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

Abstract

The present invention relates to a 3, 5, 5-trimethylhexanoic acid composition or the like comprising 3, 5, 5-trimethylhexanoic acid and formic acid as a trace component, the concentration of the formic acid being more than 0 ppm by mass and 25 ppm by mass or less as determined by liquid chromatography.

Description

Technical Field

[0001] This invention relates to 3,5,5-trimethylhexanoic acid compositions, odor suppression methods in 3,5,5-trimethylhexanoic acid compositions, and methods for manufacturing low-odor 3,5,5-trimethylhexanoic acid compositions. Background Technology

[0002] It is known that 3,5,5-trimethylhexanoic acid can be synthesized by oxidation of the precursor aldehyde, namely 3,5,5-trimethylhexanal (e.g., Patent Document 1). 3,5,5-Trimethylhexanoic acid is used as a raw material in cosmetics, refrigeration oils, and metalworking fluids. Although trace amounts are present in cosmetics, refrigeration oils, and metalworking fluids, their applications necessitate a low-odor requirement for the raw material.

[0003] To date, a 3,5,5-trimethylhexanoic acid composition with low reproductive toxicity is known (Patent Document 2), but odor remains a problem in 3,5,5-trimethylhexanoic acid compositions. Existing technical documents Patent documents

[0004] Patent Document 1: International Publication No. 2022 / 118917 Patent Document 2: International Publication No. 2024 / 219140 Summary of the Invention The technical problem that the invention aims to solve

[0005] The objective of this invention is to solve the aforementioned problems and achieve the following: that is, to provide an odor-suppressed 3,5,5-trimethylhexanoic acid composition, an odor-suppressing method for the 3,5,5-trimethylhexanoic acid composition, and a method for manufacturing a low-odor 3,5,5-trimethylhexanoic acid composition. Technical solutions adopted to solve technical problems

[0006] Through repeated and in-depth research in order to achieve the aforementioned objective, the inventors have discovered that they can provide odor-suppressed 3,5,5-trimethylhexanoic acid compositions, odor-suppressing methods in 3,5,5-trimethylhexanoic acid compositions, and methods for manufacturing low-odor 3,5,5-trimethylhexanoic acid compositions.

[0007] This invention is based on the insights described above by the inventors, and is a technical solution for solving the aforementioned problem, as described below. That is, <1> A 3,5,5-trimethylhexanoic acid composition, characterized in that it comprises 3,5,5-trimethylhexanoic acid and formic acid as a trace component, wherein the concentration of said formic acid, as determined by liquid chromatography under the determination conditions described below, is greater than 0 ppm by mass and less than 25 ppm by mass. <2> A composition for use as a cosmetic ingredient, characterized in that it comprises the 3,5,5-trimethylhexanoic acid composition described in <1> above. <3> A composition for use as a raw material for refrigeration oil, characterized in that it comprises the 3,5,5-trimethylhexanoic acid composition described in <1> above. <4> A method for odor suppression in a 3,5,5-trimethylhexanoic acid composition, characterized in that it includes a formic acid concentration adjustment step, wherein in the 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid, the concentration of formic acid as a trace component, as determined by liquid chromatography under the determination conditions described below, is adjusted to be greater than 0 ppm by mass and less than 25 ppm by mass. <5> A method for manufacturing a low-odor 3,5,5-trimethylhexanoic acid composition, characterized in that it includes a formic acid concentration adjustment step, wherein in the 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid, the concentration of formic acid as a trace component, as determined by liquid chromatography under the determination conditions described below, is adjusted to be greater than 0 ppm by mass and less than 25 ppm by mass. <6> A method for manufacturing a cosmetic composition, using the 3,5,5-trimethylhexanoic acid composition described in <1> to manufacture the cosmetic composition, characterized in that it includes a step of derivatizing the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition. <7> A method for manufacturing a refrigeration oil composition, using the 3,5,5-trimethylhexanoic acid composition described in <1> to manufacture the refrigeration oil composition, characterized in that it includes a step of derivatizing the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition. Invention Effects

[0008] According to the present invention, it is possible to provide odor-suppressed 3,5,5-trimethylhexanoic acid compositions, odor suppression methods in 3,5,5-trimethylhexanoic acid compositions, and methods for manufacturing low-odor 3,5,5-trimethylhexanoic acid compositions. Attached Figure Description

[0009] Figure 1 This is an example of the apparatus used in the odor detection gas chromatography / mass spectrometry analysis of the present invention. Detailed Implementation

[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 also contain other components.

[0011] -3,5,5-trimethylhexanoic acid- The 3,5,5-trimethylhexanoic acid is composed of the molecular formula C9H 18 O2, indicated by the formula (CH3)3CCH2CH(CH3)CH2COOH, represents a compound with a molecular weight of 158.24. The 3,5,5-trimethylhexanoic acid is sometimes also referred to as isononanoic acid.

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

[0013] There are no particular restrictions on the timing of the determination of the concentration of the 3,5,5-trimethylhexanoic acid, and it can be appropriately selected according to the purpose.

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

[0015] For example, the gas chromatograph can be the "Gas Chromatograph 2010 Plus" manufactured by Shimadzu Corporation. For example, the column used in gas chromatography can be the "DB-FFAP" (part number: 122-3232) manufactured by Agilent Technologies. The determination conditions for gas chromatography are as follows. (Measurement conditions) Analytical column: A 30m long column with an inner diameter of 0.25mm containing a stationary phase of highly polar polyethylene glycol with a film thickness of 0.25μm. Temperature program: Hold at 80℃ for 1 minute, then increase the temperature at 10℃ / minute until reaching 210℃, then hold 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℃ Control mode: Constant linear velocity mode Flow split ratio: 50:1 Sample injection conditions: 0.5 μL

[0016] -Formic acid- The formic acid is a compound with the molecular formula CH2O2, the indicative formula HCOOH, and a molecular weight of 46.03. Formic acid is sometimes also referred to as methane acid.

[0017] As for the lower limit of the concentration of formic acid in the 3,5,5-trimethylhexanoic acid composition, there is no particular limitation as long as it exceeds 0 ppm by mass, and it can be appropriately selected according to the purpose. However, from the viewpoint of suppressing odor, it is preferred to be 0.10 ppm by mass or more, more preferably 1.0 ppm by mass or more, further preferably 4.0 ppm by mass or more, even more preferably 5.0 ppm by mass or more, particularly preferably 8.0 ppm by mass or more, and most preferably 10 ppm by mass or more. As for the upper limit of the concentration of formic acid in the 3,5,5-trimethylhexanoic acid composition, there is no particular limitation as long as it is 25 ppm by mass or less, and it can be appropriately selected according to the purpose. However, from the viewpoint of suppressing odor, it is preferable to be 22 ppm by mass or less, more preferably 20 ppm by mass or less, further preferably 18 ppm by mass or less, and particularly preferably 15 ppm by mass or less. Furthermore, the following numerical ranges can be used as preferred ranges: any one of the values ​​shown as lower limits and any one of the values ​​shown as upper limits can be used as the lower limit and upper limit values, respectively. Preferably, the mass concentration is 0.10 ppm or more and 22 ppm or less, more preferably 1.0 ppm or more and 22 ppm or less, further preferably 4.0 ppm or more and 20 ppm or less, even more preferably 5.0 ppm or more and 18 ppm or less, particularly preferably 8.0 ppm or more and 18 ppm or less, and most preferably 10 ppm or more and 15 ppm or less. It is believed that by setting the concentration of formic acid in the 3,5,5-trimethylhexanoic acid composition within the above-mentioned range, 4,4-dimethyl-2-pentanone is generated within a suitable range during storage, which can mask other odor components and improve odor.

[0018] There are no particular restrictions on the timing of formic acid concentration determination, and it can be appropriately selected according to the purpose. The concentration of formic acid was determined by liquid chromatography analysis as described in the section on "Determination of Formic Acid Concentration" (described later).

[0019] -Other ingredients- There are no particular limitations on the other components mentioned, and they can be appropriately selected according to the purpose. For example, 4,4-dimethyl-2-pentanone can be mentioned as a trace component.

[0020] --4,4-Dimethyl-2-pentanone-- The 4,4-dimethyl-2-pentanone is derived from the molecular formula C7H 14 O, indicated by the formula (CH3)3CCH2COCH3, represents a compound with a molecular weight of 114.19. The 4,4-dimethyl-2-pentanone is sometimes also referred to as methyl neopentyl ketone, 4,4-dimethyl-2-pentanone, neopentylmethyl ketone, 4,4-dimethylpentane-2-one, or methyl 2,2-dimethylpropyl ketone.

[0021] The concentration of the 4,4-dimethyl-2-pentanone in the 3,5,5-trimethylhexanoic acid composition was determined as a deuterated toluene equivalent concentration by means of the method described in the "Odor Identification Gas Chromatography / Mass Spectrometry Analysis" section described later.

[0022] There are no particular limitations on the lower limit of the deuterated toluene equivalent concentration of the 4,4-dimethyl-2-pentanone, which can be appropriately selected according to the purpose. Preferably, it is 5.0 volume ppb or more, more preferably 10 volume ppb or more, even more preferably 15 volume ppb or more, even more preferably 20 volume ppb or more, particularly preferably 21 volume ppb or more, and most preferably 25 volume ppb or more. There is no particular limitation on the upper limit of the deuterated toluene equivalent concentration of the 4,4-dimethyl-2-pentanone, which can be appropriately selected according to the purpose. It is preferably 50 volume ppb or less, more preferably 45 volume ppb or less, even more preferably 40 volume ppb or less, even more preferably 35 volume ppb or less, particularly preferably 30 volume ppb or less, and most preferably 28 volume ppb or less. Furthermore, the following numerical ranges can be used as preferred ranges: any one of the values ​​shown as lower limits and any one of the values ​​shown as upper limits can be used as the lower limit and upper limit values, respectively. Preferably, the volume percentage is 5.0 ppb or more and 50 ppb or less, more preferably 10 ppb or more and 45 ppb or less, even more preferably 15 ppb or more and 40 ppb or less, even more preferably 20 ppb or more and 35 ppb or less, particularly preferably 21 ppb or more and 30 ppb or less, and most preferably 25 ppb or more and 28 ppb or less.

[0023] There are no particular limitations on the timing of determining the deuterated toluene equivalent concentration of the 4,4-dimethyl-2-pentanone, and it can be appropriately selected according to the purpose. For example, it can be after the manufacture of the 3,5,5-trimethylhexanoic acid composition, or after heating the 3,5,5-trimethylhexanoic acid composition at 80°C for one week in an air atmosphere.

[0024] In the 3,5,5-trimethylhexanoic acid composition of this embodiment, "after heating at 80°C for one week in an air atmosphere" refers to the accelerated conditions used to prepare the 3,5,5-trimethylhexanoic acid composition for long-term storage.

[0025] - Method for manufacturing 3,5,5-trimethylhexanoic acid composition - There are no particular limitations on the method for manufacturing the 3,5,5-trimethylhexanoic acid composition, which can be appropriately selected according to the purpose, and can be manufactured by a method including a synthesis step, a purification step, and a formic acid concentration adjustment step.

[0026] --Synthesis Process-- The synthesis process is the process of synthesizing crude 3,5,5-trimethylhexanoic acid. The 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 crude 3,5,5-trimethylhexanoic acid, and it can be appropriately selected according to the purpose. For example, the method described in International Publication No. 2022 / 118917 can be cited. Specifically, for example, 3,5,5-trimethylhexanal can be synthesized by hydroformylation of diisobutylene and carbonyl syngas, followed by oxidation to synthesize crude 3,5,5-trimethylhexanoic acid.

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

[0029] ---Distillation Process--- The distillation process is a process of removing components with lower boiling points (low-boiling components) and components with higher boiling points (high-boiling components) compared to the boiling point (120℃ / 13mmHg) of 3,5,5-trimethylhexanoic acid. 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 to recover the fraction with a top temperature between 180 and 200 °C, thereby obtaining purified 3,5,5-trimethylhexanoic acid. The purified 3,5,5-trimethylhexanoic acid refers to the purified 3,5,5-trimethylhexanoic acid.

[0030] --Formic acid concentration adjustment process-- The formic acid concentration adjustment process is as follows: in the 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid, the formic acid concentration as a trace component, as determined by liquid chromatography under the conditions described below, is adjusted to be greater than 0 ppm by mass and less than 25 ppm by mass.

[0031] There are no particular restrictions on the method for adjusting the formic acid concentration in the formic acid concentration adjustment process, and it can be appropriately selected according to the purpose. Examples include adding formic acid. There are no particular limitations on the method of adding formic acid, and it can be appropriately selected according to the purpose.

[0032] <Formic acid concentration determination> The formic acid concentration determination was performed using liquid chromatography analysis of the 3,5,5-trimethylhexanoic acid composition under the following conditions. Using reagents with pre-known formic acid purity, analysis was conducted within a formic acid concentration range of 5 ppm to 120 ppm by mass. A calibration curve was constructed using the results converted to formic acid purity for quantitative analysis.

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

[0034] The determination conditions for liquid chromatography analysis are as follows. Column: A packed column for reversed-phase chromatography, 25 cm in length and 4.6 mm in inner diameter. The stationary phase of the analytical column (gel particles packed into the column): octadecyl groups were introduced into the surface in a monolayer, with a particle size of 5 μm, a pore size of 100 Å, and a specific 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 phases: Mobile phase A 0.1% by mass phosphoric acid aqueous solution, Mobile phase B acetonitrile Gradient conditions: Adjust the ratio of mobile phase A to mobile phase B according to the analysis time as follows. 0-15 minute moving phase A100% The phase transitions linearly from 100% moving phase A to 100% moving phase B within 15-25 minutes. 25-30 minute moving phase B100% The phase changes linearly from 100% B to 100% A over 30-40 minutes. 40-60 minute moving phase A100% Mobile phase flow rate: 1.0 mL / min Column oven temperature: 40℃ Detector: UV detector Wavelength used: 210nm Sample injection method: using an autosampler Sample injection volume: 10.0 μL Sample diluted or not: used undiluted Calibration curve: Perform at least three analyses on samples with formic acid concentrations ranging from 1 ppm to 40 ppm, and construct a calibration curve using the peak areas of formic acid.

[0035] <Odor Identification Gas Chromatography / Mass Spectrometry Analysis> The odor detection gas chromatography / mass spectrometry analysis used Figure 1 The apparatus is shown in the schematic diagram. It consists of a concentration unit, a gas chromatograph, an odor detection system, and a mass spectrometer. The concentration unit draws in the gas phase of the sample packed into a container, removes H2O, N2, O2, and CO2, and concentrates the remaining volatile organic compounds (sample vapor in the gas phase of the sample). The gas chromatograph separates the concentrated volatile organic compounds (vapor) using a capillary column. The odor detection system can directly detect the separated components, and the mass spectrometer performs qualitative and quantitative analysis of the separated components.

[0036] -concentrate- 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 was filled into a sealable 500 mL 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 automated concentration device. The automatic concentration device comprises a device for attracting a gas phase containing a container holding organic compounds, module 1, module 2, and module 3. Module 1 is a ceramic-coated trap unfilled with an adsorbent for removing moisture from the gas phase. Module 2 is a ceramic-coated trap filled with weakly polar porous polymer microspheres based on 2,6-diphenyl-p-phenylene oxide as an adsorbent for removing moisture from the gas phase and removing nitrogen, oxygen, carbon dioxide, and methane. Module 3 is a rapid heater for adsorbing the gas phase desorbed from the trap, followed by rapid heating to desorb it, thereby introducing it into a gas chromatograph.

[0037] The conditions for concentration are as follows. Sample size: 5.0g Injection volume: 200 mL of the sample gas phase in a container that has been left to stand at 30°C for at least 20 minutes, and 100 mL of an additional internal standard. Internal standard: deuterated toluene standard gas (concentration 10 ppb / v, dilution gas: nitrogen) Concentration method: Temperature conditions for module 1: Adsorption temperature -40℃, desorption temperature 0℃ Temperature conditions for module 2: Adsorption temperature -30℃, desorption temperature 200℃ Temperature conditions for module 3: Adsorption temperature -165℃, desorption temperature 100℃ The flow rate of the sample gas phase components through modules 1 and 2 is 50 mL / min. The helium flow rate used to remove the remaining components after the gas phase components are adsorbed into module 2 is 75 mL. Helium flow rate (rate) for transferring components desorbed from the gas phase of module 1 to module 2: 40 mL (100 mL / min) Time required to transfer components desorbed from the gas phase of module 2 to module 3: 3.0 minutes Desorption time for introducing components adsorbed in the gas phase of module 3 into the gas chromatograph: 0.3 minutes. The reason for using deuterated toluene standard gas as an internal standard in the determination of the 3,5,5-trimethylhexanoic acid composition is to confirm that the ion peak of deuterated toluene is properly detected, that the apparatus is functioning normally, and the relative retention time with the peak of 4,4-dimethyl-2-pentanone.

[0038] The preferred conditions for concentration are: Automatic concentration unit: Entech 7200 automatic concentration unit manufactured by ENTECH INSTRUMENTS. Sample size: 5.0g Injection volume: 200 mL of the sample gas phase and 100 mL of an additional internal standard in a container that has been left to stand at 30°C for at least 20 minutes. Internal standard: deuterated toluene standard gas (concentration 10 ppb / v, dilution gas is nitrogen). Concentration method: CTD mode (cold trap dehydration). Temperature conditions for Dehydration Module 1 (Empty Trap: a ceramic-coated trap without adsorbent): Trap temperature (adsorption temperature) -40℃, desorption temperature (desorption temperature) 0℃. Cold Tenax (registered trademark) Module 2 (Low Temperature Tenax Module 2) (Tenax TA Trap: a ceramic-coated trap filled with weakly polar porous polymer microspheres (Tenax TA) based on 2,6-diphenyl-p-phenylene oxide as the adsorbent) Temperature conditions: Trap temperature (adsorption temperature) -30℃, desorption temperature (desorption temperature) 200℃, Temperature conditions for Focusing Module 3 (Cryo focusing): trap temperature (adsorption temperature) -165℃, desorption temperature 100℃. Sample flow rate: 50 mL / min He flushing volume (helium flow rate): 75 mL Volume of M1 to M2 (flow rate of module 1 to module 2): 40 mL (100 mL / min). Time from M2 to M3 (Time from Module 2 to Module 3): 3.0 minutes. Injection time: 0.3 minutes. M1, M2, and M3 correspond to modules 1, 2, and 3 above, respectively. "M1 to M2" and "M2 to M3" indicate the conditions for sample flow between modules.

[0039] -Gas Chromatography- The gas chromatographic determination conditions for separating the volatile organic compounds (vapors) concentrated by the automatic concentration device are as follows. Analytical column: A column with a length of 60 m and an inner diameter of 320 μm, consisting of a stationary phase of dimethylpolysiloxane with a film thickness of 1 μm. Temperature program: Hold at 35°C for 2 minutes, then increase the temperature at 10°C / minute until reaching 240°C, then hold for 7 minutes and 30 seconds. Sample introduction temperature: 220℃ Carrier gas: Helium Flow split ratio: 0.667:1 Control mode: Constant pressure (153.09 kPa) After being separated by an analytical column, the concentrated sample was sent to an odor detection system and a mass spectrometer at a 1:1 ratio.

[0040] As the measuring device used in the gas chromatograph, the Agilent 7890B gas chromatograph system manufactured by Agilent Technologies is preferred. The analytical column can be, for example, the "DB-1" (part number: 123-1063) manufactured by Agilent Technologies.

[0041] Mass spectrometer The measurement conditions for mass spectrometry are as follows. Ionization mode: EI Measurement type: Scan Ion source temperature: 250℃ Quadrupole temperature: 150℃ Electron energy: 70.0 eV Scan start quality: 30 Finished scan quality: 400 Calibration curve: A calibration curve was constructed using the peak area of ​​deuterated toluene (EIC: m / z 98.000) as a linear function passing through the origin, using deuterated toluene standard gas (concentration: 10 ppb, dilution gas: nitrogen). Extrapolation was performed for calculations even outside the range of the calibration curve in the analysis of the samples.

[0042] During data analysis, extracted ion chromatography (EIC) was used to confirm the EIC peak area (EIC: m / z) of 4,4-dimethyl-2-pentanone appearing at the relative retention times shown in Table 1 when the relative retention time of deuterated toluene was set to 1.0. Furthermore, for the peak of 4,4-dimethyl-2-pentanone, the relative retention time and mass spectrometry were confirmed beforehand using various reagents for identification.

[0043] [Table 1]

[0044] As for the mass spectrometer used in the mass spectrometry analysis, the Agilent 5977B MSD manufactured by Agilent Technologies is preferred.

[0045] In calculating the deuterated toluene equivalent concentration of 4,4-dimethyl-2-pentanone in the vapor of the 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. Ideally, a calibration curve should be prepared for each measurement. Furthermore, in cases where multiple peaks exist within the relative retention times shown in Table 1, peak areas other than those previously identified are excluded from the calculation. Additionally, the deuterated toluene equivalent concentration of 4,4-dimethyl-2-pentanone contained in the analytical environment is analyzed, and each concentration is calculated as a difference.

[0046] (Composition for cosmetic raw materials) The cosmetic ingredient composition comprises a 3,5,5-trimethylhexanoic acid composition and may also contain other ingredients. The 3,5,5-trimethylhexanoic acid composition is as described in the above-mentioned "3,5,5-trimethylhexanoic acid composition".

[0047] The cosmetic ingredient 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] (Composition for refrigeration oil raw materials) The composition for use as raw material for refrigeration oil includes a 3,5,5-trimethylhexanoic acid composition and may also include other components. The 3,5,5-trimethylhexanoic acid composition is as described above in "(3,5,5-trimethylhexanoic acid composition)".

[0049] The composition for use as a raw material for refrigeration oil can be incorporated into the refrigeration oil composition after the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition has been derivatized.

[0050] (Odor Suppression Methods) The odor suppression method is a method for suppressing odors in a 3,5,5-trimethylhexanoic acid composition. The odor suppression method includes a formic acid concentration adjustment step, and may also include other steps.

[0051] -Formic acid concentration adjustment process- The formic acid concentration adjustment process is as follows: in the 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid, the formic acid concentration as a trace component, as determined by liquid chromatography under the following measurement conditions, is adjusted to be greater than 0 ppm by mass and less than 25 ppm by mass. The 3,5,5-trimethylhexanoic acid composition is as described above in "(3,5,5-trimethylhexanoic acid composition)". (Measurement conditions) Column: A packed column for reversed-phase chromatography, 25 cm in length and 4.6 mm in inner diameter. The stationary phase of the analytical column (gel particles packed into the column): octadecyl groups were introduced into the surface in a monolayer, with a particle size of 5 μm, a pore size of 100 Å, and a specific 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 phases: Mobile phase A 0.1% by mass phosphoric acid aqueous solution, Mobile phase B acetonitrile Gradient conditions: Adjust the ratio of mobile phase A to mobile phase B according to the analysis time as follows. 0-15 minute moving phase A100% The phase transitions linearly from 100% moving phase A to 100% moving phase B within 15-25 minutes. 25-30 minute moving phase B100% The phase transitions linearly from 100% moving phase B to 100% moving phase A within 30-40 minutes. 40-60 minute moving phase A100% Mobile phase flow rate: 1.0 mL / min Column oven temperature: 40℃ Detector: UV detector Wavelength used: 210nm Sample injection method: using an autosampler Sample injection volume: 10.0 μL Sample diluted or not: used undiluted Calibration curve: Perform at least three analyses on a sample with a known formic acid concentration, and construct a calibration curve using the peak areas of the formic acid components.

[0052] There are no particular restrictions on the method for adjusting the formic acid concentration in the formic acid concentration adjustment process, and it can be appropriately selected according to the purpose. Examples include adding formic acid. There are no particular limitations on the method of adding formic acid, and it can be appropriately selected according to the purpose.

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

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

[0055] (Method for manufacturing cosmetic composition) The method for manufacturing the cosmetic composition is a method of manufacturing a cosmetic composition using the 3,5,5-trimethylhexanoic acid composition. The method for manufacturing 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 also 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 the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition has been derivatized.

[0057] There are no particular limitations on the derivatization method, and it can be appropriately selected according to the purpose. For example, esterification of carboxylic acids containing 3,5,5-trimethylhexanoic acid and hydroxyl-containing compounds can be mentioned. One hydroxyl-containing compound can be used alone, or two or more can be used together. Furthermore, when performing the esterification, etc., carboxyl-containing compounds other than 3,5,5-trimethylhexanoic acid can also be used together.

[0058] Derivatives of 3,5,5-trimethylhexanoic acid in the cosmetic composition include, for example, hexadecyl isononanoate, butylene glycol diisononanoate, octyl isononanoate, isodecyl isononanoate, isononyl isononanoate, cetearyl isononanoate, tridecyl isononanoate, isostearyl isononanoate, isotraceneyl isononanoate, ethylhexyl isononanoate, tricyclodecanemethyl isononanoate, diethylene glycol diisononanoate, neopentyl glycol diisononanoate, pentaerythritol tetraisononanoate, polyglycerol-20 octaisononanoate, dipentaerythritol hexaisononanoate, dipentaerythritol pentaisononanoate, diethylene glycol di(ethylhexanoate / isononanoate), (polyglycerol-2 isononanoate / dimeric linoleic acid) copolymer, (trimethylpentanediol / adipic acid / isononanoic acid) copolymer, etc.

[0059] (Method for manufacturing refrigeration oil composition) The method for manufacturing the refrigeration oil composition is a method of manufacturing the refrigeration oil composition using the 3,5,5-trimethylhexanoic acid composition. The method for manufacturing 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 also 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 the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition has been derivatized.

[0061] There are no particular limitations on the derivatization method, and it can be appropriately selected according to the purpose. For example, esterification of carboxylic acids containing 3,5,5-trimethylhexanoic acid and hydroxyl-containing compounds can be mentioned. One hydroxyl-containing compound can be used alone, or two or more can be used together. Furthermore, when performing the esterification, etc., carboxyl-containing compounds other than 3,5,5-trimethylhexanoic acid can also be used together.

[0062] As derivatives of 3,5,5-trimethylhexanoic acid in the aforementioned refrigeration oil composition, examples include esters of carboxylic acids and polyols containing 3,5,5-trimethylhexanoic acid.

[0063] Examples of such polyols include ethylene glycol, 1,3-propanediol, propylene glycol, 1,2-butanediol, 1,4-butanediol, 1,5-pentanediol, 2-methyl-1,3-propanediol, neopentanediol, 1,6-hexanediol, 1,7-heptanediol, 2-ethyl-2-methyl-1,3-propanediol, 1,8-octanediol, 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, glycerol, 1,3,5-pentanetriol, trimethylolethane, trimethylolpropane, trimethylolbutane, and 3-hydroxy-2-propanediol. 2-Dimethylpropyl-3-hydroxy-2,2-dimethylpropionate, pentaerythritol, polyglycerol (2-20 polymers of glycerol), di(trimethylolpropane), dipentaerythritol, tripentaerythritol, di(trimethylolpropane), tri(trimethylolpropane), dipentaerythritol, di(pentaerythritol), tri(pentaerythritol), sorbitol, sorbitol anhydride, sorbitol glycerol condensate, ribitol, arabinitol, xylitol, mannitol and other sugar alcohols, xylose, arabinose, ribose, rhamnose, glucose, fructose, galactose, mannose, sorbitol, cellobiose, maltose, isomaltose, trehalose, sucrose, raffinose, gentiotriose, mesotriose and other sugars, as well as some of their etherifications, methyl glucosides (glycosides), etc. The polyol can be used alone or in combination with two or more.

[0064] Esters containing carboxylic acids and polyols of the aforementioned 3,5,5-trimethylhexanoic acid can combine carboxylic acids other than 3,5,5-trimethylhexanoic acid. Examples of carboxylic acids other than 3,5,5-trimethylhexanoic acid include, for example, butyric acid, valeric 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-dimethylpropionic acid, 2-ethylbutyric acid, 2-methylvaleric acid, 4-methylvaleric acid, 2-methylhexanoic acid, 2-ethylvaleric acid, 2-ethyl-2-methylbutyric acid, 2,2-dimethylvaleric acid, 2-methylheptanoic acid, 2-ethylhexanoic acid, 3-ethylhexanoic acid, 2-ethyl-2-methylvaleric acid, 2-ethyl-4-methylvaleric acid, 2,2-dimethylheptanoic acid, isodecanoic acid, isotriadecanoic acid, spermicidal acid, myristoleic acid, palmitoleic acid, heptadecanoic acid, octadecanoic acid, etc. Straight-chain or branched aliphatic monocarboxylic acids such as carboxylic acid, trans-oleic acid, oleic acid, isoleic acid, linoleic acid, trans-linoleic acid, hexadecanetrienoic acid, linolenic acid, and arachidonic acid; oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, octanoic acid, azelaic acid, sebacic acid, methylmalonic acid, ethylmalonic acid, dimethylmalonic acid, methylsuccinic acid, 2,2-dimethylsuccinic acid, 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, mesocarboxylic acid, 1,2-cyclohexanedicarboxylic acid, 4-cyclohexene-1,2-dicarboxylic acid, phthalic acid, terephthalic acid, isophthalic acid, trimellitic acid, and pyromellitic acid, etc. The carboxylic acids other than 3,5,5-trimethylhexanoic acid may be used alone or in combination. Example

[0065] The following describes embodiments of the present invention, but the present invention is not limited 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 hydroformylation of diisobutylene and carbonyl syngas, followed by oxidation to obtain crude 3,5,5-trimethylhexanoic acid.

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

[0068] (Example 1) The purified 3,5,5-trimethylhexanoic acid obtained in Comparative Example 1 (89.90 g) and formic acid (Fujifilm and Kohden Chemical Co., Ltd., reagent grade, purity 89.4%) (0.10 g) were mixed to obtain a mixture. Furthermore, 89.64 g of purified 3,5,5-trimethylhexanoic acid obtained in Comparative Example 1 and 0.36 g of the mixture were mixed to obtain a 3,5,5-trimethylhexanoic acid composition containing 4.0 ppm formic acid by mass.

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

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

[0071] (Example 4) 88.187 g of purified 3,5,5-trimethylhexanoic acid obtained by the same method as 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 formic acid by mass.

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

[0073] <Analysis 1 (Gas Chromatography)> Gas 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. The concentration of 3,5,5-trimethylhexanoic acid was calculated as the area ratio (%) of the peak of 3,5,5-trimethylhexanoic acid relative to the area of ​​all peaks. The results are shown in Table 2.

[0074] -Gas Chromatography Analysis Conditions- (Measurement conditions) Apparatus: Gas Chromatograph 2010 Plus manufactured by Shimadzu Corporation Analytical column: Agilent Technologies "DB-FFAP" (a 30m long, 0.25mm inner diameter column containing a 0.25μm thick high-polarity polyethylene glycol stationary phase) (part number: 122-3232). Temperature program: Hold at 80℃ for 1 minute, then increase the temperature at 10℃ / minute until reaching 210℃, then hold 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℃ Control mode: Constant linear velocity mode Flow split ratio: 50:1 Sample injection conditions: 0.5 μL

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

[0076] -Liquid Chromatography Analysis Conditions- Device: LC-2050C-3D manufactured by Shimadzu Corporation Analytical column: TSKgel ODS-100V 5μm (inner diameter 4.6mm, length 25cm) manufactured by Tosoh Corporation. Mobile phases: Mobile phase A 0.1% by mass phosphoric acid aqueous solution, Mobile phase B acetonitrile Gradient conditions: Adjust the ratio of mobile phase A to mobile phase B according to the analysis time as follows. 0-15 minute moving phase A100% The phase transitions linearly from 100% moving phase A to 100% moving phase B within 15-25 minutes. 25-30 minute moving phase B100% The phase transitions linearly from 100% moving phase B to 100% moving phase A within 30-40 minutes. 40-60 minute moving phase A100% Mobile phase flow rate: 1.0 mL / min Column oven temperature: 40℃ Detector: UV detector Wavelength used: 210nm Sample injection method: using an autosampler Sample injection volume: 10.0 μL Sample diluted or not: used undiluted Calibration curve: The formic acid was diluted with ion-exchanged water (Fujifilm and Kazuko Pure Chemicals Co., Ltd., reagent grade, purity 89.4%) and the concentration of formic acid was adjusted to 1 ppm, 10 ppm, 20 ppm and 40 ppm by mass. The peak area of ​​formic acid was used to prepare the calibration curve.

[0077] [Table 2]

[0078] <Storage Stability Test> 10 g of 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 under air atmosphere and sealed, then placed in a constant temperature bath maintained at 80°C. After one week from the time of placement in the constant temperature bath, the 3,5,5-trimethylhexanoic acid or 3,5,5-trimethylhexanoic acid compositions were removed. For the 3,5,5-trimethylhexanoic acid or 3,5,5-trimethylhexanoic acid compositions after the preservation stability test, odor identification gas chromatography / mass spectrometry analysis was performed under the conditions described below. The conditions for the storage stability test refer to the accelerated conditions used to prepare a state for long-term storage of 3,5,5-trimethylhexanoic acid or a 3,5,5-trimethylhexanoic acid composition.

[0079] <Analysis 3 (Odor Identification Gas Chromatography / Mass Spectrometry Analysis)> For the 3,5,5-trimethylhexanoic acid or 3,5,5-trimethylhexanoic acid compositions obtained in Examples 1-4 and Comparative Examples 1-2 after the storage stability test, the concentration of 4,4-dimethyl-2-pentanone after the storage stability test was determined by odor-based gas chromatography / mass spectrometry analysis according to the following method. In addition, odor identification gas chromatography / mass spectrometry analysis is used. Figure 1The apparatus is shown in the schematic diagram. It comprises a concentration unit, a gas chromatograph, an odor detection system, and a mass spectrometer. The concentration unit draws in the gas phase of the sample packed into a container, removes H2O, N2, O2, and CO2, and concentrates the remaining volatile organic compounds. The gas chromatograph separates the concentrated volatile organic compounds using a capillary column. The odor detection system can directly detect the separated components. The mass spectrometer performs qualitative and quantitative analysis of the separated components.

[0080] - Sample concentration - 5.0 g of the obtained 3,5,5-trimethylhexanoic acid composition was filled into a 500 mL sealable container, and after standing at 30°C for more than 20 minutes, 200 mL of the gas phase was aspirated and introduced into an automatic concentration device. Automatic Concentrator: Entech 7200 Automatic Concentrator manufactured by ENTECH INSTRUMENTS Sample size: 5.0g Container capacity: 500mL Injection volume: 200 mL for the gas phase and 100 mL for the internal standard separated from the gas phase. Internal standard: Deuterated toluene standard gas (concentration 10 ppb / v, dilution gas: nitrogen, Sumitomo Seikan Corporation) Concentration method: CTD mode (cold trap dehydration) Temperature conditions for dehydration module 1 (Empty Trap: a ceramic-coated trap without adsorbent): Trap temperature -40℃, desorption temperature 0℃ Cold Tenax (registered trademark) Module 2 (Tenax TA Trap: a ceramic-coated trap filled with weakly polar porous polymer microspheres (Tenax TA) based on 2,6-diphenyl-p-phenylene oxide as an adsorbent) Temperature conditions: Trap temperature -30°C, desorption temperature 200°C Temperature conditions for Cryo focusing module 3: trap temperature -165℃, desorption temperature 100℃ Sample flow rate: 50 mL / min He rinse volume: 75mL Volume from M1 to M2: 40 mL (100 mL / min) Time from M2 to M3: 3.0 minutes Injection time: 0.3 minutes

[0081] -Gas Chromatography- Measurement equipment: Agilent 7890B gas chromatograph system manufactured by Agilent Technologies. Analytical column: DB-1 (part number: 123-1063) manufactured by Agilent Technologies (a 60m long × 320μm inner diameter column with a 1μm thick dimethylpolysiloxane stationary phase). Temperature program: Hold at 35°C for 2 minutes, then increase the temperature at a rate of 10°C / minute until reaching 240°C, then hold for 7 minutes and 30 seconds. Sample introduction temperature: 220℃ Carrier gas: Helium Flow split ratio: 0.667:1 Control mode: Constant pressure (153.09 kPa) After being separated by a capillary column, the concentrated sample was sent to an odor detection system and a mass spectrometer at 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 Scan start quality: 30 Finished scan quality: 400 Calibration curve: Using deuterated toluene standard gas (concentration: 10 ppb, dilution gas: nitrogen) manufactured by Sumitomo Seikan Co., Ltd., the peak area of ​​deuterated toluene (EIC: m / z 98.000) was measured with injection volumes of 50 mL, 100 mL, 150 mL, and 200 mL. Using the same injection volume of 200 mL as the sample determination as a baseline, the determinations at injection volumes of 50 mL, 100 mL, and 150 mL were considered equivalent to determinations of deuterated toluene concentrations of 2.5 ppb, 5.0 ppb, and 7.5 ppb, respectively, based on volume ratios. A linear function calibration curve passing through the origin was constructed. Extrapolation was performed even outside the range of the calibration curve for the sample analysis.

[0083] During data analysis, extracted ion chromatography (EIC) was used to confirm the EIC peak area (EIC: m / z) of 4,4-dimethyl-2-pentanone appearing at the relative retention times shown in Table 3 when the relative retention time of deuterated toluene was set to 1.0. Furthermore, for the peak of 4,4-dimethyl-2-pentanone, the relative retention time and mass spectra were confirmed and identified beforehand using various reagents.

[0084] [Table 3]

[0085] In calculating the deuterated toluene equivalent concentration of 4,4-dimethyl-2-pentanone in the vapor of 3,5,5-trimethylhexanoic acid or a combination thereof, 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 (EIC: m / z 98.000), and the calculation is 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 environment was analyzed with a sample weight of 0 g, and the differences were used to calculate each concentration. The results are shown in Table 2. [Mathematical Expression 1] The equivalent concentration (volume ppb) of deuterated toluene is 5.84 × 10⁻⁶. -6 ×EIC peak area of ​​the compound (Equation 1)

[0086] <Odor Evaluation> After the stability test, 10g of 3,5,5-trimethylhexanoic acid or 3,5,5-trimethylhexanoic acid composition obtained in Examples 1-4 and Comparative Examples 1-2 were placed into 20mL wide-mouth bottles, capped, and left to stand at room temperature for 30 minutes. Afterwards, the lid was opened, and three evaluators assessed the odor based on the following evaluation criteria. The results are shown in Table 2 (average of 3 evaluators).

[0087] -Evaluation Criteria- 1: Smells like sewer 2: A slight stench, like that of a sewer. 3: It doesn't smell like sewage.

[0088] According to the results in Table 2, an odor-suppressing 3,5,5-trimethylhexanoic acid composition was obtained by using 3,5,5-trimethylhexanoic acid and a 3,5,5-trimethylhexanoic acid composition containing more than 0 ppm by mass and less than 25 ppm by mass of formic acid.

[0089] As an example of the present invention, the following methods may be cited. <1> A 3,5,5-trimethylhexanoic acid composition, characterized in that, The formic acid, comprising 3,5,5-trimethylhexanoic acid and formic acid as a trace component, is determined under the following conditions, based on liquid chromatography analysis, to have a concentration of 0 ppm by mass or less than 25 ppm by mass. (Measurement conditions) Column: A packed column for reversed-phase chromatography, 25 cm in length and 4.6 mm in inner diameter. The columns are as follows: The stationary phase of the analytical column was a monolayer of octadecyl groups introduced onto its surface, with a particle size of 5 μm, a pore size of 100 Å, and a specific surface area of ​​450 m². 2 Silica gel particles with a density of 1.10 mL / g, a micropore capacity of 1.10 mL / g, and a carbon content of 15%. Mobile phases: Mobile phase A 0.1% by mass phosphoric acid aqueous solution, Mobile phase B acetonitrile. Gradient conditions: Adjust the ratio of mobile phase A to mobile phase B according to the analysis time as follows. 0-15 minutes moving phase A100%, The phase transitions linearly from 100% A to 100% B over 15-25 minutes. 25-30 minutes moving phase B100%, The phase changes linearly from 100% B to 100% A over 30-40 minutes. 40-60 minutes moving phase A100%, Mobile phase flow rate: 1.0 mL / min Column oven temperature: 40℃ Detector: UV detector Wavelength used: 210nm Sample injection method: Use an autosampler. Sample injection volume: 10.0 μL Sample diluted or not: Used undiluted. Calibration curve: Perform analysis at more than 3 points on a sample with a known concentration of formic acid, and use the peak area of ​​formic acid to create a calibration curve. <2> The 3,5,5-trimethylhexanoic acid composition according to <1> above, wherein, The concentration of formic acid is above 0.10 ppm by mass and below 22 ppm by mass. <3> The 3,5,5-trimethylhexanoic acid composition according to <1> above, wherein it contains 4,4-dimethyl-2-pentanone as a trace component, wherein the deuterated toluene equivalent concentration of the 4,4-dimethyl-2-pentanone, determined by odor-based gas chromatography / mass spectrometry analysis under the following test conditions, is 5.0 v / v ppb or more and 50 v / v ppb or less. (Measurement conditions) -concentrate- Automatic concentration apparatus: A concentration apparatus comprising a device for attracting the gas phase section of a container holding organic compounds, module 1, module 2, and module 3. Module 1 is a ceramic-coated trap unfilled with an adsorbent for removing moisture from the gas phase. Module 2 is a ceramic-coated trap filled with weakly polar porous polymer microspheres based on 2,6-diphenyl-p-phenylene oxide as an adsorbent for adsorbing the gas phase after moisture removal and removing nitrogen, oxygen, carbon dioxide, and methane. Module 3 is a rapid heater for adsorbing the gas phase desorbed from the trap, followed by rapid heating to desorb it, thereby introducing it into a gas chromatograph. Sample size: 5.0g Injection volume: 200 mL of the sample gas phase and 100 mL of an additional internal standard in a container that has been left to stand at 30°C for at least 20 minutes. Internal standard: deuterated toluene standard gas (concentration 10 ppb / v, dilution gas is nitrogen). Concentration method: Temperature conditions for module 1: adsorption temperature -40℃, desorption temperature 0℃. Temperature conditions for module 2: adsorption temperature -30℃, desorption temperature 200℃. Temperature conditions for module 3: adsorption temperature -165℃, desorption temperature 100℃. The flow rate of the sample's gas phase components through modules 1 and 2 is 50 mL / min. The components in the gas phase are adsorbed into module 2 and used to remove the remaining helium. Flow rate: 75 mL. The helium flow rate (rate) used to transfer components desorbed from the gas phase of module 1 to module 2 is 40 mL (100 mL / min). Time required to transfer components desorbed from the gas phase of module 2 to module 3: 3.0 minutes. The desorption time for introducing components adsorbed in the gas phase section of module 3 into the gas chromatograph is 0.3 minutes. -Gas Chromatography- Analytical column: A column with a length of 60 m and an inner diameter of 320 μm, consisting of a stationary phase of dimethylpolysiloxane with a film thickness of 1 μm. Temperature program: Hold at 35℃ for 2 minutes, then increase the temperature at 10℃ / minute until reaching 240℃, then hold for 7 minutes and 30 seconds. Sample introduction temperature: 220℃ Carrier gas: Helium Flow split ratio: 0.667:1 Control mode: After concentration at constant pressure (153.09 kPa), the sample was separated by a capillary column and then sent to the odor detection system and mass spectrometer at a 1:1 ratio. -Mass Spectrometry Analysis- Ionization mode: EI Measurement type: Scan, Ion source temperature: 250℃ Quadrupole temperature: 150℃ Electron energy: 70.0 eV Scan start quality: 30 Finished scan quality: 400 Calibration curve: A calibration curve was constructed using the peak area of ​​deuterated toluene (EIC: m / z 98.000) as a linear function passing through the origin, using deuterated toluene standard gas (concentration: 10 ppb, dilution gas: nitrogen). Data analysis: Using extracted ion chromatograms (EIC), the EIC peak area (EIC: m / z 114.000) of 4,4-dimethyl-2-pentanone appearing within the relative retention time range of 0.99 to 1.05 when the relative retention time of deuterated toluene was set to 1.0 was used to calculate the converted concentration of deuterated toluene based on the calibration curve described above. <4> The 3,5,5-trimethylhexanoic acid composition according to <3> above, wherein, The conditions for concentration are as follows: Automatic concentration unit: Entech 7200 automatic concentration unit manufactured by ENTECH INSTRUMENTS. Sample size: 5.0g Injection volume: 200 mL of the sample gas phase and 100 mL of an additional internal standard in a container that has been left to stand at 30°C for at least 20 minutes. Internal standard: deuterated toluene standard gas (concentration 10 ppb / v, dilution gas is nitrogen). Concentration method: CTD mode (cold trap dehydration). Temperature conditions for dehydration module 1 (Empty Trap: a ceramic-coated trap without adsorbent): trap temperature -40℃, desorption temperature 0℃. Temperature conditions for Cold Tenax Module 2 (Tenax TA Trap: a ceramic-coated trap filled with weakly polar porous polymer microspheres based on 2,6-diphenyl-p-phenylene oxide as an adsorbent): trap temperature -30°C, desorption temperature 200°C. Temperature conditions for Cryo focusing module 3: trap temperature -165℃, desorption temperature 100℃. Sample flow rate: 50 mL / min He rinse volume: 75 mL Volume of M1 to M2: 40 mL (100 mL / min). Time from M2 to M3: 3.0 minutes Injection time: 0.3 minutes The analytical apparatus used in the gas chromatography was an Agilent 7890B gas chromatography system manufactured by Agilent Technologies. The measuring instrument used in the mass spectrometry analysis was an Agilent 5977B MSD manufactured by Agilent Technologies. <5> A composition for use as a cosmetic ingredient, characterized in that, Compositions comprising any one of <1> to <4> above, including 3,5,5-trimethylhexanoic acid. <6> A composition for use as a raw material in refrigeration oil, characterized in that, Compositions comprising any one of <1> to <4> above, including 3,5,5-trimethylhexanoic acid. <7> A method for odor suppression in a 3,5,5-trimethylhexanoic acid composition, characterized in that, The process includes a formic acid concentration adjustment step, in which the formic acid concentration, as a trace component determined by liquid chromatography under the following measurement conditions, is adjusted to be greater than 0 ppm by mass and less than 25 ppm by mass in the 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid. (Measurement conditions) Column: A packed column for reversed-phase chromatography, 25 cm in length and 4.6 mm in inner diameter. The stationary phase of the analytical column was a monolayer of octadecyl groups introduced onto its surface, with a particle size of 5 μm, a pore size of 100 Å, and a specific surface area of ​​450 m². 2 Silica gel particles with a density of 1.10 mL / g, a micropore capacity of 1.10 mL / g, and a carbon content of 15%. Mobile phases: Mobile phase A 0.1% by mass phosphoric acid aqueous solution, Mobile phase B acetonitrile. Gradient conditions: Adjust the ratio of mobile phase A to mobile phase B according to the analysis time as follows. 0-15 minutes moving phase A100%, The phase transitions linearly from 100% A to 100% B over 15-25 minutes. 25-30 minutes moving phase B100%, The phase changes linearly from 100% B to 100% A over 30-40 minutes. 40-60 minutes moving phase A100%, Mobile phase flow rate: 1.0 mL / min Column oven temperature: 40℃ Detector: UV detector Wavelength used: 210nm Sample injection method: Use an autosampler. Sample injection volume: 10.0 μL Sample diluted or not: Used undiluted. Calibration curve: Perform at least three analyses on a sample with a known formic acid concentration, and construct a calibration curve using the peak areas of the formic acid components. <8> A method for manufacturing a low-odor 3,5,5-trimethylhexanoic acid composition, characterized in that, The process includes a formic acid concentration adjustment step, in which the formic acid concentration, as a trace component determined by liquid chromatography under the following measurement conditions, is adjusted to be greater than 0 ppm by mass and less than 25 ppm by mass in the 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid. (Measurement conditions) Column: A packed column for reversed-phase chromatography, 25 cm in length and 4.6 mm in inner diameter. The stationary phase of the analytical column was a monolayer of octadecyl groups introduced onto its surface, with a particle size of 5 μm, a pore size of 100 Å, and a specific surface area of ​​450 m². 2 Silica gel particles with a density of 1.10 mL / g, a micropore capacity of 1.10 mL / g, and a carbon content of 15%. Mobile phases: Mobile phase A 0.1% by mass phosphoric acid aqueous solution, Mobile phase B acetonitrile. Gradient conditions: Adjust the ratio of mobile phase A to mobile phase B according to the analysis time as follows. 0-15 minutes moving phase A100%, The phase transitions linearly from 100% A to 100% B over 15-25 minutes. 25-30 minutes moving phase B100%, The phase changes linearly from 100% B to 100% A over 30-40 minutes. 40-60 minutes moving phase A100%, Mobile phase flow rate: 1.0 mL / min Column oven temperature: 40℃ Detector: UV detector Wavelength used: 210nm Sample injection method: Use an autosampler. Sample injection volume: 10.0 μL Sample diluted or not: Used undiluted. Calibration curve: Perform analysis at more than 3 points on a sample with a known concentration of formic acid, and use the peak area of ​​formic acid to create a calibration curve. <9> A method for manufacturing a cosmetic composition, comprising using the 3,5,5-trimethylhexanoic acid composition described in any one of <1> to <4> above to manufacture the cosmetic composition, characterized in that, The process includes the derivatization of the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition. <10> A method for manufacturing a refrigeration oil composition, wherein the refrigeration oil composition is manufactured using the 3,5,5-trimethylhexanoic acid composition described in any one of <1> to <4> above, characterized in that... The process includes the derivatization of the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition.

Claims

1. A 3,5,5-trimethylhexanoic acid composition, characterized in that, It contains 3,5,5-trimethylhexanoic acid and formic acid as a trace component. The concentration of formic acid, determined by liquid chromatography under the following conditions, is greater than 0 ppm by mass and less than 25 ppm by mass. (Measurement conditions) Column: A packed column for reversed-phase chromatography, 25 cm in length and 4.6 mm in inner diameter. The stationary phase of the analytical column was a monolayer of octadecyl groups introduced onto its surface, with a particle size of 5 μm, a pore size of 100 Å, and a specific surface area of ​​450 m². 2 Silica gel particles with a density of 1.10 mL / g, a micropore capacity of 1.10 mL / g, and a carbon content of 15%. Mobile phases: Mobile phase A 0.1% by mass phosphoric acid aqueous solution, Mobile phase B acetonitrile. Gradient condition: Adjust the ratio of mobile phase A to mobile phase B according to the analysis time as follows. 0-15 minutes moving phase A100%, The phase transitions linearly from 100% A to 100% B over 15-25 minutes. 25-30 minutes moving phase B100%, The phase changes linearly from 100% B to 100% A over 30-40 minutes. 40-60 minutes moving phase A100%, Mobile phase flow rate: 1.0 mL / min Column oven temperature: 40℃ Detector: UV detector Wavelength used: 210nm Sample injection method: Use an autosampler. Sample injection volume: 10.0 μL Sample diluted or not: Used undiluted. Calibration curve: Perform analysis at more than 3 points on a sample with a known concentration of formic acid, and use the peak area of ​​formic acid to create a calibration curve.

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

3. The 3,5,5-trimethylhexanoic acid composition according to claim 1, wherein, It contains 4,4-dimethyl-2-pentanone as a trace component. The deuterated toluene equivalent concentration of 4,4-dimethyl-2-pentanone, determined by odor-based gas chromatography / mass spectrometry analysis under the following conditions, is above 5.0 v / v ppb and below 50 v / v ppb. (Measurement conditions) -concentrate- Automatic concentration device: A concentration device comprising a device for attracting the gas phase section of a container holding organic compounds, module 1, module 2, and module 3. Module 1 is a ceramic-coated trap unfilled with an adsorbent for removing moisture from the gas phase. Module 2 is a ceramic-coated trap filled with weakly polar porous polymer microspheres based on 2,6-diphenyl-p-phenylene oxide as an adsorbent for adsorbing the gas phase after moisture removal and for removing nitrogen, oxygen, carbon dioxide, and methane. Module 3 is a rapid heater for adsorbing the gas phase desorbed from the trap, followed by rapid heating to desorb it, thereby introducing it into a gas chromatograph. Sample size: 5.0g Injection volume: 200 mL of the sample gas phase and 100 mL of an additional internal standard in a container that has been left to stand at 30°C for at least 20 minutes. Internal standard: deuterated toluene standard gas (concentration 10 ppb / v, dilution gas is nitrogen). Concentration method: Temperature conditions for module 1: adsorption temperature -40℃, desorption temperature 0℃. Temperature conditions for module 2: adsorption temperature -30℃, desorption temperature 200℃. Temperature conditions for module 3: adsorption temperature -165℃, desorption temperature 100℃. The components of the sample's gas phase are kept within the flow rate of module 1 and module 2 at a rate of 50 mL / min. The components in the gas phase are adsorbed into module 2 and used to remove the remaining helium. Flow rate: 75 mL. The helium flow rate (rate) used to transfer components desorbed from the gas phase of module 1 to module 2 is 40 mL (100 mL / min). Time required to transfer components desorbed from the gas phase of module 2 to module 3: 3.0 minutes. The desorption time for introducing components adsorbed in the gas phase section of module 3 into the gas chromatograph is 0.3 minutes. -Gas Chromatography- Analytical column: A column with a length of 60 m and an inner diameter of 320 μm, consisting of a stationary phase of dimethylpolysiloxane with a film thickness of 1 μm. Temperature program: Hold at 35℃ for 2 minutes, then increase the temperature at a rate of 10℃ / minute until reaching 240℃, then hold for 7 minutes and 30 seconds. Sample introduction temperature: 220℃ Carrier gas: Helium Flow split ratio: 0.667:1 Control mode: Constant pressure (153.09 kPa). After concentration, the sample was separated using a capillary column and then sent to an odor detection system and a mass spectrometer at a 1:1 ratio. -Mass Spectrometry Analysis- Ionization mode: EI Measurement type: Scan, Ion source temperature: 250℃ Quadrupole temperature: 150℃ Electron energy: 70.0 eV Scan start quality: 30 Finished scan quality: 400 Calibration curve: A calibration curve was constructed using the peak area of ​​deuterated toluene (EIC: m / z 98.000) as a linear function passing through the origin, using deuterated toluene standard gas (concentration: 10 ppb, dilution gas: nitrogen). Data analysis: Using extracted ion chromatograms (EIC), the EIC peak area (EIC: m / z 114.000) of 4,4-dimethyl-2-pentanone appearing within the relative retention time range of 0.99 to 1.05 when the relative retention time of deuterated toluene was set to 1.0 was used to calculate the converted concentration of deuterated toluene based on the calibration curve described above.

4. The 3,5,5-trimethylhexanoic acid composition according to claim 3, wherein, The conditions for concentration are as follows: Automatic concentration unit: Entech 7200 automatic concentration unit manufactured by ENTECH INSTRUMENTS. Sample size: 5.0g Injection volume: 200 mL of the sample gas phase and 100 mL of an additional internal standard in a container that has been left to stand at 30°C for at least 20 minutes. Internal standard: deuterated toluene standard gas (concentration 10 ppb / v, dilution gas is nitrogen). Concentration method: CTD mode (cold trap dehydration). Temperature conditions for dehydration module 1 (Empty Trap: a ceramic-coated trap without adsorbent): trap temperature -40℃, desorption temperature 0℃. Temperature conditions for Cold Tenax Module 2 (Tenax TA Trap: a ceramic-coated trap filled with weakly polar porous polymer microspheres based on 2,6-diphenyl-p-phenylene oxide as an adsorbent): trap temperature -30°C, desorption temperature 200°C. Temperature conditions for focusing module 3 (Cryo focusing): trap temperature -165℃, desorption temperature 100℃. Sample flow rate: 50 mL / min He rinse volume: 75 mL Volume of M1 to M2: 40 mL (100 mL / min). Time from M2 to M3: 3.0 minutes Injection time: 0.3 minutes The analytical apparatus used in the gas chromatography was an Agilent 7890B gas chromatography system manufactured by Agilent Technologies. The measuring instrument used in the mass spectrometry analysis was an Agilent 5977BMSD manufactured by Agilent Technologies.

5. A composition for use as a cosmetic ingredient, characterized in that, Compositions comprising 3,5,5-trimethylhexanoic acid as described in any one of claims 1 to 4.

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

7. A method for suppressing odor, characterized in that, The process includes a formic acid concentration adjustment step, in which the formic acid concentration, as a trace component determined by liquid chromatography under the following measurement conditions, is adjusted to be greater than 0 ppm by mass and less than 25 ppm by mass in the 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid. (Measurement conditions) Column: A packed column for reversed-phase chromatography, 25 cm in length and 4.6 mm in inner diameter. The stationary phase of the analytical column was a monolayer of octadecyl groups introduced onto its surface, with a particle size of 5 μm, a pore size of 100 Å, and a specific surface area of ​​450 m². 2 Silica gel particles with a density of 1.10 mL / g, a micropore capacity of 1.10 mL / g, and a carbon content of 15%. Mobile phases: Mobile phase A 0.1% by mass phosphoric acid aqueous solution, Mobile phase B acetonitrile. Gradient condition: Adjust the ratio of mobile phase A to mobile phase B according to the analysis time as follows. 0-15 minutes moving phase A100%, The phase transitions linearly from 100% A to 100% B over 15-25 minutes. 25-30 minutes moving phase B100%, The phase changes linearly from 100% B to 100% A over 30-40 minutes. 40-60 minutes moving phase A100%, Mobile phase flow rate: 1.0 mL / min Column oven temperature: 40℃ Detector: UV detector Wavelength used: 210nm Sample injection method: Use an autosampler. Sample injection volume: 10.0 μL Sample diluted or not: Used undiluted. Calibration curve: Perform analysis at more than 3 points on a sample with a known concentration of formic acid, and use the peak area of ​​formic acid to create a calibration curve.

8. A method for manufacturing a low-odor 3,5,5-trimethylhexanoic acid composition, characterized in that, The process includes a formic acid concentration adjustment step, in which the formic acid concentration, as a trace component determined by liquid chromatography under the following measurement conditions, is adjusted to be greater than 0 ppm by mass and less than 25 ppm by mass in the 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid. (Measurement conditions) Column: A packed column for reversed-phase chromatography, 25 cm in length and 4.6 mm in inner diameter. The stationary phase of the analytical column was a monolayer of octadecyl groups introduced onto its surface, with a particle size of 5 μm, a pore size of 100 Å, and a specific surface area of ​​450 m². 2 Silica gel particles with a density of 1.10 mL / g, a micropore capacity of 1.10 mL / g, and a carbon content of 15%. Mobile phases: Mobile phase A 0.1% by mass phosphoric acid aqueous solution, Mobile phase B acetonitrile. Gradient condition: Adjust the ratio of mobile phase A to mobile phase B according to the analysis time as follows. 0-15 minutes moving phase A100%, The phase transitions linearly from 100% A to 100% B over 15-25 minutes. 25-30 minutes moving phase B100%, The phase changes linearly from 100% B to 100% A over 30-40 minutes. 40-60 minutes moving phase A100%, Mobile phase flow rate: 1.0 mL / min Column oven temperature: 40℃ Detector: UV detector Wavelength used: 210nm Sample injection method: Use an autosampler. Sample injection volume: 10.0 μL Sample diluted or not: Used undiluted. Calibration curve: Perform analysis at more than 3 points on a sample with a known concentration of formic acid, and use the peak area of ​​formic acid to create a calibration curve.

9. A method for manufacturing a cosmetic composition, comprising using the 3,5,5-trimethylhexanoic acid composition according to any one of claims 1 to 4, characterized in that, The process includes the derivatization of the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition.

10. A method for manufacturing a refrigeration oil composition, comprising using the 3,5,5-trimethylhexanoic acid composition according to any one of claims 1 to 4 to manufacture the refrigeration oil composition, characterized in that, The process includes the derivatization of the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition.

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