CS256087B1 - Method of 2-methyl-4-chlorophenoxyacetic acid's dimethylamine salt production - Google Patents
Method of 2-methyl-4-chlorophenoxyacetic acid's dimethylamine salt production Download PDFInfo
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- CS256087B1 CS256087B1 CS574286A CS574286A CS256087B1 CS 256087 B1 CS256087 B1 CS 256087B1 CS 574286 A CS574286 A CS 574286A CS 574286 A CS574286 A CS 574286A CS 256087 B1 CS256087 B1 CS 256087B1
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- Czechoslovakia
- Prior art keywords
- methyl
- dimethylamine
- acid
- chlorophenoxyacetic acid
- dimethylamine salt
- Prior art date
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- 125000002147 dimethylamino group Chemical class [H]C([H])([H])N(*)C([H])([H])[H] 0.000 title claims abstract description 16
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 title claims description 25
- 239000005574 MCPA Substances 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 8
- 239000012535 impurity Substances 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 239000000725 suspension Substances 0.000 claims abstract description 4
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 3
- 239000007788 liquid Substances 0.000 claims description 5
- 229940045919 sodium polymetaphosphate Drugs 0.000 claims description 3
- 239000002253 acid Substances 0.000 abstract description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract description 4
- 239000011734 sodium Substances 0.000 abstract description 4
- 229910052708 sodium Inorganic materials 0.000 abstract description 4
- 239000004009 herbicide Substances 0.000 abstract description 3
- 238000001556 precipitation Methods 0.000 abstract description 3
- 230000002363 herbicidal effect Effects 0.000 abstract description 2
- 239000010802 sludge Substances 0.000 abstract description 2
- FBZWYFBNIGSUPS-UHFFFAOYSA-N (2-chlorophenyl) ethaneperoxoate Chemical compound CC(=O)OOC1=CC=CC=C1Cl FBZWYFBNIGSUPS-UHFFFAOYSA-N 0.000 abstract 1
- -1 2-methyl-4-chlorophenoxy Chemical group 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 235000019271 petrolatum Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 description 9
- QJVXBRUGKLCUMY-UHFFFAOYSA-N 2-(2-methylphenoxy)acetic acid Chemical compound CC1=CC=CC=C1OCC(O)=O QJVXBRUGKLCUMY-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000012266 salt solution Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- PKAUICCNAWQPAU-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetic acid;n-methylmethanamine Chemical compound CNC.CC1=CC(Cl)=CC=C1OCC(O)=O PKAUICCNAWQPAU-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical class [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 235000012254 magnesium hydroxide Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- RHLLDTPGTFRJDJ-UHFFFAOYSA-N OCl.OCl Chemical compound OCl.OCl RHLLDTPGTFRJDJ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000001875 compounds Chemical group 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HKNMVNAPCMXVTR-UHFFFAOYSA-M sodium;2-(2-methylphenoxy)acetate Chemical compound [Na+].CC1=CC=CC=C1OCC([O-])=O HKNMVNAPCMXVTR-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Rieši sa příprava dimetylamínovej soli ky seliny 2-metyl-4-chlórfenoxyoctovej neutra lizáciou 2-m<etyil-4-chlórfenoxyoctovej kyse liny plynným dimetylamínom. 2-metyl-4- -chlórfenoxyoctová kyselina je suspendova ná vo vodnom roztoku dimetylamínovej soli 2-metyl-4-chlórfenoxyoctovej kyseliny. Do suspenzie sa privádza plynný dimetylamín. Po neutralizácií je možné vyzrážané nečis toty vo formě kalu odfiltrovat. Výhodné je možné neutralizáciu robit v přítomnosti po- lyraetafosforečňanu sodného, ktorý zabraňu je vyzrážaniu nerozpustných kovových zlú čenín. Riešenie najde uplatnenie pri výrobě dimetylamínovej soli 2-metyl-4?chlórfenoxy- octovej kyseliny, ktorá sa používá ako herbicid.solves the preparation dimethylamine salt ky petroleum jelly 2-methyl-4-chlorophenoxy Neutra drying of the 2-m <etyil-4-chlorophenoxy kyse liny gaseous dimethylamine. 2-methyl-4- -chlórfenoxyoctová acid is a suspendability on the within water solution of dimethylamine salt 2-methyl-4-chlorophenoxy acid. To suspension the leads gaseous dimethylamine. After neutralization is a possible precipitated impurity toty within as a sludge filter. preferred is a possible neutralizing do in presence after- lyraetafosforečňanu sodium, which Prevents is a precipitation suspended metal bad valuables. solution finds enforcement at production dimethylamine salt 2-methyl-4? Chlorophenoxy acetate acid, which the uses how herbicide.
Description
Vynález sa týká spósobu výroby dimetylamínovej soli kyseliny 2-metyl-4-chlórfenoxyoctovej neutralizáciou technickej 2-metyl-4-clilórfenoxyoctovej kyseliny s dimetylamínom.The present invention relates to a process for preparing a dimethylamine salt of 2-methyl-4-chlorophenoxyacetic acid by neutralizing industrial 2-methyl-4-chlorophenoxyacetic acid with dimethylamine.
Kyselina 2-mety]-4-chlórfenoxyoctová a jej soli sa používajú ako velmi účinné herbicidy. Najčaetejšie sa připravuje chloráciou 2-metylfenoxyoetovej kyseliny plynným chlórom pri teplote 96 až 105 °C, ako je opásané v čs. patente 91160.2-Methyl-4-chlorophenoxyacetic acid and its salts are used as highly effective herbicides. Most commonly it is prepared by chlorination of 2-methylphenoxyoetic acid with chlorine gas at a temperature of 96 to 105 ° C, as described in U.S. Pat. No. 91160.
Kontinuálny sposob chlorácie sodnej, draselnej alebo sodnodraselnej soli 2-metylfenoxyoctovej kyseliny vo vodnom roztoku je písaný v čs. patente 99 892, kontinuálny sposob chlorácie voTnej 2-metylfenoxyoctovcj kyseliny plynným chlórom opisuje čs. patent 107 807.The continuous mode of chlorination of the sodium, potassium or sodium potassium salt of 2-methylphenoxyacetic acid in aqueous solution is described in US Pat. No. 99,892, a continuous method of chlorination in free 2-methylphenoxyacetic acid with chlorine gas is disclosed in U.S. Pat. No. 107,807.
Možnost komblnácie chlorácie 2-metylfenoxyoctovej kyseliny plynným chlórom s výsledným dochlórovaním chlórňanom uvádza čs. AO 172 188. Chloráciu 2-metylfenoxyoctovej kyseliny plynným chlórem pri hodnotě pH 4 až 6 opisuje francúzsky patent 1 116 266.The possibility of combining the chlorination of 2-methylphenoxyacetic acid with chlorine gas with the resultant hypochlorite hypochlorite is reported in MS. AO 172 188. Chlorination of 2-methylphenoxyacetic acid with chlorine gas at a pH of 4 to 6 is described in French patent 1,116,266.
Chloráciu vodným roztokom chlorňanu sodného připraveného vopred alebo „in šitu“ v reakčnej zmesi pri teplote 50 °C opisuje patent V. Británie 722 625. Chloráciu suspendovanej 2-metylfenoxyoctovej kyseliny pri hodnotě pH rovnej 1 v heterogénnej fáze za přítomnosti kyseliny chlórovodíkovej chlórňanom sodným pri teplote 20 °C opisuje DAS 1 027 680. Spósob založený na působení hydroxidu sodného alebo uhličitanu sodného vodný roztok sodnej soli 2-metylfenoxyoctovej kyseliny a chloráciu chlórom opisuje pat. USA 2 770 651. Chloráciu sodnej soli 2-metylfenoxyoctovej kyseliny chlórom v přítomnosti hydrouhličitanu je opísaný v pat. V. Británie 855 504. Výrobu 2-mety,l-4-chlórfenoxyoctovej kyseliny pomocou chlórňanu sodného v přítomnosti minerálnej alebo karboxylovej kyseliny, výrobu 2-metylfenoxyoctovej kyseliny a získanie 2-metyl-4-chlórfenoxyoctovej kyseliny vyzrážaním s prebytkom vodného roztoku minerálnej kyseliny opisuje čs. AO 179 200.Chlorination with an aqueous solution of sodium hypochlorite prepared in advance or "in situ" in the reaction mixture at 50 ° C is described in U.S. Patent 722,625. Chlorination of suspended 2-methylphenoxyacetic acid at a pH equal to 1 in heterogeneous phase in the presence of hydrochloric acid 20 ° C describes DAS 1 027 680. A method based on the action of sodium hydroxide or sodium carbonate aqueous solution of sodium salt of 2-methylphenoxyacetic acid and chlorination by chlorine is described in U.S. Pat. U.S. 2,770,651. Chlorination of 2-methylphenoxyacetic acid sodium salt with chlorine in the presence of bicarbonate is described in U.S. Pat. United Kingdom 855 504. The production of 2-methyl, 1-4-chlorophenoxyacetic acid using sodium hypochlorite in the presence of mineral or carboxylic acid, the production of 2-methylphenoxyacetic acid and the recovery of 2-methyl-4-chlorophenoxyacetic acid by precipitation with an excess aqueous mineral acid solution are described. MS. AO 179 200.
Pri výrobě dimetylamínovej soli kyseliny 2-metyl-4-chlórfenoxyoctovej sa na neutralizáciu najčastejšie používá vodný roztok dimetylamínu, pričom vzniká dimetylamínová sol' kyseliny 2-metyl-4-chlórfenoxyoctovej o poměrně nízkej koncentráeii. Pri neutralizácii sa vyzrážajú vo· formě kalu hydroxidy železitý, horečnatý, ktoré znečisťujú produkt.In the preparation of the dimethylamine salt of 2-methyl-4-chlorophenoxyacetic acid, an aqueous solution of dimethylamine is most often used for neutralization, resulting in a dimethylamine salt of 2-methyl-4-chlorophenoxyacetic acid of relatively low concentration. Upon neutralization, ferric and magnesium hydroxides precipitate in the form of sludge, contaminating the product.
Vyššie uvedené nedostatky sú zmiernené spósobom výroby dimetylamínovej soli kyseliny 2-metyl-4-chlórfenoxyoctovej, podstata ktorého spočívá v tom, že sa technická kyselina 2-metyl-4-chlórfenoxyoctová vo formě suspenzie vo vodnom roztoku dimetylamínovej soli 2-metyl-4-chlórfenoxyoctovej kyseliny neutralizuje plynným a/alebo kvapalným dinietylamínom.The above-mentioned drawbacks are alleviated by the process for the preparation of the dimethylamine salt of 2-methyl-4-chlorophenoxyacetic acid, which consists in the technical suspension of 2-methyl-4-chlorophenoxyacetic acid in the form of a suspension in an aqueous solution of the dimethylamine salt of 2-methyl-4-chlorophenoxyacetic acid acid is neutralized by gaseous and / or liquid diethylamine.
Neutralizácia 2-metyl-4-chlórfenoxyoctovej kyseliny s plynným a/alebo kvapalným dimetylamínom sa robí v přítomnosti polymetafosforečňanu sodného. V případe, že sa nepoužije ipolymetafosforečňan sodný vyzrázené nečistoty sa oddelia od roztoku dimetylamínovej soli 2-metyl-4-chlórfenoxyoctovej kyseliny.Neutralization of 2-methyl-4-chlorophenoxyacetic acid with gaseous and / or liquid dimethylamine is carried out in the presence of sodium polymetaphosphate. In the absence of sodium ipolymetaphosphate, the precipitated impurities are separated from the solution of the dimethylamine salt of 2-methyl-4-chlorophenoxyacetic acid.
Postupom podta vynálezu sa dosiahne vyššia koncentrácía vzniknutého roztoku dimetylamínovej soli ako pri použití vodného roztoku dimetylamínu. Výhodnéjšie je na neutralizáciu použil: kvapalný dimetylamín, a to podchladený pod 5 °C za normálnych podmienok.The process according to the invention achieves a higher concentration of the resulting dimethylamine salt solution than with an aqueous dimethylamine solution. More preferably, liquid dimethylamine is used for neutralization, and is cooled below 5 ° C under normal conditions.
Získaný produkt je bez zákalu od vyzrážaných hydroxidov železitého a horečnatého. Katióny vyššie uvedených zlúčenín tvoři a « polymetafosforečňanom sodným rozpustný komplex, ktorý při daných podmienkach zabráni ich vyzrážaniu, čím sa zlepší kvalita získaného produktu a netřeba vyzrázené nečistoty z produktu odstraňovat filtráciou.The product obtained is free of haze from the precipitated ferric and magnesium hydroxides. The cations of the above compounds form a sodium polymetaphosphate soluble complex which prevents precipitation under the given conditions, thereby improving the quality of the product obtained and the need not to remove precipitated impurities from the product by filtration.
Příklad 1Example 1
Do banky sa dalo 500 ml 28 % hmot. vodného roztoku dimetylamínovej soli 2-metyl-4-chlórfenoxyoctovej kyseliny. Za stálého miešania sa do banky postupné přidával filtračný koláč technickej kyseliny 2-metyl-4-chlórfenoxyoctovej s obsahom 56,3 % hmot. sušiny a 51,1 % hmot. 2-metyl-4-chlórfenoxyoclovej kyseliny. Súčasne sa do banky zavádzal plynný dimetylamín.500 ml of 28 wt. aqueous solution of 2-methyl-4-chlorophenoxyacetic acid dimethylamine salt. With stirring, a 2-methyl-4-chlorophenoxyacetic acid filter cake containing 56.3% by weight was gradually added to the flask. % solids and 51.1 wt. Of 2-methyl-4-chlorophenoxyacetic acid. At the same time, dimethylamine gas was introduced into the flask.
Privádzanie dmetylamínu sa robilo za stálého chladenia. Roztok dimetylamínovej soli sa přefiltroval. Získaný roztok obsahovalThe supply of dmethylamine was done with constant cooling. The dimethylamine salt solution was filtered. The obtained solution contained
61,1 °/o hmot. dimetylamínovej soli 2-metyl-4-chlórfenoxyoctovej kyseliny.61.1% w / w dimethylamine salt of 2-methyl-4-chlorophenoxyacetic acid.
Příklad 2Example 2
Postupovalo sa podl'a příkladu 1 s tým rozdielom, že sa před neutralizáciou přidalo k dimetylamínovej soli 2-metyl-4-chlórfenoxyoctovej kyseliny hexymetafosforeňan sodný, aby jeho výsledná koncentrácía v získanom roztoku dimetylamínovej soli 2-metyl-4-chlórfenoxyoctovej bolí přibližné 0,5 g/1. Získaný roztok dimetylamínovej soli 2-metyl-4-chlórfenoxyoctovej kyseliny bol bez zákalu a nefiltroval sa. Obsahoval 60,3 pere. hmot. 2-metyl-4-chlórfenoxyoctovej kyseliny.The procedure of Example 1 was followed except that 2-methyl-4-chlorophenoxyacetic acid, sodium hexymetaphosphate was added to the dimethylamine salt of 2-methyl-4-chlorophenoxyacetic acid to neutralize the resulting concentration in the obtained 2-methyl-4-chlorophenoxyacetic acid dimethylamine salt solution. 5 g / l. The obtained 2-methyl-4-chlorophenoxyacetic acid dimethylamine salt solution was cloudless and was not filtered. It contained 60.3 pens. wt. Of 2-methyl-4-chlorophenoxyacetic acid.
Vynález nájde uplatnenie pri výrobě dimetylamínovej soli 2-metyl-4-chlórfenoxyoctovej kyseliny, ktorá sa používá ako herbicid v polnohospodárstve.The invention finds application in the production of the dimethylamine salt of 2-methyl-4-chlorophenoxyacetic acid, which is used as an herbicide in agriculture.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS574286A CS256087B1 (en) | 1986-07-31 | 1986-07-31 | Method of 2-methyl-4-chlorophenoxyacetic acid's dimethylamine salt production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS574286A CS256087B1 (en) | 1986-07-31 | 1986-07-31 | Method of 2-methyl-4-chlorophenoxyacetic acid's dimethylamine salt production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS256087B1 true CS256087B1 (en) | 1988-04-15 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS574286A CS256087B1 (en) | 1986-07-31 | 1986-07-31 | Method of 2-methyl-4-chlorophenoxyacetic acid's dimethylamine salt production |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS256087B1 (en) |
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1986
- 1986-07-31 CS CS574286A patent/CS256087B1/en unknown
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