CN101629935B - Method of determining content of 2,6-dichloroquinoxaline - Google Patents
Method of determining content of 2,6-dichloroquinoxaline Download PDFInfo
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- CN101629935B CN101629935B CN200910016869A CN200910016869A CN101629935B CN 101629935 B CN101629935 B CN 101629935B CN 200910016869 A CN200910016869 A CN 200910016869A CN 200910016869 A CN200910016869 A CN 200910016869A CN 101629935 B CN101629935 B CN 101629935B
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- quinoxaline
- dichloro
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- WFOKVKYNVKVWFK-UHFFFAOYSA-N 2,6-dichloroquinoxaline Chemical compound N1=C(Cl)C=NC2=CC(Cl)=CC=C21 WFOKVKYNVKVWFK-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000004458 analytical method Methods 0.000 claims abstract description 16
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 7
- 238000012360 testing method Methods 0.000 claims description 11
- 239000012159 carrier gas Substances 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 230000005526 G1 to G0 transition Effects 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000005070 sampling Methods 0.000 claims description 6
- 238000004817 gas chromatography Methods 0.000 claims description 5
- 230000004907 flux Effects 0.000 claims description 4
- 239000001307 helium Substances 0.000 claims description 4
- 229910052734 helium Inorganic materials 0.000 claims description 4
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 3
- 238000003825 pressing Methods 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 abstract description 4
- 239000000047 product Substances 0.000 abstract description 3
- 238000004587 chromatography analysis Methods 0.000 abstract description 2
- 239000013067 intermediate product Substances 0.000 abstract description 2
- 238000003908 quality control method Methods 0.000 abstract description 2
- 238000011084 recovery Methods 0.000 abstract description 2
- 238000013375 chromatographic separation Methods 0.000 abstract 1
- 229910017053 inorganic salt Inorganic materials 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 8
- 238000005303 weighing Methods 0.000 description 7
- -1 2-(4-hydroxyphenoxy) ethyl Chemical group 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 230000033228 biological regulation Effects 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- OSUHJPCHFDQAIT-UHFFFAOYSA-N ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 238000001094 photothermal spectroscopy Methods 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
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- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Abstract
The invention relates to an analysis method of the content of 2,6-dichloroquinoxaline, which is a gas chromatographic analysis method. The method is characterized by adopting a gas chromatograph with a flame ionization detector (FID) and a capillary chromatographic column, using DMF to dissolve samples, taking diethyl phthalate as an internal standard substance to carry out gas chromatographic separation and determination of the 2,6-dichloroquinoxaline in the samples and computing the content of the 2,6-dichloroquinoxaline in the samples by comparison with the standard substances. The method can effectively avoid disturbance of inorganic salt and moisture and features good degree of precision, high recovery rate, correct results and good repeatability, which is especially suitable for the quality control of the 2,6-dichloroquinoxaline, an intermediate product of raw pesticides, and plays an important role in and has realistic significance in guaranteeing the quality of the final products.
Description
One, technical field
The invention belongs to the analysis and testing technology field, relate to chromatographic technique, particularly a kind of 2, the analysis on Content measuring technology of 6-dichloro-quinoxaline.
Two, background technology
2, the 6-dichloro-quinoxaline is the key intermediate of Quizalotop-ethyl, 2, and 6-dichloro-quinoxaline content is low excessively, directly affects quality, yield, the production cost of subsequent product.2,6-dichloro quinoxaline, molecular weight 199, industrial goods are faint yellow crystallization, 154 ℃-155 ℃ of fusing points are dissolved in organic solvents such as toluene, ethanol, and are water insoluble, mainly are used as the intermedium of pesticide herbicide and some PTSs.Pesticide herbicide is main with quizalofop-ethyl, 2, and 6-dichloro quinoxaline and 2-(4-hydroxyphenoxy) ethyl propionate reaction makes the herbicide quizalofop-ethyl, and it is a selectivity dry land herbicide behind the bud of Japanese Nissan chemical industrial company exploitation.Its activity of weeding is high, can prevent and kill off annual and perennial grassy weed, to broad leaf crop safety, can be widely used in cotton, rape, soybean, peanut and multiple broad-leaved vegetables field and prevent and kill off grassy weed.
2, in the production of 6-dichloro-quinoxaline, unavoidably bring inorganic salts and moisture content into; But in the gas-chromatography detection method of routine, fid detector does not have analog value to inorganic salts and moisture content; Therefore, the area percentage method in past can not reflect 2 truly, the content of 6-dichloro-quinoxaline (measured value is bigger than actual value); At present, also there is not method to measure this material fast and accurately both at home and abroad.
Three, summary of the invention
The object of the present invention is to provide a kind ofly 2, the Determination on content method of 6-dichloro-quinoxaline realizes to 2 the objective evaluation of 6-dichloro-quinoxaline content.
The objective of the invention is to realize like this, adopt gas chromatograph, capillary chromatographic column with flame ionization ditector; Use the DMF sample dissolution, do internal standard compound, to 2 in the sample with diethyl phthalate; The 6-dichloro-quinoxaline carries out the gas chromatography separation and measures; Through with the comparison of standard substance, calculate 2 in the sample, 6-dichloro-quinoxaline content.
The present invention relates to 2,6-dichloro-quinoxaline analysis on Content method is a gas chromatography analysis method, with 2; 6-dichloro-quinoxaline standard substance is done standard specimen, does interior mark with diethyl phthalate, the DMF sample dissolution; With capillary chromatographic column and flame ionization ditector test; The order of pressing standard specimen, sample, sample, standard specimen after the instrument baseline stability is sample introduction successively, and with in two pin samples that record and the two pin mark appearance 2, the 6-dichloro-quinoxaline averages respectively with the ratio of internal standard compound peak area; Calculate 2 by formula (1), 6-dichloro-quinoxaline massfraction X
1:
In the formula:
A
1---in the standard specimen, 2, the mean value of 6-dichloro-quinoxaline and interior mark peak area ratio;
A
2---in the sample, 2, the mean value of 6-dichloro-quinoxaline and interior mark peak area ratio;
m
1---2, the quality of 6-dichloro-quinoxaline standard specimen, g;
m
2---the quality of sample, g;
P---standard specimen 2, the massfraction of 6-dichloro-quinoxaline, %.
The present invention relates to 2,6-dichloro-quinoxaline analysis on Content method, said chromatographic column are 15 to 30 meters of column lengths; 0.53 millimeter of internal diameter is a stationary phase with SE-30, the capillary chromatographic column that thickness is 1 micron; Theoretical cam curve is by 2, and 6-dichloro-quinoxaline meter is not less than 2000.
The present invention relates to 2,6-dichloro-quinoxaline analysis on Content method, said chromatographic condition is 135 ℃ to 155 ℃ of column compartment temperature, 200 ℃ of vaporizers, 200 ℃ of detecting devices.Carrier gas flux 1.0～2.0mL/min, hydrogen flowing quantity 30mL/min, air mass flow 300mL/min, sampling volume are 1 microlitre.
The present invention relates to 2,6-dichloro-quinoxaline analysis on Content method, said carrier gas flux 1.5mL/min.
The present invention relates to 2,6-dichloro-quinoxaline analysis on Content method, 145 ℃ of said chromatographic column room temperatures.
The present invention relates to 2,6-dichloro-quinoxaline analysis on Content method, said carrier gas is a kind of in high pure nitrogen or the high-purity helium.
The present invention relates to 2,6-dichloro-quinoxaline analysis on Content method can effectively be avoided the interference of inorganic salts and moisture content, precision is good, the recovery is high, the result is accurate, good reproducibility.Be specially adapted to pesticide original medicine intermediate product 2, the quality control of 6-dichloro-quinoxaline has vital role and realistic meaning to the quality that guarantees final products.
Four, embodiment
Below in conjunction with specific embodiment invention is described further, but not as the restriction to summary of the invention.
Embodiment one
Employing has Tianjin, island GC-14C gas chromatograph of flame ionization ditector, uses capillary chromatographic column, 15 meters of column lengths, and 0.53 millimeter of internal diameter is a stationary phase with SE-30,1 micron of thickness, 135 ℃ of column compartment temperature, 200 ℃ of vaporizers, 200 ℃ of detecting devices.Do carrier gas with high-purity helium, flow 1.0mL/min, hydrogen flowing quantity 30mL/min, air mass flow 300mL/min, sampling volume are 1 microlitre, and theoretical cam curve is by 2, and the 6-dichloro-quinoxaline counts 2000.
Interior standard configuration system
Accurately take by weighing the 5.0028g diethyl phthalate in the brown volumetric flask of 500mL,, be cooled to room temperature, use the DMF constant volume, shake up with the DMF dissolving, subsequent use.
The standard specimen preparation
Accurately take by weighing 0.0504g 2,6-dichloro-quinoxaline standard substance places the 10mL volumetric flask, accurately moves into the 5mL inner mark solution, with the DMF dissolving, is cooled to room temperature, uses the DMF constant volume, shakes up, and is subsequent use.
The sample preparation
Accurately take by weighing and contain 2,5 on the sample of 6-dichloro-quinoxaline 0.05g (being accurate to 0.0002g) places 5 25mL volumetric flasks; Accurately move into the inner mark solution of 2.5mL, 5mL, 7.5mL, 10mL, 12.5mL respectively; Move into the DMF of 12.5mL, 10mL, 7.5mL, 5mL, 2.5mL more respectively, dissolving is cooled to room temperature; Shake up, subsequent use.
Test and data processing
Open the machine preheating, under the operating conditions of regulation, after the instrument baseline stability; Inject number pin mark appearance continuously; Calculate each pin relative response, the relative response of adjacent two pins changed less than 1.5% o'clock, measured by the order of standard specimen, sample, sample, standard specimen sample introduction successively; To sample quality ratio, get regression equation with peak area ratio as straight line
y＝0.9321x-0.00004 R
2＝1
It is thus clear that 2,6-dichloro-quinoxaline and interior mark mass ratio were good linear relationship between 1: 0.5 to 1: 2.5.
Embodiment two
Employing has Tianjin, island GC-14C gas chromatograph of flame ionization ditector, and interior mark and standard specimen preparation, test and computing method are used capillary chromatographic column with embodiment one; 30 meters of column lengths, 0.53 millimeter of internal diameter is a stationary phase with SE-30; 1 micron of thickness; 145 ℃ of column compartment temperature, 200 ℃ of vaporizers, 200 ℃ of detecting devices.Do carrier gas with high pure nitrogen, flow 2.0mL/min, hydrogen flowing quantity 30mL/min, air mass flow 300mL/min, sampling volume are 1 microlitre, and theoretical cam curve is by 2, and the 6-dichloro-quinoxaline counts 3000.
The sample preparation
Accurately take by weighing and contain 2,6 parts on the sample of 6-dichloro-quinoxaline 0.05g (being accurate to 0.0002g) places the 10mL volumetric flask respectively, accurately moves into the 5mL inner mark solution, with the DMF dissolving, is cooled to room temperature, uses the DMF constant volume, shakes up, and is subsequent use.
Test and data processing
Open the machine preheating, under the operating conditions of regulation, treat the instrument baseline stability after; Inject number pin mark appearance solution continuously; Calculate each pin relative response, the relative response of adjacent two pins changed less than 1.5% o'clock, measured by the order of standard specimen, sample, sample, standard specimen sample introduction successively; By the active constituent content of formula (1) calculating sample, Precision test result is listed in table 1.
Table 1
Embodiment three
Employing has Tianjin, island GC-14C gas chromatograph of flame ionization ditector, and interior mark and standard specimen preparation, test and computing method are used capillary chromatographic column with embodiment one; 20 meters of column lengths, 0.53 millimeter of internal diameter is a stationary phase with SE-30; 1 micron of thickness; 155 ℃ of column compartment temperature, 200 ℃ of vaporizers, 200 ℃ of detecting devices.Do carrier gas with high pure nitrogen, flow 1.5mL/min, hydrogen flowing quantity 30mL/min, air mass flow 300mL/min, sampling volume are 1 microlitre, and theoretical cam curve is by 2, and the 6-dichloro-quinoxaline counts 2500.
The sample preparation
Accurately take by weighing and contain 2, the sample of 6-dichloro-quinoxaline 0.0506g places the 10mL volumetric flask, accurately moves into the 5mL inner mark solution, with the DMF dissolving, is cooled to room temperature, uses the DMF constant volume, shakes up, and is subsequent use.
Test and data processing
Open the machine preheating, under the operating conditions of regulation, treat the instrument baseline stability after; Inject number pin mark appearance solution continuously; Calculate each pin relative response, the relative response of adjacent two pins changed less than 1.5% o'clock, measured by the order of standard specimen, sample, sample, standard specimen sample introduction successively.Different time sequential determination 6 times, calculate the active constituent content of sample by formula (1), the result lists in table 2, and the result shows and has good stability.
Table 2
| Time (h) | 0 | 1 | 2 | 4 | 8 | 24 | RSD％ |
| Peak area ratio | 0.87923 | 0.88156 | 0.88036 | 0.88258 | 0.88160 | 0.88120 | 0.13 |
Embodiment four
Employing has Tianjin, island GC-14C gas chromatograph of flame ionization ditector, and interior mark and standard specimen preparation, test and computing method are used capillary chromatographic column with embodiment one; 25 meters of column lengths, 0.53 millimeter of internal diameter is a stationary phase with SE-30; 1 micron of thickness; 145 ℃ of column compartment temperature, 200 ℃ of vaporizers, 200 ℃ of detecting devices.Do carrier gas with high-purity helium, flow 1.5mL/min, hydrogen flowing quantity 30mL/min, air mass flow 300mL/min, sampling volume are 1 microlitre, and theoretical cam curve is by 2, and the 6-dichloro-quinoxaline counts 2800.
The sample preparation
Accurately take by weighing precision and take by weighing about 0.02 gram of sample, 0.03 gram, 0.04 gram, each three parts, put in the 10ml volumetric flask; Accurately add standard specimen (10.002mg/ml) 3.0ml, 2.5ml, 2.0ml respectively, accurately move into mark in the 5mL more respectively, dissolve with DMF; Constant volume shakes up, and is subsequent use.
Test and data processing
Open the machine preheating, under the operating conditions of regulation, treat the instrument baseline stability after; Inject number pin mark appearance solution continuously; Calculate each pin relative response, the relative response of adjacent two pins changed less than 1.5% o'clock, measured by the order of standard specimen, sample, sample, standard specimen sample introduction successively.The result lists in table 3.
Table 3
Claims (4)
1. one kind 2,6-dichloro-quinoxaline analysis on Content method, said analytical approach is a gas chromatography analysis method; With 2,6-dichloro-quinoxaline standard substance is done standard specimen, does interior mark with diethyl phthalate; The DMF sample dissolution, with the test of capillary chromatographic column and flame ionization ditector, the order of pressing standard specimen, sample, sample, standard specimen after the instrument baseline stability is sample introduction successively; With in two pin samples that record and the two pin mark appearance 2; The 6-dichloro-quinoxaline averages respectively with the ratio of internal standard compound peak area, calculates 2 by formula (1), 6-dichloro-quinoxaline massfraction X
1:
In the formula:
A
1---in the standard specimen, 2, the mean value of 6-dichloro-quinoxaline and interior mark peak area ratio;
A
2---in the sample, 2, the mean value of 6-dichloro-quinoxaline and interior mark peak area ratio;
m
1---2, the quality of 6-dichloro-quinoxaline standard specimen, g;
m
2---the quality of sample, g;
P---standard specimen 2, the massfraction of 6-dichloro-quinoxaline, %;
Wherein: 15 to 30 meters of capillary chromatographic column column lengths, 0.53 millimeter of internal diameter is a stationary phase with SE-30,1 micron of thickness, theoretical cam curve is by 2, and 6-dichloro-quinoxaline meter is not less than 2000;
Analytical conditions for gas chromatography is 135 ℃ to 155 ℃ of column compartment temperature, 200 ℃ of vaporizers, 200 ℃ of detecting devices; Carrier gas flux 1.0～2.0mL/min, hydrogen flowing quantity 30mL/min, air mass flow 300mL/min, sampling volume are 1 microlitre.
Claim 1 relate to 2,6-dichloro-quinoxaline analysis on Content method, said carrier gas flux 1.5mL/min.
Claim 1 relate to 2,6-dichloro-quinoxaline analysis on Content method, 145 ℃ of said column compartment temperature.
Claim 1 relate to 2,6-dichloro-quinoxaline analysis on Content method, said carrier gas is high pure nitrogen or high-purity helium.
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| Application Number | Priority Date | Filing Date | Title |
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| CN200910016869A CN101629935B (en) | 2009-07-22 | 2009-07-22 | Method of determining content of 2,6-dichloroquinoxaline |
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| CN200910016869A CN101629935B (en) | 2009-07-22 | 2009-07-22 | Method of determining content of 2,6-dichloroquinoxaline |
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| CN101629935B true CN101629935B (en) | 2012-10-10 |
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| CN111141736B (en) * | 2019-12-31 | 2022-07-29 | 佛山市南海北沙制药有限公司 | Detection method for identifying 2-chloroquinoxaline |
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Non-Patent Citations (2)
| Title |
|---|
| 李建生等.2，6－二氯喹恶啉.《精细与专用化学品》.2000,(第15期),第11－12页. * |
| 黄惠玲等.毛细管气相色谱法测定12种农药的有效成分.《色谱》.2001,第19卷(第4期),第347-349页. * |
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Address after: 256500 Boxing Economic Development Zone, Shandong, Binzhou Patentee after: Shandong Jingbo Agrochemical Technology Co.,Ltd. Patentee after: Shandong Jingbo Biotechnology Co.,Ltd. Address before: 256500 Boxing Economic Development Zone, Shandong, Binzhou Patentee before: JINGBO AGROCHEMICALS TECHNOLOGY Co.,Ltd. Patentee before: Shandong Jingbo Biotechnology Co.,Ltd. |