DK2828268T3 - Fremgangsmåde til fremstilling af dithiin-tetracarboximider - Google Patents
Fremgangsmåde til fremstilling af dithiin-tetracarboximider Download PDFInfo
- Publication number
- DK2828268T3 DK2828268T3 DK13713113.2T DK13713113T DK2828268T3 DK 2828268 T3 DK2828268 T3 DK 2828268T3 DK 13713113 T DK13713113 T DK 13713113T DK 2828268 T3 DK2828268 T3 DK 2828268T3
- Authority
- DK
- Denmark
- Prior art keywords
- process according
- thionyl chloride
- formula
- alkyl
- reaction mixture
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 50
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 74
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- 239000011541 reaction mixture Substances 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 239000003085 diluting agent Substances 0.000 claims description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 12
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 12
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical class NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 239000007789 gas Substances 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 8
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 7
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 3
- 229940117389 dichlorobenzene Drugs 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical compound NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- 150000003738 xylenes Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- RIYVKHUVXPAOPS-UHFFFAOYSA-N dithiine Chemical compound S1SC=CC=C1 RIYVKHUVXPAOPS-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 11
- -1 sulphur compound Chemical class 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ALWDVDJEMWKXEY-UHFFFAOYSA-N n'-methylbutanediamide Chemical compound CNC(=O)CCC(N)=O ALWDVDJEMWKXEY-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000012958 reprocessing Methods 0.000 description 2
- BTNMOVUCMBMKNZ-UHFFFAOYSA-N 1-propylpyrrolidine-2,5-dione Chemical compound CCCN1C(=O)CCC1=O BTNMOVUCMBMKNZ-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- KVBAKSQRUXXHCK-UHFFFAOYSA-N 3,4-Dichloro-5-hydroxy-2H-pyrrol-2-one Chemical class ClC1=C(Cl)C(=O)NC1=O KVBAKSQRUXXHCK-UHFFFAOYSA-N 0.000 description 1
- AGULWIQIYWWFBJ-UHFFFAOYSA-N 3,4-dichlorofuran-2,5-dione Chemical compound ClC1=C(Cl)C(=O)OC1=O AGULWIQIYWWFBJ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GJEQKNYYNCWFKJ-UHFFFAOYSA-N n'-cyclohexylbutanediamide Chemical compound NC(=O)CCC(=O)NC1CCCCC1 GJEQKNYYNCWFKJ-UHFFFAOYSA-N 0.000 description 1
- WUMODJWGOJWRDW-UHFFFAOYSA-N n'-tert-butylbutanediamide Chemical compound CC(C)(C)NC(=O)CCC(N)=O WUMODJWGOJWRDW-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrrole Compounds (AREA)
Claims (11)
1. Fremgangsmåde til fremstilling af dithiin- tetracarboximider med den almene formel (I)
(i) hvor R1 og R2 er ens eller forskellige og står for hydrogen, for i givet fald en eller flere gange med halogen, -OR3, -COR4 substitueret Ci-Cs-alkyl, i givet fald en eller flere gange med halogen, Ci-C4~alkyl eller C:-C4-halogenalkyl substitueret C3-C7-cycloalkyl, hver især i givet fald en eller flere gange med halogen, Ci-Ch-alkyl, Ci-C4-halogenalkyl, -COR4 eller sulfonyla-mino substitueret aryl eller aryl-(Ci-C4-alkyl), R3 står for hydrogen, Ci-C4-alkyl, Ci-C4-alkylcarbonyl eller for i givet fald en eller flere gange med halogen, Ci-C4-alkyl eller Ci-CU-halogenalkyl substitueret aryl, R4 står for hydroxy, Ci-C4-alkyl eller Ci-C4-alkoxy, kendetegnet ved, at ravsyremonoamider med formel (VI)
(vi) (VI) hvor R står for R1 eller R2, omsættes med thionylchlorid til en reaktionsblanding, den opståede reaktionsblanding i et andet trin (2) opvarmes, og omsætningen af reaktionsblandingen til dithiin- tetracarboximiderne efterfølgende sker i det tredje trin (3), idet i det mindste trin (2) gennemføres kontinuerligt.
2. Fremgangsmåde ifølge krav 1, kendetegnet ved, at den samlede mængde thionylchlorid (z) er mellem 2,5 og 20 mol pr. mol ravsyremonoamid med formel (VI), idet z defineres med forbindelsen z = x + y og z står for den samlede mængde thionylchlorid (mol thionylchlo-rid pr. mol ravsyreamid med den almene formel (VI)) i det to første trin (1) og (2), x står for mængden af thionylchlorid i trin (1), og y står for den i trin (2) yderligere anvendte mængde thionylchlorid.
3. Fremgangsmåde ifølge krav 2, kendetegnet ved, at værdien z er mellem 2,5 og 14 mol pr. mol ravsyremonoamid med formel (VI) .
4. Fremgangsmåde ifølge krav 2, kendetegnet ved, at værdien z er mellem 2,5 og 9 mol pr. mol ravsyremonoamid med formel (VI) .
5. Fremgangsmåde ifølge krav 2, kendetegnet ved, at mængden af thionylchlorid x i trin (1) er mellem 1 og 20 mol pr. mol ravsyremonoamid med formel (VI).
6. Fremgangsmåde ifølge krav 1, kendetegnet ved, at omsætningen af reaktionsblandingen til dithiin-tetracarboximiderne sker i tredje trin (3) i fremgangsmåden, når gasudviklingen er klinget af i trin (2).
7. Fremgangsmåde ifølge krav 6, kendetegnet ved, at det opnåede mellemprodukt opløses i et fortyndingsmiddel, blandes med vand og ved opvarmning i denne blanding omdannes til dithiin-tetracarboximiderne med formel (I).
8. Fremgangsmåde ifølge krav 1, kendetegnet ved, at trin (1) gennemføres kontinuerligt.
9. Fremgangsmåde ifølge krav 1, kendetegnet ved, at der i trin (3) anvendes et organisk opløsningsmiddel, som i det mindste delvist kan blandes med vand.
10. Fremgangsmåde ifølge krav 1, kendetegnet ved, at der i trin (3) som opløsningsmiddel anvendes vand, dimethylsulfoxid, sulfolan, alkoholer såsom methanol, ethanol, propanol, isopropanol, 1-butanol, 2-butanol, isobutanol, tertiærbutanol, 1- pentanol, cyclopentanol, cyclohexanol, ethylenglykol, ethy-lenglykol-monomethylether, carbonhydrider såsom hexan, heptan, cyclohexan, methylcyclohexan, toluen, xylener, mesitylen, chlorbenzen, dichlorbenzen, nitrobenzen, estere såsom eddike-syremethylester, eddikesyreethylester, amider såsom formamid, N,N-dimethylformamid; N,N-dimethylacetamid, N- methylpyrrolidon, ethere såsom methyl-tert-butylether, tetra-hydrofuran, 1,4-dioxan, nitriler såsom acetonitril, propio-nitril, butyronitril, benzonitril, ketoner såsom acetone, methyl-ethylketon, methyl-isobutylketon, pinakolon, carboxylsyrer såsom myresyre, eddikesyre, propionsyre eller blandinger af disse fortyndingsmidler.
11. Fremgangsmåde ifølge krav 1, kendetegnet ved, at trin (3) gennemføres ved en reaktionstemperatur mellem 40°C og 120°C.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12161009.1A EP2641908A1 (de) | 2012-03-23 | 2012-03-23 | Verfahren zur Herstellung von Dithiin-tetracarboximiden |
| PCT/EP2013/055565 WO2013139736A1 (de) | 2012-03-23 | 2013-03-18 | Verfahren zur herstellung von dithiin-tetracarboximiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2828268T3 true DK2828268T3 (da) | 2017-03-06 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK13713113.2T DK2828268T3 (da) | 2012-03-23 | 2013-03-18 | Fremgangsmåde til fremstilling af dithiin-tetracarboximider |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9365586B2 (da) |
| EP (2) | EP2641908A1 (da) |
| JP (1) | JP6209583B2 (da) |
| KR (1) | KR20140146075A (da) |
| CN (1) | CN104203957B (da) |
| DK (1) | DK2828268T3 (da) |
| EA (1) | EA201491745A1 (da) |
| ES (1) | ES2617827T3 (da) |
| IL (1) | IL234526A (da) |
| IN (1) | IN2014DN07166A (da) |
| MX (1) | MX350921B (da) |
| TW (1) | TWI568738B (da) |
| WO (1) | WO2013139736A1 (da) |
| ZA (1) | ZA201406188B (da) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140256956A1 (en) * | 2011-10-13 | 2014-09-11 | Bayer Intellectual Property Gmbh | Method for producing dithine tetracarboximides |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3364229A (en) | 1964-01-30 | 1968-01-16 | Shell Oil Co | 1, 4 dithiin-2, 3, 5, 6-tetracarboximides and process for their preparation |
| PL143804B2 (en) | 1985-10-15 | 1988-03-31 | Univ Lodzki | Process for preparing novel derivatives of 2,6-diphenyl-2,3,6,7-tetrahydro-1h,5h-1,4-dithiin-/2,3-c:5,6-c/-diprolo-1,3,5,7-tetraon substituted in phenyl ring |
| JP3530702B2 (ja) | 1997-03-06 | 2004-05-24 | 京セラミタ株式会社 | ジチオマレイン酸イミド誘導体を用いた電子写真感光体 |
| US7855715B1 (en) * | 2005-07-27 | 2010-12-21 | James Harrison Bowen | Switch with depth and lateral articulation detection using optical beam |
| CN100402533C (zh) * | 2006-07-05 | 2008-07-16 | 浙江工业大学 | 苯并萘并二噻英并噻蒽六酮作为三阶非线性光材的应用 |
| BRPI0920122B1 (pt) * | 2008-10-15 | 2017-12-19 | Bayer Intellectual Property Gmbh | Ditiin-tetracarboximides and their uses for combating phytopathogenic fungi |
| AR077956A1 (es) * | 2009-09-14 | 2011-10-05 | Bayer Cropscience Ag | Combinaciones de compuestos activos |
| UA108216C2 (uk) * | 2009-11-17 | 2015-04-10 | Баєр Кропсаєнс Аг | Комбінації активних сполук |
| EP2558473B1 (de) * | 2010-04-14 | 2016-09-07 | Bayer Intellectual Property GmbH | Verfahren zur herstellung von dithiin-tetracarboximiden |
| CN102892769B (zh) * | 2010-04-14 | 2015-04-01 | 拜尔农作物科学股份公司 | 制备二噻烯-四羧基-二酰亚胺的方法 |
| AR084959A1 (es) * | 2010-04-14 | 2013-07-24 | Bayer Cropscience Ag | Combinaciones de compuestos activos contra hongos fitopatogenos y composicion fungicida |
| CA2796166A1 (en) * | 2010-04-14 | 2011-10-20 | Bayer Intellectual Property Gmbh | Active compound combinations |
| WO2011138281A2 (de) * | 2010-05-06 | 2011-11-10 | Bayer Cropscience Ag | Verfahren zur herstellung von dithiin-tetracarboxy-diimiden |
| KR20130112719A (ko) * | 2010-05-21 | 2013-10-14 | 바이엘 크롭사이언스 아게 | 디티인-테트라카복시-디이미드의 제조방법 |
| PH12013500415A1 (en) * | 2010-09-03 | 2013-04-15 | Bayer Ip Gmbh | Dithiin-tetra(thio) carboximides for controlling phytopathogenic fungi |
| US20140256956A1 (en) * | 2011-10-13 | 2014-09-11 | Bayer Intellectual Property Gmbh | Method for producing dithine tetracarboximides |
-
2012
- 2012-03-23 EP EP12161009.1A patent/EP2641908A1/de not_active Ceased
-
2013
- 2013-03-08 TW TW102108170A patent/TWI568738B/zh not_active IP Right Cessation
- 2013-03-18 IN IN7166DEN2014 patent/IN2014DN07166A/en unknown
- 2013-03-18 ES ES13713113.2T patent/ES2617827T3/es active Active
- 2013-03-18 WO PCT/EP2013/055565 patent/WO2013139736A1/de not_active Ceased
- 2013-03-18 CN CN201380015688.4A patent/CN104203957B/zh not_active Expired - Fee Related
- 2013-03-18 KR KR1020147026137A patent/KR20140146075A/ko not_active Abandoned
- 2013-03-18 MX MX2014011160A patent/MX350921B/es active IP Right Grant
- 2013-03-18 EA EA201491745A patent/EA201491745A1/ru unknown
- 2013-03-18 DK DK13713113.2T patent/DK2828268T3/da active
- 2013-03-18 JP JP2015500872A patent/JP6209583B2/ja not_active Expired - Fee Related
- 2013-03-18 US US14/385,648 patent/US9365586B2/en not_active Expired - Fee Related
- 2013-03-18 EP EP13713113.2A patent/EP2828268B1/de not_active Not-in-force
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2014
- 2014-08-22 ZA ZA2014/06188A patent/ZA201406188B/en unknown
- 2014-09-08 IL IL234526A patent/IL234526A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| TWI568738B (zh) | 2017-02-01 |
| US9365586B2 (en) | 2016-06-14 |
| MX350921B (es) | 2017-09-25 |
| IN2014DN07166A (da) | 2015-04-24 |
| JP6209583B2 (ja) | 2017-10-04 |
| JP2015510911A (ja) | 2015-04-13 |
| MX2014011160A (es) | 2014-12-10 |
| WO2013139736A1 (de) | 2013-09-26 |
| EP2828268B1 (de) | 2016-12-14 |
| TW201350490A (zh) | 2013-12-16 |
| ZA201406188B (en) | 2015-11-25 |
| ES2617827T3 (es) | 2017-06-19 |
| EA201491745A1 (ru) | 2015-03-31 |
| EP2828268A1 (de) | 2015-01-28 |
| US20150045561A1 (en) | 2015-02-12 |
| IL234526A (en) | 2016-12-29 |
| KR20140146075A (ko) | 2014-12-24 |
| CN104203957A (zh) | 2014-12-10 |
| CN104203957B (zh) | 2016-09-28 |
| EP2641908A1 (de) | 2013-09-25 |
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