CS266776B1 - Low-frequency signal's gross harmonic distortion's meter and generator set connection - Google Patents
Low-frequency signal's gross harmonic distortion's meter and generator set connection Download PDFInfo
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Abstract
Očelom riešenia je spdsob přípravy 6-nitro-2-benzotiazolinónu vzorca I oxidáciou 6-nitro-2-benzotiazolíntiónu manganistanom draselným v přítomnosti alkalického hydroxidu a následným rozkladom vzniknutého medziproduktu v kyslom prostředí. Zlúčenina sa dá používat ako reaktívny medziprodukt pre syntézu regulátorov rastu rastlin, fungicídov a dalších látok.The aim of the solution is the way of preparation 6-nitro-2-benzothiazolinone of formula I by oxidation 6-nitro-2-benzothiazolinothione potassium permanganate in the presence alkali hydroxide followed by decomposition of the resulting intermediate in an acidic environment. The compound can be used as reactive intermediate for growth regulator synthesis plants, fungicides and other substances.
Description
Predmetom vynálezu je spósob přípravy 6-nitro-2-benzotiazolinónu vzorca I /1/The present invention relates to a process for the preparation of 6-nitro-2-benzothiazolinone of formula I (1).
Uvedená zlúčenina bola připravená nitráciou 2-benzotiazolinónu (Fridman, S. G., Ž. obšč. chim. 24, 642 (1954)) s 54 %-ným výťažkom. Ďalším známým spósobom přípravy je hydrolýza sulfónov v kyslom (výťažok 92 %) alebo alkalickom (výťažok 91 %) prostředí (I. Ya. Postovskij, I. A. Alexejeva, Ž. obšč. chim. 23, 1 905 (1953)).The title compound was prepared by nitration of 2-benzothiazolinone (Fridman, S. G., W. Ch. 24, 642 (1954)) in 54% yield. Another known method of preparation is the hydrolysis of sulfones in an acidic (92% yield) or alkaline (91% yield) medium (I. Ya. Postovsky, I. A. Alexeyeva, Ž.
Teraz bol zistený doteraz nepopísaný spósob přípravy uvedenej zlúčeniny, ktorý sa vyznačuje tým, že sa nechá reagovat 6-nitro-2-benzotiazolíntión s manganistanem draselným v alkalickom prostředí.A hitherto undescribed process for the preparation of said compound has now been found, which is characterized in that 6-nitro-2-benzothiazolinethione is reacted with potassium permanganate in an alkaline medium.
Zistený nový spósob přípravy 6-nitro-2-benzotiazolinónu má tú výhodu oproti opísaným, že vychádza zo 6-nitro-2-benzotiazolíntiónu, ktorý je lahko dostupný nitráciou technického, v ČSSR vyrábaného 2-benzotiazolíntiónu, známého gumárenského urýchlovača. Kým příprava 2-benzotiazolinónu, z ktorého sa 6-nitro-2-benzotiazolinón vyrába nitráciou, je časové a energeticky náročná vo fáze rozkladu 2-benzotiazolsulfónanu draselného, zatial u analogického 6-nitro-2-benzotiazolsulfónanu draselného prebieha prakticky už hned po okyselení pri teplote miestnosti, čo znamená úsporu času aj energie.The new process for the preparation of 6-nitro-2-benzothiazolinone found has the advantage over that described, starting from 6-nitro-2-benzothiazolinethione, which is readily available by nitration of the technical rubber accelerator known in the Czechoslovak Republic. While the preparation of 2-benzothiazolinone, from which 6-nitro-2-benzothiazolinone is produced by nitration, is time-consuming and energy-intensive in the decomposition phase of potassium 2-benzothiazol sulphonate, while the analogous potassium 6-nitro-2-benzothiazol sulphonate takes place almost immediately after acidification at room temperature, which saves time and energy.
Reakciu možno uskutočniť diskontinuálnym spósobom v univerzálněj aparatúre, nevyžaduje stavbu jednoúčelovéj aparatúry.The reaction can be carried out in a batchwise manner in a universal apparatus, it does not require the construction of a single-purpose apparatus.
Vynález je využitelný pre výhodnú přípravu 6-nitro-2-benzotiazolinónu, reaktívneho medziproduktu pre syntézu fungicídov (Idemitsu Kosan Co Ltd., Jap. pat. 60 105 604 (1985)), regulátorov rastu rastlín (D'Amico J. J., US pat. 4 282 029 (1981) a iné), ako aj pre dalšie syntézy zlúčenín s předpokládanou biologickou aktivitou.The invention is useful for the preferred preparation of 6-nitro-2-benzothiazolinone, a reactive intermediate for the synthesis of fungicides (Idemitsu Kosan Co Ltd., Japan Pat. No. 60,105,604 (1985)), plant growth regulators (D'Amico JJ, U.S. Pat. 4,282,029 (1981) and others), as well as for other syntheses of compounds with putative biological activity.
Nasledujúce příklady bližšie osvetlujú, ale nijako neobmedzujú spósob přípravy 6-nitro-2-benzotiazolinónu zo 6-nitro_2-benzotiazolíntiónu oxidáciou s následnou hydrolýzou.The following examples illustrate, but do not limit, the process for preparing 6-nitro-2-benzothiazolinone from 6-nitro-2-benzothiazolinethione by oxidation followed by hydrolysis.
Příklad 1Example 1
Příprava 6-nitro-2-benzotiazolinónu, postup APreparation of 6-nitro-2-benzothiazolinone, procedure A
6-nitro-2-benzotiai.olíntión (25,4 g, 0,12 mol) sa rozpustil v roztoku hydroxidu draselnéo ho (18 g, 0,32 mol) vo vodě (300 cm ). Zmes sa zahriala do vyčírenia, potom sa k nej po malých dávkách přidával roztok manganistanu draselného (40 g, 0,25 mol) rozpuštěný vo vodě (800 cm3) za tepla. Po přidaní celého množstva manganistanu sa roztok zahrial do varu, odsál sa kysličník maganičitý a premyl sa vodou, kým odtékala sfarbená premývacia voda. Všetky tekuté podřely sa spojili a odfarbili sa aktívnym uhlím. Roztok sa okyslil kyselinou sírovou zriedenou vodou v pomere 1:1 na pH 3 a na 15 minút sa zahrial do varu. Ihned po okyslení začínal vypadávat surový 6-nitro-2-benzotiazolinón s teplotou topenia 247 až 252 C. Výťažok činil 65,6 g (93,0 %). Vzorka pre analýzu bola přečištěná tým spósobom, že sa rozpustila v zmesi acetón-etanol-voda v pomere 1:1:1 a po odfarbení aktívnym uhlím sa z něho vyzrážala vodou.6-Nitro-2-benzothiazolinolethione (25.4 g, 0.12 mol) was dissolved in a solution of potassium hydroxide (18 g, 0.32 mol) in water (300 cm 3). The mixture was heated to clear, then a solution of potassium permanganate (40 g, 0.25 mol) dissolved in water (800 cm 3 ) while hot was added in small portions. After all the permanganate had been added, the solution was heated to boiling, the magnesium oxide was filtered off with suction and washed with water until the colored washing water drained off. All liquid wells were pooled and decolorized with activated charcoal. The solution was acidified to pH 3 with sulfuric acid diluted 1: 1 with water and heated to reflux for 15 minutes. Immediately after acidification, crude 6-nitro-2-benzothiazolinone with a melting point of 247-252 ° C began to precipitate. The yield was 65.6 g (93.0%). The sample for analysis was purified by dissolving it in a 1: 1: 1 mixture of acetone-ethanol-water and precipitating with water after decolorizing with activated carbon.
Získal sa čistý 6-nitro-2-benzotiazolinón s t. t. 250,5 až 252,5 °C. Literatúra udává t. t. 249 až 250 °C (Postovskij I. Ya., Alexejeva, I. A., Ž. obšč. chim. 23, 1 905 (1953)), 248 °C (Fridmen S. G. Ž. obšč. chim. 24, 642 (1954)) alebo 253 °C (Eichi Ochiai Kazumasa Kokeguchi, Masao Shimizu, Hiroshi Nishizawa, J. Pharm. Soc. Japan, 63, 258 (1943)).Pure 6-nitro-2-benzothiazolinone with m.p. t. 250.5 to 252.5 ° C. The literature states t. t. 249-250 ° C (Postovskij I. Ya., Alexejeva, IA, Ž. Obč. Chim. 23, 1 905 (1953)), 248 ° C (Fridmen SG Ž. or 253 ° C (Eichi Ochiai Kazumasa Kokeguchi, Masao Shimizu, Hiroshi Nishizawa, J. Pharm. Soc. Japan, 63, 258 (1943)).
Pre C7H4N2O3S (196,19)For C 7 H 4 N 2 O 3 S (196.19)
265776 vypočítané í: C 42,86 H 2,06 N 14,28 S 16,34 zistené: 42,57 1,89 14,23 16,19265776 calculated: C 42.86 H 2.06 N 14.28 S 16.34 found: 42.57 1.89 14.23 16.19
Příklad 2Example 2
Příprava 6-nitro-2-benzotiazolinónu, postup BPreparation of 6-nitro-2-benzothiazolinone, procedure B
Oxidácia 6-nitro-2-benzotiazolíntiónu bola vykonaná podlá příkladu 1. Po odsátí kysličníka manganičitého, premytí vodou a odfarbení aktívnym uhlím sa k filtrátu přidal hydroxylamóniumchlorid (35 g, 0,5 mol), pričom sa z roztoku ihned zrážal 6-nitro-2-benzotia^olinón. Výťažok surového produktu bol kvantitativný. ' . ·, \Oxidation of 6-nitro-2-benzothiazolinethione was performed according to Example 1. After aspiration of the manganese dioxide, washing with water and decolorization with activated charcoal, hydroxylammonium chloride (35 g, 0.5 mol) was added to the filtrate, 6-nitro- 2-benzothiazolinone. The yield of crude product was quantitative. '. ·, \
Vzorka pre analýzu bola přečištěná podlá příkladu 1. Získal sa čistý 6-nitro-2.-benzotiazolinón s t. t. 250 až. 253 °C, ktorý nedával depresiu t. t. s produktom podlá příkladu-1.A sample for analysis was purified according to Example 1. Pure 6-nitro-2-benzothiazolinone with m.p. t. 250 to. 253 ° C, which did not give depression t. t. with the product of Example-1.
Pre C7H4N2O3S (1Ό6,19) vypočítané %: C 42,86 H 2,06 N 14,28 S 16,34 zistené %: 42,67 1,85 14,06 16,54For C 7 H 4 N 2 O 3 S (1-6.19) calculated%: C 42.86 H 2.06 N 14.28 S 16.34 found%: 42.67 1.85 14.06 16.54
Zlúčenina podlá vynálezu sa používá ako reaktívny medziprodukt pře syntézu stímulátorov rastu rastlín (D'Amico J. J., US pat. 4 282 029 (1981) a iné) a fungicídov (Idemitsu Kosan Co. Ltd. Jap. pat. 60 105 604 (1985)) a pre dalšie syntézy.The compound of the invention is used as a reactive intermediate for the synthesis of plant growth stimulators (D'Amico JJ, U.S. Pat. No. 4,282,029 (1981) and others) and fungicides (Idemitsu Kosan Co. Ltd. Jap. Pat. No. 60,105,604 (1985) ) and for other syntheses.
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