CS254686B1 - Process for preparing raw 2-isopropylamino-4-ethylamino-6-chlor-s-triazine - Google Patents
Process for preparing raw 2-isopropylamino-4-ethylamino-6-chlor-s-triazine Download PDFInfo
- Publication number
- CS254686B1 CS254686B1 CS861809A CS180986A CS254686B1 CS 254686 B1 CS254686 B1 CS 254686B1 CS 861809 A CS861809 A CS 861809A CS 180986 A CS180986 A CS 180986A CS 254686 B1 CS254686 B1 CS 254686B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- atrazine
- reaction
- triazine
- aqueous
- isopropylamino
- Prior art date
Links
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 title abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 21
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims abstract description 16
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims abstract description 11
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000007864 aqueous solution Substances 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 239000011541 reaction mixture Substances 0.000 claims abstract description 5
- 239000004094 surface-active agent Substances 0.000 claims abstract description 5
- 239000012736 aqueous medium Substances 0.000 claims abstract description 4
- 239000012266 salt solution Substances 0.000 claims abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 10
- 239000013530 defoamer Substances 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 abstract description 8
- 239000002518 antifoaming agent Substances 0.000 abstract description 3
- 230000002363 herbicidal effect Effects 0.000 abstract description 3
- 239000004009 herbicide Substances 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 4
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 4
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- XUHRVZXFBWDCFB-QRTDKPMLSA-N (3R)-4-[[(3S,6S,9S,12R,15S,18R,21R,24R,27R,28R)-12-(3-amino-3-oxopropyl)-6-[(2S)-butan-2-yl]-3-(2-carboxyethyl)-18-(hydroxymethyl)-28-methyl-9,15,21,24-tetrakis(2-methylpropyl)-2,5,8,11,14,17,20,23,26-nonaoxo-1-oxa-4,7,10,13,16,19,22,25-octazacyclooctacos-27-yl]amino]-3-[[(2R)-2-[[(3S)-3-hydroxydecanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoic acid Chemical compound CCCCCCC[C@H](O)CC(=O)N[C@H](CC(C)C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H]1[C@@H](C)OC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CO)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC1=O)[C@@H](C)CC XUHRVZXFBWDCFB-QRTDKPMLSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 102000008068 Tensins Human genes 0.000 description 1
- 108010088950 Tensins Proteins 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- -1 polymethylsiloxane Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Rieši sa příprava atrazínu reakciou kya- nurchloridu s etylamínom, izopropylamínom a hydroxidom sodným. Reakcia prebieha vo vodnom prostředí alebo v prostředí vodného roztoku alkalického chloridu a v přítomnosti tenzidu. Po ukončení reakcie sa k reakčnej zmesi přidá odpeňovač a atrazín sa odfiltruje úd roztoku solí. Riešenie nájde uplatnenie pri výrobě atrazínu, ktorý sa používá ako herbicid v poínohospodárstveThe preparation of atrazine by reaction of cyanuric chloride with ethylamine, isopropylamine and sodium hydroxide is solved. The reaction is carried out in an aqueous medium or in an aqueous solution of alkaline chloride and in the presence of a surfactant. Upon completion of the reaction, an antifoam is added to the reaction mixture and the atrazine is filtered off from the salt solution. The solution will find application in the manufacture of atrazine, which is used as a herbicide in agriculture
Description
Vynález rieši sposob přípravy technického 2-izopropylamíno-4-ety]amíno-6-chlór-s-trlazínu reakciou kyanurchloridu s vodnými roztokmi etylamínu, izopropylamínu, hydroxidu sodného vo vodnom prostředí v přítomnosti tenzidu a po ukončení reakcie s prídavkom odpeňovača.The invention solves a process for the preparation of technical 2-isopropylamino-4-ethylamino-6-chloro-s-trlazine by reacting cyanuric chloride with aqueous solutions of ethylamine, isopropylamine, sodium hydroxide in aqueous medium in the presence of a surfactant and after completion of the reaction with the addition of a defoamer.
Medzi najznámejšie a najviac vyrábané s-triazínové herbicidy patří 2-izopropylamíno-4-etylamíno-6-chlór-s-triazín (atrazín). Herbicídne účinky boli objavené v roku 1954 vo Švajčiarsku a sú popísané vo švajčiarskom patente 229 227. Příprava atrazínu reakciou kyanurchloridu, etylamínu, izopropylamínu a hydroxidu sodného vo vodnochlórbenzénovom prostředí je popísaná v československom patente 110 352. Príprav atrazínu reakciou kyanurchloridu a etylamínu, izopropylamínu v prostředí bezvodého organického rozpúšťadla, pričom sa viazanie vzniknutého chlorovodíka sa použije bez vodného amoniaku popisuje švajčiarsky patent 508 Θ40. Získaný produkt obsahuje 92 % atrazínu. Vplyv hodnoty pH na výťažok atrazínu popisujú patentové spisy NDR a NSR. Podlá NDR pat. 51 646 sa najlepší výťažok dosiahne vtedy, ak v prvom reakčnom stupni, t. j. po přidaní prvého aminu a hydroxidu alkalického kovu sa udržuje hodnota pH 6 — 8, v druhom reakčnom stupni, t. j. po přidaní druhého aminu a hydroxidu alkalického kovu sa udržuje hodnota pH na 8,5 — 9. Výťažok atrazínu je 96 %. V NSR patente číslo 2 032 861 sa udává hodnota pH v prvom stupni 6,5 — 10. V USA pat. 3 328 399 a 3 586 679 je popísaný sposob přípravy atrazínu z kyanurchloridu, etylamínu, izopropylamínu v bezvodnom prostředí pri teplote 120 až 170 stupňov Celzia za oddestilovania vzniknutého chlorovodíka. Výhoda spósobu je, že odpadne problém odpadných vód s obsahom minerálnych solí. V švajčiarskom patente číslo 546 247 sa popisuje adiabatický spósob výroby atrazínu vo vodonerozpustnom rozpúšťadle reakciou etylamínu, izopropylamínu, alkalického hydroxidu s kyanurchloridom.Among the best known and most widely produced s-triazine herbicides are 2-isopropylamino-4-ethylamino-6-chloro-s-triazine (atrazine). Herbicidal effects were discovered in Switzerland in 1954 and are described in Swiss Patent 229 227. Preparation of atrazine by reaction of cyanuric chloride, ethylamine, isopropylamine and sodium hydroxide in aqueous chlorobenzene is described in Czechoslovak patent 110,352. of an anhydrous organic solvent, the binding of the resulting hydrogen chloride being used without aqueous ammonia is described in Swiss Patent 508-40. The product obtained contained 92% atrazine. The effect of pH on atrazine yield is described in the patents NDR and NSR. According to the GDR Pat. 51,646, the best yield is obtained if, in the first reaction step, i.e., the reaction is carried out in the first step. j. after the addition of the first amine and the alkali metal hydroxide, the pH is maintained at 6-8, in the second reaction stage, i.e., the reaction is carried out at a pH of 6 to 8; j. after addition of the second amine and alkali metal hydroxide, the pH is maintained at 8.5-9. The atrazine yield is 96%. German Patent No. 2,032,861 discloses a pH of 6.5-10 in the first stage. U.S. Pat. Nos. 3,328,399 and 3,586,679 disclose a process for preparing atrazine from cyanuric chloride, ethylamine, isopropylamine in an anhydrous environment at a temperature of 120 to 170 degrees Celsius to distill off the resulting hydrogen chloride. The advantage of the method is that the problem of waste waters containing mineral salts is eliminated. Swiss Patent No. 546 247 describes an adiabatic process for producing atrazine in a water-insoluble solvent by reacting ethylamine, isopropylamine, alkali hydroxide with cyanuric chloride.
Vo francúzskom patente 2 296 628, rumunskom patente 68 016, japonskom patente č. 131 592 [1977] sa doporučuje pri dávkovaní amínov pri výrobě atrazínu dávkovat prvý izopropylamín. Banks C. a spol., J. Am. Chem. Soc. 66, 1771 (1944) a Friedheim E., J. Am. Chem. Soc. 66, 1723 (1944) doporučujú pri prvom reakčnom stupni výroby atrazínu teplotu okolo 0 °C a druhý reakčný stupeň pri teplotách 30 — 50 °C. Pri prvom reakčnom stupni sa ako reakčné prostredie používá zmes vody a ladu, připadne voda, lad a organické rozpúšťadlo.In French patent 2,296,628, Romanian patent 68,016, Japanese patent no. 131 592 [1977], it is recommended that the first isopropylamine be metered in at amine dosing for atrazine production. Banks C. et al., J. Am. Chem. Soc. 66, 1771 (1944) and Friedheim E., J. Am. Chem. Soc. 66, 1723 (1944) recommend a temperature of about 0 ° C for the first reaction stage of atrazine production and a second reaction stage for temperatures of 30-50 ° C. In the first reaction step, a mixture of water and ice is used as the reaction medium, optionally water, ice and an organic solvent.
Nevýhodou vyššie uvedených postupov je, že kondenzácia prebieha v přítomnosti organického rozpúšťadla, ktoré sa musí po ukončení kondenzácie od produktu oddělit.A disadvantage of the above processes is that the condensation takes place in the presence of an organic solvent which must be separated from the product after the condensation has been completed.
Na reakciu použitý kyanurchlorid ako i vzniknutý technický atrazín sú čiastočne hydrofóbne, čo móže sťažovať reakciu kyanurchloridu s roztokmi amínov, ako i znižovať reakčnú rychlost samotnej reakcie. Pri použití tenzidov pri oddělovaní technického atrazínu od vodného roztoku móže vznikat pěna, ktorá robí problémy pri odstreďovaní.The cyanuric chloride used for the reaction as well as the technical atrazine formed are partially hydrophobic, which may make it more difficult to react the cyanuric chloride with amine solutions as well as to reduce the reaction rate of the reaction itself. The use of surfactants to separate the technical atrazine from the aqueous solution may give rise to foam which causes problems during centrifugation.
Vyššie uvedené nedostatky sú zmiernené sposobom přípravy technického 2-izopropylamíno-4-etylamíno-6-chlór-s-triazínu, podstata ktorého spočívá v tom, že reaguje kyanurchlorid s vodnými roztokmi etylamínu, izopropylamínu a hydroxidu sodného' vo vodnom prostředí alebo v prostředí vodného roztoku alkalického' chloridu. Reakcia prebieha v přítomnosti tenzidu. Poi ukončení reakcie sa k reakčnej zmesi přidá odpeňovač a technický atrazín sa oddělí od roztoku solí.The above-mentioned drawbacks are alleviated by the process of preparing 2-isopropylamino-4-ethylamino-6-chloro-s-triazine by reacting cyanuric chloride with aqueous solutions of ethylamine, isopropylamine and sodium hydroxide in aqueous or aqueous media. of an alkaline chloride solution. The reaction is carried out in the presence of a surfactant. After completion of the reaction, an antifoam was added to the reaction mixture and the technical atrazine was separated from the salt solution.
Postupom přípravy technického atrazínu podlá vynálezu sa dosiahne pri použití tenzinu lepšie zmáčanie kyanurchloridu a vzniknutého atrazínu, čím sa zlepšia reakčné podmienky pri výrobě atrazínu.The process of preparation of technical atrazine according to the invention achieves better wetting of cyanuric chloride and the resulting atrazine using tensin, thereby improving the reaction conditions for atrazine production.
Přidáním odpeňovača k reakčnej zmesi po ukončení reakcie sa zlepší oddelovanie atrazínu od roztoku solí a pri cdstreďovaní sa zabráni tvorbě pěny, ktorá sposobuje tažkosti pri dopravě suspenzie atrazínu.By adding an antifoam to the reaction mixture after the reaction is complete, the separation of atrazine from the salt solution is improved, and centrifugation avoids the formation of a foam which causes difficulty in conveying the atrazine suspension.
Příklad 1Example 1
Do reakčnej banky sa dalo 250 ml vody. Po ochladení na 5’C sa k vodě dalo 30 g kyanurchloridu. K zmesi sa přidalo 0,1 ml kopolyméru etylénoxidu a propylénoxidu známého pod obchodným názvom Slovanik T 610. Potom sa postupné přidalo 50 ml 20,2 percent. hmot. vodného izopropylamínu a po 30 minútach 55 ml 10,0 % hmot. vodného roztoku hydroxidu sodného. Teplota sa udržiavala v rozmedzí 5 až 10 °C. Po 50 minútach sa k reakčnej zmesi přidalo 21,5 ml 39 % hmot. vodného roztoku etylamínu a po 40 minútach sa přidalo 50 ml 10,1 % hmot. vodného roztoku hydroxidu sodného. Zmes sa nechala 50 minút doreagovať. K reakčnej zmesi sa přidalo 0,03 g odpeňovača na báze polymetylsiloxanu (Lukosan S). Potom sa technický atrazín odfiltroval na BuchneriOvom lieviku, premyl s 300 ml vody a vysušil pri 105 °C. Získalo sa 33,4 g technického atrazínu s obsahom 96,4 % hmot. atrazínu, 1,6 % hmot. 2,4-dietylamíno-6-chlór-s-triazínu (simazinuj a 0,8 % hmot. 2,4-diizopropylamíno-6-chlór-s-triazínu (propazínu j.The reaction flask was charged with 250 mL of water. After cooling to 5 ' C, 30 g of cyanuric chloride was added to the water. 0.1 ml of a copolymer of ethylene oxide and propylene oxide known under the trade name Slovanik T 610 were added to the mixture. Then 50 ml of 20.2 percent were added successively. wt. % aqueous isopropylamine and after 30 minutes 55 ml 10.0 wt. aqueous sodium hydroxide solution. The temperature was maintained between 5 and 10 ° C. After 50 minutes, 21.5 mL of 39 wt. of aqueous ethylamine solution and after 40 minutes, 50 ml of 10.1 wt. aqueous sodium hydroxide solution. The mixture was allowed to react for 50 minutes. 0.03 g of a polymethylsiloxane-based defoamer (Lukosan S) was added to the reaction mixture. The technical atrazine was then filtered on a Buchner funnel, washed with 300 ml of water and dried at 105 ° C. 33.4 g of technical atrazine with a content of 96.4% by weight were obtained. atrazine, 1.6 wt. 2,4-diethylamino-6-chloro-s-triazine (simazine and 0.8 wt.% 2,4-diisopropylamino-6-chloro-s-triazine (propazine i.
Příklad 2Example 2
Postupovalo sa podlá příkladu 1 s tým rozdielom, že sa miesto vody přidalo do banky 250 ml 10 % hmot, roztoku chloridu sodného. Získalo sa 33,8 g technického atrazínu s obsahom 96,9 % hmot. atrazínu, 1,3 % hmot. simazlnu a 1,1 % hmot. propazínu.The procedure of Example 1 was followed except that 250 ml of 10% by weight sodium chloride solution was added to the flask instead of water. 33.8 g of technical atrazine with a content of 96.9% by weight were obtained. atrazine, 1.3 wt. % simazine and 1.1 wt. propazine.
chodným názvom Abeson NAM. Získalo saknown as Abeson NAM. Obtained
34,3 g technického! atrazínu s obsahom 96,4 percenta hmoit. atrazínu, 1,3 % hmot. simazínu a 1,8, % hmot. propazínu.34.3 g technical! atrazine containing 96.4 percent hmoit. atrazine, 1.3 wt. % simazine and 1.8 wt. propazine.
Vynález nájde uplatnenie pri výrobě technického atrazínu, ktorý sa používá ako herbicid v polnohospodárstve.The invention finds application in the production of technical atrazine, which is used as a herbicide in agriculture.
Příklad 3Example 3
Postupovalo sa podl'a příkladu 1 s tým rozdielom, že sa do banky miesto vody dalo 250 ml 5 % hmot. roztoku chloridu draselného a miesto Slovaniku T 610 sa přidalo 0,1 ml vodného roztoku sodnej soli dodecylbenzénsulfónovej kyseliny známej pod ob-The procedure of Example 1 was followed except that 250 ml of 5 wt. solution of potassium chloride and 0.1 ml of an aqueous solution of sodium dodecylbenzenesulfonic acid known under the procedure
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS861809A CS254686B1 (en) | 1986-03-15 | 1986-03-15 | Process for preparing raw 2-isopropylamino-4-ethylamino-6-chlor-s-triazine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS861809A CS254686B1 (en) | 1986-03-15 | 1986-03-15 | Process for preparing raw 2-isopropylamino-4-ethylamino-6-chlor-s-triazine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS180986A1 CS180986A1 (en) | 1987-05-14 |
| CS254686B1 true CS254686B1 (en) | 1988-01-15 |
Family
ID=5353411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS861809A CS254686B1 (en) | 1986-03-15 | 1986-03-15 | Process for preparing raw 2-isopropylamino-4-ethylamino-6-chlor-s-triazine |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS254686B1 (en) |
-
1986
- 1986-03-15 CS CS861809A patent/CS254686B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS180986A1 (en) | 1987-05-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3684432A (en) | Weak acid salts of hydroxylamine | |
| PL164908B1 (en) | Method for the production of ethylenediaminetetra/methylenephosphonic acid/ PL PL PL PL | |
| CS254686B1 (en) | Process for preparing raw 2-isopropylamino-4-ethylamino-6-chlor-s-triazine | |
| CS252897B1 (en) | Method of technical 2-isopropylamino-4-ethylamino-6-chloro-s-triazine production | |
| JPH0338306B2 (en) | ||
| CS253429B1 (en) | Process for preparing 2-isopropylamino-4-ethylamino-6-chlor-s-triazine | |
| US4374818A (en) | Process for the preparation of alkali metal salts of imidodisulfonic acid | |
| US3436394A (en) | Process for the production of 2,4-alkylamino-6-chloro-s-triazines | |
| CS252898B1 (en) | Method of 2-isopropylamino-4-ethylamino-6-chloro-s-triazine preparation | |
| US3907795A (en) | 3-(Tetrahydro-2-pyranyl)-1,3,5-triazinediones and their use as herbicides | |
| US2524054A (en) | Preparation of guanidine salts | |
| US3681335A (en) | SUPPRESSION OF TRIS(ALKYLAMINO)-S-TRIAZINE FORMATION IN THE PRODUCTION OF CHLORO-BIS(ALKYLAMINO)-S-TRIAZINES THROUGH ADJUSTMENT OF pH | |
| US3423411A (en) | Purification of melamine solutions | |
| CS258211B1 (en) | Method of 2-isopropylamino-4-ethylamino-6-chloro-s-triazine preparation | |
| US4978797A (en) | Process for the preparation of 2-hydroxy-4-(hydroxyalkoxy)-benzophenone | |
| Haworth et al. | 161. Some properties of urea, biuret, and triuret | |
| JPS6141348B2 (en) | ||
| US2712002A (en) | Method for purifying crude cyanuric | |
| SU535318A1 (en) | Method of producing ion exchangers | |
| US3299060A (en) | Method for producing stable salts of dichloroisocyanuric acid | |
| US2653976A (en) | Guanidine sulfate from urea and sulfur dioxide | |
| CS219294B2 (en) | Method of making the 4-chlor-5-amino-2-phenyl-3/2h/-pyridazine z 4,5-dichlor-2-phenyl-3/2h/-pyridazinone and ammonium | |
| US4405783A (en) | Process for the production of dihydroxypropyltheophylline | |
| CS272646B1 (en) | Method of technical 2-isopropylamino-4-ethylamino-6-chloro-s-triazine | |
| RU1651523C (en) | Method of obtaining diacetonacrylamide |