CS225083B1 - The analysis of substituted phenoxyacetic acids by means of triphenylmethane colouring agents - Google Patents
The analysis of substituted phenoxyacetic acids by means of triphenylmethane colouring agents Download PDFInfo
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- CS225083B1 CS225083B1 CS146081A CS146081A CS225083B1 CS 225083 B1 CS225083 B1 CS 225083B1 CS 146081 A CS146081 A CS 146081A CS 146081 A CS146081 A CS 146081A CS 225083 B1 CS225083 B1 CS 225083B1
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- CS
- Czechoslovakia
- Prior art keywords
- triphenylmethane
- analysis
- acid
- phenoxyacetic acids
- colouring agents
- Prior art date
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- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 title claims description 21
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004458 analytical method Methods 0.000 title description 4
- 239000004150 EU approved colour Substances 0.000 title 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 title 1
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000000605 extraction Methods 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 238000005375 photometry Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 2
- 239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 2
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 2
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 2
- 239000012491 analyte Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- HLVXFWDLRHCZEI-UHFFFAOYSA-N chromotropic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HLVXFWDLRHCZEI-UHFFFAOYSA-N 0.000 description 2
- SMYMJHWAQXWPDB-UHFFFAOYSA-M (2,4,5-trichlorophenoxy)acetate Chemical compound [O-]C(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-M 0.000 description 1
- YHUMTHWQGWPJOQ-UHFFFAOYSA-N 2,6-dichloro-4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=C(Cl)C(=O)C(Cl)=C1 YHUMTHWQGWPJOQ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QUPKNTOOYAFDAR-UHFFFAOYSA-N NC1=CC=C(C=C1)C(O)(C=1C=C(C=CC=1N)C)C1=CC=C(C=C1)N Chemical compound NC1=CC=C(C=C1)C(O)(C=1C=C(C=CC=1N)C)C1=CC=C(C=C1)N QUPKNTOOYAFDAR-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000033558 biomineral tissue development Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000011197 physicochemical method Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Landscapes
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Description
Vynález se týká způsobu analýzy herbicidů typu fenoxyoctových kyselin* u nichž se po extrakci z vodného roztoku do lipofilního rozpouštědla stanoví koncentrace složky metodou extrakční fotometrie, resp· spektrofotometrie·The invention relates to a method for the analysis of phenoxyacetic acid herbicides in which, after extraction from an aqueous solution into a lipophilic solvent, the concentration of the component is determined by means of extraction photometry or spectrophotometry.
Fenoxyoctové kyseliny jsou důležitou součásti průmyslově vyráběných herbicidů a jejich směsí· Jejich stanovení ve vzorcích se nejčastěji provádí fyzikálně chemickými metodami analýzy· Byly rovněž popsány způsoby separační analýzy chromatografické a využito iontoměničů (Žemčužin, S.G. - Akimova, N.N·, Avt· svidětel. SSSR, 298 885)· Metoda extrakční fotometrie byla vypracována také pro povrchově aktivní látícy (Pat. USA, 3992 149;Phenoxyacetic acids are an important component of industrially produced herbicides and mixtures thereof. Their determination in samples is most often carried out by physicochemical methods of analysis. 298 885) · The extraction photometry method has also been developed for surfactants (Pat. USA, 3992 149;
Scott, G.V., Anályt. Chem·, 1968, s. 768, Wahbi, A.M. - Abine, H. - Koraný, M.A. - Abdel - Hay, M.H., Anály st, 103, 1978, s· 876). Dosud však nebyl tento postup využit pro analýzu fenoxyoctových kyselin ve směsích herbicidů·Scott, G.V., Annals. Chem., 1968, 768, Wahbi, A.M. - Abine, H. - Quran, M.A. - Abdel-Hay, M.H., Annals, 103, 1978, p. 876). However, this procedure has not yet been used for the analysis of phenoxyacetic acids in herbicide mixtures.
Mezi dříve uváděné způsoby analýzy patří reakce s činidly na bázi kyseliny sírové· Bylo zjištěno, že pro detekci kyseliny 2,4-dichlorfenoxyoctové se osvědčila kyselina chromotropová (Bricker, C.E. - Johnson, G.R·, Ind. Engng. Chem· Anályt· Edit· 17, 1945, s. 400; Freed, W.H., Science 107, 1948, s. 98, Mangnardt, R.P. - Luče, E.N., Analyt. Chem., 23, 1951, s· 1484).Methods previously mentioned include reactions with sulfuric acid reagents · Chromotropic acid (Bricker, CE - Johnson, GR, Ind. Eng. Chem.) Annals · Edit · It has been found that chromotropic acid has been proven to detect 2,4-dichlorophenoxyacetic acid. 17, 1945, p. 400; Freed, WH, Science 107, 1948, p. 98, Mangnardt, RP-Luče, EN, Analyt. Chem., 23, 1951, p. 1484).
Aromatický charakter fenoxyoctových kyselin umožňuje reakci s 2,6-dichlorchinon-4-chlorimidem, kdy vzniká modré zbarvení (Feigl, F. - Jungreis, E·, Analyt· Chem. 31, 1959, s. 2099).The aromatic character of phenoxyacetic acids allows reaction with 2,6-dichloroquinone-4-chlorimide to produce a blue color (Feigl, F.-Jungreis, E, Analyt. Chem. 31, 1959, p. 2099).
Činidly na bázi kyseliny sírové však nelze stanovit fenoxyoctové kyseliny v přítomnosti jiných látek aromatického charakteru a silné dehydratační účinky a oxidační schopnost koncentrované kyseliny sírové způsobují mineralizaci organických sloučeninHowever, phenoxyacetic acids in the presence of other aromatic substances cannot be detected with sulfuric acid reagents and the strong dehydrating effects and oxidizing capacity of concentrated sulfuric acid cause the mineralization of organic compounds
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Výše Uvedené nedostatky jsou odstraněny stanovením podle vynálezu, jehož podstatou je způsob analýzy substituovaných fenoxyoctových kyselin trifenylmetkáňovými barvivý, kdy sena vzorek substituované fenoxyoctové kyseliny, například monohalogenfenoxyoctové, dihalogenfenoxyoctové a trihalogenfenoxyoctové, působí vodným roztokem trifenylmethanového barviva o pH 6 až 9 a extrahuje se směsí uhlovodíkových lipofilních rozpouštědel, například chloridu uhličitého, chloroformu a 1,1^2,2*-tetrachlorethanu v objemovém poměru 1 :2:1a obsah substituované fenoxyoctové kyseliny se stanoví fotometricky.The above drawbacks are overcome by the assay of the present invention, which is based on a method of analyzing substituted phenoxyacetic acids with triphenylmethane dyes, where a hay sample of substituted phenoxyacetic acid, e.g. solvents such as carbon tetrachloride, chloroform and 1,1,2,2'-tetrachloroethane in a 1: 2: 1 by volume ratio. the content of substituted phenoxyacetic acid is determined photometrically.
Příklad 1Example 1
Byl připraven zásobní methanolový roztok kyseliny 2,4,5-trichlorΛ V fenoxyoctové o koncentraci 5,7.10” mol.1**· Pipetováním do extrakčních zkumavek a následným odpařením methanolu byla vytvořena řada vzorků o stoupající hmotnosti odparku od 0,1 do 1,46 mg kyseliny 2,4,5-trichlorfenoxyoctové. K odparkům ve zkumavkách bylo —4 — 1 postupně přidáno po 2 ml zásobního vodného roztoku 5.10 mol.l bis(p-aminofenyl)-4-amino-m-tolylmethanolu o 'pH 7,1. Vodný roztok byl vy třepán se směsí chloroformu a ΐ,ΐζ2,2*-tetrachlorethanu v * objemovém poměru 1 : 1. Extrakt byl doplněn v odměrné bance na ml a měřena absorbance při 556 nm. Mez stanovitelnosti kyseliny -5 -1A stock methanol solution of 2,4,5-trichloro-V in phenoxyacetic acid at a concentration of 5.7.10 ”mol was prepared ** ** · A series of samples with increasing evaporator mass from 0.1 to 1 was created by pipetting into extraction tubes and subsequent evaporation of methanol. 46 mg 2,4,5-trichlorophenoxyacetic acid. To the evaporators in the tubes, -4-1 was added sequentially with 2 ml of a stock aqueous solution of 5.10 mol.l of bis (p-aminophenyl) -4-amino-m-tolylmethanol, pH 7.1. The aqueous solution was shaken with a mixture of chloroform and ΐ, ,22,2 * -tetrachloroethane in a 1: 1 volume ratio. The extract was made up in a volumetric flask per ml and the absorbance measured at 556 nm. Determination limit of acid -5 -1
2,4,5-trichlorfenoxyoctové činila 1,4.10 mol.l .2,4,5-trichlorophenoxyacetate was 1.4.10 mol.l.
Příklad 2Example 2
Byl připraven zásobní methanolový roztok kyseliny 4-methyl-2-chlor -3 -1 fenoxyoctové o koncentraci 7,1.10 mol.l · Pipetovánim do extrakčních zkumavek s následným odpařením methanolu byla vytvořena řada vzorků o stoupající hmotnosti odparku od 0,1 do 1,44 mg. Postupně bylo přidáno po 3 ml vodného roztoku bis(p-aminofenyl)-4-amino-m-4 -1A methanol stock solution of 4-methyl-2-chloro-3-phenoxyacetic acid of 7.1.10 mol.l was prepared. * Pipette into extraction tubes followed by evaporation of methanol to produce a series of samples with increasing evaporator mass from 0.1 to 1, 44 mg. Subsequently, 3 ml of an aqueous solution of bis (p-aminophenyl) -4-amino-m-4-1 was added
-tolylmethanolu pH 7,8 a koncentraci 3,10 mol.l . Potom byla vod ná fáze vytřepána s 1,2,2*-tetrachlorethanem, extrakt doplněn v odměrné baňce na 25 ml. Obsah fenoxyoctové kyseliny byl stanoven spektrofotometricky při 565 nm. Mez stanovitelnosti činila 1,43.10^0101.1^1 4-methyl-2-chlorfenoxyoctové kyseliny.-tolylmethanol pH 7.8 and a concentration of 3.10 mol.l. The aqueous phase was then shaken with 1,2,2 * -tetrachloroethane, and the extract made up to a 25 ml volumetric flask. The phenoxyacetic acid content was determined spectrophotometrically at 565 nm. The limit of quantification was 1,43.10 ^ 0101.1 ^ 1 4-methyl-2-dichlorophenoxyacetic acid.
Příklad 3Example 3
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Byl připraven zásobní methanolový roztok kyseliny 2,4-dichlor-3 -1 fenoxyoctové o koncentraci 6,5.10 mol.l . Pipetováním do extrakčních zkumavek a následným odpařením rozpouštědla byla vytvořena řada vzorků o stoupající hmotnosti odparku od 0,1 do 1,4 mg· Postupně byl přidán 1 ml vodného roztoku dimethylamino-4^methylethylamonium-dimethylfuchsonium chloridu a bromidu o koncentraci 4.104mol.l”1 a pH 8,2· Potom byla vodná fáze extrahována směsi chloridu uhličitého, chloroformu a 1,1*2,2-tetrachlorethanu v objemovém poměru 1:2:1a extrakt v odměrné baňce doplněn na 25 ml. Obsah kyseliny 2,4-dichlorfenoxyoctové ve vzorku byl stanoven spektrofotometricky při 625 nm· Bylo zjištěno, že nejmenší stanovitelné množství je 5 ng fenoxyoctové kyseliny, což odpo-5 ř -1 vídá koncentraci 2,2.10 mol.l ·A stock methanol solution of 2,4-dichloro-3-phenoxyacetic acid of 6.5.10 mol.l was prepared. Pipetting into extraction tubes, and subsequent evaporation was developed a number of samples of increasing the weight of the residue from 0.1 to 1.4 mg · was gradually added 1 ml of an aqueous solution of 4-dimethylamino-methylethylamonium dimethylfuchsonium chloride or bromide concentration of about 4.10 with 4 M "1 and pH 8.2 · aqueous phase was then extracted with carbon tetrachloride, chloroform and 1,1 * 2,2-tetrachloroethane in a ratio of 1: 2: 1 extract in the volumetric flask up to 25 ml. Content of 2,4-dichlorophenoxyacetic acid in the sample was determined spectrophotometrically at 625 nm · It has been found that the smallest detectable amount of 5 ng of phenoxyacetic acid, a 5-deduction of the concentration of 2,2.10 Vida -1 mol.l ·
Příklad 4Example 4
Byl připraven methanolový roztok kyseliny 2,4,5-trichlorfenoxy—4 —1 octové o koncentraci 5,6.10 mol.l · Pipetováním a následným odpařením rozpouštědla byla vytvořena řada vzorků o stoupájící hmotnosti od 0,1 do 1,5 mg. Postupně bylo přidáno po 1 ml vodného roztoku 2,4,6,2^4^2*^4**-pentamethoxytrifenylkarbinolu o koncentraci S.lO^mol.l-1 a pH 7,3. Potom byla vodná fáze extrahována chloroformem a extrakt doplněn na 25 ml. Obsah 2,4,5-trichlorfenoxyoctové kyseliny byl stanoven fotometričky při 613 nm. Mez stáno?' .ς «.i vitelnosti činila 1,1.10 mol.l uvedené sloučeniny.A methanol solution of 2,4,5-trichlorophenoxy-4-acetic acid with a concentration of 5.6.10 mol.l was prepared. A series of samples with increasing weight from 0.1 to 1.5 mg was produced by pipetting and subsequent evaporation of the solvent. Subsequently, 1 ml of an aqueous solution of 2,4,6,2,4,4,2,2,4,4,4-pentamethoxytriphenylcarbinol having a concentration of S. 10 -4 mol.l -1 and a pH of 7.3 was added in succession. Then the aqueous phase was extracted with chloroform and the extract was made up to 25 ml. The 2,4,5-trichlorophenoxyacetic acid content was determined by photometry at 613 nm. The limit of a tent? ' The compound had a viscosity of 1.1.10 mol.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS146081A CS225083B1 (en) | 1981-03-02 | 1981-03-02 | The analysis of substituted phenoxyacetic acids by means of triphenylmethane colouring agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS146081A CS225083B1 (en) | 1981-03-02 | 1981-03-02 | The analysis of substituted phenoxyacetic acids by means of triphenylmethane colouring agents |
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| Publication Number | Publication Date |
|---|---|
| CS225083B1 true CS225083B1 (en) | 1984-02-13 |
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| Application Number | Title | Priority Date | Filing Date |
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| CS146081A CS225083B1 (en) | 1981-03-02 | 1981-03-02 | The analysis of substituted phenoxyacetic acids by means of triphenylmethane colouring agents |
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1981
- 1981-03-02 CS CS146081A patent/CS225083B1/en unknown
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