CN110187026B - 2-propyl heptanol and analysis method of impurities thereof - Google Patents
2-propyl heptanol and analysis method of impurities thereof Download PDFInfo
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Abstract
The invention discloses a method for analyzing 2-propyl heptanol and impurities thereof, which adopts a GC-FID method, and comprises the following gas chromatography detection conditions: a chromatographic column: capillary gas chromatography column, temperature program: the initial temperature is 80 ℃, the temperature is kept for 5min, the temperature is increased to 250 ℃ at the speed of 6 ℃/min, and the temperature is kept for 5min; a detector: a hydrogen flame ionization detector, the detector having a temperature of 300 ℃; the temperature of a sample inlet is 250 ℃; the carrier gas is nitrogen, helium or argon, and the flow rate of the carrier gas is 28mL/min; the gas chromatograph is also provided with a flow splitting device. The method adopts an area normalization method result obtained by detection on a capillary chromatographic column by using an FID detector for analysis, has quick and simple detection process, good precision, reproducibility and stability, and provides an effective way for quality control of 2-propyl heptanol products.
Description
Technical Field
The invention belongs to the technical field of analysis and detection, and particularly relates to an analysis method of 2-propyl heptanol and impurities thereof.
Background
2-propylheptanol (2-PH), is a C 10 Plasticizer raw material alcohol. The raw material for producing 2-PH can be the raffinate C of the cracking device 4 Mixed C by-product of olefin or methanol-to-olefin (MTO) plant 4 Olefins, and the like. Yangzubusf company built a 2-PH device with 8 ten thousand tons/year productivity in 2012, and produced 2-PH by using raffinate oil (mainly butylene contained therein), carbon monoxide and hydrogen as raw materials through carbonyl synthesis, condensation and hydrogenation.
At present, germany Basf company and Yangzi Basf company both adopt a GC method (enterprise standard Q/3201 BYC 50-2018) to analyze 2-PH and impurity content thereof so as to ensure the quality of 2-PH products. In the 2018 period that an OX device (alcohol product device) of Yangze Basff company overhauls a 2-PH device, the 2-PH product detected by the method is unqualified for a long time, and the method is mainly characterized in that the content of one of impurity components, namely 'hexenal', exceeds the standard (shown in an attached drawing 1): the hexenal content is about 0.5% (internal control standard < 0.15%), resulting in a 2-PH reject. Through the analysis of the 2-PH production process, the process experts think that the overproof 'hexenal' is actually the decomposition product glycol of the catalyst in the condensation reaction, and the impurity 5-methyl-2-propyl hexenal in the control standard is not. In order to verify the analysis result, the 2-PH sample is sent to a third-party detection mechanism by the Yangzobasfu company for composition analysis, and the carbonyl value detection shows that the sample does not contain aldehyde group; mass spectrometry analysis showed that the sample contained no hexenal, but rather a diol. The Yangzibasfu company adds the glycol standard substance into a 2-PH product, detects and finds that a chromatographic peak of the standard substance completely overlaps with a chromatographic peak of a suspected impurity component, namely 'hexenal' (see attached figure 2) by adopting the existing 2-PH analysis method, and further confirms that the overproof 'hexenal' detected by the existing method is actually a catalyst decomposition product glycol and does not control the product impurity, namely 5-methyl-2-propyl hexenal in the standard.
From the above results, it can be known that the current analysis method for 2-PH and impurity content thereof cannot accurately control the quality of 2-PH products during driving. By adopting the existing 2-PH analysis method, 5-methyl-2-propyl hexenal serving as an impurity in a control standard cannot be separated from glycol serving as a decomposition product in a catalyst solution, so that the detection result of 5-methyl-2-propyl hexenal in a 2-PH product is higher. At the same time, there is currently no method by basf for determining the decomposition products in the catalyst solution during the start-up of a 2-PH plant. Therefore, the analysis method capable of accurately measuring the 2-PH and the impurity content thereof during the start-up period is created, the defects of the 2-PH measuring method of the basf company can be overcome, and the method is particularly important for ensuring the quality of the 2-PH product during the start-up period and has important economic value.
Disclosure of Invention
The invention aims to: the invention aims to provide an analysis method which can accurately separate glycol and impurity hexenal in a 2-PH product so as to accurately measure 2-propyl heptanol and impurities thereof during the start of a vehicle, aiming at overcoming the defects of the prior art.
The analysis method provided by the invention is suitable for producing the 2-propyl heptanol by using raffinate oil (mainly butene contained in the raffinate oil), carbon monoxide and hydrogen as raw materials through carbonyl synthesis, condensation, hydrogenation and rectification.
The technical scheme is as follows: the purpose of the invention is realized by the following technical scheme:
the invention provides a method for analyzing 2-propyl heptanol and impurities thereof, which adopts a GC-FID method to determine the contents of the 2-propyl heptanol and the impurities thereof, and the gas chromatography detection conditions are as follows:
a chromatographic column: capillary gas chromatography column, temperature program: the initial temperature is 80 ℃, the temperature is kept for 5min, the temperature is increased to 250 ℃ at the speed of 6 ℃/min, and the temperature is kept for 5min;
a detector: a hydrogen flame ionization detector, the detector having a temperature of 300 ℃; the temperature of a sample inlet is 250 ℃;
the carrier gas is nitrogen, helium or argon, and the flow rate of the carrier gas is 28mL/min;
the gas chromatograph is also provided with a flow splitting device.
Preferably, the gas chromatography detection conditions are:
a chromatographic column: 30 m.times.0.25 mm.times.1 μm, DB-1 capillary chromatography column,
sample introduction volume: 0.2 mu L of the suspension liquid is prepared,
flow rate: 1.3mL/min of the reaction kettle,
the carrier gas is nitrogen gas,
air flow rate: the concentration of the active carbon is 400mL/min,
hydrogen flow rate: the concentration of the active carbon is 30mL/min,
the split ratio is as follows: 80:1.
Preferably, the method for analyzing the 2-propyl heptanol and the impurities thereof mainly comprises the following steps:
(1) Sample preparation: directly analyzing after sampling from a 2-propyl heptanol production device;
(2) Working control solution: because the 2-propyl heptenal product contains 5-methyl-2-propyl hexenal, the 2-propyl heptenal solution containing 5-methyl-2-propyl hexenal is taken as a working reference solution; the preparation of a standard solution of the impurity 5-methyl-2-propyl hexenal is not needed;
(3) Glycol standard solution: preparing a glycol standard solution with the concentration of 0.3-1.5 wt% by using 2-propyl heptanol without impurity 5-methyl-2-propyl hexenal as a solvent;
(4) Adding the working reference substance solution in the step (2) into the glycol standard solution in the step (3) to obtain a system applicability solution containing 5-methyl-2-propyl hexenal and glycol; the content of 5-methyl-2-propyl hexenal in the system applicability solution is 0.02-0.05 wt%, and the content of diol is 0.3-1.5 wt%.
(5) The content of 2-propyl heptanol and impurities thereof is determined by GC-FID method.
Preferably, the analysis method further comprises the steps of: after the instrument is stabilized, the error of two continuous sample injection needles is less than 1%, and the 2-propyl heptanol and the impurity content thereof are analyzed by using an area normalization method, wherein the calculation formula is as follows:
in the calculation formula, ci is the content of each component in the sample, and wt%; ai is the peak area of each component;
C H2O is the water content, wt%.
Has the advantages that:
(1) The analysis method can accurately measure the 2-PH and the impurity content thereof, and makes up for the defects of a 2-PH measuring method of Basf company; completely solves the problem that a glycol and a 5-methyl-2-propyl hexenal are not separated during the start of a 2-PH device. The original analysis method is adopted, the decomposition product in the catalyst solution is misjudged as the impurity 5-methyl-2-propyl hexenal, and the number of unqualified days of the 2-PH product is longer; the analysis method provided by the invention helps to shorten the unqualified days of 2-PH products by 5-7 days during the stop and start of the company 2-PH alcohol device, and considerable economic benefits are generated, and through rough measurement and calculation, at least 170 ten thousand yuan can be saved during each start. In addition, the analysis method can be applied to the similar devices, and positive economic benefits are generated.
(2) The analysis method provided by the invention is rapid and simple in detection process, has good precision, reproducibility and stability, and provides an effective way for quality control of 2-PH.
Drawings
FIG. 1 is a GC chromatogram of a 2-propylheptanol product detected by a prior art method; wherein, 12.36min is the chromatographic peak of suspected impurity component, namely 'hexenal' in the 2-PH product.
FIG. 2 is a GC chromatogram of a prior art method of detecting the addition of a diol standard to a 2-PH product; wherein 12.36min is a chromatographic peak of the standard substance and a suspected impurity component, namely 'hexenal', which are completely overlapped.
FIG. 3 is a GC chromatogram of a system-adapted solution tested by the analytical method of the present invention;
wherein 15.423min is chromatographic peak of 4-methyl-2-propyl hexenal, 15.883min is chromatographic peak of 5-methyl-2-propyl hexenal, 15.723min is chromatographic peak of diol, 17.738min is chromatographic peak of 2-propyl heptanol.
FIG. 4 is a GC chromatogram of a 2-PH product detected by the analytical method of example 1 of the present invention;
wherein 15.734min is chromatographic peak of diol, 17.753min is chromatographic peak of 2-propylheptanol.
Detailed Description
The technical solution of the present invention is described in detail below with reference to specific examples and drawings, but the scope of the present invention is not limited to the examples.
The instrument comprises the following steps: agilient-6890 gas chromatograph (FID detector, agilent USA)
Sample preparation: the 2-PH product is from Yangzi Basff; the working control 2-propylheptenal product is from Yangze Pasteur company; the glycol as the decomposition product in the catalyst solution is from TCI-Chiese (Shanghai) chemical industry development limited company, the content is more than 97 percent, and the batch number is TU5YE-01.
In the 2-PH internal control standard, the internal control standard of the impurity 5-methyl-2-propyl hexenal is required to be less than 0.15 percent, and the product is qualified.
Example 1:
gas chromatography conditions:
a chromatographic column: 30m × 0.25mm × 1 μm, DB-1 capillary chromatography column
The injection port temperature is 250 ℃, and the detector temperature is 300 ℃;
the carrier gas is nitrogen, and the flow rate of the carrier gas is 28mL/min; air flow rate: 400mL/min, hydrogen flow rate: 30mL/min;
the split ratio is as follows: 80:1.
Temperature rising procedure: the initial temperature is 80 ℃, the temperature is kept for 5min, the temperature is increased to 250 ℃ at the speed of 6 ℃/min, and the temperature is kept for 5min; sample introduction volume: 0.2 mu L; flow rate: 1.3mL/min.
Analysis time: 38.5min.
The test method comprises the following steps:
(1) Sample preparation: 2-PH samples are collected from a 2-propyl heptanol production device and then directly analyzed;
(2) Working control solution: 0.1719g of a 2-propylheptenal solution containing 4-methyl-2-propylhexenal with a known concentration of 3.676wt% and 5-methyl-2-propylhexenal with a concentration of 2.789wt% is accurately weighed as a working reference solution;
(3) Glycol standard solution: using a 2-PH apparatus, 2-PH (2-propylheptanol) product free of 5-methyl-2-propylhexenal as an impurity as a solvent, a 1.292wt% strength standard solution was prepared using a commercially available diol standard (0.3982 g of the standard was weighed out and diluted to 29.8972 g).
(4) Adding the working reference substance solution in the step (2) into the standard solution in the step (3) (the total weight is 30.0691 g), so as to obtain a system applicability solution containing 5-methyl-2-propyl hexenal and diol;
(5) The content was determined by GC-FID.
After the instrument is stabilized, the error of two continuous sample injection needles is less than 1%, and the 2-propyl heptanol and the impurity content thereof are analyzed by using an area normalization method, wherein the calculation formula is as follows:
in the calculation formula, ci is the content of each component in the sample, and wt%; ai is the peak area of each component;
C H2O is the water content, wt%.
The content of the main component in the system applicability solution as a sample was measured by the analysis method of the present invention, and the measurement results are shown in table 1.
The GC chromatogram of the system-compatible solution is shown in FIG. 3, wherein 15.423min is the chromatographic peak of 4-methyl-2-propyl hexenal, 15.883min is the chromatographic peak of 5-methyl-2-propyl hexenal, 15.723min is the chromatographic peak of diol, and 17.738min is the chromatographic peak of 2-propyl heptanol.
TABLE 1 GC determination of the major components in the system suitability solution
And (3) measuring content calculation: assay content = mean dilution factor
For 4-methyl-2-propyl hexenal and 5-methyl-2-propyl hexenal in a system suitability solution, the dilution factor =30.0691/0.1719=174.92; for the glycol and 2-propylheptanol in the system suitability solution, the dilution factor =30.0691/29.8972=1.01.
The contents of each main component in the working control solution and the standard solution before dilution (i.e. the measured contents in table 2) were obtained by conversion of the dilution factor, i.e. by multiplying the GC measured value by the dilution factor. In Table 2, "actual content" refers to the original concentration of the working control solution (GC measurement) and the concentration of the standard solution.
TABLE 2 comparison of the results of the determination of the principal components of the process of the invention with the data of the actual contents thereof
| Determination of content (%) | Actual content (%) | Relative error% | |
| 4-methyl-2-propylhexenal | 3.673 | 3.676 | -0.09 |
| Diols | 1.274 | 1.292 | -0.47 |
| 5-methyl-2-propylhexenal | 2.974 | 2.789 | 6.63 |
| 2-propylheptanol | 92.330 | 92.803 | -5.10 |
As can be seen from Table 2, the method of the present invention not only can effectively separate each impurity, especially completely separate 5-methyl-2-propyl hexenal from diol, but also can accurately determine each impurity content; from the measurement result, the process requirement can be completely met, and the measurement result and the actual content also meet the sample recovery rate measurement requirement in the analysis method: 90-110 percent.
The directly sampled 2-PH product is detected by adopting the analysis method, and the content of each component is directly obtained from GC; and the diol was separated from 5-methyl-2-propylhexenal.
The results of the 2-PH test are shown in Table 3:
FIG. 4 is a GC chromatogram of a 2-PH product; wherein 15.734min is chromatographic peak of diol, 17.753min is chromatographic peak of 2-propylheptanol.
TABLE 3 content of major ingredients in the PH product
According to the detection result, the analysis method disclosed by the invention not only can be used for detecting the 2-PH product containing the impurities, but also can be used for effectively detecting the new impurity glycol in the 2-PH product, and the chromatographic peaks of the impurities are well separated, the quantification is also accurate, and the analysis requirements of process data can be completely met. From the measurement results, the measurement results and the actual content also meet the sample recovery rate measurement requirements in the analysis method: 90-110 percent.
Repeatability:
the same operator uses the same instrument and under the same operating conditions, the same sample is repeatedly measured for more than two times by using a normal and correct operating method, and the relative deviation of the measured values is not more than 2%.
Stability:
different operators use different instruments to measure the same sample, and the relative deviation of the two measurement results is not more than 5%.
Example 2: standard addition recovery experiment for determining glycol by adopting analysis method of the invention
A2-PH (2-propylheptanol) product from a 2-PH apparatus was used as a solvent to prepare a 0.3518% standard solution using a commercially available diol standard.
Determination of diols:
the results of the three measurements were 0.338%, 0.336%, and 0.338%, respectively, and the recovery rates were: 95.89 percent; RSD (relative mean deviation): 0.3% (< 2%).
The analysis method provided by the invention is rapid and simple in detection process, has good precision, reproducibility and stability, and provides an effective way for quality control of 2-PH.
As noted above, while the present invention has been shown and described with reference to certain preferred embodiments, it is not to be construed as limited thereto. Various changes in form and detail may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (1)
1. The method for analyzing the 2-propyl heptanol and the impurities thereof is characterized by comprising the following steps of:
(1) 2-PH samples are collected from a 2-propyl heptanol production device and then directly analyzed;
(2) The GC-FID method is adopted to determine the content of the 2-propyl heptanol and the impurity thereof, and the gas chromatography detection conditions are as follows:
a chromatographic column: 30m × 0.25mm × 1 μm, DB-1 capillary chromatography column, injection volume: 0.2 mu L; flow rate: 1.3mL/min; temperature rising procedure: the initial temperature is 80 ℃, the temperature is kept for 5min, the temperature is increased to 250 ℃ at the speed of 6 ℃/min, and the temperature is kept for 5min;
a detector: a hydrogen flame ionization detector, the detector having a temperature of 300 ℃; the temperature of a sample inlet is 250 ℃;
the carrier gas is nitrogen, and the flow rate of the carrier gas is 28mL/min;
air flow rate: 400 The volume ratio of the water to the water is mL/min,
hydrogen flow rate: 30 The concentration of the active carbon is mL/min,
the gas chromatograph is also provided with a flow dividing device, and the flow dividing ratio is as follows: 80;
(3) After the instrument is stabilized, the error of two continuous sample injection needles is less than 1%, and the 2-propyl heptanol and the impurity content thereof are analyzed by using an area normalization method, wherein the calculation formula is as follows:
in the calculation formula, ci is the content of each component in the sample, and wt%; ai is the peak area of each component; c H2O Is the water content, wt%;
the impurities include 4-methyl-2-propylhexenal, 5-methyl-2-propylhexenal, 2-propylheptenol, 4+5 methyl-2-propylhexanol, 2-propylheptenal, 2-isopropylheptanol.
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