JP3811507B2 - 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 - Google Patents
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 Download PDFInfo
- Publication number
- JP3811507B2 JP3811507B2 JP07049894A JP7049894A JP3811507B2 JP 3811507 B2 JP3811507 B2 JP 3811507B2 JP 07049894 A JP07049894 A JP 07049894A JP 7049894 A JP7049894 A JP 7049894A JP 3811507 B2 JP3811507 B2 JP 3811507B2
- Authority
- JP
- Japan
- Prior art keywords
- cyanide
- benzyl
- halomethylbenzoyl
- alkyl
- chloride
- 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
- 238000000034 method Methods 0.000 title claims description 17
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 title claims description 11
- -1 alkali metal cyanide Chemical class 0.000 claims abstract description 36
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims abstract description 6
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 6
- 125000005997 bromomethyl group Chemical group 0.000 claims abstract description 5
- 239000003085 diluting agent Substances 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 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 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000003444 phase transfer catalyst Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 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 claims 1
- 150000002825 nitriles Chemical class 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 2
- 239000011814 protection agent 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
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 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
- 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
- 239000000243 solution Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical compound N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 description 6
- MVJIUTPZBDDMPF-UHFFFAOYSA-N 2-(chloromethyl)benzoyl cyanide Chemical compound ClCC1=CC=CC=C1C(=O)C#N MVJIUTPZBDDMPF-UHFFFAOYSA-N 0.000 description 5
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 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
- 229910052740 iodine Inorganic materials 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 4
- TXZFBHYDQGYOIT-UHFFFAOYSA-N 2-(chloromethyl)benzoyl chloride Chemical compound ClCC1=CC=CC=C1C(Cl)=O TXZFBHYDQGYOIT-UHFFFAOYSA-N 0.000 description 3
- 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
- 239000002253 acid Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011541 reaction mixture Substances 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
- NZVZVGPYTICZBZ-UHFFFAOYSA-N 1-benzylpiperidine Chemical compound C=1C=CC=CC=1CN1CCCCC1 NZVZVGPYTICZBZ-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
- GPGKNEKFDGOXPO-UHFFFAOYSA-N 4-phenyl-1h-pyrazole Chemical compound 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
- 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
- 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- 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
- 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
- XTBPKISXEWSOFF-UHFFFAOYSA-N butyl-cyclohexyl-diethylazanium Chemical compound CCCC[N+](CC)(CC)C1CCCCC1 XTBPKISXEWSOFF-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 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
- 239000004009 herbicide Substances 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
- 239000002917 insecticide Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- JBCOYDRQCPJFHJ-UHFFFAOYSA-N n,n-dimethylcyclohexanecarboxamide Chemical compound CN(C)C(=O)C1CCCCC1 JBCOYDRQCPJFHJ-UHFFFAOYSA-N 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229940098221 silver cyanide Drugs 0.000 description 2
- 239000000126 substance Substances 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
- 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
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 1
- 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
- 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
- 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
- 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
- AJOAQGOXFSILHG-UHFFFAOYSA-N 1-benzyl-1-(2,3-dimethylbutyl)azepan-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(C)C(C)C)CCCCCC1 AJOAQGOXFSILHG-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
- 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
- RXXUEFMPKSHYHE-UHFFFAOYSA-N 1-benzyl-1-(2-ethylhexyl)-3,3,5-trimethylazepan-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(CC)CCCC)CCC(C)CC(C)(C)C1 RXXUEFMPKSHYHE-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
- AUCBEFVPGNCQFU-UHFFFAOYSA-N 1-benzyl-1-(2-methylpentyl)azepan-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(C)CCC)CCCCCC1 AUCBEFVPGNCQFU-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
- WBAQBNMSGVDMOT-UHFFFAOYSA-N 1-benzyl-1-(3,5,5-trimethylhexyl)azepan-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CCC(C)CC(C)(C)C)CCCCCC1 WBAQBNMSGVDMOT-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
- BFRGLQSNNFKTKL-UHFFFAOYSA-N 1-benzyl-1-(4,4-dimethylpentyl)piperidin-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CCCC(C)(C)C)CCCCC1 BFRGLQSNNFKTKL-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
- 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
- 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
- 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
- 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
- XDKMMXJCRLQPIP-UHFFFAOYSA-N 1-benzyl-3,3,5-trimethyl-1-(2-methylpentyl)azepan-1-ium Chemical compound C=1C=CC=CC=1C[N+]1(CC(C)CCC)CCC(C)CC(C)(C)C1 XDKMMXJCRLQPIP-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
- WYANFTXHKVXPFJ-UHFFFAOYSA-N 1-cyclopentylpiperidine Chemical compound C1CCCC1N1CCCCC1 WYANFTXHKVXPFJ-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 compound ClC(=O)C1=CC=CC=C1COC1=CC=CC=C1 JEVCFPPYJUBGIO-UHFFFAOYSA-N 0.000 description 1
- MIGNJKDTMBBNFI-UHFFFAOYSA-N 2-(phenoxymethyl)benzoyl cyanide Chemical compound N#CC(=O)C1=CC=CC=C1COC1=CC=CC=C1 MIGNJKDTMBBNFI-UHFFFAOYSA-N 0.000 description 1
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical compound ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- GAZWMILIFZQWKD-UHFFFAOYSA-N C(C1=CC=CC=C1)[N+](CCOC)(CCOC)CCC(C)C.C(CCC)[N+](CCOC)(CCOC)CCC(C)C Chemical compound C(C1=CC=CC=C1)[N+](CCOC)(CCOC)CCC(C)C.C(CCC)[N+](CCOC)(CCOC)CCC(C)C GAZWMILIFZQWKD-UHFFFAOYSA-N 0.000 description 1
- KLNRMUPEMKDWIU-UHFFFAOYSA-N C(C1=CC=CC=C1)[N+]1(CCCCC1)CC(OCCOC)C.C(C1=CC=CC=C1)[N+]1(CCCCC1)CC(OCCCC)C Chemical compound C(C1=CC=CC=C1)[N+]1(CCCCC1)CC(OCCOC)C.C(C1=CC=CC=C1)[N+]1(CCCCC1)CC(OCCCC)C KLNRMUPEMKDWIU-UHFFFAOYSA-N 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
- XDFCYIZUMJOLCU-UHFFFAOYSA-N N-(2-benzyl-3-phenylpropyl)cyclohexanamine Chemical compound C=1C=CC=CC=1CC(CC=1C=CC=CC=1)CNC1CCCCC1 XDFCYIZUMJOLCU-UHFFFAOYSA-N 0.000 description 1
- XVWOXLZMZPYQDK-UHFFFAOYSA-N N-(2-cyclohexylethyl)-5-phenylpentan-1-amine Chemical compound C=1C=CC=CC=1CCCCCNCCC1CCCCC1 XVWOXLZMZPYQDK-UHFFFAOYSA-N 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
- 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
- VOFGKOQTSCTGIZ-UHFFFAOYSA-N [Hg]C#N.C(C1=CC=CC=C1)(=O)Cl Chemical compound [Hg]C#N.C(C1=CC=CC=C1)(=O)Cl VOFGKOQTSCTGIZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- FNEPSTUXZLEUCK-UHFFFAOYSA-N benzo-15-crown-5 Chemical compound O1CCOCCOCCOCCOC2=CC=CC=C21 FNEPSTUXZLEUCK-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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 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
- 150000003857 carboxamides 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
- 239000000039 congener Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000003983 crown ethers Chemical group 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
- YHMOPANBSNONIG-UHFFFAOYSA-N dibutyl-bis(2-methoxyethyl)azanium Chemical compound CCCC[N+](CCCC)(CCOC)CCOC YHMOPANBSNONIG-UHFFFAOYSA-N 0.000 description 1
- BBGKDYHZQOSNMU-UHFFFAOYSA-N dicyclohexano-18-crown-6 Chemical compound O1CCOCCOC2CCCCC2OCCOCCOC2CCCCC21 BBGKDYHZQOSNMU-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
- 239000003480 eluent Substances 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen 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
- 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
- 150000004679 hydroxides Chemical group 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)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
- 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
- SRESKMPUIWAGML-UHFFFAOYSA-N n,n-dimethyldecan-1-amine;hydrobromide Chemical compound Br.CCCCCCCCCCN(C)C SRESKMPUIWAGML-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
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 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
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical class OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 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
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical group 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
- 125000005207 tetraalkylammonium group Chemical group 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
- 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
- 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
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 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
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 1
- 230000007704 transition Effects 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)
Applications Claiming Priority (2)
| 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 |
| DE4311722.8 | 1993-04-08 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006052375A Division 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06321886A JPH06321886A (ja) | 1994-11-22 |
| JP3811507B2 true JP3811507B2 (ja) | 2006-08-23 |
Family
ID=6485150
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP07049894A Expired - Lifetime 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 |
| JP2006052375A Expired - Fee Related 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 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006052375A Expired - Fee Related 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 |
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 |
| AU694590B2 (en) * | 1994-11-24 | 1998-07-23 | Basf Aktiengesellschaft | Process for preparing halogenated methyl benzoyl 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 |
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| 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 |
| DE59108848D1 (de) * | 1990-12-31 | 1997-10-09 | Basf Ag | Verfahren zur Herstellung von 2-Phenoxymethylbenzoesäuren |
-
1993
- 1993-04-08 DE DE4311722A patent/DE4311722C1/de not_active Expired - Lifetime
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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
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1995
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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 |
| JP2006188531A (ja) | 2006-07-20 |
| HU9400996D0 (en) | 1994-06-28 |
| IL109077A (en) | 1998-06-15 |
| DE4311722C1 (de) | 1994-04-07 |
| 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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