CN101769906B - Derivatization method for detecting content of lactamyl magnesium salt - Google Patents
Derivatization method for detecting content of lactamyl magnesium salt Download PDFInfo
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- CN101769906B CN101769906B CN2009100764160A CN200910076416A CN101769906B CN 101769906 B CN101769906 B CN 101769906B CN 2009100764160 A CN2009100764160 A CN 2009100764160A CN 200910076416 A CN200910076416 A CN 200910076416A CN 101769906 B CN101769906 B CN 101769906B
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- China
- Prior art keywords
- lactamyl
- magnesium
- magnesium salt
- content
- derivatization
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- 238000000034 method Methods 0.000 title claims abstract description 17
- 159000000003 magnesium salts Chemical class 0.000 title claims abstract description 16
- 238000001212 derivatisation Methods 0.000 title claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims abstract description 14
- 229910001623 magnesium bromide Inorganic materials 0.000 claims abstract description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 239000012483 derivatization solution Substances 0.000 claims abstract description 3
- -1 lactams magnesium salts Chemical class 0.000 claims description 13
- BVJSGOYEEDZAGW-UHFFFAOYSA-N [chloro(nitro)methyl]benzene Chemical compound [O-][N+](=O)C(Cl)C1=CC=CC=C1 BVJSGOYEEDZAGW-UHFFFAOYSA-N 0.000 claims description 7
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 6
- 238000009413 insulation Methods 0.000 claims description 5
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- YIFCDKDXYUCWAZ-UHFFFAOYSA-L magnesium;azepan-2-one;dibromide Chemical compound [Mg+2].[Br-].[Br-].O=C1CCCCCN1 YIFCDKDXYUCWAZ-UHFFFAOYSA-L 0.000 claims description 2
- VOLRSQPSJGXRNJ-UHFFFAOYSA-N 4-nitrobenzyl bromide Chemical compound [O-][N+](=O)C1=CC=C(CBr)C=C1 VOLRSQPSJGXRNJ-UHFFFAOYSA-N 0.000 abstract 1
- KGCNHWXDPDPSBV-UHFFFAOYSA-N p-nitrobenzyl chloride Chemical compound [O-][N+](=O)C1=CC=C(CCl)C=C1 KGCNHWXDPDPSBV-UHFFFAOYSA-N 0.000 abstract 1
- 238000004321 preservation Methods 0.000 abstract 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 150000003951 lactams Chemical group 0.000 description 7
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241001597008 Nomeidae Species 0.000 description 3
- FUMLKAFCVQJVEZ-UHFFFAOYSA-N [bromo(nitro)methyl]benzene Chemical compound [O-][N+](=O)C(Br)C1=CC=CC=C1 FUMLKAFCVQJVEZ-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000012086 standard solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 2
- 229910001641 magnesium iodide Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 238000012113 quantitative test Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000005477 standard model Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
The invention provides a derivatization method for detecting the content of lactamyl magnesium salt. The method includes the following steps: the lactamyl magnesium salt is dissolved in an ether solvent, excess p-nitrobenzyl chloride or p-nitrobenzyl bromide is added, and then the heat-preservation reaction is carried out under the temperature of 30 to 60 DEG C so as to obtain derivatization solution to be detected. The derivatization reaction can be used for accurately detecting the content of lactamyl magnesium bromide and the lactamyl magnesium salt with the similar structure.
Description
Technical field
The present invention relates to a kind of derivatization method that is used to detect content of lactamyl magnesium salt.This derivative reaction can be used to accurately detect lactamyl magnesium salt (formula 1) content of lactam group magnesium bromide and similar structures thereof.
Background technology
In a kind of catalyzer that the inventor uses---the process of caprolactam base magnesium bromide (formula 1), find to rarely have in the prior art the accurate content detecting method of this compounds in exploitation nylon 66 is produced.Method commonly used is the performance of products evaluation assessment, i.e. its industry practice service condition of laboratory simple analog, with the mode of range estimation through observing the catalytic effect of this product with the contrast of standard model, thereby its content is carried out "ball-park" estimate.But the method for this indirect judgement product content has increased quality control and the uncontrollability of actual application of industry in production, brings certain difficulty and risk.
Because the characteristic that the structural singularity of caprolactam base magnesium bromide is rotten with the moisture absorption very easily, adopt the analytical approach of routine, can't accurately detect its content like GC, HPLC.In Jap.P. JP60239462, describe, obtaining product content through synthetic method can analyze through product being carried out NMR, calculates according to the relative peak area of characteristic peak in the analysis of spectra.The inventor adopts the NMR of 400MHz; Deuterium is a solvent for DMSO; The product standard sample is analyzed; δ 3.66ppm described in the patent and δ 1.8ppm characteristic peak do not appear on the nuclear magnetic spectrogram, and in full accord with the spectrogram of raw material caprolactam, so this method fails to reach testing goal.
Summary of the invention
The purpose of this invention is to provide a kind of derivatization method that is used to detect content of lactamyl magnesium salt.This derivative reaction can be used to accurately detect lactamyl magnesium salt (formula 1) content of lactam group magnesium bromide and similar structures thereof.
Formula 1
The method that accurately detects content of lactamyl magnesium salt is following:
Adopt lactamyl magnesium salt product and excessive to the nitro benzyl chloride or to nitro bromobenzyl reaction carrying out derivatization; Generate N-(4-nitrobenzophenone methyl) lactams; N-(4-nitrobenzophenone methyl) lactams to generating carries out quantitative test; Because moles such as lactamyl magnesium salt generate derivant N-(4-nitrobenzophenone methyl) lactams, so can draw the accurate content of lactams magnesium salts in the product by the amount of the derivant that generates.
Because the lactams magnesium salts is a strong nucleopilic reagent; Can with active halogenated hydrocarbons as under the reaction conditions of gentleness, quantitatively reacting to the nitro benzyl chloride or to the nitro bromobenzyl; Lactamyl magnesium salt all is converted into corresponding N-(4-nitrobenzophenone methyl) lactams in the reaction; And, make derivant N-(the 4-nitrobenzophenone methyl) lactams that generates to detect in common HPLC condition owing to have good uv absorption to the nitro benzyl chloride or to the nitro bromobenzyl.
The lactams magnesium salts carries out the reactions step of derivatization:
1) accurately quantitative lactams magnesium salts sample is dissolved in ether solvent;
2) add excessive to the nitro benzyl chloride or to the nitro bromobenzyl, 30-60 ℃ of following insulation reaction,
Reactant liquor is transferred in the volumetric flask, and the reaction dissolvent constant volume promptly gets derivatization solution to be measured.
Wherein the lactams magnesium salts is acyl group magnesium bromide or a caprolactam magnesium bromide in the butyrolactam base magnesium bromide, penta.
Wherein ether solvent is anhydrous THF, tertbutyl ether or ether, is the excessive interpolation of reference to the nitro benzyl chloride or to nitro benzyl bromide with the lactams magnesium salts, and the amount of interpolation enough reacts completely and gets final product.
Carry out the detection of content of lactamyl magnesium salt according to the method described above, this method has accurately, good reproducibility and easy-operating characteristics.
Specific embodiment
The present invention can be further described with following indefiniteness embodiment.
Embodiment 1: caprolactam base magnesium bromide Determination on content
Accurately take by weighing the sample of 1g caprolactam base magnesium bromide (content is about 20%), be dissolved among the anhydrous THF of 20ml, add 0.27g to the nitro benzyl chloride, react 40 ℃ of insulations, stir 1h, reactant liquor is reduced to room temperature, is transferred in the 100ml volumetric flask THF constant volume.The THF standard solution and the drawing curve (object peak area and concentration map) of preparation N-(4-nitrobenzophenone methyl) caprolactam; Behind the Solution H PLC sample introduction to be measured, going out the content that peak area then can calculate caprolactam base magnesium bromide in the sample according to it is 18.2%.
Embodiment 2: the mensuration of valerolactam base content of magnesium chloride
Accurately take by weighing the sample of 1g valerolactam base magnesium chloride (content is about 50%), be dissolved in the 20ml tertbutyl ether, add 0.75g to nitro benzyl bromide, react 40 ℃ of insulations, stir 1h, reactant liquor is reduced to room temperature, is transferred in the 100ml volumetric flask THF constant volume.Preparation N-(4-nitrobenzophenone methyl) valerolactam THF standard solution and drawing curve (object peak area and concentration map), behind the Solution H PLC sample introduction to be measured, going out the content that peak area then can calculate valerolactam base magnesium bromide in the sample according to it is 49.7%.
Embodiment 3: butyrolactam base magnesium iodide Determination on content
Accurately take by weighing the sample of 1g butyrolactam base magnesium iodide (content is about 50%), be dissolved in the 20ml ether, add 0.5g to nitro benzyl bromide, react 40 ℃ of insulations, stir 1h, reactant liquor is reduced to room temperature, is transferred in the 100ml volumetric flask THF constant volume.Prepare N-(4-nitrobenzophenone methyl) butyrolactam THF standard solution and drawing curve (object peak area and concentration map) simultaneously; Behind the Solution H PLC sample introduction to be measured, going out the content that peak area then can calculate butyrolactam base magnesium bromide in the sample according to it is 48.2%.
Claims (3)
1. derivatization method that is used to detect content of lactamyl magnesium salt, wherein, lactamyl magnesium salt is suc as formula shown in (1), and reactions step is:
1) accurately quantitative lactams magnesium salts sample is dissolved in the absolute ether kind solvent;
2) add excessively to the nitro benzyl chloride or to the nitro bromobenzyl, carry out insulation reaction, reactant liquor is transferred in the volumetric flask, and the reaction dissolvent constant volume promptly gets derivatization solution to be measured.
2. derivatization method according to claim 1, wherein, temperature of reaction is 30-60 ℃.
3. derivatization method according to claim 1, wherein, the lactams magnesium salts is butyrolactam base magnesium bromide, valerolactam base magnesium bromide or caprolactam magnesium bromide.
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| CN2009100764160A CN101769906B (en) | 2009-01-07 | 2009-01-07 | Derivatization method for detecting content of lactamyl magnesium salt |
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| CN2009100764160A CN101769906B (en) | 2009-01-07 | 2009-01-07 | Derivatization method for detecting content of lactamyl magnesium salt |
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| CN101769906A CN101769906A (en) | 2010-07-07 |
| CN101769906B true CN101769906B (en) | 2012-07-04 |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991002006A1 (en) * | 1989-07-27 | 1991-02-21 | Daicel Chemical Industries, Ltd. | Polysaccharide derivatives and separating agent |
| US6808933B1 (en) * | 2000-10-19 | 2004-10-26 | Agilent Technologies, Inc. | Methods of enhancing confidence in assays for analytes |
| CN1690686A (en) * | 2004-04-19 | 2005-11-02 | 北京大学 | Blood sample pretreatment method containing aristolochic acid and its lactam components |
| CN1959408A (en) * | 2005-11-01 | 2007-05-09 | 北京大学 | Method for mensurating in vivo sample of containing aristolochic acid and components of lactam categories |
-
2009
- 2009-01-07 CN CN2009100764160A patent/CN101769906B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991002006A1 (en) * | 1989-07-27 | 1991-02-21 | Daicel Chemical Industries, Ltd. | Polysaccharide derivatives and separating agent |
| US6808933B1 (en) * | 2000-10-19 | 2004-10-26 | Agilent Technologies, Inc. | Methods of enhancing confidence in assays for analytes |
| CN1690686A (en) * | 2004-04-19 | 2005-11-02 | 北京大学 | Blood sample pretreatment method containing aristolochic acid and its lactam components |
| CN1959408A (en) * | 2005-11-01 | 2007-05-09 | 北京大学 | Method for mensurating in vivo sample of containing aristolochic acid and components of lactam categories |
Non-Patent Citations (1)
| Title |
|---|
| 龙梅 等.应用RP-HPLC对芳香胺定量分析方法的研究.《北京师范大学学报(自然科学版)》.2000,第36卷(第1期),77-81. * |
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Address after: Beijing City, Haidian District Zhongguancun 100190 South 1 1 horse Baxter 10 storey building Patentee after: Yingli Science and Technology Development Co., Ltd., Beijing Address before: 100084, Beijing Haidian District Qinghua science and Technology Park No. 10 building, purple building, four floor Patentee before: Yingli Science and Technology Development Co., Ltd., Beijing |
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Addressee: Yingli Science and Technology Development Co., Ltd., Beijing Document name: Notification of Termination of Patent Right |
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Granted publication date: 20120704 Termination date: 20170107 |