JPH09329589A - Method for extraction and analysis of organic low-molecular weight compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a method wherein organic low molecular weight compound contained in a specimen can be easily heated and extracted in a short time with high reproducibility, the extracted organic low molecular weight compound can be preferably used for various kinds of analysis such as element analysis, infrared spectrochemical analysis and gas chromatography as well as analysis by mass spectrometer, and analysis of high precision is easily enabled. SOLUTION: A high frequency electromagnetic induction heating equipment is filled with specimen X like vinyl chloride resin. A specimen cell 1 is covered with electromagnetic induction heat generating metal body which generates heat up to a temperature lower than the decomposition temperature of the specimen X, e.g. ferromagnetic metal body whose Curie temperature is 220 deg.C. The specimen cell 1 is subjected to high frequency electromagnetic induction heating up to the Curie temperature. Organic low molecular weight compound such as additive and unreacted compound is evaporated and extracted from the specimen X. The extracted organic low molecular weight compound is used as the specimen for various kinds of analysis such as GC (gas chromatography), and GC-MG (gas chromatography mass spectrometer).

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to an organic low molecular weight compound constituting a material such as a polymer, paper, toner and thermal paper, and an organic low molecular weight compound such as an additive added to the material. The present invention relates to a method for extracting and a method for analyzing an organic low molecular weight compound using the organic low molecular weight compound obtained by this method as an analysis sample.

[0002]

2. Description of the Related Art Conventionally, in order to extract organic low molecular weight compounds such as additives contained in raw materials and synthetic raw materials remaining in raw materials, Soxhlet extraction method and raw materials using a solvent suitable for the substance to be extracted Is dissolved in a good solvent, then a poor solvent is added to precipitate the raw material, and the raw material is filtered, then the reprecipitation method such as concentrating the filtrate, dry distillation is performed, and the dry distillation method is extracted as a dry distillate. is there.

[0003]

However, in the case of Soxhlet extraction, it is necessary to find a solvent that is suitable for the substance to be extracted, and in the reprecipitation method, it is necessary to dissolve the raw materials and perform filtration separation. However, depending on the material, many are insoluble in solvents, and therefore cannot be used in many cases.
Further, the Soxhlet extraction method and the reprecipitation method are disadvantageous in that the operation takes time. The carbonization method uses an oil bath, an aluminum block heater, an alcohol lamp, a gas burner, etc. as a heat source, but it takes a considerable amount of time to raise the temperature, and it takes time to cool the heating source to room temperature after completion, gas. The heating temperature cannot be controlled with a burner or an alcohol lamp, and when using an oil bath, there are drawbacks such as possible contamination of the sample. As a result, there is a problem that analysis takes time.

[0004] For example, at the Japan Society for Analytical Chemistry, Shinho Polymer Handbook, p551 (1995) Kinokuniya Bookstore, regarding the solubility of typical polymers in the reprecipitation method, a combination of a good solvent and a poor solvent was used. However, these combinations cannot be properly used unless the type of polymer is known, and there is a drawback that they cannot be used until the polymer has been identified. Also,
In the above-mentioned Polymer Analysis Handbook p533, in the closed tube test (similar to dry distillation), the bottom of the glass tube containing the sample is heated with an electric heater or a gas burner.
With this heating method, it is difficult to maintain the heating temperature with good reproducibility. Further, since the temperature is considerably high, thermal decomposition products and side reaction products are likely to occur.

[0005]

Means for Solving the Problems As a result of earnest studies on a method for solving the above problems, the present inventor filled a sample cell with a sample (X), preferably a hermetically sealed sample, and filled it with a sample by high frequency electromagnetic induction heating. An electromagnetic induction heating metal body that heats up to a temperature lower than the decomposition temperature of (X), for example, a ferromagnetic metal body having a Curie temperature lower than the decomposition temperature of the sample (X), and the high frequency electromagnetic wave is applied to the electromagnetic induction heating metal body. If an extraction method such as induction heating is adopted, the sample can be easily heated in a short time to extract organic low molecular weight compounds such as additives and unreacted compounds contained in the sample, and the heating method is electromagnetic induction. High-frequency electromagnetic induction heating using an exothermic metal body enables easy and reproducible heat extraction,
The obtained extract can be preferably used for various analyzes such as mass spectrometer, gas chromatography, elemental analysis and infrared spectroscopic analysis, and can be easily and accurately analyzed. As an electromagnetic induction exothermic metal body, it is 50 to 400. It has been found that the use of a metal body having a relatively low Curie temperature of ° C can easily prevent decomposition of the sample (X) and breakage of the sample cell during high frequency electromagnetic induction heating, and completed the present invention.

That is, according to the present invention, (1) the high frequency electromagnetic induction heating apparatus is filled with the sample (X) and covered with an electromagnetic induction heating metal body which generates heat to a temperature lower than the decomposition temperature of the sample (X). A method for extracting an organic low molecular weight compound, comprising: disposing a sample cell, which is heated to a Curie temperature by high-frequency electromagnetic induction to volatilize and extract the organic low molecular weight compound (Y) from the sample (X), (2) The extraction method according to the above (1), wherein the electromagnetic induction heating metal body is a ferromagnetic metal body having a Curie temperature lower than the decomposition temperature of the sample (X), (3) Curie of the electromagnetic induction heating metal body. The extraction method according to (1) or (2) above, wherein the temperature is 50 to 400 ° C.

(4) The sample (X) is hermetically filled in a sample cell, and this is heated by high frequency electromagnetic induction to a Curie temperature to extract the organic low molecular weight compound (Y) from the sample (X) into the sample (X) inside the sample cell. ) The extraction method according to (1), (2) or (3) above, which comprises volatilizing into the non-filled space and then condensing.
(5) The sample (X) is hermetically filled in a sample cell having a capacity twice or more the volume of the sample (X), and the sample (X) is subjected to high-frequency electromagnetic induction heating to Curie temperature and organic low molecular weight compound (Y) is volatilized into the non-filled space of the sample (X) inside the sample cell, and then condensed, and then the condensed organic low molecular weight compound (Y) is dissolved in an organic solvent and collected (1), ( 2) or the extraction method described in (3),

(6) The high frequency electromagnetic induction heating time is from 1 to
Extraction method according to any one of (1) to (5) above, which is for 60 minutes, (7) A high-frequency electromagnetic induction heating device in which a sample cell covered with an electromagnetic induction heating metal body is placed in a protection cell. The extraction method according to any one of (1) to (6) above, (8) the extraction method according to (7), wherein the sample cell and the protection cell are glass cells.

(9) Any one of the above (1) to (8)
An organic low molecular weight compound (Y) obtained by the extraction method as described in 1 above is used as an analysis sample, (10) The above (1) to
Gas chromatography (GC) or gas chromatography-mass spectrometer (GC) using the organic low molecular weight compound (Y) or its organic solvent solution obtained by the extraction method according to any one of (8) as an analysis sample. -M
The analysis method according to (9) above, which is performed by S).

(11) An organic low molecular weight compound (Y) obtained by the extraction method described in any one of (1) to (8) above or an organic solvent solution thereof is added to the organic low molecular weight compound (Y). (12) The method for analyzing an organic low molecular weight compound, which comprises using a modifying agent (Z) for a part or all of the above and reacting it, and then using as a sample for analysis.
The organic low-molecular weight compound (Y) obtained by the extraction method according to any one of (8) or an organic solvent solution thereof, and a modifier (Z) for part or all of the organic low-molecular weight compound (Y) Is used as an analysis sample and analyzed by gas chromatography (GC) or gas chromatography-mass spectrometer (GC-MS). (Analysis method according to 11, and (13) Modification agent (Z ) Is a silylating agent (11) or (12)
The analysis method described above is provided.

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION The sample (X) used in the present invention may be of any type, but is preferably powder or granular. Examples thereof include polymer compounds, plastics, fibers, films, thermal papers, rubbers, paints, composite materials, additives, toners and woods. Among them, volatile and thermal stability are high,
It is preferable that an organic low-molecular weight compound that can be dissolved in a solvent is extracted, because analysis by GC, GC-MS and the like is easy.

Among these samples (X), the thermosetting resin is effective in extracting and analyzing the residual unreacted raw material by the method of the present invention. That is, even if the Soxhlet extraction method is used, it is difficult to select a solvent and it often takes time and labor to concentrate the extraction solvent. However, according to the method of the present invention, the organic low molecular weight compound (Y) can be easily obtained in a short time. It can be extracted and then immediately directly injected into GC or GC-MS.

The electromagnetic induction heat-generating metal body used in the present invention is a metal body which is irradiated with a high frequency wave and generates a high frequency electromagnetic induction heat to a temperature lower than the decomposition temperature of the sample (X) and can cover the sample cell. It is sufficient that the organic low molecular weight compound (Y) in the sample (X) is lower than the decomposition temperature of the sample (X) because the temperature can be raised quickly and the extraction can be completed stably in a short time. Thickness of 0.01 to 0.5 m made of a ferromagnetic metal body having an extractable Curie temperature
A metal foil (foil) or metal plate of about m is appropriately selected and used.

The above-mentioned ferromagnetic metal body has a ferromagnetic metal and rapidly heats up to the Curie temperature (magnetic transition point) by high frequency electromagnetic induction heating, and thereafter continues high frequency electromagnetic induction heating to generate the Curie temperature. From a metal body containing one or more ferromagnetic metals such as nickel, iron and cobalt, or alloys of these with other metals such as copper, chromium, zinc, manganese and aluminum Examples of the metal body include pyrofoil (Curie temperature 160 to 1040 ° C.) manufactured by Nippon Analytical Industry Co., Ltd. and the like. The Curie temperature of these ferromagnetic metal bodies varies greatly depending on the kind and composition of the metal, and for example, the Curie temperature of an alloy of nickel and copper is about 150 to 200 ° C., while the Curie temperature of nickel is 358 ° C. and that of nickel and iron. The alloy has a Curie temperature of about 500 to 650 ° C, and iron has a high Curie temperature of 770 ° C. In the present invention, in order to prevent the sample cell from being broken due to the decomposition of the sample and the increase in the vapor pressure of the sample due to the high temperature heating during the high frequency electromagnetic induction heating, the Curie temperature is 50 to 400 among these ferromagnetic metal bodies.
It is preferable that a ferromagnetic metal body having a Curie temperature of 100 to 350 ° C. is appropriately selected and used. Examples of the ferromagnetic metal body that can be used here include Pyrofoils F160 and F17 manufactured by Nippon Analytical Industry Co., Ltd.
0, F220, F235, F255, F280, F35
8 and the like.

The sample cell used in the present invention includes a safe material which can be filled with the sample (X), and is usually made of glass. The shape and size of the high-frequency electromagnetic induction heating device are different depending on the size and ability of the high-frequency electromagnetic induction heating device, the amount of the sample (X) used, and the like, but are not limited thereto.
When used for analysis such as MS, the outer diameter is usually 1.5-5 m
m, length 20 to 150 mm, the capacity is usually 30 to 15
The volume is 00 μl, preferably 50 to 400 μl, and it is preferable to select and use one having a volume that is at least twice the volume of the sample (X) to be subjected to extraction.

The present invention will be described more specifically below with reference to the drawings showing an example of the extraction method of the present invention. FIG. 1 is a conceptual diagram showing an example of an extraction method of an organic low molecular weight compound of the present invention, (1) is a sample cell, (2) is a foil made of an electromagnetic induction heating metal body, and (3) is a protection cell. , (4) is a high-frequency heating coil in the high-frequency electromagnetic induction heating device (the high-frequency electromagnetic induction heating device is not shown in its entirety), and (X) is a sample for extracting the organic low molecular weight compound (Y).

First, the sample cell (1) having one opening is filled with the sample (X). Preferably, the opening of the sample cell (1) is then sealed and sealed with a burner or the like as shown in FIG. When the sample cell (1) is closed and used, the organic low molecular weight compound (Y) extracted from the sample (X) is volatilized by electromagnetic induction heating, and the non-filled space of the sample (X) inside the sample cell (1). There is an advantage that the organic low molecular weight compound (Y) collects easily (in the upper part of the sample cell in FIG. 1) and is easily collected. The case where a sample cell in which the sample (X) is sealed and filled is used will be described below. The filling amount of the sample (X) is not particularly limited, but is 3 to 50% of the sample cell capacity.
Is preferred.

Next, the sample cell (1) is covered with a foil (2) made of an electromagnetic induction heating metal body, but the entire sample cell (1) is necessarily covered with a foil (2) made of an electromagnetic induction heating metal body. No need. The foil (2) may be appropriately covered so that the sample (X) is heated to extract the organic low molecular weight compound (Y). By changing the area and thickness of the foil (2), the sample (X) The extraction conditions, such as the heating rate and the heating temperature, can be changed appropriately. The sample cell (1) covered with the foil (2) made of an electromagnetic induction heat-generating metal body may be used as it is, but it is put in a protection cell (3) made of glass or the like for protection and high-frequency electromagnetic induction heating. It is preferable.

Further, a foil (2) is formed from an electromagnetic induction heating metal body.
The sample cell (1) covered with is left as it is, or as shown in FIG. 1, the sample cell (1) is put in the protection cell (3) and placed in the high frequency heating coil (4), and then energized to apply high frequency. Then, the foil (2) made of an electromagnetic induction heat-generating metal body is made to generate heat, and the sample (X) is heated by continuing energization to volatilize the organic low molecular weight compound (Y) in the sample (X) to make the sample ( X) Collect in the unfilled space.

The high frequency electromagnetic induction heating device used here is not particularly limited as long as it can heat the electromagnetic induction heating metal body by high frequency irradiation. The high frequency electromagnetic induction heating time by high frequency irradiation is not particularly limited, but is usually 1 to 60 minutes, preferably 30 minutes.

After the heating is completed, the sample cell (1) is taken out, and the unfilled space portion of the sample (X) is filled with water, if necessary.
The organic low molecular weight compound (Y) is condensed on the inner wall of the non-filled space by cooling with ice water or other refrigerant. Then
The sample cell (1) is cut at the boundary of the non-filled space between the sample (X) and the sample (X), and if necessary, the extracted organic low molecular weight compound (Y) is dissolved in a solvent to prepare a sample solution, which is prepared in advance. Analyze with set analytical equipment such as GC or GC-MS.

The solvent used for dissolving the organic low molecular weight compound (Y) is preferably one in which the extracted organic low molecular weight compound (Y) is well dissolved, and usually acetone, acetonitrile, n-hexane, acetic acid. Ethyl, alcohol, etc. are used. The amount of the solvent used varies depending on the amount and type of the organic low molecular weight compound (Y) extracted, but is usually 1
0-100 μl is sufficient.

When the extracted organic low molecular weight compound (Y) has a reactive functional group such as a hydroxyl group, an amino group, a carboxyl group and a thiol group, it was dissolved in a solvent if necessary. Then, the reactive functional group modifier (Z)
It is preferable that the compound is reacted with the organic low molecular weight compound (Y) as a derivative to enhance volatility and thermal stability, and then subjected to analysis such as GC and GC-MS.

The solvent used here is a modifier (Z).
Any substance that does not react with, for example, acetonitrile, toluene, tetrahydrofuran, hexane, chloroform, pyridine, ethyl acetate and the like can be mentioned.

The modifier (Z) used here is reacted with the reactive functional group of the extracted organic low molecular weight compound having the reactive functional group, preferably within 15 minutes at room temperature. Any reactive functional group can be modified, and examples include silylating agents, alkylating agents, and acylating agents. Usually, a silylating agent or an alkylating agent is used, but a silylating agent is preferable because modification of hydroxyl group, amino group, carboxyl group, thiol group and the like is easy.

Examples of the silylating agent include N, O-
Bis (trimethylsilyl) acetamide (BSA),
N, O-bis (trimethylsilyl) trifluoroacetamide (BSTFA), N-trimethylsilylacetamide (TMSA), N-methyl-N-trimethylsilylacetamide (MTMSA), N-methyl-N-trimethylsilyltrifluoroacetamide (MSTFA),
N-methyl-N- (tert-butyldimethylsilyl) -trifluoroacetamide (MTBSTFA),
N-trimethylsilylimidazole (TMSI), N-
(Trimethylsilyl) dimethylamine (TMS-DM
A), N- (trimethylsilyl) diethylamine (TM
S-DEA), tetramethyldisilazane (TMDS),
Examples thereof include dimethyldichlorosilane (DMCS), trimethylchlorosilane (TMCS), tertiary butyldimethylchlorosilane (tert-BDMCS), and a mixed pyridine solution (HT) of hexamethylenedisilazane (HMDS) and trimethylchlorosilane.

Examples of the alkylating agent include N,
N-dimethylformamide dimethyl acetal (DMF
-DMA), N, N-dimethylformamide diethyl acetal (DMF-DEA), N, N-dimethylformamide di-n-propyl acetal (DMF-DNP)
A), N, N-dimethylformamide di-n-butylacetal (DMF-DNBA), tetramethylammonium hydroxide (TMAH), trimethylaniline hydroxide (TMAnH), hexafluoroisopropanol (H
FIP), hydrochloric acid-methanol mixture, hydrochloric acid-n-butanol mixture, boron trifluoride-methanol mixture, boron trifluoride-n-propanol mixture, boron trifluoride-iso-propanol mixture, trifluoride Examples thereof include a boron chloride-n-butanol mixed solution.

Further, as the acylating agent, for example, N-methylbistrifluoroacetamide (MBTFA), bistrifluoroacetamide (BTFA), heptafluorobutyrylimidazole (HFBI), heptafluoropropionic anhydride (PFPA), heptafluoroanhydride. Butyric acid (PFBA), trifluoroacetic anhydride (TFA)
A), acetic anhydride "in pyridine solution (AA-Py) and the like.

[0029]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto.

Example 1 A commercial commercial vinyl chloride resin rod was used as a sample (X). 70 mg of a vinyl chloride resin rod for work was put into a sample cell in which one of a glass tube having an outer diameter of 5 mm, an inner diameter of 3.5 mm and a length of 60 mm was sealed, and the opening was heated by a burner to seal the tube. A metal foil made of a ferromagnetic metal having a Curie temperature of 235 ° C. (a pyrofoil F235 manufactured by Nippon Analytical Industry Co., Ltd., thickness 0.9 mm, length 23 mm, width 9 m)
m), then 10 mm outer diameter, 8 mm inner diameter, 1 length
After being placed in a protection cell made of a 20 mm test tubular glass, it was placed in a high-frequency electromagnetic induction heating device, and the high-frequency electromagnetic heating device was energized for 5 minutes to heat the metal foil to 235 ° C. by high-frequency electromagnetic induction heating, A condensate of an organic low molecular weight compound added to a working vinyl chloride resin rod was obtained in the unfilled space portion of the sample (X).

After completion of energization, the sample cell is taken out, the unfilled space portion of the sample (X) is cooled with ice water, and then the sample (X) is unsealed at the boundary between the filled portion and the unfilled space portion to form the unfilled space portion. 20 μl of the solvent acetone was injected to dissolve the condensate. The following GC-MS is used as an analytical sample.
It was injected into GC-MS set to the measurement conditions and analyzed.

GC-MS measurement conditions (GC measurement conditions) Column: Length 1 m × inner diameter 3 mm Carrier (chromosolve W) having a particle size of 60-80 mesh was impregnated with 2% by weight of liquid phase (Silicone OV-17). Carrier gas: Helium gas (flow rate 30 ml / mi
n) Column temperature: After holding at 50 ° C for 1 minute, 10 ° C / mi
Temperature rises to 270 ° C at a rate of n Injection temperature: 250 ° C (MS measurement conditions) Ion source temperature: 310 ° C Electron impact (EI): voltage 70 eV, current 60 μA

FIG. 2 is a total ion chromatogram (hereinafter abbreviated as “TIC”), and FIG. 3 is a mass spectrum by electron impact (EI) (hereinafter abbreviated as “EI mass spectrum”). One large peak was observed in the TIC of FIG. 2, and it was found from the EI mass spectrum of FIG. 3 that the dibutyl phthalate had a molecular weight of 278 and was represented by the following structural formula (1).

[0034]

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Example 2 As the sample (X), 69 mg of a commercially available household polymer wrap film (vinyl chloride resin) was used in place of the commercially available work-use vinyl chloride resin rod, and the energization time to the high frequency electromagnetic induction heating device was 10 times. After obtaining the condensate of the organic low molecular weight compound from the polymer wrap film in the same manner as in Example 1 except that the time was changed, 20 μl of acetone was used to dissolve the condensate, which was used as an analytical sample in the same manner as in Example 1. GC-M
Analysis by S was performed. FIG. 4 shows the TIC, and (A), (B) and (C) of FIG. 5 show peaks (A),
It is an EI mass spectrum of (B) and (C).

From the EI mass spectrum (A), it was found that the compound of peak (A) was nonylphenol having a molecular weight of 220 and represented by the following structural formula (2). This EI mass spectrum (A) is a standard EI mass spectrum (EPA / NIH Ma) of nonylphenol shown in FIG.
It was in agreement with the standard EI mass spectrum (s) described in ss Spectral Data Base.

[0037]

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For the compounds of peaks (B) and (C), the standard EI of the compounds whose EI mass spectra (B) and (C) are represented by the following structural formulas (3) and (4) shown in FIG. Mass spectra (b) and (c) are almost the same or similar, and the characteristic fragment ions in the same part of these spectra are represented by the following ion structural formulas (5) to (8). It can be presumed to be the compounds represented by the formulas (9) and (10).

[0039]

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[0040]

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[0041]

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This is because in the EI mass spectrum (B) of peak (B) in FIG. 4, the ion structural formula (5) is present due to the presence of m / z 213, and the ionic structural formula (5) is due to the presence of m / z 129. (8) are considered respectively. From these, the compound of peak (B) in FIG. 4 can be estimated as the above structural formula (9), and further, in the EI mass spectrum (C) of peak (C) in FIG. / Z213 is present, the ionic structural formula (5) is represented by m / z241, and the ionic structural formula (6) is represented by m / z259.
The presence of ## STR1 ## suggests an ionic structure (7), which is consistent with the fact that the compound of peak (C) in FIG.

Example 3 As the sample (X), 134 mg of SBR rubber cushion material was used instead of the commercially available vinyl chloride resin rod for work, and further, as a metal foil made of a ferromagnetic metal, a pyrofoil with a Curie temperature of 220 ° C. was used instead of the pyrofoil F235. F220
(Thickness 0.9 mm, length 23 mm, width 9 mm) was used, and the SBR rubber cushion material was changed to an organic low molecular weight compound in the same manner as in Example 1 except that the energization time to the high frequency electromagnetic induction heating device was changed to 15 minutes. After obtaining the condensate of Example 1, the condensate was dissolved with 20 μl of acetone, and this was used as an analysis sample and analyzed by GC-MS in the same manner as in Example 1. Figure 7
Is the TIC, and (D) and (E) of FIG. 8 are EI mass spectra of peaks (D) and (E) in FIG.

From the EI mass spectrum (D), the compound of peak (D) has the following structural formula (11) with a molecular weight of 181.
Was found to be N-cyclohexyl-cyclohexanamine. This EI mass spectrum (D)
Was in agreement with the standard EI mass spectrum (d) of N-cyclohexyl-cyclohexanamine shown in FIG.

From the EI mass spectrum (E), the compound of peak (E) has the following structural formula (12) having a molecular weight of 220.
Was found to be 2,6-ditertiarybutyl-4-methyl-phenol. This EI mass spectrum (E) was in agreement with the standard EI mass spectrum (e) of 2,6-ditertiarybutyl-4-methyl-phenol shown in FIG.

[0046]

[Chemical 6]

Example 4 As the sample (X), 60 mg of polystyrene pellets was used instead of the commercially available vinyl chloride resin rod for work, and further, as a metal foil made of a ferromagnetic metal body, instead of the pyrofoil F235, a Pyrofoil F280 (Curie temperature 280 ° C.) was used. Condensate of organic low molecular weight compound from polystyrene pellets in the same manner as in Example 1 except that the thickness was 0.9 mm, the length was 23 mm, the width was 9 mm, and the energization time to the high frequency electromagnetic induction heating device was changed to 10 minutes. Then, the condensate was dissolved in 20 μl of acetonitrile to prepare an acetonitrile solution. N, O-bis (trimethylsilyl) acetamide (BS
A, trimethylsilylating agent) (3 μl) was added for trimethylsilylation, and this was used as an analytical sample and allowed to stand at room temperature for 10 minutes, and then analyzed by GC-MS in the same manner as in Example 1.
FIG. 10 shows the TIC, which is shown in FIGS. 11 to 12 (F) to (K).
Is the EI mass spectrum of peaks (F) to (K) in FIG.

From the EI mass spectrum (F), the compound of peak (F) has the following structural formula (13) with a molecular weight of 194.
It was found that the compound was a trimethylsilylated derivative of benzoic acid represented by (TMS in the structural formula represents "trimethylsilyl group". The same applies hereinafter). This EI mass spectrum (F) was in agreement with the standard EI mass spectrum (f) of the trimethylsilylated derivative of benzoic acid shown in FIG.

From the EI mass spectrum (G), the compound of peak (G) has the following structural formula (14) with a molecular weight of 206.
It was found to be a trimethylsilylated derivative of anol represented by. The compound of peak (H) was found from its EI mass spectrum (H) to be a dimer of styrene having a molecular weight of 208 and represented by the following structural formula (15).

From the EI mass spectrum (I), the compound of peak (I) has the following structural formula (16) with a molecular weight of 328.
It was found to be a trimethylsilylated derivative of palmitic acid. This EI mass spectrum (I)
Was in agreement with the standard EI mass spectrum (i) of the trimethylsilylated derivative of palmitic acid shown in FIG.

From the EI mass spectrum (J), the compound of peak (J) has the following structural formula (17) with a molecular weight of 356.
It was found to be a trimethylsilylated derivative of stearic acid. This EI mass spectrum (J)
Was in agreement with the standard EI mass spectrum (j) of the trimethylsilylated derivative of stearic acid shown in FIG.

From the EI mass spectrum (K), the compound of peak (K) has the following structural formula (18) with a molecular weight of 312.
It was found to be a trimer of styrene represented by.

[0053]

[Chemical 7]

[0054]

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[0055]

INDUSTRIAL APPLICABILITY According to the present invention, organic low molecular weight compounds such as additives and unreacted compounds contained in sample (X) can be easily and reproducibly heated and extracted in an extremely short time. Moreover,
The extracted organic low molecular weight compound can be preferably used not only for analysis by mass spectrometer but also for various analyzes such as elemental analysis, infrared spectroscopic analysis, gas chromatography, etc., and analysis with high accuracy can be easily performed.

[Brief description of drawings]

FIG. 1 is a conceptual diagram showing an example of a method for extracting an organic low molecular weight compound of the present invention.

2 is a total ion chromatogram (TIC) of a solution containing an organic low molecular weight compound extracted in Example 1. FIG.

FIG. 3 is an electron impact mass spectrum (EI mass spectrum) of the main component of the solution containing the organic low molecular weight compound extracted in Example 1.

FIG. 4 is a TIC of a solution containing an organic low molecular weight compound extracted in Example 2.

FIG. 5 is an EI mass spectrum of the main component of the solution containing the organic low molecular weight compound extracted in Example 2.

FIG. 6 shows nonylphenol, another standard EI mass spectrum (EPA / NIHMass Spectra).
1 is a standard EI mass spectrum described in 1 Data Base).

FIG. 7 is a TIC of a solution containing an organic low molecular weight compound extracted in Example 3.

FIG. 8 is an EI mass spectrum of the main component of the solution containing the organic low molecular weight compound extracted in Example 3.

FIG. 9 shows N-cyclohexyl-cyclohexanamine and 2,6-ditertiarybutyl-4-methyl-
It is a standard EI mass spectrum of phenol.

FIG. 10 is a TIC of a solution containing a compound obtained by trimethylsilylating the organic low molecular weight compound extracted in Example 4.

11 is an EI mass spectrum of the main component of a solution containing a compound obtained by trimethylsilylating the organic low molecular weight compound extracted in Example 4. FIG.

FIG. 12 is an EI mass spectrum of the main component of a solution containing a compound obtained by trimethylsilylating the organic low molecular weight compound extracted in Example 4.

FIG. 13 is a standard EI mass spectrum of a trimethylsilylated derivative of benzoic acid, a trimethylsilylated derivative of palmitic acid, and a trimethylsilylated derivative of stearic acid.

[Explanation of symbols]

 1 sample cell 2 foil made of an electromagnetic induction heating metal body 3 protection cell 4 high frequency heating coil X sample

Claims (13)

[Claims] 1. A sample cell filled with a sample (X) and covered with an electromagnetic induction heating metal body that generates heat to a temperature lower than the decomposition temperature of the sample (X) is arranged in a high frequency electromagnetic induction heating device. A method for extracting an organic low molecular weight compound, which comprises heating the sample to a Curie temperature by high frequency electromagnetic induction to volatilize and extract the organic low molecular weight compound (Y) from the sample (X). 2. The extraction method according to claim 1, wherein the electromagnetic induction exothermic metal body is a ferromagnetic metal body having a Curie temperature lower than the decomposition temperature of the sample (X). 3. The extraction method according to claim 1, wherein the Curie temperature of the electromagnetic induction heating metal body is 50 to 400 ° C. 4. A sample cell is hermetically filled with a sample (X), and this is heated to a Curie temperature by high frequency electromagnetic induction to obtain an organic low molecular weight compound (Y) from the sample (X) inside the sample cell (X). The extraction method according to claim 1, 2 or 3, wherein the extraction is performed by volatilizing in the non-filled space and then condensing. 5. A sample cell having a capacity of at least twice the volume of the sample (X) is hermetically filled with the sample (X), and this is subjected to high-frequency electromagnetic induction heating up to the Curie temperature, and the sample (X) is treated with an organic solvent. Molecular weight compound (Y) is sample (X) in sample cell
4. The extraction method according to claim 1, 2 or 3, wherein the organic low molecular weight compound (Y) thus condensed is volatilized in the non-filled space, and then the condensed organic low molecular weight compound (Y) is dissolved and collected in an organic solvent. 6. The extraction method according to claim 1, wherein the high frequency electromagnetic induction heating time is 1 to 60 minutes. 7. The extraction method according to claim 1, wherein a sample cell covered with an electromagnetic induction heating metal body is placed in a protection cell and placed in a high-frequency electromagnetic induction heating device. 8. The extraction method according to claim 7, wherein the sample cell and the protection cell are glass cells. 9. A method for analyzing an organic low molecular weight compound, which comprises using the organic low molecular weight compound (Y) obtained by the extraction method according to any one of claims 1 to 8 as an analysis sample. 10. A gas chromatography (GC) or a gas chromatograph using an organic low molecular weight compound (Y) or an organic solvent solution thereof obtained by the extraction method according to claim 1 as an analysis sample. The analysis method according to claim 9, wherein the analysis is performed by a graphography-mass spectrometer (GC-MS). 11. An organic low molecular weight compound (Y) obtained by the extraction method according to claim 1 or a solution of the organic low molecular weight compound (Y) in a part of the organic low molecular weight compound (Y) or A method for analyzing an organic low molecular weight compound, which comprises using a modifier (Z) for all of them and reacting them, and then using the resulting mixture as an analysis sample. 12. An organic low molecular weight compound (Y) obtained by the extraction method according to any one of claims 1 to 8 or a solution of the organic low molecular weight compound (Y) in a part of the organic low molecular weight compound (Y) or A gas chromatograph (GC) or a gas chromatograph-mass spectrometer (G) was used as an analytical sample by adding a modifier (Z) to all and reacting.
The analysis method according to claim 11, wherein the analysis is performed by C-MS). 13. The analysis method according to claim 11, wherein the modifying agent (Z) is a silylating agent.