Methods for analyzing bromine compounds

Abstract

The embodiment provides a reliable method for analyzing bromine compounds. [Solution] The method for analyzing bromine compounds according to the embodiment includes the steps of: measuring the bromine concentration in a sample by X-ray fluorescence analysis; measuring the bromine concentration in a sample by mass spectrometry; and evaluating the difference between the bromine concentration in the sample measured by X-ray fluorescence analysis and the bromine concentration in the sample measured by mass spectrometry.

Description

Technical Field

[0001] Embodiments of the present invention relate to a method for analyzing bromine compounds.

Background Art

[0002] In recent years, regulations on chemical substances have become stricter. For companies manufacturing electrical and electronic equipment, etc., management of chemical substances in constituent materials used in products has become extremely important.

[0003] Some bromine compounds typified by polybrominated biphenyls that can be used in flame retardants, etc. are substances subject to regulation by the RoHS (Restriction on Hazardous Substances) directive.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0005] Embodiments of the present invention provide a reliable method for analyzing bromine compounds.

Means for Solving the Problems

[0006] The method for analyzing bromine compounds according to the embodiment includes a step of measuring the bromine concentration in a sample by X-ray fluorescence analysis, a step of measuring the bromine concentration in the sample by mass spectrometry, and a step of evaluating the difference between the bromine concentration in the sample measured by X-ray fluorescence analysis and the bromine concentration in the sample measured by mass spectrometry.

Brief Description of the Drawings

[0007] [Figure 1] Flowchart of the embodiment. [Figure 2] Chemical formula of the embodiment. [Figure 3] A flowchart of the embodiment. [Figure 4] A flowchart of the embodiment. [Figure 5] Chemical formula of the embodiment. [Modes for carrying out the invention]

[0008] A preferred embodiment will be described in detail below with reference to the drawings. In the embodiment, unless otherwise specified, the conditions are those for implementation at 25°C and atmospheric pressure (100 kPa).

[0009] In the following processes, the order of the processes can be changed unless the order is restricted.

[0010] The compounds described in the specification include optical isomers and structural isomers.

[0011] (First Embodiment) The analysis method of the first embodiment includes, as shown in the flowchart of the embodiment in Figure 1, a step of measuring the bromine concentration in the sample by X-ray fluorescence analysis (first step S01), a step of measuring the bromine concentration in the sample by mass spectrometry (second step S02), and a step of evaluating the difference between the bromine concentration in the sample measured by X-ray fluorescence analysis and the bromine concentration in the sample measured by mass spectrometry (third step S03).

[0012] The sample to be analyzed is a solid sample, such as a resin. More specifically, it is a resin containing a flame retardant.

[0013] The following explanation will use tetrabromobisphenol A (TBBPA) and polymers containing the TBBPA structure as examples of flame retardants in the sample. However, the same analysis can be performed when other bromine-containing compounds other than the TBBPA structure are included in the sample as flame retardants. Therefore, the analytical methods of the first and second embodiments are also applicable when bromine-containing compounds other than the TBBPA structure are included in the sample as flame retardants.

[0014] The first step (S01) involves measuring the bromine concentration in a sample by X-ray fluorescence analysis. This step involves weighing the sample and analyzing a predetermined mass of the sample by X-ray fluorescence analysis. The bromine concentration C1 (concentration in, for example, [mg / kg]) contained in the predetermined mass of the sample is determined by X-ray fluorescence analysis. The first step is preferably a method that conforms to screening by X-ray fluorescence analysis as specified in IEC62321-3-1.

[0015] If bromine is not detected in the sample by X-ray fluorescence analysis, this screening step indicates that the sample does not contain bromine. Therefore, if the analysis targets only bromine compounds in the sample, this screening step will determine that the sample does not contain bromine compounds, and it is not necessary to perform any other steps.

[0016] The second step (S02) involves measuring the bromine concentration in the sample by mass spectrometry. This step involves weighing the sample and performing mass spectrometry for analysis. It is preferable to heat the sample to gasify it and then analyze the gasified sample by, for example, gas chromatography-mass spectrometry (GC / MS) or ion attachment mass spectrometry (IAMS).

[0017] The sample is heated (thermally extracted) using a pyrolizer or similar device, and the resulting gas is analyzed. To suppress the decomposition of the molecular structure during heating, the heating temperature of the sample (thermally extracted temperature of the pyrolizer) is preferably between 200°C and 350°C, more preferably between 200°C and 300°C, and even more preferably between 200°C and 270°C.

[0018] For the mass spectrum obtained by performing mass spectrometry (e.g., total ion chromatogram, IA ionization mass spectrum), perform a library search related to bromine compounds to identify the mass-to-charge ratio (m / z) and its ion intensity derived from bromine compounds. Using a calibration curve, measure the concentration of the bromine compound contained in the sample, and measure the bromine concentration C2 in the sample (the concentration is, for example, [mg / kg]). It is preferable to analyze a standard sample containing TBBPA in the same manner as the sample and create a calibration curve from the obtained mass spectrum.

[0019] The bromine concentration C2 in the sample is preferably the concentration including the bromine contained in TBBPA in the sample. The chemical formula of TBBPA is shown in Chemical Formula (A) of FIG. 2. TBBPA is a substance subject to regulation under the RoHS Directive, but polymers having the TBBPA structure are not substances subject to regulation. The chemical formula of the TBBPA structure is shown in Chemical Formula (B) of FIG. 2. When the sample is thermally decomposed, a partial structure of the polymer having the TBBPA structure is also analyzed as an ion having the same mass-to-charge ratio as the ion of TBBPA. If the polymer having the TBBPA structure is determined as TBBPA and the bromine concentration is measured, there is a possibility that a commercially available product may actually be determined as non-conforming. When comparing the bromine concentration C1 measured in the first step S01 and the bromine concentration C2 measured in the second step S02 and evaluating whether the bromine concentration measured in the second step S02 exceeds the regulated amount, it is preferable to suppress the decomposition of the polymer having the TBBPA structure when thermally extracting the sample.

[0020] The bromine concentration C2 in the sample is preferably the concentration of the bromine contained in TBBPA in the sample. From the viewpoint of preventing thermal decomposition of the polymer in the sample, the thermal extraction temperature preferably satisfies the range of the thermal extraction temperature of the above pyrolyzer.

[0021] In mass spectrometry, the scanning range of the mass-to-charge ratio of the mass spectrometer is preferably 10 or more and 1000 or less. Since the mass-to-charge ratio of TBBPA is 551 in IAMS and 528.7 (or 543.7) in GC-MS, the scanning range of the mass-to-charge ratio of the mass spectrometer in mass spectrometry preferably includes the range of 500 or more and 600 or less. Since the mass-to-charge ratio of TBBPA is about 550, it can be seen that it is difficult to analyze by mass spectrometry a trimer compound having the TBBPA structure as a monomer without being decomposed during thermal extraction.

[0022] Bromine mainly has isotopes of 79Br and 81Br. For the peak of a bromine-containing compound, sub-peaks symmetric about the main peak appear. If the number of bromines in the molecule (the number of bromines in the parent ion or the number of bromines in the fragment ion) is even, sub-peaks symmetric on both sides appear centered on two main peaks. If the number of bromines in the molecule (the number of bromines in the parent ion or the number of bromines in the fragment ion) is odd, sub-peaks symmetric on both sides appear centered on one main peak. From the characteristics of the peak of the bromine compound, it is also possible to determine whether a specific peak is derived from a bromine compound.

[0023] In the step of evaluating the difference between the bromine concentration in the sample measured by X-ray fluorescence analysis and the bromine concentration in the sample measured by mass spectrometry (the third step S03), the concentration difference between the bromine concentration C1 obtained in the first step and the bromine concentration C2 obtained in the second step is evaluated, and it is evaluated whether the concentration difference is equal to or greater than a set value. This set value of the concentration difference can be arbitrarily set.

[0024] In the first step S01, the bromine concentration C1 is determined from all bromine elements in the sample. On the other hand, in the second step S02, the bromine concentration C1 is determined from ions with a mass-to-charge ratio within the scan range of the gasified sample. As a result, for example, large molecular weight polymers are excluded from the calculation of the bromine concentration C2 in the analysis of the second step S02. It is difficult to decompose the TBBPA structure in large molecular weight polymers to the extent that it can be analyzed as virtually all TBBPA ions. When these polymers are partially decomposed by the pyrolizer, ions with the same mass-to-charge ratio as TBBPA are produced, but ions with a different mass-to-charge ratio than TBBPA are also produced. Therefore, even if the bromine concentration C2 measured in the second step S02 is determined by focusing on TBBPA, it is difficult to determine whether the determined bromine concentration C2 is the concentration of TBBPA itself contained in the sample, or the concentration of bromine contained in the TBBPA structure of the polymer having a TBBPA structure contained in the sample. Furthermore, parental ions and fragment ions outside the scan range are not included in the analysis, and many bromine-containing structures such as TBBPA structures are included in the ions outside the scan range analyzed by mass spectrometry. For example, if thermal extraction is performed at high temperature, it is difficult to obtain reliable results in the screening analysis of the second step S02, which is not a precise analysis. The second step S02 is not an analysis aimed at precise analysis, but rather an analysis for comparing bromine concentrations due to differences in analytical methods.

[0025] If the difference between bromine concentration C1 and bromine concentration C2 is determined to be small (bromine concentration C1 is about the same as bromine concentration C2), or if there is no difference between bromine concentration C1 and bromine concentration C2, then the bromine concentration C1 measured in the first step S01 is considered to be largely attributable to TBBPA. If bromine concentration C2 is about the same as bromine concentration C1, then a decision can be made on whether to perform a detailed analysis depending on the values ​​of bromine concentration C1 and / or bromine concentration C2. Furthermore, if necessary, a detailed test can be performed to determine whether the TBBPA in the sample is below the regulatory limit by considering bromine concentration C1 or bromine concentration C2 (preferably bromine concentration C2) as TBBPA.

[0026] If the difference between bromine concentration C1 and bromine concentration C2 is determined to be large (larger than the difference between bromine concentration C1 and bromine concentration C2 would be determined to be small), it is likely that some bromine compounds were not analyzed by mass spectrometry in step S02.

[0027] The first embodiment allows for reliable screening of whether further measurements, such as detailed inspections, are necessary through a relatively simple operation in which the bromine concentration is measured in both the first step S01 and the second step S02.

[0028] (Second Embodiment) The analysis method of the second embodiment includes, as shown in the flowchart of the embodiment in Figure 3, a step of depolymerizing the sample (fourth step S04), a step of identifying the bromine-containing component in the depolymerized sample by mass spectrometry (fifth step S05), and a step of quantifying the identified bromine-containing component (sixth step S06). In the second embodiment, if quantification of the bromine component is not performed, the sixth step S06 can be omitted.

[0029] Steps 4 (S04) through 6 (S06) can be performed independently, or, as shown in the flowchart of the embodiment in Figure 4, the analysis method of the second embodiment can be performed after performing the analysis method of the first embodiment.

[0030] In the second embodiment, structures such as polymers containing bromine, which are difficult to analyze using the analytical method of the first embodiment, can be identified and quantitatively evaluated.

[0031] The sample to be analyzed is a solid sample, such as a resin. More specifically, it is a resin containing a flame retardant. When performing the analysis method of the second embodiment after performing the analysis method of the first embodiment, the same sample used in the first embodiment is used as the sample to be analyzed.

[0032] In the analysis method of the second embodiment, as shown in the flowchart of the embodiment in Figure 3, the step of depolymerizing the sample (fourth step S04) involves depolymerizing the sample to decompose the polymer in the sample. Depolymerization generates monomers of the polymer, reducing the degree of polymerization, or partially decomposing the polymer. Since the polymer is decomposed into monomers, etc., in the fourth step S04, the second embodiment can analyze the structure contained in the polymer and the low molecular weight (TBBPA) contained in the sample.

[0033] The method for depolymerizing the sample is, for example, to mix the sample with a solvent and then perform subcritical and / or critical treatment, with subcritical treatment being more preferable. It is preferable to measure a predetermined amount of the sample, place it in a solvent, and then perform subcritical and / or critical treatment in a pressure vessel.

[0034] The solvent used in the depolymerization process is preferably mainly an organic solvent. The amount of water contained in the solvent used in the depolymerization process is preferably 0 wt% to 3 wt%, more preferably 0 wt% to 2 wt%, and even more preferably 0 wt% to 1 wt%.

[0035] The solvent used in the depolymerization treatment preferably contains methanol, acetone, ethanol, or isopropyl alcohol, preferably contains one or more selected from the group consisting of methanol, acetone, ethanol, and isopropyl alcohol, preferably consists of one or more selected from the group consisting of methanol, acetone, ethanol, and isopropyl alcohol, and preferably is methanol, acetone, ethanol, or isopropyl alcohol.

[0036] The subcritical and critical conditions vary depending on the solvent, but for example, in subcritical treatment using methanol as the solvent, the treatment is performed at 200°C to 240°C, at 15 MPa, for 10 to 120 minutes. It is also possible to depolymerize the sample by subcritical treatment and / or critical treatment using other solvents.

[0037] Depending on the subcritical and / or critical treatment conditions, structures other than monomers may be generated. Even if structures other than monomers are generated by the depolymerization treatment, structures with the structure of bromine compounds can be identified from conditions such as the peak shape characteristic of bromine compounds. In other words, appropriate analysis can be performed from step 5 S05 onward without setting depolymerization conditions to control the position where the polymer is decomposed.

[0038] Figure 5 shows the chemical formulas (C) and (D) of brominated epoxy as examples of polymers having a TBBPA structure. Furthermore, the structure of brominated epoxy is not limited to the structure shown in Figure 5, and may include structures in which some epoxy groups are substituted with hydrogen or other elements.

[0039] When brominated epoxy (C) is depolymerized, compounds with structures cleaved at positions a and b in Figure 5, compounds with structures cleaved at positions a and c, and compounds with structures cleaved at positions c and d are produced as a result of the depolymerization.

[0040] When brominated epoxy (D) is depolymerized, compounds with structures cleaved at positions a and b in Figure 5, compounds with structures cleaved at positions a and c, compounds with structures cleaved at positions c and d, and compounds with structures cleaved at positions c and e are produced as a result of the depolymerization.

[0041] Step 5 (S05) involves identifying bromine-containing components in a depolymerized sample by mass spectrometry. This step involves heating the depolymerized sample to gasify it, performing mass spectrometry, and identifying the components of the depolymerized sample based on the information obtained from the mass spectrometry.

[0042] It is preferable to analyze the components of the depolymerized sample, which have been gasified, by gas chromatography-mass spectrometry or ion deposition mass spectrometry.

[0043] It is preferable to perform the analysis in the second step S02 and the fifth step S05 using the same method. Therefore, if gas chromatography-mass spectrometry is performed in the second step S02, it is preferable to perform gas chromatography-mass spectrometry in the fifth step S05 as well. If gas chromatography-mass spectrometry is performed in the second step S02, it is preferable to perform gas chromatography-mass spectrometry in the fifth step S05 under the same conditions as the second step S02 (conditions that are similar enough to allow quantitative evaluation by mass spectrometry in the second step S02 and mass spectrometry in the sixth step S06).

[0044] If ion-attached mass spectrometry is performed in step 2 S02, it is preferable to perform ion-attached mass spectrometry in step 5 S05 as well. If ion-attached mass spectrometry is performed in step 2 S02, it is preferable to perform ion-attached mass spectrometry in step 5 S05 under the same conditions as in step 2 S02 (conditions that are similar enough to allow quantitative evaluation in the mass spectrometry of step 2 S02 and step 6 S06).

[0045] For example, if a sample contains TBBPA and a polymer having a TBBPA structure, the depolymerized sample (in solution) will contain TBBPA and compounds having a TBBPA structure that are produced by the decomposition of the polymer having a TBBPA structure. In the second step S02, compounds outside the scan range that cannot be analyzed are decomposed in the fifth step S05, allowing for the analysis of the structures contained in the polymer.

[0046] In step 5, S05, the depolymerized sample is heated (thermally extracted) using a pyrolizer or the like, and the resulting gas is analyzed. The heating temperature of the sample (thermally extracted temperature of the pyrolizer) is preferably 200°C to 350°C, more preferably 200°C to 300°C, and even more preferably 200°C to 270°C.

[0047] Mass spectra obtained by mass spectrometry (e.g., total ion chromatogram, IA ionized mass spectrum) are searched for bromine compounds in a library to identify the mass-to-charge ratio (m / z) originating from bromine compounds. Furthermore, it is preferable to identify mass-to-charge ratios not originating from bromine compounds in order to determine the structure of the polymer.

[0048] The scan range of the mass-to-charge ratio of the mass spectrometer during mass spectrometry is preferably between 10 and 1000. Since the mass-to-charge ratio of a compound having a structure cut at positions a and b is 551, and the mass-to-charge ratio of a compound having a structure cut at positions a and c is 607, the scan range of the mass-to-charge ratio of the mass spectrometer during mass spectrometry is preferably between 500 and 700.

[0049] Bromine primarily has two isotopes, 79Br and 8Br. The peaks of bromine-containing compounds exhibit symmetrical sub-peaks around a main peak. If the number of bromine atoms in the molecule (either in the parent ion or fragment ion) is even, two main peaks are present, flanked by symmetrical sub-peaks. If the number of bromine atoms is odd, one main peak is present, flanked by symmetrical sub-peaks. The characteristics of the peaks of bromine compounds can also be used to determine whether a particular peak originates from a bromine compound.

[0050] The chemical structure of the bromine-containing component of the depolymerized sample can be identified from the mass spectrum obtained in step S05. By identifying this component, information about the structure of the polymer contained in the sample can be obtained. By identifying the bromine-containing component of the TBBPA-containing compound in the depolymerized sample, information about the structure of the polymer having a TBBPA-containing structure can be obtained.

[0051] For example, if compounds cleaved at positions a and b during depolymerization, and a compound cleaved at position b are identified in step 5 S05, it can be determined that the polymer in the sample contains a structure up to position b of chemical formula (C) in Figure 5 at one of its ends. If other end structures are not identified, the polymer with a structure like chemical formula (C) can be identified as the bromine component in the sample. Furthermore, if the other end structure is a structure cleaved at position d of chemical formula (D) in Figure 5, the polymer with a structure like chemical formula (D) can be identified as the bromine-containing component in the sample. Step 5 S05 allows for the identification of the approximate structure of the bromine-containing polymer.

[0052] By identifying the bromine-containing component in step S05, it can be determined that, for example, it includes brominated epoxy or brominated epoxy having a TBBPA structure.

[0053] The step of quantifying the identified bromine-containing components (step 6, S06) is a step of quantifying the bromine-containing components contained in the sample based on the ionic strength of the bromine-containing components identified in step 5, S05.

[0054] Using a calibration curve, the concentration of bromine compounds in the depolymerized sample is measured, and the bromine concentration C3 (concentration is, for example, [mg / kg]) of compounds having a TBBPA structure, including TBBPA itself, in the depolymerized sample is measured. It is preferable to analyze a standard sample containing TBBPA in the same manner as the sample and prepare a calibration curve from the obtained mass spectrum. If mass spectrometry in step 5 S05 is performed in the same manner as in step 2 S02, the calibration curve from step 2 S02 can be used as the calibration curve for step 6 S06.

[0055] The bromine concentration C3 of a compound having the TBBPA structure is the bromine concentration of a compound having the structure of chemical formula (B), and is, for example, the concentration of bromine in a compound with a structure cleaved at positions a and b in Figure 5.

[0056] Even if the bromine concentration C2 obtained in the second embodiment contains gases of compounds produced by the decomposition of some polymers during thermal extraction, by setting the thermal extraction temperature in the second step within a suitable range, [bromine concentration C3]-[bromine concentration C2] generally accurately represents the concentration of bromine-containing components, which are polymers, contained in the sample.

[0057] In the analytical method described in the first embodiment, if bromine-containing components other than TBBPA are unknown, the analytical method of the second embodiment can be used as a relatively simple screening method to identify bromine-containing components that have a TBBPA structure but are not TBBPA itself, and to determine their concentration. The structure of flame retardants and the like containing bromine can be reliably identified and quantified using a relatively simple screening method, even without precise analysis, and the reliability of the screening is improved by using the analytical method of the second embodiment.

[0058] The following is a technical proposal for an embodiment. Technical proposal 1 A step of measuring the bromine concentration in the sample by X-ray fluorescence analysis, A step of measuring the bromine concentration in the sample by mass spectrometry, A method for analyzing bromine compounds, comprising the step of evaluating the difference between the bromine concentration in the sample measured by the aforementioned X-ray fluorescence analysis and the bromine concentration in the sample measured by the aforementioned mass spectrometry. Technical proposal 2 The process involves depolymerizing the aforementioned sample, The process involves identifying the bromine-containing component in the depolymerized sample by mass spectrometry, A method for analyzing bromine compounds as described in Technical Proposal 1. Technical proposal 3 The mass spectrometry used to analyze the sample is pyrolysis gas chromatography, and the mass spectrometry used to analyze the depolymerized sample is pyrolysis gas chromatography, or The method for analyzing bromine compounds according to Technical Proposal 2, wherein the mass spectrometry used to analyze the sample is ion-attached mass spectrometry, and the mass spectrometry used to analyze the depolymerized sample is ion-attached mass spectrometry. Technical proposal 4 The bromine-containing component in the aforementioned sample is determined by the analytical method for bromine compounds described in Technical Proposal 2 or 3, which includes brominated epoxy. Technical proposal 5 The method for analyzing bromine compounds according to any one of Technical Proposals 1 to 4, wherein the bromine concentration in the sample measured by the mass spectrometry is the amount of bromine in tetrabromobisphenol contained in the sample. Technical plan 6 The method for analyzing bromine compounds according to any one of Technical Proposals 1 to 5, wherein the decomposition temperature of the mass spectrometry used to analyze the sample is 200°C or higher and 300°C or lower. Technical proposal 7 The depolymerization treatment involves mixing the solvent with the sample and performing subcritical treatment and / or critical treatment, as described in any one of Technical Proposals 2 to 4, for the analysis of bromine compounds. Technical proposal 8 The aforementioned solvent is methanol, acetone, ethanol, or isopropyl alcohol, as described in Technical Proposal 7 for the analysis of bromine compounds. Technical proposal 9 A method for analyzing bromine compounds according to any one of Technical Proposals 2 to 5, further comprising the step of quantifying the identified bromine-containing component. Technical proposal 10 The process involves depolymerizing the sample, The process involves identifying the bromine-containing component in the depolymerized sample by mass spectrometry, A method for analyzing bromine compounds containing [specific properties]. Technical proposal 11 A method for analyzing bromine compounds according to proposal 10, further comprising the step of quantifying the identified bromine-containing component. Technical proposal 12 The mass spectrometry used to analyze the sample is pyrolysis gas chromatography, and the mass spectrometry used to analyze the depolymerized sample is pyrolysis gas chromatography, or A method for analyzing bromine compounds according to Technical Proposal 10 or 11, wherein the mass spectrometry used to analyze the sample is ion-attached mass spectrometry, and the mass spectrometry used to analyze the depolymerized sample is ion-attached mass spectrometry. Technical proposal 13 The bromine-containing component in the aforementioned sample is analyzed using the method for analyzing bromine compounds described in any one of the technical proposals 10 to 12, which includes brominated epoxy. Technical proposal 14 The depolymerization treatment involves mixing a solvent with the sample and performing subcritical treatment and / or critical treatment, as described in any one of the technical proposals 10 to 13, for the analysis of bromine compounds. Technical proposal 15 The aforementioned solvent is methanol, acetone, ethanol, or isopropyl alcohol, as described in Technical Proposal 14, for the analysis of bromine compounds.

[0059] While several embodiments of the present invention have been described, these embodiments are presented as examples only and are not intended to limit the scope of the invention. These embodiments can be carried out in a variety of other forms, and various omissions, substitutions, and modifications can be made without departing from the spirit of the invention. These embodiments and their variations are included in the scope and spirit of the invention, as well as in the claims and their equivalents.

Claims

1. A step of measuring the bromine concentration in the sample by X-ray fluorescence analysis, A step of measuring the bromine concentration in the sample by mass spectrometry, A method for analyzing bromine compounds, comprising the step of evaluating the difference between the bromine concentration in the sample measured by the aforementioned X-ray fluorescence analysis and the bromine concentration in the sample measured by the aforementioned mass spectrometry.

2. The process involves depolymerizing the aforementioned sample, The process involves identifying the bromine-containing component in the depolymerized sample by mass spectrometry, A method for analyzing bromine compounds according to claim 1, comprising:

3. The mass spectrometry used to analyze the sample is pyrolysis gas chromatography, and the mass spectrometry used to analyze the depolymerized sample is pyrolysis gas chromatography, or The method for analyzing a bromine compound according to claim 2, wherein the mass spectrometry used to analyze the sample is ion-attached mass spectrometry, and the mass spectrometry used to analyze the depolymerized sample is ion-attached mass spectrometry.

4. The method for analyzing a bromine compound according to claim 2, wherein the bromine-containing component in the sample includes a brominated epoxy.

5. The method for analyzing a bromine compound according to claim 1, wherein the bromine concentration in the sample measured by the mass spectrometry is the amount of bromine in tetrabromobisphenol contained in the sample.

6. The method for analyzing bromine compounds according to claim 1, wherein the decomposition temperature of the mass spectrometry used to analyze the sample is 200°C or higher and 300°C or lower.

7. The method for analyzing bromine compounds according to claim 2, wherein the depolymerization treatment involves mixing a solvent with the sample and performing subcritical treatment and / or critical treatment.

8. The method for analyzing bromine compounds according to claim 7, wherein the solvent comprises methanol, acetone, ethanol, or isopropyl alcohol.

9. The method for analyzing a bromine compound according to claim 2, further comprising the step of quantifying the identified bromine-containing component.

10. The process involves depolymerizing the sample, The process involves identifying the bromine-containing component in the depolymerized sample by mass spectrometry, A method for analyzing bromine compounds containing [specific properties].

11. The method for analyzing a bromine compound according to claim 10, further comprising the step of quantifying the identified bromine-containing component.

12. The mass spectrometry used to analyze the sample is pyrolysis gas chromatography, and the mass spectrometry used to analyze the depolymerized sample is pyrolysis gas chromatography, or The method for analyzing a bromine compound according to claim 10, wherein the mass spectrometry used to analyze the sample is ion-attached mass spectrometry, and the mass spectrometry used to analyze the depolymerized sample is ion-attached mass spectrometry.

13. The method for analyzing a bromine compound according to claim 10, wherein the bromine-containing component in the sample includes a brominated epoxy.

14. The method for analyzing bromine compounds according to claim 10, wherein the depolymerization treatment involves mixing a solvent with the sample and performing subcritical treatment and / or critical treatment.

15. The method for analyzing bromine compounds according to claim 14, wherein the solvent comprises methanol, acetone, ethanol, or isopropyl alcohol.

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