CN110426384A - The method for detecting specificity of 4- tert-butyl catechol in olefinic monomer - Google Patents
The method for detecting specificity of 4- tert-butyl catechol in olefinic monomer Download PDFInfo
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- CN110426384A CN110426384A CN201910733221.2A CN201910733221A CN110426384A CN 110426384 A CN110426384 A CN 110426384A CN 201910733221 A CN201910733221 A CN 201910733221A CN 110426384 A CN110426384 A CN 110426384A
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- tert
- butyl catechol
- semiconducting compound
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- sers active
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/01—Arrangements or apparatus for facilitating the optical investigation
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/65—Raman scattering
- G01N21/658—Raman scattering enhancement Raman, e.g. surface plasmons
Abstract
The present invention provides a kind of method for detecting specificity of 4- tert-butyl catechol in olefinic monomer, it include: using semiconducting compound as SERS active-substrate material, after SERS active-substrate material is contacted with 4- tert-butyl catechol as the olefin samples of polymerization inhibitor, with Raman spectrometer detect determine 4- tert-butyl catechol content the step of.The semiconducting compound, selectable range is wide, at low cost, easy to operate, quickly and effectively, generates specific Raman reinforcing effect to the polymerization inhibitor 4- tert-butyl catechol in olefinic monomer, can be realized the specific detection to 4- tert-butyl catechol；Can also effectively recognition detection go out the polymerization inhibitor 4- tert-butyl catechol in olefinic monomer, the level of inhibitor in olefinic monomer can be modulated in time, guarantee the quality of olefinic monomer.
Description
Technical field
The present invention relates to 4- tert-butyl o benzene in semiconducting compound base material field more particularly to a kind of olefinic monomer
The method for detecting specificity of diphenol.
Background technique
4- tert-butyl catechol is high-efficiency polymerization inhibitor when olefinic monomer is distilled or stored and transported, particularly for styrene, fourth
The monomers such as diene, chlorobutadiene, isoprene.It is also used for vinyl chloride, vinylpyridine, alpha-olefin, nonene, cyclopentadiene, different
Pentadiene, acrylic acid, methacrylic acid and its esters, chlorinated alkenes, polyurethane etc..Due to the addition of 4- tert-butyl catechol
Amount, can neither be excessively high, can not be too low, too low, and the effect of polymerization inhibitor is not achieved, if excessively high, on the one hand will affect product isoamyl
On the other hand the quality of diene then will increase production cost, so, it is very heavy to the measurement of 4- tert-butyl catechol in alkene
It wants.There are mainly two types of currently used measuring methods: gas chromatography and spectrophotometry.However these methods are more or less
There are some defects, such as require height, detection sensitivity poor detection system, specific detection more difficulty etc..Therefore
Develop one kind rapidly and efficiently, it is easy to operate, and the polymerization inhibitor 4- tert-butyl catechol in olefinic monomer can directly be carried out
The method of specific detection is significant.
Summary of the invention
The main purpose of the present invention is to provide a kind of specific detection sides of 4- tert-butyl catechol in olefinic monomer
Method.
The technical scheme of the present invention is realized as follows:
The method for detecting specificity of 4- tert-butyl catechol in a kind of olefinic monomer, it is characterised in that the method includes
Using semiconducting compound as SERS active-substrate material, using SERS active-substrate material and 4- tert-butyl catechol as resistance
Poly- agent olefin samples contact after, with Raman spectrometer detect determine 4- tert-butyl catechol content the step of.
Further, the semiconducting compound presoma includes WO2、W18O49、WO3、MoO2、MoO3-x、MoO3、ZnO、
TiO2、Cu2One of O or a variety of；Wherein x value range is 0~2.
Further, in the SERS active-substrate material semiconducting compound with crystal or noncrystal or crystal with
Noncrystal Coexistence mode；Semiconductor chemical combination in the SERS active-substrate material comprising stoichiometric ratio or non-stoichiometric
Object.
Further, the preparation method of the SERS active-substrate material includes:
A) solvent-thermal method prepares the step of semiconducting compound presoma: making organic comprising metal chloride, ammonium salt, metal
The reaction system of reagent or metal oxide and solvent is obtained in 160~200 DEG C of progress alcoholysis and hydrolysis 12~for 24 hours
Semiconducting compound presoma.
Further, the preparation method of the SERS active-substrate material further include:
B1) annealing steps: in A) step obtain semiconducting compound presoma after in 400~600 DEG C make annealing treatment 4~
6h。
Further, the preparation method of the SERS active-substrate material further include:
B2) phosphorus regulate and control annealing steps: in A) step obtain semiconducting compound presoma after be added phosphorus source in 400~600
DEG C annealing 4~6h.
Further, the atmosphere that the annealing uses is selected from reducing atmosphere and/or oxidizing atmosphere；
Further, the reducing atmosphere includes one or more of hydrogen, argon gas, ammonia；
Further, the oxidizing atmosphere includes air atmosphere and/or oxygen atmosphere.
Further, the detection method specifically includes:
(1) SERS active-substrate material is configured to base material solution；
(2) base material solution and olefin samples are mixed, until adsorption equilibrium；
(3) mixed solution of adsorption equilibrium is added dropwise in clean Si/SiO2On substrate, after natural drying, in Raman light
It is tested on spectrometer.
Further, the base material solution is using ethyl alcohol as solvent, by the way that compound semiconductor material is distributed to second
In alcohol, base material solution is obtained.
The present invention provides a kind of applications including above-mentioned semiconducting compound base material, by the semiconducting compound
After base material is contacted with 4- tert-butyl catechol as the alkene test sample of polymerization inhibitor, with Raman spectrometer to alkene list
Polymerization inhibitor 4- tert-butyl catechol in body directly carries out specific detection.
Compared with prior art, beneficial effects of the present invention at least that:
1) compared with noble metal base material, semiconducting compound provided by the invention as SERS active-substrate material,
Selectable range is wide, at low cost, easy to operate, and quickly and effectively, semiconducting compound can be to the polymerization inhibitor 4- in olefinic monomer
Tert-butyl catechol generates specific Raman reinforcing effect, can be realized the specific detection to 4- tert-butyl catechol；
2) present invention can also effectively recognition detection go out the polymerization inhibitor 4- tert-butyl catechol in olefinic monomer, can and
When the level of inhibitor in olefinic monomer is modulated, guarantee the quality of olefinic monomer.
Detailed description of the invention
The accompanying drawings constituting a part of this application is used to provide further understanding of the present application, and the application's shows
Meaning property embodiment and its explanation are not constituted an undue limitation on the present application for explaining the application.In the accompanying drawings:
Fig. 1 is in the embodiment of the present invention 1 with TiO2As SERS active-substrate, to probe molecule 4- tert-butyl catechol
Enhancing Raman spectrogram, excitation wavelength 532nm；
Fig. 2 is TiO in the embodiment of the present invention 22And the homojunction TiO of phosphorus regulation2To probe molecule 4- tert-butyl o benzene two
The enhancing Raman spectrogram of phenol, optical maser wavelength 532nm；
Fig. 3 is TiO in the embodiment of the present invention 32And the TiO of hydrogen annealing processing2To probe molecule 4- tert-butyl o benzene two
The enhancing Raman spectrogram of phenol, optical maser wavelength 532nm；
Fig. 4 is TiO in the embodiment of the present invention 42And the homojunction TiO of phosphorus regulation2To polymerization inhibitor uncle 4- in isoprene
The enhancing Raman spectrogram of butyl-catechol molecule, optical maser wavelength 532nm；
Fig. 5 is TiO in the embodiment of the present invention 52And the TiO of hydrogen reducing2To the polymerization inhibitor 4- tert-butyl in isoprene
The enhancing Raman spectrogram of catechol molecule, optical maser wavelength 532nm.
Specific embodiment
It is noted that following detailed description is all illustrative, it is intended to provide further instruction to the application.Unless another
It indicates, all technical and scientific terms used herein has usual with the application person of an ordinary skill in the technical field
The identical meanings of understanding.It should be noted that in the absence of conflict, the features in the embodiments and the embodiments of the present application
It can be combined with each other.The application is described in detail below with reference to the accompanying drawings and in conjunction with the embodiments.
It should be noted that term used herein above is merely to describe specific embodiment, and be not intended to restricted root
According to the illustrative embodiments of the application.As used herein, unless the context clearly indicates otherwise, otherwise singular
Also it is intended to include plural form, additionally, it should be understood that, when in the present specification using term "comprising" and/or " packet
Include " when, indicate existing characteristics, step, operation, device, component and/or their combination.
As the one aspect of technical solution of the present invention, involved in be a kind of tertiary fourth of polymerization inhibitor 4- in olefinic monomer
Base catechol specific detection semiconducting compound SERS active-substrate material, it includes semiconducting compound, described half
The preparation method of conductor compound includes:
Using solvent-thermal method, directly obtain metal chloride, ammonium salt, organometallic reagent or reactive metal oxide
Semiconducting compound base material；Alternatively, first obtaining semiconducting compound presoma using solvent-thermal method, make annealing treatment later,
Obtain the semiconducting compound base material with different stoichiometric ratios；Alternatively, first obtaining semiconductor transformation using solvent-thermal method
Object presoma is closed, phosphorus source is added later in 400~600 DEG C of 4~6h of annealing, obtains the homojunction semiconductor chemical combination of phosphorus regulation
Object base material.
In some embodiments, the preparation method of the semiconducting compound includes:
Using solvent-thermal method, metal chloride, ammonium salt, organometallic reagent or metal oxide etc. may be selected as former
Material reacts 12 at 160~200 DEG C~for 24 hours in anhydrous ethanol solvent, directly by the reaction process such as alcoholysis and hydrolysis
To semiconducting compound base material；Alternatively, first obtaining semiconducting compound presoma using solvent-thermal method, then 400~600
DEG C annealing 4~6h, obtain accordingly with different stoichiometric ratios semiconducting compound base material.
The metal chloride is selected from one or more kinds of any combination of tungsten hexachloride, titanium tetrachloride；It is described
Ammonium salt is selected from ammonium molybdate；The organometallic reagent be selected from acetyl acetone, butyl titanate it is one or more kinds of
Any combination；The metal oxide is selected from titanium oxide, tungsten oxide, one or more kinds of any combination of molybdenum oxide.
In some embodiments, the preparation of the semiconducting compound base material of different oxygen defect concentration, with semiconductor
Compound is wide as SERS active-substrate material selectable range, can be but is not limited only to WO2、W18O49、WO3、MoO2、
MoO3-x、MoO3、ZnO、TiO2、Cu2Any one or two or more combinations in the compound semiconductor materials such as O is as forerunner
Body is also possible to the semiconducting compound of other stoichiometric ratios or non-stoichiometric.In hydrogen, argon gas, ammonia etc. one
In kind or the mixed gas of several gases, different temperatures, time are made annealing treatment；Wherein x value range is 0~2.
In some embodiments, the annealing annealing atmosphere may be selected reducing atmosphere, as hydrogen, argon gas,
The gaseous mixture of the one or several kinds gas such as ammonia；Or oxidizing atmosphere, such as air, oxygen, the purpose is to be had
The semiconducting compound SERS active-substrate material of different stoichiometric ratios.
In some embodiments, the polymerization inhibitor 4- tert-butyl catechol method for detecting specificity in the olefinic monomer
Include:
It will be dispersed with the solution of certain content semiconducting compound base material, contains 4- tert-butyl o with certain density
The alkene of benzenediol polymerization inhibitor directly mixes, and reaches adsorption equilibrium.Then, take a certain amount of mixed solution drop in cleaning
On silicon wafer after drying, it is able to use Raman spectrometer and directly 4- tert-butyl catechol is detected, and to 4- tert-butyl o
Benzenediol has apparent Raman reinforcing effect, being capable of efficient identification 4- tert-butyl catechol.
Further, the compound semiconductor material of preparation is distributed in a certain amount of ethyl alcohol, obtains semiconducting compound
The ethanol solution of material.Then a certain amount of solution is taken, the 4- tert-butyl catechol ethanol solution of various concentration, dark place is added
It stands, after reaching adsorption equilibrium, takes a certain amount of mixed solution drop on clean Si/SiO2 substrate, after natural drying, drawing
It is tested on graceful spectrometer, collects data.
Further, compound semiconductor material of the invention can go out micro uncle 4- contained in alkene with specific detection
Butyl-catechol.
Embodiment 1
A certain amount of butyl titanate is dissolved into a certain amount of ethyl alcohol, 180 DEG C, reacts 12h, naturally cool to room
Temperature.Centrifugation, washing vacuum drying obtain TiO2Presoma, it is 2mg/mL's that 4- tert-butyl catechol, which is added to 3mL concentration,
TiO2Ethanol solution in, stand 2h, after adsorption equilibrium, 20 μ L mixed solutions taken to be dripped respectively in clean Si/SiO2On substrate,
Natural drying obtains template 1 to be measured.
As shown in Figure 1, being in the present embodiment with TiO2As SERS active-substrate, to probe molecule 4- tert-butyl o benzene two
The enhancing Raman spectrogram of phenol, excitation wavelength 532nm.
Embodiment 2
A certain amount of butyl titanate is dissolved into a certain amount of ethyl alcohol, 180 DEG C, reacts 12h, naturally cool to room
Temperature.Centrifugation, washing vacuum drying obtain TiO2Presoma, then by TiO2Under conditions of a waterside sodium phosphite is as phosphorus source,
At a temperature of 300-500 DEG C, 1-5h is kept, prepares the homojunction TiO of phosphorus regulation2.By same amount of 4- tert-butyl catechol, divide
It is not added to 3mL TiO2The homojunction TiO that ethanol solution, phosphorus regulate and control2Ethanol solution stands 2h, after adsorption equilibrium, takes 20 μ L mixed
Solution is closed to be dripped respectively in clean Si/SiO2On substrate, natural drying obtains template 2 to be measured.
As shown in Fig. 2, being TiO in the present embodiment2Substrate and the homojunction TiO of phosphorus regulation2To 4- tert-butyl catechol
The enhancing Raman spectrogram of probe molecule, optical maser wavelength 532nm.
Embodiment 3
A certain amount of butyl titanate is dissolved into a certain amount of ethyl alcohol, 180 DEG C, reacts 12h, naturally cool to room
Temperature.Centrifugation, washing vacuum drying obtain TiO2Presoma, then by TiO2In a hydrogen atmosphere, it at a temperature of 300-500 DEG C, keeps
1-5h prepares the titanium oxide of the oxygen defect of hydrogen reducing.By same amount of 4- tert-butyl catechol, it is added separately to 3mL
TiO2Ethanol solution, hydrogen reducing oxygen defect titanium oxide ethanol solution, stand 2h, after adsorption equilibrium, take 20 μ L mixing molten
Liquid is dripped respectively in clean Si/SiO2On substrate, natural drying obtains template 3 to be measured.
As shown in figure 3, being TiO in the present embodiment2The titanium oxide of the oxygen defect of substrate and hydrogen reducing is to 4- tert-butyl
The enhancing Raman spectrogram of catechol probe molecule, optical maser wavelength 532nm.
Embodiment 4
A certain amount of butyl titanate is dissolved into a certain amount of ethyl alcohol, 180 DEG C, reacts 12h, naturally cool to room
Temperature.Centrifugation, washing vacuum drying obtain TiO2Presoma, then by TiO2Under conditions of a waterside sodium phosphite is as phosphorus source,
At a temperature of 300-500 DEG C, 1-5h is kept, prepares the homojunction TiO of phosphorus regulation2.Contain 4- tert-butyl o benzene two for same amount of
The isoprene of phenol stabilizers is added separately to 3mL TiO2The homojunction TiO that ethanol solution, phosphorus regulate and control2Ethanol solution is stood
2h after adsorption equilibrium, takes 20 μ L mixed solutions to be dripped respectively in clean Si/SiO2On substrate, natural drying obtains template to be measured
4。
As shown in figure 4, being TiO in the present embodiment2Substrate and the homojunction TiO of phosphorus regulation2To contain 4- tert-butyl o benzene
The enhancing Raman spectrogram of the isoprene of two phenol stabilizers, optical maser wavelength 532nm.
Embodiment 5
A certain amount of butyl titanate is dissolved into a certain amount of ethyl alcohol, 180 DEG C, reacts 12h, naturally cool to room
Temperature.Centrifugation, washing vacuum drying obtain TiO2Presoma, then by TiO2In a hydrogen atmosphere, it at a temperature of 300-500 DEG C, keeps
1-5h prepares the titanium oxide of the oxygen defect of hydrogen reducing.By same amount of isoamyl containing 4- tert-butyl catechol stabilizer
Diene is added separately to 3mL TiO2Ethanol solution, hydrogen reducing oxygen defect titanium oxide ethanol solution, stand 2h, absorption
After balance, 20 μ L mixed solutions is taken to be dripped respectively in clean Si/SiO2On substrate, natural drying obtains template 5 to be measured.
As shown in figure 5, being TiO in the present embodiment2The titanium oxide of the oxygen defect of substrate and hydrogen reducing to contain uncle 4-
The enhancing Raman spectrogram of the isoprene of butyl-catechol stabilizer, optical maser wavelength 532nm.
Embodiment 6
A certain amount of butyl titanate is dissolved into a certain amount of ethyl alcohol, 180 DEG C, reacts 12h, naturally cool to room
Temperature.Centrifugation, washing vacuum drying obtain TiO2Presoma, then by TiO2In air atmosphere, it at a temperature of 300-500 DEG C, keeps
1-5h prepares the titanium oxide of certain oxygen defect concentration.By same amount of isoamyl two containing 4- tert-butyl catechol stabilizer
Alkene is added separately to 3mL TiO2The titanium oxide ethanol solution of ethanol solution, certain oxygen defect concentration stands 2h, adsorption equilibrium
Afterwards, 20 μ L mixed solutions is taken to be dripped respectively in clean Si/SiO2On substrate, natural drying obtains template to be measured.
The present invention is mainly active using the semiconducting compound of a variety of stoichiometric ratios and non-stoichiometric as SERS
Base material realizes the direct quick specific detection to 4- tert-butyl catechol.And compound semiconductor material is being drawn
In graceful detection can greatly Selective long-range DEPT 4- tert-butyl catechol Raman response signal, with noble metal base SERS chip phase
When than compensating for the defect of noble metal base SERS chip in practical applications, promoting semiconducting compound base material and exist
Practical application in the field SERS.
In addition, inventor also utilize it is corresponding in the alternate embodiments 1-6 such as above listed other process conditions
Process conditions have carried out corresponding test, the content of required verifying and close with embodiment 1-6 product.So herein not to each
The verifying content of a embodiment is explained one by one, and only illustrates the excellent place of the present patent application using Examples 1 to 6 as representative.
The foregoing is merely preferred embodiment of the present application, are not intended to limit this application, for the skill of this field
For art personnel, various changes and changes are possible in this application.Within the spirit and principles of this application, made any to repair
Change, equivalent replacement, improvement etc., should be included within the scope of protection of this application.
Claims (10)
1. the method for detecting specificity of 4- tert-butyl catechol in a kind of olefinic monomer, it is characterised in that the method includes with
Semiconducting compound is as SERS active-substrate material, using SERS active-substrate material and 4- tert-butyl catechol as polymerization inhibitor
Agent olefin samples contact after, with Raman spectrometer detect determine 4- tert-butyl catechol content the step of.
2. detection method according to claim 1, it is characterised in that the presoma of the semiconducting compound includes WO2、
W18O49、WO3、MoO2、MoO3-x、MoO3、ZnO、TiO2、Cu2One of O or a variety of；Wherein x value range is 0~2.
3. detection method according to claim 1, it is characterised in that semiconductor chemical combination in the SERS active-substrate material
Object is with crystal or noncrystal or crystal and noncrystal Coexistence mode；It include stoichiometry in the SERS active-substrate material
Than or non-stoichiometric semiconducting compound.
4. detection method according to claim 1, it is characterised in that the preparation method packet of the SERS active-substrate material
It includes:
A) solvent-thermal method prepares the step of semiconducting compound presoma: making comprising metal chloride, ammonium salt, organometallic reagent
Or the reaction system of metal oxide and solvent is partly led in 160~200 DEG C of progress alcoholysis and hydrolysis 12~for 24 hours
Body compounds precursors.
5. detection method according to claim 4, it is characterised in that the preparation method of the SERS active-substrate material is also
Include:
B1) annealing steps: in A) step obtain semiconducting compound presoma after in 400~600 DEG C of 4~6h of annealing.
6. detection method according to claim 4, it is characterised in that the preparation method of the SERS active-substrate material is also
Include:
B2) phosphorus regulate and control annealing steps: in A) step obtain semiconducting compound presoma after be added phosphorus source moved back in 400~600 DEG C
4~6h of fire processing.
7. wanting the described in any item detection methods of 5-6 according to right, which is characterized in that the atmosphere that the annealing uses is selected from
Reducing atmosphere and/or oxidizing atmosphere.
8. detection method according to claim 7, which is characterized in that the reducing atmosphere includes hydrogen, argon gas, in ammonia
One or more.
9. wanting the preparation method of the 7 semiconducting compound base materials according to right, which is characterized in that the oxidizing atmosphere
Including air atmosphere and/or oxygen atmosphere.
10. according to right want 1 described in detection method, which is characterized in that the detection method specifically includes:
(1) SERS active-substrate material is configured to base material solution；
(2) base material solution and olefin samples are mixed, until adsorption equilibrium；
(3) mixed solution of adsorption equilibrium is added dropwise in clean Si/SiO2On substrate, after natural drying, on Raman spectrometer
Test.
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