HU214952B - Eljárás halogén-metil-benzoil-cianidok előállítására és új halogén-metil-benzoil-cianidok - Google Patents
Eljárás halogén-metil-benzoil-cianidok előállítására és új halogén-metil-benzoil-cianidok Download PDFInfo
- Publication number
- HU214952B HU214952B HU9400996A HU9400996A HU214952B HU 214952 B HU214952 B HU 214952B HU 9400996 A HU9400996 A HU 9400996A HU 9400996 A HU9400996 A HU 9400996A HU 214952 B HU214952 B HU 214952B
- Authority
- HU
- Hungary
- Prior art keywords
- cyanide
- chloromethyl
- priority
- benzyl
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 12
- -1 alkali metal cyanide Chemical class 0.000 claims abstract description 46
- 150000002825 nitriles Chemical class 0.000 claims abstract description 15
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims abstract description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 9
- 125000005997 bromomethyl group Chemical group 0.000 claims abstract description 8
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical group 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
- GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical compound N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- MVJIUTPZBDDMPF-UHFFFAOYSA-N 2-(chloromethyl)benzoyl cyanide Chemical compound ClCC1=CC=CC=C1C(=O)C#N MVJIUTPZBDDMPF-UHFFFAOYSA-N 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000003444 phase transfer catalyst Substances 0.000 claims description 4
- TXZFBHYDQGYOIT-UHFFFAOYSA-N 2-(chloromethyl)benzoyl chloride Chemical compound ClCC1=CC=CC=C1C(Cl)=O TXZFBHYDQGYOIT-UHFFFAOYSA-N 0.000 claims description 3
- 238000004508 fractional distillation Methods 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 239000000539 dimer Substances 0.000 claims description 2
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000003480 eluent Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 150000001805 chlorine compounds Chemical class 0.000 abstract description 3
- 239000003085 diluting agent Substances 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000011814 protection agent Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- GPGKNEKFDGOXPO-UHFFFAOYSA-N 4-phenyl-1h-pyrazole Chemical class C1=NNC=C1C1=CC=CC=C1 GPGKNEKFDGOXPO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- WTNJZZGDMZTEJH-UHFFFAOYSA-N butyl-bis(2-methoxyethyl)-(2-methylbutyl)azanium Chemical compound CCCC[N+](CCOC)(CCOC)CC(C)CC WTNJZZGDMZTEJH-UHFFFAOYSA-N 0.000 description 2
- XTBPKISXEWSOFF-UHFFFAOYSA-N butyl-cyclohexyl-diethylazanium Chemical compound CCCC[N+](CC)(CC)C1CCCCC1 XTBPKISXEWSOFF-UHFFFAOYSA-N 0.000 description 2
- DVJGEFVPCPNKOE-UHFFFAOYSA-N dibenzyl(dibutyl)azanium Chemical compound C=1C=CC=CC=1C[N+](CCCC)(CCCC)CC1=CC=CC=C1 DVJGEFVPCPNKOE-UHFFFAOYSA-N 0.000 description 2
- WDSYOBJACYKNAS-UHFFFAOYSA-N dibenzyl(dipropyl)azanium Chemical compound C=1C=CC=CC=1C[N+](CCC)(CCC)CC1=CC=CC=C1 WDSYOBJACYKNAS-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229940098221 silver cyanide Drugs 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- VEPTXBCIDSFGBF-UHFFFAOYSA-M tetrabutylazanium;fluoride;trihydrate Chemical compound O.O.O.[F-].CCCC[N+](CCCC)(CCCC)CCCC VEPTXBCIDSFGBF-UHFFFAOYSA-M 0.000 description 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- GPPHKQHTVOACJB-UHFFFAOYSA-N 1,1-dibenzylpiperidin-1-ium Chemical compound C1CCCC[N+]1(CC=1C=CC=CC=1)CC1=CC=CC=C1 GPPHKQHTVOACJB-UHFFFAOYSA-N 0.000 description 1
- BCMSMDHXUXDJFB-UHFFFAOYSA-N 1,1-dibutylpiperidin-1-ium Chemical compound CCCC[N+]1(CCCC)CCCCC1 BCMSMDHXUXDJFB-UHFFFAOYSA-N 0.000 description 1
- QIAZNDAYSCULMI-UHFFFAOYSA-N 1,1-dibutylpyrrolidin-1-ium Chemical compound CCCC[N+]1(CCCC)CCCC1 QIAZNDAYSCULMI-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- ZVSIWQHNVKJTKO-UHFFFAOYSA-N 1-(4,4-dimethylpentyl)piperidine Chemical compound CC(C)(C)CCCN1CCCCC1 ZVSIWQHNVKJTKO-UHFFFAOYSA-N 0.000 description 1
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- KHBGEFYLAWYYKZ-UHFFFAOYSA-N 1-benzyl-1,2-dibutyl-2-ethylpiperidin-1-ium Chemical compound CCCCC1(CC)CCCC[N+]1(CCCC)CC1=CC=CC=C1 KHBGEFYLAWYYKZ-UHFFFAOYSA-N 0.000 description 1
- VCCOAXNHVOKIPG-UHFFFAOYSA-N 1-benzyl-1-(2,3-dimethylbutyl)piperidin-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(C)C(C)C)CCCCC1 VCCOAXNHVOKIPG-UHFFFAOYSA-N 0.000 description 1
- ZVYCSCMFKSJWRZ-UHFFFAOYSA-N 1-benzyl-1-(2,3-dimethylbutyl)pyrrolidin-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(C)C(C)C)CCCC1 ZVYCSCMFKSJWRZ-UHFFFAOYSA-N 0.000 description 1
- VYRGQTHIYFUGBM-UHFFFAOYSA-N 1-benzyl-1-(2-butoxypropyl)piperidin-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(C)OCCCC)CCCCC1 VYRGQTHIYFUGBM-UHFFFAOYSA-N 0.000 description 1
- KCIJOXHNLNSEPJ-UHFFFAOYSA-N 1-benzyl-1-(2-ethylhexyl)piperidin-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(CC)CCCC)CCCCC1 KCIJOXHNLNSEPJ-UHFFFAOYSA-N 0.000 description 1
- ABPLFDBLEBHJSY-UHFFFAOYSA-N 1-benzyl-1-(2-methylbutyl)piperidin-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(C)CC)CCCCC1 ABPLFDBLEBHJSY-UHFFFAOYSA-N 0.000 description 1
- JWJBBPBGAYSNAM-UHFFFAOYSA-N 1-benzyl-1-(2-methylpentyl)piperidin-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(C)CCC)CCCCC1 JWJBBPBGAYSNAM-UHFFFAOYSA-N 0.000 description 1
- SESVPJUBLQDEPX-UHFFFAOYSA-N 1-benzyl-1-(3-ethoxy-2-methylpropyl)piperidin-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(C)COCC)CCCCC1 SESVPJUBLQDEPX-UHFFFAOYSA-N 0.000 description 1
- CFVYGSHDHAUMGW-UHFFFAOYSA-N 1-benzyl-1-(3-methylbutyl)piperidin-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CCC(C)C)CCCCC1 CFVYGSHDHAUMGW-UHFFFAOYSA-N 0.000 description 1
- YGWNKQAIMUAIRT-UHFFFAOYSA-N 1-benzyl-1-(oxan-2-ylmethyl)piperidin-1-ium Chemical compound C1CCCC[N+]1(CC=1C=CC=CC=1)CC1CCCCO1 YGWNKQAIMUAIRT-UHFFFAOYSA-N 0.000 description 1
- KFRRAPUKKARCJZ-UHFFFAOYSA-N 1-benzyl-1-[2-(2-methoxyethoxy)propyl]piperidin-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(C)OCCOC)CCCCC1 KFRRAPUKKARCJZ-UHFFFAOYSA-N 0.000 description 1
- OGGUGGJAFNKUJY-UHFFFAOYSA-N 1-benzyl-1-butyl-2-ethylpiperidin-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CCCC)CCCCC1CC OGGUGGJAFNKUJY-UHFFFAOYSA-N 0.000 description 1
- IGIDZTJXUZBDIV-UHFFFAOYSA-N 1-benzyl-1-butylpiperidin-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CCCC)CCCCC1 IGIDZTJXUZBDIV-UHFFFAOYSA-N 0.000 description 1
- YYGNHQBMHYRRRW-UHFFFAOYSA-N 1-benzyl-1-butylpyrrolidin-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CCCC)CCCC1 YYGNHQBMHYRRRW-UHFFFAOYSA-N 0.000 description 1
- JXYXZIMSZPRYGA-UHFFFAOYSA-N 1-benzyl-1-ethylpiperidin-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC)CCCCC1 JXYXZIMSZPRYGA-UHFFFAOYSA-N 0.000 description 1
- MLVJWHQRGPLNBP-UHFFFAOYSA-N 1-benzyl-1-hexylpiperidin-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CCCCCC)CCCCC1 MLVJWHQRGPLNBP-UHFFFAOYSA-N 0.000 description 1
- VGLXNNQUTZDJIR-UHFFFAOYSA-N 1-butyl-1-ethylpiperidin-1-ium Chemical compound CCCC[N+]1(CC)CCCCC1 VGLXNNQUTZDJIR-UHFFFAOYSA-N 0.000 description 1
- BNXZHVUCNYMNOS-UHFFFAOYSA-N 1-butylpyrrolidin-2-one Chemical compound CCCCN1CCCC1=O BNXZHVUCNYMNOS-UHFFFAOYSA-N 0.000 description 1
- JSHASCFKOSDFHY-UHFFFAOYSA-N 1-butylpyrrolidine Chemical compound CCCCN1CCCC1 JSHASCFKOSDFHY-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- VUQMOERHEHTWPE-UHFFFAOYSA-N 1-ethylpiperidin-2-one Chemical compound CCN1CCCCC1=O VUQMOERHEHTWPE-UHFFFAOYSA-N 0.000 description 1
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- YBJCDTIWNDBNTM-UHFFFAOYSA-N 1-methylsulfonylethane Chemical compound CCS(C)(=O)=O YBJCDTIWNDBNTM-UHFFFAOYSA-N 0.000 description 1
- XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 description 1
- YTEUDCIEJDRJTM-UHFFFAOYSA-N 2-(chloromethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCl YTEUDCIEJDRJTM-UHFFFAOYSA-N 0.000 description 1
- CQZWNRPXUQNVJN-UHFFFAOYSA-N 2-(cyanomethyl)benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1CC#N CQZWNRPXUQNVJN-UHFFFAOYSA-N 0.000 description 1
- JEVCFPPYJUBGIO-UHFFFAOYSA-N 2-(phenoxymethyl)benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1COC1=CC=CC=C1 JEVCFPPYJUBGIO-UHFFFAOYSA-N 0.000 description 1
- MIGNJKDTMBBNFI-UHFFFAOYSA-N 2-(phenoxymethyl)benzoyl cyanide Chemical class N#CC(=O)C1=CC=CC=C1COC1=CC=CC=C1 MIGNJKDTMBBNFI-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- WBUOVKBZJOIOAE-UHFFFAOYSA-N 3-chlorobenzonitrile Chemical compound ClC1=CC=CC(C#N)=C1 WBUOVKBZJOIOAE-UHFFFAOYSA-N 0.000 description 1
- XVFYQMYHHVGFCF-UHFFFAOYSA-N 4,4-dibutylmorpholin-4-ium Chemical compound CCCC[N+]1(CCCC)CCOCC1 XVFYQMYHHVGFCF-UHFFFAOYSA-N 0.000 description 1
- VAJZCFLYJRMBFN-UHFFFAOYSA-N 4,4-dimethylmorpholin-4-ium Chemical compound C[N+]1(C)CCOCC1 VAJZCFLYJRMBFN-UHFFFAOYSA-N 0.000 description 1
- PKXBQJFTZPYNKP-UHFFFAOYSA-N 4-benzyl-4-(2,3-dimethylbutyl)morpholin-4-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(C)C(C)C)CCOCC1 PKXBQJFTZPYNKP-UHFFFAOYSA-N 0.000 description 1
- AVDALCWMHDKNII-UHFFFAOYSA-N 4-benzyl-4-(2-ethylhexyl)morpholin-4-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(CC)CCCC)CCOCC1 AVDALCWMHDKNII-UHFFFAOYSA-N 0.000 description 1
- KOANBUOGQGULOE-UHFFFAOYSA-N 4-benzyl-4-butylmorpholin-4-ium Chemical compound C=1C=CC=CC=1C[N+]1(CCCC)CCOCC1 KOANBUOGQGULOE-UHFFFAOYSA-N 0.000 description 1
- WWCATYOKSUWRRS-UHFFFAOYSA-N 4-benzyl-4-ethylmorpholin-4-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC)CCOCC1 WWCATYOKSUWRRS-UHFFFAOYSA-N 0.000 description 1
- QEIDJQLLASNBGL-UHFFFAOYSA-N 4-benzyl-4-hexylmorpholin-4-ium Chemical compound C=1C=CC=CC=1C[N+]1(CCCCCC)CCOCC1 QEIDJQLLASNBGL-UHFFFAOYSA-N 0.000 description 1
- ACJFTLQVQOMXJC-UHFFFAOYSA-N 4-butyl-4-ethylmorpholin-4-ium Chemical compound CCCC[N+]1(CC)CCOCC1 ACJFTLQVQOMXJC-UHFFFAOYSA-N 0.000 description 1
- JKCGKHXBRTZNDH-UHFFFAOYSA-N 4-butyl-4-hexylmorpholin-4-ium Chemical compound CCCCCC[N+]1(CCCC)CCOCC1 JKCGKHXBRTZNDH-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241000199911 Peridinium Species 0.000 description 1
- 238000003482 Pinner synthesis reaction Methods 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- CHMJXSMKIAQCFF-UHFFFAOYSA-M azanium tetramethylazanium dibromide Chemical compound [Br-].[NH4+].C[N+](C)(C)C.[Br-] CHMJXSMKIAQCFF-UHFFFAOYSA-M 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- UDYGXWPMSJPFDG-UHFFFAOYSA-M benzyl(tributyl)azanium;bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 UDYGXWPMSJPFDG-UHFFFAOYSA-M 0.000 description 1
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- XSTSSSSQGIYEOF-UHFFFAOYSA-N benzyl-bis(2-methoxyethyl)-(2-methylbutyl)azanium Chemical compound CCC(C)C[N+](CCOC)(CCOC)CC1=CC=CC=C1 XSTSSSSQGIYEOF-UHFFFAOYSA-N 0.000 description 1
- GBDUVMXURMQGEO-UHFFFAOYSA-N benzyl-bis(2-methoxyethyl)-(3-methylbutyl)azanium Chemical compound COCC[N+](CCOC)(CCC(C)C)CC1=CC=CC=C1 GBDUVMXURMQGEO-UHFFFAOYSA-N 0.000 description 1
- DVWYXYUHYLMTJL-UHFFFAOYSA-N benzyl-cyclohexyl-diethylazanium Chemical compound C1CCCCC1[N+](CC)(CC)CC1=CC=CC=C1 DVWYXYUHYLMTJL-UHFFFAOYSA-N 0.000 description 1
- JARXMPNWSRDOGR-UHFFFAOYSA-N benzyl-dibutyl-ethylazanium Chemical compound CCCC[N+](CC)(CCCC)CC1=CC=CC=C1 JARXMPNWSRDOGR-UHFFFAOYSA-N 0.000 description 1
- FBKHZBFOYYEEEZ-UHFFFAOYSA-N benzyl-ethyl-bis(2-methoxyethyl)azanium Chemical compound COCC[N+](CC)(CCOC)CC1=CC=CC=C1 FBKHZBFOYYEEEZ-UHFFFAOYSA-N 0.000 description 1
- GDWGZMITXYQTKA-UHFFFAOYSA-N benzyl-ethyl-dipropylazanium Chemical compound CCC[N+](CC)(CCC)CC1=CC=CC=C1 GDWGZMITXYQTKA-UHFFFAOYSA-N 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- VVYXCRIHHKARDD-UHFFFAOYSA-N bis(2-methoxyethyl)-dipentylazanium Chemical compound CCCCC[N+](CCOC)(CCOC)CCCCC VVYXCRIHHKARDD-UHFFFAOYSA-N 0.000 description 1
- YFTLBBULVJLHQA-UHFFFAOYSA-N bis(2-methoxyethyl)-dipropylazanium Chemical compound COCC[N+](CCC)(CCC)CCOC YFTLBBULVJLHQA-UHFFFAOYSA-N 0.000 description 1
- 229940038926 butyl chloride Drugs 0.000 description 1
- BQXCLINCBQCIPL-UHFFFAOYSA-N butyl-bis(2-methoxyethyl)-(3-methylbutyl)azanium Chemical compound CCCC[N+](CCOC)(CCOC)CCC(C)C BQXCLINCBQCIPL-UHFFFAOYSA-N 0.000 description 1
- OVRHJTRSJKWPDL-UHFFFAOYSA-N butyl-ethyl-bis(2-methoxyethyl)azanium Chemical compound CCCC[N+](CC)(CCOC)CCOC OVRHJTRSJKWPDL-UHFFFAOYSA-N 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- YNZCFTWNMQAQFR-UHFFFAOYSA-N cyanomercury Chemical compound [Hg]C#N YNZCFTWNMQAQFR-UHFFFAOYSA-N 0.000 description 1
- PGHGDPCQBXTMAN-UHFFFAOYSA-N dibenzyl-bis(2-methoxyethyl)azanium Chemical compound C=1C=CC=CC=1C[N+](CCOC)(CCOC)CC1=CC=CC=C1 PGHGDPCQBXTMAN-UHFFFAOYSA-N 0.000 description 1
- MPXRTHRNQMUDNH-UHFFFAOYSA-N dibenzyl-cyclohexyl-ethylazanium Chemical compound C=1C=CC=CC=1C[N+](C1CCCCC1)(CC)CC1=CC=CC=C1 MPXRTHRNQMUDNH-UHFFFAOYSA-N 0.000 description 1
- UQOKGXWPSRIBBU-UHFFFAOYSA-N dibutyl-ethyl-(2-phenylethyl)azanium Chemical compound CCCC[N+](CC)(CCCC)CCC1=CC=CC=C1 UQOKGXWPSRIBBU-UHFFFAOYSA-N 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 description 1
- TUDUDQJRUPFUMA-UHFFFAOYSA-M ethyl(trioctyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCC[P+](CC)(CCCCCCCC)CCCCCCCC TUDUDQJRUPFUMA-UHFFFAOYSA-M 0.000 description 1
- VUFOSBDICLTFMS-UHFFFAOYSA-M ethyl-hexadecyl-dimethylazanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)CC VUFOSBDICLTFMS-UHFFFAOYSA-M 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000004009 herbicide Substances 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
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229940075610 mercuric cyanide Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- FHVMATOIMUHQRC-UHFFFAOYSA-N n,n-dimethyl-2-phenylacetamide Chemical compound CN(C)C(=O)CC1=CC=CC=C1 FHVMATOIMUHQRC-UHFFFAOYSA-N 0.000 description 1
- IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 description 1
- JBCOYDRQCPJFHJ-UHFFFAOYSA-N n,n-dimethylcyclohexanecarboxamide Chemical compound CN(C)C(=O)C1CCCCC1 JBCOYDRQCPJFHJ-UHFFFAOYSA-N 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical group 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical class OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
- 125000005506 phthalide group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- LFAGQMCIGQNPJG-UHFFFAOYSA-N silver cyanide Chemical compound [Ag+].N#[C-] LFAGQMCIGQNPJG-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- KRRBFUJMQBDDPR-UHFFFAOYSA-N tetrabutylazanium;cyanide Chemical compound N#[C-].CCCC[N+](CCCC)(CCCC)CCCC KRRBFUJMQBDDPR-UHFFFAOYSA-N 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- PCZOZSATUTWXIC-UHFFFAOYSA-N tetraethylazanium;cyanide Chemical compound N#[C-].CC[N+](CC)(CC)CC PCZOZSATUTWXIC-UHFFFAOYSA-N 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 description 1
- BJAARRARQJZURR-UHFFFAOYSA-N trimethylazanium;hydroxide Chemical compound O.CN(C)C BJAARRARQJZURR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/40—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4311722A DE4311722C1 (de) | 1993-04-08 | 1993-04-08 | Verfahren zur Herstellung von Halogenmethyl-benzoylcyaniden und neue Halogenmethyl-benzoylcyanide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU9400996D0 HU9400996D0 (en) | 1994-06-28 |
| HUT66608A HUT66608A (en) | 1994-12-28 |
| HU214952B true HU214952B (hu) | 1998-08-28 |
Family
ID=6485150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9400996A HU214952B (hu) | 1993-04-08 | 1994-04-07 | Eljárás halogén-metil-benzoil-cianidok előállítására és új halogén-metil-benzoil-cianidok |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US5446199A (OSRAM) |
| EP (1) | EP0619300B1 (OSRAM) |
| JP (2) | JP3811507B2 (OSRAM) |
| KR (1) | KR100310591B1 (OSRAM) |
| CN (1) | CN1037175C (OSRAM) |
| AT (1) | ATE146773T1 (OSRAM) |
| CA (1) | CA2120081C (OSRAM) |
| DE (2) | DE4311722C1 (OSRAM) |
| DK (1) | DK0619300T3 (OSRAM) |
| HU (1) | HU214952B (OSRAM) |
| IL (1) | IL109077A (OSRAM) |
| PL (1) | PL177244B1 (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4412316A1 (de) * | 1994-04-11 | 1995-10-12 | Basf Ag | Verfahren zur Herstellung von o-Chlormethylbenzoesäurechloriden |
| US5780665A (en) * | 1994-11-24 | 1998-07-14 | Basf Aktiengesellschaft | Preparation of halomethylbenzoyl cyanides |
| RU2133736C1 (ru) * | 1997-05-06 | 1999-07-27 | Закрытое акционерное общество "Химмедсинтез" | Способ получения нитрилов алкоксифенилуксусных кислот (варианты) |
| DE102005027149A1 (de) * | 2005-06-11 | 2006-12-14 | Lanxess Deutschland Gmbh | Verfahren zur Herstellung von substituierten Benzoylcyaniden |
| WO2007072679A1 (ja) * | 2005-12-20 | 2007-06-28 | Sumitomo Chemical Company, Limited | ２，４－ジフルオロニトロベンゼンの製造方法 |
| BRPI1005352A2 (pt) | 2009-02-05 | 2016-02-10 | Basf Se | processos para a produção de derivados do ácido 2-halogenometilfenil acético, processo para a produção de uma alquiloxima, processo para a produção de uma oxima, uso de 3-isocromanona e processo para a produção de um de um fungicida estrobilurina |
| CN113880729B (zh) * | 2021-10-29 | 2024-04-26 | 邯郸市瑞田农药有限公司 | 催化剂催化合成苯甲酰氰制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1563737A (OSRAM) * | 1967-12-08 | 1969-04-18 | ||
| DE2614241C3 (de) * | 1976-04-02 | 1980-03-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Acylcyaniden |
| DE2717075A1 (de) * | 1977-04-18 | 1978-10-26 | Degussa | Verfahren zur herstellung von benzoylcyanid |
| DE2753656C2 (de) * | 1977-12-02 | 1982-11-25 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Benzoylcyanid |
| DE2835440A1 (de) * | 1978-08-12 | 1980-02-28 | Dynamit Nobel Ag | Verfahren zur herstellung von chlormethyl-benzoylchloriden |
| US4238413A (en) * | 1979-11-07 | 1980-12-09 | Hooker Chemicals & Plastics Corp. | (3-Trifluoromethyl)-benzoyl cyanide and process for its production |
| DE3226425A1 (de) * | 1981-11-11 | 1983-05-19 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von acylcyaniden |
| DE3340933A1 (de) * | 1983-11-11 | 1985-05-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von (alpha)-ketonitrilen |
| DE3341306A1 (de) * | 1983-11-15 | 1985-05-23 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von in 2-stellung aromatisch oder heterocyclisch substituierten acetonitrilen |
| USRE33989E (en) * | 1986-07-16 | 1992-07-07 | Basf Aktiengesellschaft | Oxime ethers and fungicides containing these compounds |
| GB8617648D0 (en) * | 1986-07-18 | 1986-08-28 | Ici Plc | Fungicides |
| FR2629080B1 (fr) * | 1988-03-25 | 1990-11-16 | Poudres & Explosifs Ste Nale | Procede de preparation d'isocyanates d'acyle |
| US4986845A (en) * | 1988-07-15 | 1991-01-22 | Nissan Chemical Industries Ltd. | Pyrazole derivatives and herbicides containing them |
| US5352827A (en) * | 1989-05-19 | 1994-10-04 | Atochem | Synthesis of acyl cyanides in a hydrous reaction medium |
| FR2647110B1 (fr) * | 1989-05-19 | 1991-07-26 | Atochem | Procede de synthese de cyanures d'acyle |
| DK0712835T3 (da) * | 1990-12-31 | 1997-09-15 | Basf Ag | Fremgangsmåde til fremstilling af alfa-ketocarboxylsyreestere |
-
1993
- 1993-04-08 DE DE4311722A patent/DE4311722C1/de not_active Expired - Lifetime
-
1994
- 1994-03-22 IL IL109077A patent/IL109077A/en not_active IP Right Cessation
- 1994-03-23 US US08/216,416 patent/US5446199A/en not_active Expired - Lifetime
- 1994-03-24 EP EP94104664A patent/EP0619300B1/de not_active Expired - Lifetime
- 1994-03-24 DK DK94104664.1T patent/DK0619300T3/da active
- 1994-03-24 DE DE59401372T patent/DE59401372D1/de not_active Expired - Lifetime
- 1994-03-24 AT AT94104664T patent/ATE146773T1/de not_active IP Right Cessation
- 1994-03-28 CA CA002120081A patent/CA2120081C/en not_active Expired - Fee Related
- 1994-04-07 KR KR1019940007236A patent/KR100310591B1/ko not_active Expired - Fee Related
- 1994-04-07 PL PL94302939A patent/PL177244B1/pl not_active IP Right Cessation
- 1994-04-07 HU HU9400996A patent/HU214952B/hu not_active IP Right Cessation
- 1994-04-08 JP JP07049894A patent/JP3811507B2/ja not_active Expired - Lifetime
- 1994-04-08 CN CN94104064A patent/CN1037175C/zh not_active Expired - Lifetime
-
1995
- 1995-03-17 US US08/406,056 patent/US5510528A/en not_active Expired - Lifetime
-
2006
- 2006-02-28 JP JP2006052375A patent/JP4096045B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1037175C (zh) | 1998-01-28 |
| DE59401372D1 (de) | 1997-02-06 |
| HUT66608A (en) | 1994-12-28 |
| PL177244B1 (pl) | 1999-10-29 |
| CA2120081C (en) | 2004-12-28 |
| US5446199A (en) | 1995-08-29 |
| JPH06321886A (ja) | 1994-11-22 |
| DE4311722C1 (de) | 1994-04-07 |
| DK0619300T3 (OSRAM) | 1997-02-24 |
| CN1097412A (zh) | 1995-01-18 |
| EP0619300A3 (de) | 1995-03-29 |
| IL109077A0 (en) | 1994-06-24 |
| CA2120081A1 (en) | 1994-10-09 |
| KR100310591B1 (ko) | 2002-07-27 |
| US5510528A (en) | 1996-04-23 |
| JP2006188531A (ja) | 2006-07-20 |
| JP4096045B2 (ja) | 2008-06-04 |
| JP3811507B2 (ja) | 2006-08-23 |
| EP0619300B1 (de) | 1996-12-27 |
| HU9400996D0 (en) | 1994-06-28 |
| IL109077A (en) | 1998-06-15 |
| ATE146773T1 (de) | 1997-01-15 |
| EP0619300A2 (de) | 1994-10-12 |
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