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

A 3, 5, 5-trimethylhexanoic acid composition containing 3, 5, 5-trimethylhexanoic acid and methacrolein as a trace component, the methacrolein having a concentration in terms of deuterated toluene of 0.50-30 vol ppb (inclusive) as determined by odor-smelling gas chromatography / mass spectrometry.

Description

TECHNICAL FIELD

[0001] The present application 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

[0002] It is known that 3,5,5-trimethylhexanoic acid can be synthesized by oxidation of an aldehyde, i.e., 3,5,5-trimethylhexanal, which is a precursor (for example, Patent Literature 1). 3,5,5-trimethylhexanoic acid is used as a raw material for cosmetics, a raw material for refrigerant oil, a raw material for metal working oil, and the like. Cosmetics, refrigerant oil, and metal working oil have a possibility of being exposed, although in a trace amount, depending on the properties of their uses, and thus a low odor is required for the raw materials.

[0003] Hitherto, a 3,5,5-trimethylhexanoic acid composition having excellent sulfuric acid coloring evaluation has been known (Patent Literature 2), but odor remains a problem in 3,5,5-trimethylhexanoic acid compositions. PRIOR ART DOCUMENTS PATENT LITERATURE

[0004] Patent Literature 1: International Publication No. 2022 / 118917 Patent Literature 2: International Publication No. 2024 / 219139 SUMMARY PROBLEMS TO BE SOLVED BY THE INVENTION

[0005] An object of the present application is to provide a 3,5,5-trimethylhexanoic acid composition in which odor is suppressed, 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. TECHNICAL SOLUTION

[0006] As a result of intensive studies made by the present inventors and others in order to achieve the object, it has been found that a 3,5,5-trimethylhexanoic acid composition in which odor is suppressed, 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 application is based on the insight obtained by the present inventors and others, and as a method for solving the problems, the following is provided. That is, <1> A 3,5,5-trimethylhexanoic acid composition characterized by comprising 3,5,5-trimethylhexanoic acid and methacrolein as a trace component, ​The deuterated toluene conversion concentration of methacrolein, which is a trace component, based on the odor sniffing gas chromatography / mass spectrometry analysis measured under the measurement conditions described later, is adjusted to a methacrolein concentration of 0.50 volume ppb or more and 30 volume ppb or less. <2> A cosmetic raw material composition characterized by comprising the 3,5,5-trimethylhexanoic acid composition of <1>. <3> A refrigerant oil raw material composition characterized by comprising the 3,5,5-trimethylhexanoic acid composition of <1>. <4> A method for suppressing odor in a 3,5,5-trimethylhexanoic acid composition, characterized by comprising: a methacrolein concentration adjustment step of adjusting, in a 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid, the deuterated toluene conversion concentration of methacrolein, which is a trace component, based on the odor sniffing gas chromatography / mass spectrometry analysis measured under the measurement conditions described later, to a methacrolein concentration of 0.50 volume ppb or more and 30 volume ppb or less. <5> A method for producing a low-odor 3,5,5-trimethylhexanoic acid composition, characterized by comprising: a methacrolein concentration adjustment step of adjusting, in a 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid, the deuterated toluene conversion concentration of methacrolein, which is a trace component, based on the odor sniffing gas chromatography / mass spectrometry analysis measured under the measurement conditions described later, to a methacrolein concentration of 0.50 volume ppb or more and 30 volume ppb or less. <6> A method for producing a cosmetic composition, which uses the 3,5,5-trimethylhexanoic acid composition of <1> to produce a cosmetic composition, characterized by comprising a step of derivatizing the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition. <7> A method for producing a refrigerant oil composition, which uses the 3,5,5-trimethylhexanoic acid composition of <1> to produce a refrigerant oil composition, 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 application, it is possible to provide a 3,5,5-trimethylhexanoic acid composition in which odor is suppressed, 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 DESCRIPTION OF DRAWINGS

[0009] Figure 1 This is an example of an apparatus used in the odor sniffing gas chromatography / mass spectrometry analysis of the present application. DETAILED DESCRIPTION

[0010] (3,5,5-trimethylhexanoic acid composition) The 3,5,5-trimethylhexanoic acid composition contains 3,5,5-trimethylhexanoic acid and methacrolein as a trace component, and can further contain other components.

[0011] - 3,5,5-trimethylhexanoic acid - The 3,5,5-trimethylhexanoic acid is a compound represented by the formula (CH3)3CCH2CH(CH3)CH2COOH having a molecular weight of 158.24. 18 O2, formula (CH3)3CCH2CH(CH3)CH2COOH, having a molecular weight of 158.24. The 3,5,5-trimethylhexanoic acid is sometimes also referred to as isononyl 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 depending on the purpose, and is preferably 95.0% or greater, more preferably 97.0% or greater, further preferably 98.5% or greater, and particularly preferably 99.0% or greater.

[0013] The timing of measurement of the concentration of the 3,5,5-trimethylhexanoic acid is not particularly limited and can be appropriately selected depending on the purpose.

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

[0015] The gas chromatograph device can be, for example, "Gas Chromatograph 2010 Plus" manufactured by Shimadzu Corporation. The column for gas chromatography can be, for example, "DB-FFAP" (part number: 122-3232) manufactured by Agilent Technologies, Inc. The measurement conditions for gas chromatography are as follows. (Measurement conditions) Analytical column: column having a length of 30 m x inner diameter of 0.25 mm, in which the stationary phase contains a highly polar polyethylene glycol having a film thickness of 0.25 μm Temperature rising program: 1 minute at 80°C, then temperature rising at 10°C / min, 26 minutes at 210°C after reaching Sample introduction temperature: 250°C Carrier gas: nitrogen Column gas flow rate: 1.0 mL / min Detector and detection temperature: hydrogen flame ionization detector (FID), 250°C Control mode: constant linear velocity mode Flow split ratio: 50:1 Sample injection conditions: 0.5 μL

[0016] -Methacrolein- The methacrolein is a compound with the molecular formula C4H6O, the indicative formula CH2=C(CH3)CHO, and a molecular weight of 70.09. The methacrolein is sometimes also called isobutylene aldehyde or 2-methyl-2-propenal.

[0017] The concentration of methacrolein 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.

[0018] As for the lower limit of the deuterated toluene equivalent concentration of the methacrolein, there is no particular limitation as long as it is 0.50 ppb or more by volume, and it can be appropriately selected according to the purpose. It is preferably 1.0 ppb or more by volume, more preferably 2.0 ppb or more by volume, further preferably 3.0 ppb or more by volume, and particularly preferably 4.0 ppb or more by volume. As for the upper limit of the deuterated toluene conversion concentration of the methacrolein, 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. Preferably, it is 25 volume ppb or less, more preferably 20 volume ppb or less, further preferably 19 volume ppb or less, particularly preferably 18 volume ppb or less, and most preferably 15 volume ppb or less. Furthermore, the range of values ​​that can be set as lower and upper limits, respectively, can be preferred. Preferably, the volume percentage is 1.0 ppb or more and 25 ppb or less, more preferably 2.0 ppb or more and 20 ppb or less, even more preferably 2.0 ppb or more and 19 ppb or less, particularly preferably 3.0 ppb or more and 18 ppb or less, and most preferably 4.0 ppb or more and 15 ppb or less.

[0019] There are no particular restrictions on the timing of determining the deuterated toluene equivalent concentration of the aforementioned methacrolein, and it can be appropriately selected according to the purpose.

[0020] -Other ingredients- There are no particular restrictions on the other components mentioned, and they can be appropriately selected according to the purpose.

[0021] - Method for manufacturing 3,5,5-trimethylhexanoic acid composition - As the method for producing the 3,5,5-trimethylhexanoic acid composition, there is no particular limitation, and it can be appropriately selected according to the purpose, and it can be produced by a method including a synthesis step, a purification step, and a methacrolein concentration adjustment step.

[0022] - Synthesis Step - The synthesis step is a step of synthesizing crude 3,5,5-trimethylhexanoic acid. The crude 3,5,5-trimethylhexanoic acid refers to 3,5,5-trimethylhexanoic acid before purification.

[0023] As the method for synthesizing the crude 3,5,5-trimethylhexanoic acid, there is no particular limitation, and it can be appropriately selected according to the purpose, and for example, the method described in International Publication No. 2022 / 118917 or the like can be cited. Specifically, for example, 3,5,5-trimethylhexanal can be synthesized by hydroformylation reaction of diisobutene and carbonyl synthesis gas, and then the crude 3,5,5-trimethylhexanoic acid can be synthesized by oxidation reaction.

[0024] - Purification Step - The purification step is a step of purifying the crude 3,5,5-trimethylhexanoic acid. The purification step can include a distillation step or the like.

[0025] - Distillation Step - The distillation step is a step of removing components having a lower boiling point (low-boiling-point components) and components having a higher boiling point (high-boiling-point components) than the boiling point (120°C / 13 mmHg) of 3,5,5-trimethylhexanoic acid. Specifically, for example, the crude 3,5,5-trimethylhexanoic acid can be put into a three-necked flask equipped with a reflux cooler and a thermometer, and subjected to reduced pressure distillation at 25 kPa, and a fraction having a column top temperature of 180 to 200°C can be recovered to obtain purified 3,5,5-trimethylhexanoic acid. The purified 3,5,5-trimethylhexanoic acid refers to 3,5,5-trimethylhexanoic acid after purification.

[0026] - Methacrolein Concentration Adjustment Step - The methacrolein concentration adjustment step is a step of adjusting the deuterated toluene-converted concentration of methacrolein, which is a trace component based on odor sniffing gas chromatography / mass spectrometry analysis under the measurement conditions described later, to 0.50 volume ppb or more and 30 volume ppb or less in the 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid.

[0027] There are no particular limitations on the method for adjusting the concentration in the methacrolein concentration adjustment process, and it can be appropriately selected according to the purpose. Examples include adding methacrolein. There are no particular limitations on the method of adding the methacrolein, and it can be appropriately selected according to the purpose.

[0028] <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.

[0029] -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.

[0030] 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 of module 1: adsorption temperature -40°C, desorption temperature 0°C Temperature conditions of module 2: adsorption temperature -30°C, desorption temperature 200°C Temperature conditions of module 3: adsorption temperature -165°C, desorption temperature 100°C Flow rate of the component of the gas phase portion of the sample gas circulated in module 1 and module 2: 50 mL / minute Helium flow rate for removing the remaining portion after the component of the gas phase portion is adsorbed to module 2: 75 mL Helium flow rate (flow rate) for transferring the component of the gas phase portion desorbed from module 1 to module 2: 40 mL (100 mL / minute) Time for transferring the component of the gas phase portion desorbed from module 2 to module 3: 3.0 minutes Desorption time for introducing the component of the gas phase portion adsorbed to module 3 to the gas chromatograph: 0.3 minute Here, the reason for using deuterated toluene standard gas as an internal standard in the measurement of 3,5,5-trimethylhexanoic acid composition is that the ion peak of deuterated toluene is confirmed to be detected appropriately, and the device is operating normally, and the relative retention time from the peak of methylpropionaldehyde.

[0031] wherein the concentrating conditions are preferably: Automatic concentration device: Entech 7200 automatic concentration device manufactured by ENTECH INSTRUMENTS Co., Sample amount: 5.0 g, Injection amount: 200 mL of the component of the gas phase portion of the sample in a container which has been left standing at 30°C for 20 minutes or more, and 100 mL of another internal standard, Internal standard: deuterated toluene standard gas (concentration 10 volume ppb, dilution gas is nitrogen), Concentration method: CTD mode (cold trap dehydration), Temperature conditions of Dehydration Module 1 (Empty Trap: trap which is not filled with an adsorbent and which is subjected to ceramic coating) : trap temperature (adsorption temperature) -40°C, desorption temperature (desorption temperature) 0°C, Temperature conditions of Cold Tenax (registered trademark) Module 2 (Tenax TA Trap: trap which is filled with Tenax TA, a weakly polar porous polymer bead (Tenax TA) based on 2,6-diphenyl-p-phenylene oxide as an adsorbent, and which is subjected to ceramic coating): trap temperature (adsorption temperature) -30°C, desorption temperature (desorption temperature) 200°C, Temperature conditions of Focusing Module 3 (Cryo focusing): Trap temperature (adsorption temperature) -165°C, desorption temperature (desorption temperature) 100°C, Sample flow rate: 50 mL / min, He purge volume (helium flow rate): 75 mL, M1 to M2 volume (flow rate of Module 1 to Module 2): 40 mL (100 mL / min), M2 to M3 time (time of Module 2 to Module 3): 3.0 minutes, Injection time: 0.3 minutes. M1, M2, M3 respectively correspond to Module 1, 2, 3 described above, and "M1 to M2" and "M2 to M3" indicate conditions of sample flow between modules.

[0032] Gas chromatograph The measurement conditions of the gas chromatograph for separating volatile organic compounds (vapor) concentrated by the automatic concentration device are as follows. Analysis column: Column with a stationary phase of dimethylpolysiloxane having a film thickness of 1 μm, length of 60 m, and inner diameter of 320 μm Temperature rising program: After keeping at 35°C for 2 minutes, temperature was raised at 10°C / min, and after reaching 240°C, kept 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) After the concentrated sample was separated by the analysis column, it was sent to the odor sniffing system and mass spectrometer at a ratio of 1:1.

[0033] As the measurement device used in the gas chromatograph, an Agilent 7890B gas chromatograph system manufactured by Agilent Technologies, Inc. is preferably used. The analysis column can be, for example, "DB-1" (Part No. 123-1063) manufactured by Agilent Technologies, Inc.

[0034] Mass spectrometer The measurement conditions of the mass spectrometer are as follows. Ionization mode: EI Measurement type: Scan Ion source temperature: 250°C Quadrupole rod temperature: 150°C Electron energy: 70.0 eV Scan start mass: 30 Scan end mass: 400 Calibration curve: A calibration curve of a first function passing through the origin was made using ion peak area of deuterated toluene (EIC: m / z 98.000) using a deuterated toluene standard gas (concentration: 10 volume ppb, dilution gas: nitrogen). In the analysis of the sample, extrapolation was performed even outside the range of the calibration curve to calculate.

[0035] In performing data analysis, an extracted ion chromatogram (EIC) was used to confirm the EIC peak area (EIC: m / z) of methacrolein appearing within 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 methacrolein, the relative retention time and mass spectrum were confirmed in advance using each reagent and identification was performed.

[0036] [Table 1]

[0037] As the mass spectrometer used in the mass spectrometric analysis, an Agilent 5977B MSD manufactured by Agilent Technologies, Inc. is preferably used.

[0038] In the calculation of the deuterated toluene-conversion concentration of methacrolein in the vapor of the 3,5,5-trimethylhexanoic acid composition, the sensitivity of the EIC peak of methacrolein was assumed to be equal to the sensitivity of the EIC peak of deuterated toluene, and the calculation was performed using the formula derived using the above calibration curve. Ideally, a calibration curve is made each time of measurement. Furthermore, in the case where there are multiple peaks within the relative retention times shown in Table 1, the peak area excluding the peak identified in advance is not included and the calculation is performed. In addition, the deuterated toluene-conversion concentration of methacrolein contained in the analysis measurement environment was calculated as the difference of each concentration.

[0039] (Composition for cosmetic raw material) The composition for cosmetic raw material contains the 3,5,5-trimethylhexanoic acid composition, and can further contain other components. The 3,5,5-trimethylhexanoic acid composition is as described above in "(3,5,5-trimethylhexanoic acid composition)".

[0040] The composition for cosmetic raw material 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] (Composition for refrigerant oil raw material) The composition for refrigerant oil raw material contains the 3,5,5-trimethylhexanoic acid composition, and can further contain other components. The 3,5,5-trimethylhexanoic acid composition is as described above in "(3,5,5-trimethylhexanoic acid composition)".

[0042] The refrigerant oil raw material composition can be incorporated into a refrigerant oil composition after derivatizing the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition.

[0043] (Method for suppressing odor) The method for suppressing odor is a method for suppressing odor in a 3,5,5-trimethylhexanoic acid composition. The method for suppressing odor includes a methacrolein concentration adjustment step, and can further include other steps.

[0044] -Methacrolein concentration adjustment step- The methacrolein concentration adjustment step is a step of adjusting the deuterated toluene-converted concentration of methacrolein, which is a trace component based on odor sniffing gas chromatography / mass spectrometry analysis under the above-described measurement conditions, to 0.50 volume ppb or more and 30 volume ppb or less in a 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid. The 3,5,5-trimethylhexanoic acid composition is as described above in "(3,5,5-trimethylhexanoic acid composition)".

[0045] The method for adjusting the concentration in the methacrolein concentration adjustment step is not particularly limited, and can be appropriately selected according to the purpose. Examples include a method of adding methacrolein. The method of adding methacrolein is not particularly limited, and can be appropriately selected according to the purpose.

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

[0047] (Method for producing low-odor 3,5,5-trimethylhexanoic acid composition) The method for producing a low-odor 3,5,5-trimethylhexanoic acid composition includes a methacrolein concentration adjustment step, and can further include other steps. The methacrolein concentration adjustment step is as described above in "(Method for suppressing odor)".

[0048] (Method for producing cosmetic composition) The method for producing a 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 can 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 the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition is derivatized.

[0050] There is no particular limitation on the method of derivatization, and it can be appropriately selected as desired. For example, esterification of a carboxylic acid containing 3,5,5-trimethylhexanoic acid and a hydroxyl group-containing compound, or the like, can be mentioned. The hydroxyl group-containing compound can be used alone or two or more can be used in combination. In addition, a carboxyl group-containing compound other than 3,5,5-trimethylhexanoic acid can also be used in combination when the esterification or the like is performed.

[0051] As the derivative of 3,5,5-trimethylhexanoic acid in the cosmetic composition, for example, cetyl isononanoate, butylene glycol diisononanoate, octyl isononanoate, isodecyl isononanoate, isononyl isononanoate, cetearyl isononanoate, tridecyl isononanoate, isostearyl isononanoate, isotridecyl isononanoate, ethylhexyl isononanoate, tricyclodecane methyl isononanoate, diethylene glycol diisononanoate, neopentyl glycol diisononanoate, pentaerythritol tetraisononanoate, polyglyceryl-20 octaisononanoate, dipentaerythritol hexaisononanoate, dipentaerythritol pentaisiononanoate, diethylene glycol di(ethylhexanoate / isononanoate), (polyglyceryl-2 isononanoate / dipolymerized linoleic acid) copolymer, (trimethyl pentanediol / adipic acid / isononanoic acid) copolymer, and the like can be mentioned.

[0052] (Method for producing refrigerant oil composition) The method for producing the refrigerant oil composition is a method for producing a refrigerant oil composition using the 3,5,5-trimethylhexanoic acid composition. The method for producing the refrigerant oil composition includes a step of derivatizing the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition, and can 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 refrigerant oil composition after the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition is derivatized.

[0054] As the method of the derivatization, there is no particular limitation, and it can be appropriately selected according to the purpose, and for example, esterification of a carboxylic acid including 3,5,5-trimethylhexanoic acid and a hydroxyl group-containing compound, and the like can be cited. The hydroxyl group-containing compound can be used alone, or two or more kinds can be used in combination. In addition, when the esterification and the like are performed, a carboxylic acid-containing compound other than 3,5,5-trimethylhexanoic acid can also be used in combination.

[0055] As the derivative of 3,5,5-trimethylhexanoic acid in the refrigerant oil composition, for example, an ester of a carboxylic acid including 3,5,5-trimethylhexanoic acid and a polyol, and the like can be cited.

[0056] As the polyol, for example, 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, 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, trimethylol ethane, trimethylol propane, trimethylol butane, 3-hydroxy-2,2-dimethylpropyl-3-hydroxy-2,2-dimethylpropyl acetate, pentaerythritol, polyglycerol (2 to 20 polymer of glycerol), ditrimethylol propane, di-pentaerythritol, tri-pentaerythritol, di(trimethylol propane), tri(trimethylol propane), di-pentaerythritol, di(pentaerythritol), tri(pentaerythritol), sorbitol, sorbitan, sorbitol glycerol condensate, ribitol, arabitol, xylitol, mannitol, and the like sugar alcohols, xylose, arabinose, ribose, rhamnose, glucose, fructose, galactose, mannose, sorbose, cellobiose, maltose, isomaltose, trehalose, sucrose, raffinose, gentiobiase, maltotriose, and the like sugars, and partial etherification products thereof, methyl glucoside (glycoside), and the like can be cited. The polyol can be used alone, or two or more kinds can be used in combination.

[0057] The ester of the carboxylic acid including 3,5,5-trimethylhexanoic acid and the polyol can be combined with a carboxylic acid other than 3,5,5-trimethylhexanoic acid. As the carboxylic acid other than the 3,5,5-trimethylhexanoic acid, for example, there are mentioned straight-chain or branched aliphatic monocarboxylic acids such as 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, isotridecanoic acid, phytanic acid, myristoleic acid, palmitoleic acid, heptadecenoic acid, octadecenoic acid, elaidic acid, oleic acid, vaccenic acid, linoleic acid, elaidolinoleic acid, eicosatrienoic acid, linolenic acid, and arachidonic acid; polybasic carboxylic acids such as 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, 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-cyclohexane dicarboxylic acid, 4-cyclohexene-1,2-dicarboxylic acid, phthalic acid, terephthalic acid, isophthalic acid, trimellitic acid, pyromellitic acid, and the like. The carboxylic acid other than the 3,5,5-trimethylhexanoic acid can be used alone or in combination of two or more. Example

[0058] Hereinafter, examples of the present application will be described, but the present application is not limited to these examples.

[0059] (Production Example 1) -Synthesis Step- According to Example 15 of International Publication No. 2022 / 118917, crude 3,5,5-trimethylhexanoic acid was synthesized. That is, 3,5,5-trimethylhexanal was synthesized by a hydroformylation reaction of diisobutene and carbonyl synthesis gas, and then, crude 3,5,5-trimethylhexanoic acid was obtained by an oxidation reaction.

[0060] -Distillation Step- The crude 3,5,5-trimethylhexanoic acid 239.50 g obtained in the synthesis step was put into a 300 mL three-necked flask equipped with a reflux cooler and a thermometer, and subjected to reduced pressure distillation at 25 kPa, and a fraction having a top temperature of 188 to 191°C was recovered to obtain purified 3,5,5-trimethylhexanoic acid 184.64 g at a recovery rate of 77.1%.

[0061] (Comparative Example 1) The 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, purity 98.0%) to obtain a mixture of 100.00 g. Furthermore, the purified 3,5,5-trimethylhexanoic acid obtained by the same method as in Production Example 1 was mixed with the mixture of 0.010 g 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)> The 3,5,5-trimethylhexanoic acid composition obtained in Examples 1 to 5 and Comparative Examples 1 to 3 was subjected to gas chromatography analysis 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 with respect to the total peak area. The results are shown in Table 2.

[0070] - Gas chromatography analysis conditions - (Measurement conditions) Apparatus: "Gas Chromatograph 2010 Plus" manufactured by Shimadzu Corporation Analytical column: "DB-FFAP" (column having a length of 30 m, an inner diameter of 0.25 mm, and a stationary phase containing a highly polar polyethylene glycol with a film thickness of 0.25 μm) manufactured by Agilent Technologies, Inc. (Part No. 122-3232) Temperature rising program: 1 minute at 80°C, then temperature rising at 10°C / min, 26 minutes at 210°C after reaching 210°C Sample introduction temperature: 250°C Carrier gas: nitrogen Column gas flow rate: 1.0 mL / min Detector and detection temperature: hydrogen flame ionization detector (FID), 250°C Control mode: constant linear velocity mode Split ratio: 50:1 Sample injection conditions: 0.5 μL

[0071] [Table 2]

[0072] < Analysis 2 (odor sniffing gas chromatography / mass spectrometry analysis) > The concentration of methacrolein was measured by odor sniffing gas chromatography / mass spectrometry analysis according to the following method for the 3,5,5-trimethylhexanoic acid composition obtained in Examples 1 to 5 and Comparative Examples 1 to 3. Further, the odor sniffing gas chromatography / mass spectrometry analysis was performed using an apparatus shown in the schematic diagram of the apparatus. Figure 1 The apparatus is composed of a concentration apparatus that sucks the gas phase of a 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 odor sniffing system that can directly sniff the separated components, and a mass spectrometer that qualitatively and quantitatively analyzes the separated components.

[0073] - Concentration of sample - The obtained 3,5,5-trimethylhexanoic acid composition 5.0 g was filled into a sealable 500 mL container, and after standing at 30°C for 20 minutes or more, 200 mL of the gas phase portion was suctioned and introduced into an automatic concentration device. Automatic concentration device: Entech 7200 automatic concentration device manufactured by ENTECH INSTRUMENTS Sample amount: 5.0 g Container capacity: 500 mL Injection amount: 200 mL of the gas phase portion, and 100 mL of an internal standard separated from the gas phase portion Internal standard: deuterated toluene standard gas (concentration 10 volume ppb, dilution gas nitrogen, Sumitomo Seika Chemicals Co., Ltd.) Concentration method: CTD mode (cold trap dehydration) Temperature conditions of dehydration module 1 (Empty Trap: a trap with no adsorbent filled, which has been subjected to ceramic coating) : trap temperature -40°C, desorption temperature 0°C Temperature conditions of Cold Tenax (registered trademark) module 2 (Tenax TA Trap: a trap with a weakly polar porous polymer beads (Tenax TA) based on 2,6-diphenyl-p-phenylene oxide as an adsorbent filled, which has been subjected to ceramic coating) : trap temperature -30°C, desorption temperature 200°C Temperature conditions of focusing module 3 (Cryo focusing) : trap temperature -165°C, desorption temperature 100°C Sample flow rate: 50 mL / minute He purge volume: 75 mL Volume of M1 to M2: 40 mL (100 mL / minute) Time of M2 to M3: 3.0 minutes Injection time: 0.3 minutes

[0074] Gas chromatography Measurement device: Agilent 7890B gas chromatograph system manufactured by Agilent Technologies Analysis column: DB-1 manufactured by Agilent Technologies (part number: 123-1063) (column with a film thickness of 1 μm of dimethylpolysiloxane as a stationary phase, length 60 m x inner diameter 320 μm) Temperature rising program: 2 minutes at 35°C, then temperature rising at 10°C / minute, 7 minutes and 30 seconds at 240°C Sample introduction temperature: 220°C Carrier gas: helium Split ratio: 0.667:1 Control mode: Constant pressure (153.09 kPa) The concentrated sample was sent to the odor sniffing system and the mass spectrometer at a ratio of 1:1 after separation with a capillary column.

[0075] Mass spectrometer Measurement device: Agilent 5977B MSD manufactured by Agilent Technologies, Inc. Ionization mode: EI Measurement type: Scan Ion source temperature: 250°C Quadrupole rod temperature: 150°C Electron energy: 70.0 eV Scan start mass: 30 Scan end mass: 400 Calibration curve: Using a deuterated toluene standard gas (concentration: 10 volume ppb, dilution gas: nitrogen) manufactured by Sumitomo Seika Chemicals Co., Ltd., the injection amount was set to 50 mL, 100 mL, 150 mL, and 200 mL, and the ion peak area of deuterated toluene (EIC: m / z 98.000) was measured. Based on the same injection amount of 200 mL as the measurement of the sample, it was considered that the measurements of the injection amounts of 50 mL, 100 mL, and 150 mL were equivalent to the measurement of the concentration of deuterated toluene of 2.5 volume ppb, 5.0 volume ppb, and 7.5 volume ppb, respectively, according to the volume ratio, and a calibration curve of a first function passing through the origin was created. In the analysis of the sample, extrapolation was performed even outside the range of the calibration curve to calculate.

[0076] In performing data analysis, the extracted ion chromatogram (EIC) was used to confirm the EIC peak area (EIC: m / z) of methacrolein appearing within the relative retention time shown in Table 3 when the relative retention time of deuterated toluene was set to 1.0. Furthermore, for the peak of methacrolein, the relative retention time and mass spectrum were confirmed in advance using each reagent, and identification was performed.

[0077] [Table 3]

[0078] In the calculation of the deuterated toluene-conversion concentration of methacrolein in the vapor of the 3,5,5-trimethylhexanoic acid composition, assuming that the sensitivity of the EIC peak of methacrolein is equal to that of the EIC peak of deuterated toluene (EIC: m / z 98.000), the calculation was performed using Formula 1 derived using the above calibration curve. Furthermore, the deuterated toluene-conversion concentration of methacrolein contained in the measurement environment was analyzed at a sample amount of 0 g, and each concentration was calculated as a difference therefrom. The results are shown in Table 2. [Formula 1] Deuterated toluene conversion concentration (volume ppb) = 5.84 x 10 -6 x EIC peak area of the compound (Formula 1)

[0079] <Odor Evaluation> The 3,5,5-trimethylhexanoic acid composition obtained in Examples 1 to 5 and Comparative Examples 1 to 3 was respectively put into a 20 mL jar at 10 g, capped, and left to stand at room temperature for 30 minutes. After that, the cap was opened, and 3 evaluators evaluated the odor based on the following evaluation criteria. The results (average of 3 evaluators) are shown in Table 2.

[0080] -Evaluation Criteria- 1: Smell of sewer-like odor 2: Slight smell of sewer-like odor 3: No smell of sewer-like odor

[0081] As is clear from the results of Table 2, by 3,5,5-trimethylhexanoic acid, and 3,5,5-trimethylhexanoic acid composition containing 0.50 volume ppb or more and 30 volume ppb or less of methacrolein, a 3,5,5-trimethylhexanoic acid composition in which the odor is suppressed was obtained.

[0082] As a mode of the present application, for example, the following modes can be given. <1> A 3,5,5-trimethylhexanoic acid composition characterized by containing 3,5,5-trimethylhexanoic acid and methacrolein as a trace component, a deuterated toluene conversion concentration of the methacrolein based on odor sniffing gas chromatography / mass spectrometry analysis measured under the following measurement conditions is 0.50 volume ppb or more and 30 volume ppb or less, (Measurement Conditions) -Concentration- Automatic concentration device: A concentration device composed of a device that sucks the gas phase portion of a container in which an organic compound is left to stand, Module 1, Module 2, and Module 3, wherein Module 1 is a ceramic-coated trap that is not filled with an adsorbent for removing moisture from the gas phase portion, Module 2 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 portion from which the moisture is removed and removing nitrogen, oxygen, carbon dioxide, and methane, and Module 3 is a rapid heater for adsorbing the gas phase portion desorbed from the trap and then rapidly heating it to desorb it and thereby introducing it into a gas chromatograph, Sample amount: 5.0 g, Injection amount: 200 mL of the sample gas phase portion in the container which was left standing at 30°C for 20 minutes or more, and 100 mL of another internal standard, Internal standard: deuterated toluene standard gas (concentration 10 volume ppb, dilution gas nitrogen), Concentration method: Temperature conditions of module 1: adsorption temperature -40°C, desorption temperature 0°C, Temperature conditions of module 2: adsorption temperature -30°C, desorption temperature 200°C, Temperature conditions of module 3: adsorption temperature -165°C, desorption temperature 100°C, Flow rate for circulating the components of the sample gas phase portion in module 1 and module 2: 50 mL / minute, Helium flow rate for removing the remaining portion after the components of the gas phase portion are adsorbed to module 2: 75 mL, Helium flow rate (flow rate) for transferring the components of the gas phase portion desorbed from module 1 to module 2: 40 mL (100 mL / minute), Time for transferring the components of the gas phase portion desorbed from module 2 to module 3: 3.0 minutes, Desorption time for introducing the components of the gas phase portion adsorbed to module 3 to the gas chromatograph: 0.3 minutes, Gas chromatograph Analysis column: column with a fixed phase of dimethylpolysiloxane with a film thickness of 1 μm, length 60 m x inner diameter 320 μm, Temperature rising program: 2 minutes at 35°C, then temperature rising at 10°C / minute, 7 minutes 30 seconds at 240°C, Sample introduction temperature: 220°C, Carrier gas: helium, Split ratio: 0.667: 1, Control mode: constant pressure (153.09 kPa), The concentrated sample is sent to the odor sniffing system and the mass spectrometer at a ratio of 1:1 after separation with the capillary column, Mass spectrometric analysis Ionization mode: EI, Measurement type: scan, Ion source temperature: 250°C, Quadrupole rod temperature: 150°C, Electron energy: 70.0 eV, Scan start mass: 30, Scan end mass: 400, Calibration curve: A calibration curve of a first function passing through the origin was prepared using ion peak areas of deuterated toluene (EIC: m / z 98.000) using a deuterated toluene standard gas (concentration: 10 volume ppb, dilution gas: nitrogen), Data analysis: Using the extracted ion chromatogram (EIC), the EIC peak area of methacrolein (EIC: m / z 70.000) appearing within the relative retention time of 0.55 to 0.61 when the relative retention time of deuterated toluene was set to 1.0 was used to calculate the deuterated toluene conversion concentration according to the above calibration curve. <2> The 3,5,5-trimethylhexanoic acid composition according to the above <1>, wherein, The concentration conditions were as follows: Automatic concentration device: Entech 7200 automatic concentration device manufactured by ENTECH INSTRUMENTS Co., Sample amount: 5.0 g, Injection amount: 200 mL of the gas phase of the sample in the container which had been left standing at 30°C for 20 minutes or more, and 100 mL of another internal standard, Internal standard: deuterated toluene standard gas (concentration 10 volume ppb, dilution gas: nitrogen), Concentration method: CTD mode (cold trap dehydration), Temperature conditions of the dehydration module 1 (Empty Trap: a trap with no adsorbent filled, which has been subjected to ceramic coating) : trap temperature -40°C, desorption temperature 0°C, Temperature conditions of the Cold Tenax module 2 (Tenax TA Trap: a trap filled with a weakly polar porous polymer bead based on 2,6-diphenyl-p-phenylene oxide as an adsorbent, which has been subjected to ceramic coating): trap temperature -30°C, desorption temperature 200°C, Temperature conditions of the focusing module 3 (Cryo focusing): trap temperature -165°C, desorption temperature 100°C, Sample flow rate: 50 mL / minute, He purge volume: 75 mL, Volume of M1 to M2: 40 mL (100 mL / minute), Time of M2 to M3: 3.0 minutes, Injection time: 0.3 minutes, The measurement device used in the gas chromatograph was an Agilent 7890B gas chromatograph system manufactured by Agilent Technologies Co., The measuring device used in the mass spectrometric analysis was Agilent 5977B MSD manufactured by Agilent Technologies, Inc. A cosmetic raw material composition characterized by comprising: The 3,5,5-trimethylhexanoic acid composition according to <1> or <2>. A refrigerant oil raw material composition characterized by comprising: The 3,5,5-trimethylhexanoic acid composition according to <1> or <2>. A method for suppressing odor in a 3,5,5-trimethylhexanoic acid composition characterized by comprising: comprising: adjusting the deuterated toluene conversion concentration of methacrolein as a trace component based on odor sniffing gas chromatography / mass spectrometry analysis measured under the following measurement conditions to a methacrolein concentration of 0.50 volume ppb or more and 30 volume ppb or less in a 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid, (Measurement conditions) Concentration Automatic concentration device: concentration device composed of a device that attracts the gas phase of a container in which an organic compound is left standing, Module 1, Module 2, and Module 3, wherein Module 1 is a ceramic-coated trap that is not filled with an adsorbent for removing moisture from the gas phase, Module 2 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 the moisture has been removed and removing nitrogen, oxygen, carbon dioxide, and methane, and Module 3 is a rapid heater for adsorbing the gas phase desorbed from the trap and then rapidly heating it to desorb it and introducing it into a gas chromatograph, Sample amount: 5.0 g, Injection amount: 200 mL of the sample gas phase in the container left standing at 30°C for 20 minutes or more, and 100 mL of another internal standard, Internal standard: deuterated toluene standard gas (concentration 10 volume ppb, dilution gas nitrogen), Concentration method: Temperature conditions for Module 1: adsorption temperature -40°C, desorption temperature 0°C, Temperature conditions for Module 2: adsorption temperature -30°C, desorption temperature 200°C, Temperature conditions for Module 3: adsorption temperature -165°C, desorption temperature 100°C, Flow rate at which the components of the sample gas phase circulate in Module 1 and Module 2: 50 mL / minute, The component of the gas phase portion after adsorption to the module 2 was used to remove the remaining portion of the helium flow: 75 mL, The helium flow (flow rate) for transferring the component of the gas phase portion desorbed from the module 1 to the module 2: 40 mL (100 mL / min), The time for transferring the component of the gas phase portion desorbed from the module 2 to the module 3: 3.0 minutes, The desorption time for introducing the component of the gas phase portion adsorbed to the module 3 into the gas chromatograph: 0.3 minutes, Gas chromatograph Analysis column: Column with a fixed phase of dimethylpolysiloxane with a film thickness of 1 μm, length 60 m x inner diameter 320 μm, Temperature rising program: After 2 minutes at 35°C, temperature rising at 10°C / min, after reaching 240°C, hold for 7 minutes 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 after separation with the capillary column was sent to the odor sniffing system and the mass spectrometer at a ratio of 1:1, Mass spectrometric analysis Ionization mode: EI, Measurement type: Scan, Ion source temperature: 250°C, Temperature of quadrupole rod: 150°C, Electron energy: 70.0 eV, Scan start mass: 30, Scan end mass: 400, Calibration curve: Using a deuterated toluene standard gas (concentration: 10 volume ppb, dilution gas: nitrogen), a calibration curve of a first function passing through the origin was prepared using the ion peak area of deuterated toluene (EIC: m / z 98.000), Data analysis: Using the extracted ion chromatogram (EIC), the EIC peak area of methacrolein (EIC: m / z 70.000) appearing within the relative retention time of 0.55 to 0.61 when the relative retention time of deuterated toluene was set to 1.0 was used to calculate the deuterated toluene conversion concentration according to the above calibration curve. A method for producing a low odor 3,5,5-trimethylhexanoic acid composition, characterized by, The deuterated toluene-equivalent concentration of methacrolein as a trace component based on the odor sniffing gas chromatography / mass spectrometry analysis measured under the following measurement conditions is adjusted to 0.50 volume ppb or more and 30 volume ppb or less in the 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid, (Measurement conditions) Concentration Automatic concentration device: A concentration device composed of a device that sucks the gas phase of a container in which an organic compound is left standing, a module 1, a module 2, and a module 3, wherein the module 1 is a ceramic-coated trap that is not filled with an adsorbent for removing moisture from the gas phase, the module 2 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 the moisture is removed and removing nitrogen, oxygen, carbon dioxide, and methane, and the module 3 is a rapid heater for adsorbing the gas phase desorbed from the trap and then rapidly heating it to be desorbed and introducing it into a gas chromatograph, Sample amount: 5.0 g, Injection amount: 200 mL of the sample gas phase in the container left standing at 30°C for 20 minutes or more, and 100 mL of another internal standard, Internal standard: Deuterated toluene standard gas (concentration 10 volume ppb, dilution gas: nitrogen) Concentration method: Temperature conditions of the module 1: adsorption temperature -40°C, desorption temperature 0°C, Temperature conditions of the module 2: adsorption temperature -30°C, desorption temperature 200°C, Temperature conditions of the module 3: adsorption temperature -165°C, desorption temperature 100°C, Flow rate at which the components of the sample gas phase are circulated in the module 1 and the module 2: 50 mL / minute, Helium flow rate for removing the remaining portion after the components of the gas phase are adsorbed to the module 2: 75 mL, Helium flow rate (flow rate) for transferring the components of the gas phase desorbed from the module 1 to the module 2: 40 mL (100 mL / minute), Time for transferring the components of the gas phase desorbed from the module 2 to the module 3: 3.0 minutes, Desorption time for introducing the components of the gas phase adsorbed to the module 3 into a gas chromatograph: 0.3 minutes, Gas chromatograph Analysis column: Column with a length of 60 m and an inner diameter of 320 μm, with a dimethylpolysiloxane having a film thickness of 1 μm as the stationary phase, Ramp program: 2 minutes at 35 °C, then 10 °C / min to 240 °C, hold for 7 minutes 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 was sent to the odor sniffing system and the mass spectrometer at a ratio of 1:1 after separation with a capillary column, Mass spectrometry Ionization mode: EI, Measurement type: scan, Ion source temperature: 250 °C, Quadrupole rod temperature: 150 °C, Electron energy: 70.0 eV, Scan start mass: 30, Scan end mass: 400, Calibration curve: A calibration curve of a first function passing through the origin was prepared using the ion peak area of deutero-toluene (EIC: m / z 98.000) using a standard gas of deutero-toluene (concentration: 10 volume ppb, dilution gas: nitrogen), Data analysis: Using the extracted ion chromatogram (EIC), the EIC peak area of methyl methacrolein (EIC: m / z 70.000) appearing within the relative retention time of 0.55 to 0.61 when the relative retention time of deutero-toluene was set to 1.0 was used to calculate the deutero-toluene conversion concentration according to the above calibration curve. A method for producing a cosmetic composition, characterized by producing a cosmetic composition using the 3,5,5-trimethylhexanoic acid composition according to <1> or <2>, wherein comprises a step of derivatizing the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition. A method for producing a refrigerator oil composition, characterized by producing a refrigerator oil composition using the 3,5,5-trimethylhexanoic acid composition according to <1> or <2>, wherein comprises a step of derivatizing 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 methacrolein as a trace component. The deuterated toluene concentration of the methacrolein, determined by odor-based gas chromatography / mass spectrometry analysis under the following conditions, is above 0.50 ppb and below 30 ppb. (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 a rate of 10℃ / minute until reaching 240℃, 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). 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 of ​​methacrolein appearing within the relative retention time range of 0.55–0.61 when the relative retention time of deuterated toluene is set to 1.0 (EIC: m / z 70.000) was used to calculate the converted concentration of deuterated toluene based on the calibration curve described above.

2. The 3,5,5-trimethylhexanoic acid composition according to claim 1, 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.

3. A composition for use as a cosmetic ingredient, characterized in that... ， Compositions comprising 3,5,5-trimethylhexanoic acid as described in claim 1 or 2.

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

5. A method for suppressing odor in a 3,5,5-trimethylhexanoic acid composition, characterized in that, include: In a 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid, a methacrolein concentration adjustment step is performed, whereby the concentration of deuterated toluene converted from methacrolein, a trace component determined by odor-based gas chromatography / mass spectrometry analysis under the following measurement conditions, is adjusted to a methacrolein concentration of 0.50 ppb or more and 30 ppb or less. (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 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 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, diluted with nitrogen). Data analysis: Using extracted ion chromatograms (EIC), the EIC peak area of ​​methacrolein appearing within the relative retention time range of 0.55–0.61 when the relative retention time of deuterated toluene is set to 1.0 (EIC: m / z 70.000) was used to calculate the converted concentration of deuterated toluene based on the calibration curve described above.

6. A method for manufacturing a low-odor 3,5,5-trimethylhexanoic acid composition, characterized in that, include: In a 3,5,5-trimethylhexanoic acid composition containing 3,5,5-trimethylhexanoic acid, a methacrolein concentration adjustment step is performed, whereby the concentration of deuterated toluene converted from methacrolein, a trace component determined by odor-based gas chromatography / mass spectrometry analysis under the following measurement conditions, is adjusted to a methacrolein concentration of 0.50 ppb or more and 30 ppb or less. (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 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 a rate of 10℃ / minute until reaching 240℃, 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). 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 of ​​methacrolein appearing within the relative retention time range of 0.55–0.61 when the relative retention time of deuterated toluene is set to 1.0 (EIC: m / z 70.000) was used to calculate the converted concentration of deuterated toluene based on the calibration curve described above.

7. A method for manufacturing a cosmetic composition, comprising using the 3,5,5-trimethylhexanoic acid composition according to claim 1 or 2, characterized in that, The process includes the derivatization of the 3,5,5-trimethylhexanoic acid contained in the 3,5,5-trimethylhexanoic acid composition.

8. A method for manufacturing a refrigeration oil composition, comprising using the 3,5,5-trimethylhexanoic acid composition according to claim 1 or 2 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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