KR101335861B1 - 고순도 Ｄ-(-)-Ｎ, Ｎ-디에틸-2-(α-나프톡시)프로피온아미드의 제조방법 - Google Patents
고순도 Ｄ-(-)-Ｎ, Ｎ-디에틸-2-(α-나프톡시)프로피온아미드의 제조방법 Download PDFInfo
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- KR101335861B1 KR101335861B1 KR1020137017504A KR20137017504A KR101335861B1 KR 101335861 B1 KR101335861 B1 KR 101335861B1 KR 1020137017504 A KR1020137017504 A KR 1020137017504A KR 20137017504 A KR20137017504 A KR 20137017504A KR 101335861 B1 KR101335861 B1 KR 101335861B1
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- KR
- South Korea
- Prior art keywords
- diethyl
- propionamide
- naphthoxy
- purity
- product
- 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.)
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- 229910052757 nitrogen Inorganic materials 0.000 title claims abstract description 127
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 238000000034 method Methods 0.000 title claims abstract description 63
- 229940080818 propionamide Drugs 0.000 title claims abstract description 63
- 230000008569 process Effects 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- -1 α-naphthoxy Chemical group 0.000 claims abstract description 66
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 46
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 34
- 238000002360 preparation method Methods 0.000 claims description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- 239000003495 polar organic solvent Substances 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 33
- 239000012872 agrochemical composition Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 65
- 238000006243 chemical reaction Methods 0.000 description 47
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000002904 solvent Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
- 239000008187 granular material Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 150000001408 amides Chemical class 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- WXZVAROIGSFCFJ-UHFFFAOYSA-N N,N-diethyl-2-(naphthalen-1-yloxy)propanamide Chemical compound C1=CC=C2C(OC(C)C(=O)N(CC)CC)=CC=CC2=C1 WXZVAROIGSFCFJ-UHFFFAOYSA-N 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
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- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
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- 239000000843 powder Substances 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- 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 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000004996 alkyl benzenes Chemical class 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
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- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
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- 235000010493 xanthan gum Nutrition 0.000 description 4
- NNDSWZHPHAJULZ-UHFFFAOYSA-N 4-chloro-1-(ethylamino)pentan-3-one Chemical compound CCNCCC(=O)C(C)Cl NNDSWZHPHAJULZ-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
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- 238000000638 solvent extraction Methods 0.000 description 3
- 239000004546 suspension concentrate Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 description 2
- RGVIYLQXUDJMCP-UHFFFAOYSA-N 2-tridecylphenol Chemical compound CCCCCCCCCCCCCC1=CC=CC=C1O RGVIYLQXUDJMCP-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 239000005585 Napropamide Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000003965 capillary gas chromatography Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
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- 239000002577 cryoprotective agent Substances 0.000 description 2
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- 239000003337 fertilizer Substances 0.000 description 2
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- 239000010410 layer Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
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- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- JEQDSBVHLKBEIZ-REOHCLBHSA-N (2s)-2-chloropropanoyl chloride Chemical compound C[C@H](Cl)C(Cl)=O JEQDSBVHLKBEIZ-REOHCLBHSA-N 0.000 description 1
- WXZVAROIGSFCFJ-CYBMUJFWSA-N (R)-napropamide Chemical compound C1=CC=C2C(O[C@H](C)C(=O)N(CC)CC)=CC=CC2=C1 WXZVAROIGSFCFJ-CYBMUJFWSA-N 0.000 description 1
- GAWAYYRQGQZKCR-REOHCLBHSA-N (S)-2-chloropropanoic acid Chemical compound C[C@H](Cl)C(O)=O GAWAYYRQGQZKCR-REOHCLBHSA-N 0.000 description 1
- 150000004782 1-naphthols Chemical class 0.000 description 1
- VPSKMQYCSCPAGT-UHFFFAOYSA-N 2-bromo-n,n-diethylpropanamide Chemical compound CCN(CC)C(=O)C(C)Br VPSKMQYCSCPAGT-UHFFFAOYSA-N 0.000 description 1
- MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 1
- KZLYQYPURWXOEW-UHFFFAOYSA-N 2-iodopropanoic acid Chemical compound CC(I)C(O)=O KZLYQYPURWXOEW-UHFFFAOYSA-N 0.000 description 1
- KTAVXDDWEGVLRN-UHFFFAOYSA-N 2-naphthalen-1-yloxypropanoic acid Chemical compound C1=CC=C2C(OC(C)C(O)=O)=CC=CC2=C1 KTAVXDDWEGVLRN-UHFFFAOYSA-N 0.000 description 1
- LNHXBWLDIXXFPF-UHFFFAOYSA-O 3-[4-[[4-(3-sulfoanilino)phenyl]-[4-(4-sulfoanilino)phenyl]methyl]anilino]benzenesulfonic acid Chemical compound OS(=O)(=O)c1ccc(Nc2ccc(cc2)[C+](c2ccc(Nc3cccc(c3)S(O)(=O)=O)cc2)c2ccc(Nc3cccc(c3)S(O)(=O)=O)cc2)cc1 LNHXBWLDIXXFPF-UHFFFAOYSA-O 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 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 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
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- 239000002585 base Substances 0.000 description 1
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- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
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- 239000008202 granule composition Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
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- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- YKOQQFDCCBKROY-UHFFFAOYSA-N n,n-diethylpropanamide Chemical compound CCN(CC)C(=O)CC YKOQQFDCCBKROY-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
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- 239000002798 polar solvent Substances 0.000 description 1
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- 239000003755 preservative agent Substances 0.000 description 1
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- 238000012545 processing Methods 0.000 description 1
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- 230000007017 scission Effects 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical group [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
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- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
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- 229960003080 taurine Drugs 0.000 description 1
- 238000003971 tillage Methods 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN858MU2007 | 2007-05-04 | ||
| IN858/MUM/2007 | 2007-05-04 | ||
| PCT/IN2008/000284 WO2009004642A2 (en) | 2007-05-04 | 2008-05-05 | PROCESS FOR MANUFACTURE OF HIGH PURITY D-(-)-N, N-DIETHYL-2-(α- NAPHTHOXY) PROPIONAMIDE |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020127008756A Division KR20120055724A (ko) | 2007-05-04 | 2008-05-05 | 고순도 Ｄ-(-)-Ｎ, Ｎ-디에틸-2-(α-나프톡시)프로피온아미드의 제조방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20130087610A KR20130087610A (ko) | 2013-08-06 |
| KR101335861B1 true KR101335861B1 (ko) | 2013-12-02 |
Family
ID=40226628
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020137017504A Active KR101335861B1 (ko) | 2007-05-04 | 2008-05-05 | 고순도 Ｄ-(-)-Ｎ, Ｎ-디에틸-2-(α-나프톡시)프로피온아미드의 제조방법 |
| KR1020127008756A Ceased KR20120055724A (ko) | 2007-05-04 | 2008-05-05 | 고순도 Ｄ-(-)-Ｎ, Ｎ-디에틸-2-(α-나프톡시)프로피온아미드의 제조방법 |
| KR1020097024802A Active KR101174962B1 (ko) | 2007-05-04 | 2008-05-05 | 고순도 Ｄ-(-)-Ｎ, Ｎ-디에틸-2-(α-나프톡시)프로피온아미드의 제조방법 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020127008756A Ceased KR20120055724A (ko) | 2007-05-04 | 2008-05-05 | 고순도 Ｄ-(-)-Ｎ, Ｎ-디에틸-2-(α-나프톡시)프로피온아미드의 제조방법 |
| KR1020097024802A Active KR101174962B1 (ko) | 2007-05-04 | 2008-05-05 | 고순도 Ｄ-(-)-Ｎ, Ｎ-디에틸-2-(α-나프톡시)프로피온아미드의 제조방법 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8309765B2 (https=) |
| EP (1) | EP2146574B2 (https=) |
| JP (1) | JP2010526059A (https=) |
| KR (3) | KR101335861B1 (https=) |
| CN (1) | CN101677538B (https=) |
| ES (1) | ES2556230T5 (https=) |
| HU (1) | HUE026533T2 (https=) |
| PL (1) | PL2146574T5 (https=) |
| RU (1) | RU2458047C2 (https=) |
| UA (1) | UA103460C2 (https=) |
| WO (1) | WO2009004642A2 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8557293B2 (en) * | 2010-08-26 | 2013-10-15 | Scott May | Sunscreen compositions for application to plants |
| CN102887832B (zh) * | 2012-09-29 | 2014-07-16 | 西安近代化学研究所 | 一种水相反应合成大位阻氯乙酰胺化合物的方法 |
| US9307765B2 (en) * | 2013-03-15 | 2016-04-12 | Upl Limited | Selective weed control using D-napropamide |
| TR201900984T4 (tr) * | 2013-03-15 | 2019-02-21 | Upl Ltd | D-napropamid kullanılarak selektif yabani ot kontrolü. |
| JP2017533892A (ja) * | 2014-10-03 | 2017-11-16 | ピュラック バイオケム ビー． ブイ． | Ｎ，ｎ−ジアルキルラクトアミドの製造法 |
| CN106397240A (zh) * | 2015-07-29 | 2017-02-15 | 国药集团化学试剂有限公司 | 2-卤代乙酰胺的合成方法 |
| US20220071205A1 (en) | 2018-12-21 | 2022-03-10 | Upl Ltd | Herbicide |
| CA3244493A1 (en) | 2021-12-29 | 2023-07-06 | UPL Corporation Limited | HERBICIDE MIXTURES |
| WO2025012825A1 (en) | 2023-07-11 | 2025-01-16 | Upl Mauritius Limited | Herbicide safener combinations and compositions |
| CN119504473B (zh) * | 2024-11-22 | 2026-04-14 | 国网安徽省电力有限公司电力科学研究院 | 一种采用六氟化硫制备敌草胺的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3718455A (en) * | 1970-07-20 | 1973-02-27 | Stauffer Chemical Co | Method of combatting weeds with {60 -naphthoxy acetamides |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU102735A1 (ru) * | 1952-06-14 | 1955-11-30 | А.П. Арендарук | Способ получени пара-нитро-альфа-ацетил-амино-бета-оксипропиофенона |
| US3480671A (en) * | 1969-01-16 | 1969-11-25 | Stauffer Chemical Co | Alpha-naphthoxy acetamide compositions |
| US3998880A (en) * | 1975-08-15 | 1976-12-21 | Stauffer Chemical Company | Production of N,N-diethyl 2(α-naphthoxy)propionamide |
| FR2460286A1 (fr) * | 1979-06-29 | 1981-01-23 | Rhone Poulenc Agrochimie | Procede de preparation d'acide phenoxy-2 propioniques optiquement actifs |
| US4358612A (en) | 1981-01-02 | 1982-11-09 | Stauffer Chemical Company | Process for production of α-haloalkylamides |
| US4548641A (en) | 1982-11-15 | 1985-10-22 | Stauffer Chemical Company | Herbicides: N,N-dialkyl-2-(4-substituted-1-naphthoxy) propionamides |
| US4668628A (en) * | 1985-04-01 | 1987-05-26 | Stauffer Chemical Company | Resolution of racemic mixtures of aliphatic acid esters |
| DE3778359D1 (de) * | 1987-07-07 | 1992-05-21 | Rhone Poulenc Sante | Verfahren zur herstellung von derivaten von pristinamycin iib. |
| JPH01168638A (ja) * | 1987-12-25 | 1989-07-04 | Mitsui Toatsu Chem Inc | 光学活性２−クロロプロピオン酸の製造方法 |
| CN1315868C (zh) * | 2005-10-14 | 2007-05-16 | 邢将军 | 丙－谷二肽的制造方法 |
-
2008
- 2008-05-05 WO PCT/IN2008/000284 patent/WO2009004642A2/en not_active Ceased
- 2008-05-05 HU HUE08826025A patent/HUE026533T2/en unknown
- 2008-05-05 KR KR1020137017504A patent/KR101335861B1/ko active Active
- 2008-05-05 JP JP2010505017A patent/JP2010526059A/ja active Pending
- 2008-05-05 UA UAA200912550A patent/UA103460C2/ru unknown
- 2008-05-05 CN CN200880014709.XA patent/CN101677538B/zh active Active
- 2008-05-05 ES ES08826025T patent/ES2556230T5/es active Active
- 2008-05-05 KR KR1020127008756A patent/KR20120055724A/ko not_active Ceased
- 2008-05-05 US US12/598,752 patent/US8309765B2/en active Active
- 2008-05-05 EP EP08826025.2A patent/EP2146574B2/en active Active
- 2008-05-05 RU RU2009144977/04A patent/RU2458047C2/ru active
- 2008-05-05 KR KR1020097024802A patent/KR101174962B1/ko active Active
- 2008-05-05 PL PL08826025.2T patent/PL2146574T5/pl unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3718455A (en) * | 1970-07-20 | 1973-02-27 | Stauffer Chemical Co | Method of combatting weeds with {60 -naphthoxy acetamides |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101677538B (zh) | 2017-06-06 |
| UA103460C2 (ru) | 2013-10-25 |
| WO2009004642A2 (en) | 2009-01-08 |
| EP2146574A4 (en) | 2012-02-29 |
| EP2146574B1 (en) | 2015-11-04 |
| RU2458047C2 (ru) | 2012-08-10 |
| US20100144532A1 (en) | 2010-06-10 |
| KR20130087610A (ko) | 2013-08-06 |
| ES2556230T3 (es) | 2016-01-14 |
| RU2009144977A (ru) | 2011-06-10 |
| CN101677538A (zh) | 2010-03-24 |
| KR20120055724A (ko) | 2012-05-31 |
| KR101174962B1 (ko) | 2012-08-20 |
| HUE026533T2 (en) | 2016-06-28 |
| JP2010526059A (ja) | 2010-07-29 |
| US8309765B2 (en) | 2012-11-13 |
| WO2009004642A3 (en) | 2009-07-02 |
| KR20090131679A (ko) | 2009-12-29 |
| PL2146574T5 (pl) | 2023-06-12 |
| PL2146574T3 (pl) | 2016-03-31 |
| EP2146574A2 (en) | 2010-01-27 |
| ES2556230T5 (es) | 2023-01-04 |
| EP2146574B2 (en) | 2022-11-02 |
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