DK3052463T3 - Fremgangsmåde til at hydrolysere 1,2,4-trihalobenzen - Google Patents
Fremgangsmåde til at hydrolysere 1,2,4-trihalobenzen Download PDFInfo
- Publication number
- DK3052463T3 DK3052463T3 DK14784411.2T DK14784411T DK3052463T3 DK 3052463 T3 DK3052463 T3 DK 3052463T3 DK 14784411 T DK14784411 T DK 14784411T DK 3052463 T3 DK3052463 T3 DK 3052463T3
- Authority
- DK
- Denmark
- Prior art keywords
- formula
- approx
- compound
- optionally
- alkali metal
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 41
- 230000003301 hydrolyzing effect Effects 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims description 69
- 229910052783 alkali metal Inorganic materials 0.000 claims description 30
- 239000003960 organic solvent Substances 0.000 claims description 20
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 19
- -1 alkali metal sulfite Chemical class 0.000 claims description 17
- 150000001340 alkali metals Chemical class 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000011734 sodium Substances 0.000 claims description 14
- 229910052708 sodium Inorganic materials 0.000 claims description 13
- 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 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 10
- 229910052700 potassium Inorganic materials 0.000 claims description 10
- 239000011591 potassium Substances 0.000 claims description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 68
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 58
- 238000006243 chemical reaction Methods 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 description 25
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 25
- 239000005504 Dicamba Substances 0.000 description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 239000000047 product Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000007065 Kolbe-Schmitt synthesis reaction Methods 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- QKMNFFSBZRGHDJ-UHFFFAOYSA-N 1,4-dichloro-2-methoxybenzene Chemical compound COC1=CC(Cl)=CC=C1Cl QKMNFFSBZRGHDJ-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 229940031826 phenolate Drugs 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 235000011149 sulphuric acid Nutrition 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- VISJRVXHPNMYRH-UHFFFAOYSA-N 1,2-dichloro-4-methoxybenzene Chemical compound COC1=CC=C(Cl)C(Cl)=C1 VISJRVXHPNMYRH-UHFFFAOYSA-N 0.000 description 4
- CICQUFBZCADHHX-UHFFFAOYSA-N 2,4-dichloro-1-methoxybenzene Chemical compound COC1=CC=C(Cl)C=C1Cl CICQUFBZCADHHX-UHFFFAOYSA-N 0.000 description 4
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 4
- WDNBURPWRNALGP-UHFFFAOYSA-N 3,4-Dichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1 WDNBURPWRNALGP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000006473 carboxylation reaction Methods 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical group ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 4
- 230000020477 pH reduction Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- FKIKPQHMWFZFEB-UHFFFAOYSA-N 3,6-dichloro-2-hydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C(Cl)=CC=C1Cl FKIKPQHMWFZFEB-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 230000021523 carboxylation Effects 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-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 compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001734 carboxylic acid salts Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- IWIHHDMQUPPQQM-UHFFFAOYSA-N ClC1=C(C(C(=O)O)=C(C=C1)Cl)O.[K].[K] Chemical compound ClC1=C(C(C(=O)O)=C(C=C1)Cl)O.[K].[K] IWIHHDMQUPPQQM-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/02—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- 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
- A01N37/36—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (10)
1. Fremgangsmåde til at tilvejebringe en forbindelse med formlen (I) I
hvor Hal er et halogen, hvilken fremgangsmåde omfatter et trin med at omsætte en forbindelse med formlen (II)
II hvor Hal er defineret som ovenfor, med et alkalimetalsulfit med formlen X2SO3 og en alkalimetalhydroxid med formlen YOH, hvor X og Y uafhængigt er valgt blandt et alkalimetal.
2. Fremgangsmåden ifølge krav 1, hvilken fremgangsmåde udføres i nærvær af vand, eventuelt i yderligere tilstedeværelse af en Ci-C4_alkohol, og eventuelt i fravær af organiske opløsningsmidler bortset fra den eventuelle tilstedeværelse af en Ci-C4-alkohol, og yderligere eventuelt i fuldstændigt fravær af organiske opløsningsmidler.
3. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 3, hvor ca. en molækvivalent af forbindelsen med formlen (II) omsættes i nærvær af (a) ca. 1,0 til ca. 1,4, eventuelt ca. 1,1 til ca. 1,3 molækvivalenter af et alkalimetalsulfit med formlen X2SO3, hvor X er som defineret i krav 1; og/eller (b) ca. 0,5 til ca. 4,0, eventuelt ca. 1,2 til ca. 2,0 molækvivalenter af en alkalimetalhydroxid med formlen YOH, hvor Y er som defineret i krav 1; og/eller (c) ca. 20 til ca. 40, eventuelt ca. 25 til 38 molækvivalenter vand; og/eller (d) eventuelt op til 3 molækvivalenter, og yderligere eventuelt op til 2 molækvivalenter af en Ci-C4-alkohol, hvor der eventuelt bortset fra Ci-C4-alkoholen ikke er yderligere organisk opløsningsmiddel til stede.
4. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, hvor trinnet med at omsætte forbindelsen med formlen (II) udføres ved (a) en temperatur på mindst ca. 250 °C, eventuelt på mindst ca. 265 °C, yderligere eventuelt på mindst ca. 270 °C, såsom ca. 250 °C til ca. 290 °C, ca. 265 °C til ca. 290 °C, eller ca. 270 °C til ca. 290 °C; og/eller (b) et tryk på ca. 2050 kPa til ca. 5600 kPa, eventuelt på ca. 3500 kPa til ca. 5370 kPa, yderligere eventuelt på ca. 4820 kPa til ca. 5350 kPa.
5. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 4, der yderligere omfatter et trin med at omsætte forbindelsen med formlen (I) til at opnå en forbindelse med formlen ΓΠΓΠ III
hvor Hal er som defineret i krav 1, og R1 er et alkalimetal.
6. Fremgangsmåden ifølge krav 5, hvilket trin med at omsætte forbindelsen med formlen (I) til at opnå en forbindelse med formlen (III) udføres i nærvær af en alkalimetalhydroxid og carbondioxid.
7. Fremgangsmåde ifølge krav 5 eller 6, der yderligere omfatter et trin med at omsætte forbindelsen med formlen (III) til at opnå en forbindelse med formlen (IV)
IV hvor R2 er - (Ci-C4) -alkyl, R1' er et alkalimetal eller -(C1-C4)-alkyl, og Hal er som defineret i krav 1.
8. Fremgangsmåden ifølge krav 7, der yderligere omfatter et trin med at omsætte forbindelsen med formlen (IV) til at opnå en forbindelse med formlen (V)
V hvor R2 og Hal er som defineret i krav 7.
9. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, hvor (a) Hal er valgt blandt F, Cl, Br og I, eventuelt fra Cl og Br, og endvidere eventuelt er Cl; og/eller (b) X og Y er uafhængigt udvalgt fra natrium eller kalium, og eventuelt er begge natrium; og/eller (c) R1 er valgt blandt natrium og kalium, og eventuelt er kalium; og/eller (d) R1' er valgt blandt natrium og kalium, eller R1' er udvalgt blandt ethyl og methyl, og eventuelt er methyl.
10. Fremgangsmåde ifølge krav 8 eller 9, hvor forbindelsen med formlen (V) er
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361886667P | 2013-10-04 | 2013-10-04 | |
| EP13191083 | 2013-10-31 | ||
| PCT/EP2014/070509 WO2015049160A1 (en) | 2013-10-04 | 2014-09-25 | Process for hydrolyzing 1,2,4-trihalobenzene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK3052463T3 true DK3052463T3 (da) | 2017-06-12 |
Family
ID=49488511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK14784411.2T DK3052463T3 (da) | 2013-10-04 | 2014-09-25 | Fremgangsmåde til at hydrolysere 1,2,4-trihalobenzen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9643909B2 (da) |
| EP (1) | EP3052463B1 (da) |
| CN (1) | CN105593197B (da) |
| DK (1) | DK3052463T3 (da) |
| WO (1) | WO2015049160A1 (da) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK3052462T3 (da) | 2013-10-04 | 2018-12-17 | Basf Se | Selektiv hydrolyse og alcoholyse af chlorerede benzener |
| WO2015086698A1 (en) | 2013-12-11 | 2015-06-18 | Basf Se | Process for providing dihalogen substituted salicylic acid derivatives |
| WO2015091045A1 (en) | 2013-12-18 | 2015-06-25 | BASF Agro B.V. | Process for the preparation of substituted phenoxyphenyl ketones |
| US10023590B2 (en) | 2014-04-17 | 2018-07-17 | Basf Se | Substituted pyridine compounds having herbicidal activity |
| AR100506A1 (es) | 2014-05-19 | 2016-10-12 | Basf Se | Proceso de obtención del herbicida dicamba |
| WO2016062814A1 (en) | 2014-10-24 | 2016-04-28 | Basf Se | Substituted pyridine compounds having herbicidal activity |
| BR112017023932A2 (pt) | 2015-05-08 | 2018-07-17 | Basf Agro Bv | processo para a preparação de epóxido de terpinoleno |
| CN107848922A (zh) | 2015-05-08 | 2018-03-27 | 巴斯夫农业公司 | 柠檬烯‑4‑醇的制备方法 |
| CN106083530B (zh) * | 2016-06-12 | 2019-02-26 | 江苏扬农化工集团有限公司 | 一种合成2,5-二氯苯酚的方法 |
| WO2017215928A1 (en) | 2016-06-15 | 2017-12-21 | BASF Agro B.V. | Process for the epoxidation of a tetrasubstituted alkene |
| US10640477B2 (en) | 2016-06-15 | 2020-05-05 | BASF Agro B.V. | Process for the epoxidation of a tetrasubstituted alkene |
| CN108046996B (zh) * | 2017-12-12 | 2021-04-09 | 安徽国星生物化学有限公司 | 一种2,5-二氯苯酚连续化合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2799714A (en) * | 1955-01-24 | 1957-07-16 | Dow Chemical Co | Method of hydrolyzing di-and trichlorobenzenes |
| US4094913A (en) * | 1977-01-07 | 1978-06-13 | Velsicol Chemical Corporation | Process for the preparation of 2,5-dichlorophenol |
| FR2946339B1 (fr) * | 2009-06-08 | 2013-02-08 | Centre Nat Rech Scient | Procede d'hydroxydation de composes amples halogenes |
| CN102887817B (zh) * | 2012-09-11 | 2015-04-01 | 浙江永太科技股份有限公司 | 一种合成2,3,4,5,6-五氟苯酚的新方法 |
-
2014
- 2014-09-25 EP EP14784411.2A patent/EP3052463B1/en not_active Not-in-force
- 2014-09-25 US US15/026,715 patent/US9643909B2/en active Active
- 2014-09-25 DK DK14784411.2T patent/DK3052463T3/da active
- 2014-09-25 CN CN201480054383.9A patent/CN105593197B/zh active Active
- 2014-09-25 WO PCT/EP2014/070509 patent/WO2015049160A1/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| CN105593197B (zh) | 2018-07-13 |
| US20160251294A1 (en) | 2016-09-01 |
| CN105593197A (zh) | 2016-05-18 |
| EP3052463A1 (en) | 2016-08-10 |
| US9643909B2 (en) | 2017-05-09 |
| WO2015049160A1 (en) | 2015-04-09 |
| EP3052463B1 (en) | 2017-03-01 |
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