CN101303311A - Method for testing nitroaniline content - Google Patents
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- CN101303311A CN101303311A CNA2008100626113A CN200810062611A CN101303311A CN 101303311 A CN101303311 A CN 101303311A CN A2008100626113 A CNA2008100626113 A CN A2008100626113A CN 200810062611 A CN200810062611 A CN 200810062611A CN 101303311 A CN101303311 A CN 101303311A
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- 238000000034 method Methods 0.000 title claims abstract description 37
- 238000012360 testing method Methods 0.000 title description 24
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 39
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000001514 detection method Methods 0.000 claims abstract description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 11
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 6
- 239000013558 reference substance Substances 0.000 claims description 25
- 239000000243 solution Substances 0.000 claims description 25
- 239000012530 fluid Substances 0.000 claims description 12
- 238000002835 absorbance Methods 0.000 claims description 11
- 239000011550 stock solution Substances 0.000 claims description 7
- 238000004458 analytical method Methods 0.000 claims description 6
- 238000004364 calculation method Methods 0.000 claims description 6
- 238000002798 spectrophotometry method Methods 0.000 claims description 6
- WZRRZVUZWWMSKH-UHFFFAOYSA-N n'-naphthalen-1-ylethane-1,2-diamine;hydrochloride Chemical compound Cl.C1=CC=C2C(NCCN)=CC=CC2=C1 WZRRZVUZWWMSKH-UHFFFAOYSA-N 0.000 claims description 5
- 239000012266 salt solution Substances 0.000 claims description 5
- 238000011161 development Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 238000010790 dilution Methods 0.000 claims description 3
- 239000012895 dilution Substances 0.000 claims description 3
- -1 sulfaminic acid ammonium salt Chemical class 0.000 claims description 2
- 238000002604 ultrasonography Methods 0.000 claims description 2
- 238000005259 measurement Methods 0.000 abstract description 7
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 abstract description 6
- 238000007865 diluting Methods 0.000 abstract description 3
- 230000003287 optical effect Effects 0.000 abstract 3
- ZCUQOPGIJRGJDA-UHFFFAOYSA-N 1-naphthalen-1-ylethane-1,2-diamine Chemical compound C1=CC=C2C(C(N)CN)=CC=CC2=C1 ZCUQOPGIJRGJDA-UHFFFAOYSA-N 0.000 abstract 1
- GEHMBYLTCISYNY-UHFFFAOYSA-N Ammonium sulfamate Chemical compound [NH4+].NS([O-])(=O)=O GEHMBYLTCISYNY-UHFFFAOYSA-N 0.000 abstract 1
- 238000004040 coloring Methods 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 230000009514 concussion Effects 0.000 description 5
- 238000007689 inspection Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- MZNYWPRCVDMOJG-UHFFFAOYSA-N N-(1-naphthyl)ethylenediamine dihydrochloride Chemical compound [Cl-].[Cl-].C1=CC=C2C([NH2+]CC[NH3+])=CC=CC2=C1 MZNYWPRCVDMOJG-UHFFFAOYSA-N 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000003317 industrial substance Substances 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 238000003822 preparative gas chromatography Methods 0.000 description 2
- 238000003908 quality control method Methods 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006149 azo coupling reaction Methods 0.000 description 1
- 239000012490 blank solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010205 computational analysis Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
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Abstract
The invention discloses a paranitroaniline content detection method, having technique content of 1) dissolving an analytically pure contrast of the paranitroaniline detection by methanol under an ultrasonic condition, diluting by a dilute sulfuric acid solution to obtain a concentrated liquid, 2) diluting the concentrated liquid of the contrast as required to prepare a series solution with a determined concentration, charging a sodium nitrite solution, an ammonium sulfamate solution and a 2-hydrochloric acid naphthyl ethylenediamine solution sequentially for a coloring process so as to obtain a work liquid series capable of optical density (OD) measurement, measuring the optical density (OD), 3) processing the concentration and the optical density (OD) of the work liquid series of the contrast to obtain a standard curve and a corresponding regression equation, 4) processing and measuring the sample to be measured by the same method, and calculating the paranitroaniline concentration of weight percentage in the sample by the regression equation.
Description
Technical field
The invention belongs to chemical technology field, relate to the method for quick of the p-nitrophenyl amine content of industrial chemicals product.
Background technology
Paranitroanilinum is a kind of important organic synthesis intermediate, is widely used in dyestuff, agricultural chemicals, medicine, veterinary drug and the rubber industry.Because China's chemical industry development in recent years is rapider; the intermediate or the end product quality of gained comply with the national standard requirements aborning in order to ensure chemical products; just must hold gate of the quality monitoring, inspection technology difficulty or ease and inspection cost size also are that enterprise must consider comprehensive factor in normal operation simultaneously.Generally speaking, the content of chemical products is high more the production economic worth more, therefore, search out a kind of accurate, quick, easy content assaying method, its intermediate control or end product quality check there is very big practicality, also can bring economic benefit to enterprise, especially to technical force and economic strength comparatively weak but relate to the medium-sized and small enterprises of producing or using the p-nitrophenyl amine product, the quality control inspection of this product is necessary.
In existing suitability for industrialized production, paranitroanilinum industrial products content reached 98% mass percent concentration or more than.In existing suitability for industrialized production, the check of paranitroanilinum is to dilute by the high-purity sample being carried out several, utilizes gas chromatography to carry out quantitative measurement then, and the gas chromatography analysis method complicated operating process, the reviewer demands strict technology, and it is also higher to detect cost.The paranitroanilinum Determination on content except that the gas phase chromatographic detection, is not seen fast and convenient assay method open source literature of its content and method report at present as yet.
Disclosed national standard method GB/T17072-1997 " the solvent desorption gas Chromatographic Determination method of paranitroanilinum in the workshop air " is used in environment measuring, and this method is suitable for the detection of low concentration environmental samples in the air.
Disclosed national standard method GB 11889-89 " N-(1-naphthyl) ethylenediamine azo spectrophotometric method " is used in the monitoring of environmental wastewater, and this method is suitable for the detection of the low concentration environmental samples of aniline family series.
If the assay that utilizes the method for environment measuring directly to carry out paranitroanilinum will run into following problem:
The first, be the integrated concentration that reference substance is investigated such Product Family with aniline, specific aim is poor, has the possibility of error;
The second, the accuracy of this method measurement result, precision are applicable to that less demanding environmental samples measures, and to the assay of accuracy, suitability for industrialized production finished product that precision requirement is higher, method must be improved;
Three, learn by the solubleness in the water liquid of investigating paranitroanilinum, the solubleness of paranitroanilinum in the 100g pure water is: 0.08g/18.5 ℃, or 2.2g/100 ℃, it has certain dissolubility in hydrothermal solution, but solution solubleness in returning to the process of room temperature obviously reduces; Its dissolubility in acidic aqueous solution has same performance, and in the time of 25 ℃, solubleness is less than 0.2g/100ml in the sulphur acid liquid of 0.025mol/L.
Therefore, narrow solubility range has influenced the course of dissolution of commercial production sample, has certain control difficulty and uncertain factor during dissolution process, does not thoroughly separate out the accuracy that influences measurement result after dissolving or the dissolving thereby cause easily.
Summary of the invention
The method for quick that the purpose of this invention is to provide industrial chemicals p-nitrophenyl amine content.This method adopts conventional spectrophotometric determination method and analytical reagent to carry out assay, its analysis operation process is simple, its good reproducibility, SOLUTION PROPERTIES is stable, measurement result is accurate, and is easy to detect, and cost is low, practical, be a kind of easy, the economical and practical method of the finished product quality inspection of paranitroanilinum suitability for industrialized production or its intermediate control.
Paranitroanilinum content detecting method of the present invention is: utilize the paranitroanilinum in the dissolve with methanol testing sample, dilute by dilution heat of sulfuric acid, with the diazo coupling agent its solution being carried out color development again handles, directly obtain to contain in the sample concentration of pure paranitroanilinum then, obtain its quality percentage composition by calculating then with the spectrophotometer detection computations.
Concrete steps are as follows:
(1) dissolve the pure paranitroanilinum of analysis with methyl alcohol under ultrasound condition and detect reference substance, the sulfuric acid solution dilution with 0.025 mol (mol/L) obtains paranitroanilinum and detects the reference substance stock solution;
(2) the detection reference substance stock solution of paranitroanilinum is diluted to concentration series solution by the requirement of drawing standard curve map after, add sodium nitrite solution successively, the sulfaminic acid ammonium salt solution, two hydrochloric acid naphthyl ethylenediamine solution carry out color development to be handled, can be used for the working fluid series of spectrophotometry with acquisition, and measure its absorbance (OD) value;
(3) absorbance (OD) value and the corresponding detection reference substance concentration with working fluid series is coordinate, with Excel software processes drawing standard curve map, and obtains its corresponding regression equation;
(4) prepare detected sample and absorbance (OD) value of measuring it by above-mentioned (1)～(2) step, obtain to contain in this detected sample the quality percentage composition of pure paranitroanilinum by the regression equation calculation that detects reference substance.
Description of drawings
Fig. 1 detects the reference substance working curve diagram for paranitroanilinum.
Embodiment
Specimen preparation that the present invention relates to and detecting operation concrete steps are as follows:
1), detect the preparation of reference substance stock solution:
Accurately take by weighing and analyze about 0.05 gram (g) of pure paranitroanilinum, place 100 milliliters of (ml) volumetric flasks, add the methyl alcohol of 50 milliliters (ml), ultrasonic dissolution, after leaving standstill and being cooled to room temperature, the sulfuric acid solution that adds 0.025 mol (mol/L) is settled to 100 milliliters (ml).
Get this solution 1ml and place the 50ml volumetric flask, the sulfuric acid solution that adds 0.025 mol (mol/L) is settled to 50 milliliters (ml) and promptly gets and detect the reference substance stock solution, and wherein per 1 milliliter (ml) contains about 10 micrograms of paranitroanilinum (μ g).
2) making of reference substance working fluid:
Get the tool plug scale test tube of 15 25 milliliters (ml), add respectively 1,2,3,4 with the detection reference substance stock solution (each concentration is established 3 parallel repetition test tubes) of 5 milliliters (ml), in each test tube all with distilled water diluting to 10 milliliter (ml).
Add 1 milliliter of the sodium nitrite solution (ml) of 2 grams per liters (g/L) in above-mentioned each test tube, left standstill after shaking up 3 minutes.
Add 25 grams per liters (g/L), 0.2 milliliter of ammonium salt solution of sulfaminic acid (ml) in above-mentioned each test tube, fully left standstill 3 minutes after the concussion.
Add 10 grams per liters (g/L), two hydrochloric acid naphthyl ethylenediamines [N-(1-naphthyl) ethylenediamine dihydrochloride], 1 milliliter of solution (ml) in above-mentioned each test tube again, fully left standstill 3 minutes after the concussion.
The last methyl alcohol that adds is diluted to 25 milliliters (ml) in above-mentioned each test tube, shakes up promptly to get concentration and be about 0.4 * 10
-3, 0.8 * 10
-3, 1.2 * 10
-3, 1.6 * 10
-3With 2.0 * 10
-3Three groups of reference substance working fluid series that repeat of grams per liter (g/L).
Normal temperature is placed after 30 minutes down, and last machine carries out data test.
3) preparation of blank reference liquid:
Get the tool plug scale test tube of 1 25 milliliters (ml), add 0.1 milliliter of (ml) methyl alcohol, add 0.025 mol (mol/L) sulfuric acid solution of 3 milliliters (ml) then, again with distilled water to 10 milliliter (ml).
Add 1 milliliter of the sodium nitrite solution (ml) of 2 grams per liters (g/L) in the test tube, left standstill after shaking up 3 minutes.
Add 25g/L 0.2 milliliter of ammonium salt solution of sulfaminic acid (ml) in the test tube, fully left standstill 3 minutes after the concussion.
Add 10g/L two hydrochloric acid naphthyl ethylenediamines [N-(1-naphthyl) ethylenediamine dihydrochloride] 1 milliliter of solution (ml) in the test tube again, fully left standstill 3 minutes after the concussion.
The last methyl alcohol that adds is diluted to 25 milliliters (ml) in the test tube, shakes up and promptly gets blank working fluid.
Normal temperature was placed down after 30 minutes, as the blank reference of last machine test.
4) acquisition of reference substance working curve:
With blank working fluid is the reference liquid deduction blank of spectrophotometry, measure absorbance (OD) value of reference substance working fluid at spectrophotometer 545nm wavelength place with the 1.0mm cuvette, represent absorbance (OD) value of the reference substance of this concentration with the mean value of 3 replication values of same concentration.
Mean light absorbency (OD) value with reference substance is horizontal ordinate (X), and corresponding concentration value is ordinate (Y), with Excel software processes and drawing standard curve, promptly obtains the reference substance working curve diagram equation of linear regression relevant with it of paranitroanilinum.
5), the preparation of detected sample working fluid and mensuration:
Precision takes by weighing the detected sample that is equivalent to contain pure paranitroanilinum 0.05 gram (g), place 100 milliliters of (ml) volumetric flasks, add 50 milliliters of (ml) methyl alcohol, ultrasonic dissolution, after leaving standstill and being cooled to room temperature, the sulfuric acid solution that adds 0.025 mol (mol/L) is settled to 100 milliliters (ml).
Get this solution 1 milliliter (ml) and place 50 milliliters of (ml) volumetric flasks (test sample to be checked is established 3 parallel repetition test tubes), the sulfuric acid solution that adds 0.025 mol (mol/L) is settled to 50 milliliters (ml).
Precision is measured 3 milliliters (ml) and is put in 25 milliliters of (ml) tool plug scale test tubes, and adding distil water is diluted to 10 milliliters (ml).
Add 1 milliliter of the sodium nitrite solution (ml) of 2 grams per liters (g/L), left standstill after shaking up 3 minutes.
Add 25 grams per liters (g/L), 0.2 milliliter of ammonium salt solution of sulfaminic acid (ml), fully left standstill 3 minutes after the concussion.
Add 10 grams per liters (g/L), two hydrochloric acid naphthyl ethylenediamines [N-(1-naphthyl) ethylenediamine dihydrochloride], 1 milliliter of solution (ml) again.
Be diluted to 25 milliliters (ml) with methyl alcohol at last, shake up.Normal temperature is placed after 30 minutes down, and last machine carries out data test.
The equal instrument condition of measuring with the reference substance working fluid and identical blank solution are measured absorbance (OD) value of test sample to be checked as reference.
The mean value of getting 3 sub-values is represented the absorbance of test sample to be checked (OD) value, contains the concentration of pure product paranitroanilinum in the substitution regression equation in the calculation sample.
But this concentration data conversion calculations draws the quality numerical value of paranitroanilinum in the sample, maybe can calculate the percentage composition of paranitroanilinum in the detected sample.
Method reliability demonstration of the present invention:
1), linear dependence Journal of Sex Research:
Accurately take by weighing paranitroanilinum reference substance 0.0504 gram (g), by above step, after handling again set by step, the production standard curve, (X is an absorbance to get regression equation Y=2.7177X+0.1905, Y is a paranitroanilinum concentration), calculate and know its linearly dependent coefficient r=0.9996, satisfy the requirement of method fully to precision.Concrete typical curve as shown in Figure 1.
Through research, the paranitroanilinum sample is 0.1 * 10
-3Keep higher dependent linearity in the concentration range of grams per liter (g/L)～0.2 grams per liter (g/L).
2), recovery research: take by weighing 5 parts of standard items, press its content of above step measurements, measurement result such as following table:
Its average recovery rate is 99.11%, and the standard deviation (RSD) of the corresponding recovery is 0.23%, and it meets the precision requirement of quantitative analysis method fully.
3), the method significant difference is analyzed (adopting F value determining method):
Take by weighing same batch of 4 parallel sample, measure by above step with the inventive method, adopt vapor-phase chromatography that same batch of sample measured simultaneously, comparing result also adopts the F method of inspection that two kinds of method gained results are carried out computational analysis, to judge whether there is significant difference between two methods.
The F value calculate to be judged (F calculations=S2 greatly/S2 is little):
F calculates=2.16, look into the F table and obtain F table=9.28 (degree of confidence 95%), as seen F calculation＜F table shows between these two kinds of detection methods of vapor-phase chromatography and UV-VIS spectrophotometry not have significant difference, can replace mutually between two kinds of methods and can not produce significant difference.
4), select with reference to product: the present invention adopts and analyzes pure paranitroanilinum reagent as with reference to product, has had specific aim.
5), solubility study: paranitroanilinum is easily molten in methyl alcohol.The present invention adopts dissolve with methanol with reference to product and testing sample, overcome the narrow disadvantage of water liquid solubleness, has got rid of the dissolving of water liquid not thoroughly or separate out after the heating for dissolving and the analysis result accuracy that causes is low, the disadvantage of precision difference.
The concrete research conclusion of implementing:
Visible spectrophotometric method of the present invention can be measured at visible region; Detect reference substance targetedly by using, improved the confidence level that detects data; By using dissolve with methanol, enlarged solubility range, and improved the stability property of solution; Method accuracy and precision have finally been improved thus.Operating process of the present invention is simple and convenient, testing result is accurate, good reproducibility, economical and practical, method can directly be applied to the content analysis and the quality control of chemical industry finished product accurately and rapidly, also can be applicable to the fast measuring of intermediate in its production run, so the present invention there is actual popularization economic worth.
Claims (1)
1, paranitroanilinum content detecting method, its feature comprises the steps:
(1) dissolve the pure paranitroanilinum of analysis with methyl alcohol under ultrasound condition and detect reference substance, the sulfuric acid solution dilution with 0.025 mol (mol/L) obtains paranitroanilinum and detects the reference substance stock solution;
(2) the detection reference substance stock solution of paranitroanilinum is diluted to concentration series liquid by the requirement of drawing standard curve map after, add sodium nitrite solution successively, the sulfaminic acid ammonium salt solution, two hydrochloric acid naphthyl ethylenediamine solution carry out color development to be handled, can be used for the working fluid series of spectrophotometry with acquisition, and measure its absorbance (OD) value;
(3) absorbance (OD) value and the corresponding detection reference substance working fluid concentration with working fluid series is coordinate, with Excel software processes drawing standard curve map, and obtains its corresponding regression equation;
(4) prepare detected sample and absorbance (OD) value of measuring it by above-mentioned (1)～(2) step, obtain to contain in this detected sample the quality percentage composition of pure paranitroanilinum by the regression equation calculation that detects reference substance.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008100626113A CN101303311B (en) | 2008-06-24 | 2008-06-24 | Method for testing nitroaniline content |
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|---|---|---|---|
| CN2008100626113A CN101303311B (en) | 2008-06-24 | 2008-06-24 | Method for testing nitroaniline content |
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| CN101303311B CN101303311B (en) | 2010-07-21 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102507549A (en) * | 2011-10-14 | 2012-06-20 | 沈阳建筑大学 | Method for measuring concentration of aniline in aqueous solution |
| CN101776653B (en) * | 2010-01-20 | 2012-11-21 | 谱尼测试科技股份有限公司 | Method for measuring o-fluoronitrobenzene in water by gas chromatography (GC) |
| CN107064025A (en) * | 2017-01-07 | 2017-08-18 | 台州市绿安检测技术有限公司 | A kind of assay method of Nitrobenzene in Wastewater class compound |
-
2008
- 2008-06-24 CN CN2008100626113A patent/CN101303311B/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101776653B (en) * | 2010-01-20 | 2012-11-21 | 谱尼测试科技股份有限公司 | Method for measuring o-fluoronitrobenzene in water by gas chromatography (GC) |
| CN102507549A (en) * | 2011-10-14 | 2012-06-20 | 沈阳建筑大学 | Method for measuring concentration of aniline in aqueous solution |
| CN107064025A (en) * | 2017-01-07 | 2017-08-18 | 台州市绿安检测技术有限公司 | A kind of assay method of Nitrobenzene in Wastewater class compound |
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| Publication number | Publication date |
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| CN101303311B (en) | 2010-07-21 |
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Denomination of invention: Method for testing nitroaniline content Effective date of registration: 20150417 Granted publication date: 20100721 Pledgee: The Bank of Nanjing Limited by Share Ltd of Hangzhou city Small and micro businesses franchise branch Pledgor: Zhejiang Huineng Animal Pharmaceutical Co. Ltd.|Gansu Department of Biological Engineering Co. Ltd.|Hangzhou Department of Biological Technology Co. Ltd. Registration number: 2015330000019 |
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Address after: 314422 Zhejiang Province, Haining city Changan Town Road No. 3 spring Patentee after: ZHEJIANG ESIGMA BIOTECHNOLOGY CO., LTD. Address before: 314422 No. 3, Lan Xi Road, Changan Town, Haining, Zhejiang Patentee before: Zhejiang Huineng Animal Medicine Co., Ltd. |
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Date of cancellation: 20170228 Granted publication date: 20100721 Pledgee: The Bank of Nanjing Limited by Share Ltd of Hangzhou city Small and micro businesses franchise branch Pledgor: Zhejiang Huineng Animal Pharmaceutical Co. Ltd.|Gansu Huineng Biological Engineering Co. Ltd. Registration number: 2015330000019 |
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| PM01 | Change of the registration of the contract for pledge of patent right |
Change date: 20170222 Registration number: 2015330000019 Pledgor after: Zhejiang Huineng Animal Pharmaceutical Co. Ltd. Pledgor after: Gansu Huineng Biological Engineering Co. Ltd. Pledgor before: Zhejiang Huineng Animal Pharmaceutical Co. Ltd. Pledgor before: Gansu Huineng Biological Engineering Co. Ltd. Pledgor before: Hangzhou Huineng Biological Technology Co. Ltd. |
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| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
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Denomination of invention: Method for testing nitroaniline content Effective date of registration: 20170303 Granted publication date: 20100721 Pledgee: The Bank of Nanjing Limited by Share Ltd of Hangzhou city Small and micro businesses franchise branch Pledgor: Gansu Huineng Biological Engineering Co. Ltd.|Zhejiang Huineng biological Limited by Share Ltd Registration number: 2017330000019 |
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| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20100721 Termination date: 20200624 |