CS266995B1 - Method of 2-methyl-6-etyl-n-(1-metoxy-2-propyl)aniline preparation - Google Patents
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Abstract
Riešenie sa týká spósobu pripravy 2- -metyl-6-etyl-N-/l'-metoxy-2'-propyl/- analínu hydrogenačnou alkyláciou 2-metyl- “6-etylanilínu v prostředí rozpúšťadla v přítomnosti hydrogenačného katalyzátora a platinového protonového katalyzátora zo skupiny zahrňujúcej 2-metyl-6-etylanilín hydrochlorid, 2-metyl-6-etylanilín semidihydrogénsulfát, 2-metyl-6-etylanilín trihydrogénfosfát, 2-mety1-6-ety1-N-/1'-metoxy- -2'-propyl/anilín hydrochlorid, 2-metyl- -6-etyl-N-/l"-metoxy-2'-propyl/anilín dihydrogénsultát a 2-metyl-6-etyl-N-/l'- -metoxy-2'-propy1/anilín di-/trihydrogénfosfát/ v množstve 1,0 až 12,5 % hmotnostných vzhladom na použitý 2-metyl-6- -etylanilín. Riešenie je možné využiť v chemickom priemysle pri výrobě chemických prostriedkov na ochranu rastlín.The solution relates to the 2- methyl-6-ethyl-N / l-methoxy-2-propyl / - by hydrogenation alkylation of 2-methyl- 6-ethylaniline in a solvent environment in the presence of a hydrogenation catalyst and a platinum proton catalyst 2-methyl-6-ethylaniline hydrochloride, 2-methyl-6-ethylaniline semidihydrogen sulfate, 2-methyl-6-ethylaniline trihydrogenphosphate, 2-mety1-6 ety1-N- / methoxy-1 ' -2'-propyl / aniline hydrochloride, 2-methyl- -6-ethyl-N- (1'-methoxy-2'-propyl) aniline dihydrogen sulfate and 2-methyl-6-ethyl-N- -methoxy-2'-propyl / aniline di- / trihydrogenphosphate / in an amount of 1.0 to 12.5% by weight with respect to the 2-methyl-6- -etylanilín. The solution can be used chemical industry in chemical production plant protection products.
Description
Vynález sa týká spósobu přípravy 2-metyl-6-etyl-N-/l-metoxy-2'-propyl/anilínu. Uvedená zlúčenína je medziproduktom na výrobu chemických prostriedkov na ochranu rastlín.The invention relates to a process for the preparation of 2-methyl-6-ethyl-N- (1-methoxy-2'-propyl) aniline. Said compound is an intermediate for the production of chemical plant protection products.
2,6-dialkyl-N-/l'-alkoxy-2'-propyl/anilíny sú už dlhšie známe z patentovej literatúry (US 2 387 071, US 2 759 943). 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilín je možné připravit napr. reakciou 2-metyl-6-etylanilínu s 2-halogén-l-metoxypropánom (US 3 937 730). Iný známy spósob jeho přípravy je založený na kondenzácii 2-metyl-6-etylanilínu s metoxypropanónom a súčasnej alebo následnej hydrogenácii výsledného 2-metyl-6-etyl-N-/l'-metoxy-2*-propylidén/anilínu (azometín) (US 3 937 730, US 4 022 611) . Známe je tiež, že takýto typ hydrogenačnej alkylácie sa uskutočňuje bez přítomnosti rozpúštadla (US 4 200 451, DE 2 328 340) alebo v prostředí rozpúštadla (BE 810 763, CS 219 856) v přítomnosti proténového a hydrogenačného katalyzátora (US 4 200 451). Protonový katalyzátor jednak urýchíuje kondenzačnú reakciu 2,6-dialkylanilínu s metoxypropanónom, výsledkom ktorej je příslušný azometín a jednak · aktivuje hydrogenačný katalyzátor na báze vzácného kovu pri paralelné prebiehajúcej hydrogenácii azometínu. Hydrogenačné katalyzátory na báze vzácných kovov, napr. paládia alebo platiny, sa totiž v priebehu hydrogenáoie dezaktivujú účinkom katalyzátorových jedov ako sú napr. rózne polymérne látky, dusíkaté zlúčeniny vrátane amínov a nukleofilné ióny. Známe je využitie kyseliny octovej (BE 810 763, CS 219 856) alebo kyseliny sírovej (US 4 200 451, DE 2 328 340) ako proténového katalyzátora pri hydrogenačnej alkylácii 2,6-disubstituovaných anilínov s alkoxypropanónmi.2,6-Dialkyl-N- (1'-alkoxy-2'-propyl) anilines have long been known from the patent literature (U.S. Pat. No. 2,387,071, U.S. Pat. No. 2,759,943). 2-methyl-6-ethyl-N- [1'-methoxy-2'-propyl] aniline can be prepared e.g. by reacting 2-methyl-6-ethylaniline with 2-halo-1-methoxypropane (US 3,937,730). Another known method for its preparation is based on the condensation of 2-methyl-6-ethylaniline with methoxypropanone and the simultaneous or subsequent hydrogenation of the resulting 2-methyl-6-ethyl-N- [1'-methoxy-2'-propylidene] aniline (azomethine) ( US 3,937,730, US 4,022,611). It is also known that this type of hydrogenation alkylation is carried out in the absence of a solvent (U.S. Pat. No. 4,200,451, DE 2,328,340) or in a solvent medium (BE 810,763, CS 219,856) in the presence of a protene and hydrogenation catalyst (U.S. Pat. No. 4,200,451). . The proton catalyst, on the one hand, accelerates the condensation reaction of 2,6-dialkylaniline with methoxypropanone, which results in the corresponding azomethine, and, on the other hand, activates the noble metal hydrogenation catalyst during the parallel hydrogenation of azomethine. Noble metal hydrogenation catalysts, e.g. palladium or platinum, are deactivated during hydrogenation by the action of catalyst poisons such as e.g. various polymeric substances, nitrogen compounds including amines and nucleophilic ions. It is known to use acetic acid (BE 810 763, CS 219 856) or sulfuric acid (U.S. Pat. No. 4,200,451, DE 2,328,340) as a protene catalyst in the hydrogenation alkylation of 2,6-disubstituted anilines with alkoxypropanones.
Teraz sa zistilo, že 2-metyl-6-etyl-N-/l'-metoxy-l'-propyl/anilín je možné připravit hydrogenačnou alkyláciou 2-metyl-6-etylanilínu metoxypropanónom v prostředí rozpúštadla a v přítomnosti protonového katalyzátora a platinového hydrogenačného katalyzátora podlá vynálezu, ktorého podstata spočívá v tom, že ako protonový katalyzátor sa použije aspoň jedna zlúčenína zo skupiny, zahřňajúcej 2-metyl-6-etylanilín hydrochlorid, 2-metyl-6-etylanilín semi-dihydrogénsulfát, 2-metyl-6~etylanilín trihydrogénfosfát, 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilín hydrochlorid, 2-metyl-6-etyl-N-/1'- metoxy-2'-propyl/anilín dihydrogénsulfát, 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilín di-/trihydrogénfosfát/ v množstve 1,0 až 12,5 % hmotnostných vzhladom na použitý 2-metyl-6-etylanilín.It has now been found that 2-methyl-6-ethyl-N- [1'-methoxy-1'-propyl] aniline can be prepared by hydrogenation alkylation of 2-methyl-6-ethylaniline with methoxypropanone in a solvent medium and in the presence of a proton catalyst and a platinum hydrogenation. of the catalyst according to the invention, which consists in using as proton catalyst at least one compound from the group consisting of 2-methyl-6-ethylaniline hydrochloride, 2-methyl-6-ethylaniline semi-dihydrogen sulphate, 2-methyl-6-ethylaniline trihydrogen phosphate, 2-methyl-6-ethyl-N- [1'-methoxy-2'-propyl] aniline hydrochloride, 2-methyl-6-ethyl-N- (1'-methoxy-2'-propyl) aniline dihydrogen sulfate, 2-methyl-6-ethyl-N- [1'-methoxy-2'-propyl] aniline di- (trihydrogen phosphate) in an amount of 1.0 to 12.5% by weight based on the 2-methyl-6-ethylaniline used.
Výhodou spósobu přípravy 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu podlá vynálezu je vysoký stupeň konverzie 2-metyl-6-etylanilínu s metoxypropanónom na příslušný azometín v dósledku vysokej katalytickej účinnosti použitého protonového katalyzátora pri zachovaní vysokej aktivity použitého hydrogenačného katalyzátora.An advantage of the process for the preparation of 2-methyl-6-ethyl-N- [1'-methoxy-2'-propyl] aniline according to the invention is the high degree of conversion of 2-methyl-6-ethylaniline with methoxypropanone to the corresponding azomethine due to the high catalytic efficiency of the proton. catalyst while maintaining the high activity of the hydrogenation catalyst used.
Protonové katalyzátory potřebné pre přípravu l-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu je možné pripraviť známým spósobom spočívajúcim v reakcii příslušného substituovaného anilínu s kyselinou chlorovodíkovou, sírovou alebo trihydrogénfosforečnou v prostředí organického rozpúštadla a izoláciou vzniklej kryštalickej látky.The proton catalysts required for the preparation of 1-methyl-6-ethyl-N- (1'-methoxy-2'-propyl) aniline can be prepared in a known manner by reacting the corresponding substituted aniline with hydrochloric, sulfuric or trihydrogenphosphoric acid in an organic solvent and isolating the resulting crystalline substance.
Nalsedujúce příklady ilustrujú ale neobmedzujú predmet vynálezu.The following examples illustrate but do not limit the scope of the invention.
Příklad 1Example 1
K roztoku 0,2 molu 2-metyl-6-etyl-6-etylanilínu v 50 ml benzénu sa za intenzívneho miešania postupné přidalo.0,2 molu 85 % kyseliny trihydrogénfosforečnej, vytvořená kryštalická sol sa odsala, premyla benzénom a vysušila. Získal sa 2«metyl-6-etylanilín trihydrogénfosfát s t. t. 156 až 161 °C v kvantitatívnom výťažku.To a solution of 0.2 mol of 2-methyl-6-ethyl-6-ethylaniline in 50 ml of benzene was added gradually, with vigorous stirring, 0.2 mol of 85% trihydrogenphosphoric acid, the crystalline salt formed was filtered off with suction, washed with benzene and dried. 2-Methyl-6-ethylaniline trihydrogen phosphate with m.p. t. 156-161 ° C in quantitative yield.
Analogickým postupom sa připravili tieto protonové katalyzátory:The following proton catalysts were prepared in an analogous manner:
2-metyl-6-etylanilín hydrochlorid sublimuje 80 °C2-Methyl-6-ethylaniline hydrochloride sublimes at 80 ° C
2-metyl-6-etylanilín semidihydrogénsulfát t. t. 100 až 145 °C2-methyl-6-ethylaniline semidihydrogen sulfate t. t. 100-145 ° C
2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilín hydrochlorid t. t. 135 až 150 C2-methyl-6-ethyl-N- [1'-methoxy-2'-propyl] aniline hydrochloride t. t. 135 to 150 C
CS 266 995 BlCS 266 995 Bl
2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilín dihydrogénsulfát n^ = 1,519 22-methyl-6-ethyl-N- [1'-methoxy-2'-propyl] aniline dihydrogen sulfate n ^ = 1,519 2
2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilín di/trihydrogénfosfát/ ηθ = 1,493 22-methyl-6-ethyl-N- [1'-methoxy-2'-propyl] aniline di (trihydrogen phosphate) ηθ = 1.493 2
Příklad 2Example 2
Zmes 9,0 g (0,065 molu) 2-metyl-6~etylanilínu, 7,1 g (0,08 molu) metoxypropanónu, 24,0 g l-metoxy-2~propanolu, 90 mg platinového hydrogenačného katalyzátora (nosič - aktivně uhlie) s obsahom kovu 5 % a 90 mg 2-metyl-6-etylanilín trihydrogénfosfátu sa hydrogenovala v autokláve s objemom 100 cm3, opatrenom vrtulovým miešadlom pri 50 °C a tlaku vodíka, 5,0 MPa počas 3,5 h. Potom z reakčnej zmesi odfiltroval hydrogenačný katalyzátor a oddestilovalo rozpúšfadlo, z destilačného zvyšku pozostávajúceho z dvoch fáz sa oddělil protonový katalyzátor a anilínová frakcia sa analyzovala metodou plynovéj chromatografie. Zistilo sa, že obsahuje: 1,6 % 2-metyl-6-etylanilínu, 0,3 % azometínu /2-metyl-6-etyl-N-/l'-metoxy-2'-propylidén/anilín/ a 97 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu.A mixture of 9.0 g (0.065 mol) of 2-methyl-6-ethylaniline, 7.1 g (0.08 mol) of methoxypropanone, 24.0 g of 1-methoxy-2-propanol, 90 mg of platinum hydrogenation catalyst (support - active carbon) with a metal content of 5% and 90 mg of 2-methyl-6-ethylaniline trihydrogen phosphate was hydrogenated in a 100 cm 3 autoclave equipped with a propeller stirrer at 50 ° C and hydrogen pressure, 5.0 MPa for 3.5 h. Then, the hydrogenation catalyst was filtered off from the reaction mixture, and the solvent was distilled off, the proton catalyst was separated from the distillation residue consisting of two phases, and the aniline fraction was analyzed by gas chromatography. It was found to contain: 1.6% 2-methyl-6-ethylaniline, 0.3% azomethine (2-methyl-6-ethyl-N- (1'-methoxy-2'-propylidene) aniline) and 97% 2-methyl-6-ethyl-N- [1'-methoxy-2'-propyl] aniline.
Příklad 3Example 3
Hydrogenáciou reakčnej zmesi rovnakého zloženia ako v příklade 2, s tým rozdielom, že protonový katalyzátor 2-metyl-6-etylanilín trihydrogénfosfát sa použil v množstve 427 mg, postupom podlá příkladu 2 sa získala reakčná zmes, ktorej anilínová frakcia podlá analýzy metodou plynovej chromatografie obsahovala: 0,4 % 2-metyl-6-etylanilínu, 0,1 % azometínu, 98,7 % 2-metyl-6-ety1-N-/1'-metoxy-2'-propyl/anilínu.Hydrogenation of a reaction mixture of the same composition as in Example 2, except that the proton catalyst 2-methyl-6-ethylaniline trihydrogen phosphate was used in an amount of 427 mg, the procedure of Example 2 gave a reaction mixture whose aniline fraction was analyzed by gas chromatography. : 0.4% 2-methyl-6-ethylaniline, 0.1% azomethine, 98.7% 2-methyl-6-ethyl-N- [1'-methoxy-2'-propyl] aniline.
Příklad 4Example 4
Hydrogénáciou reakčnej zmesi rovnakého zloženia ako v příklade 2, s tým rozdielom, že sa protonový katalyzátor 2-metyl-6-etylanilín trihydrogénfosfát použil v množstve 640 mg, postupom podlá příkladu 2 sa získala reakčná zmes, ktorej anilínová frakcia podlá analýzy metodou plynovej chromatografie obsahovala: 0,1 % 2-metyl-6-etylanilínu, 99,6 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu, azometín neobsahovala.Hydrogenation of a reaction mixture of the same composition as in Example 2, except that the proton catalyst 2-methyl-6-ethylaniline trihydrogen phosphate was used in an amount of 640 mg, the procedure of Example 2 gave a reaction mixture whose aniline fraction was analyzed by gas chromatography. : 0.1% 2-methyl-6-ethylaniline, 99.6% 2-methyl-6-ethyl-N- [1'-methoxy-2'-propyl] aniline, azomethine free.
Příklad 5Example 5
Hydrogenáciou reakčnej zmesi rovnakého zloženia ako v příklade 2, s tým rozdielom, že protonový katalyzátor 2-metyl-6-etylanilín trihydrogénfosfát sa použil v množstve 1,1 g, postupom podlá příkladu 2 sa získala reakčná zmes, ktorej anilínová frakcia podlá analýzy metodou plynovej chromatografie obsahovala 99,6 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu a neobsahovala ani nezreagovaný 2-metyl-6-etylanilín ani azometín.Hydrogenation of a reaction mixture of the same composition as in Example 2, except that the proton catalyst 2-methyl-6-ethylaniline trihydrogen phosphate was used in an amount of 1.1 g, the reaction mixture of Example 2 gave a reaction mixture whose aniline fraction was analyzed by gas chromatography contained 99.6% 2-methyl-6-ethyl-N- [1'-methoxy-2'-propyl] aniline and contained neither unreacted 2-methyl-6-ethylaniline nor azomethine.
Příklad 6Example 6
Hydrogenáciou reakčnej zmesi rovnakého zloženia ako v příklade 2, s tým rozdielom, že ako protonový katalyzátor sa použil 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilín di-/trihydrogénfosfát/ v množstve 740 mg, postupom podlá příkladu 2 sa získala reakčná zmes, ktorej anilínová frakcia podlá analýzy metodou plynovej chromatografie obsahovala: 0,3 % 2-metyl-6-etylanilínu, 98,9 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu, azometín neobsahovala.Hydrogenation of a reaction mixture of the same composition as in Example 2, except that 2-methyl-6-ethyl-N- (1'-methoxy-2'-propyl) aniline di- (trihydrogen phosphate) was used as a proton catalyst in an amount of 740 mg, according to the procedure of Example 2, a reaction mixture was obtained, the aniline fraction of which, according to analysis by gas chromatography, contained: 0.3% of 2-methyl-6-ethylaniline, 98.9% of 2-methyl-6-ethyl-N- [1 ' -methoxy-2'-propyl / aniline, azomethine free.
Příklad 7.Example 7.
Hydrogenáciou reakčnej zmesi rovnakého zloženia ako v příklade 2, s tým rozdielom, že ako protonový katalyzátor sa použil 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilín di-/trihydrogénfosfát/ v množstve 1,1 g, postupom podlá příkladu 2 sa získala reakčná zmes, ktorej anilínová frakcia podlá analýzy metodou plynovej chromatografie obsahovala: 99,7 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu, pričom neobsahovala ani nezreagovaný 2-metyl-6-etylanilín ani azometín.By hydrogenation of a reaction mixture of the same composition as in Example 2, except that 2-methyl-6-ethyl-N- (1'-methoxy-2'-propyl) aniline di- (trihydrogen phosphate) was used as a proton catalyst in an amount of 1 , 1 g, according to the procedure of Example 2, a reaction mixture was obtained, the aniline fraction of which, according to analysis by gas chromatography, contained: 99.7% of 2-methyl-6-ethyl-N- [1'-methoxy-2'-propyl] aniline, containing neither unreacted 2-methyl-6-ethylaniline nor azomethine.
CS 266 995 BlCS 266 995 Bl
Příklad 8Example 8
Hydrogenáciou reakčnej zmesi rovnakého zloženia ako v příklade 2, s tým rozdielom, že ako protonový katalyzátor sa použil 2-metyl-6-etylanilín semidihydrogénsulfát v množstveBy hydrogenating a reaction mixture of the same composition as in Example 2, except that 2-methyl-6-ethylaniline semidihydrogen sulfate was used as the proton catalyst in an amount of
677 mg, postupom podlá příkladu 2 sa získala reakčná zmes, ktorej anilínová frakcia podlá analýzy metodou plynovej chromatografie obsahovala: 6,4 % 2-metyl-6-N-/l'-metoxy-2'-propyl/anilínu. '677 mg, according to the procedure of Example 2, a reaction mixture was obtained, the aniline fraction of which, according to analysis by gas chromatography, contained: 6.4% of 2-methyl-6-N- (1'-methoxy-2'-propyl) aniline. '
Příklad 9Example 9
Hydrogenáciou reakčnej zmesi rovnakého zloženia ako v příklade 2, s tým rozdielom, že ako protonový katalyzátor sa použil 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilín dihydrogénsulfát v množstve 540 mg sa získala výsledná reakčná zmes, ktorej anilínová frakcia podlá analýzy metodou plynovej chromatografie obsahovala: 3,8 % 2-metyl-6-etylanilínu, 0,2 % azometínu, 93,8 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu.Hydrogenation of a reaction mixture of the same composition as in Example 2, except that 2-methyl-6-ethyl-N- [1'-methoxy-2'-propyl] aniline dihydrogen sulfate was used as a proton catalyst in an amount of 540 mg to give the final reaction mixture, the aniline fraction of which according to the analysis by gas chromatography contained: 3.8% of 2-methyl-6-ethylaniline, 0.2% of azomethine, 93.8% of 2-methyl-6-ethyl-N- [1'-methoxy -2'-propyl / aniline.
Příklad 10Example 10
Zmes 9,0 g (0,066 5 molu) 2-metyl-6-etylanilínu, 7,1 g (0,08 molu) metoxypropanónu, 24,0 g l-metoxy-2-propanolu, 90 mg platinového hydrogenančného katalyzátore (nosič - aktivně uhlie) s obsahom kovu 5 % a 450 mg 2-metyl-6-etylanilín hydrochloridu sa hydrogenovala v autokláve s objemom 100 cm3 vrtulovým miešadlom pri 50 °C a tlaku vodíka 5,0 MPa počas 3,5 h. Potom sa z reakčnej zmesi odfiltroval hydrogenačný katalyzátor, oddestilovalo sa rozpúšťadlo a anilínová frakcia destilačného zvyšku sa analyzovala metodou plynovej chromatografie. Zistilo sa, že obsahuje 4,5 % 2-metyl-6-etylanilínu, 94,8 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu a že neobsahuje'azometín.A mixture of 9.0 g (0.066 mol) of 2-methyl-6-ethylaniline, 7.1 g (0.08 mol) of methoxypropanone, 24.0 g of 1-methoxy-2-propanol, 90 mg of platinum hydrogenation catalyst (support - activated carbon) with a metal content of 5% and 450 mg of 2-methyl-6-ethylaniline hydrochloride was hydrogenated in a 100 cm 3 autoclave with a propeller stirrer at 50 ° C and a hydrogen pressure of 5.0 MPa for 3.5 h. Then, the hydrogenation catalyst was filtered off from the reaction mixture, the solvent was distilled off, and the aniline fraction of the distillation residue was analyzed by gas chromatography. It was found to contain 4.5% 2-methyl-6-ethylaniline, 94.8% 2-methyl-6-ethyl-N- [1'-methoxy-2'-propyl] aniline and no azomethine.
Příklad 11Example 11
Hydrogenáciou reakčnej zmesi rovnakého zloženia ako v příklade 10, s tým rozdielom, že ako protonový katalyzátor sa použil 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilín trihydrogénfosfát v množstve 0,9 g sa získala výsledná reakčná zmes, ktorej anilínová frakcia podlá analýzy metodou plynovej chromatografie obsahovala: 1,8 % 2-metyl-6-etylanilínu, 0,1 % azometínu, 97,8 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu.Hydrogenation of a reaction mixture of the same composition as in Example 10, except that 2-methyl-6-ethyl-N- [1'-methoxy-2'-propyl] aniline trihydrogen phosphate was used as the proton catalyst in an amount of 0.9 g, obtained the resulting reaction mixture, the aniline fraction of which according to the analysis by gas chromatography contained: 1.8% of 2-methyl-6-ethylaniline, 0.1% of azomethine, 97.8% of 2-methyl-6-ethyl-N- [1 ' -methoxy-2'-propyl / aniline.
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| CN109280012A (en) * | 2017-07-19 | 2019-01-29 | 山东侨昌化学有限公司 | A kind of uninanned platform isopropyl methoxalamine intermediate 2- ethyl -6- methyl-N-(1 '-methoxyl group -2 '-propyl) aniline method |
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1988
- 1988-06-20 CS CS884267A patent/CS266995B1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109280012A (en) * | 2017-07-19 | 2019-01-29 | 山东侨昌化学有限公司 | A kind of uninanned platform isopropyl methoxalamine intermediate 2- ethyl -6- methyl-N-(1 '-methoxyl group -2 '-propyl) aniline method |
Also Published As
| Publication number | Publication date |
|---|---|
| CS426788A1 (en) | 1989-05-12 |
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