WO2017135068A1 - 有機成分抽出用素子 - Google Patents
有機成分抽出用素子 Download PDFInfo
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- WO2017135068A1 WO2017135068A1 PCT/JP2017/001876 JP2017001876W WO2017135068A1 WO 2017135068 A1 WO2017135068 A1 WO 2017135068A1 JP 2017001876 W JP2017001876 W JP 2017001876W WO 2017135068 A1 WO2017135068 A1 WO 2017135068A1
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/262—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. obtained by polycondensation
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
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- B01D15/02—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor with moving adsorbents
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28002—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their physical properties
- B01J20/28009—Magnetic properties
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/34—Regenerating or reactivating
- B01J20/3433—Regenerating or reactivating of sorbents or filter aids other than those covered by B01J20/3408 - B01J20/3425
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/34—Regenerating or reactivating
- B01J20/345—Regenerating or reactivating using a particular desorbing compound or mixture
- B01J20/3475—Regenerating or reactivating using a particular desorbing compound or mixture in the liquid phase
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/34—Regenerating or reactivating
- B01J20/3483—Regenerating or reactivating by thermal treatment not covered by groups B01J20/3441 - B01J20/3475, e.g. by heating or cooling
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- G01N1/22—Devices for withdrawing samples in the gaseous state
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- G—PHYSICS
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- G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
- G01N1/40—Concentrating samples
- G01N1/4022—Concentrating samples by thermal techniques; Phase changes
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- G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
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- G01N30/14—Preparation by elimination of some components
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- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
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- G01N30/62—Detectors specially adapted therefor
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
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- B01J2220/00—Aspects relating to sorbent materials
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- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
- G01N2030/062—Preparation extracting sample from raw material
Definitions
- the present invention relates to an element for extracting an organic component and an extraction method using the element.
- the present invention also relates to an analysis method using the element.
- Solid phase microextraction and analysis of substances in fluids include active layers such as polyethylene glycol, silicon, polyimide, octadecyltrichlorosilane, polymethylvinylchlorosilane, liquid crystal polyacrylate, grafted self-constituting monolayers, and inorganic coating materials.
- active layers such as polyethylene glycol, silicon, polyimide, octadecyltrichlorosilane, polymethylvinylchlorosilane, liquid crystal polyacrylate, grafted self-constituting monolayers, and inorganic coating materials.
- Patent Document 1 describes a method using a stirring sphere covered with slag.
- Non-Patent Document 1 describes a method of measuring plant-derived volatile components with relatively high sensitivity by injecting ethyl acetate or cyclohexane into the inside of a tube made of polydimethylsiloxane.
- the present inventors can incorporate a trace amount of organic components by impregnating a specific polymer with a specific chlorine solvent, ethers, ketones, alkanes, amines, aromatic solvent, And found that the incorporated organic components can be separated.
- the present invention relates to at least one polymer selected from polyethylene glycol, silicon, polyimide, octadecyltrichlorosilane, polymethylvinylchlorosilane and polyacrylate, to dichloromethane, chloroform, diethyl ether, ethylpropyl ether, diisopropyl ether, diisopropyl ether, Propyl ether, tertiary butyl methyl ether, diethyl ketone, methyl propyl ketone, methyl isopropyl ketone, ethyl propyl ketone, methyl isobutyl ketone, pentane, isohexane, hexane, cyclohexane, heptane, isoheptane, isooctane, octane, carbon disulfide, diisopropylamine , At least one solvent selected from triether,
- the present invention is the above element, wherein the polymer is silicon and the silicon is polyorganosiloxane.
- the present invention is the above element, wherein the polyorganosiloxane is polydimethylsiloxane.
- the present invention is characterized in that the solvent contains at least one selected from the group consisting of dichloromethane, diethyl ether, diisopropyl ether, tertiary butyl methyl ether, methyl isobutyl ketone, cyclohexane, hexane and toluene. , The above element.
- the present invention is the above element, wherein a weight ratio of the polymer to the solvent is 4: 1 to 1: 4.
- the present invention is the above element, wherein the volume increase rate of the polymer after impregnating the solvent with respect to the polymer before impregnating the solvent is 120 to 400%.
- the present invention is the above element, wherein at least a part of the element is a ferromagnetic material.
- the present invention is the above element, wherein at least a part of the ferromagnetic material is coated with glass and / or plastic and further coated with the polymer.
- the present invention is the above element, wherein the plastic is polytetrafluoroethylene and / or a fluorinated hydrocarbon polymer.
- the present invention also relates to an organic component extraction method comprising: (1) a step of bringing the organic component extraction element into contact with a liquid and / or a gas containing the organic component to be extracted; and (2) the element.
- a step of taking in the organic component (3) a step of taking out the element in which the organic component has been taken in, and (4) a step of separating the organic component from the element.
- the present invention is the above method, further comprising the step of stirring the liquid and / or gas in the step (2).
- the present invention is the above method, further comprising a step of irradiating the liquid and / or gas with ultrasonic waves in the step (2).
- the present invention also relates to a method for extracting an organic component, wherein (1) the step of bringing the organic component extraction element into contact with a liquid containing the organic component to be extracted, and (2) stirring the element with a magnetic stirrer. And (3) a step of taking out the element in which the organic component has been taken in, and (4) a step of separating the organic component from the element.
- the present invention provides the step of irradiating the liquid with ultrasonic waves in the step (2), wherein the method further comprises:
- the present invention is the above method, wherein in the step (4), the organic component is separated from the element using a desorption device.
- the present invention is the method described above, wherein the desorption device includes a heating device.
- the present invention is the above method, wherein in the step (4), the organic component is separated from the element using a back extraction solvent.
- the present invention is the above method, wherein the back extraction solvent contains at least one selected from the group consisting of acetone, methyl ethyl ketone, acetonitrile, methanol, ethanol, propanol, methyl acetate, ethyl acetate, and water. .
- the present invention is a method for analyzing an organic component including a step of analyzing an organic component extracted by the above extraction method.
- the present invention is the method described above, wherein the analysis is performed using GC (gas chromatography) or LC (liquid chromatography).
- the GC detector is MS (mass analyzer), FID (hydrogen ionization detector), NPD (nitrogen phosphorus detector), ECD (electron capture detector), AED (atomic light detection). ), SCD (chemiluminescence sulfur detector), NCD (chemiluminescence nitrogen detector), FPD (flame photometric detector) and PFPD (pulsed flame photometric detector) It is.
- the present invention is the above method, wherein the LC detector is selected from the group consisting of MS, IR (differential refraction detector) and UV (ultraviolet detector).
- the present invention also includes dichloromethane, chloroform, diethyl ether, ethyl propyl ether, diisopropyl ether, dipropyl ether, tertiary butyl methyl ether, diethyl ketone, methyl propyl ketone, methyl isopropyl ketone, ethyl propyl ketone, methyl isobutyl ketone, pentane.
- solvent selected from isohexane, hexane, cyclohexane, heptane, isoheptane, isooctane, octane, carbon disulfide, diisopropylamine, triethylamine, benzene, toluene and xylene
- Polyethylene glycol, silicon, polyimide, octadecyltrichlorosilane, polymethylvinylchlorosilane and polyacrylate Is at least one polymer selected from the.
- the weight ratio of the solvent and the polymer is 4: 1 to 1: 4.
- the volume increase rate of the polymer after impregnating the solvent with respect to the polymer before impregnating the solvent is 120 to 400%.
- the above-mentioned polymer is characterized in that the solvent is selected from the group consisting of dichloromethane, diethyl ether, diisopropyl ether, tertiary butyl methyl ether, methyl isobutyl ketone, cyclohexane, hexane and toluene.
- the solvent is selected from the group consisting of dichloromethane, diethyl ether, diisopropyl ether, tertiary butyl methyl ether, methyl isobutyl ketone, cyclohexane, hexane and toluene.
- the present invention is the above polymer, wherein the polymer is silicon and the silicon is polyorganosiloxane.
- the present invention is the above polymer, wherein the polyorganosiloxane is polydimethylsiloxane.
- an element capable of extracting a trace amount of organic components can be obtained. Moreover, a trace amount organic component can be measured by GC, LC, etc. using this element.
- the organic component refers to a substance having a hydrocarbon.
- the molecular weight of the organic component to be extracted and analyzed in the present invention is not particularly limited, but is, for example, 15 daltons or more and 30000 daltons or less, preferably 15 daltons or more and 2000 daltons or less, and more preferably 15 daltons or more and 1000 daltons or less. The following are mentioned.
- polymer used in the present invention examples include polyethylene glycol, silicon, polyimide, octadecyltrichlorosilane, polymethylvinylchlorosilane, and polyacrylate.
- silicon is preferable, and polyorganosiloxane is more preferable, and polydimethylsiloxane is most preferable.
- Solvents used in the present invention include dichloromethane, chloroform, diethyl ether, ethyl propyl ether, diisopropyl ether, dipropyl ether, tertiary butyl methyl ether, diethyl ketone, methyl propyl ketone, methyl isopropyl ketone, ethyl propyl ketone, methyl isobutyl ketone.
- Pentane isohexane, hexane, cyclohexane, heptane, isoheptane, isooctane, octane, carbon disulfide, diisopropylamine, triethylamine, benzene, toluene and xylene, each of which may be used alone or in combination.
- dichloromethane, diethyl ether, diisopropyl ether, tertiary butyl methyl ether, methyl isobutyl ketone, cyclohexane, hexane, and toluene are preferable, and dichloromethane, diethyl ether, diisopropyl ether, tertiary butyl methyl ether, and cyclohexane are most preferable. preferable.
- the method for impregnating the polymer with the solvent is not particularly limited, and the organic component extraction element of the present invention can be obtained by immersing the polymer in the solvent.
- the time for impregnation depends on the thickness of the polymer, but examples thereof include 10 to 60 minutes and 10 to 120 minutes.
- the weight ratio of the solvent and the polymer may be, for example, 4: 1 to 1: 4, preferably 3: 7 to 1: 4, more preferably 1: 2 to 2: 1.
- the volume increase rate of the polymer impregnated with the solvent before impregnation with the solvent is, for example, 120 to 400%, preferably 150 to 400%, and more preferably 150 to 350%.
- the element for organic component extraction in the present invention includes the above-mentioned polymer in dichloromethane, chloroform, diethyl ether, ethyl propyl ether, diisopropyl ether, dipropyl ether, tertiary butyl methyl ether, diethyl ketone, methyl propyl ketone, methyl isopropyl ketone, ethyl.
- solvent selected from propyl ketone, methyl isobutyl ketone, pentane, isohexane, hexane, cyclohexane, heptane, isoheptane, isooctane, octane, carbon disulfide, diisopropylamine, triethylamine, benzene, toluene and xylene Can get to.
- the shape of the organic component extraction element used in the present invention is not particularly limited, and examples thereof include a spherical shape, a rod shape, an ellipsoid shape, a disk shape, a flat plate shape, and a tube shape.
- the size of the organic component extraction element used in the present invention is not particularly limited, and when it is spherical, the average particle size is, for example, 1 to 20 mm, preferably 1 to 10 mm, more preferably 1 to 5 mm. Can be mentioned.
- the diameter can be, for example, 1 to 20 mm, preferably 1 to 10 mm, more preferably 1 to 5 mm, and the length can be, for example, 10 to Examples include 100 mm, preferably 10 to 50 mm, and more preferably 10 to 25 mm.
- the major axis may be, for example, 10 to 100 mm, preferably 10 to 50 mm, more preferably 10 to 25 mm.
- the length of the minor axis include 1 to 40 mm, preferably 5 to 25 mm, more preferably 10 to 20 mm, and the aspect ratio is, for example, 1: 2 to 1:10.
- Preferred examples include 1: 2 to 1: 5, more preferably 1: 2 to 1: 3.
- the diameter can be, for example, 5 to 100 mm, preferably 10 to 50 mm, more preferably 10 to 25 mm, and the thickness can be, for example, Examples thereof include 1 to 20 mm, preferably 1 to 10 mm, and more preferably 1 to 5 mm.
- the length in the vertical direction and the horizontal direction is, for example, 5 to 100 mm, preferably 10 to 50 mm, more preferably 10 to 25 mm.
- the thickness can be, for example, 0.5 to 10 mm, preferably 1 to 10 mm, more preferably 1 to 5 mm.
- the inner diameter may be 0.5 to 9 mm, preferably 0.5 to 5 mm, more preferably 0.5 to 3 mm.
- the diameter include 2 to 12 mm, preferably 2 to 6 mm, and more preferably 2 to 3 mm.
- the thickness of the tube is, for example, 0.5 to 4 mm, preferably Examples include 0.5 to 3 mm, more preferably 0.5 to 2 mm.
- the length of the tube can be, for example, 10 to 50 mm, preferably 10 to 30 mm, more preferably 10 to 20 mm.
- organic component extraction element it can be mentioned that at least a part of the element is a ferromagnetic material.
- the ferromagnetic material is not particularly limited as long as it has a property of being attached to and detached from a magnet, and examples thereof include iron, cobalt, nickel, and gadolinium.
- the ferromagnetic material 1 can be covered with glass and / or plastic 2, and at least a part of the glass and / or plastic. Can also be coated with the polymer 3 described above.
- the plastic used here include polytetrafluoroethylene or a fluorinated hydrocarbon polymer.
- the extraction method of the present invention includes (1) a step of bringing the organic component extraction element into contact with a liquid and / or a gas containing the organic component to be extracted, and (2) a step of incorporating the organic component into the element. (3) A step of taking out the element in which the organic component has been taken in, and (4) a step of separating the organic component from the element.
- the extraction method of the present invention will be described separately for a case where an organic component is extracted from a liquid and a case where it is extracted from a gas.
- the liquid used is not particularly limited as long as it contains an organic component to be extracted.
- water, water / methanol, water / ethanol, water / acetone, Water / acetonitrile can be mentioned.
- water, water / methanol, and water / ethanol are preferable, and water / ethanol is more preferable.
- FIG. 3 shows one aspect of the present invention.
- a liquid 20 containing an organic component and a spherical organic component extraction element 10 are placed in a container 50.
- the element 10 for organic component extraction and the liquid 20 containing the organic component to extract are made to contact.
- the organic component is taken into the organic component extraction element 10.
- the standing time is not particularly limited as long as the organic component is taken into the organic component extraction element 10, and examples thereof include 5 minutes to 24 hours, 20 minutes to 4 hours, and 30 minutes to 2 hours. be able to.
- the stirring rod 40 is rotated by a motor 30 to contact the liquid 20 with the organic component extraction element 10.
- the organic component can be taken into the organic component extraction element 10 in a shorter time.
- the organic component can be taken into the organic component extraction element 10 more efficiently.
- the organic component extraction element 10 incorporating the organic component can be taken out with an automatic sampling device (not shown), tweezers, or the like.
- the organic component extraction element 10 can be extracted by removing the container 50 and filtering the liquid 20 containing the organic component extraction element 10.
- the organic component extraction element 10 can be inserted into a desorption device or the like to separate the organic components.
- the extracted organic component extraction element 10 can be placed in a back extraction solvent, and the organic component can be separated (back extracted) into the back extraction solvent.
- the solvent for back extraction is not particularly limited as long as it dissolves organic components, but for example, from the group consisting of acetone, methyl ethyl ketone, acetonitrile, methanol, ethanol, propanol, methyl acetate, ethyl acetate and water. It contains at least one selected.
- FIG. 4 shows another aspect of the present invention.
- the organic component extracting element 10 the ferromagnetic material shown in FIGS. 1 and 2 is coated with glass, and further, a part of the glass is coated with the above-described polymer.
- a plurality of containers 50 each containing the liquid 20 and the organic component extraction element 10 are used, and the liquid 20 containing different organic components can be extracted simultaneously. Further, by using the liquid 20 containing the same organic component, it is possible to increase the number of samples and improve the measurement accuracy.
- a plurality of containers 50 are arranged on a magnetic stirrer (magnetic stirrer) 80, and the organic component extraction element 10 is rotated by operating the magnetic stirrer 80. Thereby, the contact between the liquid 20 and the organic component extraction element 10 is promoted, and the organic component can be taken into the organic component extraction element 10 in a short time.
- the magnetic stirrer 80 can adjust the temperature, and can extract organic components at a constant temperature.
- the organic component extraction element 10 that has taken in the organic component can be taken out with an automatic sampling device (not shown), tweezers, or the like.
- the organic component extraction element 10 can be taken out by taking out the container 50 and filtering the liquid 20 containing the organic component extraction element 10.
- the organic component extraction element 10 can be inserted into a desorption device to separate the organic components.
- the desorption device used here is not particularly limited as long as it can separate the organic component taken into the organic component extraction element 10, for example, a device that allows a gas such as helium to flow at a constant flow rate, Examples thereof include a heating device that promotes desorption by heating.
- the extracted organic component extraction element 10 can be placed in the above-described back extraction solvent, and the organic component can be separated (back extracted) into the back extraction solvent.
- the organic component extraction element 10 is suspended in the container 55 through a lid 57 on the upper part of the container 55 by a wire-like carrier device 100.
- a solid or liquid sample 90 is placed at the bottom of the container 55, and the container 55 is sealed with a lid 57.
- the organic component evaporated from the solid or liquid sample 90 is contained in the gas 25 in the head space above the container 55, and the organic component extraction element 10 and the gas containing the organic component to be extracted are in contact with each other. Will be.
- the organic component extraction element 10 is allowed to stand in the container 55 for a certain period of time, whereby the organic component extraction element 10 is made to take in the organic component.
- the standing time is not particularly limited as long as the organic component is taken into the organic component extraction element 10, and examples thereof include 20 minutes to 2 hours, 20 minutes to 4 hours, and 5 minutes to 24 hours. be able to.
- the head space may be agitated using an agitator (not shown) such as a propeller.
- an agitator such as a propeller.
- the organic component can be taken into the organic component extraction element 10 in a shorter time than when the organic component extraction element 10 is left unattended.
- the organic component extraction element 10 can be taken out by opening the lid 57 and pulling up the support device 100. Then, the organic component extraction element 10 can be inserted into the desorption device to separate the organic components.
- the desorption device used here is not particularly limited as long as it can separate the organic component taken into the organic component extraction element 10, for example, a device that allows a gas such as helium to flow at a constant flow rate, Examples thereof include a heating device that promotes desorption by heating.
- the extracted organic component extraction element 10 can be placed in the above-described back extraction solvent, and the organic component can be separated (back extracted) into the back extraction solvent.
- the organic component separated by the above method is extruded from the desorption device 110 and introduced into the GC or LC 120.
- the GC or LC 120 is connected to a detector 130 where the organic component is measured.
- the detector 130 in the case of GC, MS (mass analyzer), FID (hydrogen ionization detector), NPD (nitrogen phosphorus detector), ECD (electron capture detector), AED (atomic light) Detector), SCD (chemiluminescence sulfur detector), NCD (chemiluminescence nitrogen detector), FPD (flame photometric detector) and PFPD (pulsed flame photometric detector).
- MS mass analyzer
- FID hydrogen ionization detector
- NPD nitrogen phosphorus detector
- ECD electron capture detector
- AED atomic light
- SCD chemiluminescence sulfur detector
- NCD chemiluminescence nitrogen detector
- FPD flame photometric detector
- PFPD pulse photometric detector
- the organic component extraction element As the organic component extraction element, the ferromagnetic material shown in FIGS. 1 and 2 is coated with glass, and a part of the glass is further coated with polydimethylsiloxane, “TWISTER-011333-001- The volume of dimethylsiloxane is 63 ⁇ L) or “TWISTER-011222-001-00 (volume of polydimethylsiloxane is 24 ⁇ L)” (Gestel, Mülheim, Germany). It was immersed for ⁇ 30 minutes to obtain an organic component extraction element.
- polydimethylsiloxane “TWISTER-011333-001- The volume of dimethylsiloxane is 63 ⁇ L) or “TWISTER-011222-001-00 (volume of polydimethylsiloxane is 24 ⁇ L)” (Gestel, Mülheim, Germany). It was immersed for ⁇ 30 minutes to obtain an organic component extraction element.
- extraction element for comparison As an extraction element for comparison, the above-mentioned “TWISTER-011333-001-00” or “TWISTER-011222-001-00” was used as it was without being treated with a solvent.
- a multi-position stirrer (04-80013-009, manufactured by Gester) was used for stirring the organic component extraction element.
- a thermal desorption apparatus TDU system (015750-090, manufactured by GESTEL) was used for introducing the organic components in the extraction element into the GC-MS.
- a quadrupole GC-MS (G3440A / G3172A, manufactured by Agilent) was used.
- Example 1 and Comparative Example 1 “TWISTER-011333-001-00” impregnated with dichloromethane was introduced into the standard sample 1 as an organic component extraction element, and stirred for 60 minutes at 800 rpm with a magnetic stirrer. At this time, the weight ratio of polydimethylsiloxane to dichloromethane was 1: 3, and the volume increase rate of polydimethylsiloxane was 280%. Thereafter, the organic component extraction element was taken out with tweezers, put into a heat desorption apparatus, and analyzed by GC-MS. The results are shown in FIG. What is indicated by the upper “A” in FIG. 7 is based on the analysis method according to the present invention, and what is indicated by “B” in the lower is the result of using the comparative element. FIG. 7 shows that the present invention can analyze a small amount of organic components with high sensitivity.
- Example 2 and Comparative Example 2 “TWISTER-011333-001-00” impregnated with toluene was put into the standard sample 1 as an organic component extraction element, and stirred for 60 minutes at 800 rpm with a magnetic stirrer. At this time, the weight ratio of polydimethylsiloxane to toluene was 1: 1.3, and the volume increase rate of polydimethylsiloxane was 210%. Thereafter, the organic component extraction element was taken out with tweezers, put into a heat desorption apparatus, and analyzed by GC-MS. The results are shown in FIG. What is indicated by the upper “A” in FIG. 8 is based on the analysis method according to the present invention, and what is indicated by “B” in the lower is the result of using the comparative element. FIG. 8 shows that the present invention can analyze a small amount of organic components with high sensitivity.
- Example 3 and Comparative Example 3 “TWISTER-011333-001-00” impregnated with dichloromethane was introduced into 5 mL of commercially available hojicha as an organic component extraction element, and stirred for 60 minutes at 800 rpm with a magnetic stirrer. At this time, the weight ratio of polydimethylsiloxane to dichloromethane was 1: 1.3, and the volume increase rate of polydimethylsiloxane was 280%. Thereafter, the organic component extraction element was taken out with tweezers, put into a heat desorption apparatus, and analyzed by GC-MS. The results are shown in FIG. The upper part “A” in FIG. 9 is based on the analysis method according to the present invention, and the lower part “B” is a result of using the comparative element. From FIG. 9, it can be seen that a trace amount of organic components can be analyzed with high sensitivity according to the present invention.
- Example 4 and Comparative Example 4 Organic components were analyzed in the same manner as in Example 3 and Comparative Example 3 except that commercially available whiskey was used. The results are shown in FIG. What is indicated by the upper “A” in FIG. 10 is based on the analysis method according to the present invention, and what is indicated by “B” in the lower is the result of using the comparative element. From FIG. 10, it can be seen that a very small amount of organic components can be analyzed with high sensitivity according to the present invention.
- Example 5 Examples 5 to 7 and Comparative Example 5
- “TWISTER-011222-001-00 volume of polydimethylsiloxane is 24 ⁇ L” impregnated with dichloromethane, diisopropyl ether or cyclohexane in 5 mL of commercially available beer was introduced as an element for extracting organic components, and a magnetic stirrer was used. , And stirred at 800 rpm for 60 minutes.
- the weight ratios of polydimethylsiloxane and dichloromethane, diisopropyl ether or cyclohexane at this time are 1: 1.2, 1: 0.86 and 1: 0.93, respectively, and the volume increase rate of polydimethylsiloxane is: They were 280%, 170% and 180%, respectively.
- the organic component extraction element was taken out with tweezers, and 500 ⁇ L of acetone was used as a back extraction solvent, and back extraction was performed for 30 minutes. 100 ⁇ L of the obtained back extract was injected into GC-MS for analysis (Examples 5 to 7).
- Example 8 to 10 and Comparative Example 6 The analysis was performed under the same conditions as in Example 5 except that TWISTER was changed to “TWISTER-011333-001-00 (polydimethylsiloxane volume 63 ⁇ L)”.
- the weight ratio of polydimethylsiloxane to dichloromethane, diisopropyl ether or cyclohexane at this time is 1: 1.3, 1: 1 and 1: 0.9, respectively, and the volume increase rate of polydimethylsiloxane is They were 280%, 200%, and 200%, respectively.
- the peak intensity of each organic component obtained in Examples 8 to 10 was normalized with the peak intensity obtained in Comparative Example 6, and the relative intensity of the organic component was compared. Table 2 shows the obtained analysis results.
- Table 3 shows the water-octanol partition coefficient (log K OW ) of each organic component extracted in Examples 5 to 10 above.
- organic components having a wide water-octanol partition coefficient can be extracted by using the organic component extraction element of the present invention.
- Example 12 and Comparative Example 13 “TWISTER-01133-001-00 (volume of polydimethylsiloxane is 63 ⁇ L)” impregnated with tertiary butyl methyl ether into 5 mL of coffee extracted with an espresso machine was added as an organic component extraction element and , And stirred at 800 rpm for 60 minutes. The weight ratio of polydimethylsiloxane and tertiary butyl methyl ether at this time was 1: 0.86, and the volume increase rate of polydimethylsiloxane was 170%. Then, the organic component extraction element was taken out with tweezers, and 500 ⁇ L of acetone was used as a back extraction solvent, and back extraction was performed for 30 minutes.
- an element capable of extracting a trace amount of organic components can be obtained. Moreover, a trace amount organic component can be measured by GC, LC, etc. using this element.
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Abstract
Description
をさらに含む上記の方法である。
本発明の抽出方法は、(1)上記の有機成分抽出用素子と、抽出する有機成分を含む液体および/または気体とを接触させる工程、(2)前記素子に、前記有機成分を取り込ませる工程、(3)有機成分が取り込まれた前記素子を取り出す工程、(4)前記素子から、有機成分を分離する工程、を含む方法である。
有機成分の標準試料1として、2-アセチルチアゾール、2,5-ジメチルピラジン、グアイアコール、クマリン、フェネチルアルコール、1-ヘキサノール、シス-3-ヘキセノール、インドール、6-メチルー5-ヘプテンー2-オン、ガンマ-ノナラクトン、フェネチルアセテート、リナロール、シトロネロール、ベータ-ダマセノンをそれぞれ50ngを精製水5mLに溶解させたものを調製した。
また、有機成分の標準試料2として、2-アセチルチアゾール、2-アセチルピロール、グアイアコール、フェネチルアルコール、1-ヘキサノール、シス-3-ヘキセノール、ベンジルアルコール、インドールをそれぞれ25ngを精製水5mLに溶解させたものを調整した。
また、市販のほうじ茶、ウイスキー、ビールおよび市販のコーヒー豆をエスプレッソマシンで抽出したコーヒーを有機成分の試料として用いた。
有機成分抽出用素子として、図1および図2に示した強磁性体をガラスで被覆し、さらにそのガラスの1部をポリジメチルシロキサンで被覆したものである「TWISTER-011333-001-00(ポリジメチルシロキサンの体積が63μL)」または「TWISTER-011222-001-00(ポリジメチルシロキサンの体積が24μL)」(ゲステル社製、ドイツ国、ミュールハイム)を適宜用い、これらを溶媒1~10mLに10~30分間浸漬して、有機成分抽出用素子を得た。
比較用の抽出素子として、上記の「TWISTER-011333-001-00」または「TWISTER-011222-001-00」を溶媒で処理せずにそのまま用いた。
<使用機器>
有機成分抽出用素子の撹拌には、マルチポジションスターラー(04-80013-009、ゲステル社製)を用いた。抽出用素子中の有機成分のGC-MSへの導入には、加熱脱着装置TDUシステム(015750-090、ゲステル社製)を用いた。GC-MSは四重極型GC-MS(G3440A/G3172A、アジレント社製)を用いた。
<分析条件>
GC-MSへの導入は、加熱脱着の場合、ヘリウム(50mL/min)をキャリアガスとして180℃で行った。また、溶媒脱着(逆抽出)の場合は、アセトン500μLで30分間逆抽出を行い、逆抽出液100μLを注入した。GCカラムにはDB-Wax(アジレント社製)を用い、初期温度40℃で3分間保持後、10℃/minで240℃までの昇温を行い、そのまま10分間保持し、質量範囲(m/z)として29-300のスキャン測定を行った。
標準試料1中に、ジクロロメタンを含浸させた「TWISTER-011333-001-00」を有機成分抽出用素子として投入し、磁気撹拌装置により、800rpmで60分間撹拌した。この時のポリジメチルシロキサンとジクロロメタンの重量比は、1:3であり、ポリジメチルシロキサンの体積増加率は、280%であった。その後、有機成分抽出用素子をピンセットで取り出し、加熱脱着装置に投入し、GC-MSにより分析を行った。結果を図7に示す。図7の上段「A」で示されるものが、本発明による分析方法によるものであり、下段の「B」で示されるものが、比較用素子を用いた結果である。
図7より、本願発明により、微量の有機成分を感度よく分析できることがわかる。
標準試料1中に、トルエンを含浸させた「TWISTER-011333-001-00」を有機成分抽出用素子として投入し、磁気撹拌装置により、800rpmで60分間撹拌した。この時のポリジメチルシロキサンとトルエンの重量比は、1:1.3であり、ポリジメチルシロキサンの体積増加率は、210%であった。その後、有機成分抽出用素子をピンセットで取り出し、加熱脱着装置に投入し、GC-MSにより分析を行った。結果を図8に示す。図8の上段「A」で示されるものが、本発明による分析方法によるものであり、下段の「B」で示されるものが、比較用素子を用いた結果である。
図8より、本願発明により、微量の有機成分を感度よく分析できることがわかる。
市販のほうじ茶5mLに、ジクロロメタンを含浸させた「TWISTER-011333-001-00」を有機成分抽出用素子として投入し、磁気撹拌装置により、800rpmで60分間撹拌した。この時のポリジメチルシロキサンとジクロロメタンの重量比は、1:1.3であり、ポリジメチルシロキサンの体積増加率は、280%であった。その後、有機成分抽出用素子をピンセットで取り出し、加熱脱着装置に投入し、GC-MSにより分析を行った。結果を図9に示す。図9の上段「A」で示されるものが、本発明による分析方法によるものであり、下段の「B」で示されるものが、比較用素子を用いた結果である。
図9より、本願発明により、微量の有機成分を感度よく分析できることがわかる。
市販のウイスキーを用いた以外は、実施例3および比較例3と同様にして、有機成分を分析した。結果を図10に示す。図10の上段「A」で示されるものが、本発明による分析方法によるものであり、下段の「B」で示されるものが、比較用素子を用いた結果である。
図10より、本願発明により、微量の有機成分を感度よく分析できることがわかる。
市販のビール5mLに、それぞれ、ジクロロメタン、ジイソプロピルエーテル又はシクロヘキサンを含浸させた「TWISTER-011222-001-00(ポリジメチルシロキサンの体積が24μL)」を有機成分抽出用素子として投入し、磁気撹拌装置により、800rpmで60分間撹拌した。この時のポリジメチルシロキサンと、ジクロロメタン、ジイソプロピルエーテル又はシクロヘキサンの重量比は、それぞれ、1:1.2、1:0.86および1:0.93であり、ポリジメチルシロキサンの体積増加率は、それぞれ、280%、170%および180%であった。その後、有機成分抽出用素子をピンセットで取り出し、逆抽出用溶媒として500μLのアセトンを用い、30分間逆抽出を行った。得られた逆抽出液100μLをGC-MSに注入して分析を行った(実施例5~7)。
また、溶媒で含浸させていない「TWISTER-011222-001-00」を用いた場合について比較のための分析を行った(比較例5)。
ここで、比較例5で得られたピーク強度で、実施例5~7で得られた各有機成分のピーク強度を規格化し、有機成分の相対強度の比較を示す。得られた分析結果を表1に示す。
TWISTERを、「TWISTER-011333-001-00(ポリジメチルシロキサンの体積が63μL)」に替えたほかは、実施例5と同一の条件で分析を行った。なお、この時のポリジメチルシロキサンと、ジクロロメタン、ジイソプロピルエーテル又はシクロヘキサンの重量比は、それぞれ、1:1.3、1:1および1:0.9であり、ポリジメチルシロキサンの体積増加率は、それぞれ、280%、200%、および200%であった。
ここで、比較例6で得られたピーク強度で、実施例8~10で得られた各有機成分のピーク強度を規格化し、有機成分の相対強度の比較を示した。得られた分析結果を表2に示す。
標準試料2中に、ジエチルエーテル、テトラヒドロフラン、酢酸エチル、酢酸メチル、アセトニトリル、およびアセトンを含浸させた「TWISTER-011333-001-00」を有機成分抽出用素子として投入し、磁気撹拌装置により、800rpmで60分間撹拌した。この時のポリジメチルシロキサンと、ジエチルエーテル、テトラヒドロフラン、酢酸エチル、酢酸メチル、アセトニトリル、またはアセトンの重量比は、それぞれ、1:1、1:1.2、1:0.78、1:0.43、1:0.23、1:0.24であり、ポリジメチルシロキサンの体積増加率は、それぞれ、200%、240%、200%、150%、120%、120%であった。その後、有機成分抽出用素子をピンセットで取り出し、加熱脱着装置に投入し、GC-MSにより分析を行った。
また、溶媒で含浸させていない「TWISTER-011333-001-00」を用いた場合について比較のための分析を行った(比較例7)。
ここで、比較例7で得られたピーク強度で、実施例11および比較例8~12で得られた各有機成分のピーク強度を規格化し、有機成分の相対強度の比較を示した。得られた分析結果を表4に示した。
エスプレッソマシンで抽出したコーヒー5mLに、ターシャリーブチルメチルエーテルを含浸させた「TWISTER-011333-001-00(ポリジメチルシロキサンの体積が63μL)」を有機成分抽出用素子として投入し、磁気撹拌装置により、800rpmで60分間撹拌した。この時のポリジメチルシロキサンと、ターシャリーブチルメチルエーテルの重量比は、1:0.86であり、ポリジメチルシロキサンの体積増加率は、170%であった。その後、有機成分抽出用素子をピンセットで取り出し、逆抽出用溶媒として500μLのアセトンを用い、30分間逆抽出を行った。得られた逆抽出液100μLをGC-MSに注入して分析を行った。
また、溶媒で含浸させていない「TWISTER-011333-001-00」を用いた場合について比較のための分析を行った(比較例)。
結果を図11に示す。図11の上段「A」で示されるものが、本発明による分析方法によるものであり、下段の「B」で示されるものが、比較用素子を用いた結果である。
図11より、本願発明により、微量の有機成分を感度よく分析できることがわかる。
ここで、比較例13で得られたピーク強度で、実施例12で得られた各有機成分のピーク強度を規格化し、有機成分の相対強度の比較を示す。得られた分析結果を表5に示す。
2 ガラスおよび/またはプラスチック
3 ポリマー
10 有機成分抽出用素子
20 液体
25 気体
30 モータ
40 撹拌棒
50 容器
55 容器
57 蓋
60 超音波発生装置
70 水
80 磁気撹拌装置
90 固体または液体試料
100 担持器具
110 脱離装置
120 GCまたはLC
130 検出器
Claims (28)
- ポリエチレングリコール、シリコン、ポリイミド、オクタデシルトリクロロシラン、ポリメチルビニルクロロシランおよびポリアクリレートから選択される少なくとも1種のポリマーに、ジクロロメタン、クロロホルム、ジエチルエーテル、エチルプロピルエーテル、ジイソプロピルエーテル、ジプロピルエーテル、ターシャリーブチルメチルエーテル、ジエチルケトン、メチルプロピルケトン、メチルイソプロピルケトン、エチルプロピルケトン、メチルイソブチルケトン、ペンタン、イソヘキサン、ヘキサン、シクロヘキサン、ヘプタン、イソヘプタン、イソオクタン、オクタン、二硫化炭素、ジイソプロピルアミン、トリエチルアミン、ベンゼン、トルエンおよびキシレンから選択される少なくとも1種の溶媒が含浸している前記ポリマーを有することを特徴とする、有機成分抽出用素子。
- 前記ポリマーがシリコンであり、前記シリコンが、ポリオルガノシロキサンであることを特徴とする、請求項1に記載の素子。
- 前記ポリオルガノシロキサンが、ポリジメチルシロキサンであることを特徴とする、請求項2に記載の素子。
- 前記溶媒が、ジクロロメタン、ジエチルエーテル、ジイソプロピルエーテル、ターシャリーブチルメチルエーテル、メチルイソブチルケトン、シクロヘキサン、ヘキサンおよびトルエンからなるから選択される少なくとも1種を含むことを特徴とする、請求項1~3のいずれかに記載の素子。
- 前記ポリマーと前記溶媒の重量比が、4:1~1:4である、請求項1~4のいずれかに記載の素子。
- 前記溶媒を含浸させる前の前記ポリマーに対する溶媒を含浸させた後のポリマーの体積増加率が、120~400%である、請求項1~5のいずれかに記載の素子。
- 前記素子の少なくとも1部が強磁性体であることを特徴とする、請求項1~6のいずれかに記載の素子。
- 前記強磁性体の少なくとも1部が、ガラスおよび/またはプラスチックで被覆された上に、さらに前記ポリマーで被覆されていることを特徴とする、請求項7に記載の素子。
- 前記プラスチックが、ポリテトラフルオロエチレンおよび/またはフッ化処理された炭化水素ポリマーである、請求項8に記載の素子。
- 有機成分の抽出方法であって、
(1)請求項1~9のいずれかに記載の有機成分抽出用素子と、抽出する有機成分を含む液体および/または気体とを接触させる工程、
(2)前記素子に、前記有機成分を取り込ませる工程、
(3)前記有機成分が取り込まれた前記素子を取り出す工程、
(4)前記素子から、前記有機成分を分離する工程、
を含む方法。 - 前記工程(2)において、前記液体および/または気体を撹拌する工程、
をさらに含む、請求項10に記載の方法。 - 前記工程(2)において、前記液体および/または気体に超音波を照射する工程、をさらに含む、請求項10または11に記載の方法。
- 有機成分の抽出方法であって、
(1)請求項7~9のいずれかに記載の素子と、抽出する有機成分を含む液体とを接触させる工程、
(2)前記素子を磁気攪拌機により撹拌して、前記素子に前記有機成分を取り込ませる工程、
(3)前記有機成分が取り込まれた前記素子を取り出す工程、
(4)前記素子から、有機成分を分離する工程、
を含む方法。 - 前記工程(2)において、前記液体に超音波を照射する工程、
をさらに含む、請求項13に記載の方法。 - 前記工程(4)において、前記素子から脱離装置を用いて前記有機成分を分離することを特徴とする、請求項10~14のいずれかに記載の方法。
- 前記脱離装置が、加熱装置を備えることを特徴とする、請求項15に記載の方法。
- 前記工程(4)において、前記素子から逆抽出用溶媒を用いて前記有機成分を分離することを特徴とする、請求項10~14のいずれかに記載の方法。
- 前記逆抽出用溶媒が、アセトン、メチルエチルケトン、アセトニトリル、メタノール、エタノール、プロパノール、酢酸メチル、酢酸エチルおよび水からなる群より選択される少なくとも1種を含む、請求項17に記載の方法。
- 請求項10~18に記載の抽出方法により抽出された有機成分を分析する工程、
含む有機成分の分析方法。 - GC(ガスクロマトグラフィー)またはLC(液体クロマトグラフィー)を用いて分析を行うことを特徴とする、請求項19に記載の方法。
- 前記GCの検出器が、MS(質量分析器)、FID(水素イオン化検出器)、NPD(窒素リン検出器)、ECD(電子捕獲型検出器)、AED(原子光検出器)、FPD(炎光光度検出器)、化学発光硫黄検出器(SCD)、化学発光窒素検出器(NCD)およびPFPD(パルスド炎光光度検出器)からなる群より選択される、請求項20に記載の方法。
- 前記LCの検出器が、MS、IR(示差屈折検出器)およびUV(紫外線検出器)からなる群より選択される、請求項20に記載の方法。
- ジクロロメタン、クロロホルム、ジエチルエーテル、エチルプロピルエーテル、ジイソプロピルエーテル、ジプロピルエーテル、ターシャリーブチルメチルエーテル、ジエチルケトン、メチルプロピルケトン、メチルイソプロピルケトン、エチルプロピルケトン、メチルイソブチルケトン、ペンタン、イソヘキサン、ヘキサン、シクロヘキサン、ヘプタン、イソヘプタン、イソオクタン、オクタン、二硫化炭素、ジイソプロピルアミン、トリエチルアミン、ベンゼン、トルエンおよびキシレンから選択される少なくとも1種の溶媒が含浸しているポリマーであって、前記ポリマーが、ポリエチレングリコール、シリコン、ポリイミド、オクタデシルトリクロロシラン、ポリメチルビニルクロロシランおよびポリアクリレートから選択される少なくとも1種のポリマー。
- 前記溶媒と前記ポリマーの重量比が、4:1~1:4である、請求項23に記載のポリマー。
- 前記溶媒を含浸させる前の前記ポリマーに対する前記溶媒を含浸させた後の前記ポリマーの体積増加率が、120~400%である、請求項23または24に記載のポリマー。
- 前記溶媒が、ジクロロメタン、ジエチルエーテル、ジイソプロピルエーテル、ターシャリーブチルメチルエーテル、メチルイソブチルケトン、シクロヘキサン、ヘキサンおよびトルエンからなる群から選択される少なくとも1種であることを特徴とする、請求項23~25のいずれかに記載のポリマー。
- 前記ポリマーがシリコンであり、前記シリコンが、ポリオルガノシロキサンであることを特徴とする、請求項23~26に記載のポリマー。
- 前記ポリオルガノシロキサンが、ポリジメチルシロキサンであることを特徴とする、請求項27に記載のポリマー。
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