JP2023136604A - Metalworking oil base oil - Google Patents
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- 239000003921 oil Substances 0.000 title claims abstract description 61
- 238000005555 metalworking Methods 0.000 title claims abstract description 49
- 239000002199 base oil Substances 0.000 title claims abstract description 32
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims abstract description 98
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims abstract description 94
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 62
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 61
- 229930195729 fatty acid Natural products 0.000 claims abstract description 61
- 239000000194 fatty acid Substances 0.000 claims abstract description 61
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 60
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims abstract description 47
- 229960002446 octanoic acid Drugs 0.000 claims abstract description 47
- 150000002148 esters Chemical class 0.000 claims abstract description 35
- 235000011187 glycerol Nutrition 0.000 claims abstract description 33
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 238000005886 esterification reaction Methods 0.000 claims description 14
- 150000005691 triesters Chemical class 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 7
- -1 cycloalkane monocarboxylic acids Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000005520 cutting process Methods 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 2
- ITFOCFQAVPXNEV-UHFFFAOYSA-N 10-Methyl-hexadecanoic acid Chemical compound CCCCCCC(C)CCCCCCCCC(O)=O ITFOCFQAVPXNEV-UHFFFAOYSA-N 0.000 description 2
- XKLJLHAPJBUBNL-UHFFFAOYSA-N 12-methyltetradecanoic acid Chemical compound CCC(C)CCCCCCCCCCC(O)=O XKLJLHAPJBUBNL-UHFFFAOYSA-N 0.000 description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- NKBWMBRPILTCRD-UHFFFAOYSA-N 2-Methylheptanoic acid Chemical compound CCCCCC(C)C(O)=O NKBWMBRPILTCRD-UHFFFAOYSA-N 0.000 description 2
- OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 2
- MHPUGCYGQWGLJL-UHFFFAOYSA-N 5-methyl-hexanoic acid Chemical compound CC(C)CCCC(O)=O MHPUGCYGQWGLJL-UHFFFAOYSA-N 0.000 description 2
- VZFUCHSFHOYXIS-UHFFFAOYSA-N Cycloheptanecarboxylic acid Chemical compound OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- RLCKHJSFHOZMDR-UHFFFAOYSA-N (3R, 7R, 11R)-1-Phytanoid acid Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)CC(O)=O RLCKHJSFHOZMDR-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- REHQLKUNRPCYEW-UHFFFAOYSA-N 1-methylcyclohexane-1-carboxylic acid Chemical compound OC(=O)C1(C)CCCCC1 REHQLKUNRPCYEW-UHFFFAOYSA-N 0.000 description 1
- ZONJATNKKGGVSU-UHFFFAOYSA-N 14-methylpentadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCC(O)=O ZONJATNKKGGVSU-UHFFFAOYSA-N 0.000 description 1
- UCDAVJCKGYOYNI-UHFFFAOYSA-N 18-methylnonadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCCCC(O)=O UCDAVJCKGYOYNI-UHFFFAOYSA-N 0.000 description 1
- YTTWDTVYXAEAJA-UHFFFAOYSA-N 2,2-dimethyl-hexanoic acid Chemical compound CCCCC(C)(C)C(O)=O YTTWDTVYXAEAJA-UHFFFAOYSA-N 0.000 description 1
- CVKMFSAVYPAZTQ-UHFFFAOYSA-N 2-methylhexanoic acid Chemical compound CCCCC(C)C(O)=O CVKMFSAVYPAZTQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 1
- RLCKHJSFHOZMDR-PWCSWUJKSA-N 3,7R,11R,15-tetramethyl-hexadecanoic acid Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCCC(C)CC(O)=O RLCKHJSFHOZMDR-PWCSWUJKSA-N 0.000 description 1
- HMMSZUQCCUWXRA-UHFFFAOYSA-N 4,4-dimethyl valeric acid Chemical compound CC(C)(C)CCC(O)=O HMMSZUQCCUWXRA-UHFFFAOYSA-N 0.000 description 1
- YZKLUEWQADEGKP-UHFFFAOYSA-N 5-(2,4-dichlorophenyl)cyclohexane-1,3-dione Chemical compound ClC1=CC(Cl)=CC=C1C1CC(=O)CC(=O)C1 YZKLUEWQADEGKP-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- FXUKWLSZZHVEJD-UHFFFAOYSA-N C16:0-14-methyl Natural products CCC(C)CCCCCCCCCCCCC(O)=O FXUKWLSZZHVEJD-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- ZOCYQVNGROEVLU-UHFFFAOYSA-N Isopentadecylic acid Natural products CC(C)CCCCCCCCCCCC(O)=O ZOCYQVNGROEVLU-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010227 cup method (microbiological evaluation) Methods 0.000 description 1
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- JMOLZNNXZPAGBH-UHFFFAOYSA-N hexyldecanoic acid Chemical compound CCCCCCCCC(C(O)=O)CCCCCC JMOLZNNXZPAGBH-UHFFFAOYSA-N 0.000 description 1
- 229950004531 hexyldecanoic acid Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- IIUXHTGBZYEGHI-UHFFFAOYSA-N iso-margaric acid Natural products CC(C)CCCCCCCCCCCCCC(O)=O IIUXHTGBZYEGHI-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Abstract
Description
本発明は、金属加工油用基油に関する。 The present invention relates to a base oil for metal working oil.
切削・研削加工において、切削工具の冷却性による寿命延長や潤滑性による加工能率の増大等を目的に金属加工油が使用されている。金属加工油組成物には、水に潤滑成分を分散／溶解させた、寿命延長に優れる水溶性金属加工油と、鉱物油や合成油等の油性成分を基材とする加工能率の増大に優れる不水溶性金属加工油との２種類に大別される。 In cutting and grinding processes, metal working oils are used to extend the life of cutting tools through their cooling properties and increase machining efficiency through their lubrication properties. Metalworking oil compositions include water-soluble metalworking oils that have lubricating components dispersed/dissolved in water and are excellent in extending service life, and oily components such as mineral oil and synthetic oil that are excellent in increasing processing efficiency. It is roughly divided into two types: water-insoluble metal working oil.
不水溶性金属加工油は油性成分を基材とするため可燃性の問題がある。 Water-insoluble metalworking oils have a problem of flammability because they are based on oily components.
下記特許文献１、２には、油性成分を基材とする不水溶性金属加工油よりも高い引火点を有する合成エステル系金属加工油組成物が開示されている。 Patent Documents 1 and 2 listed below disclose synthetic ester metalworking oil compositions having a higher flash point than water-insoluble metalworking oils based on oily components.
しかし、従来の合成エステル系金属加工油組成物は、高い引火点を低い粘度の両立という点で改善の余地があった。 However, conventional synthetic ester metalworking oil compositions have room for improvement in terms of achieving both a high flash point and low viscosity.
本発明は、高い引火点と室温付近での低い粘度を両立し、更に低温での流動性を有する、不水溶性金属加工油組成物に配合される金属加工油用基油を提供することを目的とする。 The present invention aims to provide a base oil for metal working oil that is blended into a water-insoluble metal working oil composition, which has both a high flash point and a low viscosity near room temperature, and also has fluidity at low temperatures. purpose.
本発明は、
脂肪酸とグリセリンとのエステルを含む、金属加工油用基油であって、
前記脂肪酸が、カプリル酸とドデカン酸を含み、前記カプリル酸と前記ドデカン酸のモル比（カプリル酸／ドデカン酸）が、７０／３０以上９０／１０以下であり、
前記脂肪酸中の前記カプリル酸と前記ドデカン酸の合計含有量が、８０モル％以上である、金属加工油用基油である。
The present invention
A base oil for metal working oil containing an ester of fatty acid and glycerin,
The fatty acid contains caprylic acid and dodecanoic acid, and the molar ratio of the caprylic acid and the dodecanoic acid (caprylic acid/dodecanoic acid) is 70/30 or more and 90/10 or less,
The base oil for metal working oil has a total content of caprylic acid and dodecanoic acid in the fatty acid of 80 mol% or more.
本発明によれば、高い引火点と室温付近での低い粘度を両立し、更に低温での流動性を有する、不水溶性金属加工油組成物に配合される金属加工油用基油を提供することができる。 According to the present invention, there is provided a base oil for metal working oil that is blended into a water-insoluble metal working oil composition, which has both a high flash point and a low viscosity near room temperature, and also has fluidity at low temperatures. be able to.
＜金属加工油用基油＞
本実施形態の金属加工油用基油は、
脂肪酸とグリセリンとのエステルを含む、金属加工油用基油であって、
前記脂肪酸が、カプリル酸とドデカン酸を含み、前記カプリル酸と前記ドデカン酸のモル比（カプリル酸／ドデカン酸）が、７０／３０以上９０／１０以下であり、
前記脂肪酸中の前記カプリル酸と前記ドデカン酸の合計含有量が、８０モル％以上である。
本実施形態の金属加工油用基油は、高い引火点と室温付近での低い粘度を両立し、更に低温での流動性を有する。
<Base oil for metal processing oil>
The base oil for metal working oil of this embodiment is
A base oil for metal working oil containing an ester of fatty acid and glycerin,
The fatty acid contains caprylic acid and dodecanoic acid, and the molar ratio of the caprylic acid and the dodecanoic acid (caprylic acid/dodecanoic acid) is 70/30 or more and 90/10 or less,
The total content of the caprylic acid and the dodecanoic acid in the fatty acid is 80 mol% or more.
The base oil for metal working oil of this embodiment has both a high flash point and a low viscosity near room temperature, and further has fluidity at low temperatures.
前記カプリル酸と前記ドデカン酸のモル比（カプリル酸／ドデカン酸）は、引火点を高くし、潤滑性を向上させ、かつ低温での流動性を向上させる観点から、７０／３０以上、好ましくは７２．５／２７．５以上、より好ましくは７５／２５以上であり、そして、９０／１０以下、好ましくは８８．５／１１．５以下、より好ましくは８７／１３以下である。 The molar ratio of the caprylic acid and the dodecanoic acid (caprylic acid/dodecanoic acid) is preferably 70/30 or more, from the viewpoint of increasing the flash point, improving lubricity, and improving fluidity at low temperatures. It is 72.5/27.5 or more, more preferably 75/25 or more, and 90/10 or less, preferably 88.5/11.5 or less, more preferably 87/13 or less.
前記脂肪酸中の前記カプリル酸の含有量は特に制限されないが、引火点を高くし、潤滑性を向上させ、かつ低温での流動性を向上させる観点から、好ましくは７０モル％以上、より好ましくは７２．５モル％以上、更に好ましくは７５モル％以上であり、そして、好ましくは９０モル％以下、より好ましくは８８．５モル％以下、更に好ましくは８７モル％以下である。 The content of caprylic acid in the fatty acid is not particularly limited, but from the viewpoint of raising the flash point, improving lubricity, and improving fluidity at low temperatures, it is preferably 70 mol% or more, more preferably It is 72.5 mol% or more, more preferably 75 mol% or more, and preferably 90 mol% or less, more preferably 88.5 mol% or less, still more preferably 87 mol% or less.
前記脂肪酸中の前記ドデカン酸の含有量は特に制限されないが、引火点を高くし、潤滑性を向上させ、かつ低温での流動性を向上させる観点から、好ましくは１０モル％以上、より好ましくは１１．５モル％以上、更に好ましくは１３モル％以上であり、そして、好ましくは３０モル％以下、より好ましくは２７．５モル％以下、更に好ましくは２５モル％以下である。 The content of dodecanoic acid in the fatty acid is not particularly limited, but from the viewpoint of increasing the flash point, improving lubricity, and improving fluidity at low temperatures, it is preferably 10 mol% or more, more preferably It is 11.5 mol% or more, more preferably 13 mol% or more, and preferably 30 mol% or less, more preferably 27.5 mol% or less, still more preferably 25 mol% or less.
前記脂肪酸中の前記カプリル酸と前記ドデカン酸の合計含有量は、引火点を高くし、潤滑性を向上させ、かつ低温での流動性を向上させる観点から、８０モル％以上、好ましくは９０モル％以上、より好ましくは１００モル％以上である。 The total content of the caprylic acid and the dodecanoic acid in the fatty acid is 80 mol% or more, preferably 90 mol%, from the viewpoint of increasing the flash point, improving lubricity, and improving fluidity at low temperatures. % or more, more preferably 100 mol% or more.
前記脂肪酸は、本発明の効果を阻害しない範囲で、前記カプリル酸及び前記ドデカン酸以外の脂肪酸を含有してもよい。前記カプリル酸及び前記ドデカン酸以外の脂肪酸としては、例えば、吉草酸、２－メチル吉草酸、４－メチル吉草酸、ｎ－ヘキサン酸、２－メチルヘキサン酸、５－メチルヘキサン酸、４，４－ジメチルペンタン酸、ｎ－ヘプタン酸、２－メチルヘプタン酸、２－エチルヘキサン酸、２，２－ジメチルヘキサン酸、３，５，５－トリメチルヘキサン酸、ｎ－ノナン酸、ｎ－デカン酸などの炭素数５以上１０以下の脂肪酸；トリデカン酸、テトラデカン酸、ヘキサデカン酸、オクタデカン酸、オレイン酸、リノール酸、エイコサン酸、ベヘン酸、セロチン酸などの炭素数１３以上２６以下の脂肪酸；１３－メチルテトラデカン酸、１２－メチルテトラデカン酸、１５－メチルヘキサデカン酸、１４－メチルヘキサデカン酸、１０－メチルヘキサデカン酸、２－ヘキシルデカン酸、イソパルミチン酸、イソステアリン酸、イソアラキン酸、フィタン酸などの炭素数１５以上２０以下の分岐脂肪酸；シクロプロパンカルボン酸、シクロブタンカルボン酸、シクロペンタンカルボン酸、シクロヘキサンカルボン酸、シクロヘプタンカルボン酸、メチルシクロヘキサンカルボン酸などの炭素数４以上８以下のシクロアルカンモノカルボン酸などが挙げられる。 The fatty acid may contain fatty acids other than the caprylic acid and the dodecanoic acid as long as the effects of the present invention are not impaired. Examples of fatty acids other than the caprylic acid and the dodecanoic acid include valeric acid, 2-methylvaleric acid, 4-methylvaleric acid, n-hexanoic acid, 2-methylhexanoic acid, 5-methylhexanoic acid, 4,4 -Dimethylpentanoic acid, n-heptanoic acid, 2-methylheptanoic acid, 2-ethylhexanoic acid, 2,2-dimethylhexanoic acid, 3,5,5-trimethylhexanoic acid, n-nonanoic acid, n-decanoic acid, etc. Fatty acids with 5 to 10 carbon atoms; fatty acids with 13 to 26 carbon atoms, such as tridecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, oleic acid, linoleic acid, eicosanoic acid, behenic acid, and cerotic acid; 13-methyl 15 or more carbon atoms such as tetradecanoic acid, 12-methyltetradecanoic acid, 15-methylhexadecanoic acid, 14-methylhexadecanoic acid, 10-methylhexadecanoic acid, 2-hexyldecanoic acid, isopalmitic acid, isostearic acid, isoarachidic acid, phytanic acid, etc. 20 or less branched fatty acids; Examples include cycloalkane monocarboxylic acids having 4 to 8 carbon atoms, such as cyclopropanecarboxylic acid, cyclobutanecarboxylic acid, cyclopentanecarboxylic acid, cyclohexanecarboxylic acid, cycloheptanecarboxylic acid, and methylcyclohexanecarboxylic acid. It will be done.
前記エステルは、グリセリントリエステルを主に含むが、本発明の効果を阻害しない範囲で、グリセリン部分エステルを含んでいてもよい。前記グリセリントリエステルとしては、カプリル酸とグリセリンとのトリエステル、ドデカン酸とグリセリンとのトリエステル、及びカプリル酸とドデカン酸の混合脂肪酸とグリセリンとのトリエステルなどが挙げられる。 The ester mainly contains a glycerin triester, but may also contain a glycerin partial ester to the extent that the effects of the present invention are not impaired. Examples of the glycerin triester include triester of caprylic acid and glycerin, triester of dodecanoic acid and glycerin, and triester of mixed fatty acid of caprylic acid and dodecanoic acid and glycerin.
前記グリセリンに対する前記脂肪酸のモル比は、引火点を高くし、潤滑性を向上させ、かつ低温での流動性を向上させる観点から、好ましくは２．６以上、より好ましくは２.８以上、更に好ましくは２．９以上であり、そして、好ましくは３．４以下、より好ましくは３．２以下、更に好ましくは３．１以下である。 The molar ratio of the fatty acid to the glycerin is preferably 2.6 or more, more preferably 2.8 or more, from the viewpoint of increasing the flash point, improving lubricity, and improving fluidity at low temperatures. It is preferably 2.9 or more, and preferably 3.4 or less, more preferably 3.2 or less, and still more preferably 3.1 or less.
前記エステルは、引火点を高くし、潤滑性を向上させ、かつ低温での流動性を向上させる観点から、カプリル酸とドデカン酸の混合脂肪酸とグリセリンとのトリエステルを含むことが好ましい。 The ester preferably includes a triester of a mixed fatty acid of caprylic acid and dodecanoic acid and glycerin from the viewpoint of increasing the flash point, improving lubricity, and improving fluidity at low temperatures.
前記エステル中の前記グリセリントリエステルの含有量は特に制限されないが、引火点を高くし、潤滑性を向上させ、かつ低温での流動性を向上させる観点から、好ましくは８０モル％以上、より好ましくは９０モル％以上、更に好ましくは実質的に１００モル％、より更に好ましくは１００モル％である。なお、本明細書において「実質的に１００モル％」とは不可避的に微量の不純物等を含んでいる状態を言う。 The content of the glycerin triester in the ester is not particularly limited, but from the viewpoint of increasing the flash point, improving lubricity, and improving fluidity at low temperatures, it is preferably 80 mol% or more, more preferably is 90 mol% or more, more preferably substantially 100 mol%, even more preferably 100 mol%. In this specification, "substantially 100 mol%" refers to a state in which a trace amount of impurities is inevitably included.
前記金属加工油用基油は、前記エステル以外の基油を含有してもよい。前記エステル以外の基油としては、例えば、鉱油及び合成油が挙げられる。鉱油としては、例えば、パラフィン基系原油、中間基系原油、又はナフテン基系原油を常圧蒸留するか常圧蒸留の残渣油を減圧蒸留して得られる留出油、あるいはこれを常法にしたがって精製することによって得られる精製油（例えば、溶剤精製油、水添精製油、脱ロウ処理油、白土処理油等）などが挙げられる。また、合成油としては、例えば、本発明の前記エステル以外のエステル、ポリ－α－オレフィン、オレフィンコポリマーアルキルベンゼン、アルキルナフタレン、ポリオキシアルキレングリコール、ポリフェニルエーテルなどが挙げられる。 The base oil for metal working oil may contain a base oil other than the ester. Examples of the base oil other than the ester include mineral oil and synthetic oil. Mineral oils include, for example, distillate oil obtained by atmospheric distillation of paraffinic crude oil, intermediate base crude oil, or naphthenic crude oil, or distillation of residual oil from atmospheric distillation under reduced pressure, or distillate oil obtained by distilling this by a conventional method. Therefore, refined oils obtained by refining (for example, solvent-refined oils, hydrogenated refined oils, dewaxed oils, clay-treated oils, etc.) can be mentioned. Further, examples of the synthetic oil include esters other than the above-mentioned esters of the present invention, poly-α-olefins, olefin copolymers alkylbenzenes, alkylnaphthalenes, polyoxyalkylene glycols, polyphenyl ethers, and the like.
前記金属加工油用基油中の前記エステルの含有量は特に制限されないが、引火点を高くし、潤滑性を向上させ、かつ低温での流動性を向上させる観点から、好ましくは９０質量％以上、より好ましくは９５質量％以上、更に好ましくは実質的に１００質量％、より更に好ましくは１００質量％である。 The content of the ester in the base oil for metal working oil is not particularly limited, but is preferably 90% by mass or more from the viewpoint of increasing the flash point, improving lubricity, and improving fluidity at low temperatures. , more preferably 95% by mass or more, still more preferably substantially 100% by mass, even more preferably 100% by mass.
前記金属加工油用基油の４０℃動粘度は、加工性を向上させる観点から、好ましくは１６ｍｍ２／ｓ以下、より好ましくは１５ｍｍ２／ｓ以下であり、耐摩耗性を向上させる観点から、好ましくは１４ｍｍ２／ｓ以上である。 The 40°C kinematic viscosity of the base oil for metal working oil is preferably 16 mm 2 /s or less, more preferably 15 mm 2 /s or less, from the viewpoint of improving workability, and from the viewpoint of improving wear resistance, Preferably it is 14 mm 2 /s or more.
前記金属加工油用基油の粘度指数は、温度による粘度変化を小さくする観点から、好ましくは１００以上、より好ましくは１２０以上である。 The viscosity index of the base oil for metal working oil is preferably 100 or more, more preferably 120 or more, from the viewpoint of reducing changes in viscosity due to temperature.
前記金属加工油用基油の流動点は、低温での流動性を向上させる観点から、好ましくは－１０℃以下、より好ましくは－１５℃以下である。 The pour point of the base oil for metal working oil is preferably -10°C or lower, more preferably -15°C or lower, from the viewpoint of improving fluidity at low temperatures.
前記金属加工油用基油の引火点は、可燃性を低下させる観点から、好ましくは２５０℃以上である。 The flash point of the base oil for metal working oil is preferably 250° C. or higher from the viewpoint of reducing flammability.
〔エステルの製造方法〕
前記エステルは、前記脂肪酸とグリセリンを、公知の方法に従って、エステル化反応を行うことにより調製することができる。例えば、カプリル酸とグリセリンとのエステル化反応により得られるトリエステルと、ドデカン酸とグリセリンとのエステル化反応により得られるトリエステルとを、特定比率で混合して得る方法、特定比率のカプリル酸とドデカン酸の混合脂肪酸とグリセリンとのエステル化反応により得る方法が挙げられ、低温での流動性を向上させる観点から、特定比率のカプリル酸とドデカン酸の混合脂肪酸とグリセリンとのエステル化反応により得る方法が好ましい。脂肪酸とグリセリンとのエステルにおけるカプリル酸とドデカン酸のモル比は、エステルの調製に用いたカプリル酸とドデカン酸のそれぞれのモル数から計算することができる。
[Method for producing ester]
The ester can be prepared by subjecting the fatty acid and glycerin to an esterification reaction according to a known method. For example, a method of mixing a triester obtained by an esterification reaction of caprylic acid and glycerin with a triester obtained by an esterification reaction of dodecanoic acid and glycerin in a specific ratio, Examples include a method for obtaining dodecanoic acid by an esterification reaction between a mixed fatty acid and glycerin, and from the viewpoint of improving fluidity at low temperatures, it is obtained by an esterification reaction between a mixed fatty acid of caprylic acid and dodecanoic acid in a specific ratio and glycerin. The method is preferred. The molar ratio of caprylic acid and dodecanoic acid in the ester of fatty acid and glycerin can be calculated from the respective moles of caprylic acid and dodecanoic acid used in the preparation of the ester.
前記エステルの製造において、エステル化反応促進の観点から、前記グリセリンの水酸基１当量に対する前記脂肪酸のカルボキシ基を１当量より過剰量を用いてエステル化反応を行う工程と、エステル化反応後に過剰分の脂肪酸を除去する工程を含むことが好ましい。前記脂肪酸のカルボキシ基の当量は、前記グリセリンの水酸基１当量に対して、１．１当量以上が好ましく、そして、脂肪酸を除去する工程での負荷を低減する観点から、１．５当量以下が好ましく、１．３当量以下がより好ましい。得られるエステルの水酸基価が、好ましくは３．０ｍｇＫＯＨ／ｇ以下、より好ましくは１．５ｍｇＫＯＨ／ｇ以下になるまでエステル化反応を行うことが好ましい。エステル化反応後に過剰の脂肪酸を除去する方法としては、例えば、減圧留去、スチーミング、吸着剤を用いた吸着除去などが挙げられる。得られるエステルの酸価が、好ましくは０．３ｍｇＫＯＨ／ｇ以下、より好ましくは０．１ｍｇＫＯＨ／ｇ以下になるまで脂肪酸を除去することが好ましい。 In the production of the ester, from the viewpoint of promoting the esterification reaction, there is a step of carrying out the esterification reaction using an excess of 1 equivalent of the carboxy group of the fatty acid relative to 1 equivalent of the hydroxyl group of the glycerin, and a step of carrying out the esterification reaction using an excess of 1 equivalent of the carboxy group of the fatty acid per 1 equivalent of the hydroxyl group of the glycerin, and Preferably, the method includes a step of removing fatty acids. The equivalent of the carboxy group of the fatty acid is preferably 1.1 equivalent or more, and preferably 1.5 equivalent or less from the viewpoint of reducing the load in the step of removing the fatty acid, with respect to 1 equivalent of the hydroxyl group of the glycerin. , more preferably 1.3 equivalents or less. It is preferable to carry out the esterification reaction until the hydroxyl value of the obtained ester becomes preferably 3.0 mgKOH/g or less, more preferably 1.5 mgKOH/g or less. Examples of methods for removing excess fatty acids after the esterification reaction include distillation under reduced pressure, steaming, and adsorption removal using an adsorbent. It is preferable to remove fatty acids until the acid value of the resulting ester becomes preferably 0.3 mgKOH/g or less, more preferably 0.1 mgKOH/g or less.
具体的には、前記金属加工油用基油の製造方法は、以下の工程１及び工程２を含む。
以下の工程１及び工程２を含む金属加工油用基油の製造方法。
工程１：グリセリンと脂肪酸とのエステル化反応を行う工程であって、前記グリセリンの水酸基１当量に対する前記脂肪酸のカルボキシ基の当量が１．１当量以上であり、前記脂肪酸がカプリル酸とドデカン酸の混合脂肪酸であり、前記脂肪酸中の前記カプリル酸と前記ドデカン酸の合計含有量が、９０モル％以上であり、前記混合脂肪酸中の前記カプリル酸と前記ドデカン酸のモル比（カプリル酸／ドデカン酸）が、７０／３０以上９０／１０以下である工程
工程２：エステル化反応後に過剰分の前記脂肪酸を除去する工程
Specifically, the method for producing the base oil for metal working oil includes the following steps 1 and 2.
A method for producing base oil for metal working oil, including the following steps 1 and 2.
Step 1: A step of performing an esterification reaction between glycerin and a fatty acid, wherein the equivalent of the carboxy group of the fatty acid is 1.1 equivalent or more with respect to 1 equivalent of the hydroxyl group of the glycerin, and the fatty acid is a combination of caprylic acid and dodecanoic acid. It is a mixed fatty acid, and the total content of the caprylic acid and the dodecanoic acid in the fatty acid is 90 mol% or more, and the molar ratio of the caprylic acid and the dodecanoic acid in the mixed fatty acid (caprylic acid/dodecanoic acid ) is 70/30 or more and 90/10 or less Step 2: Step of removing the excess fatty acid after the esterification reaction
＜不水溶性金属加工油組成物＞
本実施形態の不水溶性金属加工油組成物は、少なくとも前記金属加工油用基油を含有する。前記不水溶性金属加工油組成物中の前記金属加工油用基油の含有量は、引火点を高くし、潤滑性を向上させ、かつ低温での流動性を向上させる観点から、好ましくは９０質量％以上であり、より好ましくは実質的に１００質量％以上、更に好ましくは１００質量％である。なお、本明細書において「実質的に１００質量％」とは不可避的に微量の不純物等を含んでいる状態を言う。
<Water-insoluble metal working oil composition>
The water-insoluble metal working oil composition of this embodiment contains at least the base oil for metal working oil. The content of the base oil for metal working oil in the water-insoluble metal working oil composition is preferably 90% from the viewpoint of raising the flash point, improving lubricity, and improving fluidity at low temperatures. It is at least 100% by mass, more preferably substantially at least 100% by mass, and even more preferably 100% by mass. In this specification, "substantially 100% by mass" refers to a state in which a trace amount of impurities and the like are inevitably included.
前記不水溶性金属加工油組成物は、前記金属加工油用基油の他に、一般的な不水溶性金属加工油組成物に配合される添加剤を含有してもよい。前記添加剤としては、例えば、油性剤、極圧剤、界面活性剤、消泡剤、防錆剤、防腐剤、酸化防止剤、及び金属不活性化剤などが挙げられる。これらは１種を単独で用いてもよく、２種以上を併用してもよい。 The water-insoluble metal working oil composition may contain, in addition to the base oil for metal working oil, additives that are blended into general water-insoluble metal working oil compositions. Examples of the additives include oily agents, extreme pressure agents, surfactants, antifoaming agents, rust preventives, preservatives, antioxidants, and metal deactivators. These may be used alone or in combination of two or more.
前記不水溶性金属加工油組成物は、前記金属加工油用基油を含有するため、高い引火点と室温付近での低い粘度を両立し、更に低温での流動性を有するものであり、金属の切削・研削加工などに好適に用いられる。 Since the water-insoluble metal working oil composition contains the base oil for metal working oil, it has both a high flash point and a low viscosity near room temperature, and also has fluidity at low temperatures. Suitable for cutting, grinding, etc.
以下、本発明について、実施例に基づき具体的に説明するが、本発明はこれらの実施例のみに限定されるものではない。また、各種測定、評価方法は以下のとおりである。 EXAMPLES Hereinafter, the present invention will be specifically explained based on Examples, but the present invention is not limited only to these Examples. In addition, various measurement and evaluation methods are as follows.
＜縮合エステルの調製＞
〔実施例１〕
攪拌機、温度計、窒素吹き込み管および冷却管を備えた１リットルの４つ口フラスコに、脂肪酸として、カプリル酸３８７．８１ｇ、ドデカン酸１２４．３２ｇを加えて混合脂肪酸を調製し、さらに、グリセリン１２７．００ｇを添加した。なお、脂肪酸の添加量は、グリセリンの水酸基１当量に対して脂肪酸の総カルボキシ基が０．８当量になるようにした。次に、フラスコ内に、窒素ガスを吹き込み、攪拌しながら２３０℃まで昇温し、５時間２３０℃を維持し、留出する水分を冷却管を用いてフラスコ外へ除去した。反応終了後、追加でカプリル酸２３８．６５ｇを添加し、再度２３０℃まで昇温した。７時間２３０℃を維持し、留出する水分は冷却管を用いてフラスコ外へ除去した。反応終了後、０．１３ｋＰａの減圧下で過剰の脂肪酸を留去し、吸着剤（商品名：キョーワード５００ＳＨ、協和化学工業株式会社製）に残存している脂肪酸を吸着させた後、濾過を行い、縮合エステルを得た。得られた縮合エステルは、酸価が０．１ｍｇＫＯＨ／ｇ未満、水酸基価が１．０ｍｇＫＯＨ／ｇ未満であり、グリセリンの部分エステル、未反応の脂肪酸、未反応のグリセリンのいずれも実質的に含まないことを確認した。得られた縮合エステルは、グリセリンのトリエステルが実質的に１００％であった。得られた縮合エステルは、カプリル酸のトリエステル、ドデカン酸のトリエステル、及びカプリル酸とドデカン酸のトリエステルを含む混合物である。すなわち、得られた縮合エステルは、カプリル酸とドデカン酸の混合脂肪酸とグリセリンとのトリエステルを含む混合物である。
<Preparation of condensed ester>
[Example 1]
A mixed fatty acid was prepared by adding 387.81 g of caprylic acid and 124.32 g of dodecanoic acid as fatty acids to a 1 liter four-necked flask equipped with a stirrer, thermometer, nitrogen blowing tube, and cooling tube, and then adding 127 g of glycerin. .00g was added. The amount of fatty acids added was such that the total amount of carboxy groups in the fatty acids was 0.8 equivalents per 1 equivalent of hydroxyl groups in glycerin. Next, nitrogen gas was blown into the flask, the temperature was raised to 230° C. while stirring, and the temperature was maintained at 230° C. for 5 hours, and distilled water was removed from the flask using a cooling tube. After the reaction was completed, 238.65 g of caprylic acid was additionally added, and the temperature was raised to 230°C again. The temperature was maintained at 230° C. for 7 hours, and the distilled water was removed to the outside of the flask using a cooling tube. After the reaction, excess fatty acids were distilled off under reduced pressure of 0.13 kPa, and the remaining fatty acids were adsorbed on an adsorbent (trade name: Kyoward 500SH, manufactured by Kyowa Chemical Industry Co., Ltd.), followed by filtration. A condensed ester was obtained. The resulting condensed ester has an acid value of less than 0.1 mgKOH/g, a hydroxyl value of less than 1.0 mgKOH/g, and substantially contains no partial ester of glycerin, unreacted fatty acids, or unreacted glycerin. I confirmed that there was no. The resulting condensed ester contained substantially 100% glycerin triester. The resulting condensed ester is a mixture containing a triester of caprylic acid, a triester of dodecanoic acid, and a triester of caprylic acid and dodecanoic acid. That is, the obtained condensed ester is a mixture containing a triester of mixed fatty acids of caprylic acid and dodecanoic acid and glycerin.
〔実施例２及び３、比較例１及び２〕
表１に示したカプリル酸とドデカン酸のモル比に変えた以外は実施例１と同様の方法で実施例２及び３、比較例１及び２に係る縮合エステルを調製した。
[Examples 2 and 3, Comparative Examples 1 and 2]
Condensed esters according to Examples 2 and 3 and Comparative Examples 1 and 2 were prepared in the same manner as in Example 1 except that the molar ratio of caprylic acid and dodecanoic acid was changed as shown in Table 1.
＜評価方法＞
〔脂肪酸結合比率の評価〕
得られた縮合エステルの脂肪酸結合比率は、ガスクロマトグラフィー（以下、ＧＣと省略）により測定した。具体的には、試料１０ｍｇをヘキサン溶媒１ｍＬに溶解させ、ＧＣ測定を行い、得られた各化合物ピークの面積比より算出した。測定に使用した装置および分析条件は次の通りである。
ＧＣ装置：商品名８８９０ ＧＣ Ｓｙｓｔｅｍ（Ａｇｉｌｅｎｔ Ｔｅｃｈｎｏｌｏｇｙ製）
カラム：商品名ＤＢ―１ ３０ｍ×２５０μｍ×０．１μｍ（Ａｇｉｌｅｎｔ Ｔｅｃｈｎｏｌｏｇｙ製）
検出器：水素炎イオン検出器（ＦＩＤ）
インジェクション温度：２７０℃
ディテクター温度：３１０℃
オーブン：６０℃（０ｍｉｎ.）→１０℃／ｍｉｎ.→３００℃→３００℃（３６ｍｉｎ.）
<Evaluation method>
[Evaluation of fatty acid binding ratio]
The fatty acid bond ratio of the obtained condensed ester was measured by gas chromatography (hereinafter abbreviated as GC). Specifically, 10 mg of the sample was dissolved in 1 mL of hexane solvent, GC measurement was performed, and calculation was made from the area ratio of the obtained peaks of each compound. The equipment and analysis conditions used for the measurement are as follows.
GC device: Product name 8890 GC System (manufactured by Agilent Technology)
Column: Product name DB-1 30m x 250μm x 0.1μm (manufactured by Agilent Technology)
Detector: Flame ion detector (FID)
Injection temperature: 270℃
Detector temperature: 310℃
Oven: 60℃ (0min.) → 10℃/min. → 300℃ → 300℃ (36min.)
〔潤滑性（動粘度）の評価〕
動粘度の評価は、ＡＳＴＭ Ｄ７０４２で要求される精度を満たしたスタビンガー動粘度計（商品名：ＳＶＭ３０００、Ａｎｔｏｎ Ｐａａｒ社製）により、４０℃動粘度を測定し潤滑性の評価とした。
[Evaluation of lubricity (kinetic viscosity)]
The kinematic viscosity was evaluated by measuring the kinematic viscosity at 40° C. using a Stabinger kinematic viscometer (trade name: SVM3000, manufactured by Anton Paar) that met the accuracy required by ASTM D7042.
〔流動点の評価〕
流動点の評価は、ＪＩＳ Ｋ２２６９に従った測定方法により流動点（℃）を測定した。
[Evaluation of pour point]
The pour point was evaluated by measuring the pour point (° C.) using a measuring method according to JIS K2269.
〔引火点の評価〕
引火点の評価は、ＪＩＳ Ｋ２２６５に従った測定方法(クリーブランドオープンカップ式)により引火点（℃）を測定した。具体的には、試料を金属カップの標線ぴったりに入れ、クリーブランド開放式 引火点・燃焼点測定器（商品名ＯｐｔｉＦｌａｓｈ、ＰＡＣ製）により測定した。
[Evaluation of flash point]
The flash point was evaluated by measuring the flash point (° C.) using a measuring method (Cleveland open cup method) according to JIS K2265. Specifically, a sample was placed exactly on the marked line of a metal cup and measured using a Cleveland open type flash point/combustion point meter (trade name: OptiFlash, manufactured by PAC).
各評価結果を表１に示す。 The results of each evaluation are shown in Table 1.
表１から、カプリル酸とドデカン酸のモル比（デカン酸／ドデカン酸）が、７０／３０以上９０／１０以下であり、前記脂肪酸中の前記カプリル酸と前記ドデカン酸の合計含有量が、６０モル％以上である実施例１～３の縮合エステルは、０℃動粘度が１６（ｍｍ２／ｓ）以下、かつ引火点が２５０℃以上であり、高い引火点と室温付近での低い粘度を両立するものであることがわかる。また、実施例１～３の縮合エステルは、流動点が－１０℃以下であり、低温での流動性に優れるものである。一方、カプリル酸とドデカン酸のモル比（デカン酸／ドデカン酸）が、７０／３０以上９０／１０以下を満たさない比較例１、２の縮合エステルは、４０℃動粘度が１６（ｍｍ２／ｓ）を超えるか、あるいは引火点が２５０℃未満であり、高い引火点と室温付近での低い粘度を両立することができない。 From Table 1, the molar ratio of caprylic acid and dodecanoic acid (decanoic acid/dodecanoic acid) is 70/30 or more and 90/10 or less, and the total content of the caprylic acid and the dodecanoic acid in the fatty acid is 60 The condensed esters of Examples 1 to 3, which are mol% or more, have a kinematic viscosity of 16 (mm 2 /s) or less at 0°C and a flash point of 250°C or more, and have a high flash point and a low viscosity near room temperature. It turns out that both are compatible. Furthermore, the condensed esters of Examples 1 to 3 have pour points of −10° C. or lower and have excellent fluidity at low temperatures. On the other hand, the condensed esters of Comparative Examples 1 and 2 in which the molar ratio of caprylic acid and dodecanoic acid (decanoic acid/dodecanoic acid) does not satisfy the range of 70/30 to 90/10 have a kinematic viscosity of 16 (mm 2 / s) or the flash point is less than 250° C., making it impossible to achieve both a high flash point and a low viscosity near room temperature.
本発明の不水溶性金属加工油組成物は、金属の切削・研削加工などに好適に用いられる
。
The water-insoluble metal working oil composition of the present invention is suitably used for metal cutting, grinding, and the like.
Claims (5)
前記脂肪酸が、カプリル酸とドデカン酸を含み、前記カプリル酸と前記ドデカン酸のモル比（カプリル酸／ドデカン酸）が、７０／３０以上９０／１０以下であり、
前記脂肪酸中の前記カプリル酸と前記ドデカン酸の合計含有量が、８０モル％以上である、金属加工油用基油。 A base oil for metal working oil containing an ester of fatty acid and glycerin,
The fatty acid contains caprylic acid and dodecanoic acid, and the molar ratio of the caprylic acid and the dodecanoic acid (caprylic acid/dodecanoic acid) is 70/30 or more and 90/10 or less,
A base oil for metal working oil, wherein the total content of the caprylic acid and the dodecanoic acid in the fatty acid is 80 mol% or more.
工程１：グリセリンと脂肪酸とのエステル化反応を行う工程であって、前記グリセリンの水酸基１当量に対する前記脂肪酸のカルボキシ基の当量が１．１当量以上であり、前記脂肪酸がカプリル酸とドデカン酸の混合脂肪酸であり、前記脂肪酸中の前記カプリル酸と前記ドデカン酸の合計含有量が、８０モル％以上であり、前記混合脂肪酸中の前記カプリル酸と前記ドデカン酸のモル比（カプリル酸／ドデカン酸）が、７０／３０以上９０／１０以下である工程
工程２：エステル化反応後に過剰分の前記脂肪酸を除去する工程 A method for producing base oil for metal working oil, including the following steps 1 and 2.
Step 1: A step of performing an esterification reaction between glycerin and a fatty acid, wherein the equivalent of the carboxy group of the fatty acid is 1.1 equivalent or more with respect to 1 equivalent of the hydroxyl group of the glycerin, and the fatty acid is a combination of caprylic acid and dodecanoic acid. It is a mixed fatty acid, and the total content of the caprylic acid and the dodecanoic acid in the fatty acid is 80 mol% or more, and the molar ratio of the caprylic acid and the dodecanoic acid in the mixed fatty acid (caprylic acid/dodecanoic acid) ) is 70/30 or more and 90/10 or less Step 2: Step of removing the excess fatty acid after the esterification reaction
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