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WO2014069897A1 - Détecteur d'identification d'hydrocarbures, son procédé de fabrication et application - Google Patents

Détecteur d'identification d'hydrocarbures, son procédé de fabrication et application Download PDF

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Publication number
WO2014069897A1
WO2014069897A1 PCT/KR2013/009738 KR2013009738W WO2014069897A1 WO 2014069897 A1 WO2014069897 A1 WO 2014069897A1 KR 2013009738 W KR2013009738 W KR 2013009738W WO 2014069897 A1 WO2014069897 A1 WO 2014069897A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydrocarbon
group
identification sensor
swellable
hydrocarbon identification
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2013/009738
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English (en)
Korean (ko)
Inventor
김종만
이찬우
박동훈
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Industry University Cooperation Foundation IUCF HYU
Original Assignee
Industry University Cooperation Foundation IUCF HYU
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020130126202A external-priority patent/KR101516600B1/ko
Application filed by Industry University Cooperation Foundation IUCF HYU filed Critical Industry University Cooperation Foundation IUCF HYU
Publication of WO2014069897A1 publication Critical patent/WO2014069897A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
    • G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
    • G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
    • 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
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
    • G01N31/22—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/26—Oils; Viscous liquids; Paints; Inks
    • G01N33/28—Oils, i.e. hydrocarbon liquids
    • G01N33/2835—Specific substances contained in the oils or fuels

Definitions

  • the present invention relates to a hydrocarbon identification sensor, a manufacturing method thereof, and a use thereof.
  • the present invention relates to a hydrocarbon identification sensor for identifying hydrocarbons using a swellable hydrocarbon absorber and an external stimulus that are embolized or exhibited fluorescence, and a manufacturing method and a use thereof.
  • Hydrocarbons in which the carbon-to-carbon bond is a single bond are called saturated hydrocarbons.
  • Saturated hydrocarbons that can be obtained in the process of fractional distillation of petroleum, which are included in fossil fuels such as petroleum, are very stable and have very low reaction properties, so they are not easy to distinguish. Mass spectrometry, gas chromatography, Professional methods, such as distillation, are used.In addition, when analyzing similar diesel fuels (petroleum-containing kerosene) made of a mixture of kerosene and kerosene, densities are measured, or distillation and gas chromatography columns are used. .
  • Petroleum consisting of these hydrocarbons is not readily fractionated because the structure is difficult to fractionate from isomers, especially in the case of kerosene and diesel, because the number of carbons contained in the components is not significantly different, which is more difficult to discern today.
  • Small quantities of identifiers are added to kerosene and diesel products to distinguish them.However, the substances used as identifiers are easily removed by activated carbon or clay, and once the identifiers are removed, the petroleum products can only be analyzed using expensive equipment. The general public is difficult to use.
  • Japanese Patent No. 3841513 discloses a limiting current hydrocarbon sensor using barium cerium oxide as a solid electrolyte, but it is difficult for the general public to use, and there is a difference from the present invention in the solution.
  • the present invention provides a hydrocarbon identification sensor, a manufacturing method and a use thereof, which can reduce costs and improve working efficiency by making it easy to use in a simple manner without expensive and complicated equipment. problem solving means,
  • a hydrocarbon identification sensor manufacturing method is a hydrocarbon having swelling property.
  • Step c Mixing the diacetylene monomer in the absorbent material (step a); exposing the mixture of step a to photopolymerizing the die acetylene monomer (step b); and mixing the curing agent with the photopolymerized mixture in step b.
  • another method for producing a hydrocarbon identification sensor comprises the steps of: mixing a diacetylene monomer in a swellable hydrocarbon absorbent (step a; mixing a hardener with a mixture of step a ' above (step b) And photopolymerizing the diacetylene monomer by exposing the mixture of step b ' (step c').
  • the swellable hydrocarbon absorber may be polydimethylsiloxane.
  • the diacetylene monomer may be a compound represented by Chemical Formula i, and preferably PCDA (10,12-Pentacosadiynoic acid).
  • e + f is an integer from 2 to 50, e and f are integers of 1 or more,
  • a and B are methyl group, amine group, carboxyl group, hydroxy group, maleimide group, biotin group, N-hydroxysuccinimide group, benzoic acid group or activated ester group.
  • [18] L may be the same or different from each other, and may include one or more selected from the group consisting of an alkyl group having 2 or more carbon atoms, at least one ethylene oxide group, an amine group, an amide group, an ester group and a carbonyl group. .
  • the step a or step a ′ may be performed by mixing a diacetylene monomer in a powder state with a swellable hydrocarbon absorbent or in a swellable hydrocarbon absorbent after dissolving a diacetylene monomer in an organic solvent.
  • the organic solvent is chloroform, dichloromethane, tetrahydrofuran, benzene,
  • the exposure may be performed by exposing a line of 150 to 350 nm for 1 to 600 seconds or gamma rays.
  • the exposure is carried out to polymerize the diacetylene monomer.
  • the monomer type is different.
  • the diacetylene monomer is properly adjusted by adjusting the exposure time in the above range. Can be polymerized.
  • the swellable hydrocarbon absorber and the hardener may be combined in a weight ratio of 1: 1 to 10: 1.
  • a polydiacetylene is added to a swellable hydrocarbon absorbent.
  • a fixed hydrocarbon identification sensor can be provided.
  • the hydrocarbon identification sensor may be in the form of a polymer film.
  • the swellable hydrocarbon absorber may be polydimethylsiloxane.
  • the polydiacetylene may be a photopolymerized diacetylene monomer.
  • the diacetylene monomer may be a compound represented by the following Chemical Formula 1.1, preferably PCDA (10,12-Pentacosaciiynoicacicl). .
  • e + f is an integer from 2 to 50, e and f are integers of 1 or more,
  • a and B are methyl, amine, carboxyl, hydroxy, maleimide, biotin,
  • L and and may be the same or different, and may include one or more selected from the group consisting of an alkyl group having 2 or more carbon atoms, at least one ethylene oxide group, an amine group, an amide group, an ester group and a carbonyl group. .
  • the hydrocarbon identification sensor may be a swellable hydrocarbon absorber that absorbs hydrocarbons and swells to stimulate the immobilized polydiacetylene to exhibit color transition or fluorescence.
  • the hydrocarbon identification sensor can identify hydrocarbons according to carbon number.
  • a swellable hydrocarbon absorber [37] According to another embodiment of the present invention, a swellable hydrocarbon absorber
  • a method of identifying a hydrocarbon in a sample through a color transition or fluorescence change indicated by the polydiacetylene-immobilized hydrocarbon identification sensor in a container containing a sample; and the hydrocarbon identification sensor absorbing hydrocarbon and swelling. have.
  • the above method can identify hydrocarbons according to carbon number.
  • a method of identifying gasoline, diesel and kerosene using the hydrocarbon identification method may be provided.
  • a method of identifying the structural isomers of hydrocarbon using the hydrocarbon identification method may be provided. have.
  • the hydrocarbon identification sensor is introduced into a material containing hydrocarbon, and then left for a predetermined time (for example, from 1 second to 60 minutes).
  • Absorbents e.g. PDMS
  • PDMS Absorbents
  • swelling Stimulates polydiacetylene, which causes the sensor to transition from blue to red and fluorescence in the red state, where every carbon number of hydrocarbons
  • Hydrocarbons having a ring shape also have different degrees of embolism or fluorescence, and thus, the structural isomers of hydrocarbons can be visually identified by the above method.
  • This principle of operation is applicable to the field of materials consisting of saturated hydrocarbons and, in particular, in petroleum products consisting of saturated hydrocarbons.
  • the petroleum products contain saturated hydrocarbons with 4 to 12 carbons, 9 to 16 kerosene and 14 to 23 carbons.
  • analogous diesel refers to diesel containing kerosene. Since kerosene and diesel are not easily distinguished, the largest proportion of the types of manufacturing of analogous diesel is the way of mixing kerosene and diesel.
  • hydrocarbons made from hydrocarbons have a difficult problem to identify, especially in the case of kerosene and diesel, because the carbon number of the components is not so different that it is very difficult to identify them.
  • the present invention uses a material that swells as it absorbs hydrocarbons and a substance that has embolism or fluorescence expression characteristics by the swelling, so that the hydrocarbon can be identified in a very simple manner according to the difference between the degree of swelling, color change, and fluorescence expression.
  • the petroleum products such as gasoline, kerosene and diesel can be identified, and the detection of similar diesel fuels (kerosene containing kerosene) is also a social problem.
  • the color shift is caused by a swellable hydrocarbon absorber and external stimulation.
  • a swellable hydrocarbon absorber and external stimulation it is possible to easily identify hydrocarbons with the naked eye anywhere without expensive and complicated equipment by using fluorescence-representing materials.
  • the structure of difficult-to-identify saturated hydrocarbons is easily identified, especially according to the present invention.
  • hydrocarbons can be visually identified in a simple manner without expensive and complicated equipment, and thus can be easily used by the general public.
  • FIG 1 shows the color of the hydrocarbon identification sensor according to the present invention as it absorbs hydrocarbons.
  • FIG. 2 and FIG. 3 show the results of FIG. 1 analyzed by Photoshop, and FIG. 4 and FIG. 5 show the origin.
  • FIG. 6 shows visual observation results (a) and origin analysis results (b) of a hydrocarbon identification sensor indicating a color transition by absorbing hydrocarbons.
  • Figure 9 is a view of the octane using a hydrocarbon identification sensor according to the present invention.
  • FIG. 10 is a view illustrating octane using a hydrocarbon identification sensor according to the present invention.
  • FIG. 1 i illustrates the analysis of oil using a hydrocarbon identification sensor according to the present invention.
  • FIG. 12 is a visual observation of embolism between genuine kerosene and genuine diesel oil identified by a hydrocarbon identification sensor according to the present invention.
  • FIG. 13 is a graph illustrating the metabolic phenomena of gas oils based on the addition of kerosene identified by a hydrocarbon identification sensor according to the present invention. ((a) is the result of visual observation, (b) is the result of origin analysis)
  • PDMS Polydimethylsiloxane
  • PCD A (10,12-Pentacosadynoic acid) among several diacetylene monomers.
  • Genie uses Sylgard 184.
  • This product consists of a base and a hardener, and this product has a characteristic of hardening when mixed in a ratio of 10: 1 (base: hardener).
  • the manufacturing method of the sensor was carried out as follows. 20 g of PDMS base was placed in a container, and 50 mg of PCDA monomer was dissolved in 2 mL of chloroform to prepare a solution. The solution was placed in the PDMS base so that all of the chloroform could evaporate.
  • the mixture was mixed for 10 minutes. Next, in order to polymerize the PCDA monomers, it was exposed to 254 ultraviolet rays for 1 minute to make blue polydiacetylene (PDA). In this state, it was not cured and became a highly viscous liquid. In order to harden the PDMS, to make it more useful solid form, 2 g of PDMS hardener was added and mixed well. Then, the square petidish was cured at room temperature for 2 days to give a blue transparent film form. A hydrocarbon identification sensor was fabricated.
  • PDA polydiacetylene
  • the hydrocarbon identification sensor manufactured according to the example was cut to a size of 1 cm X 2 cm and the following experiment was carried out.
  • Saturated hydrocarbon of tetradecane (C I4 H 30 ) having 5 carbon atoms (H I2 ) to 14 carbon atoms was carried out.
  • 4 mL of each hydrocarbon was placed in a transparent vessel (4 mL vial) to check the degree of swelling and discoloration of the sensor. Then, the sensor was placed in the transparent vessel (4 mL vial) and observed.
  • the results are shown in Fig. 1. The smaller the carbon number, the faster the sensor swelled, and the faster the color change time appeared. The difference between the swelling degree and the color of each hydrocarbon was visible to the naked eye. Confirmed.
  • Figure 5 is the result of analyzing the red intensity and swelling after 5 minutes after the start of the experiment ⁇ converted to 100% when the red (R) value is 255. As shown in ⁇ 5, the lower the carbon number, the higher the swelling degree and the red value. A different color change was shown according to the carbon number. According to one embodiment of the present invention, hydrocarbons may be identified according to the carbon number.
  • Figure 6 The degree of discoloration is shown in Figure 6 so that the performance of the hydrocarbon identification sensor can be compared more easily.
  • Figure 6 (a) shows a photograph of a sensor that has passed five minutes since it was placed in a container containing hydrocarbons.
  • Fig. 6 (b) is a graph showing numerical values of red values using an Origin program. When the red (R) value is 255, it is expressed as 100%. As described above, the color transition results differently depending on the carbon number, so it can be easily confirmed by the naked eye. The lower the carbon number, the closer to red color is. The intensity of red was high.
  • the hydrocarbon identification sensor manufactured according to the following example was placed in the transparent container (4 mL vial) in a size of 1 cm x 2 cm. The result was observed after 3 minutes and the embolism was observed. The visual observation (FIG. 8) confirmed that n-octane and isooctane were transferred to different colors. N-octane without branches was closer to red and higher red intensity was also found in the original analysis (Fig. 9).
  • Cyclooctane was placed in a transparent vessel (4 mL vial) at 4 mL.
  • a hydrocarbon identification sensor prepared according to the following example was placed in the transparent vessel (4 mL vial) in a size of 1 cm X 2 cm and observed. The phenomena were analyzed by Origin program and the results are shown in FIG. [69] Branch-free n-octane swelled first, followed by swelling in the order of isooctane and cyclooctane, followed by n-octane in red intensity, followed by isooctane and cyclooctane sequence. Structural isomers resulted in different color transitions.
  • the hydrocarbon identification sensor according to the present invention enables the identification of structural isomers of hydrocarbons.
  • a hydrocarbon identification sensor manufactured according to the above example was placed in the transparent container (4 mL vial) with an H of 2 cm 2 cm, and color transition was observed.
  • Fig. 13 (a) the visual observation shows that there may be a lot of kerosene in the genuine diesel oil, and there is a lot of color transition from blue to red. In particular, 25% of kerosene is contained.
  • the case of genuine gasoline is blue, whereas if it contains 25% of kerosene, the metabolism occurs or it is very blue, and it is confirmed that the oil is mixed with gasoline.
  • the analysis by the Origin program shows the highest red intensity (unit: AU, Arbitrary Unit) in the kerosene with the lowest carbon number, and the higher the kerosene additive, the higher the red intensity. Showed a tendency Therefore, the hydrocarbon identification sensor according to the present invention can be used not only to distinguish between kerosene and diesel, Mixed with kerosene It's easy to identify.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Immunology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
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  • Optics & Photonics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biophysics (AREA)
  • Plasma & Fusion (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)

Abstract

Cette invention concerne un détecteur d'identification d'hydrocarbures, son procédé de fabrication et son application et, plus particulièrement, un détecteur d'identification d'hydrocarbures qui identifie les hydrocarbures à l'aide d'un matériau absorbant les hydrocarbures de type gonflant ou d'un matériau présentant un changement de couleur ou une fluorescence sous l'effet d'un stimulus externe, son procédé de fabrication et son application. Selon la présente invention, l'utilisation du matériau absorbant les hydrocarbures de type gonflant ou du matériau présentant un changement de couleur ou une fluorescence sous l'effet d'un stimulus externe permet d'identifier facilement les hydrocarbures à l'œil nu à tout moment et partout sans équipement onéreux et complexe. De plus, même un isomère constitutionnel difficile à identifier ayant la structure d'un hydrocarbure saturé qui défie toute identification facile peut être facilement identifié. En particulier, selon la présente invention, le kérosène et le diesel peuvent être facilement identifiés à tout moment et partout à l'œil nu, ce qui n'est pas le cas avec les procédés consistant à ajouter des agents d'identification ou les procédés d'analyse complexes rarement accessibles qui sont actuellement utilisés pour identifier le kérosène et le diesel présentant des caractéristiques de produits pétrochimiques similaires, et par conséquent le diesel contrefait qui pose un problème social peut être détecté. De plus, selon la présente invention, les hydrocarbures peuvent être facilement et simplement identifiés à l'œil nu sans équipement onéreux et complexe, et par conséquent la présente invention peut être facilement utilisée même par le grand public.
PCT/KR2013/009738 2012-11-01 2013-10-30 Détecteur d'identification d'hydrocarbures, son procédé de fabrication et application Ceased WO2014069897A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20120123129 2012-11-01
KR10-2012-0123129 2012-11-01
KR10-2013-0126202 2013-10-22
KR1020130126202A KR101516600B1 (ko) 2012-11-01 2013-10-22 탄화수소 식별 센서, 그 제조방법 및 용도

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111492241A (zh) * 2017-09-29 2020-08-04 由联邦材料研究和检测机构主席所代表的经济与能源部长所代表的德意志联邦共和国 检测土壤和水中的烃污染
WO2020252231A1 (fr) * 2019-06-14 2020-12-17 Chevron U.S.A. Inc. Systèmes et procédés d'échantillonnage d'espèces chimiques dans divers environnements

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09503059A (ja) * 1993-09-23 1997-03-25 カリフオルニア ライトウエイブ ラボラトリーズ インコーポレイテッド 炭化水素燃料検出装置
KR100779986B1 (ko) * 2006-12-30 2007-11-28 한양대학교 산학협력단 폴리다이아세틸렌 함유 초미세섬유의 제조방법
US20080193967A1 (en) * 2004-12-17 2008-08-14 Bommarito G Marco Colorimetric Sensor Constructed Of Diacetylene Materials
KR20120031035A (ko) * 2012-02-08 2012-03-29 한양대학교 산학협력단 폴리다이아세틸렌 함유 폴리머 센서 섬유를 이용한 유사휘발유 검지 방법 및 유사휘발유 검지용 폴리다이아세틸렌 함유 폴리머 센서 섬유
CN101824316B (zh) * 2009-03-05 2012-06-27 中国科学院化学研究所 一种热致变色传感材料的制备方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09503059A (ja) * 1993-09-23 1997-03-25 カリフオルニア ライトウエイブ ラボラトリーズ インコーポレイテッド 炭化水素燃料検出装置
US20080193967A1 (en) * 2004-12-17 2008-08-14 Bommarito G Marco Colorimetric Sensor Constructed Of Diacetylene Materials
KR100779986B1 (ko) * 2006-12-30 2007-11-28 한양대학교 산학협력단 폴리다이아세틸렌 함유 초미세섬유의 제조방법
CN101824316B (zh) * 2009-03-05 2012-06-27 中国科学院化学研究所 一种热致变色传感材料的制备方法
KR20120031035A (ko) * 2012-02-08 2012-03-29 한양대학교 산학협력단 폴리다이아세틸렌 함유 폴리머 센서 섬유를 이용한 유사휘발유 검지 방법 및 유사휘발유 검지용 폴리다이아세틸렌 함유 폴리머 센서 섬유

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111492241A (zh) * 2017-09-29 2020-08-04 由联邦材料研究和检测机构主席所代表的经济与能源部长所代表的德意志联邦共和国 检测土壤和水中的烃污染
US11561175B2 (en) 2017-09-29 2023-01-24 Bundesrepublik Deutschland, vertreten durch die Bundesministerin für Wirtschaft und Energie, diese vertreten durch den Präsidenten der Bundesanstalt für Materialforgchung und- Prüfung (BAM) Detection of hydrocarbon contamination in soil and water
WO2020252231A1 (fr) * 2019-06-14 2020-12-17 Chevron U.S.A. Inc. Systèmes et procédés d'échantillonnage d'espèces chimiques dans divers environnements

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