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CN-121986084-A - 3, 5-Trimethylhexanoic acid composition, method for inhibiting odor in 3, 5-trimethylhexanoic acid composition, and method for producing low-odor 3, 5-trimethylhexanoic acid composition

CN121986084ACN 121986084 ACN121986084 ACN 121986084ACN-121986084-A

Abstract

The present invention relates to a 3, 5-trimethylhexanoic acid composition and the like, comprising 3, 5-trimethylhexanoic acid and formic acid as a minor component, wherein the concentration of the formic acid is more than 0 mass ppm and 25 mass ppm or less based on liquid chromatography analysis.

Inventors

  • YUSUKE OGATA
  • OHTA DAISUKE
  • Tail Fang Zhen You Xiang
  • NISHIMURA YASUNOBU

Assignees

  • KH新化株式会社

Dates

Publication Date
20260505
Application Date
20250610

Claims (10)

  1. 1. A3, 5-trimethylhexanoic acid composition, characterized in that, Comprises 3, 5-trimethylhexanoic acid and formic acid as minor components, The concentration of the formic acid based on liquid chromatography measured under the following measurement conditions exceeds 0 mass ppm and is 25 mass ppm or less, (Measurement conditions) Column A packed column for reversed-phase chromatography having a length of 25 cm. Times.an inner diameter of 4.6mm, The stationary phase of the analytical column comprises silica gel particles having a particle diameter of 5 μm, a pore diameter of 100A, a specific surface area of 450m 2 /g, a pore volume of 1.10mL/g, and a carbon content of 15% which are obtained by introducing octadecyl groups in a single layer onto the surface, Mobile phase A0.1 mass% phosphoric acid aqueous solution, mobile phase B acetonitrile, Gradient conditions the ratio of mobile phase a to mobile phase B was varied as follows depending on the analysis time, Moving phase A100% for 0-15 min, 15-25 Minutes from mobile phase a100% to mobile phase B100%, 25-30 Minutes mobile phase B100%, From mobile phase B100% to mobile phase a100% linearly for 30-40 minutes, 40-60 Minutes mobile phase A100%, Mobile phase flow rate 1.0 mL/min, The temperature of the column box is 40 ℃, The detector is a UV detector which, The wavelength used was 210nm and, The sample injection method is to use an automatic sampler, The sample injection amount was 10.0. Mu.L, The sample is used with or without dilution or undiluted, Calibration curve A sample having a known concentration of formic acid component was analyzed at 3 or more points, and a calibration curve was prepared using the peak area of the formic acid component.
  2. 2. The 3, 5-trimethylhexanoic acid composition of claim 1, wherein, The concentration of the formic acid is not less than 0.10 mass ppm and not more than 22 mass ppm.
  3. 3. The 3, 5-trimethylhexanoic acid composition of claim 1, wherein, Comprises 4, 4-dimethyl-2-pentanone as a minor component, The concentration of 4, 4-dimethyl-2-pentanone measured under the following measurement conditions in terms of deuterated toluene is 5.0 to 50 ppb by volume based on odor-smell-sensing gas chromatography/mass spectrometry, (Measurement conditions) Concentration- An automatic concentration device comprising means for sucking a gas phase portion of a container for holding an organic compound, a module 1, a module 2, and a module 3, wherein the module 1 is a ceramic-coated trap not filled with an adsorbent for removing moisture from the gas phase portion, 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 portion from which moisture is removed and removing nitrogen, oxygen, carbon dioxide, and methane, the module 3 is a rapid heater for adsorbing the gas phase portion desorbed from the trap, and then performing rapid heating to desorb it, thereby introducing it into a gas chromatograph, The sample amount was 5.0g, The injection amount is 200mL of the sample gas phase portion in the container which is kept at 30 ℃ for 20 minutes or more, and 100mL of the other internal standard substance, The internal standard is deuterated toluene standard gas (the concentration is 10 ppb by volume, and the diluent gas is nitrogen), The concentration method comprises the following steps: the temperature condition of the module 1 is that the adsorption temperature is minus 40 ℃ and the desorption temperature is 0 ℃, The temperature condition of the module 2 is that the adsorption temperature is minus 30 ℃ and the desorption temperature is 200 ℃, The temperature condition of the module 3 is that the adsorption temperature is-165 ℃ and the desorption temperature is 100 ℃, The flow rate of the components in the sample gas phase portion in the flow through the modules 1 and 2 was 50 mL/min, The helium flow rate for removing the remaining part after adsorption of the components of the gas phase part to the module 2 is 75mL, Helium flow (flow rate) for transferring the components of the gas phase desorbed by the module 1 to the module 2 is 40mL (100 mL/min), The time for transferring the components of the gas phase desorbed by the module 2 to the module 3 is 3.0 minutes, The desorption time for introducing the components adsorbed on the gas phase portion of the module 3 to the gas chromatograph was 0.3 minutes, Gas chromatography- The stationary phase is a dimethylpolysiloxane film thickness of 1 μm, the length is 60m times the inner diameter is 320 μm, Heating program, after keeping at 35 ℃ for 2 minutes, heating at 10 ℃ per minute, keeping for 7 minutes and 30 seconds after reaching 240 ℃, The sample introduction temperature was 220C, The carrier gas is helium gas, The split ratio is 0.667:1, Control mode constant pressure (153.09 kPa), After separation with a capillary column, the concentrated sample is sent to an odor-sniffing system and a mass spectrometer in a ratio of 1:1, Mass spectrometry analysis Ionization mode, EI, The type of measurement is that of the scan, The temperature of the ion source is 250 ℃, The temperature of the quadrupole rods is 150 ℃, The electron energy is 70.0eV, The scanning start quality is 30, The scanning end quality is 400, Calibration curve a calibration curve was prepared using the ion peak area of deuterated toluene (EIC: m/z 98.000) using deuterated toluene standard gas (concentration: 10 vol ppb, dilution gas is nitrogen) as a linear function through the origin, Data analysis using Extracted Ion Chromatogram (EIC), using EIC peak area (EIC: m/z 114.000) of 4, 4-dimethyl-2-pentanone occurring within relative retention time 0.99-1.05 when relative retention time of deuterated toluene was set to 1.0, and calculating deuterated toluene conversion concentration according to the calibration curve.
  4. 4. The 3, 5-trimethylhexanoic acid composition of claim 3, wherein, The conditions for the concentration are as follows: automatic concentration device Entech7200 manufactured by ENTECH INSTRUMENTS company, The sample amount was 5.0g, The injection amount is 200mL of the sample gas phase portion in the container which is kept at 30 ℃ for 20 minutes or more, and 100mL of the other internal standard substance, The internal standard is deuterated toluene standard gas (the concentration is 10 ppb by volume, and the diluent gas is nitrogen), Concentration method CTD mode (cold trap dehydration), The temperature conditions of the dehydration module 1 (EMPTY TRAP: non-adsorbent-filled, ceramic-coated trap) were trap temperature-40 ℃ and desorption temperature 0 ℃, The temperature conditions of Cold Tenax module 2 (Tenax TA Trap: ceramic-coated Trap filled with weakly polar porous polymer microbeads based on 2, 6-diphenyl-p-phenylene oxide as adsorbent) were Trap temperature-30C, desorption temperature 200C, The temperature condition of the focusing module 3 (Cryofocusing) is that the trap temperature is-165 ℃ and the desorption temperature is 100 ℃, The flow rate of the sample is 50 mL/min, The He flushing volume is 75mL, The volume of M1 to M2 is 40mL (100 mL/min), The time from M2 to M3 is 3.0 minutes, The sample injection time is 0.3 minutes, The measurement device used in the gas chromatography was an Agilent 7890B gas chromatography system manufactured by Agilent Technologies, The measurement device used in the mass spectrometry was Agilent 5977B MSD manufactured by Agilent Technologies.
  5. 5.A cosmetic raw material composition is characterized in that, Comprising the 3, 5-trimethylhexanoic acid composition of any one of claims 1-4.
  6. 6. A composition for a refrigerator oil material, characterized in that, Comprising the 3, 5-trimethylhexanoic acid composition of any one of claims 1-4.
  7. 7. A method for suppressing odor, characterized in that, Comprises a formic acid concentration adjusting step of adjusting the concentration of formic acid as a trace component in a 3, 5-trimethylhexanoic acid composition containing 3, 5-trimethylhexanoic acid to more than 0 mass ppm and 25 mass ppm or less based on liquid chromatography measured under the following measurement conditions, (Measurement conditions) Column A packed column for reversed-phase chromatography having a length of 25 cm. Times.an inner diameter of 4.6mm, The stationary phase of the analytical column comprises silica gel particles having a particle diameter of 5 μm, a pore diameter of 100A, a specific surface area of 450m 2 /g, a pore volume of 1.10mL/g, and a carbon content of 15% which are obtained by introducing octadecyl groups in a single layer onto the surface, Mobile phase A0.1 mass% phosphoric acid aqueous solution, mobile phase B acetonitrile, Gradient conditions the ratio of mobile phase a to mobile phase B was varied as follows depending on the analysis time, Moving phase A100% for 0-15 min, 15-25 Minutes from mobile phase a100% to mobile phase B100%, 25-30 Minutes mobile phase B100%, From mobile phase B100% to mobile phase a100% linearly for 30-40 minutes, 40-60 Minutes mobile phase A100%, Mobile phase flow rate 1.0 mL/min, The temperature of the column box is 40 ℃, The detector is a UV detector which, The wavelength used was 210nm and, The sample injection method is to use an automatic sampler, The sample injection amount was 10.0. Mu.L, The sample is used with or without dilution or undiluted, Calibration curve A sample having a known concentration of formic acid component was analyzed at 3 or more points, and a calibration curve was prepared using the peak area of the formic acid component.
  8. 8. A process for producing a low-odor 3, 5-trimethylhexanoic acid composition, characterized by comprising, Comprises a formic acid concentration adjusting step of adjusting the concentration of formic acid as a trace component in a 3, 5-trimethylhexanoic acid composition containing 3, 5-trimethylhexanoic acid to more than 0 mass ppm and 25 mass ppm or less based on liquid chromatography measured under the following measurement conditions, (Measurement conditions) Column A packed column for reversed-phase chromatography having a length of 25 cm. Times.an inner diameter of 4.6mm, The stationary phase of the analytical column comprises silica gel particles having a particle diameter of 5 μm, a pore diameter of 100A, a specific surface area of 450m 2 /g, a pore volume of 1.10mL/g, and a carbon content of 15% which are obtained by introducing octadecyl groups in a single layer onto the surface, Mobile phase A0.1 mass% phosphoric acid aqueous solution, mobile phase B acetonitrile, Gradient conditions the ratio of mobile phase a to mobile phase B was varied as follows depending on the analysis time, Moving phase A100% for 0-15 min, 15-25 Minutes from mobile phase a100% to mobile phase B100%, 25-30 Minutes mobile phase B100%, From mobile phase B100% to mobile phase a100% linearly for 30-40 minutes, 40-60 Minutes mobile phase A100%, Mobile phase flow rate 1.0 mL/min, The temperature of the column box is 40 ℃, The detector is a UV detector which, The wavelength used was 210nm and, The sample injection method is to use an automatic sampler, The sample injection amount was 10.0. Mu.L, The sample is used with or without dilution or undiluted, Calibration curve A sample having a known concentration of formic acid component was analyzed at 3 or more points, and a calibration curve was prepared using the peak area of the formic acid component.
  9. 9. A method for producing a cosmetic composition, comprising using the 3, 5-trimethylhexanoic acid composition of any one of claims 1-4, Comprising a step of derivatizing the 3, 5-trimethylhexanoic acid contained in the 3, 5-trimethylhexanoic acid composition.
  10. 10. A method for producing a refrigerator oil composition, comprising using the 3, 5-trimethylhexanoic acid composition of any one of claims 1-4, Comprising a step of derivatizing the 3, 5-trimethylhexanoic acid contained in the 3, 5-trimethylhexanoic acid composition.

Description

3, 5-Trimethylhexanoic acid composition, method for inhibiting odor in 3, 5-trimethylhexanoic acid composition, and method for producing low-odor 3, 5-trimethylhexanoic acid composition Technical Field The present invention relates to a3, 5-trimethylhexanoic acid composition, a method for suppressing odor in a3, 5-trimethylhexanoic acid composition, and a method for producing a low-odor 3, 5-trimethylhexanoic acid composition. Background It is known that 3, 5-trimethylhexanoic acid can be synthesized by oxidation of 3, 5-trimethylhexanal, which is an aldehyde of a precursor (for example, patent document 1). 3, 5-Trimethylhexanoic acid is used as a raw material for cosmetics, refrigerator oil, metal working oil, and the like. Cosmetics, refrigerating machine oils and metal working oils are required to have low odor from raw materials because they may be exposed although they are trace in their characteristics for use. Heretofore, a 3, 5-trimethylhexanoic acid composition having low reproduction toxicity has been known (patent document 2), but odor remains a problem in the 3, 5-trimethylhexanoic acid composition. Prior art literature Patent literature Patent document 1 International publication No. 2022/118917 Patent document 2 International publication No. 2024/219140 Disclosure of Invention Technical problem to be solved by the invention The present invention solves the problems described in the prior art, and achieves the following objects. That is, an object of the present invention is to provide a 3, 5-trimethylhexanoic acid composition having suppressed odor, a method for suppressing odor in a 3, 5-trimethylhexanoic acid composition, and a method for producing a low-odor 3, 5-trimethylhexanoic acid composition. Technical proposal adopted for solving the technical problems As a result of intensive studies to achieve the above object, the present inventors have found that a 3, 5-trimethylhexanoic acid composition having suppressed odor, a method for suppressing odor in a 3, 5-trimethylhexanoic acid composition, and a method for producing a low-odor 3, 5-trimethylhexanoic acid composition can be provided. The present invention is based on the findings of the present inventors and the like, and as a means for solving the above-described problems, the following is described. That is to say, <1> A 3, 5-trimethylhexanoic acid composition comprising 3, 5-trimethylhexanoic acid and formic acid as a minor component, wherein the concentration of the formic acid based on liquid chromatography analysis measured under the measurement conditions described below is more than 0 mass ppm and 25 mass ppm or less. <2> A composition for cosmetic raw materials, comprising the 3, 5-trimethylhexanoic acid composition of <1> above. <3> A composition for a refrigerator oil stock, comprising the 3, 5-trimethylhexanoic acid composition of <1> above. <4> A method for suppressing odor in a 3, 5-trimethylhexanoic acid composition, comprising a formic acid concentration adjustment step, wherein the concentration of formic acid as a trace component measured under the measurement conditions described below in the 3, 5-trimethylhexanoic acid composition containing 3, 5-trimethylhexanoic acid is adjusted to be more than 0 mass ppm and 25 mass ppm or less. <5> A method for producing a low odor 3, 5-trimethylhexanoic acid composition, comprising a formic acid concentration adjustment step, wherein the concentration of formic acid as a trace component measured under the measurement conditions described below in the 3, 5-trimethylhexanoic acid composition containing 3, 5-trimethylhexanoic acid is adjusted to be more than 0 mass ppm and 25 mass ppm or less. <6> A method for producing a cosmetic composition, wherein the 3, 5-trimethylhexanoic acid composition of <1> is used to produce a cosmetic composition, characterized by comprising a step of derivatizing the 3, 5-trimethylhexanoic acid contained in the 3, 5-trimethylhexanoic acid composition. <7> A method for producing a refrigerator oil composition, wherein the 3, 5-trimethylhexanoic acid composition of <1> is used to produce a refrigerator oil composition, characterized by comprising a step of derivatizing the 3, 5-trimethylhexanoic acid contained in the 3, 5-trimethylhexanoic acid composition. Effects of the invention According to the present invention, a3, 5-trimethylhexanoic acid composition having suppressed odor, a method for suppressing odor in a3, 5-trimethylhexanoic acid composition, and a method for producing a low-odor 3, 5-trimethylhexanoic acid composition can be provided. Drawings Fig. 1 shows an example of an apparatus used in the odor-sensing gas chromatography/mass spectrometry according to the present invention. Detailed Description (3, 5-Trimethylhexanoic acid composition) The 3, 5-trimethylhexanoic acid composition comprises 3, 5-trimethylhexanoic acid and formic acid as minor ingredients, and can further comprise other ingredients. 3, 5-Trimethylhexanoic acid The 3, 5-