LU84297A1 - Procede de purification de derives d'acides phenoxybenzoiques - Google Patents

Procede de purification de derives d'acides phenoxybenzoiques Download PDF

Info

Publication number: LU84297A1
Authority: LU; Luxembourg
Prior art keywords: derivative; chloro; crude; phenoxybenzoic acid; acifluorfen
Prior art date: 1981-07-27

Application number

LU84297A

Other languages

English (en)

French (fr)

Inventor

Thomas J Giacobbe

Grace Tsien

Original Assignee

Rhone Poulenc Agrochimie

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.)

1981-07-27

Filing date

1982-07-26

Publication date

1984-03-22

1982-07-26 Application filed by Rhone Poulenc Agrochimie filed Critical Rhone Poulenc Agrochimie

1984-03-22 Publication of LU84297A1 publication Critical patent/LU84297A1/fr

Links

238000000034 method Methods 0.000 title claims description 23
PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical class OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 title claims description 21
238000000746 purification Methods 0.000 title description 5
NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 19
239000008096 xylene Substances 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 10
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 8
230000003647 oxidation Effects 0.000 claims description 8
238000007254 oxidation reaction Methods 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
WCOYPFBMFKXWBM-UHFFFAOYSA-N 1-methyl-2-phenoxybenzene Chemical compound CC1=CC=CC=C1OC1=CC=CC=C1 WCOYPFBMFKXWBM-UHFFFAOYSA-N 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 5
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 5
229940100630 metacresol Drugs 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
150000003738 xylenes Chemical class 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
239000006227 byproduct Substances 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
150000002430 hydrocarbons Chemical group 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
150000002926 oxygen Chemical class 0.000 claims 1
BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical class C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
229910001868 water Inorganic materials 0.000 description 15
239000000243 solution Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 13
239000000047 product Substances 0.000 description 13
238000006396 nitration reaction Methods 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
238000004821 distillation Methods 0.000 description 6
238000011084 recovery Methods 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
238000005859 coupling reaction Methods 0.000 description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
230000008878 coupling Effects 0.000 description 4
238000010168 coupling process Methods 0.000 description 4
239000013067 intermediate product Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
239000012535 impurity Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
229940011182 cobalt acetate Drugs 0.000 description 2
QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
230000007423 decrease Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
230000002363 herbicidal effect Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000012466 permeate Substances 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
239000001103 potassium chloride Substances 0.000 description 2
235000011164 potassium chloride Nutrition 0.000 description 2
238000004064 recycling Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
ZGGSVBWJVIXBHV-UHFFFAOYSA-N 2-chloro-1-(4-nitrophenoxy)-4-(trifluoromethyl)benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(C(F)(F)F)C=C1Cl ZGGSVBWJVIXBHV-UHFFFAOYSA-N 0.000 description 1
ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 description 1
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 1
NDALMJAMEGJJEX-UHFFFAOYSA-N 3-[2-chloro-5-(trifluoromethyl)phenoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C(=CC=C(C=2)C(F)(F)F)Cl)=C1 NDALMJAMEGJJEX-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
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 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
241000278713 Theora Species 0.000 description 1
238000013019 agitation Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
XOVJAYNMQDTIJD-UHFFFAOYSA-N cyclopentobarbital Chemical compound C1CC=CC1C1(CC=C)C(=O)NC(=O)NC1=O XOVJAYNMQDTIJD-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
SLHSZNQIHNFAGY-UHFFFAOYSA-M potassium;2-hydroxy-6-methylbenzoate Chemical compound [K+].CC1=CC=CC(O)=C1C([O-])=O SLHSZNQIHNFAGY-UHFFFAOYSA-M 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
239000004071 soot Substances 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
229910052727 yttrium Inorganic materials 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
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

LU84297A 1981-07-27 1982-07-26 Procede de purification de derives d'acides phenoxybenzoiques LU84297A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/286,996 US4405805A (en)	1981-07-27	1981-07-27	Process for recovering and purifying herbicidal phenoxybenzoic acid derivatives
US28699681		1981-07-27

Publications (1)

Publication Number	Publication Date
LU84297A1 true LU84297A1 (fr)	1984-03-22

Family

ID=23101031

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU84297A LU84297A1 (fr)	1981-07-27	1982-07-26	Procede de purification de derives d'acides phenoxybenzoiques

Country Status (22)

Country	Link
US (1)	US4405805A (pl)
JP (1)	JPS5838235A (pl)
KR (1)	KR890001806B1 (pl)
BE (1)	BE893942A (pl)
BR (1)	BR8204352A (pl)
CA (1)	CA1203811A (pl)
CH (1)	CH652710A5 (pl)
DD (1)	DD202423A5 (pl)
DE (1)	DE3227846A1 (pl)
DK (1)	DK333582A (pl)
ES (2)	ES514354A0 (pl)
FR (1)	FR2510102B1 (pl)
GB (1)	GB2103214B (pl)
HU (1)	HU190694B (pl)
IE (1)	IE54596B1 (pl)
IL (1)	IL66357A (pl)
IT (1)	IT1156314B (pl)
LU (1)	LU84297A1 (pl)
NL (1)	NL8202995A (pl)
PL (1)	PL144334B1 (pl)
PT (1)	PT75324B (pl)
RO (1)	RO85386B (pl)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3129826A1 (de) *	1981-07-29	1983-04-28	Grillo-Werke Ag, 4100 Duisburg	Zinksalz der hydrolisierten tricarbonsaeure aus diels-alder-addukten von maleinsaeureanhydrid an undecylensaeure, verfahren zur herstellung derselben und ihre verwendung
US5446197A (en) *	1994-10-04	1995-08-29	Basf Corporation	Method of purifying acifluorfen
GB9518704D0 (en) *	1995-09-13	1995-11-15	Zeneca Ltd	Chemical process
GB9518705D0 (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
US5910604A (en) *	1995-09-13	1999-06-08	Zeneca Limited	Purification process
GB9930369D0 (en) *	1999-12-22	2000-02-09	Zeneca Ltd	Chemical process

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3798276A (en) *	1972-03-14	1974-03-19	H Bayer	Herbicidal 4-trifluoromethyl-4'-nitrodiphenyl ethers
US4046798A (en) *	1973-02-12	1977-09-06	Rohm And Haas Company	Herbicidal 4-trifluoromethyl-4'nitrodiphenyl ethers
US3928416A (en) *	1972-03-14	1975-12-23	Rohm & Haas	Herbicidal 4-trifluoromethyl-4{40 nitrodiphenyl ethers
CA1079303A (en) *	1973-02-12	1980-06-10	Horst O. Bayer	Herbicidal 4-trifluoromethyl-4'-nitrodiphenyl ethers
US3979437A (en) *	1973-09-19	1976-09-07	Mobil Oil Corporation	Substituted phenoxybenzoic acids and derivatives thereof
US4031131A (en) *	1975-09-29	1977-06-21	Rohm And Haas Company	Process for preparing phenoxybenzoic acids
EP0022610B1 (en) *	1979-06-22	1986-09-03	Rhone-Poulenc Agrochimie	Process for preparing 2-nitro-5-(substituted-phenoxy) benzoic acids and salts thereof
EP0023100B1 (en) *	1979-07-18	1982-11-10	Imperial Chemical Industries Plc	Herbicidal compositions comprising a diphenyl ether compound in admixture with another herbicide

1981
- 1981-07-27 US US06/286,996 patent/US4405805A/en not_active Expired - Fee Related
1982
- 1982-07-02 FR FR8211791A patent/FR2510102B1/fr not_active Expired
- 1982-07-20 IL IL66357A patent/IL66357A/xx unknown
- 1982-07-23 IT IT22547/82A patent/IT1156314B/it active
- 1982-07-23 PL PL1982237635A patent/PL144334B1/pl unknown
- 1982-07-26 JP JP57130218A patent/JPS5838235A/ja active Pending
- 1982-07-26 GB GB08221571A patent/GB2103214B/en not_active Expired
- 1982-07-26 PT PT75324A patent/PT75324B/pt unknown
- 1982-07-26 BE BE0/208678A patent/BE893942A/fr not_active IP Right Cessation
- 1982-07-26 LU LU84297A patent/LU84297A1/fr unknown
- 1982-07-26 DE DE19823227846 patent/DE3227846A1/de not_active Withdrawn
- 1982-07-26 HU HU822398A patent/HU190694B/hu not_active IP Right Cessation
- 1982-07-26 IE IE1784/82A patent/IE54596B1/en unknown
- 1982-07-26 ES ES514354A patent/ES514354A0/es active Granted
- 1982-07-26 NL NL8202995A patent/NL8202995A/nl not_active Application Discontinuation
- 1982-07-26 CA CA000408050A patent/CA1203811A/en not_active Expired
- 1982-07-26 CH CH4540/82A patent/CH652710A5/fr not_active IP Right Cessation
- 1982-07-26 DK DK333582A patent/DK333582A/da not_active Application Discontinuation
- 1982-07-26 BR BR8204352A patent/BR8204352A/pt unknown
- 1982-07-27 DD DD82241978A patent/DD202423A5/de unknown
- 1982-07-27 RO RO108285A patent/RO85386B/ro unknown
- 1982-07-27 KR KR8203347A patent/KR890001806B1/ko not_active Expired
1983
- 1983-06-16 ES ES523320A patent/ES8500210A1/es not_active Expired

Also Published As

Publication number	Publication date
DK333582A (da)	1983-01-28
CA1203811A (en)	1986-04-29
IL66357A0 (en)	1982-11-30
NL8202995A (nl)	1983-02-16
GB2103214B (en)	1986-07-02
IE54596B1 (en)	1989-12-06
PL144334B1 (en)	1988-05-31
KR840000478A (ko)	1984-02-22
ES8400386A1 (es)	1983-10-16
PT75324B (fr)	1985-11-29
PL237635A1 (en)	1984-08-13
ES523320A0 (es)	1984-10-01
BR8204352A (pt)	1983-07-19
FR2510102A1 (fr)	1983-01-28
RO85386A (ro)	1984-11-25
KR890001806B1 (ko)	1989-05-23
HU190694B (en)	1986-10-28
RO85386B (ro)	1984-11-30
IE821784L (en)	1983-01-27
GB2103214A (en)	1983-02-16
IT8222547A1 (it)	1984-01-23
CH652710A5 (fr)	1985-11-29
BE893942A (fr)	1983-01-26
IL66357A (en)	1986-04-29
FR2510102B1 (fr)	1985-10-11
DD202423A5 (de)	1983-09-14
IT8222547A0 (it)	1982-07-23
IT1156314B (it)	1987-02-04
JPS5838235A (ja)	1983-03-05
ES514354A0 (es)	1983-10-16
PT75324A (fr)	1982-08-01
US4405805A (en)	1983-09-20
DE3227846A1 (de)	1983-02-10
ES8500210A1 (es)	1984-10-01

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