JP7116819B2 - 1級アミド化合物の検出試薬、検出装置、および検出方法 - Google Patents
1級アミド化合物の検出試薬、検出装置、および検出方法 Download PDFInfo
- Publication number
- JP7116819B2 JP7116819B2 JP2021045858A JP2021045858A JP7116819B2 JP 7116819 B2 JP7116819 B2 JP 7116819B2 JP 2021045858 A JP2021045858 A JP 2021045858A JP 2021045858 A JP2021045858 A JP 2021045858A JP 7116819 B2 JP7116819 B2 JP 7116819B2
- Authority
- JP
- Japan
- Prior art keywords
- sample
- detection reagent
- detection
- primary amide
- product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000001514 detection method Methods 0.000 title claims description 82
- 239000003153 chemical reaction reagent Substances 0.000 title claims description 62
- -1 PRIMARY AMIDE COMPOUND Chemical class 0.000 title claims description 30
- 239000003054 catalyst Substances 0.000 claims description 33
- 239000004480 active ingredient Substances 0.000 claims description 19
- 238000004811 liquid chromatography Methods 0.000 claims description 19
- 238000000926 separation method Methods 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 238000004458 analytical method Methods 0.000 claims description 8
- 229910052697 platinum Inorganic materials 0.000 claims description 8
- 229910052703 rhodium Inorganic materials 0.000 claims description 8
- 229910052707 ruthenium Inorganic materials 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 5
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 2
- 238000002835 absorbance Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 55
- 239000000523 sample Substances 0.000 description 45
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 41
- 239000004202 carbamide Substances 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 238000005259 measurement Methods 0.000 description 7
- 230000014759 maintenance of location Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000008235 industrial water Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 3
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229960001230 asparagine Drugs 0.000 description 3
- 235000009582 asparagine Nutrition 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003575 carbonaceous material Substances 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000001506 fluorescence spectroscopy Methods 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000012360 testing method Methods 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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000000671 immersion lithography Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 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
- 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
-
- 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
-
- 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
- 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
- G01N30/72—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
- G01N30/74—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
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Immunology (AREA)
- Pathology (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Biochemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biophysics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Electrochemistry (AREA)
- Optics & Photonics (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)
Description
本出願は、2020年3月19日に出願された米国特許仮特許出願62/991,714の利益を主張し、その全体が参照されることにより本明細書に組み込まれる。
110…試料ソース
130…混合装置
150…分離装置
170…分析装置
Claims (10)
- 触媒およびキサントヒドロールを反応させることにより形成される検出試薬であって、前記触媒が担体に担持された有効成分を含み、前記有効成分にはPt、Ru、Rh、またはこれらの組み合わせが含まれる、1級アミド化合物の検出試薬。
- 前記担体の粒径d50が3μmから3mmであり、
前記担体の比表面積が7m2/gから1500m2/gである、請求項1に記載の1級アミド化合物の検出試薬。 - 前記有効成分と前記担体との重量比が0.5:99.5から80:20である、請求項1に記載の1級アミド化合物の検出試薬。
- 前記検出試薬が強酸を含まない、請求項1に記載の1級アミド化合物の検出試薬。
- 1級アミド化合物の検出方法であって、
試料を検出試薬に対して準備し、前記試料中の前記1級アミド化合物が前記検出試薬と反応して生成物を形成するようにするステップと、
前記生成物を分離すると共に、前記生成物の性質を検出して、前記試料中の前記1級アミド化合物の濃度を確認するステップと、
を含み、
前記検出試薬は、触媒とキサントヒドロールとを反応させることにより形成されており、前記触媒は担体に担持された有効成分を含み、かつ前記有効成分にはPt、Ru、Rh、またはこれらの組み合わせが含まれる、1級アミド化合物の検出方法。 - 前記検出試薬がカラムに充填され、前記試料が、前記試料の極性と前記検出試薬の極性とが類似したものになるようキサントヒドロールをさらに含む、請求項5に記載の方法。
- 前記生成物を分離する前記ステップが液体クロマトグラフィーを用い、かつ前記生成物の性質を検出する前記ステップが、前記生成物の蛍光信号、分子量、または紫外線吸収信号を検出することを含む、請求項5に記載の方法。
- 検出装置であって、
試料ソースと、
前記試料ソースと接続して試料を受ける混合装置であって、前記試料中の1級アミド化合物と反応して生成物を形成する検出試薬を含む混合装置と、
前記混合装置と接続して前記生成物を分離する分離装置と、
前記分離装置と接続して前記生成物の性質を検出すると共に前記試料中の前記1級アミド化合物の濃度を確認する分析装置と、
を含み、
前記検出試薬が、触媒とキサントヒドロールとを反応させることにより形成され、
前記触媒が担体に担持された有効成分を含み、かつ
前記有効成分にはPt、Ru、Rh、またはこれらの組み合わせが含まれる、検出装置。 - 前記混合装置はカラムであり、前記試料が、前記試料の極性と前記検出試薬の極性とが類似したものになるようキサントヒドロールをさらに含む、請求項8に記載の検出装置。
- 前記分離装置が液体クロマトグラフィーカラムを含み、かつ前記分析装置が、蛍光分光計、質量分析計、または可視光-紫外線吸光度計を含む、請求項8に記載の検出装置。
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 |
---|---|
JP2021177167A JP2021177167A (ja) | 2021-11-11 |
JP7116819B2 true JP7116819B2 (ja) | 2022-08-10 |
Family
ID=77747732
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2021045858A Active JP7116819B2 (ja) | 2020-03-19 | 2021-03-19 | 1級アミド化合物の検出試薬、検出装置、および検出方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US11733219B2 (ja) |
JP (1) | JP7116819B2 (ja) |
KR (1) | KR102526333B1 (ja) |
CN (1) | CN113495064B (ja) |
TW (1) | TWI762246B (ja) |
Citations (4)
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 |
JP2018179545A (ja) | 2017-04-04 | 2018-11-15 | オルガノ株式会社 | 尿素の定量方法及び分析装置 |
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 |
Family Cites Families (20)
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 |
CA2425483C (en) * | 1991-05-22 | 2008-07-29 | Behringwerke Aktiengesellschaft | Assay method utilizing induced luminescence |
ATE208039T1 (de) * | 1991-05-22 | 2001-11-15 | Dade Behring Marburg Gmbh | Bestimmungsmethoden unter verwendung von induzierter lumineszenz |
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 |
US20140121097A1 (en) * | 2012-09-25 | 2014-05-01 | The 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 |
WO2019107045A1 (ja) * | 2017-11-28 | 2019-06-06 | オルガノ株式会社 | 尿素の分析方法及び分析装置 |
-
2021
- 2021-03-19 KR KR1020210036129A patent/KR102526333B1/ko active IP Right Grant
- 2021-03-19 US US17/206,443 patent/US11733219B2/en active Active
- 2021-03-19 TW TW110109939A patent/TWI762246B/zh active
- 2021-03-19 JP JP2021045858A patent/JP7116819B2/ja active Active
- 2021-03-19 CN CN202110305336.9A patent/CN113495064B/zh active Active
Patent Citations (4)
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 |
JP2018179545A (ja) | 2017-04-04 | 2018-11-15 | オルガノ株式会社 | 尿素の定量方法及び分析装置 |
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 |
---|---|
KR20210118368A (ko) | 2021-09-30 |
JP2021177167A (ja) | 2021-11-11 |
KR102526333B1 (ko) | 2023-04-26 |
CN113495064A (zh) | 2021-10-12 |
US11733219B2 (en) | 2023-08-22 |
CN113495064B (zh) | 2024-05-03 |
TW202136775A (zh) | 2021-10-01 |
TWI762246B (zh) | 2022-04-21 |
US20210293765A1 (en) | 2021-09-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5121463B2 (ja) | 芳香族アミン又は脂肪族アミノアルコールの製造方法 | |
US7736612B2 (en) | Processes for production of silica gels carrying derivatization agents for carbonyl compounds | |
JP7116819B2 (ja) | 1級アミド化合物の検出試薬、検出装置、および検出方法 | |
CN113248512A (zh) | 一种检测有机溶剂中痕量水的荧光探针及其制备方法与应用 | |
US20110086429A1 (en) | Methods and devices for detecting ozone and carbonyl-containing compounds | |
George et al. | Poly (N-bromoacrylamide): a new polymeric recyclable oxidizing and brominating reagent | |
CN106546571A (zh) | 一种检测液相中多环芳烃的方法 | |
Hu et al. | Cocatalyst‐Free Reduction of 4, 4′‐Dinitrodiphenyl Ether to 4, 4′‐Diaminodiphenyl Ether Over Twin‐Crystal ZnxCd1− xS under Visible Light | |
Han et al. | Influences of O2 and O3 on the heterogeneous photochemical reaction of NO2 with humic acids | |
CN110560157B (zh) | 氧化铝负载离子液体-钯银双金属催化剂及其制备方法和应用 | |
JP6289916B2 (ja) | 芳香族アミンの製造装置および製造方法 | |
Simonov et al. | Hydrogenation of ethyl p-nitrobenzoate on Pd/Sibunit catalysts | |
JPS58131564A (ja) | 水中の硝酸塩の測定法およびこれに用いる触媒 | |
EP3868712A1 (en) | Ammonia chemical species elimination method using carbon dioxide, ammonia chemical species-supplying agent, and ammonia chemical species adsorption and elimination device | |
Hung | Development of a copper–lanthanum oxide catalyst for the removal of gaseous ammonia by catalytic oxidation: Physicochemical and electrochemical characterization of catalyst materials | |
Pope et al. | The structure and activity of supported metal catalysts: VII. CO poisoning and metal location in palladium-charcoal catalysts | |
CN109503369A (zh) | 一种间苯二甲酸的制备方法 | |
CN108132314B (zh) | 一种环境空气中低级脂肪胺化合物的检测方法 | |
Moskvin et al. | Chromatomembrane Generation of Standard Gas Mixtures Containing Atmospheric Pollutants at a Level of μg/L. | |
CN109369369A (zh) | 间苯二甲酸的制备方法 | |
Kazemimoghadam | Hydrogenation Process Analysis with a Slurry Reactor | |
CN114910433A (zh) | 一种硝基芳香化合物的检测方法 | |
Elbayoumy et al. | Silver Nanoparticles Immobilized on Crosslinked Vinyl Polymer for Catalytic Reduction of Nitrophenol: Experimental and Computational Studies | |
CN116380981A (zh) | 一种气相定量测定亚ppb级污染物的方法 | |
CN114289071A (zh) | 一种耐水脱氧催化剂及其制备方法与应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20210319 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20220426 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20220701 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20220720 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20220729 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7116819 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |