DE4311722C1 - Verfahren zur Herstellung von Halogenmethyl-benzoylcyaniden und neue Halogenmethyl-benzoylcyanide - Google Patents
Verfahren zur Herstellung von Halogenmethyl-benzoylcyaniden und neue Halogenmethyl-benzoylcyanideInfo
- Publication number
- DE4311722C1 DE4311722C1 DE4311722A DE4311722A DE4311722C1 DE 4311722 C1 DE4311722 C1 DE 4311722C1 DE 4311722 A DE4311722 A DE 4311722A DE 4311722 A DE4311722 A DE 4311722A DE 4311722 C1 DE4311722 C1 DE 4311722C1
- Authority
- DE
- Germany
- Prior art keywords
- benzyl
- alkyl
- butyl
- halomethyl
- cyanide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000543 intermediate Substances 0.000 title abstract description 3
- 239000003905 agrochemical Substances 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims abstract description 6
- -1 hydroxyimino Chemical group 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 18
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910052723 transition metal Inorganic materials 0.000 claims description 5
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000005997 bromomethyl group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000003444 phase transfer catalyst Substances 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 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
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- GPGKNEKFDGOXPO-UHFFFAOYSA-N 4-phenyl-1h-pyrazole Chemical compound C1=NNC=C1C1=CC=CC=C1 GPGKNEKFDGOXPO-UHFFFAOYSA-N 0.000 abstract description 3
- 230000000895 acaricidal effect Effects 0.000 abstract description 2
- 239000000642 acaricide Substances 0.000 abstract description 2
- 239000000417 fungicide Substances 0.000 abstract description 2
- 239000002917 insecticide Substances 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- NRNOFFFWOYJUCR-UHFFFAOYSA-N 2-hydroxyimino-2-phenylacetic acid Chemical compound ON=C(C(O)=O)C1=CC=CC=C1 NRNOFFFWOYJUCR-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical group Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 239000011814 protection agent Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 6
- GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical class N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 description 5
- MVJIUTPZBDDMPF-UHFFFAOYSA-N 2-(chloromethyl)benzoyl cyanide Chemical compound ClCC1=CC=CC=C1C(=O)C#N MVJIUTPZBDDMPF-UHFFFAOYSA-N 0.000 description 4
- 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
- 239000012071 phase Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- PTIVSZNNOUZBKM-UHFFFAOYSA-N 1-benzylazepane Chemical compound C=1C=CC=CC=1CN1CCCCCC1 PTIVSZNNOUZBKM-UHFFFAOYSA-N 0.000 description 2
- CWEGCQIIDCZZED-UHFFFAOYSA-N 1-benzylpyrrolidine Chemical compound C=1C=CC=CC=1CN1CCCC1 CWEGCQIIDCZZED-UHFFFAOYSA-N 0.000 description 2
- ONQBOTKLCMXPOF-UHFFFAOYSA-N 1-ethylpyrrolidine Chemical compound CCN1CCCC1 ONQBOTKLCMXPOF-UHFFFAOYSA-N 0.000 description 2
- TXZFBHYDQGYOIT-UHFFFAOYSA-N 2-(chloromethyl)benzoyl chloride Chemical compound ClCC1=CC=CC=C1C(Cl)=O TXZFBHYDQGYOIT-UHFFFAOYSA-N 0.000 description 2
- WYXWANVHOUGOBI-UHFFFAOYSA-N 2-methylbenzoyl cyanide Chemical compound CC1=CC=CC=C1C(=O)C#N WYXWANVHOUGOBI-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- RUOFIIKCANAEBW-UHFFFAOYSA-N N-Ethyl-hexahydro-1H-azepine Chemical compound CCN1CCCCCC1 RUOFIIKCANAEBW-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 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
- 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
- 230000015572 biosynthetic process Effects 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
- 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 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical class OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- LFAGQMCIGQNPJG-UHFFFAOYSA-N silver cyanide Chemical compound [Ag+].N#[C-] LFAGQMCIGQNPJG-UHFFFAOYSA-N 0.000 description 2
- 229940098221 silver cyanide Drugs 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- 125000004765 (C1-C4) haloalkyl 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
- LZUCHRDYCFMEFN-UHFFFAOYSA-N 1,1-dibenzylazepan-1-ium Chemical compound C1CCCCC[N+]1(CC=1C=CC=CC=1)CC1=CC=CC=C1 LZUCHRDYCFMEFN-UHFFFAOYSA-N 0.000 description 1
- SLZWRBLOBWCVND-UHFFFAOYSA-N 1,1-dibenzylpyrrolidin-1-ium Chemical compound C1CCC[N+]1(CC=1C=CC=CC=1)CC1=CC=CC=C1 SLZWRBLOBWCVND-UHFFFAOYSA-N 0.000 description 1
- QNSDJERNKNPEMV-UHFFFAOYSA-N 1,1-dibutylazepan-1-ium Chemical compound CCCC[N+]1(CCCC)CCCCCC1 QNSDJERNKNPEMV-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
- 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
- NACXZUGMOKSHHV-UHFFFAOYSA-N 1-benzyl-1-(2,3-dimethylbutyl)-3,3,5-trimethylazepan-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(C)C(C)C)CCC(C)CC(C)(C)C1 NACXZUGMOKSHHV-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
- AAOJNGBCCGGFFG-UHFFFAOYSA-N 1-benzyl-1-(2-butoxypropyl)azepan-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(C)OCCCC)CCCCCC1 AAOJNGBCCGGFFG-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
- PQCNOSIKFLBYLE-UHFFFAOYSA-N 1-benzyl-1-(2-methoxypropyl)azepan-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(C)OC)CCCCCC1 PQCNOSIKFLBYLE-UHFFFAOYSA-N 0.000 description 1
- QCXXHGLLBBELQG-UHFFFAOYSA-N 1-benzyl-1-(2-methoxypropyl)piperidin-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(C)OC)CCCCC1 QCXXHGLLBBELQG-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
- 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
- DEXFGSLUARSEOT-UHFFFAOYSA-N 1-benzyl-1-[2-(2-methoxyethoxy)propyl]azepan-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(C)OCCOC)CCCCCC1 DEXFGSLUARSEOT-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
- MMGHDKYYQBDCFQ-UHFFFAOYSA-N 1-benzyl-1-butylazepan-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CCCC)CCCCCC1 MMGHDKYYQBDCFQ-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
- PSTQRHNSIMSVDM-UHFFFAOYSA-N 1-benzyl-1-cyclohexylazepan-1-ium Chemical compound C1CCCCC[N+]1(C1CCCCC1)CC1=CC=CC=C1 PSTQRHNSIMSVDM-UHFFFAOYSA-N 0.000 description 1
- BJIDCNORYZVDSQ-UHFFFAOYSA-N 1-benzyl-1-ethylazepan-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC)CCCCCC1 BJIDCNORYZVDSQ-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
- RTQVZFGDTRTYRE-UHFFFAOYSA-N 1-benzyl-1-propan-2-ylazepan-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(C(C)C)CCCCCC1 RTQVZFGDTRTYRE-UHFFFAOYSA-N 0.000 description 1
- XNXOQTBODXPYMG-UHFFFAOYSA-N 1-benzyl-1-propylazepan-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CCC)CCCCCC1 XNXOQTBODXPYMG-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
- WJCQFCRRWVKBSG-UHFFFAOYSA-N 1-butyl-2-ethylpiperidine Chemical compound CCCCN1CCCCC1CC WJCQFCRRWVKBSG-UHFFFAOYSA-N 0.000 description 1
- AXWLKJWVMMAXBD-UHFFFAOYSA-N 1-butylpiperidine Chemical compound CCCCN1CCCCC1 AXWLKJWVMMAXBD-UHFFFAOYSA-N 0.000 description 1
- BNXZHVUCNYMNOS-UHFFFAOYSA-N 1-butylpyrrolidin-2-one Chemical compound CCCCN1CCCC1=O BNXZHVUCNYMNOS-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
- LBFTVBIHZPCKME-UHFFFAOYSA-N 1-prop-1-en-2-yloxybutane Chemical group CCCCOC(C)=C LBFTVBIHZPCKME-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
- 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
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-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
- 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
- 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
- LMRKVKPRHROQRR-UHFFFAOYSA-N 4-butylmorpholine Chemical compound CCCCN1CCOCC1 LMRKVKPRHROQRR-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 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
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-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
- 241001676573 Minium Species 0.000 description 1
- PSFKQGZFNGHRHB-UHFFFAOYSA-N N-benzyl-N-ethyl-2,2-dimethoxyethanamine Chemical compound COC(OC)CN(CC)CC1=CC=CC=C1 PSFKQGZFNGHRHB-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
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- ICAIHGOJRDCMHE-UHFFFAOYSA-O ammonium cyanide Chemical class [NH4+].N#[C-] ICAIHGOJRDCMHE-UHFFFAOYSA-O 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 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
- FKPSBYZGRQJIMO-UHFFFAOYSA-M benzyl(triethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC1=CC=CC=C1 FKPSBYZGRQJIMO-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
- VXUWCRIOEOFANZ-UHFFFAOYSA-N benzyl-butyl-bis(2-methoxyethyl)azanium Chemical compound CCCC[N+](CCOC)(CCOC)CC1=CC=CC=C1 VXUWCRIOEOFANZ-UHFFFAOYSA-N 0.000 description 1
- SYLAQKBSMIRLCY-UHFFFAOYSA-N benzyl-butyl-cyclohexyl-ethylazanium Chemical compound C1CCCCC1[N+](CC)(CCCC)CC1=CC=CC=C1 SYLAQKBSMIRLCY-UHFFFAOYSA-N 0.000 description 1
- CUANMPXGWXCHHL-UHFFFAOYSA-N benzyl-butyl-diethylazanium;hexane Chemical compound CCCCCC.CCCC[N+](CC)(CC)CC1=CC=CC=C1 CUANMPXGWXCHHL-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
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 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
- MFIUDWFSVDFDDY-UHFFFAOYSA-M butyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC)C1=CC=CC=C1 MFIUDWFSVDFDDY-UHFFFAOYSA-M 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
- 125000005521 carbonamide group Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- YNZCFTWNMQAQFR-UHFFFAOYSA-N cyanomercury Chemical compound [Hg]C#N YNZCFTWNMQAQFR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 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
- YHMOPANBSNONIG-UHFFFAOYSA-N dibutyl-bis(2-methoxyethyl)azanium Chemical compound CCCC[N+](CCCC)(CCOC)CCOC YHMOPANBSNONIG-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
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 230000007717 exclusion Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 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
- 150000002500 ions Chemical class 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
- FQGYCXFLEQVDJQ-UHFFFAOYSA-N mercury dicyanide Chemical compound N#C[Hg]C#N FQGYCXFLEQVDJQ-UHFFFAOYSA-N 0.000 description 1
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 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
- MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 description 1
- ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-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
- 239000003960 organic solvent 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
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- QBVXKDJEZKEASM-UHFFFAOYSA-M tetraoctylammonium bromide Chemical compound [Br-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC QBVXKDJEZKEASM-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-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
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)
Priority Applications (15)
| 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 |
| IL109077A IL109077A (en) | 1993-04-08 | 1994-03-22 | Preparation of halomethylbenzoyl cyanides and certain such novel compounds |
| US08/216,416 US5446199A (en) | 1993-04-08 | 1994-03-23 | Preparation of halomethylbenzoyl cyanides and novel halomethylbenzoyl cyanides |
| DK94104664.1T DK0619300T3 (OSRAM) | 1993-04-08 | 1994-03-24 | |
| DE59401372T DE59401372D1 (de) | 1993-04-08 | 1994-03-24 | Verfahren zur Herstellung von Halogenmethylbenzoylcyaniden und neue Halogenmethyl-benzoylcyanide |
| AT94104664T ATE146773T1 (de) | 1993-04-08 | 1994-03-24 | Verfahren zur herstellung von halogenmethylbenzoylcyaniden und neue halogenmethyl-benzoylcyanide |
| EP94104664A EP0619300B1 (de) | 1993-04-08 | 1994-03-24 | Verfahren zur Herstellung von Halogenmethylbenzoylcyaniden und neue Halogenmethyl-benzoylcyanide |
| CA002120081A CA2120081C (en) | 1993-04-08 | 1994-03-28 | Preparation of halomethylbenzoyl cyanides and novel halomethylbenzoyl cyanides |
| HU9400996A HU214952B (hu) | 1993-04-08 | 1994-04-07 | Eljárás halogén-metil-benzoil-cianidok előállítására és új halogén-metil-benzoil-cianidok |
| KR1019940007236A KR100310591B1 (ko) | 1993-04-08 | 1994-04-07 | 할로메틸벤조일시아나이드의제조방법및신규할로메틸벤조일시아나이드 |
| PL94302939A PL177244B1 (pl) | 1993-04-08 | 1994-04-07 | Sposób wytwarzania cyjanków halogenometylo-benzoilu i nowe cyjanki halogenometylo-benzoilu |
| JP07049894A JP3811507B2 (ja) | 1993-04-08 | 1994-04-08 | 新規のシアン化ハロメチルベンゾイルおよびその製造方法 |
| CN94104064A CN1037175C (zh) | 1993-04-08 | 1994-04-08 | 新的卤代甲基苯甲酰氰类化合物及其制备方法 |
| US08/406,056 US5510528A (en) | 1993-04-08 | 1995-03-17 | Preparation of halomethylbenzoly cyanides and novel halomethylbenzoyl cyanides |
| JP2006052375A JP4096045B2 (ja) | 1993-04-08 | 2006-02-28 | 新規のシアン化ハロメチルベンゾイル |
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 (1)
| Publication Number | Publication Date |
|---|---|
| DE4311722C1 true DE4311722C1 (de) | 1994-04-07 |
Family
ID=6485150
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4311722A Expired - Lifetime DE4311722C1 (de) | 1993-04-08 | 1993-04-08 | Verfahren zur Herstellung von Halogenmethyl-benzoylcyaniden und neue Halogenmethyl-benzoylcyanide |
| DE59401372T Expired - Lifetime DE59401372D1 (de) | 1993-04-08 | 1994-03-24 | Verfahren zur Herstellung von Halogenmethylbenzoylcyaniden und neue Halogenmethyl-benzoylcyanide |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59401372T Expired - Lifetime DE59401372D1 (de) | 1993-04-08 | 1994-03-24 | Verfahren zur Herstellung von Halogenmethylbenzoylcyaniden und neue Halogenmethyl-benzoylcyanide |
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) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0676389A3 (de) * | 1994-04-11 | 1996-03-06 | Basf Ag | Verfahren zur Herstellung von 0-Chloromethylbenzoesäurechloriden. |
| WO1996016023A1 (de) * | 1994-11-24 | 1996-05-30 | Basf Aktiengesellschaft | Verfahren zur herstellung von halogenmethyl-benzoylcyaniden |
| RU2133736C1 (ru) * | 1997-05-06 | 1999-07-27 | Закрытое акционерное общество "Химмедсинтез" | Способ получения нитрилов алкоксифенилуксусных кислот (варианты) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0352543A1 (en) * | 1988-07-15 | 1990-01-31 | Nissan Chemical Industries Ltd. | Pyrazole derivatives and herbicides containing them |
Family Cites Families (15)
| 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 |
| 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 |
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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 DE DE59401372T patent/DE59401372D1/de not_active Expired - Lifetime
- 1994-03-24 AT AT94104664T patent/ATE146773T1/de not_active IP Right Cessation
- 1994-03-24 EP EP94104664A patent/EP0619300B1/de not_active Expired - Lifetime
- 1994-03-24 DK DK94104664.1T patent/DK0619300T3/da active
- 1994-03-28 CA CA002120081A patent/CA2120081C/en 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
- 1994-04-07 KR KR1019940007236A patent/KR100310591B1/ko not_active Expired - Fee Related
- 1994-04-08 CN CN94104064A patent/CN1037175C/zh not_active Expired - Lifetime
- 1994-04-08 JP JP07049894A patent/JP3811507B2/ja 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
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0352543A1 (en) * | 1988-07-15 | 1990-01-31 | Nissan Chemical Industries Ltd. | Pyrazole derivatives and herbicides containing them |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0676389A3 (de) * | 1994-04-11 | 1996-03-06 | Basf Ag | Verfahren zur Herstellung von 0-Chloromethylbenzoesäurechloriden. |
| WO1996016023A1 (de) * | 1994-11-24 | 1996-05-30 | Basf Aktiengesellschaft | Verfahren zur herstellung von halogenmethyl-benzoylcyaniden |
| RU2152926C1 (ru) * | 1994-11-24 | 2000-07-20 | Басф Акциенгезельшафт | Способ получения галогенметилбензоилцианидов |
| RU2133736C1 (ru) * | 1997-05-06 | 1999-07-27 | Закрытое акционерное общество "Химмедсинтез" | Способ получения нитрилов алкоксифенилуксусных кислот (варианты) |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0619300A3 (de) | 1995-03-29 |
| CN1037175C (zh) | 1998-01-28 |
| CA2120081A1 (en) | 1994-10-09 |
| IL109077A0 (en) | 1994-06-24 |
| DK0619300T3 (OSRAM) | 1997-02-24 |
| JP3811507B2 (ja) | 2006-08-23 |
| JP2006188531A (ja) | 2006-07-20 |
| HU9400996D0 (en) | 1994-06-28 |
| IL109077A (en) | 1998-06-15 |
| JP4096045B2 (ja) | 2008-06-04 |
| CN1097412A (zh) | 1995-01-18 |
| DE59401372D1 (de) | 1997-02-06 |
| HUT66608A (en) | 1994-12-28 |
| EP0619300B1 (de) | 1996-12-27 |
| JPH06321886A (ja) | 1994-11-22 |
| EP0619300A2 (de) | 1994-10-12 |
| ATE146773T1 (de) | 1997-01-15 |
| CA2120081C (en) | 2004-12-28 |
| KR100310591B1 (ko) | 2002-07-27 |
| PL177244B1 (pl) | 1999-10-29 |
| US5446199A (en) | 1995-08-29 |
| US5510528A (en) | 1996-04-23 |
| HU214952B (hu) | 1998-08-28 |
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| 8100 | Publication of patent without earlier publication of application | ||
| D1 | Grant (no unexamined application published) patent law 81 | ||
| 8364 | No opposition during term of opposition | ||
| 8330 | Complete renunciation |