstellung von 2-nitro-5(substituierter-phenoxy)-benzoesaeuren und deren salzen
DD232184A5 (de)	1986-01-22	Pestizide zusammensetzung
DE1542943B2 (de)	1975-04-30	Benzonitrilderivate und diese enthaltende herbizide Zusammensetzungen
EP0132733A2 (de)	1985-02-13	Neue Fluorpivalsäurefluoride und Verfahren zu ihrer Herstellung
DE1047776B (de)	1958-12-31	Verfahren zur Herstellung von Thionophosphorsaeureestern
DE2918541C3 (de)	1981-12-24	Diphenylaminderivate, Verfahren zu deren Herstellung und herbicide Mittel auf deren Basis
DD202423A5 (de)	1983-09-14	Verfahren zur gewinnung und reinigung von phenoxybenzoesaeurederivaten
EP0551632A2 (de)	1993-07-21	Verfahren zur Herstellung von Halogenanthranilsäuren
DE2519315C2 (de)	1986-10-30	Verfahren zur Herstellung von 3-Trichlormethyl-5-chlor-1,2,4-thiadiazol
DE2152722A1 (de)	1973-05-03	Verfahren zur herstellung von isatosaeureanhydrid und 3-azaisatosaeureanhydrid
EP0123087B1 (de)	1987-07-01	Verfahren zur Herstellung heterocyclischer Phenylether
DE1542872A1 (de)	1970-07-02	Selektives herbizides Mittel
DD156662A5 (de)	1982-09-15	Unkrautbekaempfungsmittel
DE2527575C3 (de)	1978-08-10	Verfahren zur Herstellung von 5-Methyl-2-nitrophenol
DE2215863C3 (de)	1982-01-07	Jodäthylester aromatischer Carbonsäuren, Verfahren zu deren Herstellung sowie Mittel zur Beeinflussung des Pflanzenstoffwechsels enthaltend die genannten Ester
CH640214A5 (de)	1983-12-30	Chloracetanilide, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel.
EP0150411A1 (de)	1985-08-07	Verfahren zur Herstellung substituierter Chinazolin-2.4(1H.3H)-dione
DE3038083A1 (de)	1981-09-10	5-(2'-chlor-4'-trifluormethylphenoxy)-2-nitrostyrolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende herbizide mittel
AT239243B (de)	1965-03-25	Verfahren zur Herstellung von 2, 3-Dicyan-1, 4-dithia-anthrahydrochinon und -anthrachinon
AT344443B (de)	1978-07-25	Herbizides mittel
DE3025221A1 (de)	1982-02-04	Halogenmethylsulfonylphenyl-phthalamidsaeuren, verfahren zu ihrer herstellung und ihre bakterizide verwendung
AT375360B (de)	1984-07-25	Verfahren zur herstellung von neuen 1,3-benzodioxol-derivaten und deren salzen