CS267290B1 - Method of diamondide compounds detection - Google Patents
Method of diamondide compounds detection Download PDFInfo
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- CS267290B1 CS267290B1 CS882959A CS295988A CS267290B1 CS 267290 B1 CS267290 B1 CS 267290B1 CS 882959 A CS882959 A CS 882959A CS 295988 A CS295988 A CS 295988A CS 267290 B1 CS267290 B1 CS 267290B1
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- Prior art keywords
- detection
- silica gel
- compounds
- diamondide
- vol
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- 238000001514 detection method Methods 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims abstract description 10
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 11
- 239000000741 silica gel Substances 0.000 claims description 11
- 229910002027 silica gel Inorganic materials 0.000 claims description 11
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000001066 destructive effect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- ZICQBHNGXDOVJF-UHFFFAOYSA-N diamantane Chemical compound C1C2C3CC(C4)CC2C2C4C3CC1C2 ZICQBHNGXDOVJF-UHFFFAOYSA-N 0.000 description 1
- -1 diamantane lactone Chemical class 0.000 description 1
- WOLSPKYGHOUIFM-UHFFFAOYSA-N diamantanone Chemical compound C1C2C3CC(C4)C(=O)C2C2C4C3CC1C2 WOLSPKYGHOUIFM-UHFFFAOYSA-N 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- DIXBSCZRIZDQGC-UHFFFAOYSA-N diaziridine Chemical group C1NN1 DIXBSCZRIZDQGC-UHFFFAOYSA-N 0.000 description 1
- BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical compound O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000011895 specific detection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
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- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
způsob detekce diamantoidních sloučenin, rozdělených tenkovrstvou chromatografii, působením nasyceným etanolickým roztokem eosinu s následnou detekcí UV-lampou.a method for detecting diamondoids thin-layered compounds chromatography, saturated ethanolic solution followed by eosin by UV-lamp detection.
Description
Způsob detekce diamantánů, chromatograficky rozdělených na tenké vrstvě silikagelu.Method for the detection of diamonds, chromatographed on a thin layer of silica gel.
Při separaci diamantoidních sloučenin se analýza reakční směsi provádí nejčastěji plynovou chromatografií, která je značně nákladná, ií semikvantitativnímu rozboru reakčních produktů lze výhodné použít chromatografickou separaci na tenké vrstvě, nejčasteji silikagelu, která je materiálově zcela nenáročná. Závažným problémem je však detekce separovaných sloučenin. Vzhledem k tomu, že sloučeniny typu diamantanu jseu většinou nasycené uhlovodíky pouze s nízkým obsahem heteroutomů, nelze je delegovat UV-svétlem, jako je tomu například v případě sloučenin obsahujících konjugovaný systém dvojných vazen, které jsou schopny zhášet fluorescenci interního fluorochromu přítomného ve vrstvě silikagelu. K vizualizaci nasycených sloučenin, které neobsahují žádno specifické skupiny je třeba použít jiný způsob detekce jako je například nástřik, roztoku kyseliny fosfomolybdenové, manganistanu draselného v kyselině sírové, 68 hmot. % kyselinu sírovou a podonně. Z uvedených možností detekce je zřejmé, že je třeba použít sloučeniny, jejichž aerosoly jsou buá silně leptavé,nebo dokonce jedovaté a při jejich aplikaci dochází k destrukci analyzované sloučeniny. Většinou se jedná o postupy, jejichž použití pro detekci na tenké vrstvě silikagelu pojeného škrobem není příliš vhodné, poněvadž dochází k silné interferenci pojidla.In the separation of diamondoid compounds, the analysis of the reaction mixture is most often carried out by gas chromatography, which is very expensive. However, the detection of separated compounds is a serious problem. Because diamantane-type compounds are mostly saturated hydrocarbons with only a low content of heteroutomes, they cannot be delegated by UV light, as is the case with compounds containing a conjugated double bond system that are capable of quenching the fluorescence of internal fluorochrome present in the silica gel layer. To visualize saturated compounds which do not contain any specific groups, another detection method must be used, such as injection, solution of phosphomolybdic acid, potassium permanganate in sulfuric acid, 68 wt. % sulfuric and podic acid. From the above detection possibilities, it is clear that it is necessary to use compounds whose aerosols are either highly corrosive or even toxic, and their application destroys the analyte. In most cases, these are methods whose use for detection on a thin layer of starch-bonded silica gel is not very suitable because of strong binder interference.
Zmíněné nevýhody podstatně snižuje způsob detekce diamantánů chromatograficky rozdělených na tenké vrstvě silikagelu podle vynálezu. Jeho podstata spočívá v tom, že se na tenkou vrstvu silikagelu s rozděleným vzorkem obsahujícím diamantoidní slouče- 2 267 290 niny působí nasyceným etanolickým roztokem eosinu, s následnou detekcí UV-iampou.The above-mentioned disadvantages are substantially reduced by the method for detecting diamantanes chromatographically separated on a thin layer of silica gel according to the invention. Its essence lies in the fact that a thin layer of silica gel with a divided sample containing diamondoid compounds is treated with a saturated ethanolic solution of eosin, followed by UV detection.
Hlavní výhody způsobu podle vynálezu spočívají v ekonomické nenáročnosti a jednoduchosti. Je to způsob nedestrukční, prováděný s látkami nepovažovanými za toxické. Další výhoda tohoto způsobu detekce je to, že lze v UV-záření fluoreskující skvrny diamantoidních sloučenin z chromátogramu vyškrábat a chromatograficky oddělit od detekčního činidla. Jedná se o způsob nedestruktivní detekce, použitelný jak pro analytické, tak pro preparativní účely. Citlivost/ uvedeného způsobu detekce je 1 a je srovnatelná s běžně používanými detekčními postupy. Detekce podle vynálezu často nebrání ani použití dalšího specifického detekčního či řidla.The main advantages of the method according to the invention lie in the economic simplicity and simplicity. It is a non-destructive method performed with substances not considered toxic. Another advantage of this detection method is that the UV-fluorescent spots of diamondoid compounds can be scraped from the chromatogram and chromatographically separated from the detection reagent. It is a method of non-destructive detection, usable for both analytical and preparative purposes. The sensitivity of the detection method is 1 and is comparable to commonly used detection methods. The detection according to the invention often does not preclude the use of another specific detection or control agent.
Způsob podle vynálezu je dále objasněn na uvedených příkladech.The process according to the invention is further illustrated by the following examples.
Příklad 1Example 1
Ma vrstvu silikagelu o síle 0,05 mm, pojeného škrobem byly aplikovány 2 ml nasyceného roztoku 3-diamantanonu a 3-diamantanlaktonu v eteru. Chromatogram byl vyvinut v komoře obsahující jako mobilní fázi směs hexanu a éteru v poměru 2 obj. : 1 obj. Chromatogram oyl pak nastříknut aerosolem nasyceného roztoku cosinu v etanolu. Po odpaření rozpouštědla byly pod UV-zářením, s vlnovou délkou 366 nm, na chromatogramu zřetelné dvě eranžově fluoreskující skvrny na temně fialovém pozadí s R^, 0,57 charakterizující diamantanon a 0,20 charakterizující diamantanlakton.With a 0.05 mm thick silica gel layer bonded with starch, 2 ml of a saturated solution of 3-diamantanone and 3-diamantanlactone in ether were applied. The chromatogram was developed in a chamber containing as a mobile phase a mixture of hexane and ether in a ratio of 2 vol: 1 vol. The chromatogram was then injected with an aerosol of a saturated solution of cosine in ethanol. After evaporation of the solvent, two orange-fluorescent spots on a dark purple background with Rf, 0.57 characterizing diamantanone and 0.20 characterizing diamantane lactone were visible in the chromatogram under UV light, at a wavelength of 366 nm.
Příklad 2Example 2
Na tenkou vrstvu silikagelu o síle 0,05 mm, pojeného škrobem, bylo naneseno 5 ml chloroformového extraktu reakční směsi obsahující vedle J-diamantandiaziridínu řadu dalších derivátů. Chromatogram byl vyvinut v komoře obsahující jako mobilní fázi směs acetonu a chloroformu v poměru 2 obj. : 3 obj. s 0,7 % obj. trietylaminu. Chromatogram byl pak nastříknut aerosolem nasyceného roztoku eosinu v etanolu. Po odpaření rozpouštědla byly pod5 ml of a chloroform extract of the reaction mixture containing a number of other derivatives in addition to J-diamantanediaziridine were applied to a thin layer of 0.05 mm thick silica gel bonded with starch. The chromatogram was developed in a chamber containing as mobile phase a mixture of acetone and chloroform in a ratio of 2 vol: 3 vol with 0.7% vol by triethylamine. The chromatogram was then sprayed with an aerosol of a saturated solution of eosin in ethanol. After evaporation of the solvent, they were under
- 3 267 290- 3 267 290
UV zářením, 8 vlnovou délkou 366 nm, zřetelné tři oranžově fluoreskující skvrny, z nichž největší, s R^ 0,22, odpovídá diamunLandiuziridínu. Následujícím nástřikem chrómutogromu kyselým etanolickým roztokem jodidu draselného, došlo k reakci jod,idu draselného s diaziridínovou skupinou diamantanu, projevující se tvorbou dooře patrné hnědé skvrny.By UV radiation, 8 at a wavelength of 366 nm, three distinct orange fluorescent spots are evident, the largest of which, with an Rf of 0.22, corresponds to diamunandiuziridine. Subsequent injection of the chromutogrome with an acidic ethanolic solution of potassium iodide resulted in the reaction of potassium iodide with the diaziridine group of diamantane, manifested by the formation of a brown spot.
Příklad 3Example 3
Na preparativní vrstvu silikagelu, silnou 1 mm, bylo naneseno 30 ml nasyceného acetonového roztoku reakční směsi, obsahující 3-diamantanon a 3-diamantandiazirin. Chromatogram byl vyvinut v komoře obsahující jako mobilní fázi směs hexanu a eteru v poměru 5 obj. : 1 obj. Chromatogram byl pak nastříknut aerosolem nasyceného roztoku eosinu a po odpaření rozpouštědla, vyhodnocen pod UV zářením. Fluoreskující zóna obsahující diamantandiazirin s R^ 0,7 byla vyškrábána a separována od detekčního činidla v chromatografické koloně naplněné silikagelem. Mobilní fází hexanu a éteru v poměru 1 obj. : 2 obj. byl diamantandiazirin eluován téměř s čelem rozpouštědla, kdežto eosin zůstává zachycen v koloně.30 ml of a saturated acetone solution of the reaction mixture containing 3-diamantanone and 3-diamantanediazirine were applied to a preparative layer of silica gel, 1 mm thick. The chromatogram was developed in a chamber containing as a mobile phase a mixture of hexane and ether in a ratio of 5 vol: 1 vol. The fluorescent zone containing diamantanediazirine with Rf 0.7 was scraped and separated from the detection reagent in a chromatographic column packed with silica gel. The diamantanediazirine was eluted with the mobile phase of hexane and ether in a ratio of 1 vol: 2 vol. Almost with the front of the solvent, while the eosin remained trapped in the column.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS882959A CS267290B1 (en) | 1988-05-02 | 1988-05-02 | Method of diamondide compounds detection |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS882959A CS267290B1 (en) | 1988-05-02 | 1988-05-02 | Method of diamondide compounds detection |
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| Publication Number | Publication Date |
|---|---|
| CS295988A1 CS295988A1 (en) | 1989-05-12 |
| CS267290B1 true CS267290B1 (en) | 1990-02-12 |
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| CS882959A CS267290B1 (en) | 1988-05-02 | 1988-05-02 | Method of diamondide compounds detection |
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- 1988-05-02 CS CS882959A patent/CS267290B1/en unknown
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| Publication number | Publication date |
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| CS295988A1 (en) | 1989-05-12 |
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