CN109239121B - Method for measuring water content of triethylene glycol dinitrate by nuclear magnetic resonance hydrogen spectrum - Google Patents
Method for measuring water content of triethylene glycol dinitrate by nuclear magnetic resonance hydrogen spectrum Download PDFInfo
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- CN109239121B CN109239121B CN201811249906.1A CN201811249906A CN109239121B CN 109239121 B CN109239121 B CN 109239121B CN 201811249906 A CN201811249906 A CN 201811249906A CN 109239121 B CN109239121 B CN 109239121B
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Abstract
The invention discloses a method for measuring the moisture content of triethylene glycol dinitrate (TEGDN) by a nuclear magnetic resonance hydrogen spectrum, which realizes the quantitative detection of trace moisture based on a nuclear magnetic hydrogen spectrum internal standard method and comprises the following specific steps: (1) preparing an internal standard substance sample solution and detecting a nuclear magnetic resonance hydrogen spectrum; (2) adding a triethylene glycol dinitrate sample to be detected and detecting a nuclear magnetic resonance hydrogen spectrum; (3) attributing each characteristic peak in the nuclear magnetic resonance hydrogen spectrum, determining the characteristic peak of water and the characteristic peak of an internal standard substance, respectively integrating, and substituting into a correlation formula to calculate the corresponding water content. The method has the advantages of simple and convenient operation, small sample amount, good repeatability and the like, can quickly carry out quantitative detection on the moisture content in the triethylene glycol dinitrate (TEGDN), and can pertinently solve the key problem of related quality control in the application of explosives and powders.
Description
Technical Field
The invention belongs to the field of energetic material measurement and detection, and particularly relates to a method for measuring the water content of triethylene glycol dinitrate by using a nuclear magnetic resonance hydrogen spectrum, belonging to the field of explosive product analysis and detection.
Background
Nitrate is used as an excellent plasticizer, and because the oxygen balance is better, the combustion and explosion performance is good, the nitrate is widely applied to the fields of double-base propellants and composite propellants at present. The plasticizer is a good plasticizer of the nitrocellulose, is a main energy component in the composition of the propellant, plays an important role in making the semi-rigid nitrocellulose into an extrudable material and reducing the glass transition temperature, and is an indispensable important component in the propellant. Triethylene glycol dinitrate (TEGDN) is taken as an energetic plasticizer which is researched enthusiastically in recent years, and has good application prospect as the energetic plasticizer in a new generation of high-energy propellant due to the excellent performances of low price, low glass transition temperature, good low-temperature mechanical property, low burning rate of basic components and the like.
Due to the diffusion of moisture in the atmosphere and the non-drying of raw materials, the produced triethylene glycol dinitrate usually contains a certain amount of moisture, and the moisture content in the triethylene glycol dinitrate has great influence on the important physical and chemical properties such as stability and compatibility. It has been found that the higher the water content of the nitrate-based high-energy binder, the lower the stability thereof, at the same storage time. The requirement of the use specification of a certain mixed explosive is that the moisture content is not higher than 0.5 percent, so that the moisture content in the mixed explosive needs to be strictly controlled in the actual production and storage processes, and the accurate detection of the moisture content in the triethylene glycol dinitrate is realized. Common trace moisture detection methods include a drying method, a dryer method, a karl fischer method, a near infrared spectroscopy method, and the like, but due to the characteristics of high energy, high sensitivity, and high risk of triethylene glycol dinitrate, a moisture detection method has been specifically demanded: (1) the sample amount is required to be as small as possible so as to reduce the potential safety hazard in the detection process, and in this point, although the traditional drying method and the traditional dryer are used as a standard method for detecting the moisture of the nitrate product, the traditional drying method and the traditional dryer are used as a constant analysis method (the sample amount for testing is generally 5-10 g), obviously, the sample amount is too large so that the great potential safety hazard exists in the taking and testing process; (2) in the test process, external force effects such as friction, static electricity and the like are avoided as much as possible so as to avoid explosion of the high-sensitivity nitrate under the action of external energy. In a common Karl Fischer moisture test method, current is required to be generated in the test process to ionize iodine into iodine ions, and the reaction process is monitored through electric quantity, so that the generation of current and charge in the test process cannot be avoided, and obviously, the use limitation exists; (3) the test method should be as simple and rapid as possible and have high sensitivity. The near infrared spectroscopy is used as a relative measurement method, the test sensitivity is high, but calibration of the near infrared spectroscopy needs standard substances in one-to-one correspondence, corresponding working curves are drawn, corresponding quantitative analysis work is high in cost and complex in method, and the requirement for simple and rapid test is limited. (4) Other additives and reagents and the influence of moisture in environmental conditions on the measurement result should be avoided or excluded as much as possible in the test process. The Quantitative nuclear magnetic resonance (qNMR) technology does not need a reference substance of an object to be detected, the sample pretreatment step is simple and quick, the detection efficiency can be obviously improved, and the Quantitative nuclear magnetic resonance (qNMR) technology is successively recorded and recorded by United states pharmacopoeia, British pharmacopoeia, European pharmacopoeia and Chinese pharmacopoeia (2010 edition) in recent years. In recent years, due to the high sensitivity of the hydrogen nuclear magnetic resonance spectroscopy quantitative technology, the application of the qNMR technology is more and more extensive, and the method is widely applied to the aspects of bulk drugs, pharmaceutical preparations, residual solvent determination, sample component ratio determination and the like.
Disclosure of Invention
Aiming at the requirement of accurate quantification of the content of explosives and powders at the present stage, the invention provides a method for measuring the moisture content of triethylene glycol dinitrate by using a nuclear magnetic resonance hydrogen spectrum. The technical scheme is as follows:
(1) accurately weighing 10-20mg (accurate to 0.1mg) of internal standard substance, adding 0.5-0.6ml of deuterated solvent for dissolving, transferring into a nuclear magnetic tube, and sealing with a sealing film. And placing the prepared sample solution in an ultrasonic oscillator for oscillation for 10-20s, and then carrying out nuclear magnetic resonance hydrogen spectrum test on the sample. The quantitative nuclear magnetic test conditions are as follows: the resonance frequency of a nuclear magnetic spectrometer is 400-800 MHz, the temperature is 20-35 ℃, the delay time is 20-50 s, the pulse angle is 30-90 degrees, and the sampling frequency is 32-128 times.
(2) And taking down the tested nuclear magnetic sample tube, adding 20-40mg of triethylene glycol dinitrate, adding a sealing film for sealing, and oscillating by using an ultrasonic oscillator until the mixture is uniformly mixed. And (3) performing the nuclear magnetic resonance hydrogen spectrum test on the sample added with the triethylene glycol dinitrate again, wherein the quantitative nuclear magnetic test condition is consistent with that in the previous step.
(3) After the test is finished, attributing characteristic peaks in the nuclear magnetic resonance hydrogen spectrums respectively obtained by the two tests, determining the characteristic peak of water and the characteristic peak of an internal standard substance, respectively integrating, wherein the integration method comprises the steps of leveling a spectrogram base line, and removing the characteristic peaks13And C, integrating after the satellite peak, and calculating 3 times to obtain an average value. And (3) respectively obtaining the integral area of the characteristic peak of the water and the integral area of the characteristic peak of the internal standard substance, and substituting the data into the formula (a) to obtain the corresponding impurity content.
In the formula:
Px-the mass percentage of moisture in the sample to be tested, expressed in%;
PS-the value of the purity of the internal standard, expressed in%;
ms-mass of added internal standard in mg;
m-triethylene glycol dinitrate sample adding mass, unit mg;
Ms-relative molecular mass of internal standard;
Mx-the relative molecular mass of water;
Hs-1 mole of the number of resonating nuclei on the functional group of the internal standard signature;
Hx-the number of resonant nuclei on 1 mole of water-signaling functional group;
As-peak area of the internal standard characteristic signal peak;
A1peak area of the water characteristic signal peak of the sample without addition of triethylene glycol dinitrate;
A2-peak area of water characteristic signal peak of sample added with triethylene glycol dinitrate;
preferably, in the method for detecting the moisture content in the triethylene glycol dinitrate sample, in the step (1), the internal standard substance is benzene, p-dichlorobenzene, hexamethyldisiloxane high-purity product or standard substance, and the deuterated solvent is deuterated dimethyl sulfoxide (DMSO). Benzene, p-dichlorobenzene and hexamethyldisiloxane do not react with the triethylene glycol dinitrate component, the dissolubility is good, high-purity products or purity standard substances can be obtained easily, all hydrogen in the substances is in the same chemical environment, namely, only one group of characteristic peaks exist in a nuclear magnetic resonance hydrogen spectrum, and the method is suitable for the requirements of internal standard substances of the quantitative nuclear magnetic hydrogen spectrum of the system. The selection of the deuterated solvent is mainly based on the solvent properties of an internal standard substance and a sample, the solvent properties of triethylene glycol dinitrate and the internal standard substance are integrated, deuterated acetone or deuterated dimethyl sulfoxide can be selected as the solvent, but in the experiment, under the conditions that the sample amount is close and the water content is close, the water peak in the deuterated DMSO solvent sample is a single absorption peak with a sharp and symmetrical peak shape, the water characteristic peak in the deuterated acetone solvent sample is an asymmetrical double peak, and the analysis is that the deuterium atom in the deuterated acetone and the hydrogen atom in the water can generate rapid exchange, namely, the content of the water molecule with one hydrogen atom replaced by the deuterium atom is increased, and finally the water peak in a nuclear magnetic spectrum is split. When nuclear magnetism characteristic peak integral calculation is carried out, symmetrical single peak generates smaller integral calculation error compared with the single peak. Meanwhile, considering that the volatility of acetone may affect the stability of a nuclear magnetic spectrum of a sample, and comprehensively analyzing and considering that deuterated dimethyl sulfoxide is selected as a solvent system for quantitative nuclear magnetic detection of a triethylene glycol dinitrate system.
Preferably, the amount of triethylene glycol dinitrate weighed in the experiment should be 2-3 times that of the internal standard substance. The control of the condition is because an important condition in the quantitative nuclear magnetic test is that the ratio of the integral area values of two compared characteristic peaks does not differ by a multiple too much, and the control is found in the specific practical operation to be between 1:10 and 10:1, and the error of the quantitative integration on the final result is small. Therefore, the water content in the triethylene glycol dinitrate sample, the molecular weight of the internal standard substance and other factors are comprehensively considered, the condition that the sample weighing amount of the triethylene glycol dinitrate is 2-3 times of that of the internal standard substance is determined, the ratio of the characteristic peak area to the water peak area of the internal standard substance can be controlled in the range, and the quantitative nuclear magnetic detection method is used as a proper quantitative nuclear magnetic detection basis.
Because the moisture content measurement has the particularity compared with the measurement of other impurities, namely, the existence of trace moisture in the deuterated solvent, the internal standard substance or the air, the water contained in the parts is removed in the test process, and the trace moisture content in the triethylene glycol dinitrate sample is accurately measured. The method is characterized in that an integral difference method is adopted to accurately calculate the water content in a sample, namely, a triethylene glycol dinitrate is not added, an internal standard substance sample is only added into a deuterated solvent for quantitative nuclear magnetic detection to obtain an integral area value of a water peak in the system relative to an internal standard substance characteristic peak, then a triethylene glycol dinitrate sample is accurately weighed and added into the nuclear magnetic sample, then quantitative nuclear magnetic detection is carried out under the same experimental conditions, and the integral area value of the water peak in the system relative to the internal standard substance is further obtained. By the mechanism of quantitative nuclear magnetic test, although the integral area of the characteristic peak in the nuclear magnetic spectrogram is not an absolute value and theoretically has no comparability in different spectrograms, because the internal standard substance values contained in two tests are unchanged and the test conditions are the same, the peak height, the peak shape and the peak position of the internal standard substance are all kept unchanged under the condition that the instrument test state is stable, the integral area value of the water peak relative to the characteristic peak of the internal standard substance is increased in direct proportion to the water content value contained in the triethylene glycol dinitrate, and the calculation can be carried out through a quantitative nuclear magnetic formula. Meanwhile, the higher the resonance frequency of the nuclear magnetic resonance spectrometer, namely the higher the power, the resolution, the sensitivity and the sampling stability are obviously improved correspondingly. Therefore, for the analysis and verification of trace moisture in the triethylene glycol dinitrate, the accuracy and the stability of detection results of nuclear magnetic spectrometers with different powers are comprehensively compared, and an 800M nuclear magnetic spectrometer is optimally selected for quantitative detection, so that a nuclear magnetic hydrogen spectrum with better signal-to-noise ratio can be obtained.
The delay time is used as an important parameter of quantitative nuclear magnetism, the final quantitative integration result is directly influenced, and due to the fact that various compounds exist in a nuclear magnetism sample to be detected, chemical structures are different, the relaxation of protons of different protons is different, and finally the fact that Boltzmann balance needs to be recovered is different after the protons are excited under the action of a magnetic field of a nuclear magnetism spectrometer within the same time, so that the acquired signals are protons in an unreturned equilibrium state due to the fact that the delay time is too short, the characteristic peak is incomplete, and the quantitative result is inaccurate. Through a series of targeted nuclear magnetic behavior researches on a triethylene glycol dinitrate system, the accuracy and reproducibility of experimental results and the convenience and rapidness of a detection method are considered in multiple tests, the delay time of 20s-50s is determined and selected finally, the parameter range can ensure that the internal standard substance and water are completely relaxed and the equilibrium state is recovered, and therefore the accuracy of water quantification by taking the content of the internal standard substance as a reference is ensured.
The weighing amount of the triethylene glycol dinitrate is 20-40mg, because although the requirements of improving the quantitative accuracy and reducing errors are met, a high-concentration solution is prepared as much as possible to achieve a better signal-to-noise ratio of a spectrogram, but at the same time, the concentration of the sample solution is too high, which may cause uneven distribution of solutes in the solution and overlarge viscosity to widen the spectral line, and the dosage of the triethylene glycol dinitrate is reduced as much as possible due to the safety problem. Therefore, the sample weighing is limited to 20-40mg, and the better signal-to-noise ratio is achieved while the uniformity and the fluidity of the solution are kept.
Compared with the prior art, the method for detecting the water content of the triethylene glycol dinitrate has the main beneficial effects that: (1) the sample amount for testing is in milligram level, the using amount is small, and the potential safety hazard caused by large constant analysis using amount in the traditional water detection method is effectively avoided; (2) the testing method is lossless and basically has no external force action such as friction, static electricity and the like, and the problem that the high-sensitivity nitrate is sensitive and easy to explode under the action of external energy is solved; (3) the method has the advantages of simple and rapid test, rapid batch completion, high experimental precision, good reproducibility, high sensitivity, and no need of standard reference substance or working curve drawing; (4) the method combines an internal standard method and an integral difference method, and effectively removes the influence of residual moisture in reagents except the sample on the test. The method for quantifying the moisture content of the nuclear magnetic resonance hydrogen spectrum is suitable for analyzing and detecting high-energy, high-sensitivity and high-risk samples such as triethylene glycol dinitrate, and provides a quick quantitative method and thought for analyzing and detecting trace moisture of the same type of explosive products.
Drawings
FIG. 1 is nuclear magnetic hydrogen spectrum of triethylene glycol dinitrate
Detailed Description
In order to make the technical solutions of the present invention better for those skilled in the art, the technical solutions of the present invention are further described in detail below with reference to some specific embodiments.
Example 1
Triethylene glycol dinitrate1Establishment and assignment of H NMR spectra
1.1 Instrument and sample
Bruker Ascend 800 superconducting nuclear magnetic resonance spectrometer (Bruker, germany); a one-hundred-thousandth balance model Mettler Toledo XP6 (Mettler corporation, switzerland); deuterated dimethyl sulfoxide (deuteration > 99.8%, CIL corporation, USA); 5mm standard nuclear magnetic sample tubes (NORELL, USA); hexamethyldisiloxane high purity (Annaiji chemistry, purity 99%); triethylene glycol dinitrate (Xian modern chemical research institute)
1.2 preparation and determination of samples to be determined
Accurately weighing 15mg of internal standard hexamethyldisiloxane in a 5mm nuclear magnetic tube, adding 0.6ml of deuterated dimethyl sulfoxide, mixing uniformly, sealing with a sealing film, and directly applying the prepared nuclear magnetic sample to a 5mm nuclear magnetic tube1H NMR measurement. After the test is finished, the nuclear magnetic sample tube which is finished is taken down, 30mg of triethylene glycol dinitrate is added and fully mixed, a sealing film is added for sealing, and then the sample is subjected to the same test conditions1H NMR testing, wherein the test parameters and conditions are: frequency was observed at 800.3MHz, temperature was measured at 300K, 90 pulse, spectral width 3 μ s, data point sampled 65536, scan number 64, delay time 40 s.
1.3 samples1H NMR Spectrum analysis
According to1H NMR spectrum literature data, chemical properties of triethylene glycol dinitrate are integrated, and the obtained product is detected by using a Topspin 3.5 pair1The H NMR spectrum is subjected to calibration, baseline correction and phase adjustment, and corresponding attribution is carried out according to the coupling column conditions and the chemical shift values of proton signal peaks, as shown in the following Table 1. Water proton signal peak of chemical shift δ 3.33, and chemical shift δ 7.37The benzene proton signal peak is well separated from other signal peaks, is symmetrical and uniform, and meets the basic condition of quantitative nuclear magnetism.
TABLE 1 triethylene glycol dinitrate nuclear magnetic hydrogen spectrum peak attribution table
1.4 methodological considerations
Stability: taking the same triethylene glycol dinitrate sample, respectively carrying out the steps of 0, 2, 4, 6, 8 and 12 hours according to the experimental conditions and the method1H NMR experiment, recording the relative integral area of water peak to calculate the relative content of water in the sample, and calculating RSD value;
repeatability: taking 6 parts of the same batch of triethylene glycol dinitrate, and carrying out the test according to the experimental conditions and the method1H NMR experiment, recording the relative integral area of water peak to calculate the relative content of water in the sample, and calculating RSD value;
precision: taking the same triethylene glycol dinitrate sample, continuously measuring for 6 times according to the experimental conditions and the method, recording the relative integral area of water peaks so as to calculate the relative content of water in the sample, and calculating the RSD value;
and (3) standard addition recovery rate: taking the same batch of triethylene glycol dinitrate samples, and carrying out the test according to the experimental conditions and the method1After the H NMR experiment, 3mg, 5mg of pure water were then added precisely, and each time after the addition of pure water, the procedure was followed as above1And H NMR experiments, recording the relative integral area of a water peak to calculate the relative content of water, and calculating the recovery rate.
And (3) linear verification: taking the same batch of triethylene glycol dinitrate samples, precisely weighing about 20mg, 25mg, 30mg and 40mg of the samples, and respectively carrying out the test according to the experimental conditions and the method1H NMR experiment to record the relative integrated area of water peaks to calculate waterAnd (4) carrying out statistics on the linearity of the test result by dividing the relative content.
The experimental results are shown in table 2 below, and data show that the method has good linear relationship, precision, stability and repeatability, and the benchmarking recovery rate value shows that the method also has good accuracy.
TABLE 2 NMR Hydrogen Spectroscopy for determination of moisture in triethylene glycol dinitrate methodology
Example 2
Nuclear magnetic resonance hydrogen spectrum determination of water content in different batches of triethylene glycol dinitrate
Accurately weighing 12mg of internal standard hexamethyldisiloxane in a 5mm nuclear magnetic tube, adding 0.6ml of deuterated dimethyl sulfoxide, mixing uniformly, sealing with a sealing film, and directly applying the prepared nuclear magnetic sample to a 5mm nuclear magnetic tube1H NMR test, the test parameters and conditions are as follows: frequency was observed at 800.3MHz, temperature was measured at 300K, 90 pulse, spectral width 3 μ s, data point sampled 65536, scan number 128, delay time 40 s. Taking down the tested nuclear magnetic sample tube, adding 25mg of triethylene glycol dinitrate, fully mixing, sealing by a sealing film, and carrying out the test on the sample under the same test conditions1H NMR measurement. Three different batches of triethylene glycol dinitrate samples were tested according to the same method, nuclear magnetic resonance spectrograms were recorded, and the water content was calculated, with the results shown in table 3 below.
TABLE 3 determination of moisture content of different batches of triethylene glycol dinitrate
| Batch number | Water content/% |
| 180321 | 0.862 |
| 180508 | 0.632 |
| 180521 | 0.836 |
It should be added that the above-mentioned embodiments describe the moisture detection method of triethylene glycol dinitrate by way of illustration and not limitation, and the above examples 1-2 are not all examples that can be implemented in this patent, and further more examples can be specifically mentioned according to the limited scope, therefore, modifications and changes without departing from the general concept of the present invention are within the protection scope of the present invention.
The invention establishes the nuclear magnetic resonance hydrogen spectrum trace moisture detection method of triethylene glycol dinitrate, solves the problems of large sample dosage, safety, requirement of one-to-one corresponding standard substance, complicated operation of the method and the like of the traditional detection method, has small dosage of the sample for testing, no damage to the test method, basically no external force action such as friction, static electricity and the like, effectively avoids the problems of sensitivity and easy explosion of the traditional moisture detection method due to large dosage of constant analysis and high sensitivity nitrate under the action of external energy, is simple, convenient and quick to test, can be quickly completed in batches, has high experimental precision and good reproducibility, and simultaneously combines an internal standard method and an integral difference method to effectively remove the influence of residual moisture in reagents except the sample on the test. The method is particularly suitable for detecting the triethylene glycol dinitrate sample with high energy, high sensitivity and high risk, and provides an effective analysis method and means for quality control of explosive raw materials and products.
Claims (4)
1. A method for measuring the moisture content of triethylene glycol dinitrate by nuclear magnetic resonance hydrogen spectrum is characterized by comprising the following specific steps:
(1) weighing 10-20mg of internal standard substance, adding 0.5-0.8 ml of deuterated reagent for dissolving, transferring into a nuclear magnetic tube, sealing by using a sealing film, placing the prepared sample solution into an ultrasonic oscillator for oscillation for 10-20s, and then carrying out nuclear magnetic resonance hydrogen spectrum test on the sample, wherein the quantitative nuclear magnetic test conditions are as follows: the resonance frequency of a nuclear magnetic spectrometer is 400-800 MHz, the temperature is 20-35 ℃, the delay time is 20-50 s, the pulse angle is 30-90 degrees, and the sampling frequency is 32-128 times;
(2) taking down the tested nuclear magnetic sample tube, adding 20-40mg of triethylene glycol dinitrate, sealing by using a sealing film, oscillating by using an ultrasonic oscillator, and performing nuclear magnetic resonance hydrogen spectrum test on the sample added with the triethylene glycol dinitrate again, wherein the quantitative nuclear magnetic test condition is consistent with that of the previous step;
(3) after the test is finished, attributing characteristic peaks in the nuclear magnetic resonance hydrogen spectrums obtained in the first step and the second step respectively, determining the characteristic peaks of water and the characteristic peaks of an internal standard substance, and integrating the characteristic peaks respectively, wherein the integration method comprises the steps of removing the characteristic peaks after the base line of the spectrogram is leveled13And C, integrating after the satellite peak, calculating 3 times, taking an average value, respectively obtaining the water characteristic peak integral area and the internal standard substance characteristic peak integral area, and substituting the data into the following formula to obtain the corresponding water content:
wherein P isxIs the mass fraction of water in the sample to be measured, PSIs the purity value of the internal standard, msFor the mass of the added internal standard, M is the mass of the added triethylene glycol dinitrate sample, MsRelative molecular mass of internal standard, MxIs the relative molecular mass of water, HsNumber of resonating nuclei on functional group which is a characteristic signal of 1 mole of internal standard, HxNumber of resonant nuclei on functional groups that produce a signal for 1 mole of water, AsIs the peak area of the characteristic signal peak of the internal standard substance, A1The peak area of the water characteristic signal peak of the sample to which triethylene glycol dinitrate is not added, A2The peak area of the water characteristic signal peak of the sample added with triethylene glycol dinitrate is shown.
2. The method for measuring the moisture content of triethylene glycol dinitrate by nuclear magnetic resonance hydrogen spectroscopy according to claim 1, wherein the deuterated reagent is deuterium-enriched dimethyl sulfoxide.
3. The method for measuring the moisture content of triethylene glycol dinitrate by nuclear magnetic resonance hydrogen spectrum according to claim 1, wherein the internal standard substance is benzene, p-dichlorobenzene or hexamethyldisiloxane which is high-purity or standard substance.
4. The method for measuring the moisture content of triethylene glycol dinitrate according to claim 3, wherein the loading mass of triethylene glycol dinitrate is 2-3 times that of the internal standard substance.
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