GB1572183A - Cyclopropane carboxylic acid ester synthesis and intermediates therefor - Google Patents
Cyclopropane carboxylic acid ester synthesis and intermediates therefor Download PDFInfo
- Publication number
- GB1572183A GB1572183A GB36688/75A GB3668875A GB1572183A GB 1572183 A GB1572183 A GB 1572183A GB 36688/75 A GB36688/75 A GB 36688/75A GB 3668875 A GB3668875 A GB 3668875A GB 1572183 A GB1572183 A GB 1572183A
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- GB
- United Kingdom
- Prior art keywords
- acid
- formula
- compound
- trans
- group
- 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
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- 239000000543 intermediate Substances 0.000 title abstract description 7
- 230000015572 biosynthetic process Effects 0.000 title description 14
- 238000003786 synthesis reaction Methods 0.000 title description 10
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 239000002253 acid Substances 0.000 claims abstract description 49
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 140
- 239000000243 solution Substances 0.000 claims description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 52
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 44
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 44
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 44
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
- 229910001868 water Inorganic materials 0.000 claims description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- -1 vinyl compound Chemical class 0.000 claims description 32
- 150000002148 esters Chemical class 0.000 claims description 30
- 239000000047 product Substances 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 22
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 22
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 19
- 239000003208 petroleum Substances 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 238000001816 cooling Methods 0.000 claims description 14
- 239000003153 chemical reaction reagent Substances 0.000 claims description 13
- 230000000749 insecticidal effect Effects 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 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 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 238000001953 recrystallisation Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 229950005499 carbon tetrachloride Drugs 0.000 claims description 5
- 150000007942 carboxylates Chemical class 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 5
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000005521 carbonamide group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 150000002825 nitriles Chemical group 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- DBIPVNZNXKVLTL-NTSWFWBYSA-N (1s,3s)-3-acetyl-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC(=O)[C@H]1[C@H](C(O)=O)C1(C)C DBIPVNZNXKVLTL-NTSWFWBYSA-N 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 239000012454 non-polar solvent Substances 0.000 claims description 3
- 230000020477 pH reduction Effects 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- 229910000761 Aluminium amalgam Inorganic materials 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 239000004411 aluminium Substances 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 238000004458 analytical method Methods 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000012267 brine Substances 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- VGLKHVQPWGFXEG-NCJHBDPTSA-K europium(3+);(1z)-2,2,3,3,4,4,4-heptafluoro-1-(4,7,7-trimethyl-3-oxo-2-bicyclo[2.2.1]heptanylidene)butan-1-olate Chemical compound [Eu+3].C1CC2(C)C(=O)\C(=C(/[O-])C(F)(F)C(F)(F)C(F)(F)F)C1C2(C)C.C1CC2(C)C(=O)\C(=C(/[O-])C(F)(F)C(F)(F)C(F)(F)F)C1C2(C)C.C1CC2(C)C(=O)\C(=C(/[O-])C(F)(F)C(F)(F)C(F)(F)F)C1C2(C)C VGLKHVQPWGFXEG-NCJHBDPTSA-K 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 230000026030 halogenation Effects 0.000 claims description 2
- 238000005658 halogenation reaction Methods 0.000 claims description 2
- 238000006317 isomerization reaction Methods 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
- 229910001023 sodium amalgam Inorganic materials 0.000 claims 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical class CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000003480 eluent Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000002440 hydroxy compounds Chemical class 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- JSYWFZSGEYORRR-UHFFFAOYSA-N ethyl 3-acetyl-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CCOC(=O)C1C(C(C)=O)C1(C)C JSYWFZSGEYORRR-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 2
- DBIPVNZNXKVLTL-UHFFFAOYSA-N 3-acetyl-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC(=O)C1C(C(O)=O)C1(C)C DBIPVNZNXKVLTL-UHFFFAOYSA-N 0.000 description 2
- KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- CKFBFQHBUCDOHL-UHFFFAOYSA-N phenoxy(phenyl)methanol Chemical compound C=1C=CC=CC=1C(O)OC1=CC=CC=C1 CKFBFQHBUCDOHL-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- SSTZGACKDAVIGZ-UHFFFAOYSA-N sulfanium;bromide Chemical compound [SH3+].[Br-] SSTZGACKDAVIGZ-UHFFFAOYSA-N 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- JXFPTJYKYKVENJ-UHFFFAOYSA-M (2-ethoxy-2-oxoethyl)-dimethylsulfanium;bromide Chemical compound [Br-].CCOC(=O)C[S+](C)C JXFPTJYKYKVENJ-UHFFFAOYSA-M 0.000 description 1
- AFEOKIGLYCQHAZ-UHFFFAOYSA-N (5-benzylfuran-3-yl)methanol Chemical compound OCC1=COC(CC=2C=CC=CC=2)=C1 AFEOKIGLYCQHAZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- DRSZTATWOSZRAK-UHFFFAOYSA-N 3,4-dibromobutan-2-one Chemical compound CC(=O)C(Br)CBr DRSZTATWOSZRAK-UHFFFAOYSA-N 0.000 description 1
- MVTLWPZRRVGVIN-UHFFFAOYSA-N 3-acetyl-2,2-dimethylcyclopropane-1-carboxamide Chemical compound CC(=O)C1C(C(N)=O)C1(C)C MVTLWPZRRVGVIN-UHFFFAOYSA-N 0.000 description 1
- PXACTUVBBMDKRW-UHFFFAOYSA-M 4-bromobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- BXEFQPCKQSTMKA-UHFFFAOYSA-N OC(=O)C=[N+]=[N-] Chemical class OC(=O)C=[N+]=[N-] BXEFQPCKQSTMKA-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- SBSKGQCBXXGODA-UHFFFAOYSA-N [phenoxy(phenyl)methyl] 3-(2,2-dichloroacetyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound ClC(Cl)C(=O)C1C(C)(C)C1C(=O)OC(C=1C=CC=CC=1)OC1=CC=CC=C1 SBSKGQCBXXGODA-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- JCISJVGBGSMDJD-UHFFFAOYSA-N benzyl 3-acetyl-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C(=O)C)C1C(=O)OCC1=CC=CC=C1 JCISJVGBGSMDJD-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- SSVFMICWXDVRQN-UHFFFAOYSA-N ethanol;sodium Chemical compound [Na].CCO SSVFMICWXDVRQN-UHFFFAOYSA-N 0.000 description 1
- USPVNSDVCUTNJN-UHFFFAOYSA-N ethenyl cyclopropanecarboxylate Chemical class C=COC(=O)C1CC1 USPVNSDVCUTNJN-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- IYIIQFWQWNLGMA-PHDIDXHHSA-N ethyl (1S,3S)-3-(2,2-dichloroacetyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound ClC(C(=O)[C@@H]1C([C@H]1C(=O)OCC)(C)C)Cl IYIIQFWQWNLGMA-PHDIDXHHSA-N 0.000 description 1
- JSYWFZSGEYORRR-JGVFFNPUSA-N ethyl (1s,3s)-3-acetyl-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CCOC(=O)[C@H]1[C@H](C(C)=O)C1(C)C JSYWFZSGEYORRR-JGVFFNPUSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- MFBOGIVSZKQAPD-UHFFFAOYSA-M sodium butyrate Chemical compound [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/67—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Furan Compounds (AREA)
- Indole Compounds (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB36688/75A GB1572183A (en) | 1975-09-05 | 1975-09-05 | Cyclopropane carboxylic acid ester synthesis and intermediates therefor |
| JP51105674A JPS5233652A (en) | 1975-09-05 | 1976-09-03 | Process for manufacture of vinylcyclopropane carboxylic acid esters |
| CH1124676A CH627432A5 (en) | 1975-09-05 | 1976-09-03 | Process for the preparation of vinylcyclopropanecarboxylates |
| SE7609748A SE7609748L (sv) | 1975-09-05 | 1976-09-03 | Sett att framstella vinylcyklopropankarboxylatestras |
| BR7605865A BR7605865A (pt) | 1975-09-05 | 1976-09-03 | Processo para preparar um composto de vinila e compostos obtidos |
| IL50407A IL50407A (en) | 1975-09-05 | 1976-09-03 | Preparation of 2,2-dimethyl-3-dihalovinyl-cyclopropane-carboxylic acid derivatives and novel 2,2-dimethyl-3-(dihalo-alpha-hydroxyethyl)cyclopropanecarboxylic acid derivatives as intermediates therefor |
| NL7609841A NL7609841A (nl) | 1975-09-05 | 1976-09-03 | Werkwijze voor het bereiden van vinylesters met insektenverdelgende activiteit. |
| DE19762639777 DE2639777A1 (de) | 1975-09-05 | 1976-09-03 | Vinylcyclopropancarboxylatester und verfahren zu ihrer herstellung |
| IT51138/76A IT1068211B (it) | 1975-09-05 | 1976-09-03 | Procedimento per la produzione di esteri di vinilciclopropancarbos silato e prodotto ottenuto |
| FR7626608A FR2355797A1 (fr) | 1975-09-05 | 1976-09-03 | Procede de preparation de vinylcyclopropanes substitues utilisables dans la preparation d'insecticides |
| US05/720,347 US4289711A (en) | 1975-09-05 | 1976-09-03 | Ester synthesis |
| FR7714876A FR2351958A1 (fr) | 1975-09-05 | 1977-05-16 | Dimethylsulfuranylidene acetate de m-phenoxybenzyle et son procede de preparation |
| FR7714875A FR2351942A1 (fr) | 1975-09-05 | 1977-05-16 | Derives d'acide acetyl-3 dimethyl-2,2 cyclopropanecarboxylique utilisables dans la preparation d'insecticides |
| CH25282A CH636073A5 (en) | 1975-09-05 | 1982-01-15 | Process for the preparation of substituted cyclopropanecarboxylates |
| JP60089886A JPS60243042A (ja) | 1975-09-05 | 1985-04-25 | シクロプロパンカルボン酸誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB36688/75A GB1572183A (en) | 1975-09-05 | 1975-09-05 | Cyclopropane carboxylic acid ester synthesis and intermediates therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1572183A true GB1572183A (en) | 1980-07-23 |
Family
ID=10390361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB36688/75A Expired GB1572183A (en) | 1975-09-05 | 1975-09-05 | Cyclopropane carboxylic acid ester synthesis and intermediates therefor |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS60243042A (enrdf_load_stackoverflow) |
| BR (1) | BR7605865A (enrdf_load_stackoverflow) |
| CH (2) | CH627432A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2639777A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1572183A (enrdf_load_stackoverflow) |
| IL (1) | IL50407A (enrdf_load_stackoverflow) |
| IT (1) | IT1068211B (enrdf_load_stackoverflow) |
| NL (1) | NL7609841A (enrdf_load_stackoverflow) |
| SE (1) | SE7609748L (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113511964A (zh) * | 2021-03-18 | 2021-10-19 | 京博农化科技有限公司 | 一种用于定量定性分析的高含量2,2-二氯-1-(1-氯环丙基)乙酮的合成方法 |
| CN114478230A (zh) * | 2020-10-28 | 2022-05-13 | 中国科学院大连化学物理研究所 | 一种3-乙酰基-2,2-二甲基环丙烷羧酸的拆分方法 |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL56400A (en) * | 1976-09-21 | 1984-07-31 | Roussel Uclaf | Alpha-cyano-3-phenoxybenzyl and 3,4,5,6-tetrahydrophthalimidomethyl esters of 2,2-dimethyl-3-(1,2,2,2-tetrahaloethyl)cyclopropane-carboxylic acids,process for preparing them and insecticidal,acaricidal and nematocidal compositions containing them |
| DE2732213A1 (de) * | 1977-07-16 | 1979-01-25 | Bayer Ag | Derivate der cyclopropancarbonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als zwischenprodukte zur herstellung von insektiziden |
| US4277617A (en) * | 1977-10-27 | 1981-07-07 | Roussel Uclaf | Process for the preparation of esters |
| US4241081A (en) | 1978-10-23 | 1980-12-23 | Shell Oil Company | Cyclopropanecarboxylate pesticides |
| US4258207A (en) | 1978-10-23 | 1981-03-24 | Shell Oil Company | Cyclopropanecarboxylate pesticides preparation |
| DE2923773A1 (de) * | 1979-06-12 | 1980-12-18 | Bayer Ag | Verfahren zur herstellung von trans-3,3-dimethyl-cyclopropan-1,2-dicarbonsaeure |
| US4335253A (en) * | 1980-05-30 | 1982-06-15 | Shell Oil Company | Preparation of dihalovinyl compounds |
| EP0041283B1 (en) * | 1980-05-30 | 1985-07-24 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of dihalomethylene-lactones |
| CA1167048A (en) | 1980-10-22 | 1984-05-08 | Petrus A. Kramer | Cyclopropane derivatives, processes for their preparation and their use in the preparation of dihalovinylcyclopropane carboxylic acids |
| JPS57120548A (en) * | 1980-12-01 | 1982-07-27 | Shell Int Research | Manufacture of cyclopropane derivative |
| DE3225605A1 (de) * | 1981-07-10 | 1983-01-27 | Shell Internationale Research Maatschappij B.V., 2501 's-Gravenhage | Verfahren zur herstellung von cyclopropanderivaten |
| FR2549470B1 (fr) * | 1983-07-21 | 1985-12-27 | Roussel Uclaf | Procede de preparation d'esters d'alcoyle de l'acide cis-chrysanthemique et nouveaux intermediaires obtenus |
| FR2607133B1 (fr) * | 1986-11-20 | 1989-05-05 | Roussel Uclaf | Nouveaux derives de l'acide 2,2-dimethyl cyclopropane carboxylique portant en 3 une chaine halogenee saturee, leur procede de preparation et leur application comme pesticides |
-
1975
- 1975-09-05 GB GB36688/75A patent/GB1572183A/en not_active Expired
-
1976
- 1976-09-03 IT IT51138/76A patent/IT1068211B/it active
- 1976-09-03 CH CH1124676A patent/CH627432A5/de not_active IP Right Cessation
- 1976-09-03 NL NL7609841A patent/NL7609841A/xx not_active Application Discontinuation
- 1976-09-03 BR BR7605865A patent/BR7605865A/pt unknown
- 1976-09-03 DE DE19762639777 patent/DE2639777A1/de not_active Ceased
- 1976-09-03 SE SE7609748A patent/SE7609748L/ not_active Application Discontinuation
- 1976-09-03 IL IL50407A patent/IL50407A/xx unknown
-
1982
- 1982-01-15 CH CH25282A patent/CH636073A5/de not_active IP Right Cessation
-
1985
- 1985-04-25 JP JP60089886A patent/JPS60243042A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114478230A (zh) * | 2020-10-28 | 2022-05-13 | 中国科学院大连化学物理研究所 | 一种3-乙酰基-2,2-二甲基环丙烷羧酸的拆分方法 |
| CN114478230B (zh) * | 2020-10-28 | 2024-04-16 | 中国科学院大连化学物理研究所 | 一种3-乙酰基-2,2-二甲基环丙烷羧酸的拆分方法 |
| CN113511964A (zh) * | 2021-03-18 | 2021-10-19 | 京博农化科技有限公司 | 一种用于定量定性分析的高含量2,2-二氯-1-(1-氯环丙基)乙酮的合成方法 |
| CN113511964B (zh) * | 2021-03-18 | 2023-09-19 | 山东京博农化科技股份有限公司 | 一种用于定量定性分析的高含量2,2-二氯-1-(1-氯环丙基)乙酮的合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CH636073A5 (en) | 1983-05-13 |
| SE7609748L (sv) | 1977-03-06 |
| JPS60243042A (ja) | 1985-12-03 |
| NL7609841A (nl) | 1977-03-08 |
| IL50407A0 (en) | 1976-11-30 |
| JPS6220176B2 (enrdf_load_stackoverflow) | 1987-05-06 |
| DE2639777A1 (de) | 1977-03-10 |
| IL50407A (en) | 1983-05-15 |
| BR7605865A (pt) | 1977-08-16 |
| IT1068211B (it) | 1985-03-21 |
| CH627432A5 (en) | 1982-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |