TWI762246B - 檢測試劑、檢測裝置、與檢測一級醯胺基化合物的方法 - Google Patents
檢測試劑、檢測裝置、與檢測一級醯胺基化合物的方法 Download PDFInfo
- Publication number
- TWI762246B TWI762246B TW110109939A TW110109939A TWI762246B TW I762246 B TWI762246 B TW I762246B TW 110109939 A TW110109939 A TW 110109939A TW 110109939 A TW110109939 A TW 110109939A TW I762246 B TWI762246 B TW I762246B
- Authority
- TW
- Taiwan
- Prior art keywords
- detection reagent
- sample
- product
- detection
- hydroxydibenzopyran
- Prior art date
Links
- 238000001514 detection method Methods 0.000 title claims abstract description 83
- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract description 63
- -1 primary amide compound Chemical class 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 36
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims abstract description 10
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 9
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 8
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003575 carbonaceous material Substances 0.000 claims abstract description 6
- 229910000019 calcium carbonate Inorganic materials 0.000 claims abstract description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 42
- 239000004202 carbamide Substances 0.000 claims description 42
- COAVOFOBTRTRBB-UHFFFAOYSA-N 6H-benzo[c]chromen-9-ol Chemical compound C1=CC=C2C3=CC(O)=CC=C3COC2=C1 COAVOFOBTRTRBB-UHFFFAOYSA-N 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 21
- 150000003140 primary amides Chemical class 0.000 claims description 21
- 239000004480 active ingredient Substances 0.000 claims description 19
- 238000004811 liquid chromatography Methods 0.000 claims description 18
- 238000002156 mixing Methods 0.000 claims description 14
- 238000000926 separation method Methods 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 6
- 238000004458 analytical method Methods 0.000 claims description 6
- 238000010521 absorption reaction Methods 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 5
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims description 5
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 4
- 238000012360 testing method Methods 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- JFRMYMMIJXLMBB-UHFFFAOYSA-N xanthydrol Chemical compound C1=CC=C2C(O)C3=CC=CC=C3OC2=C1 JFRMYMMIJXLMBB-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 239000007788 liquid Substances 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000005259 measurement Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000008235 industrial water Substances 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 102000004901 Iron regulatory protein 1 Human genes 0.000 description 1
- 108090001025 Iron regulatory protein 1 Proteins 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000000671 immersion lithography Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000012372 quality testing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000008400 supply water Substances 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Images
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
-
- 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
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
-
- 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
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/3103—Atomic absorption analysis
-
- 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
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N23/00—Investigating or analysing materials by the use of wave or particle radiation, e.g. X-rays or neutrons, not covered by groups G01N3/00 – G01N17/00, G01N21/00 or G01N22/00
- G01N23/22—Investigating or analysing materials by the use of wave or particle radiation, e.g. X-rays or neutrons, not covered by groups G01N3/00 – G01N17/00, G01N21/00 or G01N22/00 by measuring secondary emission from the material
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/62—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating the ionisation of gases, e.g. aerosols; by investigating electric discharges, e.g. emission of cathode
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/72—Mass spectrometers
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/72—Mass spectrometers
- G01N30/7233—Mass spectrometers interfaced to liquid or supercritical fluid chromatograph
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G55/00—Compounds of ruthenium, rhodium, palladium, osmium, iridium, or platinum
-
- 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
- G01N2021/6417—Spectrofluorimetric devices
-
- 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
- G01N2021/6417—Spectrofluorimetric devices
- G01N2021/6421—Measuring at two or more wavelengths
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N2030/022—Column chromatography characterised by the kind of separation mechanism
- G01N2030/027—Liquid chromatography
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
- G01N2030/8809—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample
- G01N2030/884—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample 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
- G01N21/6408—Fluorescence; Phosphorescence with measurement of decay time, time resolved fluorescence
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/74—Optical detectors
-
- 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
- G01N33/18—Water
- G01N33/1826—Organic contamination in water
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Electrochemistry (AREA)
- Optics & Photonics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
檢測試劑係由觸媒與9-羥二苯并哌喃反應而成,其中觸媒包括活性成分負載於載體上,活性成分包括Pt、Ru、Rh、或上述之組合,且載體包括碳材、氧化矽、氧化鋁或碳酸鈣。此檢測試劑可用於檢測一級醯胺基化合物。
Description
本揭露關於檢測試劑,更特別關於採用檢測試劑之檢測一級醯胺基化合物的方法與檢測裝置。
因缺水議題及產業用水需求因素,世界各國無不積極開發再生水並逐步導入作為工業用水以降低對民生用水影響。以台灣為例,2021年南部科學工業園區每天將使用再生水達4萬噸以上,以因應南科投資規模逐年擴大,產業用水需求增加區域水庫儲存量長時間入不敷出或缺水所造成之製程停止產能損失。台灣高科技再生水廠依實際產業用水需求規範再生水須符合21項檢測規格方可供水,其中因「尿素」為中性小分子(分子量僅60),使其無法被現有薄膜技術去除,致使尿素成為水質檢測項目中最難檢測與去除的項目。再生水對尿素之規格定義為 5 ppb,因水中尿素濃度若超過5 ppb,將導致使用到浸潤式微影技術之半導體顯影製程產生T-topping效應,使產品製程線寬受影響。因此水中尿素檢測系統之開發,對半導體上下游產業技術發展有其重要性,如供水端的再生水廠、使用純水的半導體級特用化學品、超純水系統商與供應鏈等。
綜上所述,目前亟需新的方法檢測再生水、製程回收水、純水、廢水中的尿素。
本揭露一實施例提供之檢測試劑係由觸媒與9-羥二苯并哌喃反應而成,其中觸媒包括活性成分負載於載體上,活性成分包括Pt、Ru、Rh、或上述之組合。
本揭露一實施例提供之檢測一級醯胺基化合物的方法,包括:提供樣品至檢測試劑,使樣品中的一級醯胺基化合物與檢測試劑反應形成產物;以及分離出產物並分析產物的性質,以確認樣品中的一級醯胺基化合物之濃度,其中檢測試劑係由觸媒與9-羥二苯并哌喃反應而成,其中觸媒包括活性成分負載於載體上,活性成分包括Pt、Ru、Rh、或上述之組合。
本揭露一實施例提供之檢測裝置,包括:樣品源;混合裝置,連接至樣品源以接收樣品,且混合裝置含有檢測試劑以與樣品中的一級醯胺基化合物反應形成產物;分離裝置,連接至混合裝置以分離出產物;以及分析裝置,連接至分離裝置以分析產物的性質,並確認樣品中的一級醯胺基化合物濃度,其中檢測試劑係由觸媒與9-羥二苯并哌喃反應而成,其中觸媒包括活性成分負載於載體上,活性成分包括Pt、Ru、Rh、或上述之組合。
本揭露一實施例提供之檢測試劑,係由觸媒與9-羥二苯并哌喃反應而成。一般而言,9-羥二苯并哌喃的用量遠大於觸媒。舉例來說,可將9-羥二苯并哌喃溶於溶劑以形成溶液,再使溶液與觸媒混合,使觸媒與9-羥二苯并哌喃反應而成檢測試劑。上述的溶劑,舉例來說,包括甲醇、乙醇、異丙醇、其他不與觸媒反應的溶劑,或上述之組合,但不限於此。9-羥二苯并哌喃的結構為。
上述觸媒包括活性成分負載於載體上。舉例來說,活性成分包括Pt、Ru、Rh、或上述之組合,但不限於此,且載體包括碳材、氧化矽、氧化鋁、或碳酸鈣,但不限於此。在一些實施例中,碳材可為不同原料製作而成的活性碳,包括椰殼、Vulcan XC-72、或AC01,但不限於此。在一些實施例中,活性成分可為Pt,而載體可為碳材,如活性碳。在一些實施例中,載體之粒徑為d50
為3 μm至3 mm,例如可為15 μm至80 μm、18 μm、40 μm、或70 μm,但不限於此,且載體之比表面積為7 m2
/g至1500 m2
/g,例如可為100 m2
/g至1200 m2
/g、110 m2
/g、400 m2
/g、或900 m2
/g,但不限於此。若載體之比表面積過小,則觸媒的活性降低,即與9-羥二苯并哌喃反應形成檢測試劑的效果不佳。若載體之比表面積過大,則將導致載體強度降低而易崩解。在一些實施例中,活性成分與載體之重量比為0.5:99.5至80:20,例如可為0.5:99.5、40:60、70.9:29.1、或76.6:23.4,但不限於此。若活性成分的比例過低,則觸媒活性不足。若活性成分的比例過高,反而降低催化效果。在一些實施例中,檢測試劑不含強酸。在這必須說明的是,強酸如HCl、C2
HF3
O2
、HNO3
、H2
SO4
、或其他常見強酸常作為尿素與9-羥二苯并哌喃反應的觸媒,其反應如下:本案形成檢測試劑,以及檢測試劑與尿素的反應如下:可以理解的是,除了尿素以外,上述檢測試劑可與其他一級醯胺基化合物的反應如下:其中R指氫原子或有機基團。與採用強酸作為觸媒的反應相較,本揭露一實施例採用觸媒先與9-羥二苯并哌喃反應形成檢測試劑,再取檢測試劑與一級醯胺基化合物反應形成的產物較穩定。採用強酸作為觸媒的反應產物在一段時間(比如12小時)後即產生大量副產物,而檢測試劑與一級醯胺基化合物反應後的產物可穩定儲存長時間(比如7天)。另一方面,檢測試劑與尿素反應形成產物的時間(低於1分鐘)遠小於尿素與9-羥二苯并哌喃在強酸觸媒下反應的時間(約30分鐘)。
本揭露一實施例提供之檢測一級醯胺基化合物的方法,包括:提供樣品至上述檢測試劑,使樣品中的一級醯胺基化合物與檢測試劑反應形成產物。在一實施例中,一級醯胺基化合物可為尿素。在其他實施例中,一級醯胺基化合物包括尿素、谷氨醯胺、天門冬醯胺或上述之組合,但不限於此。在一些實施例中,樣品含水如處理後再生水、製程回收水、純水或廢水,但不限於此。當一級醯胺基化合物為尿素時,樣品中的尿素偵測極限 (limit of detection;LOD)可達 3 ppb或更低。由於目前台灣再生水的尿素規格為5 ppb,根據本揭露一實施例足以用於確認再生水中的尿素是否符合供水規格。
在一些實施例中,檢測試劑可填充於管柱,而樣品可沖提管柱中的檢測試劑,使樣品中一級醯胺化合物(如尿素)與檢測試劑反應形成產物。由於檢測試劑屬低極性,因此極性的樣品(如純水)中需添加9-羥二苯并哌喃,使樣品的極性近似於檢測試劑的極性,以避免兩者之極性差異過大而無法順利沖提。若樣品為低極性,則可直接加入管柱與低極性的檢測試劑反應。
若是採用上述管柱進行反應,則樣品進入管柱到離開管柱的時間可由管徑大小、管柱長度、樣品流速調整,比如小於1分鐘。上述時間足以讓樣品中的尿素與檢測試劑反應形成產物。若時間過短如沖提速度過快,則尿素反應形成產物的比例過低而難以分析其性質。另一方面,若時間過長如沖提速度過慢,則會延長分析時間而降低檢測效率。
接著分離出產物並檢測產物的性質,以確認樣品中的一級醯胺基化合物之濃度。舉例來說,自管柱流出的液體主要含水(或其他溶劑)、9-羥二苯并哌喃與其衍生物、以及上述產物。由於9-羥二苯并哌喃的比例遠大於產物,因此自管柱流出的液體需先分離後再量測其性質,以避免9-羥二苯并哌喃的訊號覆蓋或干擾產物的訊號。在一些實施例中,分離出產物的步驟採用液相層析法,而分析產物的性質的步驟包括分析產物的螢光強度、分子量、或紫外線吸收強度。在一些實施例中,上述量測可持續150小時而不需更換管柱中的檢測試劑,因此可簡化檢測流程。
在一些實施例中,可直接取樣品與量測試劑混合反應形成產物,而不需將量測試劑填充至管柱中。若是採用此種做法,則須在反應後過濾移除固體如觸媒,再由反應後的混合物(含水或其他溶劑、9-羥二苯并哌喃與其衍生物、以及產物)中分離出產物,並分析產物的性質。由於反應後的產物可穩定存在長時間,因此可存放一段時間後再進行分離與分析,且可保留一部分日後備查。
本揭露一實施例提供檢測裝置100,如圖1所示。檢測裝置100可包括樣品源110以及混合裝置130。混合裝置130連接至樣品源110以接收樣品,且混合裝置130含有上述檢測試劑以與樣品中的一級醯胺基化合物反應形成產物。在一些實施例中,混合裝置130可為管柱以充填檢測試劑。由於檢測試劑一般為低極性,因此樣品源110可添加9-羥二苯并哌喃至樣品中,使樣品的極性接近檢測試劑的極性,以利後續反應形成產物。
檢測裝置100亦可包含分離裝置150,連接至混合裝置130以分離出產物。在一些實施例中,分離裝置130可為液相層析管柱。檢測裝置100亦可包含分析裝置170,連接至分離裝置150以分析產物性質(如螢光強度、分子量、或紫外線吸收強度),並確認樣品中的一級醯胺基化合物濃度。舉例來說,分析裝置170可為螢光光譜儀、質譜儀、或可見光-紫外線吸收光譜儀等。
為讓本揭露之上述內容和其他目的、特徵、和優點能更明顯易懂,下文特舉出較佳實施例,並配合所附圖式,作詳細說明如下:
[實施例]
實施例1
取Pt、Ru、與Rh分別負載於活性碳,以形成觸媒Pt/C (負載量為5%,比表面積為900 m2
/g,Strem Chemicals,Catalog number 78-1611)、Ru/C (負載量為5%,Strem Chemicals,Catalog number 44-4050)、與Rh/C (負載量為5%,Sigma Aldrich,Catalog number 206164)。將上述觸媒分別填充至管柱中後,將9-羥二苯并哌喃與醇類的溶液加入管柱,使觸媒與9-羥二苯并哌喃反應15分鐘,以得檢測試劑。
上述樣品自加入管柱到流出管柱的時間小於1分鐘,可視作尿素與檢測試劑反應所需的時間。接著將管柱流出的液體(主要含水、9-羥二苯并哌喃與其衍生物、以及上述產物)通入液相層析管柱後,以質譜儀量測產物訊號。產物訊號的滯留時間為約5分鐘。如圖2所示,Pt/C、Ru/C、與Rh/C均具有產物訊號,而Pt/C的產物訊號特別明顯。
將自Pt/C管柱流出的液體放置七天後,通入液相層析管柱後,以螢光光譜儀量測產物訊號。上述量測的結果如圖3所示,可知上述與檢測試劑反應後形成的產物可穩定存放長時間,且並無大量副產物產生。如此一來,若液相層析管柱分離及/或螢光光譜儀的排程滿載,產物仍可存放一段時間而不需立刻量測。另一方面,可取一部分管柱流出的液體儲存以待日後備查。
比較例1
將配製好的樣品(含5 ppb的尿素與0.4%(w/v)之9-羥二苯并哌喃溶液)放置30分鐘後,通入液相層析管柱後,以質譜儀量測產物訊號。在滯留時間約5分鐘處無任何產物訊號,如圖2所示。由上述可知,在無觸媒的情況下,尿素與9-羥二苯并哌喃幾乎不反應。
比較例2
配製將配製好的樣品(含5 ppb的尿素與0.4 %(w/v)之9-羥二苯并哌喃溶液)加入1.5M的HCl,通入液相層析管柱後,以質譜儀量測產物訊號。在滯留時間約5分鐘處有少量產物訊號。
將配製好的樣品(含5 ppb的尿素與0.4 %(w/v)之9-羥二苯并哌喃溶液)加入1.5M的HCl,反應30分鐘後通入液相層析管柱後,以質譜儀量測產物訊號。在約5分鐘處有大量產物訊號,如圖2所示。由上述可知,尿素與9-羥二苯并哌喃在HCl觸媒下反應形成產物所需的反應高達30分鐘,遠大於本揭露一實施例之檢測試劑與尿素反應所需的時間。
將樣品與HCl反應30分鐘後的產物放置12小時後,通入液相層析管柱後,以螢光光譜儀量測產物訊號。上述量測的結果如圖4所示,可知尿素與9-羥二苯并哌喃在HCl觸媒下反應後在短時間後即產生大量副產物(滯留時間約17.5分鐘)。如此一來,上述反應後須即時量測而無法儲存長時間。
實施例2
與實施例1的檢測試劑(採用Pt/C觸媒)與樣品類似,差別在於持續通入樣品至管柱150小時。將管柱流出的液體(主要含水、9-羥二苯并哌喃與其衍生物、以及上述產物)通入液相層析管柱後,以螢光光譜儀量測約2分鐘的訊號積分值,如圖5所示。由圖5可知,上述系統持續量測的時間可高達150小時。
實施例3
與實施例1的檢測試劑(採用Pt/C觸媒)類似,差別在不同時間分別通入含3 ppb、5 ppb、7 ppb、5 ppb、與3 ppb的尿素之水溶液樣品(均含0.4 %(w/v)的9-羥二苯并哌喃)。將管柱流出的液體(主要含水、9-羥二苯并哌喃與其衍生物、以及上述產物)通入液相層析管柱後,以螢光光譜儀量測約2分鐘的訊號積分值,如圖6所示。由圖6可知,上述檢測系統可分辨樣品中0 ppb至7 ppb的尿素濃度差異。
實施例4
取Pt負載於活性碳(比表面積為900 m2
/g,Strem Chemicals,Catalog number 78-1611)上,以形成Pt/C (負載量為5%)。將6 mg之Pt/C、3 mL的9-羥二苯并哌喃及3 mL配製好的樣品(含33 ppm的尿素、谷氨醯胺、天門冬醯胺水溶液與0.4 %(w/v)之9-羥二苯并哌喃溶液)反應30分鐘,使樣品中的一級醯胺基化合物與檢測試劑反應以形成產物如下:
將反應後的混合物過濾或離心移除固體(如觸媒)後,將液體(主要含水、9-羥二苯并哌喃與其衍生物、以及上述產物)通入液相層析管柱,並以螢光光譜儀量測產物訊號。產物訊號的遲滯時間依序為天門冬醯胺約1.4分鐘、谷氨醯胺約1.6分鐘、尿素約2.0分鐘。由上述可知,檢測試劑亦可用於檢測尿素以外的其他一級醯胺基化合物。
雖然本揭露已以數個較佳實施例揭露如上,然其並非用以限定本揭露,任何所屬技術領域中具有通常知識者,在不脫離本揭露之精神和範圍內,當可作任意之更動與潤飾,因此本揭露之保護範圍當視後附之申請專利範圍所界定者為準。
100:檢測裝置
110:樣品源
130:混合裝置
150:分離裝置
170:分析裝置
圖1係一實施例中,檢測裝置的示意圖。
圖2係一實施例中,含尿素之樣品與不同檢測試劑反應後,經液相層析管柱分離後以質譜儀量測的液相層析圖。
圖3係一實施例中,含尿素之樣品與檢測試劑反應且放置7天之前與之後,經液相層析管柱分離後以螢光光譜儀量測的液相層析圖。
圖4係一實施例中,含尿素之樣品與9-羥二苯并哌喃在HCl觸媒下反應且放置12小時之前與之後,經液相層析管柱分離後以螢光光譜儀量測的液相層析圖。
圖5係一實施例中,將含尿素之樣品連續通入檢測試劑150小時後,經液相層析管柱分離後量測的訊號積分面積。
圖6係一實施例中,將含不同濃度的尿素之樣品通入檢測試劑後,經液相層析管柱分離後量測的訊號積分面積。
100:檢測裝置
110:樣品源
130:混合裝置
150:分離裝置
170:分析裝置
Claims (15)
- 一種檢測試劑,係由一觸媒與9-羥二苯并哌喃反應而成,其中該觸媒包括一活性成分負載於一載體上,該活性成分包括Pt、Ru、Rh、或上述之組合。
- 如請求項1之檢測試劑,其中該載體包括碳材、氧化矽、氧化鋁、或碳酸鈣。
- 如請求項1之檢測試劑,其中該載體之粒徑d50 為3 μm至3 mm,且該載體之比表面積為7 m2 /g至1500 m2 /g。
- 如請求項1之檢測試劑,其中該活性成分與該載體之重量比為0.5:99.5至80:20。
- 如請求項1之檢測試劑,其中該檢測試劑不含強酸。
- 一種檢測一級醯胺基化合物的方法,包括: 提供一樣品至一檢測試劑,使該樣品中的一級醯胺基化合物與該檢測試劑反應形成一產物;以及 分離該產物並檢測該產物的性質,以確認該樣品中的該一級醯胺基化合物之濃度, 其中該檢測試劑係由一觸媒與9-羥二苯并哌喃反應而成,其中該觸媒包括一活性成分負載於一載體上,該活性成分包括Pt、Ru、Rh、或上述之組合。
- 如請求項6之檢測一級醯胺基化合物的方法,其中該載體包括碳材、氧化矽、氧化鋁、或碳酸鈣。
- 如請求項6之檢測一級醯胺基化合物的方法,其中該檢測試劑填充於一管柱中,且該樣品更包含9-羥二苯并哌喃,使該樣品的極性近似於該檢測試劑的極性。
- 如請求項6之檢測一級醯胺基化合物的方法,其中分離該產物的步驟採用液相層析法,而檢測該產物的性質的步驟包括檢測該產物的螢光訊號、分子量、或紫外線吸收訊號。
- 如請求項6之檢測一級醯胺基化合物的方法,其中該一級醯胺基化合物包括尿素、谷氨醯胺、天門冬醯胺、或上述之組合。
- 一種檢測裝置,包括: 一樣品源; 一混合裝置,連接至該樣品源以接收一樣品,且該混合裝置含有一檢測試劑以與該樣品中的一級醯胺基化合物反應形成一產物; 一分離裝置,連接至該混合裝置以分離出該產物;以及 一分析裝置,連接至該分離裝置以檢測該產物的性質,並確認該樣品中的一級醯胺基化合物濃度, 其中該檢測試劑係由一觸媒與9-羥二苯并哌喃反應而成, 其中該觸媒包括一活性成分負載於一載體上,該活性成分包括Pt、Ru、Rh、或上述之組合。
- 如請求項11之檢測裝置,其中該載體包括碳材、氧化矽、氧化鋁、或碳酸鈣。
- 如請求項11之檢測裝置,其中該混合裝置係一管柱,且該樣品更包含9-羥二苯并哌喃,使該樣品的極性近似於該檢測試劑的極性。
- 如請求項11之檢測裝置,其中該分離裝置包括液相層析管柱,而該分析裝置可包括螢光光譜儀、質譜儀、或可見光-紫外線吸收光譜儀。
- 如請求項11之檢測裝置,其中該一級醯胺基化合物包括尿素、谷氨醯胺、天門冬醯胺、或上述之組合。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US202062991714P | 2020-03-19 | 2020-03-19 | |
US62/991,714 | 2020-03-19 |
Publications (2)
Publication Number | Publication Date |
---|---|
TW202136775A TW202136775A (zh) | 2021-10-01 |
TWI762246B true TWI762246B (zh) | 2022-04-21 |
Family
ID=77747732
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW110109939A TWI762246B (zh) | 2020-03-19 | 2021-03-19 | 檢測試劑、檢測裝置、與檢測一級醯胺基化合物的方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US11733219B2 (zh) |
JP (1) | JP7116819B2 (zh) |
KR (1) | KR102526333B1 (zh) |
CN (1) | CN113495064B (zh) |
TW (1) | TWI762246B (zh) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106885905A (zh) * | 2015-12-16 | 2017-06-23 | 山东博科生物产业有限公司 | 一种具有优越检测线和分析灵敏度的尿素检测试剂及检测方法 |
CN107703124A (zh) * | 2016-08-08 | 2018-02-16 | 安恒环境科技(北京)股份有限公司 | 尿素浓度检测方法及尿素浓度在线监测设备 |
TW201842333A (zh) * | 2017-04-04 | 2018-12-01 | 日商奧璐佳瑙股份有限公司 | 尿素之定量方法及分析裝置 |
CN109406424A (zh) * | 2018-11-12 | 2019-03-01 | 上海仪电科学仪器股份有限公司 | 用于检测水中尿素浓度的检测剂及其制备方法和检测方法 |
TW201934998A (zh) * | 2017-11-28 | 2019-09-01 | 日商奧璐佳瑙股份有限公司 | 尿素之分析方法及分析裝置 |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2891957A (en) * | 1958-02-21 | 1959-06-23 | Wm S Merrell Co | Amino alkoxy phenyl methanes |
US3157658A (en) * | 1963-07-05 | 1964-11-17 | Searle & Co | 1-carbalkoxy-4-(9-xanthenyl) piperazines and related compounds |
US4813973A (en) * | 1988-01-11 | 1989-03-21 | The University Of Toronto Innovations Foundation | Modified, water-soluble polymers containing amide groups reacted with xanthydrol and other dyes |
EP0984281B1 (en) * | 1991-05-22 | 2007-01-03 | Dade Behring Marburg GmbH | A homogeneous assay for determining analyte |
CA2425483C (en) * | 1991-05-22 | 2008-07-29 | Behringwerke Aktiengesellschaft | Assay method utilizing induced luminescence |
JPH0610147A (ja) * | 1992-06-25 | 1994-01-18 | Hitachi Ltd | パラジウム活性化液 |
JP3775179B2 (ja) * | 1999-08-05 | 2006-05-17 | 住友化学株式会社 | 担持酸化ルテニウム触媒の製造方法及び塩素の製造方法 |
JP5552977B2 (ja) * | 2010-09-10 | 2014-07-16 | 栗田工業株式会社 | 溶存物質濃度の測定方法 |
CN102353728B (zh) * | 2011-06-29 | 2013-03-27 | 中国食品发酵工业研究院 | 一种黄酒生产过程质量控制快速检测方法 |
WO2014052275A1 (en) * | 2012-09-25 | 2014-04-03 | Materials Foundry, Llc | Catalysts by concurrent creation of support and metal (3c-sam) |
CN102928530A (zh) * | 2012-10-15 | 2013-02-13 | 谱尼测试科技股份有限公司 | 一种高效液相色谱法测定豆芽中尿素残留量的检测方法 |
CN103063762A (zh) * | 2012-12-21 | 2013-04-24 | 青岛谱尼测试有限公司 | 一种高效液相色谱法测定西瓜中瓜氨酸含量的方法 |
CN103487529A (zh) * | 2013-10-15 | 2014-01-01 | 谱尼测试科技(天津)有限公司 | 一种高效液相色谱法测定面粉及面制品中氨基脲残留量的方法 |
CN103760266A (zh) * | 2014-01-16 | 2014-04-30 | 深圳市华测检测技术股份有限公司 | 一种用高效液相色谱法检测发酵酒中尿素含量的方法 |
CN103954722A (zh) | 2014-05-21 | 2014-07-30 | 江南大学 | 一种针对白酒中的微量尿素的检测方法 |
CN104678007A (zh) * | 2014-12-19 | 2015-06-03 | 谱尼测试科技股份有限公司 | 一种测定面制品中联二脲残留量的方法 |
CN105316390A (zh) * | 2015-11-25 | 2016-02-10 | 江南大学 | 一种高通量筛选尿素高效利用菌株的方法 |
US10253285B2 (en) | 2016-10-26 | 2019-04-09 | Jiangnan University | Method for simultaneously reducing urethane and its precursors levels during Chinese liquor production process |
CN106680361B (zh) * | 2017-03-28 | 2023-05-12 | 中国科学院上海有机化学研究所 | 一种温度可调控的敞开式火焰离子化装置 |
-
2021
- 2021-03-19 US US17/206,443 patent/US11733219B2/en active Active
- 2021-03-19 TW TW110109939A patent/TWI762246B/zh active
- 2021-03-19 KR KR1020210036129A patent/KR102526333B1/ko active IP Right Grant
- 2021-03-19 CN CN202110305336.9A patent/CN113495064B/zh active Active
- 2021-03-19 JP JP2021045858A patent/JP7116819B2/ja active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106885905A (zh) * | 2015-12-16 | 2017-06-23 | 山东博科生物产业有限公司 | 一种具有优越检测线和分析灵敏度的尿素检测试剂及检测方法 |
CN107703124A (zh) * | 2016-08-08 | 2018-02-16 | 安恒环境科技(北京)股份有限公司 | 尿素浓度检测方法及尿素浓度在线监测设备 |
TW201842333A (zh) * | 2017-04-04 | 2018-12-01 | 日商奧璐佳瑙股份有限公司 | 尿素之定量方法及分析裝置 |
TW201934998A (zh) * | 2017-11-28 | 2019-09-01 | 日商奧璐佳瑙股份有限公司 | 尿素之分析方法及分析裝置 |
CN109406424A (zh) * | 2018-11-12 | 2019-03-01 | 上海仪电科学仪器股份有限公司 | 用于检测水中尿素浓度的检测剂及其制备方法和检测方法 |
Also Published As
Publication number | Publication date |
---|---|
KR102526333B1 (ko) | 2023-04-26 |
TW202136775A (zh) | 2021-10-01 |
JP7116819B2 (ja) | 2022-08-10 |
CN113495064A (zh) | 2021-10-12 |
US11733219B2 (en) | 2023-08-22 |
US20210293765A1 (en) | 2021-09-23 |
KR20210118368A (ko) | 2021-09-30 |
JP2021177167A (ja) | 2021-11-11 |
CN113495064B (zh) | 2024-05-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KopyŚĆ et al. | Determination of mercury by cold-vapor atomic absorption spectrometry with preconcentration on a gold-trap | |
EP0192587A1 (fr) | Procédé d'hydrogénation de l'acide acétique | |
CN101726548B (zh) | 水样中硝基苯胺类污染物的固相萃取与hplc-紫外检测方法 | |
Qin et al. | Chemiluminescence flow system for the determination of Fe (II) and Fe (III) in water | |
US7736612B2 (en) | Processes for production of silica gels carrying derivatization agents for carbonyl compounds | |
Baxter et al. | Critical comparison of two standard digestion procedures for the determination of total mercury in natural water samples by cold vapour atomic absorption spectrometry | |
TWI762246B (zh) | 檢測試劑、檢測裝置、與檢測一級醯胺基化合物的方法 | |
Parmar et al. | Laboratory tests of KI and alkaline annular denuders | |
US20110086429A1 (en) | Methods and devices for detecting ozone and carbonyl-containing compounds | |
CN108414637B (zh) | 一种利用固相微萃取-气相色谱-质谱联用技术检测水中挥发性消毒副产物的方法 | |
JP4403745B2 (ja) | ディーゼル粒子中のニトロ多環芳香族炭化水素の分析装置と分析方法 | |
CN113087651A (zh) | 一种含有吲哚基团的化合物及其制备方法和应用 | |
CN107677765B (zh) | 一种基于toc衍生催化燃烧法测定羟胺盐有机残留的方法 | |
Gemuh et al. | Solvent-assisted dispersive micro-solid phase extraction of bisphenols using iron (III) thenoyltrifluoroacetonate complex (Fe (TTA) 3) as a new nanostructured sorbent: a proof of concept | |
Abdulla et al. | Spectrophotometric Determination of Cerium in Some Ore in Kurdistan Region–Iraq | |
US9447008B2 (en) | Acetone production using silicon nanoparticles and catalyst compositions | |
CN108132314B (zh) | 一种环境空气中低级脂肪胺化合物的检测方法 | |
CN116380981B (zh) | 一种气相定量测定亚ppb级污染物的方法 | |
CN112098575B (zh) | 一种液相色谱检测胶黏剂中1,3-双(1-异氰酸根-1-甲基乙基)苯的方法 | |
CN109503369A (zh) | 一种间苯二甲酸的制备方法 | |
CN113777192B (zh) | 一种涂料制品中丙烯酰胺的测定方法 | |
EP3868712A1 (en) | Ammonia chemical species elimination method using carbon dioxide, ammonia chemical species-supplying agent, and ammonia chemical species adsorption and elimination device | |
CN114289071A (zh) | 一种耐水脱氧催化剂及其制备方法与应用 | |
CN117568028A (zh) | 基于七元瓜环的氮硫共掺杂碳点荧光探针及其制备和应用 | |
Moskvin et al. | Chromatomembrane Generation of Standard Gas Mixtures Containing Atmospheric Pollutants at a Level of μg/L. |