CN104792726B - A kind of rapid analysis method of ethanol amine aminating reaction process-stream - Google Patents
A kind of rapid analysis method of ethanol amine aminating reaction process-stream Download PDFInfo
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Abstract
The invention discloses a kind of rapid analysis methods of ethanol amine aminating reaction process-stream, the process-stream is the reactant incoming stream or product output stream of aminating reaction device, one material is extracted from process-stream as tributary, cooling tributary material is analyzed using near infrared spectroscopy, acquires the near infrared light spectrum information of reactant incoming stream or product output stream；The corresponding standard value of the near infrared spectrum of reaction process logistics (chemical score) is associated using Partial Least Squares and establishes quantitative calibration models, directly determines the mass fraction of various ingredients in reaction process stream by the near infrared spectrum obtained using institute's established model；According to the mass fraction of each component and the demand of aminating reaction in surveyed process output logistics and input logistics, the mass fraction of inlet flow component in inlet flow is adjusted.Present invention is mainly used for the quick analyses of ethanol amine aminating reaction process-stream.
Description
Technical field
The invention belongs to the analysis and testing technology fields of chemical process, are related to a kind of quickly dividing for aminating reaction process-stream
Analysis method.
Background technology
Ethylenediamine is a kind of widely used basic organic chemical raw material, is mainly used for epoxy curing agent, pesticide, doctor
Medicine, chelating agent etc..In general, using ethanol amine and ammonia for raw material, aminating reaction is carried out in the presence of amination catalysis and obtains amination
Product, being removed through the isolated various aminated products of rectification process, wherein in aminate has unreacted raw material ammonia, ethanol amine
Outside, there are water, ethylenediamine, diethylenetriamine, hydroxyethyl ethylenediamine etc. in product.
In order to explore the various operating conditions of aminating reaction and separating technology, aminating reaction product needs are quantitatively divided
Analysis, common analysis method have gas chromatography, liquid chromatography, potentiometric titration, photometry and pH potentiometrys.Sun Guosong exists
《The gas chromatography analysis method of ethanol amine reduction amination reacting ethylenediamine liquid》Physical and chemical inspection-chemistry fascicle, 2011, (47) ︰
The gas chromatography analysis method of reacting ethylenediamine liquid is reported in 711.This method uses chiral chromatographic column, using temperature programming and
Ethylene glycol internal standard compound is as chromatographic condition, by related component separation and quantitative in ethylenediamine building-up process.This analysis method operation
Cumbersome, labor intensity is big, and analysis time is long, greatly affected automatically controlling and adjusting for commercial plant, also constrains anti-
Answer the automation of device.Meanwhile gas chromatographic technique can not be in Rapid Simultaneous Determination aminating reaction liquid water production quantity, it is difficult to
The technique stream in vapor phase is analyzed, some components such as water vapour may condense, and so that acquisition is reliably analyzed data becomes tired
It is difficult.
Invention content
The object of the present invention is to provide a kind of rapid analysis methods of aminating reaction process-stream, have operating procedure letter
Advantage single, analysis time is short, and can in Rapid Simultaneous Determination aminating reaction liquid water production quantity.
According to the present invention, a kind of rapid analysis method of ethanol amine aminating reaction process-stream is provided, which is
The reactant incoming stream or product output stream of aminating reaction device, the technique stream have at least 180 DEG C of temperature, the component of process-stream
In vapor phase, this method includes：
(1) one material is extracted from process-stream as tributary；
(2) temperature of tributary material is higher than its dew-point temperature；
(3) cooling tributary material is analyzed using near infrared spectroscopy, acquires reactant incoming stream or product output stream
Near infrared spectrum；
(4) the reaction process logistics with standard value is divided into calibration set and verification collects, calibration set is tested for establishing model
Accuracy of the card collection for verifying model, using Partial Least Squares, by correction light harvesting spectrum by the pretreated number of selectivity
According to corresponding standard value linear correlation, establish calibration model, using above-mentioned calibration model to verification collection predict, will predict
Value and standard value contrast verification model；
(5) institute's established model is used, is directly obtained instead according to the near infrared spectrum of acquisition reactant incoming stream or product output stream
Answer the mass fraction of one or more components in technique stream.
The reactant incoming stream includes ethanol amine, ammonia, may contain water existing for vapor form, and product output stream includes
Ammonia, ethanol amine, ethylenediamine, diethylenetriamine, hydroxyethyl ethylenediamine and generation water.
Ammonia, ethanol amine, ethylenediamine, diethylenetriamine, hydroxyethyl ethylenediamine and generation in the reaction product output stream
The standard value of water is used in conjunction analysis method using gas chromatography-mass spectrum and measures its mass fraction, and moisture uses Karl_Fischer method
Quality measurement fractional data.
The process-stream can be 9800 to 5300cm by quantitative SPECTRAL REGION-1。
According to the present invention, the rapid analysis method of another ethanol amine aminating reaction process-stream, the process-stream are provided
It is the reactant incoming stream or product output stream of aminating reaction device, which is higher than 180 DEG C, and the component of process-stream is in
In vapor phase, this method includes：
(1) one material is extracted from process-stream as tributary；
(2) temperature of tributary material is higher than its dew-point temperature；
(3) cooling tributary material is analyzed using near infrared spectroscopy, acquires reactant incoming stream or product output stream
Near infrared spectrum；
(4) the reaction process logistics with standard value is divided into calibration set and verification collects, calibration set is tested for establishing model
Accuracy of the card collection for verifying model, using Partial Least Squares, by correction light harvesting spectrum by the pretreated number of selectivity
According to corresponding standard value linear correlation, establish calibration model, using above-mentioned calibration model to verification collection predict, will predict
Value and standard value contrast verification model；
(5) institute's established model is used, is directly obtained instead according to the near infrared spectrum of acquisition reactant incoming stream or product output stream
Answer the mass fraction of one or more components in technique stream；
(6) ethanol amine or ammonia group in inlet flow are adjusted in response to identified mass fraction according to the demand of aminating reaction
The mass fraction divided.
Advantages of the present invention：
(1) present invention analyzes cooling tributary material using near infrared spectroscopy, acquires reactant incoming stream or product is defeated
The near infrared light spectrum information for going out stream eliminates sample pre-treatments step, operating procedure letter compared with gas chromatography, titration
It is single.
(2) present invention uses institute's established model, according to acquisition reactant incoming stream or the near infrared spectrum of product output stream, 1
The mass fraction of one or more components in reaction process stream can be directly obtained in minute, analysis time is short, has succinct, fast
The advantage of speed.
(3) present invention adjusts ethanol amine in inlet flow according to the demand of aminating reaction in response to identified mass fraction
Or the mass fraction of ammonia components, it can realize the on-line analysis of ethanol amine aminating reaction, be advantageously implemented automation, convenient for industry
Production process controls.
(4) present invention can in Rapid Simultaneous Determination aminating reaction liquid water production quantity.
Description of the drawings
The quick analysis schematic diagram of Fig. 1 ethanol amine aminating reaction process-streams
Specific implementation mode
The present invention is described in further detail for the embodiment provided below in conjunction with inventor.
Fig. 1 is the quick analysis schematic diagram of ethanol amine aminating reaction process-stream.Including heater (1), heater (4),
Evaporation mixer (2), reactor (6), cooler (3), NIR flow cells (7), NIR light spectrometer (5), optical fiber cable (110) and
(109), gas-liquid separator (8), cooler (9), adjuster (10), triple valve (11).
101,102,103,104,105,106,107,108,111,112,113,114,115 be pipeline.
In the present invention, NIR analyzers are available commercially near infrared spectrometers, and main element includes light source, optics
System and detector.NIR light spectrometer (5), for the Fourier transformation type spectrometer of Brooker company manufacture.
NIR light spectrometer (5) is connect by optical cable and optical fibres with NIR flow cells (3).The NIR flow cells used are low hydroxyl stone
English material, optical path length 7.5cm, flow cell and vapor line are electrically heated to the dew point higher than steam mixture.
Technique input logistics ethanol amine, liquefied ammonia component are separately input into heater (1) by pipeline 101,102 respectively and add
Hot device (4), then enter evaporation mixer (2) through pipeline 103,114, the gaseous component stream of input evaporation mixer (2) can be used
Mass flow controller is adjusted, and enters reactor (6) by pipeline 104 after mixing, is catalyzed in amination in reactor (6)
Carry out aminating reaction in the presence of agent, product output stream include ammonia, ethanol amine, ethylenediamine, diethylenetriamine, hydroxyethyl ethylenediamine and
Generate water.
The steam mixture generated in evaporation mixer (2) leads to NIR flow cells (7), NIR streams by branch line 107
Effluent stream in logical pond (7) is through cooler (9) and the pressure tune by detaching the separator (8) and control system pressure of liquid
Device (10) is saved to be discharged.NIR flow cells (7) are connected to NIR light spectrometer (5), NIR flow cells by optical fiber cable (110) and (109)
(7) steam mixture in is analyzed by NIR light spectrometer (5), spectrometer scanning wavelength ranging from 12500 to 4000cm-1, resolution ratio
8cm-1, using optical cable and optical fibres loop as reference.
Ethanol amine, liquefied ammonia are configured to the normal mixture of different quality containing using mass flowmenter, as reaction work
Skill inputs logistics, is divided into calibration set and verification and collects, and calibration set collects the accuracy for verifying model for establishing model, verification,
Using Partial Least Squares, correction light harvesting spectrum is passed through into the pretreated data of selectivity and corresponding standard value linear correlation,
The calibration model of technique input logistics is established, the preprocess method of use has：Without Pretreated spectra, multiplicative scatter correction (MSC),
Vector normalization method (SNV), min-max normalization, first derivative, first derivative+SNV, first derivative+MSC, second dervative
Deng.
Using the Optimized models such as different pretreatments method, different dimensions, different spectral bands, selectable rejecting abnormalities
Value is predicted verification collection using above-mentioned calibration model, by predicted value and above-mentioned standard value contrast verification model.
Input stream components model is built using above-mentioned, is directly obtained instead according to the near infrared spectrum of acquisition reactant incoming stream
Answer ethanol amine in technique inlet flow, liquefied ammonia component mass fraction.
Logistics and product output stream are inputted respectively by branch line 107 and branch line 108, three for reaction process
It is periodically mutually tangent at port valve (11), it changes towards NIR flow cells (7) and carries out periodical measurement, switching cycle 2 minutes.
Similarly, the product output stream that reactor (6) generates is passing through pipeline 106, into separation through subcooler (3)
The separator (8) of liquid and pressure regulator (10) discharge of control system pressure, reaction output product stream pass through branch line
108 lead to NIR flow cells (7), and NIR flow cells (7) are connected to NIR light spectrometer (5), NIR flow cells by optical fiber cable (110)
(7) steam mixture in is analyzed by NIR light spectrometer (5), spectrometer scanning wavelength ranging from 12500 to 4000cm-1, resolution ratio
8cm-1, using optical cable and optical fibres loop as reference.
It is that calibration set and verification collect by reaction process output flow point, calibration set is for establishing model, and verification collection is for testing
The accuracy of model of a syndrome, using Partial Least Squares, will correction light harvesting spectrum by the pretreated data of selectivity with it is corresponding
Standard value linear correlation establishes the calibration model of process output logistics；Verification collection is predicted using above-mentioned calibration model, it will
Predicted value and above-mentioned standard value contrast verification model.
Reaction process output logistics includes ammonia, ethanol amine, ethylenediamine, diethylenetriamine, hydroxyethyl ethylenediamine and generates water,
Wherein moisture standards value is measured using Karl_Fischer method, and analysis method is used in conjunction using gas chromatography-mass spectrum in remaining Component Standard value
It measures.
Output logistics compositional model is built using above-mentioned, the near infrared spectrum that output stream is reacted according to acquisition directly obtains instead
It answers and flows ammonia, ethanol amine, ethylenediamine, diethylenetriamine, hydroxyethyl ethylenediamine and the mass fraction for generating water in process output stream.
Compare reaction process inlet flow in ethanol amine, liquefied ammonia component mass fraction, with reaction process output stream in stream ammonia,
Ethanol amine, ethylenediamine, diethylenetriamine, hydroxyethyl ethylenediamine and the mass fraction for generating water, calculate the ethanol amine of aminating reaction
It is defeated to adjust reaction process in response to identified mass fraction according to the demand of aminating reaction for the selectivity of conversion ratio and product
Become a mandarin the mass fractions of middle ethanol amine or ammonia components.
Embodiment 1：
As shown in Figure 1, using NIR analyzers, it is quick to technique input logistics ethanol amine, the NIR spectra of liquefied ammonia mixture
Analysis.Technique input logistics ethanol amine, liquefied ammonia component are separately input into heater (1) and heating by pipeline 101,102 respectively
Device (4), then enter evaporation mixer (2) through pipeline 103,114, matter can be used in the gaseous component stream of input evaporation mixer (2)
Amount flow controller is adjusted, and enters reactor (6) by pipeline 104 after mixing, in amination catalysis in reactor (6)
In the presence of carry out aminating reaction.
The steam mixture generated in evaporation mixer (2) leads to NIR flow cells (7), NIR streams by branch line 107
Effluent stream in logical pond (7) is through cooler (9) and the pressure tune by detaching the separator (8) and control system pressure of liquid
Device (10) is saved to be discharged.NIR flow cells (7) are connected to NIR light spectrometer (5), NIR flow cells by optical fiber cable (110) and (109)
(7) steam mixture in is analyzed by NIR light spectrometer (5), spectrometer scanning wavelength ranging from 12500 to 4000cm-1, light path
7.5cm, resolution ratio 8cm-1, scan 32 times, using optical cable and optical fibres loop as reference.
Ethanol amine, liquefied ammonia are configured to the normal mixture 89 of different quality containing using mass flowmenter, are divided into school
Positive collection and verification collection, ethanol amine (2~30%) mixs with (70~98%) in evaporation mixer (2), and 220 DEG C with
Flow cell is inputted under 1.8MPa gross pressures, acquires Standard Gases spectrum.Scanning optical spectrum section 12500 is to 4000cm-1, light path 7.5cm,
Resolution ratio 8cm-1, scanning times 32 times.Using Partial Least Squares, by correction light harvesting spectrum by the pretreated data of selectivity
With corresponding standard value linear correlation, the calibration model of technique input stream components is established.
Calibration model is verified with verification collection sample, is evaluated, ethanol amine and the best calibration model of ammonia components are optimized to obtain：
The calibration model of ethanol amine constituent mass score, quantitative spectrometric ranging from 8914~8799cm-1With 5975~5446cm-1, spectrum
Preprocess method selection single order leads+MSC, the coefficient of determination (R of model2) it is 0.987, model cross validation root-mean-square-deviation
(RMSECV) value is 0.11%, and the value of verification collection root-mean-square-deviation (RMSEP) is 0.09%；The correction of ammonia components mass fraction
Model, quantitative spectrometric ranging from 7362~6353cm-1, preprocessing procedures selection single order lead+SNV, the R of model2For
0.981, model RMSECV are 0.15%, and verification collection RMSEP is 0.11%；
Using above-mentioned institute's established model, reaction work is directly obtained according to the near infrared spectrum of the reactant incoming stream of spectrometer collection
The mass fraction of ethanol amine and ammonia components in skill inlet flow.
Embodiment 2：
As shown in Figure 1, using NIR analyzers, the NIR spectra of process output stream components is quickly analyzed.Technique inputs
Logistics ethanol amine, liquefied ammonia component are separately input into heater (1) and heater (4) by pipeline 101,102 respectively, then through pipeline
103,114 enter evaporation mixer (2), input evaporation mixer (2) gaseous component stream can be used mass flow controller into
Row is adjusted, and enters reactor (6) by pipeline 104 after mixing, amination is carried out in the presence of in reactor (6) in amination catalysis
Reaction.
The product output stream that reactor (6) generates, through subcooler (3), using pipeline 106, into separation liquid
Separator (8) and the discharge of the pressure regulator (10) of control system pressure, reaction output product stream are existed by branch line 108
220 DEG C are connected with input NIR flow cells (7) under 1.8MPa gross pressures, NIR flow cells (7) by optical fiber cable (110) and (109)
It is connected to NIR light spectrometer (5), the steam mixture in NIR flow cells (7) is analyzed using NIR light spectrometer (5).Spectrometer scans wave
Long ranging from 12500 to 4000cm-1, light path 7.5cm, resolution ratio 8cm-1, scan 32 times, using optical cable and optical fibres loop as ginseng
Than.
The spectrum 205 for acquiring reaction process the output of process logistics, is divided into calibration set and verification collects.In the same of acquisition spectrum
When sampling carry out standard value analysis, product export logistics include ammonia, ethanol amine, ethylenediamine, diethylenetriamine, hydroxyethyl ethylenediamine
And six kinds of components of water are generated, the mass fraction for generating water uses Karl_Fischer method quality measurement score, the mark of remaining constituent content
Quasi- value is used in conjunction analysis method using gas chromatography-mass spectrum and measures its mass fraction.
Using Partial Least Squares, by correction light harvesting spectrum by the pretreated data of selectivity and corresponding standard value line
Property association, establish the calibration model of six kinds of components of process output logistics.It tested, commented to calibration model with verification collection sample
The parameter of valence, optimization gained best model is shown in Table 1.
Using above-mentioned institute's established model, the near infrared spectrum of acquisition reaction output stream directly obtains in reaction process output stream
Ammonia, ethanol amine, ethylenediamine, diethylenetriamine, hydroxyethyl ethylenediamine and the mass fraction for generating water, and acquire 18 samples and adopt
It is analyzed with chemical method, the standard value of near infrared spectroscopy predicted value and chemical determination is shown in Table 2.
Logistics and product output stream are inputted respectively by branch line 107 and branch line 108, three for reaction process
It is periodically mutually tangent at port valve (11), it changes towards NIR flow cells (7) and carries out periodical measurement, switching cycle 2 minutes.
In conjunction with the embodiments in 1 in reaction process inlet flow ethanol amine, ammonia components mass fraction, with ammonia, ethanol amine, second two
Amine, diethylenetriamine, hydroxyethyl ethylenediamine and the mass fraction for generating water.According to aminating reaction ammonia and ethanol amine molar ratio
Demand calculates the input quantity of ethanol amine or ammonia components in inlet flow, and is adjusted.
Table 1 exports the parameter of logistics each component model
| Model name | Quantitative spectrometric range/cm-1 | Preprocessing procedures | R2 | RMSECV/% | RMSEP/% |
| Ammonia | 9780~9395,7362~6353 | Single order leads+SNV | 0.98 | 0.43 | 0.46 |
| Ethanol amine | 8914~7903,5975~5446 | Single order leads+MSC | 0.99 | 0.57 | 0.55 |
| Ethylenediamine | 9763~9365,8825~7961 | Single order leads+MSC | 0.97 | 0.23 | 0.22 |
| Diethylenetriamine | 9634~7946 | Single order is led | 0.98 | 0.12 | 0.12 |
| Hydroxyethyl ethylenediamine | 7306~6367 | Single order leads+SNV | 0.97 | 0.11 | 0.09 |
| Water | 7494~5326 | SNV | 0.99 | 0.09 | 0.08 |
Table 2 is using near infrared spectroscopy predicted value and the standard value for using chemical determination
Claims (2)
1. a kind of rapid analysis method of ethanol amine aminating reaction process-stream, which is ethanol amine aminating reaction device
Reactant incoming stream or product output stream, this method include：
(1) one material is extracted from process-stream as tributary；
(2) temperature of tributary material is higher than its dew-point temperature；
(3) cooling tributary material is analyzed using near infrared spectroscopy, acquires the close red of reactant incoming stream or product output stream
External spectrum；
(4) the reaction process logistics with standard value is divided into calibration set and verification collects, calibration set is for establishing model, verification collection
Accuracy for verifying model, using Partial Least Squares, will correction light harvesting spectrum by the pretreated data of selectivity with
Corresponding standard value linear correlation, establishes calibration model, using above-mentioned calibration model to verification collection predict, by predicted value with
Standard value contrast verification model；
(5) institute's established model is used, reaction work is directly obtained according to the near infrared spectrum of acquisition reactant incoming stream or product output stream
The mass fraction of one or more components in skill stream；
There is the process-stream at least 180 DEG C of temperature, the component of process-stream to be in vapor phase；
In the process-stream, reactant incoming stream includes ethanol amine, ammonia, and product output stream includes ammonia, ethanol amine, ethylenediamine, two
Ethylene triamine, hydroxyethyl ethylenediamine and generation water；
Ammonia, ethanol amine, ethylenediamine, diethylenetriamine, hydroxyethyl ethylenediamine in reaction product output stream and generate water
Standard value is used in conjunction analysis method using gas chromatography-mass spectrum and measures its mass fraction, and moisture is measured using Karl_Fischer method
Mass fraction；
The process-stream can be 9800 to 5300cm by quantitative SPECTRAL REGION-1。
2. the rapid analysis method of ethanol amine aminating reaction process-stream according to claim 1, the process-stream are second
The reactant incoming stream or product output stream of hydramine aminating reaction device, this method include：
(1) one material is extracted from process-stream as tributary；
(2) temperature of tributary material is higher than its dew-point temperature；
(3) cooling tributary material is analyzed using near infrared spectroscopy, acquires the close red of reactant incoming stream or product output stream
External spectrum；
(4) the reaction process logistics with standard value is divided into calibration set and verification collects, calibration set is for establishing model, verification collection
Accuracy for verifying model, using Partial Least Squares, will correction light harvesting spectrum by the pretreated data of selectivity with
Corresponding standard value linear correlation, establishes calibration model, using above-mentioned calibration model to verification collection predict, by predicted value with
Standard value contrast verification model；
(5) institute's established model is used, the near infrared spectrum that input logistics or product output logistics are reacted according to acquisition directly obtains instead
Answer the mass fraction of various ingredients in technique stream；
(6) according to the mass fraction of various ingredients in reaction process stream, the demand with ethanol amine aminating reaction calculates in inlet flow
The input quantity of ethanol amine or ammonia components, and be adjusted.
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