CN108395730B - Synthesis method of 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine - Google Patents
Synthesis method of 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine Download PDFInfo
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- CN108395730B CN108395730B CN201810229012.XA CN201810229012A CN108395730B CN 108395730 B CN108395730 B CN 108395730B CN 201810229012 A CN201810229012 A CN 201810229012A CN 108395730 B CN108395730 B CN 108395730B
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- WLNTVTDTBKPTCA-UHFFFAOYSA-N 4-[(5-chloropyridin-2-yl)diazenyl]benzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1N=NC1=CC=C(Cl)C=N1 WLNTVTDTBKPTCA-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000001308 synthesis method Methods 0.000 title claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000012065 filter cake Substances 0.000 claims abstract description 19
- 239000013078 crystal Substances 0.000 claims abstract description 18
- 239000012954 diazonium Substances 0.000 claims abstract description 17
- 150000001989 diazonium salts Chemical class 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000243 solution Substances 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 9
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 claims abstract description 8
- VEGZHURRCWERMK-UHFFFAOYSA-N benzene-1,3-diamine;hydrochloride Chemical compound Cl.NC1=CC=CC(N)=C1 VEGZHURRCWERMK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000011259 mixed solution Substances 0.000 claims abstract description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims abstract description 6
- 239000001632 sodium acetate Substances 0.000 claims abstract description 6
- 235000017281 sodium acetate Nutrition 0.000 claims abstract description 6
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000007787 solid Substances 0.000 claims abstract description 5
- 238000000967 suction filtration Methods 0.000 claims description 21
- 238000001816 cooling Methods 0.000 claims description 17
- 238000005406 washing Methods 0.000 claims description 17
- 238000010992 reflux Methods 0.000 claims description 14
- 239000000725 suspension Substances 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 7
- 239000011521 glass Substances 0.000 claims description 6
- 239000005457 ice water Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000004537 pulping Methods 0.000 claims description 4
- -1 2.34mol Chemical compound 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 238000004128 high performance liquid chromatography Methods 0.000 abstract description 7
- 239000000047 product Substances 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 abstract description 2
- 239000000975 dye Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 238000004737 colorimetric analysis Methods 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000007864 suspending Methods 0.000 description 2
- 230000032683 aging Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000008641 benzimidazolones Chemical class 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 150000005125 dioxazines Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
- C09B29/0048—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a six-membered heterocyclic ring with one nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses a synthesis method of 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine, which is characterized in that 2-amino-5-chloropyridine is added into an ethanol solution of sodium amide and is matured after being added, isoamyl nitrite is added into a reaction solution and is matured after being added, the reaction solution is cooled and filtered to obtain diazonium salt, the diazonium salt is pulped and suspended by ethyl acetate and is washed, the diazonium salt is added into the ethanol and is dropwise added with a mixed solution of m-phenylenediamine hydrochloride, sodium acetate and water, the mixture is matured after being added to obtain red crystals, the red crystals are cooled and filtered, filter cakes are suspended and washed by water, the filter cakes after being suspended and washed are dissolved by the ethanol, filtered and concentrated, potassium hydroxide solution is added for treatment, and the solid obtained after the filtration is finally suspended and washed by hot water to obtain a high-purity product, wherein the HPLC purity of the 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine prepared by the invention can reach more than 99 percent, and the total yield is more than 80 percent.
Description
Technical Field
The invention relates to a synthesis method of 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine, belonging to the technical field of synthesis of novel organic azo dyes and heavy metal colorimetric analysis researches.
Background
The current domestic research compares organic dyes including coumarin dyes, polyene dyes, thiophene dyes, porphyrin dyes, triphenylamine dyes and the like, and the newly emerging new varieties of organic dyes also include DPP dyes, benzimidazolones, dioxazines, condensed azo dyes and the like.
The 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine developed by the invention also belongs to a novel condensed azo organic dye, can be used for colorimetric analysis of heavy metals such as cobalt and cadmium, and has very high application value, so the method has very research value for synthesis of a novel organic dye compound 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine.
Disclosure of Invention
The invention provides process methods for synthesizing 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine, which have the advantages of low cost, high yield, simple purification process and convenient operation and are suitable for industrial production.
In order to solve the above problems, the present invention provides a method for synthesizing kinds of 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine, which is characterized by comprising the following steps:
step 1): adding 2-amino-5-chloropyridine into the ethanol solution of the sodium amide, and aging after the addition;
step 2): dripping isoamyl nitrite into the reaction solution obtained in the step 1), and curing after dripping;
step 3): cooling and filtering the reaction solution obtained in the step 2) to obtain diazonium salt, pulping and washing with ethyl acetate;
step 4): adding the diazonium salt obtained in the step 3) into ethanol, then dropwise adding a mixed solution of m-phenylenediamine hydrochloride, sodium acetate and water, and curing after dropwise adding to obtain a red crystal;
step 5): cooling and suction-filtering the red crystal obtained in the step 4), washing the filter cake in water, adding ethanol into the filter cake after suspension-washing for dissolving, filtering and concentrating, adding a potassium hydroxide solution for processing, and finally washing the solid obtained by suction-filtering in hot water to obtain a high-purity product.
Preferably, 2-amino-5-chloropyridine is added at the temperature of 0-5 ℃ in the step 1), and after the addition is finished, the mixture is refluxed for 1-2 hours and is aged; the molar ratio of the 2-amino-5-chloropyridine to the sodium amide is 1: 1.2-1.5.
Preferably, the step 2) is specifically: dripping isoamyl nitrite into the reaction solution obtained in the step 1) at the temperature of 65-70 ℃, and refluxing for 2-3 hours after dripping; wherein the molar ratio of the 2-amino-5-chloropyridine to the isoamyl nitrite is 1: 1.1-1.5.
Preferably, the step 3) is specifically: cooling the reaction liquid obtained in the step 2) to 0-5 ℃, standing for 3-4 hours, carrying out suction filtration, then carrying out suspension washing on the filter cake with ethyl acetate, removing impurities, and drying to obtain the intermediate diazonium salt.
Preferably, the step 4) is specifically: adding the diazonium salt obtained in the step 3) into ethanol, cooling to 0-5 ℃, dripping the mixed solution, and preserving heat for 2-3 hours to mature after dripping; wherein the mol ratio of the 2-amino-5-chloropyridine to the m-phenylenediamine hydrochloride to the sodium acetate is 1: 1.1-1.5.
Preferably, the step 5) is specifically: and (3) suspending and washing the red crystal obtained in the step 4) with water, heating and dissolving the filter cake with ethanol, filtering, concentrating the filtrate to remove 1/2, adding 10% potassium hydroxide solution, refluxing for 2 hours, cooling, standing at 0-5 ℃ for 3 hours, performing suction filtration, suspending and washing the filter cake with 70-80 ℃ water, performing suction filtration, and drying to obtain the 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine yellow red crystal.
The invention adopts 2-amino-5-chloropyridine, isoamyl nitrite and m-phenylenediamine hydrochloride which are easily obtained industrially as main raw materials and ethanol as an organic solvent, and the target product crude product is obtained by two-step synthesis, and then the high-purity product 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine is obtained by ethanol recrystallization and hydrothermal suspension washing in sequence, wherein the HPLC purity is more than 99 percent, and the total yield is more than 80 percent.
Compared with the prior art, the invention has the following beneficial effects:
1. the synthetic raw materials adopted by the invention are cheap and easily available, are all industrial products, have mild reaction conditions, are convenient to operate, are easy to control the reaction, have simple requirements on reaction equipment, and are suitable for industrial production;
2. the method synthesizes the 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine by 2 steps, the reaction temperature and the material dosage ratio of each step are controlled, the intermediate diazonium salt is thermally suspended by ethyl acetate to remove impurities, the crude product is thermally suspended by ethanol to remove impurities, the crude product is purified to obtain a high-purity product, the HPLC purity reaches more than 99 percent, and the total yield is more than 80 percent.
Detailed Description
In order to make the invention more comprehensible, preferred embodiments are described in detail below.
Examples
process methods for synthesizing 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine:
the chemical equation of the synthesis process of the invention is as follows:
the specific implementation steps are as follows:
(1) preparing a 10L glass reaction kettle, sequentially adding 3L of ethanol and sodium amide (78g, 2.0mol), cooling to 0-5 ℃ in an ice water bath, slowly adding 2-amino-5-chloropyridine (200g, 1.56mol), and refluxing for 2 hours after the addition;
(2) dripping isoamyl nitrite (220g, 1.87mol) at 65-70 ℃, and refluxing for 2-3 hours after dripping;
(3) after the reaction is finished, cooling the reaction solution to 0-5 ℃, standing for 4 hours to generate a large amount of yellow solid, performing suction filtration to obtain 560G of intermediate diazonium salt with wet weight, pulping and washing with 5L ethyl acetate, performing suction filtration, and drying to obtain 356G of yellow crystal diazonium salt;
(4) preparing a 10L glass reaction kettle, sequentially adding 4.5L of ethanol and intermediate diazonium salt (356g) to be in a suspension state, cooling to 0-5 ℃ in an ice water bath, slowly dropwise adding a mixed solution (280g of 1.56mol of m-phenylenediamine hydrochloride, 2L of water and 168g of 2.05mol of sodium acetate), and after dropwise adding, continuing to perform heat preservation reaction at 0-5 ℃ for 3 hours, wherein a large amount of red crystals appear;
(5) carrying out suction filtration on red crystals precipitated by the reaction, and then carrying out suspension washing on a filter cake by using 2L of water, and carrying out suction filtration to obtain 560g of a wet heavy filter cake; and then adding the filter cake into 5L of ethanol, heating and refluxing for 1-2 hours, filtering, concentrating the filtrate to 1/2, adding 6L of 10% potassium hydroxide solution into the filtrate, refluxing for 2 hours, cooling to 0-5 ℃, keeping the temperature and standing for 3 hours, performing suction filtration, performing suspension washing on the filter cake with 2L of 80 ℃ water, performing suction filtration, and drying to obtain 310g of yellow-red crystal 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine.
The nuclear magnetic resonance processing data, HPLC and MP of the prepared compound are detected as follows:
1H-NMR(DMSO，400MHz，δppm)：δ＝5.8(1H，s)，6.02(1H，d)，6.29(2H，brs)，7.31(1H，d)，7.66(1H，d)，7.81(1H，d)，8.45(1H，s)
HPLC：99.6％
MP：254℃
from the above data, it was found that the compound obtained above was 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine, and the total yield was 80.7%. The storage conditions are as follows: and (3) filling argon at a low temperature of 0-5 ℃.
The specific implementation II comprises the following steps:
(1) preparing a 10L glass reaction kettle, sequentially adding 3L of ethanol and sodium amide (93.6g, 2.34mol), cooling to 0-5 ℃ in an ice water bath, slowly adding 2-amino-5-chloropyridine (200g, 1.56mol), and refluxing for 2 hours after the addition;
(2) dripping isoamyl nitrite (275g, 2.34mol) at the temperature of 65-70 ℃, and refluxing for 2-3 hours after dripping;
(3) after the reaction is finished, cooling the reaction solution to 0-5 ℃, standing for 4 hours to generate a large amount of yellow solid, performing suction filtration to obtain 575g of intermediate diazonium salt with wet weight, pulping and washing with 5L of ethyl acetate, performing suction filtration, and drying to obtain 364g of diazonium salt as yellow crystals;
(4) preparing a 10L glass reaction kettle, sequentially adding 4.5L of ethanol and intermediate diazonium salt (364g) to be in a suspension state, cooling to 0-5 ℃ in an ice-water bath, slowly dropwise adding a mixed solution (280g of 1.56mol of m-phenylenediamine hydrochloride, 2L of water and 192g of 2.34mol of sodium acetate), and after dropwise adding, continuously carrying out heat preservation reaction at 0-5 ℃ for 3 hours, wherein a large amount of red crystals appear;
(5) carrying out suction filtration on red crystals precipitated by the reaction, and then carrying out suspension washing on a filter cake by using 2L of water, and carrying out suction filtration to obtain 574g of wet heavy filter cake; and then adding the filter cake into 5L of ethanol, heating and refluxing for 1-2 hours, filtering, concentrating the filtrate to 1/2, adding 6L of 10% potassium hydroxide solution into the filtrate, refluxing for 2 hours, cooling to 0-5 ℃, keeping the temperature and standing for 3 hours, performing suction filtration, performing suspension washing on the filter cake with 2L of 80 ℃ water, performing suction filtration, and drying to obtain 322g of yellowish red crystal 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine.
The nuclear magnetic resonance processing data, HPLC and MP of the prepared compound are detected as follows:
1H-NMR(DMSO，400MHz，δppm)：δ＝5.8(1H，s)，6.02(1H，d)，6.29(2H，brs)，7.31(1H，d)，7.66(1H，d)，7.81(1H，d)，8.45(1H，s)
HPLC：99.5％
MP：254℃
from the above data, it was found that the compound obtained above was 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine, and the total yield was 83.8%. The storage conditions are as follows: and (3) filling argon at a low temperature of 0-5 ℃.
Claims (1)
- The synthesis method of kinds of 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine is characterized by comprising the following steps:step 1): preparing a 10L glass reaction kettle, sequentially adding 3L ethanol and 93.6g of 2.34mol of sodium amide, cooling to 0-5 ℃ in an ice water bath, slowly adding 200g of 1.56mol of 2-amino-5-chloropyridine, and refluxing for 2 hours after the addition;step 2): dripping 275g of isoamyl nitrite, namely 2.34mol, at the temperature of 65-70 ℃, and refluxing for 2-3 hours after dripping;step 3): after the reaction is finished, cooling the reaction solution to 0-5 ℃, standing for 4 hours to generate a large amount of yellow solid, performing suction filtration to obtain 575g of intermediate diazonium salt with wet weight, pulping and washing with 5L of ethyl acetate, performing suction filtration, and drying to obtain 364g of diazonium salt as yellow crystals;step 4): preparing a 10L glass reaction kettle, sequentially adding 4.5L of ethanol and 364g of intermediate diazonium salt to be in a suspension state, cooling to 0-5 ℃ in an ice water bath, slowly dropwise adding a mixed solution, wherein the mixed solution is formed by mixing 280g of 1.56mol of m-phenylenediamine hydrochloride and 2L of water 192g of 2.34mol of sodium acetate, and after dropwise adding, continuously preserving the temperature at 0-5 ℃ for reaction for 3 hours, so that a large amount of red crystals appear;step 5): carrying out suction filtration on red crystals precipitated by the reaction, and then carrying out suspension washing on a filter cake by using 2L of water, and carrying out suction filtration to obtain 574g of wet heavy filter cake; and then adding the filter cake into 5L of ethanol, heating and refluxing for 1-2 hours, filtering, concentrating the filtrate to 1/2, adding 6L of 10% potassium hydroxide solution into the filtrate, refluxing for 2 hours, cooling to 0-5 ℃, keeping the temperature and standing for 3 hours, performing suction filtration, performing suspension washing on the filter cake with 2L of 80 ℃ water, performing suction filtration, and drying to obtain 322g of yellowish red crystal 4- (5-chloro-2-pyridylazo) -1, 3-phenylenediamine.
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| CN106220871A (en) * | 2016-07-29 | 2016-12-14 | 清华大学 | A kind of modification of chitosan gel micro-ball and preparation thereof and application |
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- 2018-03-20 CN CN201810229012.XA patent/CN108395730B/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105688829A (en) * | 2016-02-22 | 2016-06-22 | 清华大学 | Calcium alginate/5-Cl-PADAB microspheres and preparation method and application thereof |
| CN106220871A (en) * | 2016-07-29 | 2016-12-14 | 清华大学 | A kind of modification of chitosan gel micro-ball and preparation thereof and application |
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| 4-[(5-CHLORO-2-PYRIDYL)AZO]-1,3-DIAMINOBENZENE AS A NEW SENSITIVE AND SELECTIVE REAGENT FOR COBALT;SHOZO SHIBATA;《Anal. Chim. Acta》;19711231(第55期);231-237 * |
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| 吡啶偶氮试剂的进展;曲长菱;《化学试剂》;19861231;第8卷(第04期);211-221 * |
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