NO773001L - Fremgangsmaate ved fremstilling av 2,3-dikloranisol - Google Patents
Fremgangsmaate ved fremstilling av 2,3-dikloranisolInfo
- Publication number
- NO773001L NO773001L NO773001A NO773001A NO773001L NO 773001 L NO773001 L NO 773001L NO 773001 A NO773001 A NO 773001A NO 773001 A NO773001 A NO 773001A NO 773001 L NO773001 L NO 773001L
- Authority
- NO
- Norway
- Prior art keywords
- reaction
- approx
- methanol
- sodium
- alkoxide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- HFEASCCDHUVYKU-UHFFFAOYSA-N 1,2-dichloro-3-methoxybenzene Chemical compound COC1=CC=CC(Cl)=C1Cl HFEASCCDHUVYKU-UHFFFAOYSA-N 0.000 claims abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 49
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 20
- 150000004703 alkoxides Chemical class 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 11
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- AGHANLSBXUWXTB-UHFFFAOYSA-N tienilic acid Chemical compound ClC1=C(Cl)C(OCC(=O)O)=CC=C1C(=O)C1=CC=CS1 AGHANLSBXUWXTB-UHFFFAOYSA-N 0.000 claims description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 claims 2
- LPOFCDCHMSXJDK-UHFFFAOYSA-N (2,3-dichloro-4-methoxyphenyl)-thiophen-2-ylmethanone Chemical compound ClC1=C(Cl)C(OC)=CC=C1C(=O)C1=CC=CS1 LPOFCDCHMSXJDK-UHFFFAOYSA-N 0.000 claims 1
- YIYBRXKMQFDHSM-UHFFFAOYSA-N 2,2'-Dihydroxybenzophenone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1O YIYBRXKMQFDHSM-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000005224 alkoxybenzenes Chemical class 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- -1 potassium 2,3-dichloroanisole Chemical compound 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- KZLMCDNAVVJKPX-UHFFFAOYSA-N 1,3-dichloro-2-methoxybenzene Chemical compound COC1=C(Cl)C=CC=C1Cl KZLMCDNAVVJKPX-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000012485 toluene extract Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- IQEXVQXICRQRFK-UHFFFAOYSA-N C(CCCC)OCCCCC.[K] Chemical compound C(CCCC)OCCCCC.[K] IQEXVQXICRQRFK-UHFFFAOYSA-N 0.000 description 1
- GAAICBWIRTXHNU-UHFFFAOYSA-N C(CCCCCC)OCCCCCCC.[Na] Chemical compound C(CCCCCC)OCCCCCCC.[Na] GAAICBWIRTXHNU-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 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 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000007080 aromatic substitution reaction Methods 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- 229940112669 cuprous oxide Drugs 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
- GEVUHWKYEWTTMW-UHFFFAOYSA-N n,n-dimethylacetamide;methanol Chemical compound OC.CN(C)C(C)=O GEVUHWKYEWTTMW-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- AWDMDDKZURRKFG-UHFFFAOYSA-N potassium;propan-1-olate Chemical compound [K+].CCC[O-] AWDMDDKZURRKFG-UHFFFAOYSA-N 0.000 description 1
- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229960000356 tienilic acid Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
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)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/719,795 US4057585A (en) | 1976-09-02 | 1976-09-02 | Method of preparing 2,3-dichloroanisole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO773001L true NO773001L (no) | 1978-03-03 |
Family
ID=24891397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO773001A NO773001L (no) | 1976-09-02 | 1977-08-30 | Fremgangsmaate ved fremstilling av 2,3-dikloranisol |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4057585A (xx) |
| JP (1) | JPS5331633A (xx) |
| AT (1) | AT359476B (xx) |
| AU (1) | AU510764B2 (xx) |
| BE (1) | BE857606A (xx) |
| BG (1) | BG28842A3 (xx) |
| CA (1) | CA1081260A (xx) |
| CH (1) | CH633245A5 (xx) |
| CS (1) | CS196385B2 (xx) |
| DD (1) | DD132263A5 (xx) |
| DE (1) | DE2734809A1 (xx) |
| DK (1) | DK345477A (xx) |
| ES (1) | ES461282A1 (xx) |
| FI (1) | FI772434A (xx) |
| GR (1) | GR63604B (xx) |
| IE (1) | IE45375B1 (xx) |
| IL (1) | IL52643A (xx) |
| IN (1) | IN147959B (xx) |
| IT (1) | IT1114911B (xx) |
| LU (1) | LU78042A1 (xx) |
| NL (1) | NL7709594A (xx) |
| NO (1) | NO773001L (xx) |
| PH (1) | PH13820A (xx) |
| PL (1) | PL107727B1 (xx) |
| PT (1) | PT66879B (xx) |
| RO (1) | RO74536A (xx) |
| SE (1) | SE428558B (xx) |
| YU (1) | YU194977A (xx) |
| ZA (1) | ZA774205B (xx) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2478077A1 (fr) * | 1980-03-12 | 1981-09-18 | Rhone Poulenc Ind | Procede de preparation de chloroalkoxybenzenes |
| JP5476568B2 (ja) * | 2008-01-16 | 2014-04-23 | カーリットホールディングス株式会社 | チオフェン誘導体の製造方法 |
| FR2950882B1 (fr) * | 2010-01-14 | 2012-01-13 | Commissariat Energie Atomique | Procede de synthese du 3,5-dichloroanisole a partir du 1,3,5-trichlorobenzene |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2615823A (en) * | 1950-03-30 | 1952-10-28 | Niagara Alkali Company | Bactericidal and fungicidal composition |
| US2803664A (en) * | 1954-10-14 | 1957-08-20 | Ethyl Corp | Preparation of trichlorophenylalkyl ethers |
| DE2210254A1 (de) * | 1972-03-03 | 1973-09-06 | Dynamit Nobel Ag | Verfahren zur herstellung von phenolaethern bzw. phenolen |
-
1976
- 1976-09-02 US US05/719,795 patent/US4057585A/en not_active Expired - Lifetime
-
1977
- 1977-07-13 ZA ZA00774205A patent/ZA774205B/xx unknown
- 1977-08-01 AU AU27520/77A patent/AU510764B2/en not_active Expired
- 1977-08-02 DE DE19772734809 patent/DE2734809A1/de not_active Ceased
- 1977-08-02 IT IT26428/77A patent/IT1114911B/it active
- 1977-08-02 PT PT66879A patent/PT66879B/pt unknown
- 1977-08-02 ES ES461282A patent/ES461282A1/es not_active Expired
- 1977-08-02 DK DK345477A patent/DK345477A/da not_active Application Discontinuation
- 1977-08-03 IL IL52643A patent/IL52643A/xx active IP Right Revival
- 1977-08-03 JP JP9374077A patent/JPS5331633A/ja active Pending
- 1977-08-04 AT AT573177A patent/AT359476B/de active
- 1977-08-08 DD DD7700200489A patent/DD132263A5/xx unknown
- 1977-08-08 PH PH20095A patent/PH13820A/en unknown
- 1977-08-09 YU YU01949/77A patent/YU194977A/xx unknown
- 1977-08-09 BE BE180011A patent/BE857606A/xx not_active IP Right Cessation
- 1977-08-12 FI FI772434A patent/FI772434A/fi not_active Application Discontinuation
- 1977-08-17 CH CH1009677A patent/CH633245A5/de not_active IP Right Cessation
- 1977-08-20 RO RO7791440A patent/RO74536A/ro unknown
- 1977-08-29 GR GR54254A patent/GR63604B/el unknown
- 1977-08-29 LU LU78042A patent/LU78042A1/xx unknown
- 1977-08-30 CS CS775662A patent/CS196385B2/cs unknown
- 1977-08-30 NO NO773001A patent/NO773001L/no unknown
- 1977-08-30 CA CA285,810A patent/CA1081260A/en not_active Expired
- 1977-08-30 BG BG037263A patent/BG28842A3/xx unknown
- 1977-08-30 PL PL1977200538A patent/PL107727B1/pl unknown
- 1977-08-31 NL NL7709594A patent/NL7709594A/xx not_active Application Discontinuation
- 1977-08-31 IE IE1815/77A patent/IE45375B1/en unknown
- 1977-08-31 SE SE7709805A patent/SE428558B/xx not_active IP Right Cessation
-
1978
- 1978-07-01 IN IN494/DEL/78A patent/IN147959B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL52643A0 (en) | 1977-10-31 |
| AT359476B (de) | 1980-11-10 |
| SE7709805L (sv) | 1978-03-03 |
| DE2734809A1 (de) | 1978-03-09 |
| CS196385B2 (en) | 1980-03-31 |
| JPS5331633A (en) | 1978-03-25 |
| ATA573177A (de) | 1980-04-15 |
| FI772434A (fi) | 1978-03-03 |
| IN147959B (xx) | 1980-08-23 |
| AU2752077A (en) | 1979-02-08 |
| IE45375L (en) | 1978-03-02 |
| BG28842A3 (en) | 1980-07-15 |
| RO74536A (ro) | 1980-11-30 |
| DK345477A (da) | 1978-03-03 |
| CA1081260A (en) | 1980-07-08 |
| US4057585A (en) | 1977-11-08 |
| DD132263A5 (de) | 1978-09-13 |
| GR63604B (en) | 1979-11-26 |
| YU194977A (en) | 1982-10-31 |
| ZA774205B (en) | 1978-05-30 |
| AU510764B2 (en) | 1980-07-10 |
| PT66879B (en) | 1979-01-24 |
| IT1114911B (it) | 1986-02-03 |
| IE45375B1 (en) | 1982-08-11 |
| PL107727B1 (pl) | 1980-02-29 |
| CH633245A5 (de) | 1982-11-30 |
| NL7709594A (nl) | 1978-03-06 |
| LU78042A1 (xx) | 1978-01-11 |
| PT66879A (en) | 1977-09-01 |
| BE857606A (fr) | 1978-02-09 |
| PL200538A1 (pl) | 1978-05-22 |
| SE428558B (sv) | 1983-07-11 |
| ES461282A1 (es) | 1978-05-01 |
| IL52643A (en) | 1980-01-31 |
| PH13820A (en) | 1980-10-03 |
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