DE3625205C2 - - Google Patents
Info
- Publication number
- DE3625205C2 DE3625205C2 DE3625205A DE3625205A DE3625205C2 DE 3625205 C2 DE3625205 C2 DE 3625205C2 DE 3625205 A DE3625205 A DE 3625205A DE 3625205 A DE3625205 A DE 3625205A DE 3625205 C2 DE3625205 C2 DE 3625205C2
- Authority
- DE
- Germany
- Prior art keywords
- cyanamide
- naphthoquinone
- sulfonate
- water
- high pressure
- 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.)
- Expired - Lifetime
Links
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- PZTGRDMCBZUJDL-UHFFFAOYSA-N 1,2-naphthoquinone-4-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC(=O)C(=O)C2=C1 PZTGRDMCBZUJDL-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 229940105324 1,2-naphthoquinone Drugs 0.000 claims description 6
- 238000000622 liquid--liquid extraction Methods 0.000 claims description 6
- 238000000638 solvent extraction Methods 0.000 claims description 6
- 239000005909 Kieselgur Substances 0.000 claims description 5
- 239000003463 adsorbent Substances 0.000 claims description 5
- 239000008363 phosphate buffer Substances 0.000 claims description 5
- 150000005621 tetraalkylammonium salts Chemical class 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical class CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 3
- 239000008055 phosphate buffer solution Substances 0.000 claims description 3
- SHFJWMWCIHQNCP-UHFFFAOYSA-M tetrabutylammoniumhydrogensulfate Substances OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- IAGVANYWTGRDOU-UHFFFAOYSA-N 1,4-dioxonaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C(S(=O)(=O)O)=CC(=O)C2=C1 IAGVANYWTGRDOU-UHFFFAOYSA-N 0.000 claims 1
- PKFLXWBXGRAUKU-UHFFFAOYSA-N 3,4-dioxonaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C(=O)C(S(=O)(=O)O)=CC2=C1 PKFLXWBXGRAUKU-UHFFFAOYSA-N 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 239000000284 extract Substances 0.000 claims 1
- 239000002609 medium Substances 0.000 claims 1
- 239000000419 plant extract Substances 0.000 claims 1
- -1 tetraalkylammonium salt Tetrabutylammonium hydrogen sulfate Chemical class 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 241000219094 Vitaceae Species 0.000 description 6
- 235000021021 grapes Nutrition 0.000 description 6
- 239000012071 phase Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 230000002452 interceptive effect Effects 0.000 description 3
- 239000012488 sample solution Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229930192627 Naphthoquinone Natural products 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- 150000002791 naphthoquinones Chemical class 0.000 description 2
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 1
- 150000000181 1,2-naphthoquinones Chemical class 0.000 description 1
- 102100027324 2-hydroxyacyl-CoA lyase 1 Human genes 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 101001009252 Homo sapiens 2-hydroxyacyl-CoA lyase 1 Proteins 0.000 description 1
- XQEZCCYVOHFMNJ-UHFFFAOYSA-N N#CN.[Cl] Chemical group N#CN.[Cl] XQEZCCYVOHFMNJ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- ZIPLUEXSCPLCEI-UHFFFAOYSA-N cyanamide group Chemical group C(#N)[NH-] ZIPLUEXSCPLCEI-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000004190 ion pair chromatography Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- BOVNDVMMYAFMNP-UHFFFAOYSA-N silver cyanamide Chemical compound [Ag+].NC#N BOVNDVMMYAFMNP-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- 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
- G01N33/02—Food
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/17—Nitrogen containing
- Y10T436/172307—Cyanide or isocyanide
Landscapes
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (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)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863625205 DE3625205A1 (de) | 1985-08-22 | 1986-07-25 | Verfahren zur bestimmung von cyanamid in pflanzen oder pflanzenteilen |
| NZ217178A NZ217178A (en) | 1985-08-22 | 1986-08-12 | Determination of cyanamide in plant or plant parts |
| US06/896,950 US4692415A (en) | 1985-08-22 | 1986-08-14 | Process for the determination of cyanamide in plants and plant parts |
| AU61160/86A AU567419B2 (en) | 1985-08-22 | 1986-08-14 | Determination of cyanamide concentrations in plants |
| CA000516549A CA1299474C (en) | 1985-08-22 | 1986-08-21 | Process for the determination of cyanamide in plants and plant parts |
| FR8611995A FR2586480B1 (fr) | 1985-08-22 | 1986-08-22 | Procede pour le dosage du cyanamide dans des vegetaux ou des parties de vegetaux. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3530013 | 1985-08-22 | ||
| DE19863625205 DE3625205A1 (de) | 1985-08-22 | 1986-07-25 | Verfahren zur bestimmung von cyanamid in pflanzen oder pflanzenteilen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3625205A1 DE3625205A1 (de) | 1987-02-26 |
| DE3625205C2 true DE3625205C2 (enExample) | 1990-04-12 |
Family
ID=25835270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19863625205 Granted DE3625205A1 (de) | 1985-08-22 | 1986-07-25 | Verfahren zur bestimmung von cyanamid in pflanzen oder pflanzenteilen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4692415A (enExample) |
| AU (1) | AU567419B2 (enExample) |
| CA (1) | CA1299474C (enExample) |
| DE (1) | DE3625205A1 (enExample) |
| FR (1) | FR2586480B1 (enExample) |
| NZ (1) | NZ217178A (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8702734D0 (en) * | 1987-02-06 | 1987-03-11 | Unilever Plc | Analysis |
| DE3738675C1 (de) * | 1987-11-13 | 1988-12-08 | Sueddeutsche Kalkstickstoff | Verfahren zur Bestimmung von Dicyandiamid in Pflanzen oder Pflanzenteilen |
| US4865991A (en) * | 1987-12-22 | 1989-09-12 | Kraft, Inc. | Methods for partitioning of organic flavor compounds |
| DE3827449A1 (de) * | 1988-08-12 | 1990-02-15 | Sueddeutsche Kalkstickstoff | Verfahren zur analytischen bestimmung von acetylcyanamid |
| US5192690A (en) * | 1988-08-12 | 1993-03-09 | Skw Trostberg Aktiegesellschaft | Process for the analytical determination of acetylcyanamide in urine |
| FR2729469B1 (fr) * | 1995-01-17 | 1997-03-28 | Challenge Agriculture | Procede et composition pour evaluer la teneur d'au moins un composant mineral essentiel pour la croissance d'une plante, utilisation dans le domaine agricole |
| CN104502473B (zh) * | 2014-12-10 | 2016-07-20 | 黄河三角洲京博化工研究院有限公司 | 一种利用hplc法检测单氰胺的定量方法 |
| CN107462646B (zh) * | 2017-08-01 | 2020-04-10 | 山东省烟台市农业科学研究院 | 一种水果中单氰胺残留量的检测方法 |
| CN113466377B (zh) * | 2021-07-16 | 2025-06-20 | 广州国标检验检测有限公司 | 一种药物中氰胺类杂质的检测方法 |
-
1986
- 1986-07-25 DE DE19863625205 patent/DE3625205A1/de active Granted
- 1986-08-12 NZ NZ217178A patent/NZ217178A/xx unknown
- 1986-08-14 AU AU61160/86A patent/AU567419B2/en not_active Ceased
- 1986-08-14 US US06/896,950 patent/US4692415A/en not_active Expired - Fee Related
- 1986-08-21 CA CA000516549A patent/CA1299474C/en not_active Expired - Lifetime
- 1986-08-22 FR FR8611995A patent/FR2586480B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2586480B1 (fr) | 1988-12-23 |
| US4692415A (en) | 1987-09-08 |
| NZ217178A (en) | 1988-08-30 |
| FR2586480A1 (fr) | 1987-02-27 |
| AU6116086A (en) | 1987-02-26 |
| AU567419B2 (en) | 1987-11-19 |
| DE3625205A1 (de) | 1987-02-26 |
| CA1299474C (en) | 1992-04-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |