CN101025407A - Analytical method for determining micro moisture in cyclopropyl amine by gas phase chromatography - Google Patents
Analytical method for determining micro moisture in cyclopropyl amine by gas phase chromatography Download PDFInfo
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- CN101025407A CN101025407A CN 200610007918 CN200610007918A CN101025407A CN 101025407 A CN101025407 A CN 101025407A CN 200610007918 CN200610007918 CN 200610007918 CN 200610007918 A CN200610007918 A CN 200610007918A CN 101025407 A CN101025407 A CN 101025407A
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- Prior art keywords
- cyclopropylamine
- moisture
- internal standard
- molecular sieve
- sample
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- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 238000004458 analytical method Methods 0.000 title claims abstract description 19
- 238000004587 chromatography analysis Methods 0.000 title abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000002808 molecular sieve Substances 0.000 claims abstract description 12
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000012937 correction Methods 0.000 claims abstract description 10
- 239000012153 distilled water Substances 0.000 claims abstract description 7
- 239000012159 carrier gas Substances 0.000 claims abstract description 4
- 238000002309 gasification Methods 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 229910001220 stainless steel Inorganic materials 0.000 claims abstract description 4
- 239000010935 stainless steel Substances 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000007789 gas Substances 0.000 claims description 10
- 235000019441 ethanol Nutrition 0.000 claims description 6
- 238000013459 approach Methods 0.000 claims description 4
- 239000012925 reference material Substances 0.000 claims description 4
- 238000012545 processing Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 10
- 238000001514 detection method Methods 0.000 abstract description 3
- 238000004817 gas chromatography Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- 238000010521 absorption reaction Methods 0.000 abstract 2
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 238000003556 assay Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 238000010606 normalization Methods 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010813 internal standard method Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000003822 preparative gas chromatography Methods 0.000 description 3
- 238000012113 quantitative test Methods 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OOHIAOSLOGDBCE-UHFFFAOYSA-N 6-chloro-4-n-cyclopropyl-2-n-propan-2-yl-1,3,5-triazine-2,4-diamine Chemical compound CC(C)NC1=NC(Cl)=NC(NC2CC2)=N1 OOHIAOSLOGDBCE-UHFFFAOYSA-N 0.000 description 1
- SPFYMRJSYKOXGV-UHFFFAOYSA-N Baytril Chemical compound C1CN(CC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 SPFYMRJSYKOXGV-UHFFFAOYSA-N 0.000 description 1
- -1 Profloxacin Chemical compound 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229960003405 ciprofloxacin Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229960000740 enrofloxacin Drugs 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- VEBLEROFGPOMPB-UHFFFAOYSA-N n-methylcyclopropanamine Chemical compound CNC1CC1 VEBLEROFGPOMPB-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- DZZWHBIBMUVIIW-DTORHVGOSA-N sparfloxacin Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=C(F)C(N)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F DZZWHBIBMUVIIW-DTORHVGOSA-N 0.000 description 1
- 229960004954 sparfloxacin Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明公开了一种气相色谱测定环丙胺中微量水分的分析方法，其主要过程是以经5A分子筛吸水处理的环丙胺为溶剂，经5A分子筛吸水处理的无水乙醇为内标物，蒸馏水为标准物，制成水和乙醇比不同的环丙胺溶液，按照选定的色谱条件测定，计算出校正因子。测定样品时，在一定量的环丙胺中，准确加入一定量经脱水处理的无水乙醇内标物，按所选定色谱条件进行测定，经计算即可得出环丙胺中水分的分析结果。色谱分析条件为：Φ3×2000mm不锈钢填充柱，内填充GDX－201(80～100目)；柱温100～110℃；检测温度140～150℃；气化温度180～200℃；载气：高纯氢，流速25～30ml·min－1；柱前压0.02～0.03MPa；桥电流140～150mA；进样量1～3μl。本方法简便、适用、快速、准确，可用于环丙胺产品质量的检测。The invention discloses an analysis method for measuring trace moisture in cyclopropylamine by gas chromatography. The main process is to use cyclopropylamine treated with water absorption by 5A molecular sieve as solvent, absolute ethanol treated with water absorption by 5A molecular sieve as internal standard, and distilled water as The standard substance is made into cyclopropylamine solutions with different ratios of water and ethanol, measured according to the selected chromatographic conditions, and the correction factor is calculated. When measuring the sample, accurately add a certain amount of dehydrated anhydrous ethanol internal standard to a certain amount of cyclopropylamine, measure according to the selected chromatographic conditions, and calculate the analysis result of the moisture in the cyclopropylamine. The chromatographic analysis conditions are: Φ3×2000mm stainless steel packed column, filled with GDX-201 (80-100 mesh); column temperature 100-110°C; detection temperature 140-150°C; gasification temperature 180-200°C; carrier gas: high-purity hydrogen , flow rate 25~30ml·min -1 ; pre-column pressure 0.02~0.03MPa; bridge current 140~150mA; injection volume 1~3μl. The method is simple, applicable, fast and accurate, and can be used for the detection of the quality of cyclopropylamine products.
Description
Technical field
The invention belongs to a kind of chromatogram analysis method, is the analytical approach with micro-moisture in the gas Chromatographic Determination cyclopropylamine product concretely.
Background technology
Cyclopropylamine is the fatty amine that contains three-membered ring, is a kind of important fine-chemical intermediate.Be widely used in fields such as medicine, agricultural chemicals, organic synthesis.In medicine, be mainly used in synthesizing new antibiotic Ciprofloxacin, Profloxacin, sparfloxacin, Enrofloxacin etc.; In pesticide industry, be used for chemical herbicides such as the synthetic ring third careless amine, cyprazine, ring third cyanogen Tianjin, propyl group methyl cyclopropylamine.Application prospect in this external organic synthesis is also very wide.Cyclopropylamine product requirement cyclopropylamine content is more than 99.0%, and moisture is below 0.1%.The content of micro-moisture is the important means of control product quality in the assay determination cyclopropylamine.The assay method of moisture is a lot of in the organism, and gravimetric method, karl Fischer method, vapor-phase chromatography are arranged, and for the analysis of micro-moisture in the organism, generally adopts karl Fischer method and vapor-phase chromatography.The karl Fischer method is with the minor amount of water quantitative reaction in karl Fischer reagent (solution that iodine, sulphuric dioxide, pyridine and methyl alcohol are formed) and the sample, comes micro-moisture in the working sample with the karl Fischer reagent of known water content then.This method complex operation, fixed to the advanced rower of karl Fischer reagent important affair, just carry out titrimetry then, and the difficult keeping of Ka Er reagent and poisonous, the time of assay determination sample is longer, and analysis result data repeatability is also not so good.And vapor-phase chromatography is easy, quick, accurate because of it, has obtained general application in the assay determination of organism micro-moisture.Domestic production producer adopts karl Fischer method and gas chromatography normalization method substantially to the assay determination of micro-moisture in the cyclopropylamine at present.The gas chromatography normalization method just can draw measurement result after requiring all components all to go out the peak, and it is longer to expend time in, and is unfavorable for the quick monitoring of product quality.The condition of normalization method is that analysis result was more accurate when content differed not very big between component simultaneously.Because cyclopropylamine and moisture differ greatly in the cyclopropylamine product, are difficult to accurately measure the content of micro-moisture in the cyclopropylamine with normalization method.
Summary of the invention
The technical problem to be solved in the present invention provides a kind of chromatogram analysis method of measuring micro-moisture content in the cyclopropylamine.
Technical matters of the present invention is solved by following scheme: the analytical approach of micro-moisture in a kind of gas Chromatographic Determination cyclopropylamine, it is characterized in that: with the cyclopropylamine through 5A molecular sieve suction processing is solvent, the absolute ethyl alcohol of handling through the suction of 5A molecular sieve is an internal standard compound, distilled water is reference material, make water and ethanol than different cyclopropylamine solution, determine the result according to selected chromatographic condition, go out correction factor according to data computation then
During each mensuration, get in a certain amount of cyclopropylamine sample, accurately adding a certain amount of absolute ethyl alcohol of handling through the suction of 5A molecular sieve is internal standard compound, measure by selected chromatographic condition, the data that draw through gas Chromatographic Determination by the cyclopropylamine sample that adds internal standard compound, calculate the analysis result that can draw moisture in the cyclopropylamine through following formula, the analysis result of moisture in the cyclopropylamine:
In the formula: As is the peak area of internal standard compound; A
RPeak area for tester; Cs is the concentration of internal standard compound; C
RConcentration for tester; Ax is the peak area of specimen; Cx is the concentration of specimen; f
nBe the single calibration factor;
Be the average correction factor.The condition that stratographic analysis is used is: Ф 3 * 2000mm stainless steel packed column, interior filling GDX-201 (80～100 order); 100～110 ℃ of column temperatures; Thermal conductivity detector (TCD); 140～150 ℃ of detected temperatures; 180～200 ℃ of gasification temperatures; Carrier gas: High Purity Hydrogen, flow velocity 25～30mlmin
-1Press 0.02～0.03Mpa before the post; Bridge electric current 140～150mA; Sample size 1～3 μ l.
Advantage of the present invention is: the present invention has overcome normalization method needs all components such as long period all to go out the shortcoming that the peak just can draw measurement result, complete as long as water peak and ethanol peak go out the peak in the mensuration process, needn't wait main content cyclopropylamine to go out the peak, can adopt internal standard method to carry out quantitative test, realize measuring the purpose of micro-moisture in the cyclopropylamine.And internal standard method also can to offset stability of instrument poor, the quantitative test error that reason such as sample size is not accurate enough is brought.This method is easy, suitable, quick, accurate, can be used for the detection of product quality in the cyclopropylamine production.
Embodiment
1 instrument, reagent, sample
Gas chromatograph, thermal conductivity detector (TCD), data processing work station; GDX-201 (80～100 order); Distilled water is made reference material; Absolute ethyl alcohol (AR) is made internal standard compound; The 5A molecular sieve; The cyclopropylamine sample.
2 chromatographic run conditions
Chromatographic column: Ф 3 * 2000mm stainless steel packed column, interior filling GDX-201 (80～100 order); 100 ℃ of column temperatures; 150 ℃ of detected temperatures; 200 ℃ of gasification temperatures; Carrier gas: High Purity Hydrogen, flow velocity 25～30mlmin
-1Press 0.02Mpa before the post; Bridge electric current 150mA; Sample size 2 μ l.
3 experimental techniques
The absolute ethyl alcohol of handling through the suction of 5A molecular sieve is an internal standard compound, distilled water is reference material, and the cyclopropylamine of handling through 5A molecular sieve suction is a solvent, makes moisture and ethanol ratio and be 1: 4～4: 1 cyclopropylamine solution, measure liquid as measuring correction factor, measure by selected chromatographic condition.
Get in a certain amount of cyclopropylamine sample, accurately adding a certain amount of absolute ethyl alcohol of handling through 5A molecular sieve suction is internal standard compound, shakes up, and measures by selected chromatographic condition.
4 measurement results are calculated
Measure the data that liquid draws through gas Chromatographic Determination by correction factor, calculate the correction factor that each measures liquid, calculate the mean value of correction factor then according to following formula.
Correction factor calculates:
By the data that the cyclopropylamine sample that adds internal standard compound draws through gas Chromatographic Determination, calculate the analysis result that can draw moisture in the cyclopropylamine through following formula.The analysis result of moisture in the cyclopropylamine:
In following formula: As is the peak area of internal standard compound; A
RPeak area for tester; Cs is the concentration of internal standard compound; C
RConcentration for tester; Ax is the peak area of specimen; Cx is the concentration of specimen; f
nBe the single calibration factor;
Be the average correction factor.
5 chromatographic peak peak sequences
The cyclopropylamine sample under selected chromatographic condition, through gas Chromatographic Determination draw chromatogram result.Peak sequence is water (1.06min), ethanol (3.24min), cyclopropylamine (5.18min), and visible separating effect on the GDX-201 post is better.Do the requirement that internal standard compound can satisfy internal standard method with ethanol.And before not going out the peak, cyclopropylamine can carry out quantitative test.
6 sample analysis results
3 samples of cyclopropylamine have been carried out 5 times respectively measured, analysis result sees Table 1.Result's relative standard deviation is 2.94～4.01%.
Moisture analysis result (%) in the table 1. cyclopropylamine sample
| Sample number into spectrum | Analysis result | Mean value | Relative standard deviation | ||||
| 1 | 0.0912 | 0.0883 | 0.0856 | 0.0920 | 0.0878 | 0.0890 | 2.94 |
| 2 | 0.0984 | 0.0952 | 0.0976 | 0.0921 | 0.1026 | 0.0972 | 4.01 |
| 3 | 0.0998 | 0.1003 | 0.0966 | 0.1058 | 0.0965 | 0.0998 | 3.79 |
The experiment of 7 recovery
Accurately add the distilled water of different amounts respectively in the cyclopropylamine sample, carry out stratographic analysis then, calculate the recovery that adds distilled water by the gained measurement result, measurement result is as shown in table 2.The recovery is 97.60～103.3%.
Table 2. determination of recovery rates result (%)
| Sample number into spectrum | Moisture in the sample | Add the water yield in the sample | Record water inventory | The recovery |
| 1 | 0.089Q | 0.0500 | 0.1378 | 97.60 |
| 2 | 0.0972 | 0.1000 | 0.2005 | 103.3 |
| 3 | 0.0998 | 0.0500 | 0.1492 | 98.87 |
Claims (1)
1, the analytical approach of micro-moisture in a kind of gas Chromatographic Determination cyclopropylamine, it is characterized in that: with the cyclopropylamine through 5A molecular sieve suction processing is solvent, the absolute ethyl alcohol of handling through the suction of 5A molecular sieve is an internal standard compound, distilled water is reference material, make water and ethanol than different cyclopropylamine solution, determine the result according to selected chromatographic condition, calculate correction factor.During each mensuration, get in a certain amount of cyclopropylamine sample, accurately add a certain amount of absolute ethyl alcohol internal standard compound of handling through the suction of 5A molecular sieve, measure by selected chromatographic condition, the data that draw through gas Chromatographic Determination by the cyclopropylamine sample that adds internal standard compound, can draw the analysis result of moisture in the cyclopropylamine as calculated, the condition that stratographic analysis is used is: Φ 3 * 2000mm stainless steel packed column, interior filling GDX-201 (80～100 order); 100～110 ℃ of column temperatures; Thermal conductivity detector (TCD); 140～150 ℃ of detected temperatures; 180～200 ℃ of gasification temperatures; Carrier gas: High Purity Hydrogen, flow velocity 25～30mlmin
-1Press 0.02～0.03Mpa before the post; Bridge electric current 140～150mA; Sample size 1～3 μ l.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200610007918 CN101025407A (en) | 2006-02-23 | 2006-02-23 | Analytical method for determining micro moisture in cyclopropyl amine by gas phase chromatography |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200610007918 CN101025407A (en) | 2006-02-23 | 2006-02-23 | Analytical method for determining micro moisture in cyclopropyl amine by gas phase chromatography |
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| Publication Number | Publication Date |
|---|---|
| CN101025407A true CN101025407A (en) | 2007-08-29 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200610007918 Pending CN101025407A (en) | 2006-02-23 | 2006-02-23 | Analytical method for determining micro moisture in cyclopropyl amine by gas phase chromatography |
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| Country | Link |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102087253A (en) * | 2010-12-31 | 2011-06-08 | 广东中烟工业有限责任公司 | Method for determining content of free water in tobaccos |
| CN107179377A (en) * | 2017-05-23 | 2017-09-19 | 深圳职业技术学院 | The assay method of micro-moisture in organic solvent sample |
| CN108760905A (en) * | 2018-04-10 | 2018-11-06 | 广西壮族自治区柳州食品药品检验所 | A kind of method of moisture in measurement antibiotic |
| CN111921503A (en) * | 2020-07-16 | 2020-11-13 | 中国神华煤制油化工有限公司 | Application of divinylbenzene-trichloroethylene copolymer in determining water content of pentanal and method for determining water content of pentanal |
| CN116519833A (en) * | 2023-04-17 | 2023-08-01 | 金能科技股份有限公司 | Method for measuring trace moisture of p-methylphenol by gas chromatography |
-
2006
- 2006-02-23 CN CN 200610007918 patent/CN101025407A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102087253A (en) * | 2010-12-31 | 2011-06-08 | 广东中烟工业有限责任公司 | Method for determining content of free water in tobaccos |
| CN102087253B (en) * | 2010-12-31 | 2013-06-12 | 广东中烟工业有限责任公司 | Method for determining content of free water in tobaccos |
| CN107179377A (en) * | 2017-05-23 | 2017-09-19 | 深圳职业技术学院 | The assay method of micro-moisture in organic solvent sample |
| CN108760905A (en) * | 2018-04-10 | 2018-11-06 | 广西壮族自治区柳州食品药品检验所 | A kind of method of moisture in measurement antibiotic |
| CN111921503A (en) * | 2020-07-16 | 2020-11-13 | 中国神华煤制油化工有限公司 | Application of divinylbenzene-trichloroethylene copolymer in determining water content of pentanal and method for determining water content of pentanal |
| CN116519833A (en) * | 2023-04-17 | 2023-08-01 | 金能科技股份有限公司 | Method for measuring trace moisture of p-methylphenol by gas chromatography |
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Open date: 20070829 |