CS266996B1 - Method of 2,6-dialkyl-n-(-methoxy-2-propyl)aniline preparation - Google Patents
Method of 2,6-dialkyl-n-(-methoxy-2-propyl)aniline preparation Download PDFInfo
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- CS266996B1 CS266996B1 CS884268A CS426888A CS266996B1 CS 266996 B1 CS266996 B1 CS 266996B1 CS 884268 A CS884268 A CS 884268A CS 426888 A CS426888 A CS 426888A CS 266996 B1 CS266996 B1 CS 266996B1
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- methoxy
- methyl
- methoxypropanone
- dialkylaniline
- propyl
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title description 62
- 238000000034 method Methods 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 abstract description 56
- 239000003054 catalyst Substances 0.000 abstract description 38
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 29
- 239000001257 hydrogen Substances 0.000 abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 26
- CUZLJOLBIRPEFB-UHFFFAOYSA-N 1-methoxypropan-2-one Chemical compound COCC(C)=O CUZLJOLBIRPEFB-UHFFFAOYSA-N 0.000 abstract description 24
- 239000000203 mixture Substances 0.000 abstract description 22
- 239000011541 reaction mixture Substances 0.000 abstract description 22
- 239000002253 acid Substances 0.000 abstract description 19
- 230000029936 alkylation Effects 0.000 abstract description 16
- 238000005804 alkylation reaction Methods 0.000 abstract description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001448 anilines Chemical class 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- 239000004476 plant protection product Substances 0.000 abstract description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 238000012824 chemical production Methods 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 48
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 description 29
- 229910052697 platinum Inorganic materials 0.000 description 24
- 229910052751 metal Inorganic materials 0.000 description 18
- 239000002184 metal Substances 0.000 description 18
- 238000004817 gas chromatography Methods 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N activated carbon Substances [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000003245 coal Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- -1 2,6-disubstituted anilines Chemical class 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Riešenie sa týká spósobu pripravy 2,6- -dialkyl-N-/l'-metoxy-2'-propyl/anilínov, v ktorých alkylové skupiny móžu byť rovnaké alebo rózne a znamenajú metyl alebo etyl, hydrogenačnou alkyláciou příslušných 2,6- -dialkylanilínov metoxypropanónom pri molárnom pomere 2,6-dialkylanilínu a metoxypropanónu 1:1,1 až 2, koncentrácii 2,6-dialkylanilínu v reakčnej zmesi 10 až 50 % hmot., v prostředí l-metoxy-2-propanolu alebo jeho zmesi s vodou v hmotnostnom pomere 100:1 až 70:30, v přítomnosti kyseliny trihydrogénfosforečnej alebo kyseliny chlórovodíkovej ako protonového katalyzátora v množstve 0,5 až 6,0 % hmot. vzhladom na použitý 2,6-dialkylanilín, pri teplote 20 až 100 °C a tlaku vodíka 0,1 až 0,7 MPa. Riešenie je možné využiť v chemickom priemysle pri výrobě chemických prostriedkov na ochranu rastlín.The solution relates to the 2.6- dialkyl-N / l-methoxy-2 ' -propyl / anilines in which the alkyl groups can be the same or rust and are methyl or ethyl, hydrogenation alkylation of the respective 2,6- -dialkylanilines by methoxypropanone at molar ratio of 2,6-dialkylaniline and methoxypropanone 1: 1.1 to 2, the concentration of 2,6-dialkylaniline in the reaction mixture 10 to 50% %, in 1-methoxy-2-propanol or mixtures thereof with water by weight 100: 1 to 70:30 in the presence of acid phosphoric acid or acid hydrogen chloride as proton catalyst in an amount of 0.5 to 6.0 wt. relative to the 2,6-dialkylaniline used at a temperature of 20 to 100 ° C and a hydrogen pressure of 0.1 up to 0.7 MPa. The solution can be used chemical industry in chemical production plant protection products.
Description
Vynález sa týká spósobu přípravy 2,6-dialkyl-N-/l*-metoxy-2'-propyl/anilínov. Uvedené zlúčeniny sú medziproduktami na výrobu chemických prostriedkov na ochranu rastlín.The invention relates to a process for the preparation of 2,6-dialkyl-N- (1'-methoxy-2'-propyl) anilines. Said compounds are intermediates for the production of chemical plant protection products.
2,6-dialkyl-N-/l'-alkoxy-2'-propyl/aniJ.íny sú už dlhšie známe z patentovej lietratúry (US 2 387 071, US 2 759 943). Připravit ich možno napr. reakciou 2,6-dialkylanilínov s 2-halogén-l-alkoxypropánom (US 3 973 730). Iný známy spósob ich přípravy je založený na kondenzácii 2,6-dialkylanilínov s alkoxypropanónom a súčasnej alebo následnéj hydrogenácii výsledného 2,6-dialkyl-N-/l'-alkoxy-2'-propyl/anilínu (azometín) (US 3 937 730, US 4 022 611). Známe je tiež, že takýto typ hydrogenačnej alkylácie sa uskutečňuje v přítomnosti protonového katalýzátora a hydrogenačného katalýzátora na báze vzácných kovov (US 4 200 451), bez přítomnosti rozpúštadla (US 4 200 451, DE 2 328 340) alebo v prostředí rozpúštadla (BE 810 763, CS 219 856). Protonový katalyzátor jednak urýchluje kondenzačnú reakciu 2,6-dialkylanilínu s alkoxypropanónom a jednak aktivuje hydrogenačný katalyzátor na báze vzácného kovu pri paralelné prebiehajúcej hydrogenácii azometínu. Hyrogenačné katalyzátory na báze vzácných kovov, napr. paládia alebo platiny sa totiž v priebehu hydrogenácie dezaktivujú účinkom katalyzátorových jedov ako sú napr. rózne polymérne látky, dusíkaté zlúčeniny, vrátane amínov a nukleofilné ióny.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). They can be prepared e.g. by reacting 2,6-dialkylanilines with 2-halo-1-alkoxypropane (US 3,973,730). Another known process for their preparation is based on the condensation of 2,6-dialkylanilines with alkoxypropanone and the simultaneous or subsequent hydrogenation of the resulting 2,6-dialkyl-N- [1'-alkoxy-2'-propyl] aniline (azomethine) (U.S. Pat. No. 3,937,730). , U.S. Pat. No. 4,022,611). It is also known that this type of hydrogenation alkylation is carried out in the presence of a proton catalyst and a noble metal hydrogenation catalyst (U.S. Pat. No. 4,200,451), 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). The proton catalyst, on the one hand, accelerates the condensation reaction of 2,6-dialkylaniline with alkoxypropanone and, on the other hand, activates the noble metal hydrogenation catalyst during the parallel hydrogenation of azomethine. Hybridization catalysts based on noble metals, 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.
Z literatúry je známe, že pri hydrogenačnej alkylácii 2,6-disubstituovaných anilínov. alkoxypropanónmi je možné ako protonový katalyzátor použit kyselinu octovú (BE 810 763) alebo kyselinu sírovú (US 4 200 451, DE 2 328 340). Nevýhodou kyseliny octovéj ako protonového katalýzátora je, že sa musí používat vo velkom přebytku a že jej izolácia z reakčnej zmesi je obtiažna. Pri použití kyseliny sírovej ako protonového katalyzátore je nevyhnuté túto po ukončení reakcie neutralizovat, aby pri izolácii reakčného produktu destiláciou nedochádzalo k jeho sulfonácii.It is known from the literature that in the hydrothylation of 2,6-disubstituted anilines. alkoxypropanones, acetic acid (BE 810 763) or sulfuric acid (U.S. Pat. No. 4,200,451, DE 2,328,340) can be used as proton catalyst. The disadvantage of acetic acid as a proton catalyst is that it must be used in large excess and that its isolation from the reaction mixture is difficult. When using sulfuric acid as a proton catalyst, it is necessary to neutralize it after completion of the reaction, so that the reaction product is not sulfonated when it is isolated by distillation.
Známa je tiež hydrogenačná alkylácia substituovaných anilínov v zmesi alkoholu a kyseliny octovej (BE 810 763, CS 219 856). K najlepším rozpúštadlám na hydrogenačnú alkyláciu patria alifatické alkoholy (metanol, etanol), ktoré dobré rozpúštajú ako východzie látky, protonový katalyzátor a vodík, tak aj intermediárny azometín, reakčný produkt a reakčnú vodu. Ako rozpúštadlá hydrogenačných zmesi v přítomnosti platinových hydrogenačných katalyzátorov majú však nižšie primárné alkoholy nevýhodu, ktorá spočívá v ich lahkej zápalnosti ako i samozápalnoti platiny.Hydrogenation alkylation of substituted anilines in a mixture of alcohol and acetic acid is also known (BE 810 763, CS 219 856). The best solvents for the hydrogenation alkylation include aliphatic alcohols (methanol, ethanol), which dissolve well the starting materials, the proton catalyst and hydrogen, as well as the intermediate azomethine, the reaction product and the water of reaction. However, as solvents for hydrogenation mixtures in the presence of platinum hydrogenation catalysts, lower primary alcohols have the disadvantage of their low flammability as well as the autoignition of platinum.
Uvedené nedostatky odstraňuje spósob přípravy 2,6-dialkyl-N-/l'-metoxy-2'-propyl/anilínov všeobecného vzorca IThe process for the preparation of 2,6-dialkyl-N- (1'-methoxy-2'-propyl) anilines of the formula I overcomes these drawbacks.
ch3 nh-ch-ch2-o-ch3 /1/CH 3 NH-CH-CH 2 -O-CH 3/1 /
2 kde R a R sú rovnaké alebo rózne a znamenajú metyl alebo etyl, hydrogenačnou alkyláciou2 wherein R 1 and R 2 are the same or different and represent methyl or ethyl, by hydrogen alkylation
2,6-dialkylanilínov všeobecného vzorca II2,6-dialkylanilines of general formula II
2 kde R a R majú už uvedený význam,2 wherein R and R are as defined above,
/11/ metoxypropanónom v prostředí rozpúštadla a v přítomnosti protonového katalýzátora a platinové ho hydrogenačného katalýzátora podlá vynálezu, ktorého podstata spočívá v tom, že hydrogenačná alkylácia sa uskutečňuje pri molárnom pomere 2,6-dialkylanilínu a metoxypropanónu 1:1,1 až 2, koncentrácii 2,6-dialkylanilínu v reakčnej zmesi 10 až 50 % hmot., v prostředí 1-metoxy-2-propanolu alebo jeho zmesi s vodou v hmotnostnom pomere 100:1 až 70:30, v přítomnosti kyseliny trihydrogénfosforečnej alebo kyseliny chlorovodíkovéj ako protonového katalýzátora v množstve 0,5 až 6,0 % hmot, vzhladom na použitý 2,6-dialkylanilín, pri teplote 20 až 100 °C(11) methoxypropanone in a solvent medium and in the presence of a proton catalyst and a platinum hydrogenation catalyst according to the invention, the essence of which is that the hydrogenation alkylation is carried out at a molar ratio of 2,6-dialkylaniline to methoxypropanone of 1: 1.1 to 2, concentration 2 Of 6-dialkylaniline in a reaction mixture of 10 to 50% by weight, in the medium of 1-methoxy-2-propanol or a mixture thereof with water in a weight ratio of 100: 1 to 70:30, in the presence of trihydrogenphosphoric acid or hydrochloric acid as proton catalyst in in an amount of 0.5 to 6.0% by weight, based on the 2,6-dialkylaniline used, at a temperature of 20 to 100 ° C
CS 266 996 Bl a tlaku vodíka 0,1 až 7,0 MPa. Prebytok metoxypropanónu vzhladom na použitý 2,6-dialkylanilin je potřebný na posunutie rovnovážného stavu reakoie v prospěch N-alkylácie 2,6-dialkylanilínu a vyžaduje si ho i tá skutečnost, že platinový hydrogenačný katalyzátor nie je úplné selektívny, takže vedla azometínu hydrogenuje čiastočne i metoxypropanón na l-metoxy-2-propanol. Hydrogenačná alkylácia na platinovom katalyzátore prebieha dostatečné rýchlo i v prostředí voda-metoxypropanol. Hydrogenovaf možno i v heterogénnej fáze, ked voda vo vstupujúcej reakčnej zmesi vzhladom na 2,6-dialkylanilín nie je viac ako 50 % hmotnostných a vzhladom na 1-metoxy-2-propanol nie viac ako 30 % hmotnostných. Zvyšovanie obsahu vody v reakčnej zmesi vedie však k čiastočnému zníženiu selektivity platinového hydrogenačného katalyzátora a k predlženiu reakčnej doby. Selektivitu hydrogenácie je možné usměrňovat i tlakom vodíka v reakčnej zmesi. So zvyšováním tlaku vodíka sa zvyšuje selektivita hydrogenácie, čo sa prejavuje tým, že relativné klesá množstvo metoxypropanónu zredukovaného na l-metoxy-2-propanol vzhladom na množstvo zredukovaného intermediárneho azometínu. Vodík sa do hydrogenačného autoklávu dávkuje na požadovaný tlak a počas reakcie indikovanej poklesem tlaku sa vodík dopíňa buč periodicky alebo sa v reakčnej nádobě udržiava konštantný tlak vodika pomocou redukčného ventila. Ukončenie reakcie je indikované zastavením poklesu tlaku. Reakciu je možné uskutečnit pri tlaku 0,1 až 7,0 MPa, s výhodou pri 3,0 až 5,5 MPa a teplote 20 až 100 °C, s výhodou pri 40 až 65 °C v násadovom alebo prietoČnom reaktore.CS 266 996 B1 and a hydrogen pressure of 0.1 to 7.0 MPa. An excess of methoxypropanone relative to the 2,6-dialkylaniline used is needed to shift the equilibrium state of the reaction in favor of N-alkylation of 2,6-dialkylaniline and is required by the fact that the platinum hydrogenation catalyst is not completely selective, so that azometine is partially hydrogenated. methoxypropanone to 1-methoxy-2-propanol. Hydrogenation alkylation on a platinum catalyst proceeds sufficiently rapidly even in a water-methoxypropanol environment. It is also possible to hydrogenate in the heterogeneous phase, when the water in the incoming reaction mixture is not more than 50% by weight relative to 2,6-dialkylaniline and not more than 30% by weight relative to 1-methoxy-2-propanol. However, increasing the water content of the reaction mixture leads to a partial decrease in the selectivity of the platinum hydrogenation catalyst and to a prolongation of the reaction time. The selectivity of the hydrogenation can also be controlled by the hydrogen pressure in the reaction mixture. As the hydrogen pressure increases, the selectivity of the hydrogenation increases, which is reflected in the relative decrease in the amount of methoxypropanone reduced to 1-methoxy-2-propanol relative to the amount of reduced azomethine intermediate. Hydrogen is metered into the hydrogenation autoclave to the desired pressure, and during the reaction indicated by the pressure drop, the hydrogen is charged either periodically or the hydrogen pressure in the reaction vessel is maintained at a constant pressure by means of a pressure reducing valve. Completion of the reaction is indicated by stopping the pressure drop. The reaction can be carried out at a pressure of 0.1 to 7.0 MPa, preferably at 3.0 to 5.5 MPa and a temperature of 20 to 100 ° C, preferably at 40 to 65 ° C in a batch or flow reactor.
Výhodou spdsobu přípravy 2,6-dialkyl-N-/l'-metoxy-2'-propyl/anilínov podlá vynálezu je, že kyselina trihydrogénfosforečná alebo kyselina chlorovodíková ako protonové katalyzátory velmi dobré katalyzujú tvorbu azometínu a udržujú vysokú aktivitu hydrogenačného katalyzátora na báze vzácných kovov, a že naviac, získaný reakčný produkt sa od nich z reakčnej zemsi lahko izoluje. Ďalšou výhodou spůsobu podlá vynálezu je, že l-metoxy-2-propanol, v prostředí ktorého sa hydrogenačná alkylácia uskutočňuje, velmi dobré rozpúšťa reakčné zložky, protonový katalyzátor, vodík, i reakčné produkty, mieša sa s vodou vo všetkých pomeroch, pričom s ňou vytvára azeotropní zmes a je i menej rizikový z hladiska zápalnosti. Z reakčnej zmesi ho možno lahko izolovat a opátovne použit v Salšom cykle.An advantage of the process for the preparation of 2,6-dialkyl-N- (1'-methoxy-2'-propyl) anilines according to the invention is that trihydrogenphosphoric acid or hydrochloric acid as proton catalysts catalyze the formation of azomethine very well and maintain the high activity of the hydrogenation catalyst based on rare acids. metals, and that, in addition, the obtained reaction product is easily isolated from them from the reaction ground. Another advantage of the process according to the invention is that 1-methoxy-2-propanol, in the medium in which the hydrogenation alkylation is carried out, dissolves the reactants, the proton catalyst, hydrogen and the reaction products very well, is mixed with water in all proportions and forms an azeotropic mixture and is also less risky in terms of flammability. It can be easily isolated from the reaction mixture and reused in the Salsch cycle.
Nasledujúce příklady ilustrujú, ale neobmedzujú predmet vynálezu.The following examples illustrate but do not limit the scope of the invention.
Příklad 1Example 1
Hydrogenačná alkylácia sa uskutečnila so zmesou 6,0 g (0,044 mólu) 2-metyl-6-etylanilínu, 4,7 g (0,053 mólu) metoxypropanónu, 16,4 g l-metoxy-2-propanolu, 18 mg platinového katalyzátora (nosič - aktivně uhlie) s obsahom 5 % kovu a 30 mg 85 %-nej kyseliny trihydrogénfosforečnej pri 20 °C a tlaku vodíka 5,0 MPa. Po 7,5 h sa absorpcia vodíka zastavila a reakcia sa přerušila. Analýzou metodou plynovej chromatografie sa zistilo, že anilínová fr.akcia reakčnej zmesi obsahu: 1,5 % nezreagovaného 2-metyl-6-etylanilínu a 97,3 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu.The hydrogenation alkylation was performed with a mixture of 6.0 g (0.044 mol) of 2-methyl-6-ethylaniline, 4.7 g (0.053 mol) of methoxypropanone, 16.4 g of 1-methoxy-2-propanol, 18 mg of platinum catalyst (support - activated carbon) containing 5% of metal and 30 mg of 85% trihydrogenphosphoric acid at 20 ° C and a hydrogen pressure of 5.0 MPa. After 7.5 h, the hydrogen uptake was stopped and the reaction was stopped. Analysis by gas chromatography showed that the aniline fraction of the reaction mixture contained: 1.5% unreacted 2-methyl-6-ethylaniline and 97.3% 2-methyl-6-ethyl-N- [1'-methoxy-2 propyl / aniline.
Příklad 2 .Example 2.
Hydrogenačná alkylácia sa uskutečnila so zmesou 6,0 g (0,044 mólu) 2-metyl-6-etylanilínu, 4,7 g (0,053 mólu) metoxypropanónu, 16,4 g l-metoxy-2-propanolu, 18 mg platinového katalyzátora (nosič - aktivně uhlie) s obsahom kovu 10 % a 140 mg 85 %-nej kyseliny trihydrogénfosforečnej pri 50 °C a tlaku vodíka 5,0 MPa. Po 2,5 h sa reakcia přerušila a analýzou metodou plynovej chromatografie sa zistilo, že anilínová frakcia reakčnej zmesi obsahuje: 0,4 % nezreagovaného 2-metyl-6-etylanilínu a 99,1 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu.The hydrogenation alkylation was performed with a mixture of 6.0 g (0.044 mol) of 2-methyl-6-ethylaniline, 4.7 g (0.053 mol) of methoxypropanone, 16.4 g of 1-methoxy-2-propanol, 18 mg of platinum catalyst (support - activated carbon) with a metal content of 10% and 140 mg of 85% trihydrogenphosphoric acid at 50 ° C and a hydrogen pressure of 5.0 MPa. After 2.5 h, the reaction was stopped and analyzed by gas chromatography that the aniline fraction of the reaction mixture contained: 0.4% unreacted 2-methyl-6-ethylaniline and 99.1% 2-methyl-6-ethyl-N- (1'-methoxy-2'-propyl) aniline.
Příklad 3Example 3
Hydrogenačná alkylácia sa uskutočnila so zmesou 6,0 g (0,044 mólu) 2-metyl-6-etylanilínu, 4,7 g (0,053 mólu) metoxypropanónu, 16,4 g 1-metoxy-2-propanelu, 18 mg platinového katalyzátora (nosič - aktivně uhlie) s obsahom kovu 10 % a 420 mg 85 %-nej kyseliny trihydrogénfosforečnej pri 50 °C a tlaku vodíka 5,0 MPa počas 2,5 h. Analýzou metodou plynovej chromatografieThe hydrogenation alkylation was performed with a mixture of 6.0 g (0.044 mol) of 2-methyl-6-ethylaniline, 4.7 g (0.053 mol) of methoxypropanone, 16.4 g of 1-methoxy-2-propanel, 18 mg of platinum catalyst (support - activated carbon) with a metal content of 10% and 420 mg of 85% trihydrogenphosphoric acid at 50 ° C and a hydrogen pressure of 5.0 MPa for 2.5 h. Analysis by gas chromatography
CS 266 996 Bl sa zlatilo, že v anilínovej frakcii reakčnej -zttesi sa nachádza len 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilín, bez přítomnosti 2-metyl-6-etylanilinu a azomeftinu.CS 266 996 B1 was found to contain only 2-methyl-6-ethyl-N- [1'-methoxy-2'-propyl] aniline in the aniline fraction of the reaction mixture, in the absence of 2-methyl-6-ethylaniline and azomeftin.
Příklad 4 .Example 4.
Hydrogenačná alkylácia sa uskutočnila so zmesou 6,0 g (0,044 molu) 2-metyl-6-etylanilinu, 4,7 g (0,053 molu) metoxypropanónu, 16,4 g l-metoxy-2-propanolu, 18 mg platinového katalyzátore (nosič - aktivně uhlie) s obsahem kovu 10 % a 60 mg kyseliny chlorovodíkovej nasýtenej v l-metoxy-2-propanole, pri 50 °C a tlaku vodíka 5,0 MPa, počas 4 h. Analýzou metodou plynovej chromatografie sa zistilo, že anilínová frakcia reakčnej zmesi obsahuje 2,5 % nezreagovaného 2-metyl-6-etylanilínu.The hydrogenation alkylation was performed with a mixture of 6.0 g (0.044 mol) of 2-methyl-6-ethylaniline, 4.7 g (0.053 mol) of methoxypropanone, 16.4 g of 1-methoxy-2-propanol, 18 mg of platinum catalyst (support - activated carbon) containing a metal content of 10% and 60 mg of hydrochloric acid saturated in 1-methoxy-2-propanol, at 50 ° C and a hydrogen pressure of 5.0 MPa, for 4 h. Analysis by gas chromatography showed that the aniline fraction of the reaction mixture contained 2.5% of unreacted 2-methyl-6-ethylaniline.
Příklad 5Example 5
Zmes 6,0 g 2-metyl-6-etylanilínu, 4,3 g metoxypropanónu, 12,7 g l-metoxy-2-propanolu, 0,21 g 85 %-nej kyseliny trihydrogénfosforečnej a 12 mg platinového katalyzátora (nosič - aktivně uhlie) s obsahom kovu 5 % sa hydrogenovala pri 55 °C a tlaku vodíka 4,5 MPa za intenzívneho miešania v autokláve počas 3,5 h. Analýzou metodou plynovej chromatografie sa zistilo, že anilínová frakcia reakčnej zmesi, obsahuje: 1,7 % ne z reagovaného 2-metyl-6-etylanilínu a 98,0 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu, bez obsahu azometínu.A mixture of 6.0 g of 2-methyl-6-ethylaniline, 4.3 g of methoxypropanone, 12.7 g of 1-methoxy-2-propanol, 0.21 g of 85% trihydrogenphosphoric acid and 12 mg of platinum catalyst (support - active coal) with a metal content of 5% was hydrogenated at 55 ° C and a hydrogen pressure of 4.5 MPa with vigorous stirring in an autoclave for 3.5 h. Analysis by gas chromatography showed that the aniline fraction of the reaction mixture contained: 1.7% of the reacted 2-methyl-6-ethylaniline and 98.0% of 2-methyl-6-ethyl-N- [1'-methoxy- 2'-propyl / aniline, azomethine-free.
Příklad 6Example 6
Zmes 6,0 g 2-metyl-6-etylanilínu, 4,7 g metoxypropanónu, 12,7 g l-metoxy-2-propanolu, 0,21 g 85 %-nej kyseliny trihydrogénfosforečnej a 12 mg platinového katalyzátora (nosič - aktivně uhlie) s obsahom kovu 5 % sa hydrogenovala pri 50 °C a tlaku vodíka 4,0 MPa za intenzívneho miešania v autokláve počas 3,5 h. Analýzou metodou plynovej chromatografie sa zistilo, že anilínová frakcia reakčnej zmesi obsahuje: 1,4 % nezreagovaného 2-metyl-6-etylanilínu a 98,3 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu, bez obsahu azometínu.A mixture of 6.0 g of 2-methyl-6-ethylaniline, 4.7 g of methoxypropanone, 12.7 g of 1-methoxy-2-propanol, 0.21 g of 85% trihydrogenphosphoric acid and 12 mg of platinum catalyst (support - active coal) with a metal content of 5% was hydrogenated at 50 ° C and a hydrogen pressure of 4.0 MPa with vigorous stirring in an autoclave for 3.5 h. Analysis by gas chromatography showed that the aniline fraction of the reaction mixture contained: 1.4% unreacted 2-methyl-6-ethylaniline and 98.3% 2-methyl-6-ethyl-N- [1'-methoxy-2'- propyl / aniline, azomethine-free.
Příklad 7Example 7
Zmes 6,0 g 2-metyl-6-etylanilínu, 5,3 g metoxypropanónu, 12,9 g l-metoxy-2-propanolu, 0,21 g 85 %-nej kyseliny trihydrogénfosforečnej a 12 mg platinového katalyzátora (nosič - aktivně uhlie) s obsahom kovu 5 % sa hydrogenovala v autokláve pri 55 °C a tlaku vodíka 7,0 MPa za intenzívneho miešania počas 3,5 h. Analýzou metodou plynovej chromatografie sa zistilo, že anilínová frakcia reakčnej zmesi obsahuje: 0,5 % nezreagovaného 2-metyl-6-etylanilínu a 99,1 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu, bez obsahu azometínu.A mixture of 6.0 g of 2-methyl-6-ethylaniline, 5.3 g of methoxypropanone, 12.9 g of 1-methoxy-2-propanol, 0.21 g of 85% trihydrogenphosphoric acid and 12 mg of platinum catalyst (support - active coal) with a metal content of 5% was hydrogenated in an autoclave at 55 ° C and a hydrogen pressure of 7.0 MPa with vigorous stirring for 3.5 h. Analysis by gas chromatography showed that the aniline fraction of the reaction mixture contained: 0.5% unreacted 2-methyl-6-ethylaniline and 99.1% 2-methyl-6-ethyl-N- [1'-methoxy-2'- propyl / aniline, azomethine-free.
Příklad 8Example 8
Zmes 6,0 g 2-metyl-6-etylanilínu, 5,17 g metoxypropanónu, 14,0 g l-metoxy-2-propanolu, 0,21 až 85 %-nej kyseliny trihydrogénfosforečnej a 120 mg platinového katalyzátora (nosič - aktivně uhlie) s obsahom kovu 5 % sa hydrogenovala v autokláve pri 50 °C a tlaku vodíka 0,1 MPa za intenzívneho miešania počas 6,5 h. Analýzou plynovou chromatografiou sa zistilo, že anilínová frakcia reakčnej zmesi obsahuje: 0,2 % nezreagovaného 2-metyl-6-etylanilínu a 99,4 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu, bez obsahu azometínu.A mixture of 6.0 g of 2-methyl-6-ethylaniline, 5.17 g of methoxypropanone, 14.0 g of 1-methoxy-2-propanol, 0.21 to 85% of trihydrogenphosphoric acid and 120 mg of platinum catalyst (support - active coal) with a metal content of 5% was hydrogenated in an autoclave at 50 ° C and a hydrogen pressure of 0.1 MPa with vigorous stirring for 6.5 h. Analysis by gas chromatography showed that the aniline fraction of the reaction mixture contained: 0.2% unreacted 2-methyl-6-ethylaniline and 99.4% 2-methyl-6-ethyl-N- [1'-methoxy-2'-propyl / aniline, azomethine - free.
Příklad 9Example 9
Zmes 6,0 g 2-metyl-6-etylanilínu, 7,8 g metoxypropanónu, 13,6 g l-metoxy-2-propanolu, 0,21 g kyseliny trihydrogénfosforečnej a 12 mg platinového katalyzátora (nosič - aktivně uhlie) s obsahom kovu 5 % sa hydrogenovala v autokláve pri 50 °C a tlaku vodíka 3,0 MPa za intenzívneho miešania počas 3,5 h. Analýzou metodou plynovej chromatografie sa zistilo, že anilínová frakcia reakčnej zmesi obsahuje: stopy nezreagovaného 2-metyl-6-etylanilínu, 99,8 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu, bez obsahu azometínu.A mixture of 6.0 g of 2-methyl-6-ethylaniline, 7.8 g of methoxypropanone, 13.6 g of 1-methoxy-2-propanol, 0.21 g of trihydrogenphosphoric acid and 12 mg of platinum catalyst (support - activated carbon) containing of metal 5% was hydrogenated in an autoclave at 50 ° C and a hydrogen pressure of 3.0 MPa with vigorous stirring for 3.5 h. Analysis by gas chromatography showed that the aniline fraction of the reaction mixture contained: traces of unreacted 2-methyl-6-ethylaniline, 99.8% of 2-methyl-6-ethyl-N- [1'-methoxy-2'-propyl] aniline , without azomethine content.
CS 266 996 Bl 5CS 266 996 Bl 5
Příklad 10Example 10
Zmes 6,0 g 2-metyl-6-etylanilínu, 4,7 g metoxypropanónu, 40 g, l-metoxy-2-propanolu, 0,21 g 85 %-nej kyseliny trihydrogénfosforečnej a 90 mg platinového katalyzátore (nosič - aktivně uhlie) s obsahom kovu 1 % sa hydrogenovala v autokláve pri 50 °C a tlaku vodíka, 4,0 MPa za intenzívneho miešania počas 3 h. Analýzou metodou plynovej chromatografie sa zistilo, že anilínová frakcia reakčnej zmesi obsahuje: 0,8 % nezreagovaného 2-metyl-6-etylanilínu a 99,0 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu, bez obsahu azometínu.A mixture of 6.0 g of 2-methyl-6-ethylaniline, 4.7 g of methoxypropanone, 40 g of 1-methoxy-2-propanol, 0.21 g of 85% trihydrogenphosphoric acid and 90 mg of platinum catalyst (supported carbon) ) with a metal content of 1% was hydrogenated in an autoclave at 50 ° C and a hydrogen pressure of 4.0 MPa with vigorous stirring for 3 h. Analysis by gas chromatography showed that the aniline fraction of the reaction mixture contained: 0.8% unreacted 2-methyl-6-ethylaniline and 99.0% 2-methyl-6-ethyl-N- [1'-methoxy-2'- propyl / aniline, azomethine-free.
Příklad 11Example 11
Zmes 30,0 g 2-metyl-6-etylanilínu, 23,2 g metoxypropanónu, 6,0 g l-metoxy-2-propanolu, 0,63 g 85 %-nej kyseliny trihydrogénfosforečnej a 50 mg platinového katalyzátora (nosič - aktivně uhlie) s obsahom kovu 10 % sa hydrogenovala v autokláve za intenzívneho miešenia pri 100 °C a tlaku vodíka 5,0 MPa počas 5 h. Analýzou metodou plynovej chromatografie sa zistilo, že anilínová frakcia rakčnej zmesi obsahuje: 3,2 % nezreagovaného 2-metyl-6-etylanilínu, 0,5 % azometínu a 94,6 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu.A mixture of 30.0 g of 2-methyl-6-ethylaniline, 23.2 g of methoxypropanone, 6.0 g of 1-methoxy-2-propanol, 0.63 g of 85% trihydrogenphosphoric acid and 50 mg of platinum catalyst (support - active carbon) with a metal content of 10% was hydrogenated in an autoclave with vigorous stirring at 100 ° C and a hydrogen pressure of 5.0 MPa for 5 h. Analysis by gas chromatography showed that the aniline fraction of the reaction mixture contained: 3.2% unreacted 2-methyl-6-ethylaniline, 0.5% azomethine and 94.6% 2-methyl-6-ethyl-N- [1 ' -methoxy-2'-propyl / aniline.
Příklad 12 'Example 12 '
Zmes 6,0 g 2-metyl-6-etylanilínu, 4,7 g metoxypropanónu, 14,8 g l-metoxy-2-propanolu, 0,8 g vody, 0,21 g 85 %-nej kyseliny trihydrogénfosforečnej a 18,0 mg platinového katalyzátora (nosič - aktivně uhlie) s obsahom kovu 5 % sa hydrogenovala v autokláve za intenzívneho miešania pri 45 °C a tlaku vodíka 5,0 MPa počas 4 h. Analýzou metodou plynovej chromatografie sa zistilo, že anilínová frakcia reakčnej zmesi obsahuje: 0,3 % nezreagovaného 2-metyl-6-etylanilínu a 99,3 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu, bez obsahu azometínu.A mixture of 6.0 g of 2-methyl-6-ethylaniline, 4.7 g of methoxypropanone, 14.8 g of 1-methoxy-2-propanol, 0.8 g of water, 0.21 g of 85% trihydrogenphosphoric acid and 18 g of 0 mg of platinum catalyst (support - activated carbon) with a metal content of 5% was hydrogenated in an autoclave with vigorous stirring at 45 ° C and a hydrogen pressure of 5.0 MPa for 4 h. Analysis by gas chromatography showed that the aniline fraction of the reaction mixture contained: 0.3% unreacted 2-methyl-6-ethylaniline and 99.3% 2-methyl-6-ethyl-N- [1'-methoxy-2'- propyl / aniline, azomethine-free.
Příklad 13Example 13
Zmes 6,0 g 2-metyl-6-etylanilínu, 4,7 g metoxypropanónu, 7,0 g l-metoxy-2-propanolu, 3,0 g vody, 0,21 g 85 %-nej kyseliny trihydrogénfosforečnej a 180 mg platinového katalyzátora (nosič - aktivně uhlie) s obsahom kovu 1 % sa hydrogenovala v autokláve za intenzívneho miešania pri 65 °C a tlaku vodíka 5,0 MPa počas 3,5 h. Analýzou metodou plynovej chromatografie sa zistilo, že anilínová frakcia reakčnej zmesi obsahuje: 0,4 % nezreagovaného 2-metyl-6-etylanilínu a 98,9 % 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu, bez obsahu azometínu.A mixture of 6.0 g of 2-methyl-6-ethylaniline, 4.7 g of methoxypropanone, 7.0 g of 1-methoxy-2-propanol, 3.0 g of water, 0.21 g of 85% trihydrogenphosphoric acid and 180 mg of a platinum catalyst (support - activated carbon) with a metal content of 1% was hydrogenated in an autoclave with vigorous stirring at 65 ° C and a hydrogen pressure of 5.0 MPa for 3.5 h. Analysis by gas chromatography showed that the aniline fraction of the reaction mixture contained: 0.4% unreacted 2-methyl-6-ethylaniline and 98.9% 2-methyl-6-ethyl-N- [1'-methoxy-2'- propyl / aniline, azomethine-free.
Příklad 14Example 14
Hydrogenačná alkylácia sa uskutočnila so zmesou 145,4 g (1,2 molu) 2,6-dialkylanilínu, 217,3 g (1,4 molu) metoxypropanónu vo forme 58,57 %-ného roztoku v l-metoxy-2-propanole, 240 g l-metoxy-2-propanolu, 1,54 g platinového katalyzátora (nosič - aktivně uhlie) s obsahom kovu 5 % a 3,8 g kyseliny trihydrogénfosforečnej pri 50 °C a tlaku vodíka 4,0 MPa počas 7 h. Získalo sa 222,4 g 2,6-dialkyl-N-/l'-metoxy-2'-propyl/anilínu o čistotě 98,4 %, čo odpovedá výtažku 94,1 %. T. v. produktu pri tlaku 1,3 kPa: 125 až 127 °C.The hydrogenation alkylation was performed with a mixture of 145.4 g (1.2 mol) of 2,6-dialkylaniline, 217.3 g (1.4 mol) of methoxypropanone as a 58.57% solution in 1-methoxy-2-propanol. , 240 g of 1-methoxy-2-propanol, 1.54 g of a platinum catalyst (support - activated carbon) with a metal content of 5% and 3.8 g of trihydrogenphosphoric acid at 50 ° C and a hydrogen pressure of 4.0 MPa for 7 h. 222.4 g of 2,6-dialkyl-N- [1'-methoxy-2'-propyl] aniline were obtained with a purity of 98.4%, corresponding to a yield of 94.1%. T. v. of product at a pressure of 1.3 kPa: 125 to 127 ° C.
Příklad 15Example 15
Hydrogenačná alkylácia sa uskutočnila so zmesou 179,1 g 2,6-dialkylanilínu (1,2 molu), 217,3 (1,4 molu) metoxypropanónu vo forme 58,57 %-ného roztoku v l-metoxy-2-propanole, 240 g l-metoxy-2-propanolu, 1,54 g platinového katalyzátora (nosič - aktivně uhlie) s obsahom kovu 5 % a 3,8 g kyseliny trihydrogénfosforečnej pri 60 °C a tlaku vodíka 4,0 MPa počas 7 h. Získalo sa 244,1 g 2,6-dietyl-N-/1'-metoxy-2'-propyl/anilínu (t. v. pri tlaku 1,3 kPa: 138 až 142 °C) o čistotě 97,7 %, čo odpovedá výtažku 86,84 %.The hydrogenation alkylation was performed with a mixture of 179.1 g of 2,6-dialkylaniline (1.2 mol), 217.3 g (1.4 mol) of methoxypropanone as a 58.57% solution in 1-methoxy-2-propanol. 240 g of 1-methoxy-2-propanol, 1.54 g of platinum catalyst (support - activated carbon) with a metal content of 5% and 3.8 g of trihydrogenphosphoric acid at 60 ° C and a hydrogen pressure of 4.0 MPa for 7 h. 244.1 g of 2,6-diethyl-N- [1'-methoxy-2'-propyl] aniline (m.p. at 1.3 kPa: 138-142 DEG C.) with a purity of 97.7% are obtained, corresponding to yield 86.84%.
CS 266 996 BlCS 266 996 Bl
Příklad 16Example 16
Hydrogenačná alkylácia sa uskutečnila .so zmesou 6,0 g (0,044 molu) 2-metyl-6-etylanilínu, 4,7 g (0,053 molu) metoxypropanónu, 16,4 g l-metoxy-2-propanolu, 18 mg platinového katalyzátora (nosič - aktivně uhlie) s obsahom kovu 5 % a 0,36 g kyseliny chlorovodíkovéj vopred rozpustenej v l-metoxy-2-propanole, pri 65 °C a tlaku vodíka 4,0 MPa počas 6 h. Analýzou metodou plynovej chromatografie sa zistilo, že anilínová frakcia reakčnej zmesi obsahuje 0,5 % nezreagovaného 2-metyl-6-etylanilínu.The hydrogenation alkylation was carried out with a mixture of 6.0 g (0.044 mol) of 2-methyl-6-ethylaniline, 4.7 g (0.053 mol) of methoxypropanone, 16.4 g of 1-methoxy-2-propanol, 18 mg of platinum catalyst ( support - activated carbon) with a metal content of 5% and 0.36 g of hydrochloric acid previously dissolved in 1-methoxy-2-propanol, at 65 ° C and a hydrogen pressure of 4.0 MPa for 6 h. Analysis by gas chromatography showed that the aniline fraction of the reaction mixture contained 0.5% of unreacted 2-methyl-6-ethylaniline.
Příklad 17Example 17
Hydrogenačná alkylácia sa uskutočnila so zmesou 6,0 g (0,044 molu) 2-metyl-6-etylanilínu, 4,7 g (0,053 mólu) metoxypropanónu, 16,4 g l-metoxy-2-propanolu, 36 mg platinového katalyzátore (nosič - aktivně uhlie) s obsahom kovu 5 % a 0,18 g kyseliny chlórovodíkovej vopred rozpustenej v l-metoxy-2-propanole, pri 45 °C a tlaku vodíka 7,0 MPa počas 6 h. Analýzou metodou plynovej chromatografie sa zistilo, že anilinová frakcia reakčnej zmesi obsahuje 0,4 % nezreagovaného l-metoxy-2-propanolu.The hydrogenation alkylation was performed with a mixture of 6.0 g (0.044 mol) of 2-methyl-6-ethylaniline, 4.7 g (0.053 mol) of methoxypropanone, 16.4 g of 1-methoxy-2-propanol, 36 mg of platinum catalyst (support - activated carbon) with a metal content of 5% and 0.18 g of hydrochloric acid previously dissolved in 1-methoxy-2-propanol, at 45 ° C and a hydrogen pressure of 7.0 MPa for 6 h. Analysis by gas chromatography showed that the aniline fraction of the reaction mixture contained 0.4% of unreacted 1-methoxy-2-propanol.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS884268A CS266996B1 (en) | 1988-06-20 | 1988-06-20 | Method of 2,6-dialkyl-n-(-methoxy-2-propyl)aniline preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS884268A CS266996B1 (en) | 1988-06-20 | 1988-06-20 | Method of 2,6-dialkyl-n-(-methoxy-2-propyl)aniline preparation |
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| Publication Number | Publication Date |
|---|---|
| CS426888A1 CS426888A1 (en) | 1989-05-12 |
| CS266996B1 true CS266996B1 (en) | 1990-01-12 |
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| Application Number | Title | Priority Date | Filing Date |
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| CS884268A CS266996B1 (en) | 1988-06-20 | 1988-06-20 | Method of 2,6-dialkyl-n-(-methoxy-2-propyl)aniline preparation |
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| Country | Link |
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| CS (1) | CS266996B1 (en) |
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1988
- 1988-06-20 CS CS884268A patent/CS266996B1/en unknown
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| Publication number | Publication date |
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| CS426888A1 (en) | 1989-05-12 |
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