CN110187026A - A kind of analysis method of 2- propyl enanthol and its impurity - Google Patents
A kind of analysis method of 2- propyl enanthol and its impurity Download PDFInfo
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- CN110187026A CN110187026A CN201910463474.2A CN201910463474A CN110187026A CN 110187026 A CN110187026 A CN 110187026A CN 201910463474 A CN201910463474 A CN 201910463474A CN 110187026 A CN110187026 A CN 110187026A
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
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- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
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- G01N30/06—Preparation
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- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
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- G01N30/68—Flame ionisation detectors
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
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- G01N30/86—Signal analysis
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N2030/022—Column chromatography characterised by the kind of separation mechanism
- G01N2030/025—Gas chromatography
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Abstract
The invention discloses the analysis methods of a kind of 2- propyl enanthol and its impurity, and using GC-FID method, gas chromatographic detection condition is as follows: chromatographic column: capillary gas chromatographic column, temperature program: 80 DEG C of initial temperature, 5min is kept, 250 DEG C is warming up to the rate of 6 DEG C/min, keeps 5min；Detector: flame ionization ditector, 300 DEG C of the temperature of the detector；250 DEG C of injector temperature；Carrier gas is nitrogen, helium or argon gas, flow rate of carrier gas 28mL/min；Gas chromatograph is also configured with part flow arrangement.This method uses the area normalization method result detected on capillary chromatographic column with fid detector to be analyzed, detection process is fast simple, with good precision, reproducibility and stability, effective way is provided for the quality control of 2- propyl enanthol product.
Description
Technical field
The invention belongs to technical field of analysis and detection, and in particular to the analysis method of a kind of 2- propyl enanthol and its impurity.
Background technique
2- propyl enanthol (2-PH) is a kind of C10Plasticizer raw alcohol.The raw material of production 2-PH may be from cracker
Raffinate C4The mixing C of alkene or methanol-to-olefins (MTO) device by-product4Alkene etc..Yangtze BASF AG built up in 2012
The 2-PH device of 80000 tons/year of production capacities, to raffinate oil (butylene mainly contained therein), carbon monoxide and hydrogen as raw material, warp
Carbonylation synthesis, condensation plus hydrogen produce 2-PH.
Currently, BASF Aktiengesellschaft and Yangtze BASF AG are all made of GC method (company standard Q/3201 BYC
2-PH and its impurity content 50-2018) are analyzed, to guarantee 2-PH product quality.Yangtze BASF AG OX device in 2018
During (alcoholic product device) general overhaul 2-PH device is driven, the 2-PH product detected using the method is not conformed to for a long time
Lattice, it is exceeded (see attached drawing 1) to be characterized primarily by a kind of " hexenoic aldehyde " content of impurity composition: hexene aldehyde is about 0.5% (internal control mark
Quasi- < 0.15%), cause 2-PH product unqualified.By the analysis to 2-PH production technology, technique expert thinks exceeded " oneself
Olefine aldehydr " is actually the decomposition product glycol of catalyst in the condensation reaction, and the product impurity 5- methyl -2- in non-controlling standard
Propyl hexenoic aldehyde.For verify this analysis as a result, Yangtze BASF AG by 2-PH sample send to third party testing agency carry out at
Divide and dissect, carbonyl value detection shows sample without aldehyde radical；Mass spectral analysis shows that sample is free of hexenoic aldehyde, but contains one kind two
Alcohol.The glycol standard substance is added in 2-PH product for Yangtze BASF AG, is detected and is found using existing 2-PH analysis method
The chromatography peak complete-superposing (see attached drawing 2) of the chromatographic peak of standard substance and doubtful impurity composition a kind of " hexenoic aldehyde ", is further demonstrate,proved
Exceeded " hexenoic aldehyde " that real existing method detects is actually catalyst decomposition products glycol, and the product in non-controlling standard
Impurity 5- methyl-2-propyl hexenoic aldehyde.
By conclusions it is found that the analysis method of current 2-PH and its impurity content, can not accurately control 2- during driving
PH product quality.Using existing 2-PH analysis method, can not by control standard impurity 5- methyl-2-propyl hexenoic aldehyde with
Decomposition product diol separation in catalyst solution is opened, therefore causes the detection of 5- methyl-2-propyl hexenoic aldehyde in 2-PH product
As a result higher.Meanwhile BASF AG does not measure the decomposition product during the driving of 2-PH device in catalyst solution at present
Method.Therefore, a kind of analysis method for capableing of Accurate Determining 2-PH and its impurity content during driving is created, Bath can be made up
Husband company is particularly important the defect of 2-PH measuring method to the guarantee of 2-PH product quality during driving, and has weight
The economic value wanted.
Summary of the invention
Goal of the invention: present invention aims in view of the deficiencies of the prior art, provide one kind to properly separate 2-PH production
Glycol and impurity hexenoic aldehyde in product, thus the analysis method of 2- propyl enanthol and its impurity during Accurate Determining is driven.
Analysis method provided by the invention is suitable for (butylene mainly contained therein), carbon monoxide and the hydrogen of raffinating oil
Gas is raw material, the 2- propyl enanthol through carbonylation synthesis, condensation plus hydrogen, rectifying production.
Technical solution: the purpose of the invention is achieved by the following technical solution:
The present invention provides the analysis methods of a kind of 2- propyl enanthol and its impurity, measure 2- propyl heptan using GC-FID method
The content of alcohol and its impurity, gas chromatographic detection condition are as follows:
Chromatographic column: temperature program: capillary gas chromatographic column 80 DEG C of initial temperature, keeps 5min, with the speed of 6 DEG C/min
Rate is warming up to 250 DEG C, keeps 5min；
Detector: flame ionization ditector, 300 DEG C of the temperature of the detector；250 DEG C of injector temperature；
Carrier gas is nitrogen, helium or argon gas, flow rate of carrier gas 28mL/min；
Gas chromatograph is also configured with part flow arrangement.
Preferably, the gas chromatographic detection condition are as follows:
Chromatographic column: 30m × 0.25mm × 1 μm, DB-1 capillary chromatographic column,
Sampling volume: 0.2 μ L,
Flow velocity: 1.3mL/min,
Carrier gas is nitrogen,
Air velocity: 400mL/min,
Hydrogen flow rate: 30mL/min,
Split ratio: 80:1.
Preferably, the analysis method of the 2- propyl enanthol and its impurity, mainly comprises the steps that
(1) it sample preparation: is directly analyzed after being sampled in 2- propyl enanthol process units；
(2) it working reference substance solution: due to containing 5- methyl-2-propyl hexenoic aldehyde in 2- propyl heptenal product, takes and contains
There is the 2- propyl heptenal solution of 5- methyl-2-propyl hexenoic aldehyde as working reference substance solution；Without preparing impurity 5- methyl-
The standard solution of 2- propyl hexenoic aldehyde；
(3) it glycol standard solution: uses the 2- propyl enanthol of 5- methyl-2-propyl hexenoic aldehyde free from foreign meter as solvent, matches
The glycol standard solution that concentration is 0.3~1.5wt% is made；
(4) the working reference substance solution in step (2) is added in the glycol standard solution in step (3), is contained
The system suitability solution of 5- methyl-2-propyl hexenoic aldehyde and glycol；5- methyl-2-propyl hexenoic aldehyde in system suitability solution
Content in 0.02~0.05wt%, the content of glycol is in 0.3~1.5wt%.
(5) with the content of GC-FID method measurement 2- propyl enanthol and its impurity.
Preferably, the analysis method is further comprising the steps of: after instrument stabilizer, two needle error of continuous sample introduction less than 1%,
2- propyl enanthol is analyzed using area normalization method and its impurity content, calculation formula are as follows:
In the calculation formula, Ci is the content of each component in sample, wt%；Ai is the peak area of each component；
CH2OFor water content, wt%.
The utility model has the advantages that
(1) analysis method of the invention can Accurate Determining 2-PH and its impurity content, compensate for BASF AG to 2-
The defect of PH measuring method；During thoroughly solving the driving of 2-PH device, a kind of glycol and a kind of 5- methyl-2-propyl hexenoic aldehyde
The problem of measurement does not separate.Using original analysis method, the decomposition product in catalyst solution is mistaken for impurity 5-
Methyl-2-propyl hexenoic aldehyde causes the unqualified number of days of 2-PH product longer；Analysis method of the invention helps company 2-PH alcohols
Device shortens unqualified number of days 5~7 days of 2-PH product during stopping vehicle, generate considerable economic benefit, calculated roughly,
It drives at least save 1,700,000 yuan or more every time.In addition, analysis method of the invention can be applied in same device, product is generated
The economic benefit of pole.
(2) analysis method detection process of the invention is fast simple, and has good precision, reproducibility and stabilization
Property, effective way is provided for the quality control of 2-PH.
Detailed description of the invention
Fig. 1 is the GC chromatogram of the 2- propyl enanthol product of existing method detection；Wherein, 12.36min is in 2-PH product
The chromatographic peak of doubtful impurity composition a kind of " hexenoic aldehyde ".
Fig. 2 is the GC chromatogram that the glycol standard substance of existing method detection is added in 2-PH product；Wherein, 12.36min
For standard substance and a kind of chromatographic peak that " hexenoic aldehyde " is completely overlapped of doubtful impurity composition.
Fig. 3 is the GC chromatogram for the system suitability solution that analysis method of the invention detects；
Wherein, 15.423min is the chromatographic peak of 4- methyl-2-propyl hexenoic aldehyde, and 15.883min is 5- methyl-2-propyl
The chromatographic peak of hexenoic aldehyde, 15.723min are the chromatographic peak of glycol, and 17.738min is the chromatographic peak of 2- propyl enanthol.
Fig. 4 is the GC chromatogram of the 2-PH product of 1 analysis method of embodiment of the present invention detection；
Wherein, 15.734min is the chromatographic peak of glycol, and 17.753min is the chromatographic peak of 2- propyl enanthol.
Specific embodiment
Technical solution of the present invention is described in detail below by specific embodiments and the drawings, but protection of the invention
Range is not limited to the embodiment.
Instrument: Agilient-6890 type gas chromatograph (is furnished with fid detector, Agilent company of the U.S.)
Sample: 2-PH rule of origin is in Yangtze BASF AG；Working reference substance 2- propyl heptenal rule of origin is in raising
Sub- BASF AG；Decomposition product glycol develops limited public affairs from uncommon love (Shanghai) chemical conversion industry of TCI- ladder in catalyst solution
Department, content > 97%, lot number TU5YE-01.
In 2-PH inner quality standard, it is desirable that inner quality standard < 0.15% of impurity 5- methyl-2-propyl hexenoic aldehyde, product are qualified.
Embodiment 1:
GC conditions:
Chromatographic column: 30m × 0.25mm × 1 μm, DB-1 capillary chromatographic column
250 DEG C of injector temperature, 300 DEG C of detector temperature；
Carrier gas is nitrogen, flow rate of carrier gas 28mL/min；Air velocity: 400mL/min, hydrogen flow rate: 30mL/min；
Split ratio: 80:1.
Temperature program:, keeping 5min by 80 DEG C of initial temperature, is warming up to 250 DEG C with the rate of 6 DEG C/min, keeps 5min；Into
Sample volume: 0.2 μ L；Flow velocity: 1.3mL/min.
Analysis time: 38.5min.
Test method:
(1) it sample preparation: is directly analyzed after acquiring 2-PH sample in 2- propyl enanthol process units；
(2) it working reference substance solution: accurately weighs 0.1719g and contains the 4- methyl -2- third that known concentration is 3.676wt%
The 2- propyl heptenal solution for the 5- methyl-2-propyl hexenoic aldehyde that base hexenoic aldehyde and concentration are 2.789wt%, as Working Control
Product solution；
(3) glycol standard solution: with 2-PH (the 2- propyl of the 5- methyl-2-propyl hexenoic aldehyde free from foreign meter of 2-PH device
Enanthol) product as solvent, with the glycol standard items of purchase, is configured to the standard solution that concentration is 1.292wt% and (weighs
0.3982g standard items are diluted to 29.8972g).
(4) the working reference substance solution in step (2) is added in the standard solution in step (3) and (weighs total weight
For 30.0691g), the system suitability solution containing 5- methyl-2-propyl hexenoic aldehyde and glycol is obtained；
(5) content is measured with GC-FID method.
After instrument stabilizer, two needle error of continuous sample introduction analyzes 2- propyl enanthol and its miscellaneous less than 1%, using area normalization method
Matter content, calculation formula are as follows:
In the calculation formula, Ci is the content of each component in sample, wt%；Ai is the peak area of each component；
CH2OFor water content, wt%.
Using system suitability solution as sample, the content of wherein main component is measured using analysis method of the invention,
Testing result is shown in Table 1.
The GC chromatogram of system suitability solution is shown in Fig. 3, wherein 15.423min is the color of 4- methyl-2-propyl hexenoic aldehyde
Spectral peak, 15.883min are the chromatographic peak of 5- methyl-2-propyl hexenoic aldehyde, and 15.723min is the chromatographic peak of glycol, 17.738min
For the chromatographic peak of 2- propyl enanthol.
The GC measured value of main component in 1 system suitability solution of table
It measures content to calculate: measurement content=average value * extension rate
For the 4- methyl-2-propyl hexenoic aldehyde and 5- methyl-2-propyl hexenoic aldehyde in system suitability solution, dilution
Multiple=30.0691/0.1719=174.92；For the glycol and 2- propyl enanthol in system suitability solution, dilution times
Number=30.0691/29.8972=1.01.
By the conversion of extension rate, i.e. GC measured value is multiplied with extension rate, obtains working reference substance solution before diluting
With the content (obtaining the measurement content in table 2) of main component each in standard solution." actual content " refers to work pair in table 2
According to the compound concentration of product solution original content (GC measured value) and standard solution.
The Major Components result of 2 the method for the present invention of table is compared with the data of its actual content
| It measures content (%) | Actual content (%) | Relative error % | |
| 4- methyl-2-propyl hexenoic aldehyde | 3.673 | 3.676 | -0.09 |
| Glycol | 1.274 | 1.292 | -0.47 |
| 5- methyl-2-propyl hexenoic aldehyde | 2.974 | 2.789 | 6.63 |
| 2- propyl enanthol | 92.330 | 92.803 | -5.10 |
As shown in Table 2, the method for the present invention can not only efficiently separate each impurity, especially by 5- methyl-2-propyl hexene
Aldehyde is completely separable with glycol, can be with each impurity content of Accurate Determining；From the point of view of measurement result, it is able to satisfy technique requirement completely,
Measurement result and actual content also meet the measurement of the sample recovery rate in analysis method and require: 90-110%.
The 2-PH product directly sampled is detected using analysis method of the present invention, the content of each ingredient is directly obtained from GC
It arrives；And glycol and 5- methyl-2-propyl hexenoic aldehyde are separated.
The testing result of 2-PH product is shown in Table 3:
Fig. 4 is the GC chromatogram of 2-PH product；Wherein, 15.734min is the chromatographic peak of glycol, and 17.753min is 2- third
The chromatographic peak of base enanthol.
The content of main component in 3 2-PH product of table
By testing result it is found that analysis method of the invention can not only detect the production of the 2-PH containing above-mentioned several impurity
Product, additionally it is possible to which the new impurity glycol effectively in detection 2-PH product, each impurity chromatographic peak separator well is quantitative also accurate, is entirely capable of
Meet process data analysis to require.From the point of view of measurement result, measurement result and actual content also meet the sample in analysis method
Determination of recovery rates requirement: 90-110%.
Repeatability:
Same operator uses same instrument, under the same operating conditions, with normal and correct operating method
Repeatability measurement more than twice is carried out to same sample, measured value relative deviation is not more than 2%.
Stability:
Different operation personnel use different instruments, are measured to same sample, the relative deviation of two measurement results
No more than 5%.
Embodiment 2: using the recovery testu of analysis method measurement glycol of the invention
2-PH (2- propyl enanthol) product of 2-PH device is used to be configured to contain with the glycol standard items of purchase as solvent
The standard solution that amount is 0.3518%.
The measurement of glycol:
Measurement result is respectively 0.338%, 0.336%, 0.338% three times, the rate of recovery: 95.89%；RSD is (relatively average
Deviation): 0.3% (< 2%).
Analysis method detection process of the invention is fast simple, and has good precision, reproducibility and stability, is
The quality control of 2-PH provides effective way.
As described above, must not be explained although the present invention has been indicated and described referring to specific preferred embodiment
For the limitation to invention itself.It without prejudice to the spirit and scope of the invention as defined in the appended claims, can be right
Various changes can be made in the form and details for it.
Claims (4)
1. the analysis method of a kind of 2- propyl enanthol and its impurity, which is characterized in that measure 2- propyl enanthol using GC-FID method
And its content of impurity, gas chromatographic detection condition are as follows:
Chromatographic column: temperature program: capillary gas chromatographic column 80 DEG C of initial temperature, keeps 5min, with the rate liter of 6 DEG C/min
Temperature keeps 5min to 250 DEG C；
Detector: flame ionization ditector, 300 DEG C of the temperature of the detector；250 DEG C of injector temperature；
Carrier gas is nitrogen, helium or argon gas, flow rate of carrier gas 28mL/min；
Gas chromatograph is also configured with part flow arrangement.
2. the analysis method of 2- propyl enanthol according to claim 1 and its impurity, which is characterized in that the gas-chromatography
Testing conditions are as follows:
Chromatographic column: 30m × 0.25mm × 1 μm, DB-1 capillary chromatographic column,
Sampling volume: 0.2 μ L,
Flow velocity: 1.3mL/min,
Carrier gas is nitrogen,
Air velocity: 400mL/min,
Hydrogen flow rate: 30mL/min,
Split ratio: 80:1.
3. the analysis method of 2- propyl enanthol according to claim 1 or 2 and its impurity, which is characterized in that mainly include
Following steps:
(1) it sample preparation: is directly analyzed after being sampled in 2- propyl enanthol process units；
(2) working reference substance solution: take the 2- propyl heptenal for containing 5- methyl-2-propyl hexenoic aldehyde molten as working reference substance
Liquid；Without preparing the standard solution of impurity 5- methyl-2-propyl hexenoic aldehyde；
(3) decomposition product glycol standard solution: use the 2- propyl enanthol of 5- methyl-2-propyl hexenoic aldehyde free from foreign meter as molten
Agent, being configured to concentration is 0.3~1.5wt% glycol standard solution；
(4) the working reference substance solution in step (2) is added in the glycol standard solution in step (3), is obtained containing 5-
The system suitability solution of methyl-2-propyl hexenoic aldehyde and glycol；
(5) with the content of GC-FID method measurement 2- propyl enanthol and its impurity.
4. the analysis method of 2- propyl enanthol according to claim 3 and its impurity, which is characterized in that further include following step
Rapid: after instrument stabilizer, two needle error of continuous sample introduction analyzes 2- propyl enanthol using area normalization method and its impurity contains less than 1%
Amount, calculation formula are as follows:
In the calculation formula, Ci is the content of each component in sample, wt%；Ai is the peak area of each component；CH2OContain for water
Amount, wt%.
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