CS211390B2 - Method of preparation of the + l s + p-alpha-kyano-3-phenoxybenzyl-+ l s + p -2- + l 4-chlophenyl + p isovalerate - Google Patents

Method of preparation of the + l s + p-alpha-kyano-3-phenoxybenzyl-+ l s + p -2- + l 4-chlophenyl + p isovalerate Download PDF

Info

Publication number: CS211390B2
Authority: CS; Czechoslovakia
Prior art keywords: fenvalerate; crystals; solvent; solution; isomer
Prior art date: 1977-10-07

Application number

CS786562A

Other languages

Czech (cs)

English (en)

Inventor

Kohichi Aketa

Yukio Suzuki

Nobuo Ohno

Isamu Nakayama

Takashi Kato

Original Assignee

Sumitomo Chemical Co

Priority date (The priority date 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 date listed.)

1977-10-07

Filing date

1978-10-09

Publication date

1982-02-26

1978-10-09 Application filed by Sumitomo Chemical Co filed Critical Sumitomo Chemical Co

1979-09-06 Priority to CS796039A priority Critical patent/CS211391B2/cs

1982-02-26 Publication of CS211390B2 publication Critical patent/CS211390B2/cs

Links

GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 title claims abstract description 10
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 title claims abstract description 10
238000000034 method Methods 0.000 title claims description 30
238000002360 preparation method Methods 0.000 title claims description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 165
239000003054 catalyst Substances 0.000 claims abstract description 40
-1 triethylamine Chemical class 0.000 claims abstract description 22
150000001412 amines Chemical class 0.000 claims abstract description 4
NYPJDWWKZLNGGM-DNQXCXABSA-N [(s)-cyano-(3-phenoxyphenyl)methyl] (2r)-2-(4-chlorophenyl)-3-methylbutanoate Chemical compound C=1C([C@@H](C#N)OC(=O)[C@H](C(C)C)C=2C=CC(Cl)=CC=2)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-DNQXCXABSA-N 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 67
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 45
239000002904 solvent Substances 0.000 claims description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 21
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 14
239000002585 base Substances 0.000 claims description 13
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 10
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 10
229910021529 ammonia Inorganic materials 0.000 claims description 10
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
229930195733 hydrocarbon Natural products 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 8
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 7
239000004215 Carbon black (E152) Substances 0.000 claims description 6
150000001342 alkaline earth metals Chemical class 0.000 claims description 6
239000012046 mixed solvent Substances 0.000 claims description 6
150000001338 aliphatic hydrocarbons Chemical group 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 5
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 5
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
239000003456 ion exchange resin Substances 0.000 claims description 4
229920003303 ion-exchange polymer Polymers 0.000 claims description 4
239000008096 xylene Substances 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 3
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
150000008046 alkali metal hydrides Chemical class 0.000 claims description 2
150000002430 hydrocarbons Chemical class 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims 1
150000001408 amides Chemical class 0.000 claims 1
239000013078 crystal Substances 0.000 abstract description 115
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 45
238000006317 isomerization reaction Methods 0.000 abstract description 13
230000000749 insecticidal effect Effects 0.000 abstract description 11
238000002425 crystallisation Methods 0.000 abstract description 9
230000008025 crystallization Effects 0.000 abstract description 9
239000002917 insecticide Substances 0.000 abstract description 2
NYPJDWWKZLNGGM-CGAIIQECSA-N [cyano-(3-phenoxyphenyl)methyl] (2s)-2-(4-chlorophenyl)-3-methylbutanoate Chemical compound O=C([C@@H](C(C)C)C=1C=CC(Cl)=CC=1)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-CGAIIQECSA-N 0.000 abstract 1
230000000694 effects Effects 0.000 abstract 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 267
239000000243 solution Substances 0.000 description 64
150000002148 esters Chemical class 0.000 description 52
125000003158 alcohol group Chemical group 0.000 description 37
238000001914 filtration Methods 0.000 description 30
238000004458 analytical method Methods 0.000 description 29
239000000047 product Substances 0.000 description 15
239000002253 acid Substances 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
230000003287 optical effect Effects 0.000 description 6
150000001721 carbon Chemical group 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
NYPJDWWKZLNGGM-RPWUZVMVSA-N esfenvalerate Chemical compound C=1C([C@@H](C#N)OC(=O)[C@@H](C(C)C)C=2C=CC(Cl)=CC=2)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-RPWUZVMVSA-N 0.000 description 5
239000012452 mother liquor Substances 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
235000011114 ammonium hydroxide Nutrition 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 3
FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 3
VTJMSIIXXKNIDJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutyric acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(Cl)C=C1 VTJMSIIXXKNIDJ-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
229940024113 allethrin Drugs 0.000 description 3
239000002728 pyrethroid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
FPUCYPXKIFVDSD-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetic acid Chemical compound OC(=O)C(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 FPUCYPXKIFVDSD-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
239000003021 water soluble solvent Substances 0.000 description 2
VTJMSIIXXKNIDJ-JTQLQIEISA-N (2s)-2-(4-chlorophenyl)-3-methylbutanoic acid Chemical compound CC(C)[C@H](C(O)=O)C1=CC=C(Cl)C=C1 VTJMSIIXXKNIDJ-JTQLQIEISA-N 0.000 description 1
NNICRUQPODTGRU-UHFFFAOYSA-N (R)-2-Hydroxy-2-phenylacetonitrile Natural products N#CC(O)C1=CC=CC=C1 NNICRUQPODTGRU-UHFFFAOYSA-N 0.000 description 1
XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
HDLQGISFYDYWFJ-UHFFFAOYSA-N 3-methyl-2-phenylbutanoic acid Chemical class CC(C)C(C(O)=O)C1=CC=CC=C1 HDLQGISFYDYWFJ-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
241000238631 Hexapoda Species 0.000 description 1
VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical group [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
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 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000010304 firing Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
PKMBLJNMKINMSK-UHFFFAOYSA-N magnesium;azanide Chemical compound [NH2-].[NH2-].[Mg+2] PKMBLJNMKINMSK-UHFFFAOYSA-N 0.000 description 1
231100001225 mammalian toxicity Toxicity 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003799 water insoluble solvent Substances 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CS786562A 1977-10-07 1978-10-09 Method of preparation of the + l s + p-alpha-kyano-3-phenoxybenzyl-+ l s + p -2- + l 4-chlophenyl + p isovalerate CS211390B2 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CS796039A CS211391B2 (cs)	1978-10-09	1979-09-06	Způsob přípravy (S)-a-kyano-3-řenoxybenzyl-(S)-2-( 4-chlorfenyl )- isovalerátu

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP12124277A JPS5455546A (en)	1977-10-07	1977-10-07	Preparation of optically active alpha-cyano-3-phenoxy-benzyl 2-(4-chlorophenyl)-isovalerate

Publications (1)

Publication Number	Publication Date
CS211390B2 true CS211390B2 (en)	1982-02-26

Family

ID=14806412

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS786562A CS211390B2 (en)	1977-10-07	1978-10-09	Method of preparation of the + l s + p-alpha-kyano-3-phenoxybenzyl-+ l s + p -2- + l 4-chlophenyl + p isovalerate

Country Status (4)

Country	Link
JP (1)	JPS5455546A (tr)
CS (1)	CS211390B2 (tr)
SU (1)	SU1060104A3 (tr)
TR (1)	TR20209A (tr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57169453A (en) *	1981-04-13	1982-10-19	Sumitomo Chem Co Ltd	Preparation of optically active carboxylic ester

1977
- 1977-10-07 JP JP12124277A patent/JPS5455546A/ja active Pending
1978
- 1978-10-09 CS CS786562A patent/CS211390B2/cs unknown
- 1978-10-09 TR TR20209A patent/TR20209A/tr unknown
1979
- 1979-10-26 SU SU792831253A patent/SU1060104A3/ru active

Also Published As

Publication number	Publication date
TR20209A (tr)	1980-10-17
SU1060104A3 (ru)	1983-12-07
JPS5455546A (en)	1979-05-02

Publication	Publication Date	Title
US4133826A (en)	1979-01-09	Novel inversion process
US4312816A (en)	1982-01-26	Process for preparing optically active α-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)isovalerate
EP0040991B1 (en)	1984-07-18	Preparation of insecticidal mixture of stereoisomers of alpha-cyano-3-phenoxybenzyl isovalerates
EP0109113B1 (en)	1986-04-23	Process for preparing cyclopropane carboxylic acid ester derivatives
EP0134303B1 (en)	1988-01-27	Menthyl 2,2-dimethylcyclopropanecarboxylate and resolution of the same
NL8006398A (nl)	1981-07-01	Cyclopropaan-carbonzure ester-derivaten.
JP3032447B2 (ja)	2000-04-17	光学活性な２−プロピルオクタン酸の製造方法
EP0093511B1 (en)	1986-09-24	Method for producing and optically active 2,2-dimethylcyclopropanecarboxylic acid
ES8203074A1 (es)	1982-02-16	Un procedimiento para preparar derivados de esteres del aci-do ciclopropanocarboxilico
US4005146A (en)	1977-01-25	Resolution of dl-allethrolone
CA1132605A (en)	1982-09-28	Preparation of cyano substituted benzyl ester insecticides
CS197286B2 (en)	1980-04-30	Process for preparing alpha-cyanobenzylesteres of alkanoic and cycloalkanoic acids
US4436667A (en)	1984-03-13	Process for preparing cyclopropane carboxylic acid ester derivatives
JPS6054952B2 (ja)	1985-12-03	シアノ置換エステルの製造方法
SU1060104A3 (ru)	1983-12-07	Способ получени оптически активного / @ /- @ -циано-3-феноксибензил-/ @ /-2-/4-хлорфенил/ изовалерата
US4238423A (en)	1980-12-09	Process for preparing cyclo-1,3,2-oxazaphosphoryl derivatives
EP0034428A2 (en)	1981-08-26	A method of resolving optical isomers of 2,2-dimethyl-3-(2,2-dichlorovinyl) cyclopropanecarboxylic acid and a novel salt used in this method
JPS6337783B2 (tr)	1988-07-27
US4709082A (en)	1987-11-24	2-phenylpropionic acid esters, method for optical resolution thereof and optically active substance thereof
EP0050521B1 (en)	1984-11-21	Preparation of insecticidal optically active isovalerate esters
HU205594B (en)	1992-05-28	Process for producing optical isomeres of cyclopropane-carboxylic acids5
US5023365A (en)	1991-06-11	Process for preparing an intermediate
US5306844A (en)	1994-04-26	Tartaric acid amide derivative and method of producing the same
EP1671939A1 (de)	2006-06-21	Verfahren zur Herstellung von enantiomerenangereicherten 2-Fluorcarbonsäureestern
US4234506A (en)	1980-11-18	Process for preparing cyanohydrin esters