WO1985002679A1 - Process for determining the presence of bis-(2-chlorethyl-sulphide) or bis-(2-chlorethyl-imine) - Google Patents
Process for determining the presence of bis-(2-chlorethyl-sulphide) or bis-(2-chlorethyl-imine) Download PDFInfo
- Publication number
- WO1985002679A1 WO1985002679A1 PCT/EP1984/000383 EP8400383W WO8502679A1 WO 1985002679 A1 WO1985002679 A1 WO 1985002679A1 EP 8400383 W EP8400383 W EP 8400383W WO 8502679 A1 WO8502679 A1 WO 8502679A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- bis
- dye
- chlorethyl
- chloroethyl
- imine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 4
- 230000003595 spectral effect Effects 0.000 claims abstract description 3
- 239000000975 dye Substances 0.000 claims description 15
- 238000001514 detection method Methods 0.000 claims description 8
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 150000002466 imines Chemical class 0.000 claims description 4
- XKTMIJODWOEBKO-UHFFFAOYSA-M Guinee green B Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=CC=CC=2)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 XKTMIJODWOEBKO-UHFFFAOYSA-M 0.000 claims description 3
- NKLPQNGYXWVELD-UHFFFAOYSA-M coomassie brilliant blue Chemical compound [Na+].C1=CC(OCC)=CC=C1NC1=CC=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=C1 NKLPQNGYXWVELD-UHFFFAOYSA-M 0.000 claims description 3
- 235000012701 green S Nutrition 0.000 claims description 3
- WDPIZEKLJKBSOZ-UHFFFAOYSA-M green s Chemical compound [Na+].C1=CC(N(C)C)=CC=C1C(C=1C2=CC=C(C=C2C=C(C=1O)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](C)C)C=C1 WDPIZEKLJKBSOZ-UHFFFAOYSA-M 0.000 claims description 3
- PGSADBUBUOPOJS-UHFFFAOYSA-N neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 239000007850 fluorescent dye Substances 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 239000003086 colorant Substances 0.000 abstract 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical group CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000005284 excitation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000000276 sedentary effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
- G01N31/22—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/0004—Gaseous mixtures, e.g. polluted air
- G01N33/0009—General constructional details of gas analysers, e.g. portable test equipment
- G01N33/0027—General constructional details of gas analysers, e.g. portable test equipment concerning the detector
- G01N33/0036—General constructional details of gas analysers, e.g. portable test equipment concerning the detector specially adapted to detect a particular component
- G01N33/0047—Organic compounds
- G01N33/0049—Halogenated organic compounds
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
Definitions
- the invention relates to a method for the detection of bis- (2-chloroethyl) sulfide or bis- (2-chloroethyl) -imine by adding a chemical reagent to the surface on which the substance to be detected is suspected and optical detection of the radiation formed .
- the bis- (2-chloroethyl) sulfide or -imine is the warfare agent LOST, whose detection on surfaces is usually carried out with indicators that are incorporated in paper or powder. LOST is also detected by gas chromatography after extraction of the surface. Color reactions are also known which take place in aqueous or organic solution. These reactions are carried out in a test tube.
- the present invention is based on the object of developing an easy-to-carry out detection method for the warfare agent LOST.
- a fluorescent dye is used as chemical reagent, which forms an adduct with bis- (2-chloroethyl) sulfide or bis- (2-chloroethyl) imine, which in a different spectral range than the dye is fluorescent.
- a triphenylmethine dye in particular neutral red, guinea green B, lissamine green B or brilliant blue R, is preferably used as the dye.
- all dyes can be used which have a reactive center, which attacks and decomposes LOST nucleophilically or electrophilically, or LOST is bound by adsorption with a change in conformation or incorporated in an inclusion compound. This changes the inherent fluorescence of the dye.
- the excitation wavelength should preferably be in the range between 300 and 400 nm.
- the emission wavelength is preferably 380 to 500 nm.
- Particularly suitable solvents for the dye are water / alcohol, water / acetone or water / dimethylformamide mixtures, or else alcohol, acetone or hexane without the addition of water.
- Triphenylmethine dyes in particular are used as chemical reagents. The invention is illustrated by the following examples.
- Example 1 Neutral red is 10% by weight dissolved in ethanol.
- Example 1 The procedure of Example 1 is repeated, but this time using Guinea Green B as the dye. When excited with light of wavelength 320 nm, the adduct shows a fluorescence at 394 with a relative intensity of 11,700.
- Lissamine Green B is dissolved to 10 -3 wt .-% in 70% water - 30% ethanol. With 5 ⁇ l LOST, an adduct is formed which, when excited with light of wavelength 340 nm, shows fluorescence at 470 nm with a relative intensity of 810.
- Brilliant Blue R is dissolved 2 x 10% by weight in 70% water - 30% ethanol. When excited with light of wavelength 370 nm, the adduct shows fluorescence at 455 nm with a relative intensity of 28 100.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Immunology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Optics & Photonics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biophysics (AREA)
- Combustion & Propulsion (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Luminescent Compositions (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT85900095T ATE37607T1 (de) | 1983-12-10 | 1984-12-01 | Verfahren zum nachweis von bis-(2-chlorethyl)sulfid oder bis-(2-chlorethyl)-imin. |
| FI852970A FI75056C (fi) | 1983-12-10 | 1985-08-01 | Foerfarande foer bevisning av bis-(2-kloretyl)-sulfid eller bis-(2-kloretyl)-imin. |
| NO85853093A NO164383C (no) | 1983-12-10 | 1985-08-06 | Framgangsmaate for paavisning av bis-(2-kloretyl)-sulfid eller bis-(2-kloretyl)-imin. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833344700 DE3344700A1 (de) | 1983-12-10 | 1983-12-10 | Verfahren zum nachweis von bis- (2-chlorethyl)-sulfid oder bis- (2-chlorethyl)-imin |
| DEP3344700.4 | 1983-12-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1985002679A1 true WO1985002679A1 (en) | 1985-06-20 |
Family
ID=6216585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1984/000383 WO1985002679A1 (en) | 1983-12-10 | 1984-12-01 | Process for determining the presence of bis-(2-chlorethyl-sulphide) or bis-(2-chlorethyl-imine) |
Country Status (8)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0326982A3 (de) * | 1988-02-03 | 1991-08-07 | Battelle-Institut e.V. | Verfahren zum Nachweis von Kampfstoffen |
| WO1996010169A1 (en) * | 1994-09-28 | 1996-04-04 | The Secretary Of State For Defence | Detection of sulphur containing compounds |
| WO1996013711A1 (en) * | 1994-10-31 | 1996-05-09 | Minnesota Mining And Manufacturing Company | Ion sensor and a method for producing same |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3844796C2 (en) * | 1988-02-03 | 1993-01-21 | Battelle-Institut E.V., 6000 Frankfurt, De | Chemical warfare agent detection with fluorescent reagent |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH184663A (de) * | 1935-08-07 | 1936-06-15 | Heinrich Dr Draeger Otto | Verfahren zum Nachweisen von Dichlordiäthylsulfid. |
| US3960759A (en) * | 1965-11-24 | 1976-06-01 | The United States Of America As Represented By The Secretary Of The Navy | Liquid vesicant differentiating paint |
| US4083692A (en) * | 1970-06-04 | 1978-04-11 | The United States Of America As Represented By The Secretary Of The Army | Detection and estimation of microquantities of alkylating agents |
| DE2947459A1 (de) * | 1979-11-24 | 1981-05-27 | Battelle-Institut E.V., 6000 Frankfurt | Verfahren und anordnung zum in-situ-nachweis von bodenbelaegen vermuteter giftiger substanzen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE722291C (de) * | 1933-09-28 | 1942-07-07 | Deutsches Reich Vertreten Durc | Verfahren zur Erkennung von Spritzern haftender Kampfstoffe am Erdboden oder an Gegenstaenden |
| JPS5621320A (en) * | 1979-07-28 | 1981-02-27 | Fujitsu Ltd | Manufacture of semiconductor device |
-
1983
- 1983-12-10 DE DE19833344700 patent/DE3344700A1/de active Granted
-
1984
- 1984-11-28 CA CA000468798A patent/CA1231634A/en not_active Expired
- 1984-12-01 AT AT85900095T patent/ATE37607T1/de not_active IP Right Cessation
- 1984-12-01 JP JP60500190A patent/JPS61500687A/ja active Pending
- 1984-12-01 WO PCT/EP1984/000383 patent/WO1985002679A1/de active IP Right Grant
- 1984-12-01 EP EP85900095A patent/EP0164379B1/de not_active Expired
-
1985
- 1985-08-01 FI FI852970A patent/FI75056C/fi not_active IP Right Cessation
- 1985-08-06 NO NO85853093A patent/NO164383C/no unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH184663A (de) * | 1935-08-07 | 1936-06-15 | Heinrich Dr Draeger Otto | Verfahren zum Nachweisen von Dichlordiäthylsulfid. |
| US3960759A (en) * | 1965-11-24 | 1976-06-01 | The United States Of America As Represented By The Secretary Of The Navy | Liquid vesicant differentiating paint |
| US4083692A (en) * | 1970-06-04 | 1978-04-11 | The United States Of America As Represented By The Secretary Of The Army | Detection and estimation of microquantities of alkylating agents |
| DE2947459A1 (de) * | 1979-11-24 | 1981-05-27 | Battelle-Institut E.V., 6000 Frankfurt | Verfahren und anordnung zum in-situ-nachweis von bodenbelaegen vermuteter giftiger substanzen |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0326982A3 (de) * | 1988-02-03 | 1991-08-07 | Battelle-Institut e.V. | Verfahren zum Nachweis von Kampfstoffen |
| WO1996010169A1 (en) * | 1994-09-28 | 1996-04-04 | The Secretary Of State For Defence | Detection of sulphur containing compounds |
| GB2305242A (en) * | 1994-09-28 | 1997-04-02 | Secr Defence | Detection of sulphur containing compounds |
| GB2305242B (en) * | 1994-09-28 | 1998-04-29 | Secr Defence | Detection of sulphur containing compounds |
| US5759861A (en) * | 1994-09-28 | 1998-06-02 | Secretary Of State For Defence In Her Britannic Majesty's Government Of The U.K. Of Gt. Britain & Northern Ireland Of Defence Evaluation & Research Agency | Detection of sulphur containing compounds |
| WO1996013711A1 (en) * | 1994-10-31 | 1996-05-09 | Minnesota Mining And Manufacturing Company | Ion sensor and a method for producing same |
| US5591400A (en) * | 1994-10-31 | 1997-01-07 | Minnesota Mining And Manufacturing Company | Method for producing an ionic sensor |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61500687A (ja) | 1986-04-10 |
| NO853093L (no) | 1985-08-06 |
| NO164383B (no) | 1990-06-18 |
| ATE37607T1 (de) | 1988-10-15 |
| FI75056B (fi) | 1987-12-31 |
| EP0164379B1 (de) | 1988-09-28 |
| FI75056C (fi) | 1988-04-11 |
| DE3344700A1 (de) | 1985-06-20 |
| FI852970A0 (fi) | 1985-08-01 |
| NO164383C (no) | 1990-09-26 |
| DE3344700C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-06-21 |
| CA1231634A (en) | 1988-01-19 |
| FI852970L (fi) | 1985-08-01 |
| EP0164379A1 (de) | 1985-12-18 |
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