3,5,5-trimethylhexanoic acid composition, method for suppressing odor in 3,5,5-trimethylhexanoic acid composition, and method for producing a low-odor 3,5,5-trimethylhexanoic acid composition.

Abstract

The 3,5,5-trimethylhexanoic acid composition, etc., contains 3,5,5-trimethylhexanoic acid and formic acid as a trace component, wherein the concentration of formic acid determined by liquid chromatography analysis is greater than 0 ppm by mass and 25 ppm by mass or less.

Description

Technical Field

[0001] The present invention relates to a 3,5,5-trimethylhexanoic acid composition, a method for suppressing odor in the 3,5,5-trimethylhexanoic acid composition, and a method for producing a low-odor 3,5,5-trimethylhexanoic acid composition.

Background Art

[0002] It is known that 3,5,5-trimethylhexanoic acid can be synthesized by oxidation of 3,5,5-trimethylhexanal, which is a precursor aldehyde (for example, Patent Document 1). 3,5,5-trimethylhexanoic acid is used as a raw material for cosmetic raw materials, refrigerant oil raw materials, metal processing oils, etc. Cosmetics, refrigerant oils, and metal processing oils are required to have low odor for the raw materials because, due to the characteristics of their uses, there is a possibility of being exposed, although it is slight.

[0003] So far, a 3,5,5-trimethylhexanoic acid composition with low reproductive toxicity has been known (Patent Document 2), but in the 3,5,5-trimethylhexanoic acid composition, odor has still been an issue.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0005] The present invention aims to solve the aforementioned problems in the conventional era and achieve the following objectives. Specifically, the present invention aims to provide a 3,5,5-trimethylhexanoic acid composition with suppressed odor, a method for suppressing odor in a 3,5,5-trimethylhexanoic acid composition, and a method for producing a low-odor 3,5,5-trimethylhexanoic acid composition. [Means for solving the problem]

[0006] As a result of diligent research conducted by the present inventors to achieve the above objective, it has been found that a 3,5,5-trimethylhexanoic acid composition with suppressed odor, a method for suppressing odor in a 3,5,5-trimethylhexanoic acid composition, and a method for producing a low-odor 3,5,5-trimethylhexanoic acid composition can be provided.

[0007] The present invention is based on the aforementioned findings by the inventors, and the means for solving the aforementioned problems are as follows: <1> It contains 3,5,5-trimethylhexanoic acid and formic acid as a trace component. This 3,5,5-trimethylhexanoic acid composition is characterized in that the concentration of formic acid, as measured by liquid chromatography under the measurement conditions described later, is greater than 0 ppm by mass and less than or equal to 25 ppm by mass. <2> The aforementioned <1> This is a cosmetic ingredient composition characterized by containing the 3,5,5-trimethylhexanoic acid composition described above. <3> The aforementioned <1> This is a raw material composition for refrigeration oil, characterized by containing the 3,5,5-trimethylhexanoic acid composition described above. <4> This is a method for suppressing odor in a 3,5,5-trimethylhexanoic acid composition, characterized by including a formic acid concentration adjustment step in which the formic acid concentration as a trace component is adjusted to greater than 0 ppm by mass and less than or equal to 25 ppm by mass by liquid chromatography analysis measured under the measurement conditions described below. <5> A method for producing a low-odor 3,5,5-trimethylhexanoic acid composition, characterized by including a formic acid concentration adjustment step in which the formic acid concentration as a trace component is adjusted to greater than 0 ppm by mass and less than or equal to 25 ppm by mass by liquid chromatography analysis measured under the measurement conditions described below. <6> The aforementioned <1> A method for producing a cosmetic composition using the 3,5,5-trimethylhexanoic acid composition described above, characterized by comprising a step of derivatizing the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition. <7> The aforementioned <1> A method for producing a refrigeration oil composition using the 3,5,5-trimethylhexanoic acid composition described in [reference], characterized by comprising a step of derivatizing the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition. [Effects of the Invention]

[0008] According to the present invention, it is possible to provide a 3,5,5-trimethylhexanoic acid composition with suppressed odor, a method for suppressing odor in a 3,5,5-trimethylhexanoic acid composition, and a method for producing a low-odor 3,5,5-trimethylhexanoic acid composition. [Brief explanation of the drawing]

[0009] [Figure 1] This is an example of an apparatus used in the odor-smearing gas chromatography / mass spectrometry of the present invention. [Modes for carrying out the invention]

[0010] (3,5,5-trimethylhexanoic acid composition) The 3,5,5-trimethylhexanoic acid composition comprises 3,5,5-trimethylhexanoic acid and formic acid as a trace component, and may further contain other components.

[0011] -3,5,5-Trimethylhexanoic acid- The 3,5,5-trimethylhexanoic acid has a molecular formula of C9H 18 O 2、 and is represented by the structural formula (CH3)3CCH2CH(CH3)CH2COOH, and is a compound with a molecular weight of 158.24. The 3,5,5-trimethylhexanoic acid may also be referred to as isononanoic acid.

[0012] In the 3,5,5-trimethylhexanoic acid composition, the concentration (purity) of the 3,5,5-trimethylhexanoic acid is not particularly limited and can be appropriately selected according to the purpose, but is preferably 95.0% or more, more preferably 97.0% or more, still more preferably 98.5% or more, and particularly preferably 99.0% or more.

[0013] The timing for measuring the concentration of the 3,5,5-trimethylhexanoic acid is not particularly limited and can be appropriately selected according to the purpose.

[0014] The concentration of the 3,5,5-trimethylhexanoic acid is measured by gas chromatography analysis under the following measurement conditions and calculated as the area ratio (%) of the peak of the 3,5,5-trimethylhexanoic acid to the area of all peaks.

[0015] For the gas chromatography apparatus, for example, "Gas Chromatography 2010 Plus" manufactured by Shimadzu Corporation can be used. For the gas chromatography column, for example, "DB-FFAP" (part number: 122-3232) manufactured by Agilent Technologies can be used. The measurement conditions for gas chromatography are as follows. (Measurement conditions) Analysis column: A column with a length of 30 m × an inner diameter of 0.25 mm, the stationary phase of which contains a highly polar polyethylene glycol with a film thickness of 0.25 μm Temperature programming: Hold at 80°C for 1 minute, then increase the temperature at a rate of 10°C / min, and hold for 26 minutes when reaching 210°C Sample introduction temperature: 250 °C Carrier gas: Nitrogen Column gas flow rate: 1.0 mL / min Detector and detection temperature: Flame ionization detector (FID), 250 °C Control mode: Constant linear velocity mode Split ratio: 50:1 Sample injection conditions: 0.5 μL

[0016] -Formic acid- The formic acid is a compound represented by the molecular formula CH2O2, the structural formula HCOOH, and having a molecular weight of 46.03. The formic acid may also be referred to as methanoic acid.

[0017] In the 3,5,5-trimethylhexanoic acid composition, the lower limit of the concentration of the formic acid is not particularly limited as long as it is more than 0 mass ppm, and can be appropriately selected according to the purpose. From the viewpoint of suppressing odor, 0.10 mass ppm or more is preferable, 1.0 mass ppm or more is more preferable, 4.0 mass ppm or more is further preferable, 5.0 mass ppm or more is even more preferable, 8.0 mass ppm or more is particularly preferable, and 10 mass ppm or more is most preferable. In the 3,5,5-trimethylhexanoic acid composition, the upper limit of the concentration of the formic acid is not particularly limited as long as it is 25 mass ppm or less, and can be appropriately selected according to the purpose. From the viewpoint of suppressing odor, 22 mass ppm or less is preferable, 20 mass ppm or less is more preferable, 18 mass ppm or less is further preferable, and 15 mass ppm or less is particularly preferable. Note that a numerical range having as the lower limit any of the numerical values shown as the lower limit and as the upper limit any of the numerical values shown as the upper limit can be set as a preferable range. Among these, 0.10 ppm by mass or more and 22 ppm by mass is preferred, 1.0 ppm by mass or more and 22 ppm by mass is more preferred, 4.0 ppm by mass or more and 20 ppm by mass is even more preferred, 5.0 ppm by mass or more and 18 ppm by mass is even more preferred, 8.0 ppm by mass or more and 18 ppm by mass is particularly preferred, and 10 ppm by mass or more and 15 ppm by mass is most preferred. It is believed that by setting the concentration of formic acid in the 3,5,5-trimethylhexanoic acid composition within the above range, 4,4-dimethyl-2-pentanone is generated within a suitable range during storage, exhibiting a masking effect against other odor components and improving the odor.

[0018] There are no particular restrictions on the timing of measuring the concentration of formic acid, and it can be appropriately selected depending on the purpose. The concentration of formic acid is measured by liquid chromatography analysis, as described in the section <Measurement of Formic Acid Concentration> below.

[0019] -Other ingredients- The aforementioned other components are not particularly limited and can be appropriately selected depending on the purpose. Examples include 4,4-dimethyl-2-pentanone as a trace component.

[0020] --4,4-dimethyl-2-pentanone-- The aforementioned 4,4-dimethyl-2-pentanone has the molecular formula C7H 14 O is a compound represented by the structural formula (CH3)3CCH2COCH3 and has a molecular weight of 114.19. The aforementioned 4,4-dimethyl-2-pentanone may also be referred to as methyl neopentyl ketone, 4,4-dimethyl-2-pentanone, neopentyl methyl ketone, 4,4-dimethylpentan-2-one, or methyl 2,2-dimethylpropyl ketone.

[0021] The concentration of 4,4-dimethyl-2-pentanone in the 3,5,5-trimethylhexanoic acid composition is measured as a deuterated toluene equivalent concentration by the method described later in <olfactory gas chromatography / mass spectrometry>.

[0022] There are no particular restrictions on the lower limit of the deuterium toluene equivalent concentration of 4,4-dimethyl-2-pentanone, and it can be appropriately selected depending on the purpose, but it is preferably 5.0 ppb or more by volume, more preferably 10 ppb or more by volume, even more preferably 15 ppb or more by volume, even more preferably 20 ppb or more by volume, particularly preferably 21 ppb or more by volume, and most preferably 25 ppb or more by volume. There are no particular restrictions on the upper limit of the deuterium toluene equivalent concentration of 4,4-dimethyl-2-pentanone, and it can be appropriately selected depending on the purpose, but it is preferably 50 ppb by volume or less, more preferably 45 ppb by volume or less, even more preferably 40 ppb by volume or less, even more preferably 35 ppb by volume or less, particularly preferably 30 ppb by volume or less, and most preferably 28 ppb by volume or less. Furthermore, a range of values ​​where one of the values ​​indicated as the lower limit and one of the values ​​indicated as the upper limit are used as the preferred range. Among these, a range of 5.0 ppb to 50 ppb is preferred, 10 ppb to 45 ppb is more preferred, 15 ppb to 40 ppb is even more preferred, 20 ppb to 35 ppb is even more preferred, 21 ppb to 30 ppb is particularly preferred, and 25 ppb to 28 ppb is most preferred.

[0023] There are no particular restrictions on the timing of measuring the deuterium-to-toluene equivalent concentration of 4,4-dimethyl-2-pentanone, and it can be appropriately selected depending on the purpose. For example, it may be done immediately after the production of the 3,5,5-trimethylhexanoic acid composition, or it may be done after heating the 3,5,5-trimethylhexanoic acid composition at 80°C in an air atmosphere for one week.

[0024] In the 3,5,5-trimethylhexanoic acid composition according to this embodiment, "heated at 80°C for one week in an air atmosphere" refers to accelerated conditions for creating a state in which the 3,5,5-trimethylhexanoic acid composition has been stored for a long period of time.

[0025] -Method for producing 3,5,5-trimethylhexanoic acid composition- There are no particular limitations on the method for producing the 3,5,5-trimethylhexanoic acid composition, and it can be appropriately selected depending on the purpose, but it can be produced by a method including a synthesis step, a purification step, and a formic acid concentration adjustment step.

[0026] --Synthesis process-- The aforementioned synthesis step is a step for synthesizing crude 3,5,5-trimethylhexanoic acid. The aforementioned crude 3,5,5-trimethylhexanoic acid refers to 3,5,5-trimethylhexanoic acid before purification.

[0027] There are no particular limitations on the method for synthesizing the crude 3,5,5-trimethylhexanoic acid, and it can be appropriately selected depending on the purpose. For example, the method described in International Publication No. 2022 / 118917 can be used. Specifically, for example, 3,5,5-trimethylhexanal can be synthesized by hydroformylation of diisobutylene and oxogas, and crude 3,5,5-trimethylhexanoic acid can be synthesized by subsequent oxidation.

[0028] --Purification process-- The purification step is a step of purifying the crude 3,5,5-trimethylhexanoic acid. The aforementioned purification process may include a distillation process, etc.

[0029] --- Distillation Process --- The aforementioned distillation process is a process for removing components with a boiling point lower than that of 3,5,5-trimethylhexanoic acid (120°C / 13 mmHg) (low-boiling point components) and components with a boiling point higher than that of 3,5,5-trimethylhexanoic acid (high-boiling point components). Specifically, for example, the crude 3,5,5-trimethylhexanoic acid can be placed in a three-necked flask equipped with a reflux condenser and a thermometer and subjected to vacuum distillation at 25 kPa. The fraction obtained by collecting the fraction at which the top temperature of the column is between 180 and 200°C can be obtained. The aforementioned purified 3,5,5-trimethylhexanoic acid refers to 3,5,5-trimethylhexanoic acid after purification.

[0030] --Formic acid concentration adjustment process-- The formic acid concentration adjustment step is a step of adjusting the formic acid concentration as a trace component in a 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid, to greater than 0 ppm by mass and less than or equal to 25 ppm by mass, as measured by liquid chromatography analysis under the measurement conditions described later.

[0031] There are no particular restrictions on the method for adjusting the formic acid concentration in the formic acid concentration adjustment step, and it can be appropriately selected depending on the purpose, but examples include adding formic acid. There are no particular restrictions on the method of adding the formic acid, and it can be appropriately selected depending on the purpose.

[0032] <Formic acid concentration measurement> The formic acid concentration is measured by liquid chromatography analysis of the 3,5,5-trimethylhexanoic acid composition under the following conditions: Using a reagent with known formic acid purity, the formic acid concentration is analyzed in the range of 5 ppm to 120 ppm by mass. A calibration curve is created using the results converted to formic acid purity, and quantitative analysis is performed.

[0033] - Liquid chromatography analysis - For example, a liquid chromatography apparatus such as the "LC-2050C-3D" manufactured by Shimadzu Corporation can be used. For liquid chromatography, for example, a "TSKgel ODS-100V 5μm (4.6mm inner diameter, 25cm length)" manufactured by Tosoh Corporation can be used as a column.

[0034] The measurement conditions for liquid chromatography analysis are as follows: Column: Packed column for reverse-phase chromatography, 25 cm in length and 4.6 mm in inner diameter. Stationary phase of the analytical column (gel particles packed into the column): Particle size 5 μm, pore size 100 Å, non-surface area 450 m², with octadecyl groups introduced as a monolayer on the surface. 2 Silica gel particles with a pore volume of 1.10 mL / g and a carbon content of 15%. Mobile phase: Mobile phase A: 0.1% by mass aqueous phosphoric acid solution, Mobile phase B: Acetonitrile Gradient conditions: The ratio of mobile phase A to mobile phase B is changed as follows depending on the analysis time. 0-15 minutes Mobile phase A100% 15-25 minutes: Linearly change from mobile phase A (100%) to mobile phase B (100%). 25-30 minutes Mobile phase B100% 30-40 minutes: Linearly change from mobile phase B (100%) to mobile phase A (100%). 40-60 minutes Mobile phase A100% Mobile phase flow rate: 1.0mL / min Column oven temperature: 40℃ Detector: UV detector Usage wavelength: 210nm Sample injection method: Autosampler used Sample injection volume: 10.0 μL Sample dilution: Use without dilution. Calibration curve: Analyze three or more samples with formic acid concentrations ranging from 1 ppm to 40 ppm by mass, and create a calibration curve using the peak area of ​​the formic acid component.

[0035] <Odor-detecting gas chromatography / mass spectrometry> The aforementioned odor-sniffing gas chromatography / mass spectrometry is performed using the apparatus shown in the schematic diagram of the apparatus in Figure 1. This apparatus consists of a concentration device that aspirates the gas phase of the sample filled in a container, removes H2O, N2, O2, and CO2, and concentrates the remaining volatile organic compounds (sample vapor from the gas phase of the sample being measured); a gas chromatograph that separates the concentrated volatile organic compounds (vapor) using a capillary column; an odor-sniffing system that allows the separated components to be directly smelled; and a mass spectrometer that qualitatively and quantitatively analyzes the separated components.

[0036] -concentrated- The 3,5,5-trimethylhexanoic acid composition is a liquid at atmospheric pressure (0.1 MPa) and room temperature (25°C). 5.0 g of the 3,5,5-trimethylhexanoic acid composition is placed in a 500 mL resealable container and allowed to stand at 30°C for at least 20 minutes. Then, 200 mL of the gas phase is drawn out and introduced into an automatic concentrator. The automatic concentration apparatus used comprises a device for aspirating the gas phase of a container in which an organic compound is placed; Module 1, which is a ceramic-coated trap without an adsorbent for removing moisture from the gas phase; Module 2, which is a ceramic-coated trap filled with weakly polar porous polymer beads based on 2,6-diphenyl-p-phenylene oxide as an adsorbent for adsorbing the gas phase from which moisture has been removed and for removing nitrogen, oxygen, carbon dioxide, and methane; and Module 3, which is a rapid heater for adsorbing the gas phase desorbed from the trap and then rapidly heating it to desorb it for introduction into gas chromatography.

[0037] The conditions for concentration are as follows: Sample quantity: 5.0g Injection volume: 200 mL of the sample gas phase in a container that has been left standing at 30°C for at least 20 minutes, and separately, 100 mL of the internal standard substance. Internal standard substance: Deuterium toluene standard gas (concentration 10 vol ppb, diluent gas is nitrogen) Concentration method: Module 1 temperature conditions: Adsorption temperature -40°C, Desorption temperature 0°C Module 2 temperature conditions: Adsorption temperature -30°C, Desorption temperature 200°C Module 3 temperature conditions: Adsorption temperature -165°C, Desorption temperature 100°C Flow rate for circulating the sample gas phase components through Module 1 and Module 2: 50 mL / min Helium flow rate for removing the residue after the gas phase components have been adsorbed onto Module 2: 75 mL Helium flow rate (flow velocity) for transferring the components of the gas phase desorbed in Module 1 to Module 2: 40 mL (100 mL / min) Time required to transfer components from the gas phase detached in Module 2 to Module 3: 3.0 minutes Desorption time for introducing the gas phase components adsorbed on module 3 into gas chromatography: 0.3 minutes The reason for using deuterated toluene standard gas as an internal standard substance in the measurement of the 3,5,5-trimethylhexanoic acid composition is to ensure that the ion peak of deuterated toluene is properly detected, that the instrument is functioning correctly, and to confirm the relative retention time with that of the 4,4-dimethyl-2-pentanone peak.

[0038] Among these, the aforementioned concentration conditions are Automatic Concentrator: Entech 7200 Automatic Concentrator manufactured by ENTECH INSTRUMENTS. Sample quantity: 5.0g Injection volume: 200 mL of the sample gas phase in a container that has been left standing at 30°C for at least 20 minutes, and separately, 100 mL of the internal standard substance. Internal standard substance: Deuterium toluene standard gas (concentration 10 vol ppb, diluent gas is nitrogen) Concentration method: CTD mode (Cold Trap Dehydration) Temperature conditions for Dehydration Module 1 (Empty Trap: ceramic-coated trap without adsorbent): Trap Temp. (adsorption temperature) -40°C, Desorption Temp. (desorption temperature) 0°C Cold Tenax® Module 2 (Tenax TA Trap: a ceramic-coated trap filled with weakly polar porous polymer beads (Tenax TA) based on 2,6-diphenyl-p-phenylene oxide as an adsorbent) temperature conditions: Trap Temp. (adsorption temperature) -30°C, Desorption Temp. (desorption temperature) 200°C Temperature conditions for Focusing Module 3 (Cryo focusing): Trap Temp. (adsorption temperature) -165°C, Desorption Temp. (desorption temperature) 100°C Sample flow rate: 50 mL / min Helium Flush Volume: 75 mL M1 to M2 Volume (Flow rate from Module 1 to Module 2): 40 mL (100 mL / min) M2 to M3 Time (Time from Module 2 to Module 3): 3.0 minutes Injection time: 0.3 minutes It is preferable that this be the case. M1, M2, and M3 correspond to Modules 1, 2, and 3 respectively, and "M1 to M2" and "M2 to M3" represent the conditions for sample exchange between modules.

[0039] -Gas chromatography- The measurement conditions for gas chromatography used to separate the volatile organic compounds (vapors) concentrated by the aforementioned automatic concentration device are as follows. Analytical column: A column with a stationary phase of dimethylpolysiloxane with a film thickness of 1 μm, measuring 60 m in length and 320 μm in inner diameter. Temperature increase program: After holding at 35°C for 2 minutes, the temperature will increase at a rate of 10°C / minute until it reaches 240°C, at which point it will be held for 7 minutes and 30 seconds. Sample introduction temperature: 220℃ Carrier gas: Helium Split ratio: 0.667:1 Control mode: Constant pressure (153.09 kPa) The concentrated sample is separated in an analytical column and then sent to a olfactory system and a mass spectrometer in a 1:1 ratio.

[0040] For the measurement equipment used in the aforementioned gas chromatography, it is preferable to use the Agilent 7890B gas chromatography system manufactured by Agilent Technologies. For example, the aforementioned analytical column can be the "DB-1" (part number: 123-1063) manufactured by Agilent Technologies.

[0041] -Mass spectrometer- The measurement conditions for the mass spectrometer are as follows: Ionization mode: EI Measurement type: Scan Ion source temperature: 250℃ Quadrupole temperature: 150℃ Electron energy: 70.0 eV Mass at which scanning begins: 30 Mass at the end of scan: 400 Calibration Curve: Using a deuterated toluene standard gas (concentration: 10 vol ppb, diluent: nitrogen), a linear calibration curve passing through the origin is created using the ion peak area of ​​deuterated toluene (EIC: m / z 98.000). For sample analysis, calculations are performed by extrapolating even if the sample falls outside the range of the calibration curve.

[0042] During data analysis, the EIC peak area (EIC: m / z) of 4,4-dimethyl-2-pentanone, which appears at the relative retention time, is determined using an extracted ion chromatogram (EIC) with the relative retention time of deuterium toluene set to 1.0, as shown in Table 1. The 4,4-dimethyl-2-pentanone peak is identified beforehand by confirming its relative retention time and mass spectrum using the respective reagents.

[0043] [Table 1]

[0044] In the aforementioned mass spectrometry, it is preferable to use the Agilent 5977B MSD manufactured by Agilent Technologies.

[0045] To calculate the deuterated toluene equivalent concentration of 4,4-dimethyl-2-pentanone in the vapor of a 3,5,5-trimethylhexanoic acid composition, it is assumed that the sensitivity of the EIC peak of 4,4-dimethyl-2-pentanone is equal to that of the EIC peak of deuterated toluene, and the calculation is performed using the formula derived from the calibration curve described above. It is desirable to create a calibration curve each time a measurement is performed. If multiple peaks exist at the relative retention times shown in Table 1, the peak areas other than those previously identified are not included in the calculation. Furthermore, the deuterated toluene equivalent concentration of 4,4-dimethyl-2-pentanone contained in the measurement environment is analyzed, and the respective concentrations are calculated as the difference.

[0046] (Composition for cosmetic ingredients) The aforementioned cosmetic raw material composition comprises a 3,5,5-trimethylhexanoic acid composition and may further contain other components. The 3,5,5-trimethylhexanoic acid composition is as described above in "(3,5,5-trimethylhexanoic acid composition)".

[0047] The aforementioned cosmetic raw material composition can be incorporated into a cosmetic composition after derivatizing the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition.

[0048] (Refrigerating machine oil raw material composition) The aforementioned refrigerant oil raw material composition comprises a 3,5,5-trimethylhexanoic acid composition and may further contain other components. The 3,5,5-trimethylhexanoic acid composition is as described above in "(3,5,5-trimethylhexanoic acid composition)".

[0049] The aforementioned refrigerant oil raw material composition can be incorporated into the refrigerant oil composition after derivatizing the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition.

[0050] (Odor suppression methods) The odor suppression method described above is an odor suppression method for a 3,5,5-trimethylhexanoic acid composition. The odor suppression method includes a formic acid concentration adjustment step and may further include other steps.

[0051] - Formic acid concentration adjustment process - The formic acid concentration adjustment step is a step of adjusting the formic acid concentration as a trace component in a 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid, to greater than 0 ppm by mass and less than or equal to 25 ppm by mass, as measured by liquid chromatography analysis under the following measurement conditions. The 3,5,5-trimethylhexanoic acid composition is as described above in "(3,5,5-trimethylhexanoic acid composition)". (Measurement conditions) Column: Packed column for reverse-phase chromatography, 25 cm in length and 4.6 mm in inner diameter. Stationary phase of the analytical column (gel particles packed into the column): Particle size 5 μm, pore size 100 Å, non-surface area 450 m², with octadecyl groups introduced as a monolayer on the surface. 2 Silica gel particles with a pore volume of 1.10 mL / g and a carbon content of 15%. Mobile phase: Mobile phase A: 0.1% by mass aqueous phosphoric acid solution, Mobile phase B: Acetonitrile Gradient conditions: The ratio of mobile phase A to mobile phase B is changed as follows depending on the analysis time. 0-15 minutes Mobile phase A100% 15-25 minutes: Linearly change from mobile phase A (100%) to mobile phase B (100%). 25-30 minutes Mobile phase B100% 30-40 minutes: Linearly change from mobile phase B (100%) to mobile phase A (100%). 40-60 minutes Mobile phase A100% Mobile phase flow rate: 1.0mL / min Column oven temperature: 40℃ Detector: UV detector Usage wavelength: 210nm Sample injection method: Autosampler used Sample injection volume: 10.0 μL Sample dilution: Use without dilution. Calibration curve: Analyze three or more samples with known formic acid concentrations and create a calibration curve using the peak area of ​​the formic acid component.

[0052] There are no particular restrictions on the method for adjusting the formic acid concentration in the formic acid concentration adjustment step, and it can be appropriately selected depending on the purpose, but examples include adding formic acid. There are no particular restrictions on the method of adding the formic acid, and it can be appropriately selected depending on the purpose.

[0053] In the formic acid concentration adjustment step, the preferred range of the formic acid concentration is as described above in "(3,5,5-trimethylhexanoic acid composition)".

[0054] (Method for producing a low-odor 3,5,5-trimethylhexanoic acid composition) The method for producing the low-odor 3,5,5-trimethylhexanoic acid composition includes a formic acid concentration adjustment step and may further include other steps. The formic acid concentration adjustment step is as described in the "(Odor Suppression Method)" section above.

[0055] (Method of manufacturing cosmetic compositions) The method for producing the cosmetic composition is a method for producing a cosmetic composition using the 3,5,5-trimethylhexanoic acid composition. The method for producing the cosmetic composition includes a step of derivatizing the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition, and may further include other steps. The 3,5,5-trimethylhexanoic acid composition is as described above in "(3,5,5-trimethylhexanoic acid composition)".

[0056] The 3,5,5-trimethylhexanoic acid composition can be incorporated into the cosmetic composition after derivatizing the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition.

[0057] There are no particular limitations on the derivatization method, and it can be appropriately selected depending on the purpose. For example, this includes esterification of a carboxylic acid containing 3,5,5-trimethylhexanoic acid with a hydroxyl group-containing compound. The hydroxyl group-containing compound may be used alone or in combination of two or more. In addition, a carboxyl group-containing compound other than 3,5,5-trimethylhexanoic acid may be used in combination during the esterification process.

[0058] Examples of derivatives of 3,5,5-trimethylhexanoic acid in the aforementioned cosmetic composition include cetyl isononanoate, BG diisononanoate, octyl isononanoate, isodecyl isononanoate, isononyl isononanoate, cetearyl isononanoate, tridecyl isononanoate, isostearyl isononanoate, isotridecyl isononanoate, ethylhexyl isononanoate, tricyclodecanemethyl isononanoate, diethylene glycol diisononanoate, neopentyl glycol diisononanoate, pentaerythrityl tetraisononanoate, polyglyceryl-20 octaisononanoate, dipentaerythrityl hexaisononanoate, dipentaerythrityl pentaisononanoate, di(ethylhexanoate / isononanoate)diethylene glycol, (polyglyceryl-2 isononanoate / dimer dilinoleate) copolymer, (trimethylpentanediol / adipic acid / isononanoate) copolymer, and the like.

[0059] (Method for producing refrigerant oil composition) The method for producing the refrigerant oil composition is a method for producing the refrigerant oil composition using the 3,5,5-trimethylhexanoic acid composition. The method for producing the refrigeration oil composition includes a step of derivatizing the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition, and may further include other steps. The 3,5,5-trimethylhexanoic acid composition is as described above in "(3,5,5-trimethylhexanoic acid composition)".

[0060] The 3,5,5-trimethylhexanoic acid composition can be incorporated into the refrigeration oil composition after derivatizing the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition.

[0061] There are no particular limitations on the derivatization method, and it can be appropriately selected depending on the purpose. For example, this includes esterification of a carboxylic acid containing 3,5,5-trimethylhexanoic acid with a hydroxyl group-containing compound. The hydroxyl group-containing compound may be used alone or in combination of two or more. In addition, a carboxyl group-containing compound other than 3,5,5-trimethylhexanoic acid may be used in combination during the esterification process.

[0062] Examples of derivatives of 3,5,5-trimethylhexanoic acid in the aforementioned refrigeration oil composition include esters of polyhydric alcohols containing 3,5,5-trimethylhexanoic acid.

[0063] Examples of the aforementioned polyhydric alcohols include ethylene glycol, 1,3-propanediol, propylene glycol, 1,2-butanediol, 1,4-butanediol, 1,5-pentanediol, 2-methyl-1,3-propanediol, neopentyl glycol, 1,6-hexanediol, 1,7-heptanediol, 2-ethyl-2-methyl-1,3-propanediol, 1,8-octanediol, and 2,2-diethyl-1 ,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, 2-methyl-2-propyl-1,3-propanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, 1,12-dodecanediol, glycerin, 1,3,5-pentanetriol, trimethylolethane, trimethylolpropane, trimethylolbutane, 3-hydroxy-2,2-dimethylpropyl-3 Examples include -hydroxy-2,2-dimethylpropanoate, pentaerythritol, polyglycerin (2-20 glycerin units), ditrimethylolpropane, dipentaerythritol, tripentaerythritol, di-(trimethylolpropane), tri-(trimethylolpropane), bispentaerythritol, di-(pentaerythritol), tri-(pentaerythritol), sorbitol, sorbitan, sorbitol-glycerin condensate, sugar alcohols such as adonitol, arabitol, xylitol, and mannitol, sugars such as xylose, arabinose, ribose, rhamnose, glucose, fructose, galactose, mannose, sorbose, cellobiose, maltose, isomaltose, trehalose, sieclose, rhauinose, gentianose, and melegitose, as well as partial methylated compounds of these, methyl glucosides (glycosides), etc. The aforementioned polyhydric alcohol may be used alone or in combination of two or more types.

[0064] The esters of carboxylic acids containing 3,5,5-trimethylhexanoic acid and polyhydric alcohols can be combined with carboxylic acids other than 3,5,5-trimethylhexanoic acid. Other carboxylic acids besides 3,5,5-trimethylhexanoic acid include, for example, butyric acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, isobutyric acid, 2-methylbutyric acid, 3-methylbutyric acid, 2,2-dimethylpropanoic acid, 2-ethylbutyric acid, 2-methylpentanoic acid, 4-methylpentanoic acid, 2-methylhexanoic acid, 2-ethyl-2-methylbutyric acid, 2,2-dimethylpentanoic acid, 2-methylheptanoic acid, 2-ethylhexanoic acid, 3-ethylhexanoic acid, 2-ethyl-2-methylpentanoic acid, 2-ethyl-4-methylpentanoic acid, 2,2-dimethylheptanoic acid, isodecanoic acid, isotridecanoic acid, fisetelic acid, myristoleic acid, palmitoleic acid, and heptadecenyleneic acid. , petroselysic acid, elaidic acid, oleic acid, vaccenic acid, linoleic acid, linolelysic acid, hiragonic acid, linolenic acid, and linear or branched aliphatic monocarboxylic acids such as arachidonic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, methylmalonic acid, ethylmalonic acid, dimethylmalonic acid, methylsuccinic acid, 2,2-dimethylsuccinic acid Examples include acids, 2,3-dimethylsuccinic acid, 2-ethyl-2-methylsuccinic acid, 2-methylglutaric acid, 3-methylglutaric acid, 3-methyladipic acid, maleic acid, fumaric acid, itaconic acid, citraconic acid, mesaconic acid, 1,2-cyclohexanedicarboxylic acid, 4-cyclohexen-1,2-dicarboxylic acid, phthalic acid, terephthalic acid, isophthalic acid, trimellitic acid, pyromellitic acid, and other polycarboxylic acids. The carboxylic acids other than 3,5,5-trimethylhexanoic acid may be used individually or in combination of two or more. [Examples]

[0065] The following describes embodiments of the present invention, but the present invention is not limited in any way to these embodiments.

[0066] (Comparative Example 1) -Synthesis process- Crude 3,5,5-trimethylhexanoic acid was synthesized according to Example 15 of International Publication No. 2022 / 118917. Specifically, 3,5,5-trimethylhexanal was synthesized by the hydroformylation reaction of diisobutylene and oxogas, and crude 3,5,5-trimethylhexanoic acid was obtained by the subsequent oxidation reaction.

[0067] -Distillation Process- 239.50 g of crude 3,5,5-trimethylhexanoic acid obtained in the above synthesis step was placed in a 300 mL three-necked flask equipped with a reflux condenser and thermometer, and subjected to vacuum distillation at 25 kPa. The fraction collected when the column top temperature was between 188 and 191 °C was obtained to yield 184.64 g of purified 3,5,5-trimethylhexanoic acid with a recovery rate of 77.1%.

[0068] (Example 1) A mixture was obtained by mixing 89.90 g of purified 3,5,5-trimethylhexanoic acid obtained in Comparative Example 1 with 0.10 g of formic acid (Fujifilm Wako Pure Chemical Industries, Ltd., reagent grade, purity 89.4%). Furthermore, 89.64 g of the purified 3,5,5-trimethylhexanoic acid obtained in Comparative Example 1 was mixed with 0.36 g of the aforementioned mixture to obtain a 3,5,5-trimethylhexanoic acid composition containing 4.0 ppm by mass of formic acid.

[0069] (Example 2) 89.09 g of purified 3,5,5-trimethylhexanoic acid obtained by the same method as in Comparative Example 1 was mixed with 0.91 g of the mixture obtained in Example 1 to obtain a 3,5,5-trimethylhexanoic acid composition containing 10 ppm by mass of formic acid.

[0070] (Example 3) 88.64 g of purified 3,5,5-trimethylhexanoic acid obtained by the same method as in Comparative Example 1 was mixed with 1.36 g of the mixture obtained in Example 1 to obtain a 3,5,5-trimethylhexanoic acid composition containing 15 ppm by mass of formic acid.

[0071] (Example 4) 88.187 g of purified 3,5,5-trimethylhexanoic acid obtained by the same method as in Comparative Example 1 was mixed with 1.82 g of the mixture obtained in Example 1 to obtain a 3,5,5-trimethylhexanoic acid composition containing 20 ppm by mass of formic acid.

[0072] (Comparative Example 2) 87.28 g of purified 3,5,5-trimethylhexanoic acid obtained by the same method as in Comparative Example 1 was mixed with 2.72 g of the mixture obtained in Example 1 to obtain a 3,5,5-trimethylhexanoic acid composition containing 30 ppm by mass of formic acid.

[0073] <Analysis 1 (Gas Chromatography Analysis)> The 3,5,5-trimethylhexanoic acid or 3,5,5-trimethylhexanoic acid compositions obtained in Examples 1-4 and Comparative Examples 1-2 were subjected to gas chromatography analysis under the following conditions. The concentration of 3,5,5-trimethylhexanoic acid was calculated as the area percentage (%) of the peak containing 3,5,5-trimethylhexanoic acid relative to the total peak area. The results are shown in Table 2.

[0074] -Gas chromatography analysis conditions- (Measurement conditions) Equipment: "Gas Chromatography 2010 Plus" manufactured by Shimadzu Corporation. Analytical column: "DB-FFAP" manufactured by Agilent Technologies (a 30m long, 0.25mm inner diameter column with a stationary phase containing 0.25μm thick high-polarity polyethylene glycol) (Part number: 122-3232) Temperature increase program: After holding at 80°C for 1 minute, the temperature was increased at 10°C / minute until it reached 210°C, where it was held for 26 minutes. Sample introduction temperature: 250℃ Carrier gas: Nitrogen Column gas flow rate: 1.0 mL / min Detector and detection temperature: Flame ionization detector (FID), 250°C Control mode: Constant speed mode Split ratio: 50:1 Sample injection conditions: 0.5 μL

[0075] <Analysis 2 (Formic Acid Concentration Measurement)> Liquid chromatography analysis was performed on the 3,5,5-trimethylhexanoic acid or 3,5,5-trimethylhexanoic acid compositions obtained in Examples 1-4 and Comparative Examples 1-2 under the following conditions. Using reagents with known formic acid purity, the formic acid concentration was analyzed in the range of 5 ppm to 120 ppm by mass. A calibration curve was created using the results converted to formic acid purity, and quantitative analysis was performed. The results are shown in Table 2. In Table 2, "-" means "below the detection limit".

[0076] - Liquid chromatography analysis conditions - Equipment: Shimadzu Corporation LC-2050C-3D Analytical column: TSKgel ODS-100V 5μm (4.6mm inner diameter, 25cm length), manufactured by Tosoh Corporation. Mobile phase: Mobile phase A: 0.1% by mass aqueous phosphoric acid solution, Mobile phase B: Acetonitrile Gradient conditions: The ratio of mobile phase A to mobile phase B is changed as follows depending on the analysis time. 0-15 minutes Mobile phase A100% 15-25 minutes: Linearly change from mobile phase A (100%) to mobile phase B (100%). 25-30 minutes Mobile phase B100% 30-40 minutes: Linearly change from mobile phase B (100%) to mobile phase A (100%). 40-60 minutes Mobile phase A100% Mobile phase flow rate: 1.0mL / min Column oven temperature: 40℃ Detector: UV detector Usage wavelength: 210nm Sample injection method: Autosampler used Sample injection volume: 10.0 μL Sample dilution: Use without dilution. Calibration curve: Formic acid (Fujifilm Wako Pure Chemical Industries, Ltd., reagent grade, purity 89.4%) was diluted with deionized water to adjust the formic acid concentration to 1 ppm by mass, 10 ppm by mass, 20 ppm by mass, and 40 ppm by mass. Samples were measured, and a calibration curve was created using the peak area of ​​formic acid.

[0077] [Table 2]

[0078] <Storage Stability Test> The 3,5,5-trimethylhexanoic acid or 3,5,5-trimethylhexanoic acid compositions obtained in Examples 1-4 and Comparative Examples 1-2 were placed in 20 mL glass containers, each sealed, under an air atmosphere, and left to stand in a constant temperature bath maintained at 80°C. After one week of standing in the constant temperature bath, the 3,5,5-trimethylhexanoic acid or 3,5,5-trimethylhexanoic acid compositions were removed. The 3,5,5-trimethylhexanoic acid or 3,5,5-trimethylhexanoic acid composition, which was extracted after the storage stability test, was subjected to olfactory gas chromatography / mass spectrometry under the conditions described below. The conditions for the aforementioned storage stability test refer to accelerated conditions for creating a state in which 3,5,5-trimethylhexanoic acid or a 3,5,5-trimethylhexanoic acid composition has been stored for a long period of time.

[0079] <Analysis 3 (Odor Gas Chromatography / Mass Spectrometry)> After the storage stability test, the concentration of 4,4-dimethyl-2-pentanone was measured in the 3,5,5-trimethylhexanoic acid or 3,5,5-trimethylhexanoic acid compositions obtained in Examples 1-4 and Comparative Examples 1-2 by olfactory gas chromatography / mass spectrometry according to the following method. The olfactory gas chromatography / mass spectrometry was performed using the apparatus shown in the schematic diagram of Figure 1. This apparatus consists of a concentrator that aspirates the gas phase of the sample filled in a container, removes H2O, N2, O2, and CO2, and concentrates the remaining volatile organic compounds; a gas chromatograph that separates the concentrated volatile organic compounds using a capillary column; an olfactory system that allows direct smelling of the separated components; and a mass spectrometer that qualitatively and quantitatively analyzes the separated components.

[0080] -Sample concentration- 5.0 g of the obtained 3,5,5-trimethylhexanoic acid composition was filled into a 500 mL resealable container and allowed to stand at 30°C for at least 20 minutes. Then, 200 mL of the gas phase was aspirated and introduced into an automatic concentrator. Automatic Concentrator: Entech 7200 Automatic Concentrator manufactured by ENTECH INSTRUMENTS. Sample quantity: 5.0g Container capacity: 500mL Injection volume: 200 mL in the gas phase, and separately from the above gas phase, 100 mL of internal standard substance. Internal standard material: Heavy toluene standard gas (concentration 10 vol ppb, diluent gas: nitrogen, Sumitomo Seika Co., Ltd.) Concentration method: CTD mode (Cold Trap Dehydration) Temperature conditions for Dehydration Module 1 (Empty Trap: ceramic-coated trap without adsorbent): Trap Temp. -40℃, Desorption Temp. 0℃ Cold Tenax® Module 2 (Tenax TA Trap: a ceramic-coated trap filled with weakly polar porous polymer beads (Tenax TA) based on 2,6-diphenyl-p-phenylene oxide as an adsorbent) temperature conditions: Trap Temp. -30℃, Desorption Temp. 200℃ Temperature conditions for Focusing Module 3 (Cryo focusing): Trap Temp. -165℃, Desorption Temp. 100℃ Sample flow rate: 50 mL / min Flush Volume: 75mL M1 to M2 Volume: 40mL(100mL / min) M2 to M3 Time: 3.0 minutes Injection time: 0.3 minutes

[0081] -Gas chromatography- Measurement equipment: Agilent 7890B gas chromatography system manufactured by Agilent Technologies. Analytical column: Agilent Technologies DB-1 (part number: 123-1063) (60 m long x 320 μm inner diameter column with a dimethylpolysiloxane stationary phase of 1 μm thickness) Temperature increase program: After holding at 35°C for 2 minutes, the temperature was increased at 10°C / minute until it reached 240°C, where it was held for 7 minutes and 30 seconds. Sample introduction temperature: 220℃ Carrier gas: Helium Split ratio: 0.667:1 Control mode: Constant pressure (153.09 kPa) The concentrated sample was separated using a capillary column and then sent to an odor detection system and a mass spectrometer in a 1:1 ratio.

[0082] -Mass spectrometer- Measurement equipment: Agilent 5977B MSD, manufactured by Agilent Technologies. Ionization mode: EI Measurement type: Scan Ion source temperature: 250℃ Quadrupole temperature: 150℃ Electron energy: 70.0 eV Mass at which scanning begins: 30 Mass at the end of scan: 400 Calibration Curve: Using a deuterated toluene standard gas (concentration: 10 vol ppb, diluent: nitrogen) manufactured by Sumitomo Seika Co., Ltd., the ion peak area of ​​deuterated toluene (EIC: m / z 98.000) was measured at injection volumes of 50 mL, 100 mL, 150 mL, and 200 mL. Using the same injection volume of 200 mL as the sample measurement as a reference, the measurements at injection volumes of 50 mL, 100 mL, and 150 mL were considered to correspond to measurements of deuterated toluene concentrations of 2.5 vol ppb, 5.0 vol ppb, and 7.5 vol ppb, respectively, based on the volume ratio, and a linear calibration curve passing through the origin was created. For the analysis of the sample, calculations were performed by extrapolation even when the values ​​were outside the range of the calibration curve.

[0083] During data analysis, the EIC peak area (EIC: m / z) of 4,4-dimethyl-2-pentanone, which appears at the relative retention time, was confirmed using extracted ion chromatograms (EIC) with the relative retention time of deuterium toluene set to 1.0, as shown in Table 3. The 4,4-dimethyl-2-pentanone peak was identified beforehand by confirming its relative retention time and mass spectrum using the respective reagents.

[0084] [Table 3]

[0085] To calculate the deuterated toluene equivalent concentration of 4,4-dimethyl-2-pentanone in the vapor of 3,5,5-trimethylhexanoic acid or a 3,5,5-trimethylhexanoic acid composition, it was assumed that the sensitivity of the EIC peak of 4,4-dimethyl-2-pentanone was equal to that of the EIC peak of deuterated toluene (EIC: m / z 98.000), and the calculation was performed using Equation 1, derived from the calibration curve described above. Furthermore, the deuterated toluene equivalent concentration of 4,4-dimethyl-2-pentanone contained in the measurement environment with a sample amount of 0 g was analyzed, and the respective concentrations were calculated as the difference. The results are shown in Table 2.

number

[0086] <Odor Evaluation> After the storage stability test, 10 g each of the 3,5,5-trimethylhexanoic acid or 3,5,5-trimethylhexanoic acid compositions obtained in Examples 1-4 and Comparative Examples 1-2 was placed in a 20 mL wide-mouth bottle, the lid was closed, and the bottle was left to stand at room temperature for 30 minutes. Afterward, the lid was opened, and the three panelists evaluated the odor based on the following evaluation criteria. The results (average values ​​of the three panelists) are shown in Table 2.

[0087] -Evaluation Criteria- 1: I smell a sewage-like odor. 2: I can smell a slight sewage-like odor. 3: It doesn't smell like sewage.

[0088] The results in Table 2 show that a 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid and formic acid in a concentration of more than 0 ppm by mass and less than or equal to 25 ppm by mass can be obtained with suppressed odor.

[0089] Examples of embodiments of the present invention include the following: <1> It contains 3,5,5-trimethylhexanoic acid and formic acid as a trace component. This 3,5,5-trimethylhexanoic acid composition is characterized in that the concentration of formic acid, as measured by liquid chromatography under the following measurement conditions, is greater than 0 ppm by mass and less than or equal to 25 ppm by mass. (Measurement conditions) Column: Packed column for reverse-phase chromatography, 25 cm in length and 4.6 mm in inner diameter. Stationary phase of the analytical column: A monolayer of octadecyl groups introduced on the surface, with a particle size of 5 μm, a pore size of 100 Å, and a non-surface area of ​​450 m². 2 Silica gel particles with a pore volume of 1.10 mL / g and a carbon content of 15%. Mobile phase: Mobile phase A: 0.1% by mass aqueous phosphoric acid solution, Mobile phase B: Acetonitrile Gradient conditions: The ratio of mobile phase A to mobile phase B is changed as follows depending on the analysis time. 0-15 minutes Mobile phase A100% 15-25 minutes: Linearly change from mobile phase A (100%) to mobile phase B (100%). 25-30 minutes Mobile phase B100% 30-40 minutes: Linearly change from mobile phase B (100%) to mobile phase A (100%). 40-60 minutes Mobile phase A100% Mobile phase flow rate: 1.0mL / min Column oven temperature: 40℃ Detector: UV detector Usage wavelength: 210nm Sample injection method: Autosampler used Sample injection volume: 10.0 μL Sample dilution: Use without dilution. Calibration curve: Analyze three or more samples with known formic acid concentrations and create a calibration curve using the peak area of ​​the formic acid component. <2> The concentration of the formic acid is 0.10 ppm by mass or more and 22 ppm by mass or less. <1> This is the 3,5,5-trimethylhexanoic acid composition described in [reference]. <3> It contains 4,4-dimethyl-2-pentanone as a trace component, The deuterized toluene equivalent concentration of 4,4-dimethyl-2-pentanone, measured by olfactory gas chromatography / mass spectrometry under the following measurement conditions, is between 5.0 volume ppb and 50 volume ppb. <1> This is the 3,5,5-trimethylhexanoic acid composition described in [reference]. (Measurement conditions) -concentrated- Automatic Concentration Apparatus: A concentration apparatus consisting of a device for aspirating the gas phase of a container in which organic compounds are placed, Module 1 which is a ceramic-coated trap without an adsorbent for removing moisture from the gas phase, Module 2 which is a ceramic-coated trap filled with weakly polar porous polymer beads based on 2,6-diphenyl-p-phenylene oxide as an adsorbent for adsorbing the gas phase from which moisture has been removed and for removing nitrogen, oxygen, carbon dioxide, and methane, and Module 3 which is a rapid heater for adsorbing the gas phase desorbed from the trap and then rapidly heating and desorbing it for introduction into gas chromatography. Sample quantity: 5.0g Injection volume: 200 mL of the sample gas phase in a container that has been left standing at 30°C for at least 20 minutes, and separately, 100 mL of the internal standard substance. Internal standard substance: Deuterium toluene standard gas (concentration 10 vol ppb, diluent gas is nitrogen) Concentration method: Module 1 temperature conditions: Adsorption temperature -40°C, Desorption temperature 0°C Module 2 temperature conditions: Adsorption temperature -30°C, Desorption temperature 200°C Module 3 temperature conditions: Adsorption temperature -165°C, Desorption temperature 100°C Flow rate for circulating the sample gas phase components through Module 1 and Module 2: 50 mL / min Helium flow rate for removing the residue after the gas phase components have been adsorbed onto Module 2: 75 mL Helium flow rate (flow velocity) for transferring the components of the gas phase desorbed in Module 1 to Module 2: 40 mL (100 mL / min) Time required to transfer components from the gas phase detached in Module 2 to Module 3: 3.0 minutes Desorption time for introducing the gas phase components adsorbed on module 3 into gas chromatography: 0.3 minutes -Gas chromatography- Analytical column: A column with a stationary phase of dimethylpolysiloxane with a film thickness of 1 μm, measuring 60 m in length and 320 μm in inner diameter. Temperature increase program: Hold at 35°C for 2 minutes, then increase the temperature at 10°C / minute until it reaches 240°C, then hold for 7 minutes and 30 seconds. Sample introduction temperature: 220℃ Carrier gas: Helium Split ratio: 0.667:1 Control mode: Constant pressure (153.09 kPa) The concentrated sample is separated using a capillary column and then sent to an odor detection system and a mass spectrometer in a 1:1 ratio. -Mass spectrometry- Ionization mode: EI Measurement type: Scan Ion source temperature: 250℃ Quadrupole temperature: 150℃ Electron energy: 70.0 eV Mass at which scanning begins: 30 Mass at the end of scan: 400 Calibration curve: Using deuterated toluene standard gas (concentration: 10 vol ppb, diluent: nitrogen), a linear calibration curve passing through the origin was created using the ion peak area of ​​deuterated toluene (EIC: m / z 98.000). Data Analysis: Using extracted ion chromatograms (EIC), the EIC peak area (EIC: m / z 114.000) of 4,4-dimethyl-2-pentanone appearing at relative retention times of 0.99 to 1.05, with the relative retention time of deuterium toluene set to 1.0, is used to calculate the deuterium toluene equivalent concentration from the calibration curve. <4> The aforementioned concentration conditions are, Automatic Concentrator: Entech 7200 Automatic Concentrator manufactured by ENTECH INSTRUMENTS. Sample quantity: 5.0g Injection volume: 200 mL of the sample gas phase in a container that has been left standing at 30°C for at least 20 minutes, and separately, 100 mL of the internal standard substance. Internal standard substance: Deuterium toluene standard gas (concentration 10 vol ppb, diluent gas is nitrogen) Concentration method: CTD mode (Cold Trap Dehydration) Temperature conditions for Dehydration Module 1 (Empty Trap: ceramic-coated trap without adsorbent): Trap Temp. -40℃, Desorption Temp. 0℃ Cold Tenax Module 2 (Tenax TA Trap: a ceramic-coated trap filled with weakly polar porous polymer beads based on 2,6-diphenyl-p-phenylene oxide as an adsorbent) temperature conditions: Trap Temp. -30℃, Desorption Temp. 200℃ Temperature conditions for Focusing Module 3 (Cryo focusing): Trap Temp. -165℃, Desorption Temp. 100℃ Sample flow rate: 50 mL / min Flush Volume: 75mL M1 to M2 Volume: 40mL(100mL / min) M2 to M3 Time: 3.0 minutes Injection time: 0.3 minutes And, The measuring instrument used in the aforementioned gas chromatography is the Agilent 7890B gas chromatography system manufactured by Agilent Technologies. The measuring instrument used in the aforementioned mass spectrometry is the Agilent 5977B MSD manufactured by Agilent Technologies. <3> This is the 3,5,5-trimethylhexanoic acid composition described in [reference]. <5> The aforementioned <1> from <4> This is a cosmetic raw material composition characterized by containing the 3,5,5-trimethylhexanoic acid composition described in any of the above. <6> The aforementioned <1> from <4> This is a composition for use as a raw material for refrigerant oil, characterized by containing the 3,5,5-trimethylhexanoic acid composition described in any of the above. <7> This is a method for suppressing odor in a 3,5,5-trimethylhexanoic acid composition, characterized by including a formic acid concentration adjustment step in which the formic acid concentration as a trace component is adjusted to greater than 0 ppm by mass and less than or equal to 25 ppm by mass by liquid chromatography analysis measured under the following measurement conditions. (Measurement conditions) Column: Packed column for reverse-phase chromatography, 25 cm in length and 4.6 mm in inner diameter. Stationary phase of the analytical column: A monolayer of octadecyl groups introduced on the surface, with a particle size of 5 μm, a pore size of 100 Å, and a non-surface area of ​​450 m². 2 Silica gel particles with a pore volume of 1.10 mL / g and a carbon content of 15%. Mobile phase: Mobile phase A: 0.1% by mass aqueous phosphoric acid solution, Mobile phase B: Acetonitrile Gradient conditions: The ratio of mobile phase A to mobile phase B is changed as follows depending on the analysis time. 0-15 minutes Mobile phase A100% 15-25 minutes: Linearly change from mobile phase A (100%) to mobile phase B (100%). 25-30 minutes Mobile phase B100% 30-40 minutes: Linearly change from mobile phase B (100%) to mobile phase A (100%). 40-60 minutes Mobile phase A100% Mobile phase flow rate: 1.0mL / min Column oven temperature: 40℃ Detector: UV detector Usage wavelength: 210nm Sample injection method: Autosampler used Sample injection volume: 10.0 μL Sample dilution: Use without dilution. Calibration curve: Analyze three or more samples with known formic acid concentrations and create a calibration curve using the peak area of ​​the formic acid component. <8> A method for producing a low-odor 3,5,5-trimethylhexanoic acid composition, characterized by including a formic acid concentration adjustment step in which the formic acid concentration as a trace component is adjusted to greater than 0 ppm by mass and less than or equal to 25 ppm by mass by liquid chromatography analysis measured under the following measurement conditions. (Measurement conditions) Column: Packed column for reverse-phase chromatography, 25 cm in length and 4.6 mm in inner diameter. Stationary phase of the analytical column: A monolayer of octadecyl groups introduced on the surface, with a particle size of 5 μm, a pore size of 100 Å, and a non-surface area of ​​450 m². 2 Silica gel particles with a pore volume of 1.10 mL / g and a carbon content of 15%. Mobile phase: Mobile phase A: 0.1% by mass aqueous phosphoric acid solution, Mobile phase B: Acetonitrile Gradient conditions: The ratio of mobile phase A to mobile phase B is changed as follows depending on the analysis time. 0-15 minutes Mobile phase A100% 15-25 minutes: Linearly change from mobile phase A (100%) to mobile phase B (100%). 25-30 minutes Mobile phase B100% 30-40 minutes: Linearly change from mobile phase B (100%) to mobile phase A (100%). 40-60 minutes Mobile phase A100% Mobile phase flow rate: 1.0mL / min Column oven temperature: 40℃ Detector: UV detector Usage wavelength: 210nm Sample injection method: Autosampler used Sample injection volume: 10.0 μL Sample dilution: Use without dilution. Calibration curve: Analyze three or more samples with known formic acid concentrations and create a calibration curve using the peak area of ​​the formic acid component. <9> The aforementioned <1> from <4> A method for producing a cosmetic composition using a 3,5,5-trimethylhexanoic acid composition described in any of the following: The present invention relates to a method for producing a cosmetic composition, characterized by including a step of derivatizing the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition. <10> The aforementioned <1> from <4> A method for producing a refrigeration oil composition using a 3,5,5-trimethylhexanoic acid composition described in any of the following: The present invention relates to a method for producing a refrigeration oil composition, characterized by including a step of derivatizing the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition.

Claims

1. It contains 3,5,5-trimethylhexanoic acid and formic acid as a trace component. A 3,5,5-trimethylhexanoic acid composition characterized in that the concentration of formic acid, measured by liquid chromatography under the following measurement conditions, is greater than 0 ppm by mass and less than or equal to 25 ppm by mass. (Measurement conditions) Column: Packed column for reverse-phase chromatography, 25 cm in length and 4.6 mm in inner diameter. Stationary phase of the analytical column: A monolayer of octadecyl groups introduced on the surface, with a particle size of 5 μm, a pore size of 100 Å, and a non-surface area of ​​450 m². ２ Silica gel particles with a pore volume of 1.10 mL / g and a carbon content of 15%. Mobile phase: Mobile phase A: 0.1% by mass aqueous phosphoric acid solution, Mobile phase B: Acetonitrile Gradient conditions: The ratio of mobile phase A to mobile phase B is changed as follows depending on the analysis time. 0-15 minutes Mobile phase A100% 15-25 minutes: Linearly change from mobile phase A (100%) to mobile phase B (100%). 25-30 minutes Mobile phase B100% 30-40 minutes: Linearly change from mobile phase B (100%) to mobile phase A (100%). 40-60 minutes Mobile phase A 100% Mobile phase flow rate: 1.0mL / min Column oven temperature: 40℃ Detector: UV detector Wavelength used: 210nm Sample injection method: Autosampler used Sample injection volume: 10.0 μL Sample dilution: Use without dilution. Calibration curve: Analyze three or more samples with known formic acid concentrations and create a calibration curve using the peak area of ​​the formic acid component.

2. The 3,5,5-trimethylhexanoic acid composition according to claim 1, wherein the concentration of formic acid is 0.10 ppm by mass or more and 22 ppm by mass or less.

3. It contains 4,4-dimethyl-2-pentanone as a trace component, The 3,5,5-trimethylhexanoic acid composition according to claim 1, wherein the deuterium-to-toluene concentration of 4,4-dimethyl-2-pentanone, measured by olfactory gas chromatography / mass spectrometry under the following measurement conditions, is 5.0 volume ppb or more and 50 volume ppb or less. (Measurement conditions) -concentrated- Automatic Concentration Apparatus: A concentration apparatus consisting of a device for aspirating the gas phase of a container in which organic compounds are placed, Module 1 which is a ceramic-coated trap without an adsorbent for removing moisture from the gas phase, Module 2 which is a ceramic-coated trap filled with weakly polar porous polymer beads based on 2,6-diphenyl-p-phenylene oxide as an adsorbent for adsorbing the gas phase from which moisture has been removed and for removing nitrogen, oxygen, carbon dioxide, and methane, and Module 3 which is a rapid heater for adsorbing the gas phase desorbed from the trap and then rapidly heating and desorbing it for introduction into gas chromatography. Sample quantity: 5.0 g Injection volume: 200 mL of the sample gas phase in a container that has been left standing at 30°C for at least 20 minutes, and separately, 100 mL of the internal standard substance. Internal standard substance: Deuterium toluene standard gas (concentration 10 vol ppb, diluent gas: nitrogen) Concentration method: Temperature conditions for Module 1: Adsorption temperature -40°C, Desorption temperature 0°C Module 2 temperature conditions: Adsorption temperature -30°C, Desorption temperature 200°C Temperature conditions for Module 3: Adsorption temperature -165°C, Desorption temperature 100°C Flow rate for circulating the sample gas phase components through Module 1 and Module 2: 50 mL / min Helium flow rate for removing the residue after the gas phase components have been adsorbed onto module 2: 75 mL Helium flow rate (flow velocity) for transferring the components of the gas phase desorbed in Module 1 to Module 2: 40 mL (100 mL / min) Time required to transfer the components of the gas phase detached in Module 2 to Module 3: 3.0 minutes Desorption time for introducing the gas phase components adsorbed on module 3 into gas chromatography: 0.3 minutes -Gas chromatography- Analytical column: A column with a stationary phase of dimethylpolysiloxane with a film thickness of 1 μm, measuring 60 m in length and 320 μm in inner diameter. Temperature increase program: Hold at 35°C for 2 minutes, then increase the temperature at 10°C / minute until it reaches 240°C, and hold for 7 minutes and 30 seconds. Sample introduction temperature: 220°C Carrier gas: Helium Split ratio: 0.667:1 Control mode: Constant pressure (153.09 kPa) The concentrated sample is separated using a capillary column and then sent to an odor detection system and a mass spectrometer in a 1:1 ratio. -Mass spectrometry- Ionization mode: EI Measurement type: Scan Ion source temperature: 250°C Quadrupole temperature: 150℃ Electron energy: 70.0 eV Mass at which scanning begins: 30 Mass at the end of scan: 400 Calibration curve: Using a deuterated toluene standard gas (concentration: 10 vol ppb, diluent gas: nitrogen), a linear calibration curve passing through the origin was created using the ion peak area of ​​deuterated toluene (EIC: m / z 98.000). Data Analysis: Using extracted ion chromatograms (EIC), the EIC peak area (EIC: m / z 114.000) of 4,4-dimethyl-2-pentanone appearing at relative retention times of 0.99 to 1.05, with the relative retention time of deuterium toluene set to 1.0, is used to calculate the deuterium toluene equivalent concentration from the calibration curve.

4. The aforementioned concentration conditions are, Automatic Concentrator: Entech 7200 Automatic Concentrator manufactured by ENTECH INSTRUMMENTS. Sample quantity: 5.0 g Injection volume: 200 mL of the sample gas phase in a container that has been left standing at 30°C for at least 20 minutes, and separately, 100 mL of the internal standard substance. Internal standard substance: Deuterium toluene standard gas (concentration 10 vol ppb, diluent gas: nitrogen) Concentration method: CTD mode (Cold Trap Dehydration) Temperature conditions for Dehydration Module 1 (Empty Trap: ceramic-coated trap without adsorbent): Trap Temp. -40°C, Desorbation Temp. 0°C Temperature conditions for Cold Tenax Module 2 (Tenax TA Trap: a ceramic-coated trap filled with weakly polar porous polymer beads based on 2,6-diphenyl-p-phenylene oxide as an adsorbent): Trap Temp. -30°C, Desorption Temp. 200°C Temperature conditions for Focusing Module 3 (Cryo Focusing): Trap Temp. -165°C, Desorption Temp. 100°C Sample flow rate: 50 mL / min He Flush Volume: 75mL M1 to M2 Volume: 40mL (100mL / min) M2 to M3 Time: 3.0 minutes Injection time: 0.3 minutes And, The measuring instrument used in the aforementioned gas chromatography is the Agilent 7890B gas chromatography system manufactured by Agilent Technologies. The 3,5,5-trimethylhexanoic acid composition according to claim 3, wherein the measuring instrument used in the mass spectrometry is an Agilent 5977B MSD manufactured by Agilent Technologies.

5. A cosmetic raw material composition characterized by comprising the 3,5,5-trimethylhexanoic acid composition described in any one of claims 1 to 4.

6. A composition for use as a raw material for refrigeration oil, characterized by comprising the 3,5,5-trimethylhexanoic acid composition described in any one of claims 1 to 4.

7. A method for suppressing odor in a 3,5,5-trimethylhexanoic acid composition, characterized by including a formic acid concentration adjustment step, in which the formic acid concentration as a trace component is adjusted to greater than 0 ppm by mass and less than or equal to 25 ppm by mass by liquid chromatography analysis measured under the following measurement conditions. (Measurement conditions) Column: Packed column for reverse-phase chromatography, 25 cm in length and 4.6 mm in inner diameter. Stationary phase of the analytical column: A monolayer of octadecyl groups introduced on the surface, with a particle size of 5 μm, a pore size of 100 Å, and a non-surface area of ​​450 m². ２ Silica gel particles with a pore volume of 1.10 mL / g and a carbon content of 15%. Mobile phase: Mobile phase A: 0.1% by mass aqueous phosphoric acid solution, Mobile phase B: Acetonitrile Gradient conditions: The ratio of mobile phase A to mobile phase B is changed as follows depending on the analysis time. 0-15 minutes Mobile phase A100% 15-25 minutes: Linearly change from mobile phase A (100%) to mobile phase B (100%). 25-30 minutes Mobile phase B100% 30-40 minutes: Linearly change from mobile phase B (100%) to mobile phase A (100%). 40-60 minutes Mobile phase A 100% Mobile phase flow rate: 1.0mL / min Column oven temperature: 40℃ Detector: UV detector Wavelength used: 210nm Sample injection method: Autosampler used Sample injection volume: 10.0 μL Sample dilution: Use without dilution. Calibration curve: Analyze three or more samples with known formic acid concentrations and create a calibration curve using the peak area of ​​the formic acid component.

8. A method for producing a low-odor 3,5,5-trimethylhexanoic acid composition, characterized by including a formic acid concentration adjustment step in which the formic acid concentration as a trace component, measured by liquid chromatography analysis under the following measurement conditions, is adjusted to greater than 0 ppm by mass and less than or equal to 25 ppm by mass. (Measurement conditions) Column: Packed column for reverse-phase chromatography, 25 cm in length and 4.6 mm in inner diameter. Stationary phase of the analytical column: A monolayer of octadecyl groups introduced on the surface, with a particle size of 5 μm, a pore size of 100 Å, and a non-surface area of ​​450 m². ２ Silica gel particles with a pore volume of 1.10 mL / g and a carbon content of 15%. Mobile phase: Mobile phase A: 0.1% by mass aqueous phosphoric acid solution, Mobile phase B: Acetonitrile Gradient conditions: The ratio of mobile phase A to mobile phase B is changed as follows depending on the analysis time. 0-15 minutes Mobile phase A100% 15-25 minutes: Linearly change from mobile phase A (100%) to mobile phase B (100%). 25-30 minutes Mobile phase B100% 30-40 minutes: Linearly change from mobile phase B (100%) to mobile phase A (100%). 40-60 minutes Mobile phase A 100% Mobile phase flow rate: 1.0mL / min Column oven temperature: 40℃ Detector: UV detector Wavelength used: 210nm Sample injection method: Autosampler used Sample injection volume: 10.0 μL Sample dilution: Use without dilution. Calibration curve: Analyze three or more samples with known formic acid concentrations and create a calibration curve using the peak area of ​​the formic acid component.

9. A method for producing a cosmetic composition using the 3,5,5-trimethylhexanoic acid composition described in any one of claims 1 to 4, A method for producing a cosmetic composition, characterized by comprising the step of derivatizing the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition.

10. A method for producing a refrigeration oil composition using the 3,5,5-trimethylhexanoic acid composition described in any one of claims 1 to 4, A method for producing a refrigeration oil composition, characterized by comprising the step of derivatizing the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition.

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