SU355181A1 - METHOD OF OBTAINING DIAMIDOTHIOLOPHOSPHATES - Google Patents
METHOD OF OBTAINING DIAMIDOTHIOLOPHOSPHATESInfo
- Publication number
- SU355181A1 SU355181A1 SU1432858A SU1432858A SU355181A1 SU 355181 A1 SU355181 A1 SU 355181A1 SU 1432858 A SU1432858 A SU 1432858A SU 1432858 A SU1432858 A SU 1432858A SU 355181 A1 SU355181 A1 SU 355181A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- diamidothiolophosphates
- obtaining
- diamidothiol
- phosphates
- triethylamine
- Prior art date
Links
- 235000021317 phosphate Nutrition 0.000 description 10
- 238000000034 method Methods 0.000 description 5
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 5
- -1 phosphorus ester amides Chemical class 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-Bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- HQGBWUXEXCCXBU-UHFFFAOYSA-N BrO.CCN(CC)CC Chemical compound BrO.CCN(CC)CC HQGBWUXEXCCXBU-UHFFFAOYSA-N 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N Bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- 230000036826 Excretion Effects 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FKNYTRBBGNUNOX-UHFFFAOYSA-N N,N-diethyl-2-(4-methylphenoxy)ethanamine Chemical compound CCN(CC)CCOC1=CC=C(C)C=C1 FKNYTRBBGNUNOX-UHFFFAOYSA-N 0.000 description 1
- NRTLTGGGUQIRRT-UHFFFAOYSA-M N,N-diethylethanamine;bromide Chemical compound [Br-].CCN(CC)CC NRTLTGGGUQIRRT-UHFFFAOYSA-M 0.000 description 1
- LVUFERQPPYHGHL-UHFFFAOYSA-N N-[dimethylamino(hydroxy)phosphinothioyl]-N-methylmethanamine Chemical compound CN(C)P(O)(=S)N(C)C LVUFERQPPYHGHL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 230000000855 fungicidal Effects 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
Description
Изобретение относитс к получению эфироамидов кислот фосфора, а именно к способу получени диамидотиолофосфатов.The invention relates to the preparation of phosphorus ester amides, and specifically to a process for preparing diamidothiol phosphates.
Среди диамидотиолофосфатов найдены эффективные пестициды, в частности диамидобензилтиолофосфаты , обладающие фунгицидной активностью.Among the diamidothiol phosphates, effective pesticides have been found, in particular diamidobenzyl thiol phosphates, which have fungicidal activity.
Известен способ получени диамидотиолофосфатов взаимодействием диамидохлорфосфатов с меркаптанами в присутствии акцептора хлористого водорода.A known method of producing diamidothiol phosphates by the interaction of diamidochlorophosphates with mercaptans in the presence of a hydrogen chloride acceptor.
Основным недостатком известного способа вл етс труднодоступность исходных диамидохлорфосфатов , так как при их получении всегда образуетс плохо раздел ема смесь моно- и диамидохлорфосфатов.The main disadvantage of this method is the inaccessibility of the initial diamidochlorophosphates, since when they are obtained, a poorly separable mixture of mono- and diamidochlorophosphates is always formed.
С целью упрощени процесса предложено диамидотиолофосфаты получать при взаимодействии солей, например аммонийных, диамидотиолофосфорных кислот с галоидалкилами .In order to simplify the process, it has been proposed to obtain diamidothiol phosphates by reacting salts, for example ammonium, diamidothiol phosphoric acids with haloalkyls.
Процесс провод т при комнатной или при несколько более высокой температуре. Целевые продукты выдел ют известными приемами . Выход До 43%.The process is carried out at room temperature or at a slightly higher temperature. Target products are recovered by known techniques. Yield Up to 43%.
Пример 1. Тетраэтилдиамидоэтилтиолофосфат .Example 1. Tetraethyl diamidoethylthiol phosphate.
50°С, отфильтровывают бромгидрат триэтиламина и разгон ют фильтрат. Т. кип. целевого продукта 102-104°С/1 мм; «о 1,4900;50 ° C, triethylamine bromide is filtered off and the filtrate is dispersed. T. Kip. target product 102-104 ° C / 1 mm; “About 1.4900;
° 1,0219. Выход И г (41%).° 1.0219. Output And g (41%).
Найдено, %: С 47,86; Н 10,02; Р 12,59; МНв71,4.Found,%: C 47.86; H 10.02; P 12.59; MNv71,4.
Вычислено, %: С 47,59; Н 9,98; Р 12,27; MRD 70,7.Calculated,%: C 47.59; H 9.98; R 12.27; MRD 70.7.
Пример 2. Тетраметилдиамидоэтилтиолофосфат .Example 2. Tetramethyldiamidoethylthiol phosphate.
К 70 г соли триэтиламипа и тетраметилдиамидотиофосфорной кислоты добавл ют 28 гTo 70 g of salt of triethylamine and tetramethyldiamidothiophosphoric acid are added 28 g
бромистого этила и провод т реакцию приethyl bromide and carried out the reaction at
комнатной температуре. По мере добавлени room temperature. As you add
бромистого этила наблюдаетс выделениеethyl bromide excretion is observed
бромгидрата триэтиламина. После смешени triethylamine bromohydrate. After mixing
реагентов смесь перемешивают 30 мин, отфильтровывают осадок и разгон ют фильтрат.The reagents are stirred for 30 minutes, the precipitate is filtered off and the filtrate is dispersed.
Получают 19 г (37%) целевого продукта,Obtain 19 g (37%) of the desired product,
т. кип. 72-73°С/1 мм; 1,5064; 1,0810.m.p. 72-73 ° C / 1 mm; 1.5064; 1.0810.
Пайдено, %: N 14,45; Р 15,43; S 16,59;Paydeno,%: N 14.45; R 15.43; S 16.59;
MRD 53,9.MRD 53.9.
Вычислено, %: N 14,28; Р 15,78; S 16,33; MRD 52,3.Calculated,%: N 14.28; R 15.78; S 16.33; MRD 52.3.
Пример 3. Тетраметилдиамидобутилтиолофосфат . 3 28 г бромистого бутила, перемешивают 1,5 час при 50-60°С, отфильтровывают бромгидрат триэтиламина и фильтрат разгон ют. Получают 13 г (30%) целевого продукта. т. кип. 93-94°С/1 мм; По 1,4973; d° 1,0423.5 Найдено, %: С 42,65; Н 9,58; Р 13,71; MRo 63,0. Вычислено, %: С 42,83; Н 9,43; Р 13,80; MRD 61,5. Пример 4. Тетраэтилдиамидобутилтиолофосфат . К 40 2 триэтиламина и тетраэтилдиамидотиофосфорной кислоты добавл ют 28 г бромистого бутила, перемешивают 50 мин при15 50-60°С, отдел ют бромгидрат трнэтиламина 10 4 и после разгонки фильтрата выдел ют 14,8 г ( 43%) фракции с т. кип. 140-145°С/1 лш; д 1,5080; 1,0648. Найдено, %: С 51,60; Н 10,13; Р 11,32; MRn 78,5. Вычислено,%: С 51,39; Н 10,42; Р 11,04; MRo 79,9. „ Предмет изобретени Способ получени диамидотиолофосфатов на основе амидов кислот фосфора, отличающийс тем, что, с целью упрощени процесса, соли диамидотиофосфорных кислот подвергают взаимодействию с галоидалкилами.Example 3. Tetramethyldiamidobutylthiol phosphate. 3 28 g of butyl bromide, stirred for 1.5 hours at 50-60 ° C, triethylamine bromohydrate was filtered off and the filtrate was dispersed. Obtain 13 g (30%) of the desired product. m.p. 93-94 ° C / 1 mm; 1.4973 each; d ° 1,0423.5 Found: C 42.65; H 9.58; P 13.71; MRo 63.0. Calculated,%: C 42.83; H 9.43; P 13.80; MRD 61.5. Example 4. Tetraethyl diamidobutyl thiol phosphate. To 40 2 triethylamine and tetraethyldiamidothiophosphoric acid, 28 g of butyl bromide are added, stirred for 15 min at 15–50–60 ° C, trinethylamine hydrobromide is separated, and after distillation of the filtrate, 14.8 g (43%) of the fraction with bp is separated. 140-145 ° C / 1 lsh; d 1.5080; 1.0648. Found,%: C 51.60; H 10.13; R 11.32; MRn 78.5. Calculated,%: C, 51.39; H 10.42; R 11.04; MRo 79.9. The subject of the invention is a process for the preparation of diamidothiol phosphates based on phosphorus acid amides, characterized in that, in order to simplify the process, salts of diamidothiophosphoric acids are reacted with haloalkyls.
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