CN105628833A - Long-chain alkene double bond rapid on-line determination apparatus and application - Google Patents
Long-chain alkene double bond rapid on-line determination apparatus and application Download PDFInfo
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Abstract
The present invention provides a long-chain alkene double bond rapid on-line determination system and method, the long-chain alkene double bond rapid on-line determination system includes an ozone generator, a sample gas generating device, an ozone decomposition reaction apparatus, a gas supply means and a reaction outflow gas detection means. According to the long-chain alkene double bond rapid on-line determination method, the long-chain alkene double bond rapid on-line determination system is used for dividing high purity oxygen into two paths, one path enters the ozone generator in a certain flow rate to obtain a certain concentration of ozone, and meanwhile the other path passes through the sample gas generating device in a certain flow rate to obtain a certain concentration of an olefin sample gas. Finally, two paths of the gas are merged to enter the ozone decomposition reaction apparatus, part of a reaction outflow gas enters the reaction outflow gas detection means for analysis, and remaining reaction outflow gas is discharged as exhaust. Different concentrations of ozone can be obtained by changing the flow rate of the high purity oxygen and the current of the ozone generator, ozone decomposition reaction products enter directly the reaction outflow gas detection means without off-line concentration, derivation and other steps, and the method is simple in operation, fast in analysis speed and high in measurement precision.
Description
Technical field
The present invention relates to a kind of device and application quickly determining long-chain olefin position of double bond online, this on-line analysis device is utilized to be mixed with the sample gas of long-chain olefin by certain density ozone exactly specifically, so as to there is ozonolysis reactions, final reaction flows out gas and rapidly enters gas-detecting device by capillary tube, thus realizing fast on-line analyzing long-chain olefin double bond by the purpose of ozone decomposed products therefrom.
Background technology
Long-chain olefin (long-chainolefins) is a kind of important Organic Ingredients and intermediate product, is widely used in surfactant, plasticizer, poly alpha olefin, lubricating oil, auxiliary agent and fine chemicals. The production of China's linear alkene is mainly based on wax destructive distillation, ethylene oligomerization and linear paraffin catalytic dehydrogenation device. The product of linear alkanes dehydrogenation is sufficiently complex, has alpha-olefin and linear internal in product, and linear internal position of double bond is different, has a lot of isomer. How fast on-line measurement concentration of olefin, and determine the position of double bond of alkene, for optimizing catalyst composition and reaction condition, improve conversion ratio, reduce by-product, particularly significant. The method measuring long chain hydrocarbon general is derivatization, then with high-resolution capillary chromatography GC, or two dimension GC �� GC chromatograph, GC-MS multiple techniques measures. But these methods cannot determine long-chain olefin position of double bond, and consuming time very long, it is difficult to for process monitoring. Development alkene, polyene method for fast measuring, the method particularly determining olefinic double bonds position, not only facilitate the understanding catalytic dehydrogenation mechanism of linear paraffin and process, also improve the selectivity of reaction and productivity lays the foundation for designing better catalyst.
The position of double bond of alkene is accurately measured and is always up analytical chemistry field and has much a difficult problem for challenge, this is because peak overlap near double bond, the H NMR spectroscopy method that structural analysis is conventional, it is impossible to provide enough information to determine the position of double bond, and method of infrared spectrophotometry can only measure alhpa olefin. The method of off-line measurement olefinic double bonds mainly measures the product of alkene derivatization. The derivatives reaction of bibliographical information has: ozonolysis reactions, dimethyl disulfide addition, olefin metathesis reaction. But the step of these derivative reactions is many, length consuming time, and also the sample size needed is big, complicated operation, and automaticity is very low, is not suitable for quickly analyzing and large-scale application.
Direct mass spectrum determines that the spectroscopy technique that olefinic double bonds position is given priority to. Can be higher in the ion that electron bombardment (EI) ionization produces, it may occur that quickly isomerization reaction, cause determining that the reliability of position of double bond is poor with EI mass spectrum. At the end of the eighties, the chemi-ionization technology (CACI) having developed metal ion addition and covalency addition determines position of double bond. As acetonitrile can produce m/e=54 [H2C=N+=C=CH2] ion, it can with the double bond generation additive reaction of alkene, and its ion addition thing is collisionally dissociated the fragment ion that can produce feature. Molecular weight according to fragment ion, it may be determined that the position of double bond. Due to H2C=N+=C=CH2It is reactant CH3The secondary ion molecular product of CN, does not only have m/e=54, also has m/e=42 and 81 ion that abundance is higher, therefore hardly result in the reactive ion that comparison is pure in reagent ion. Additionally the productivity of this covalency additive reaction is low, and the dissociation channel of addition intermediate radical is also more, and product is complex, and therefore the CACI of acetonitrile only succeeds at present in the double bond of unsaturated fatty acid ester is measured.
The biased sample of long-chain olefin, alkadienes and substituted benzene directly can be carried out on-line analysis by Single-photon ionization-flight time mass spectrum (SPI-TOFMS) technology. But SPI-TOFMS method but cannot be distinguished by the isomers being differently formed by position of double bond, the position of double bond in each isomer also cannot be determined.
Purpose herein is in that to provide a kind of new method determining long-chain olefin position of double bond. The method is with stainless steel tube for ozonolysis reactions place, and the sample gas of certain density ozone and long-chain olefin is in this hybrid reaction, and then ozonolysis product enters reaction stream and gives vent to anger and carry out ionization detection in detecting device and single photon ionization mass spectrum instrument. The method achieve fast on-line analyzing, it is not necessary to any pre-concentration, derivatization or elution step. It addition, this device gas circuit is simple, with low cost, it is simple to operation.
Summary of the invention
It is an object of the invention to provide a kind of device and application quickly determining long-chain olefin position of double bond online.
For achieving the above object, technical scheme is as follows:
A kind of device quickly determining long-chain olefin position of double bond online, it is characterised in that: include ozone generating-device, sample gas generator, ozonolysis reactions device, feeder and reaction stream and give vent to anger detecting device;
Wherein, described feeder includes oxygen source, and the gas outlet of oxygen source is connected with the carrier gas inlet of the gas access of ozone generating-device and sample gas generator respectively through two pipelines, is respectively equipped with mass flow controller on two pipelines;
The ozone outlet of ozone generating-device is all connected with the gas access of ozonolysis reactions device with the gas outlet of sample gas generator;
Give vent to anger with the reaction stream gas sampling mouth of detecting device of the gas outlet of ozonolysis reactions device is connected.
Described ozonolysis reactions device is copper pipe or stainless steel tube, and its one end is connected with the ozone outlet of ozone generating-device and the gas outlet of sample gas generator, and give vent to anger with the reaction stream gas sampling mouth of detecting device of the other end is connected;
Described sample gas generator is one with the hollow airtight cavity of heating element heater, what hollow airtight cavity was provided with fluid sample bottle is removed and placed into mouth, fluid sample bottle be removed and placed into mouth by a lid that can open and close airtight, fluid sample bottle is contained in hollow airtight cavity.
Described ozonolysis reactions device length is adjustable, and profile is non-directional screw type or U-shape structure, it is simple to ozone and long-chain olefin sample gas are sufficiently mixed reaction;
Heating element heater is electrical heating wire, heat tape or electrical heating block;
Sample gas generator is that the stainless steel cylinder with rustless steel bottle cap, rustless steel bottle cap and rustless steel body are fastened by screw thread, and utilizes O-ring to seal, and inside holds fluid sample bottle.
Oxygen source is the dry air after the steel cylinder equipped with oxygen or purification;
The ozone gas of producing of ozone generating-device is high pure oxygen or dry air, and the uninterrupted of size of current and ozone gas processed that the concentration preparing ozone can pass through adjustment ozone generating-device regulates.
Described reaction stream is given vent to anger the analytical equipment that detecting device is direct gas sampling, is mainly the on-line mass spectroscopy instrument of gas sampling, is connected with ozonolysis reactions device by gas conduit; Ozonolysis reactions flows out a part of sampling analysis of gas, and all the other are discharged as tail gas;
The cavity size of described sample gas generator can with the size adjustment of long-chain olefin sample bottle, and cavity heating-up temperature can set according to the long-chain olefin boiling point height of research.
Quickly determine that in fluid sample, long-chain olefin position of double bond analyzes the application of process online, it is characterised in that:
A. will be equipped with putting into sample gas generator containing the sample bottle of long-chain olefin liquid, sample gas generator seals;
B. the substantially boiling point according to long-chain olefin contained in fluid sample, sets the heating-up temperature of sample gas generator: utilize temperature controller to control heating element heater, makes the temperature stabilization after the heating of setting sample gas generator;
C. open the gas outlet of feeder, pass in two pipelines, set the gas flow size of two pipelines, successively make gas respectively enter ozone generating-device and sample gas generator;
D. open ozone generating-device power supply, set current values, prepare ozone;
E. the ozone flowed out from ozone generating-device enters ozonolysis reactions device hybrid reaction together with the junction of long-chain olefin sample gas;
F. utilize reaction stream the to give vent to anger quick on-line sampling of partial reaction gas that ozonolysis reactions device flows out by detecting device, it is thus achieved that long-chain olefin double bond is by the feature spectrogram of ozone decomposed afterproduct.
Described gas conduit is quartz capillary or stainless steel capillary;
Described ozonolysis reactions device is the pipeline of stainless steel, and non-cohesive material, it is to avoid the ozone corrosion to reaction pipeline.
Reaction stream detecting device of giving vent to anger is online gas sampling mass spectrograph, adopts Single-photon ionization (SPI) that reaction stream is given vent to anger and ionizes, and the method can simplify the spectrogram of ozonolysis product, it is simple to spectrum elucidation.
Long-chain olefin is the C containing a double bond8-C16Chain olefin.
The ultimate principle of this on-line analysis is:
First, the double bond of long-chain olefin by the principle of ozone decomposed is:
Secondly, reaction stream detecting device of giving vent to anger adopts the ionization mode of Single-photon ionization, it is thus achieved that the ionization principle of ozonolysis product is:
Wherein for long-chain olefin, product is mainly aldehydes. But due to ionization energy and the molecular structure of aldehydes, SPI ionizes product and is likely to except molecular ion peak also has other fragment ion peaks. But comparing electron impact ionization, spectral peak is simply a lot.
The electric current of flow velocity and ozone generating-device that the present invention changes high pure oxygen can obtain the ozone of variable concentrations, ozonolysis reactions product be directly entered reaction stream give vent to anger detecting device concentrate without off-line, the step such as derivative, simple to operate, analyze speed fast, measurement accuracy is high.
Accompanying drawing explanation
Fig. 1 is the device schematic diagram quickly determining long-chain olefin position of double bond online: 1-ozone generating-device; 2-sample gas generator; 3-ozonolysis reactions device; 4-feeder; 5-reaction stream is given vent to anger detecting device; 6-height pure oxygen steel cylinder; 7-precision mass flow controller; 8-vacuum UV lamp; 9-gas conduit; 10-ionized region; 11-vacuum equipment; 12-field-free flight district; 13-MCP detector; 14-data collecting system; 15-tail gas.
Fig. 2 is the SPI spectrogram of three kinds of long-chain decene isomerss and ozonolysis product thereof;
Fig. 3 is the SPI spectrogram of three kinds of long-chain octene isomerss and ozonolysis product thereof
Fig. 4 is the SPI spectrogram of seven kinds of aldehyde product.
Detailed description of the invention
First, Fig. 1 is a kind of device quickly determining long-chain olefin position of double bond online, it is characterised in that: include ozone generating-device 1, sample gas generator 2, ozonolysis reactions device 3, feeder 4 and reaction stream and give vent to anger detecting device 5;
Wherein, described feeder 4 includes oxygen source 6, and the gas outlet of oxygen source 6 is connected with the carrier gas inlet of the gas access of ozone generating-device 1 and sample gas generator 2 respectively through two pipelines, is respectively equipped with mass flow controller 7 on two pipelines;
The ozone outlet of ozone generating-device 1 is all connected with the gas access of ozonolysis reactions device 3 with the gas outlet of sample gas generator 2;
Give vent to anger with the reaction stream gas sampling mouth of detecting device 5 of the gas outlet of ozonolysis reactions device 3 is connected.
Described ozonolysis reactions device 3 is copper pipe or stainless steel tube, and its one end is connected with the ozone outlet of ozone generating-device 1 and the gas outlet of sample gas generator 2, and give vent to anger with the reaction stream gas sampling mouth of detecting device 5 of the other end is connected;
Described sample gas generator 2 is one with the hollow airtight cavity of heating element heater, what hollow airtight cavity was provided with fluid sample bottle is removed and placed into mouth, fluid sample bottle be removed and placed into mouth by a lid that can open and close airtight, fluid sample bottle is contained in hollow airtight cavity.
Described ozonolysis reactions device 3 adjustable length, profile is non-directional screw type or U-shape structure, it is simple to ozone and long-chain olefin sample gas are sufficiently mixed reaction;
Heating element heater is electrical heating wire, heat tape or electrical heating block;
Sample gas generator 2 is that the stainless steel cylinder with rustless steel bottle cap, rustless steel bottle cap and rustless steel body are fastened by screw thread, and utilizes O-ring to seal, and inside holds fluid sample bottle.
Oxygen source 6 is the dry air after the steel cylinder equipped with oxygen or purification;
The ozone gas of producing of ozone generating-device 1 is high pure oxygen or dry air, and the uninterrupted of size of current and ozone gas processed that the concentration preparing ozone can pass through adjustment ozone generating-device 1 regulates.
Described reaction stream is given vent to anger the analytical equipment that detecting device 5 is direct gas sampling, is mainly the on-line mass spectroscopy instrument of gas sampling, is connected with ozonolysis reactions device 3 by gas conduit 9; Ozonolysis reactions flows out a part of sampling analysis of gas, and all the other are discharged as tail gas 15;
The cavity size of described sample gas generator 2 can with the size adjustment of long-chain olefin sample bottle, and cavity heating-up temperature can set according to the long-chain olefin boiling point height of research.
Quickly determine that in fluid sample, long-chain olefin position of double bond analyzes the application of process online, it is characterised in that:
A. will be equipped with putting into sample gas generator 2 containing the sample bottle of long-chain olefin liquid, sample gas generator 2 seals;
B. the substantially boiling point according to long-chain olefin contained in fluid sample, sets the heating-up temperature of sample gas generator 2: utilize temperature controller to control heating element heater, makes the temperature stabilization after the heating of setting sample gas generator 2;
C. open the gas outlet of feeder 4, pass in two pipelines, set the gas flow size of two pipelines, successively make gas respectively enter ozone generating-device 1 and sample gas generator 2;
D. open ozone generating-device 1 power supply, set current values, prepare ozone;
E. the ozone flowed out from ozone generating-device 1 enters ozonolysis reactions device 3 hybrid reaction together with the junction of long-chain olefin sample gas;
F. utilize reaction stream the to give vent to anger quick on-line sampling of partial reaction gas that ozonolysis reactions device 3 flows out by detecting device 2, it is thus achieved that long-chain olefin double bond is by the feature spectrogram of ozone decomposed afterproduct.
Described gas conduit 9 is quartz capillary or stainless steel capillary;
Described ozonolysis reactions device 3 is the pipeline of stainless steel, and non-cohesive material, it is to avoid the ozone corrosion to reaction pipeline.
Reaction stream gives vent to anger detecting device 2 for online gas sampling mass spectrograph, adopts Single-photon ionization (SPI) that reaction stream is given vent to anger and ionizes, and the method can simplify the spectrogram of ozonolysis product, it is simple to spectrum elucidation.
Wherein, the ozone concentration that ozone generating-device produces can occur the flow of electric current and high pure oxygen to be adjusted by adjustment. Ozonolysis reactions device adopts internal diameter to be about 4mm, and length is about the U-shaped stainless steel tube of 0.8m. Additionally, reaction stream give vent to anger detecting device adopt Single-photon ionization time of-flight mass spectrometer, this mass spectrograph adopts orthogonal acceleration design, detect with MCP detector, what reaction stream was given vent to anger is analyzed in part through the capillary tube one end entrance mass spectrograph being connected with the ozonolysis reactions device port of export, and all the other are discharged as waste gas. Wherein the air pressure of ionized region can be adjusted by the internal diameter and length changing capillary tube. In experiment, ionized region total gas pressure maintains about 30Pa.
Embodiment 1
A kind of quickly the device of long-chain olefin position of double bond and the examination of application performance is determined online for of the present invention, experiment is with the isomers of three kinds of long-chain decene for object, utilize this on-line analysis their ozonolysis product of device fast on-line analyzing, to determine position of double bond. It is set into high-purity O of ozone generating-device2Flow be 3.3L/min, generation electric current is 0.2A. By high-purity O of sample gas generator2Flow is 120ml/min, and rustless steel sample gas generator is in 100 DEG C. In experiment, the ionization mode of ionization source adopts VUV single-photon ionization (VUV-SPI), and ionized region air pressure maintains about 30Pa. Before this occur electric current be under 0A purge long-chain olefin sample gas enter mass spectrograph carry out ionization analyze, the sampling time is 15s. Afterwards, electric current being set to 0.2A, make ozone concentration begin to ramp up to stable, recycling mass spectrograph carries out sampling analysis afterwards. Fig. 2 is the SPI spectrogram of three kinds of long-chain decene isomerss and ozonolysis product thereof. It is found that the SPI spectrogram of three kinds of isomerss is single molecular ion peak, and their ozonolysis product spectrogram is widely different. SPI spectrogram in conjunction with the aldehyde material shown in Fig. 4, may determine that the ozonolysis product of 1-decene is aldehyde C-9, the ozonolysis product of cis-2-decene is acetaldehyde and octanal, the ozonolysis product of cis-5-decene is valeral, and this is consistent by the product of the principle gained of ozone decomposed with according to long-chain olefin double bond.
Embodiment 2
A kind of quickly the device of long-chain olefin position of double bond and the examination of application performance is determined online for of the present invention, experiment is with the isomers of three kinds of long-chain octenes for object, utilize this on-line analysis their ozonolysis product of device fast on-line analyzing, to determine position of double bond. It is set into high-purity O of ozone generating-device2Flow be 3.3L/min, generation electric current is 0.6A. By high-purity O of sample gas generator2Flow is 700ml/min, and rustless steel sample gas generator is in room temperature. In experiment, the ionization mode of ionization source adopts VUV single-photon ionization (VUV-SPI), and ionized region air pressure maintains about 30Pa. Before this occur electric current be under 0A purge long-chain olefin sample gas enter mass spectrograph carry out ionization analyze, the sampling time is 15s. Afterwards, electric current being set to 0.6A, make ozone concentration begin to ramp up to stable, recycling mass spectrograph carries out sampling analysis afterwards. Fig. 2 is the SPI spectrogram of three kinds of long-chain decene isomerss and ozonolysis product thereof. It is found that the SPI spectrogram of three kinds of isomerss is single molecular ion peak, and their ozonolysis product spectrogram is widely different. SPI spectrogram in conjunction with the aldehyde material shown in Fig. 4, may determine that the ozonolysis product of 1-octene is enanthaldehyde, the ozonolysis product of cis-2-octene is acetaldehyde and hexanal, the ozonolysis product of cis-3-octene is propionic aldehyde and valeral, and this is consistent by the product of the principle gained of ozone decomposed with according to long-chain olefin double bond.
Claims (9)
1. the device quickly determining long-chain olefin position of double bond online, it is characterised in that:
Give vent to anger detecting device (5) including ozone generating-device (1), sample gas generator (2), ozonolysis reactions device (3), feeder (4) and reaction stream;
Wherein, described feeder (4) includes oxygen source (6), the gas outlet of oxygen source (6) is connected with the carrier gas inlet of the gas access of ozone generating-device (1) and sample gas generator (2) respectively through two pipelines, is respectively equipped with mass flow controller (7) on two pipelines;
The ozone outlet of ozone generating-device (1) is all connected with the gas access of ozonolysis reactions device (3) with the gas outlet of sample gas generator (2);
Give vent to anger with the reaction stream gas sampling mouth of detecting device (5) of the gas outlet of ozonolysis reactions device (3) is connected.
2. device according to claim 1, it is characterised in that:
Described ozonolysis reactions device (3) is copper pipe or stainless steel tube, its one end is connected with the ozone outlet of ozone generating-device (1) and the gas outlet of sample gas generator (2), and give vent to anger with the reaction stream gas sampling mouth of detecting device (5) of the other end is connected;
Described sample gas generator (2) is one with the hollow airtight cavity of heating element heater, what hollow airtight cavity was provided with fluid sample bottle is removed and placed into mouth, fluid sample bottle be removed and placed into mouth by a lid that can open and close airtight, fluid sample bottle is contained in hollow airtight cavity.
3. device according to claim 2, it is characterised in that:
Described ozonolysis reactions device (3) adjustable length, profile is non-directional screw type or U-shape structure, it is simple to ozone and long-chain olefin sample gas are sufficiently mixed reaction;
Heating element heater is electrical heating wire, heat tape or electrical heating block;
Sample gas generator (2) is that the stainless steel cylinder with rustless steel bottle cap, rustless steel bottle cap and rustless steel body are fastened by screw thread, and utilizes O-ring to seal, and inside holds fluid sample bottle.
4. device according to claim 1, it is characterised in that:
Oxygen source (6) is the dry air after the steel cylinder equipped with oxygen or purification;
The ozone gas of producing of ozone generating-device (1) is high pure oxygen or dry air, and the uninterrupted of size of current and ozone gas processed that the concentration preparing ozone can pass through adjustment ozone generating-device (1) regulates.
5. device according to claim 1, it is characterised in that:
Described reaction stream is given vent to anger the analytical equipment that detecting device (5) is direct gas sampling, is mainly the on-line mass spectroscopy instrument of gas sampling, is connected with ozonolysis reactions device (3) by gas conduit (9); Ozonolysis reactions flows out a part of sampling analysis of gas, and all the other are discharged as tail gas (15).
6. device according to claim 1, it is characterised in that:
The cavity size of described sample gas generator (2) can with the size adjustment of long-chain olefin sample bottle, and cavity heating-up temperature can set according to the long-chain olefin boiling point height of research.
7. the arbitrary described device of claim 1-6 is quickly determining that in fluid sample, long-chain olefin position of double bond analyzes the application of process online, it is characterised in that:
Adopt arbitrary described device in claim 1-6 to be operated, comprise the steps:
A. will be equipped with putting into sample gas generator (2) containing the sample bottle of long-chain olefin liquid, sample gas generator (2) seals;
B. the substantially boiling point according to long-chain olefin contained in fluid sample, sets the heating-up temperature of sample gas generator (2): utilize temperature controller to control heating element heater, makes the temperature stabilization after setting sample gas generator (2) heating;
C. open the gas outlet of feeder (4), pass in two pipelines, set the gas flow size of two pipelines, successively make gas respectively enter ozone generating-device (1) and sample gas generator (2);
D. open ozone generating-device (1) power supply, set current values, prepare ozone;
E. the ozone flowed out from ozone generating-device (1) enters ozonolysis reactions device (3) hybrid reaction together with the junction of long-chain olefin sample gas;
F. utilize reaction stream the to give vent to anger quick on-line sampling of partial reaction gas that ozonolysis reactions device (3) flows out by detecting device (2), it is thus achieved that long-chain olefin double bond is by the feature spectrogram of ozone decomposed afterproduct.
8. application according to claim 7, it is characterised in that:
Described gas conduit (9) is quartz capillary or stainless steel capillary;
The pipeline that described ozonolysis reactions device (3) is stainless steel, and non-cohesive material, it is to avoid the ozone corrosion to reaction pipeline.
9. application according to claim 7, it is characterised in that:
Reaction stream gives vent to anger detecting device (2) for online gas sampling mass spectrograph, adopts Single-photon ionization (SPI) that reaction stream is given vent to anger and ionizes, and the method can simplify the spectrogram of ozonolysis product, it is simple to spectrum elucidation.
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| CN110887713A (en) * | 2019-12-04 | 2020-03-17 | 湖南农业大学 | Dark tea brown reference substance and application thereof |
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| US20100267148A1 (en) * | 2007-06-04 | 2010-10-21 | The University Of Wollongong | Method for the determination of the position of unsaturation in a compound |
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Application publication date: 20160601 |