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

This is a 3,5,5-trimethylhexanoic acid composition comprising 3,5,5-trimethylhexanoic acid and methacrolein as a trace component, wherein the deuterium-to-toluene concentration of methacrolein, as determined by olfactory gas chromatography / mass spectrometry, is 0.50 ppb by volume or more and 30 ppb by volume or less.

Description

Technical Field

[0001] The present invention relates to a 3,5,5-trimethylhexanoic acid composition, 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.

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, refrigeration machine oil raw materials, metal processing oils, etc. Cosmetics, refrigeration machine oils, and metal processing oils are required to have low odor for their 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 excellent in sulfuric acid coloring evaluation has been known (Patent Document 2), but odor has still been an issue in the 3,5,5-trimethylhexanoic acid composition.

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 a trace amount of methacrolein. The 3,5,5-trimethylhexanoic acid composition is characterized in that the deuterium-to-toluene concentration of the methacrolein, measured by olfactory gas chromatography / mass spectrometry under the measurement conditions described below, is between 0.50 volume ppb and 30 volume ppb. <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 method for suppressing odor in a 3,5,5-trimethylhexanoic acid composition is characterized by including a methacrolein concentration adjustment step, in which the concentration of methacrolein as a trace component, measured by odor olfactory gas chromatography / mass spectrometry under the measurement conditions described below, is adjusted to be between 0.50 volume ppb and 30 volume ppb. <5> A method for producing a low-odor 3,5,5-trimethylhexanoic acid composition, characterized by including a methacrolein concentration adjustment step, in which the concentration of methacrolein as a trace component, measured by odor gas chromatography / mass spectrometry under the measurement conditions described below, is adjusted to be between 0.50 volume ppb and 30 volume ppb. <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 above, 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 methacrolein as a trace component, and may further contain other components.

[0011] -3,5,5-trimethylhexanoic acid- The aforementioned 3,5,5-trimethylhexanoic acid has the molecular formula C9H 18 O 2、 It is a compound represented by the structural formula (CH3)3CCH2CH(CH3)CH2COOH and has a molecular weight of 158.24. The aforementioned 3,5,5-trimethylhexanoic acid is sometimes also called isononanoic acid.

[0012] In the 3,5,5-trimethylhexanoic acid composition, there are no particular restrictions on the concentration (purity) of the 3,5,5-trimethylhexanoic acid, and it can be appropriately selected depending on the purpose, but 95.0% or higher is preferred, 97.0% or higher is more preferred, 98.5% or higher is even more preferred, and 99.0% or higher is particularly preferred.

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

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

[0015] For example, a gas chromatography apparatus such as the "Gas Chromatography 2010 Plus" manufactured by Shimadzu Corporation can be used. For gas chromatography, a column such as Agilent Technologies' "DB-FFAP" (part number: 122-3232) can be used. The measurement conditions for gas chromatography are as follows: (Measurement conditions) Analysis column: A column with a length of 30 m × inner diameter of 0.25 mm, where the stationary phase contains 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. After reaching 210 °C, hold for 26 minutes Sample introduction temperature: 250 °C Carrier gas: Nitrogen Gas flow rate of the column: 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 condition: 0.5 μL

[0016] -Methacrolein- The methacrolein is a compound represented by the molecular formula C4H6O, the structural formula CH2=C(CH3)CHO, and has a molecular weight of 70.09 The methacrolein may also be referred to as methacrylaldehyde or 2-methyl-2-propenal

[0017] In the 3,5,5-trimethylhexanoic acid composition, the concentration of the methacrolein is measured as the concentration in terms of heavy toluene by the method described in <Gas Chromatography / Mass Spectrometry for Odor Analysis> described below

[0018] As the lower limit value of the concentration of the methacrolein in terms of heavy toluene, there is no particular limitation as long as it is 0.50 volume ppb or more, and it can be appropriately selected according to the purpose. However, 1.0 volume ppb or more is preferred, 2.0 volume ppb or more is more preferred, 3.0 volume ppb or more is further preferred, and 4.0 volume ppb or more is particularly preferred As the upper limit value of the concentration of the methacrolein in terms of heavy toluene, there is no particular limitation as long as it is 30 volume ppb or less, and it can be appropriately selected according to the purpose. However, 25 volume ppb or less is preferred, 20 volume ppb or less is more preferred, 19 volume ppb or less is further preferred, 18 volume ppb or less is particularly preferred, and 15 volume ppb or less is most preferred 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 1.0 ppb to 25 ppb is preferred, 2.0 ppb to 20 ppb is more preferred, 2.0 ppb to 19 ppb is even more preferred, 3.0 ppb to 18 ppb is particularly preferred, and 4.0 ppb to 15 ppb is most preferred.

[0019] There are no particular restrictions on the timing of measuring the concentration of methacrolein in terms of deuterated toluene, and it can be appropriately selected depending on the purpose.

[0020] -Other ingredients- The other components mentioned above are not particularly limited and can be selected as appropriate depending on the purpose.

[0021] -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 that includes a synthesis step, a purification step, and a methacrolein concentration adjustment step.

[0022] --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.

[0023] 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.

[0024] --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.

[0025] --- 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.

[0026] --Methacrolein concentration adjustment process-- The aforementioned methacrolein concentration adjustment step is a step in which, in a 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid, the concentration of methacrolein as a trace component, measured by olfactory gas chromatography / mass spectrometry under the measurement conditions described later, is adjusted to be between 0.50 volume ppb and 30 volume ppb.

[0027] In the aforementioned methacrolein concentration adjustment step, there are no particular restrictions on the method of adjusting the concentration, and it can be appropriately selected depending on the purpose, but examples include adding methacrolein. There are no particular restrictions on the method of adding the methacrolein, and it can be appropriately selected depending on the purpose.

[0028] <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.

[0029] -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.

[0030] 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 for measuring 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 methacrolein peak.

[0031] 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.

[0032] -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.

[0033] 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.

[0034] -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 Scan start mass: 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.

[0035] During data analysis, the EIC peak area (EIC: m / z) of methacrolein, which appears at the relative retention time, is determined using the extracted ion chromatogram (EIC) with the relative retention time of deuterium toluene set to 1.0, as shown in Table 1. The methacrolein peak is identified beforehand by confirming the relative retention time and mass spectrum using the respective reagents.

[0036] [Table 1]

[0037] In the aforementioned mass spectrometry, it is preferable to use the Agilent 5977B MSD manufactured by Agilent Technologies.

[0038] To calculate the deuterated toluene equivalent concentration of methacrolein in the vapor of a 3,5,5-trimethylhexanoic acid composition, it is assumed that the sensitivity of the methacrolein EIC peak is equal to that of the deuterated toluene EIC peak, 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 identified in advance are not included in the calculation. In addition, the deuterated toluene equivalent concentration of methacrolein contained in the measurement environment is analyzed, and the respective concentrations are calculated as the difference.

[0039] (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)".

[0040] 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.

[0041] (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)".

[0042] 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.

[0043] (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 step of adjusting the methacrolein concentration, and may further include other steps.

[0044] -Methacrolein concentration adjustment process- The aforementioned methacrolein concentration adjustment step is a step in which, in a 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid, the concentration of methacrolein as a trace component, measured by olfactory gas chromatography / mass spectrometry under the above-described measurement conditions, is adjusted to be between 0.50 volume ppb and 30 volume ppb. The 3,5,5-trimethylhexanoic acid composition is as described above in "(3,5,5-trimethylhexanoic acid composition)".

[0045] In the aforementioned methacrolein concentration adjustment step, there are no particular restrictions on the method of adjusting the concentration, and it can be appropriately selected depending on the purpose, but examples include adding methacrolein. There are no particular restrictions on the method of adding the methacrolein, and it can be appropriately selected depending on the purpose.

[0046] In the metacrolein concentration adjustment step, the preferred range of the metacrolein concentration is as described above in "(3,5,5-trimethylhexanoic acid composition)".

[0047] (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 step for adjusting the methacrolein concentration, and may further include other steps. The methacrolein concentration adjustment step is as described in the "(Odor Suppression Method)" section above.

[0048] (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)".

[0049] 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.

[0050] 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.

[0051] 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.

[0052] (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)".

[0053] 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.

[0054] 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.

[0055] 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.

[0056] 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.

[0057] 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]

[0058] The following describes embodiments of the present invention, but the present invention is not limited in any way to these embodiments.

[0059] (Manufacturing 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.

[0060] -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%.

[0061] (Comparative Example 1) Purified 3,5,5-trimethylhexanoic acid obtained by the same method as in Production Example 1 was mixed with 0.006 g of methacrolein (Merck, 98.0% purity) to obtain 100.00 g of a mixture. Furthermore, 99.99 g of purified 3,5,5-trimethylhexanoic acid obtained by the same method as in Production Example 1 was mixed with 0.010 g of the above mixture to obtain a 3,5,5-trimethylhexanoic acid composition containing methacrolein.

[0062] (Example 1) A 3,5,5-trimethylhexanoic acid composition was obtained in the same manner as in Comparative Example 1, except that 0.042 g of methacrolein was used instead of 0.006 g.

[0063] (Example 2) A 3,5,5-trimethylhexanoic acid composition was obtained in the same manner as in Comparative Example 1, except that 0.087 g of methacrolein was used instead of 0.006 g.

[0064] (Example 3) A 3,5,5-trimethylhexanoic acid composition was obtained in the same manner as in Comparative Example 1, except that 0.150 g of methacrolein was used instead of 0.006 g.

[0065] (Example 4) A 3,5,5-trimethylhexanoic acid composition was obtained in the same manner as in Comparative Example 1, except that 0.320 g of methacrolein was used instead of 0.006 g.

[0066] (Example 5) A 3,5,5-trimethylhexanoic acid composition was obtained in the same manner as in Comparative Example 1, except that 0.400 g of methacrolein was used instead of 0.006 g.

[0067] (Comparative Example 2) A 3,5,5-trimethylhexanoic acid composition was obtained in the same manner as in Comparative Example 1, except that 0.800 g of methacrolein was used instead of 0.006 g.

[0068] (Comparative Example 3) A 3,5,5-trimethylhexanoic acid composition was obtained in the same manner as in Comparative Example 1, except that 1,500 g of methacrolein was used instead of 0.006 g.

[0069] <Analysis 1 (Gas Chromatography Analysis)> The 3,5,5-trimethylhexanoic acid compositions obtained in Examples 1-5 and Comparative Examples 1-3 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.

[0070] -Gas chromatographic 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

[0071] [Table 2]

[0072] <Analysis 2 (Odor Gas Chromatography / Mass Spectrometry)> The concentration of methacrolein in the 3,5,5-trimethylhexanoic acid compositions obtained in Examples 1-5 and Comparative Examples 1-3 was measured 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.

[0073] -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

[0074] -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.

[0075] -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 mass: 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.

[0076] During data analysis, the EIC peak area (EIC: m / z) of methacrolein, which appears at the relative retention time, was determined using extracted ion chromatograms (EIC) with the relative retention time of deuterium toluene set to 1.0, as shown in Table 3. The methacrolein peak was identified beforehand by confirming the relative retention time and mass spectrum using each reagent.

[0077] [Table 3]

[0078] To calculate the equivalent concentration of methacrolein in the vapor of the 3,5,5-trimethylhexanoic acid composition, it was assumed that the sensitivity of the methacrolein EIC peak was equal to that of the deuterated toluene (EIC: m / z 98.000), and the calculation was performed using Equation 1, derived from the calibration curve described above. Furthermore, the equivalent concentration of methacrolein 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

[0079] <Odor Evaluation> The 3,5,5-trimethylhexanoic acid compositions obtained in Examples 1-5 and Comparative Examples 1-3 were each placed in 20 mL wide-mouthed bottles at a rate of 10 g, the lids were closed, and the bottles were 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.

[0080] -Evaluation Criteria- 1: I smell a sewage-like odor. 2: I can smell a slight sewage-like odor. 3: There is no sewage-like odor.

[0081] The results in Table 2 show that a 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid and methacrolein at a concentration of 0.50 ppb to 30 ppb can be obtained, resulting in a 3,5,5-trimethylhexanoic acid composition with suppressed odor.

[0082] Examples of embodiments of the present invention include the following: <1> It contains 3,5,5-trimethylhexanoic acid and a trace amount of methacrolein. The 3,5,5-trimethylhexanoic acid composition is characterized in that the deuterium-to-toluene concentration of the methacrolein, measured by olfactory gas chromatography / mass spectrometry under the following measurement conditions, is 0.50 ppb by volume or more and 30 ppb by volume 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: 5.0g 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 Scan start mass: 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 70.000) of methacrolein appearing at relative retention times of 0.55 to 0.61, 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. <2> 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. <1> This is the 3,5,5-trimethylhexanoic acid composition described in [reference]. <3> The aforementioned <1> or <2> This is a cosmetic ingredient composition characterized by containing the 3,5,5-trimethylhexanoic acid composition described above. <4> The aforementioned <1> or <2> This is a raw material composition for refrigeration oil, characterized by containing the 3,5,5-trimethylhexanoic acid composition described above. <5> This method for suppressing odor in a 3,5,5-trimethylhexanoic acid composition is characterized by including a methacrolein concentration adjustment step, in which the concentration of methacrolein as a trace component, measured by odor olfactory gas chromatography / mass spectrometry under the following measurement conditions, is adjusted to be between 0.50 volume ppb and 30 volume ppb. (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 Scan start mass: 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 70.000) of methacrolein appearing at relative retention times of 0.55 to 0.61, 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. <6> A method for producing a low-odor 3,5,5-trimethylhexanoic acid composition, characterized by including a methacrolein concentration adjustment step, in which the concentration of methacrolein as a trace component, measured by odor gas chromatography / mass spectrometry under the following measurement conditions, is adjusted to be between 0.50 volume ppb and 30 volume ppb. (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 Scan start mass: 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 70.000) of methacrolein appearing at relative retention times of 0.55 to 0.61, 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. <7> The aforementioned <1> or <2> A method for producing a cosmetic composition using the 3,5,5-trimethylhexanoic acid composition described above, 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. <8> The aforementioned <1> or <2> A method for producing a refrigeration oil composition using the 3,5,5-trimethylhexanoic acid composition described above, 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 a trace amount of methacrolein. A 3,5,5-trimethylhexanoic acid composition characterized in that the deuterium-to-toluene concentration of the methacrolein, measured by olfactory gas chromatography / mass spectrometry under the following measurement conditions, is 0.50 volume ppb or more and 30 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 70.000) of methacrolein appearing at relative retention times of 0.55 to 0.61, 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.

2. 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 1, wherein the measuring instrument used in the mass spectrometry is an Agilent 5977B MSD manufactured by Agilent Technologies.

3. A cosmetic raw material composition characterized by comprising the 3,5,5-trimethylhexanoic acid composition described in claim 1 or 2.

4. A composition for use as a raw material for refrigeration oil, characterized by comprising the 3,5,5-trimethylhexanoic acid composition described in claim 1 or 2.

5. A method for suppressing odor in a 3,5,5-trimethylhexanoic acid composition, characterized by including a methacrolein concentration adjustment step, in which the concentration of methacrolein as a trace component, measured by odor olfactory gas chromatography / mass spectrometry under the following measurement conditions, is adjusted to be 0.50 volume ppb or more and 30 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 70.000) of methacrolein appearing at relative retention times of 0.55 to 0.61, 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.

6. A method for producing a low-odor 3,5,5-trimethylhexanoic acid composition, characterized by including a methacrolein concentration adjustment step, in which the concentration of methacrolein as a trace component, measured by odor gas chromatography / mass spectrometry under the following measurement conditions, is adjusted to be 0.50 volume ppb or more and 30 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 70.000) of methacrolein appearing at relative retention times of 0.55 to 0.61, 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.

7. A method for producing a cosmetic composition using the 3,5,5-trimethylhexanoic acid composition described in claim 1 or 2, 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.

8. A method for producing a refrigeration oil composition using the 3,5,5-trimethylhexanoic acid composition described in claim 1 or 2, 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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