CS265658B1 - A method for the quantitative determination of by-products in tetrabromdian - Google Patents

A method for the quantitative determination of by-products in tetrabromdian Download PDF

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CS265658B1
CS265658B1 CS86704A CS70486A CS265658B1 CS 265658 B1 CS265658 B1 CS 265658B1 CS 86704 A CS86704 A CS 86704A CS 70486 A CS70486 A CS 70486A CS 265658 B1 CS265658 B1 CS 265658B1
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CS
Czechoslovakia
Prior art keywords
products
quantitative determination
tetrabromo
analysis
tetrabromdian
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CS86704A
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Czech (cs)
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CS70486A1 (en
Inventor
Jana Ing Csc Paryzkova
Ivan Ing Csc Kolb
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Paryzkova Jana
Ivan Ing Csc Kolb
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Priority to CS86704A priority Critical patent/CS265658B1/en
Publication of CS70486A1 publication Critical patent/CS70486A1/en
Publication of CS265658B1 publication Critical patent/CS265658B1/en

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Abstract

Byla vypracována metoda pro kvantitativní stanovení vedlejších produktů v tetrabromdianu po převedení na trimethyl- silyletftery. Analýza se provádí například na náplňové ohromatografické koloně délky 2,40 m a vnitřním průměru 2 mm při teplotě 250 °C a průtoku nosného plynu 22 ml/min. Kolona je smočena silikonem na bílém nosiči. Za podmínek analýzy je možno stanovit chlor- a bromderiváty fenolu, p-isopropenvlfenolu a dianu.A method was developed for the quantitative determination of by-products in tetrabromide after conversion to trimethylsilylethers. The analysis is carried out, for example, on a packed chromatography column with a length of 2.40 m and an internal diameter of 2 mm at a temperature of 250 ° C and a carrier gas flow of 22 ml / min. The column is wetted with silicone on a white support. Under the conditions of the analysis, the chloro- and bromo derivatives of phenol, p-isopropylene phenol and dian can be determined.

Description

(57)(57)

Byla vypracována metoda pro kvantitativní stanovení vedlejších produktů v tetrabromdianu po převedení na trimethylsilyletftery. Analýza se provádí například na náplňové ohromatografické koloně délky 2,40 m a vnitřním průměru 2 mm při teplotě 250 °C a průtoku nosného plynu 22 ml/min. Kolona je smočena silikonem na bílém nosiči. Za podmínek analýzy je možno stanovit chlor- a bromderiváty fenolu, p-isopropenvlfenolu a dianu.A method has been developed for the quantitative determination of by-products in tetrabromodiane after conversion to trimethylsilyl ethers. The analysis is carried out, for example, on a packed chromatography column of length 2.40 m and internal diameter 2 mm at a temperature of 250 °C and a carrier gas flow rate of 22 ml/min. The column is wetted with silicone on a white support. Under the conditions of the analysis, it is possible to determine the chloro- and bromo-derivatives of phenol, p-isopropenylphenol and diane.

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Vynález se týká kvantitativního stanoveni vedlejších produktů v tetrabromdlanu metodou plynová chromatografie·The invention relates to the quantitative determination of by-products in tetrabromide by gas chromatography.

Tetrabromdien, t.j. 2,2-bi8-(4-hydroxy-3,5-dibrom)-propan, který je významným retardérem hořeni, se vyrábí bromaci dlenu, t.j. 2,2-bis-(4-hydroxyfenyl)-propanu bromem za přítomnosti chloru. Vedle žádaného produktu vzniká řada vedlejších produktů typu substituovaných fenolů, izopropenylfenolů a dianů, např.Tetrabromodiene, i.e. 2,2-bi8-(4-hydroxy-3,5-dibromo)-propane, which is an important flame retardant, is produced by bromination of diene, i.e. 2,2-bis-(4-hydroxyphenyl)-propane, with bromine in the presence of chlorine. In addition to the desired product, a number of by-products such as substituted phenols, isopropenylphenols and dienes are formed, e.g.

X3 Xj X2 - Cl, X3 « Br (I) x2- OH χχ X2 · Br, X3 Cl (II) Χχ xi “ x2 * X3 * Br (I«) X 3 Xj X 2 - Cl, X 3 « Br (I) x 2- OH χ χ X 2 · Br, X 3 Cl (II) Χ χ x i “ x 2 * X 3 * Br (I«)

CH,CH,

0ΗΧ2Χχ X40ΗΧ 2 Χ χ X 4

OHOH

Χχ X3 Cl, X2 « H, X4 - Br (IV)χ χ X 3 Cl, X 2 « H, X 4 - Br (IV)

Χχ « X3 « Br, X2 H, X4 - Cl (V) χχ « X3 . X4 . Br, X2 « Η (VI) X1 x2 x3 · x4 “ Br (VII)χ χ « X 3 « Br, X 2 H, X 4 - Cl (V) χ χ « X 3 . X4 . Br, X 2 « Η (VI) X 1 x 2 x 3 · x 4 “ Br (VII)

X1 - X 1 - X2 X2 B X3 BX 3 X1 X 1 X2 X2 X3X 3 X1 - X 1 - H. H. X2 X2 X1 X 1 X2 X2 X3 ' X 3 X1 X 1 X2 X2 - x3 - x 3 X1 * X 1 * *3 *3 • Cl • Cl X, * X, * X2 X2 . X3 .X 3 X, · X, · X„ X„ x. x.

b X4 Hb X 4 H

H, x4 · Br x4 - Br • Br, X4 HH, x 4 · Br x 4 - Br • Br, X 4 H

Cl, X4 Br χ2 β χ4 b BrCl, X 4 Br χ 2 β χ 4 b Br

Br, X. b cl • X4 - Br (VIII) (IX) (x) (xi) (xii) (xiii) (XIV) (xv)Br, X. b cl • X 4 - Br (VIII) (IX) (x) (xi) (xii) (xiii) (XIV) (xv)

Obsah vedlejších produktů zhoršuje vlastnosti tetrabromdlanu, takže je žádoucí jejich kvalitu i kvantitu analyticky zjistit.The content of by-products deteriorates the properties of tetrabromide, so it is desirable to determine their quality and quantity analytically.

265 658265,658

Metody určené k analýze směsí po bromaci dianu nejsou známy· Publikovány byly pouze metody pro stanoveni tetrabromdianu ve vzduchu» vodě a sedimentech metodami tenkovrstvá chromatografie* plynová chromatografie* kapalinové chromátografie* epektrofotometrie a plynové chromatografie ve spojeni 8 hmotnostní spektrometrii·Methods intended for the analysis of mixtures after bromination of diane are not known. Only methods for the determination of tetrabromodiane in air, water and sediments by the methods of thin-layer chromatography* gas chromatography* liquid chromatography* espectrophotometry and gas chromatography coupled with mass spectrometry have been published.

Nyni byl nalezen způsob kvantitativního stanovení vedlejších produktů v tetrabromdianu* který je předmětem tohoto vynálezu a jehož podstata spočivá v tom, že se tetrabromdian silyluje Silylačním činidlem, s výhodou N*O-bis-(trimethyíeilyl)-trifluoroacetamidem a utvořené trimethylsilylethery tetrabromdianu a vedlejších produktů se podrobí plynové chromatografii na náplňové koloně smočené chlorfenylsilikonovým olejem·A method has now been found for the quantitative determination of by-products in tetrabromideane* which is the subject of the present invention and the essence of which lies in the fact that tetrabromideane is silylated with a silylating agent, preferably N*O-bis-(trimethylethyl)-trifluoroacetamide, and the formed trimethylsilyl ethers of tetrabromideane and by-products are subjected to gas chromatography on a packed column wetted with chlorophenyl silicone oil.

Vzorek se silyluje vhodným silylačním činidlem, nejlépe N«0-bl8-(trlmethyleilyl)-trifluoroacetamidem* za zvýšené teploty a nepřistupu vzdušné vlhkosti· Silylovaný produkt se injektuje do odpeřovaciho prostoru plynového chromatografu a po separaci na náplňové koloně smočené chlorfenylovým silikonem se detekuji složky plamenoionizačnim detektorem· Odezvy detektoru se převedou na obsah složek v původním vzorku·The sample is silylated with a suitable silylating agent, preferably N-O-b18-(trimethylethyl)-trifluoroacetamide* at elevated temperature and in the absence of air humidity. The silylated product is injected into the defoaming space of the gas chromatograph and, after separation on a packed column wetted with chlorophenyl silicone, the components are detected with a flame ionization detector. The detector responses are converted to the content of the components in the original sample.

Způsob stanoveni podle vynálezu umožňuje jednoduchým způsobem sledovat průběh reakce, tvorbu vedlejších produktů a hodnotit kvalitu tetrabromdianu·The determination method according to the invention allows for a simple way of monitoring the course of the reaction, the formation of by-products and assessing the quality of tetrabromide.

Přiklad 1 mg tetrabromdianu se silyluje v mikrozkumavce uzavřené propichovací gumovou zátkou 0*25 ml N,O-bis-(trimethyleilyl)-trifluoroacetamidu v kovovém bloku zahřívaném na 80 °C po dobu 30 minut· Na konci silylace se k roztoku přidají 4 kapky chloroformu. Z tohoto roztoku se dávkuje injekční stříkačkou typu Hamilton s kapacitou 10 1 , 0,6 1 do injektoru plynového chromatografu vyhřátého na 280 °C při průtoku nosného plynu dusíku 22 ml/min· Separuje senBkleněné koloně délky 2,40 m a s vnitřním průměrem 2 mm, plněné bílým nosičem zrnění 80 až 100 mesh, smočeným 5 % chlorfenyleilikonového oleje při teplotě 250 °C· ,Example 1 mg of tetrabromide is silylated in a microtube closed with a rubber stopper with 0*25 ml of N,O-bis-(trimethylethyl)-trifluoroacetamide in a metal block heated to 80 °C for 30 minutes. At the end of the silylation, 4 drops of chloroform are added to the solution. From this solution, 0.6 l is dosed with a Hamilton syringe with a capacity of 10 l into the injector of a gas chromatograph heated to 280 °C at a nitrogen carrier gas flow rate of 22 ml/min. It is separated on a glass column 2.40 m long and 2 mm in internal diameter, packed with a white support of 80 to 100 mesh, wetted with 5% chlorophenylethylene oil at a temperature of 250 °C.

265 658265,658

Detekuje ee plamenoionizačnim detektorem, který je vyhřátý na 300 °C. Zastoupeni složek ve vzorku se vyhodnotí z odezev detektoru zpracovaných vyhodnocovacím zařízením přístroje nebo integrátorem.It detects ee with a flame ionization detector, which is heated to 300 °C. The representation of components in the sample is evaluated from the detector responses processed by the instrument's evaluation device or integrator.

Claims (1)

P Ř E ĎM ÍT YYNÁLejřOPLEASE CHANGE YYNAL Způsob kvantitatlvniho stanoveni vedlejSich produktů v tetrabromdianu/vyznačený tim, že se tetrabromdian silyluje silylečnim činidlem, například N,O-bía-(trimethyleilyl)-trifluoroacetamidem a utvořené trimethylsilylethery tetrabromdianu a vedlejších produktů se podrobí plynové chromatografii na náplňové koloně smočené chlorfenylsilikonovým olejem.Method for the quantitative determination of by-products in tetrabromo diane, characterized in that tetrabromo diane is silylated with a silylating agent, for example N, O-bia- (trimethyleilyl) -trifluoroacetamide and the tetrabromo dianum trimethylsilyl ethers formed and the by-products are subjected to gas chromatography on chlorine gas chromatography. Vytiskly Moravské tiskařské závody, středisko 100, Studentská tř.5, OLOMOUCPrinted by Moravian Printing Works, Center 100, Studentská tř.5, OLOMOUC Cena: 2,40 KčsPrice: 2,40 Kčs
CS86704A 1986-01-31 1986-01-31 A method for the quantitative determination of by-products in tetrabromdian CS265658B1 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005085216A1 (en) * 2004-03-05 2005-09-15 Nissan Chemical Industries, Ltd. Isoxazoline-substituted benzamide compound and noxious organism control agent

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005085216A1 (en) * 2004-03-05 2005-09-15 Nissan Chemical Industries, Ltd. Isoxazoline-substituted benzamide compound and noxious organism control agent
EA011764B1 (en) * 2004-03-05 2009-06-30 Ниссан Кемикал Индастриз, Лтд. ISOXAZOLINE-SUBSTITUTED DERIVATIVE BENZAMIDE AND PESTICIDE
US7662972B2 (en) 2004-03-05 2010-02-16 Nissan Chemical Industries, Ltd. Isoxazoline-substituted benzamide compound and pesticide
AU2005219788B2 (en) * 2004-03-05 2010-06-03 Nissan Chemical Corporation Isoxazoline-substituted benzamide compound and noxious organism control agent
EA014881B1 (en) * 2004-03-05 2011-02-28 Ниссан Кемикал Индастриз, Лтд. DERIVATIVES OF SUBSTITUTED ALKYLBENZENE
US8022089B2 (en) 2004-03-05 2011-09-20 Nissan Chemical Industries, Ltd. Isoxazoline-substituted benzamide compound and pesticide
US8138213B2 (en) 2004-03-05 2012-03-20 Nissan Chemical Industries, Ltd. Isoxazoline-substituted benzamide compound and pesticide
US8492311B2 (en) 2004-03-05 2013-07-23 Nissan Chemical Industries, Ltd. Isoxazoline-substituted benzamide compound and pesticide
US10045969B2 (en) 2004-03-05 2018-08-14 Nissan Chemical Industries, Inc. Isoxazoline-substituted benzamide compound and pesticide
US10596157B2 (en) 2004-03-05 2020-03-24 Nissan Chemical Corporation Isoxazoline-substituted benzamide compound and pesticide
US10874645B2 (en) 2004-03-05 2020-12-29 Nissan Chemical Corporation Isoxazoline-substituted benzamide compound and pesticide

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