JP2017218512A - Synthetic lubricant oil - Google Patents
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- 239000000314 lubricant Substances 0.000 title abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 239000010689 synthetic lubricating oil Substances 0.000 claims description 27
- 239000010687 lubricating oil Substances 0.000 claims description 16
- 239000002199 base oil Substances 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 150000002430 hydrocarbons Chemical group 0.000 abstract description 9
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 238000005461 lubrication Methods 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 2
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 2
- BNXFFWULOXTJHU-UHFFFAOYSA-N 2,4-didecoxy-1-hexylbenzene Chemical compound C(CCCCCCCCC)OC1=CC(=C(C=C1)CCCCCC)OCCCCCCCCCC BNXFFWULOXTJHU-UHFFFAOYSA-N 0.000 description 2
- 239000004101 4-Hexylresorcinol Substances 0.000 description 2
- WFJIVOKAWHGMBH-UHFFFAOYSA-N 4-hexylbenzene-1,3-diol Chemical compound CCCCCCC1=CC=C(O)C=C1O WFJIVOKAWHGMBH-UHFFFAOYSA-N 0.000 description 2
- 235000019360 4-hexylresorcinol Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229960003258 hexylresorcinol Drugs 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- -1 phthalic acid diesters Chemical class 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Landscapes
- Lubricants (AREA)
Abstract
Description
本発明は、各種潤滑油や潤滑油組成物の主要成分などとして有用な合成潤滑油や潤滑油組成物に関する。特に、常温から１００℃を少なくとも多少超える高温での潤滑性が比較的良好で、かつ、エステル結合を有しない合成潤滑油や該合成潤滑油を含む潤滑油組成物に関する。 The present invention relates to a synthetic lubricating oil or lubricating oil composition useful as a main component of various lubricating oils or lubricating oil compositions. In particular, the present invention relates to a synthetic lubricating oil that has relatively good lubricity at room temperature to at least slightly higher than 100 ° C. and has no ester bond, and a lubricating oil composition containing the synthetic lubricating oil.
近年、自動車、家電、電子機器、工業用機械等の様々な産業分野で使用されている装置や機械では、潤滑油の性能向上や適切に調整された潤滑性能が求められている。すなわち、装置や機械の高速化、小型化等の従来装置等の改良だけでなく、様々な分野において新規に開発されたそれぞれの装置や機械に応じて、より過酷な使用条件に耐えうる潤滑性能だけでなく、装置や機械により適切に調整された潤滑性能が必要とされるようになってきている。 In recent years, apparatuses and machines used in various industrial fields such as automobiles, home appliances, electronic devices, and industrial machines have been required to improve the performance of lubricating oil and appropriately adjust the lubrication performance. In other words, not only the improvement of conventional devices such as high speed and downsizing of devices and machines, but also the lubrication performance that can withstand more severe use conditions according to each newly developed device and machine in various fields. In addition, lubrication performance appropriately adjusted by apparatuses and machines has been required.
一般に、潤滑油の基油(「ベースオイル」とも言う。)は、鉱物油と合成油とに分類される。
鉱物油は、石油の潤滑油留分を精製したもので、一般に安価なものであり、従来から現在に至るまで幅広く使用されている(非特許文献１参照)。しかしながら、鉱物油は、耐熱性に劣り、また、酸化、劣化しやすく、耐久性に劣る面が存在する。さらに、分子構造にばらつきがあるため、各々の装置や機械に高度に適合した潤滑性能を得るのが困難化してきている。耐熱性や耐久性を改善するため、各種添加物を配合することもなされているが、装置や機械の種類、用途によっては、添加剤の配合が制約される場合も存在する。
Generally, base oils of lubricating oils (also referred to as “base oils”) are classified into mineral oils and synthetic oils.
Mineral oil is obtained by refining a lubricating oil fraction of petroleum, is generally inexpensive, and has been widely used up to now (see Non-Patent Document 1). However, mineral oil is inferior in heat resistance, easily oxidized and deteriorated, and has a surface inferior in durability. Furthermore, due to variations in the molecular structure, it has become difficult to obtain lubrication performance that is highly compatible with each device and machine. In order to improve heat resistance and durability, various additives are sometimes blended, but depending on the type and use of the apparatus or machine, there are cases where the blending of additives is restricted.
これに対し、合成油は、高度で複雑な過程を経て生成され、不純物が可能な限り排除されており、比較的耐熱性が高くばらつきの少ない潤滑性能が得られるとされている。合成油は、鉱物油に較べコスト高になるものの、今日まで用途や使用態様等に応じて、炭化水素系、エステル系、エーテル系、シリコン系、フッ素系などのものが開発、使用されてきている(非特許文献１参照)。 On the other hand, synthetic oil is produced through an advanced and complicated process, impurities are eliminated as much as possible, and it is said that lubricating performance with relatively high heat resistance and little variation can be obtained. Synthetic oils are more expensive than mineral oils, but hydrocarbon-based, ester-based, ether-based, silicon-based, and fluorine-based oils have been developed and used depending on the application and usage. (See Non-Patent Document 1).
合成油は、上述のとおり、比較的耐熱性が高くばらつきの少ない潤滑性能が得られるが、高温潤滑用途に利用し得る潤滑性能としての、４０℃の動粘度が２０〜４０mm2/secであり、１００℃の動粘度が４.５〜６.５mm2/secである合成油については、フタル酸ジエステル等のエステル系合成油が知られているだけである(例えば、特許文献１〜３、非特許文献１、２参照)。しかしながら、エステル系合成油は、加水分解安定性に劣るため、水分が侵入する可能性がある用途や態様においては利用が望ましくない。 As described above, synthetic oil has relatively high heat resistance and low variation in lubrication performance, but has a kinematic viscosity at 40 ° C. of 20 to 40 mm 2 / sec as a lubrication performance that can be used in high-temperature lubrication applications. As for synthetic oils having a kinematic viscosity at 100 ° C. of 4.5 to 6.5 mm 2 / sec, only ester synthetic oils such as phthalic acid diesters are known (for example, Patent Documents 1 to 3, Non-patent documents 1 and 2). However, ester synthetic oils are inferior in hydrolytic stability, and therefore are not desirably used in applications and embodiments in which moisture may enter.
本発明は、上述のような従来技術やその問題点を背景としてなされたものであり、４０℃の動粘度が２０〜４０mm2/secであり、１００℃の動粘度が４.５〜６.５mm2/secである合成潤滑油であって、エステル結合を有しない合成潤滑油を提供することを課題とする。
また、本発明は、温度による動粘度の変化がエステル系以外の他の合成油に較べて比較的少なく、粘度指数が１２０〜１４０の範囲となる合成潤滑油を提供することを追加的な課題とする。
The present invention has been made against the background of the above-described conventional technology and its problems. The kinematic viscosity at 40 ° C. is 20 to 40 mm 2 / sec, and the kinematic viscosity at 100 ° C. is 4.5 to 6. It is an object of the present invention to provide a synthetic lubricating oil having 5 mm 2 / sec and having no ester bond.
Further, the present invention has an additional problem of providing a synthetic lubricating oil in which the kinematic viscosity change due to temperature is relatively small compared to other synthetic oils other than the ester series, and the viscosity index is in the range of 120 to 140. And
本発明者は、各種の試験、研究過程において、前記課題を解決するために鋭意研究の結果、所定のジアルキルオキシ−ベンゼン構造を有する合成油が４０℃と１００℃の動粘度においてそれぞれ、２０〜４０mm2/sec、４.５〜６.５mm2/secの潤滑性能を発揮することなどを知見した。 As a result of intensive studies in order to solve the above problems in various tests and research processes, the present inventor has found that synthetic oils having a predetermined dialkyloxy-benzene structure have a kinematic viscosity of 40 ° C. and 100 ° C., respectively, at 20 to 20 ° C. and knowledge and to exhibit lubricity of 40mm 2 /sec,4.5~6.5mm 2 / sec.
本発明は、上述の課題の下での前記のような知見に基づいて完成に至ったものであり、本願では、次のような発明が提供される。
＜１＞下記式(１)で表される化合物からなる合成潤滑油。
＜２＞４０℃の動粘度が２０〜４０mm2/secであり、１００℃の動粘度が４.５〜６.５mm2/secである＜１＞に記載の合成潤滑油。
＜３＞粘度指数が１２０〜１４０である＜１＞又は＜２＞に記載の合成潤滑油。
＜４＞＜１＞〜＜３＞のいずれか１項に記載の合成潤滑油を含む潤滑油組成物。
＜５＞＜１＞〜＜３＞のいずれか１項に記載の合成潤滑油を基油とする潤滑油組成物。
The present invention has been completed based on the above-mentioned findings under the above-described problems, and the following invention is provided in the present application.
<1> A synthetic lubricating oil comprising a compound represented by the following formula (1).
<2> 40 kinematic viscosity ° C. is 20 to 40 mm 2 / sec, synthetic lubricating oil according to the kinematic viscosity of 100 ° C. is 4.5~6.5mm 2 / sec <1>.
<3> The synthetic lubricating oil according to <1> or <2>, which has a viscosity index of 120 to 140.
<4> A lubricating oil composition comprising the synthetic lubricating oil according to any one of <1> to <3>.
<5> A lubricating oil composition comprising the synthetic lubricating oil according to any one of <1> to <3> as a base oil.
本発明は、次のような態様を含むことができる。
＜６＞Ｒ1が炭素数７〜１８の直鎖状又は分岐状アルキル基である＜１＞〜＜３＞のいずれか１項に記載の合成潤滑油。
＜７＞Ｒ2が水素原子又は炭素数１〜１０の直鎖状若しくは分岐状アルキル基である＜１＞〜＜３＞、＜６＞のいずれか１項に記載の合成潤滑油。
＜８＞＜６＞又は＜７＞に記載の合成潤滑油を含む潤滑油組成物。
The present invention can include the following aspects.
<6> The synthetic lubricating oil according to any one of <1> to <3>, wherein R 1 is a linear or branched alkyl group having 7 to 18 carbon atoms.
<7> The synthetic lubricant according to any one of <1> to <3>, <6>, wherein R 2 is a hydrogen atom or a linear or branched alkyl group having 1 to 10 carbon atoms.
<8> A lubricating oil composition comprising the synthetic lubricating oil according to <6> or <7>.
本発明の合成潤滑油は、４０℃の動粘度が２０〜４０mm2/secであり、１００℃の動粘度が４.５〜６.５mm2/secであり、温度による動粘度の変化がエステル系以外の他の合成潤滑油に較べて比較的小さく、常温から１００℃を少なくとも多少超える高温の環境において好適に使用することができる。
また、本発明の合成潤滑油は、エステル結合を有しないので、エステル系合成潤滑油におけるような、水が浸入する可能性がある環境下においても加水分解劣化を心配する必要がない。
Synthetic lubricating oils of the present invention has a kinematic viscosity of 40 ° C. is 20 to 40 mm 2 / sec, a kinematic viscosity of 100 ° C. is 4.5~6.5mm 2 / sec, the change in kinematic viscosity with temperature ester It is relatively small compared to other synthetic lubricating oils other than those of the system, and can be suitably used in a high temperature environment that is at least slightly higher than room temperature to 100 ° C.
Moreover, since the synthetic lubricating oil of the present invention does not have an ester bond, there is no need to worry about hydrolysis degradation even in an environment where water may enter, as in the case of an ester synthetic lubricating oil.
本発明の合成潤滑油は、一般式(１)で表される化合物からなるものであり、４０℃の動粘度が２０〜４０mm2/secであり、１００℃の動粘度が４.５〜６.５mm2/secである。
４０℃や１００℃の動粘度の必要とされる範囲に応じて、上記Ｒ1やＲ2は、適宜の炭素数のものや複数の炭素数の組み合わせが選択されうる。
上記Ｒ1は、好ましくは炭素数７〜１８の直鎖状又は分岐状アルキル基であり、より好ましくは炭素数８〜１５の直鎖状アルキル基である。具体的には、ノニル基、デシル基、ウンデシル基、ドデシル基、トリデシル基、テトラデシル基等を挙げることができる。
上記Ｒ2は、好ましくは水素原子又は炭素数１〜１０の直鎖状若しくは分岐状アルキル基であり、より好ましくは水素原子又は炭素数１〜８の直鎖状アルキル基である。
Depending on the range in which the kinematic viscosity at 40 ° C. or 100 ° C. is required, R 1 and R 2 can be selected to have an appropriate number of carbon atoms or a combination of a plurality of carbon numbers.
R 1 is preferably a linear or branched alkyl group having 7 to 18 carbon atoms, and more preferably a linear alkyl group having 8 to 15 carbon atoms. Specific examples include a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, and a tetradecyl group.
R 2 is preferably a hydrogen atom or a linear or branched alkyl group having 1 to 10 carbon atoms, more preferably a hydrogen atom or a linear alkyl group having 1 to 8 carbon atoms.
本発明の合成潤滑油は、どのような方法で製造しても良いが、例えば、非特許文献３に開示された合成法に準じて、下記式(２)のように、４−アルキルレソルシノールと１−ブロモアルカンを反応させることにより製造することができる。 The synthetic lubricating oil of the present invention may be produced by any method. For example, according to the synthesis method disclosed in Non-Patent Document 3, 4-alkylresorcinol is represented by the following formula (2). And 1-bromoalkane can be reacted.
本発明の合成潤滑油は、そのままで潤滑油として使用してもよいし、潤滑油組成物の基油(組成物の５０wt％以上)としても使用できる。また、鉱物油や他の合成油の高温潤滑特性等の改善を目的とした添加成分(潤滑油組成物の例えば１〜４０wt％)として使用することもできる。 The synthetic lubricating oil of the present invention may be used as it is as a lubricating oil or as a base oil of a lubricating oil composition (50 wt% or more of the composition). Moreover, it can also be used as an additive component (for example, 1 to 40 wt% of the lubricating oil composition) for the purpose of improving the high-temperature lubrication characteristics of mineral oil and other synthetic oils.
以下、実施例に基づいて本発明をさらに詳細に説明するが、本発明は、これらの実施例に何ら限定されるものではない。 EXAMPLES Hereinafter, although this invention is demonstrated further in detail based on an Example, this invention is not limited to these Examples at all.
［実施例１］
＜１，３−ジデシルオキシ−４−ヘキシルベンゼン(化合物１ａ：Ｒ1＝デシル、Ｒ2＝ヘキシル)の合成＞
４−ヘキシルレソルシノール９.２０ｇ(４７.４ｍｍｏｌ)、１−ブロモデカン２６.９ｇ(１２２ｍｍｏｌ)、炭酸カリウム１９.７ｇ(１４３ｍｍｏｌ)の混合物にジメチルホルムアミド８５ｍＬを加え、７０℃で８時間撹拌した。反応混合物にヘキサン／ジクロロメタン(３／１)２００ｍＬを加え、減圧濾過し、濾液を水で洗浄した。有機層を無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。残留物をシリカゲルカラムグラフィー(溶出：ヘキサン／ジクロロメタン＝８／１〜７／１)により精製し、化合物１ａ(無色液体)を１８.１ｇ(３８.１ｍｍｍｏｌ、収率８０％)得た。
1Ｈ ＮＭＲ(ＣＤＣｌ3，５００ＭＨｚ)：δ＝０.８５−０.９１(ｍ，９Ｈ)，１.２２−１.５５(ｍ，３６Ｈ)，１.７２−１.８１(ｍ，４Ｈ)，２.５２(ｔ，２Ｈ，Ｊ＝７.７Ｈｚ)，３.９０９(ｔ，２Ｈ，Ｊ＝６.４Ｈｚ)，３.９１４(ｔ，２Ｈ，Ｊ＝６.６Ｈｚ)，６.３７(ｄｄ，１Ｈ，Ｊ＝８.２，２.４Ｈｚ)，６.４１(ｄ，１Ｈ，Ｊ＝２.４Ｈｚ)，６.９８(ｄ，１Ｈ，Ｊ＝８.２Ｈｚ).
13Ｃ ＮＭＲ(ＣＤＣｌ3，１２５ＭＨｚ)：δ＝１４.３１(３Ｃ)，２２.７１(３Ｃ)，２６.１２，２６.２３，２９.３０，２９.３８(３Ｃ)，２９.４１，２９.４５，２９.６７(５Ｃ)，２９.７２，３０.２４，３１.８３，３１.９５(２Ｃ)，６７.７６，６８.０３，９９.６７，１０４.２５，１２３.７８，１２９.７５，１５７.７７，１５８.３９.
[Example 1]
<Synthesis of 1,3-didecyloxy-4-hexylbenzene (Compound 1a: R 1 = decyl, R 2 = hexyl)>
To a mixture of 9.20 g (47.4 mmol) of 4-hexylresorcinol, 26.9 g (122 mmol) of 1-bromodecane and 19.7 g (143 mmol) of potassium carbonate, 85 mL of dimethylformamide was added and stirred at 70 ° C. for 8 hours. To the reaction mixture was added 200 mL of hexane / dichloromethane (3/1), filtered under reduced pressure, and the filtrate was washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution: hexane / dichloromethane = 8/1 to 7/1) to obtain 18.1 g (38.1 mmol, yield 80%) of compound 1a (colorless liquid).
1 H NMR (CDCl 3 , 500 MHz): δ = 0.85-0.91 (m, 9H), 1.22-1.55 (m, 36H), 1.72-1.81 (m, 4H) 2.52 (t, 2H, J = 7.7 Hz), 3.909 (t, 2H, J = 6.4 Hz), 3.914 (t, 2H, J = 6.6 Hz), 6.37 ( dd, 1H, J = 8.2, 2.4 Hz), 6.41 (d, 1H, J = 2.4 Hz), 6.98 (d, 1H, J = 8.2 Hz).
13 C NMR (CDCl 3 , 125 MHz): δ = 14.31 (3C), 22.71 (3C), 26.12, 26.23, 29.30, 29.38 (3C), 29.41, 29 .45, 29.67 (5C), 29.72, 30.24, 31.83, 31.95 (2C), 67.76, 68.03, 99.67, 104.25, 123.78, 129 .75, 157.77, 158.39.
［実施例２］
＜１，３−ジデシルオキシ−４−ヘキシルベンゼン(化合物１ｂ：Ｒ1＝ドデシル、Ｒ2＝ヘキシル)の合成＞
４−ヘキシルレソルシノール７.９６ｇ(４１.０ｍｍｏｌ)、１−ブロモデカン２６.３ｇ(１０５ｍｍｏｌ)、炭酸カリウム１６.６ｇ(１２０ｍｍｏｌ)の混合物にジメチルホルムアミド７５ｍＬを加え、７０℃で８時間撹拌した。反応混合物にヘキサン／ジクロロメタン(３／１)２００ｍＬを加え、減圧濾過し、濾液を水で洗浄した。有機層を無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。残留物をシリカゲルカラムグラフィー(溶出：ヘキサン／ジクロロメタン＝８／１〜７／１)により精製し、化合物１ｂ(無色液体)を１７.６ｇ(３３.２ｍｍｍｏｌ、収率８１％)得た。
1Ｈ ＮＭＲ(ＣＤＣｌ3，５００ＭＨｚ)：δ＝０.８５−０.９１(ｍ，９Ｈ)，１.２２−１.５５(ｍ，４４Ｈ)，１.７２−１.８１(ｍ，４Ｈ)，２.５２(ｔ，２Ｈ，Ｊ＝７.７Ｈｚ)，３.９０８(ｔ，２Ｈ，Ｊ＝６.４Ｈｚ)，３.９１３(ｔ，２Ｈ，Ｊ＝６.６Ｈｚ)，６.３７(ｄｄ，１Ｈ，Ｊ＝８.２，２.４Ｈｚ)，６.４１(ｄ，１Ｈ，Ｊ＝２.４Ｈｚ)，６.９８(ｄ，１Ｈ，Ｊ＝８.２Ｈｚ).
13Ｃ ＮＭＲ(ＣＤＣｌ3，１２５ＭＨｚ)：δ＝１４.３１(３Ｃ)，２２.７２(３Ｃ)，２６.１３，２６.２３，２９.３１，２９.３９(４Ｃ)，２９.４６，２９.６７(９Ｃ)，２９.７３，３０.２４，３１.８３，３１.９６(２Ｃ)，６７.７５，６８.０２，９９.６６，１０４.２４，１２３.７７，１２９.７５，１５７.７７，１５８.３９.
[Example 2]
<Synthesis of 1,3-didecyloxy-4-hexylbenzene (Compound 1b: R 1 = dodecyl, R 2 = hexyl)>
To a mixture of 4-hexylresorcinol 7.96 g (41.0 mmol), 1-bromodecane 26.3 g (105 mmol) and potassium carbonate 16.6 g (120 mmol) was added 75 mL of dimethylformamide, and the mixture was stirred at 70 ° C. for 8 hours. To the reaction mixture was added 200 mL of hexane / dichloromethane (3/1), filtered under reduced pressure, and the filtrate was washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution: hexane / dichloromethane = 8/1 to 7/1) to obtain 17.6 g (33.2 mmol, yield 81%) of compound 1b (colorless liquid).
1 H NMR (CDCl 3 , 500 MHz): δ = 0.85-0.91 (m, 9H), 1.22-1.55 (m, 44H), 1.72-1.81 (m, 4H) 2.52 (t, 2H, J = 7.7 Hz), 3.908 (t, 2H, J = 6.4 Hz), 3.913 (t, 2H, J = 6.6 Hz), 6.37 ( dd, 1H, J = 8.2, 2.4 Hz), 6.41 (d, 1H, J = 2.4 Hz), 6.98 (d, 1H, J = 8.2 Hz).
13 C NMR (CDCl 3 , 125 MHz): δ = 14.31 (3C), 22.72 (3C), 26.13, 26.23, 29.31, 29.39 (4C), 29.46, 29 .67 (9C), 29.73, 30.24, 31.83, 31.96 (2C), 67.75, 68.02, 99.66, 104.24, 123.77, 129.75, 157 .77, 158.39.
［実施例３］
＜化合物１ａ、１ｂの動粘度、粘度指数＞
実施例１、２で製造した化合物１ａ、１ｂについて、動粘度をＪＩＳ Ｋ ２２８３の方法により測定した。また、粘度指数をＪＩＳ Ｋ ２２８３の方法により算出した。化合物１ａ、１ｂの４０℃と１００℃の動粘度と、粘度指数を表１に示す。本発明の実施例の合成潤滑油である化合物１ａ、１ｂは、４０℃と１００℃の動粘度がそれぞれ、２５〜３２mm2/sec程度、５〜６mm2/sec程度で、温度による動粘度の変化が、エステル系を除く他の合成油に較べて比較的小さく、粘度指数も１２０〜１４０程度と比較的大きな値となっている。そのため、本発明の実施例の合成潤滑油は、常温から１００℃を少なくとも多少超える高温の環境において好適に使用することができると考えられる。
[Example 3]
<Kinematic viscosity and viscosity index of compounds 1a and 1b>
The kinematic viscosity of the compounds 1a and 1b produced in Examples 1 and 2 was measured by the method of JIS K 2283. The viscosity index was calculated by the method of JIS K 2283. Table 1 shows the kinematic viscosities and viscosity indices of the compounds 1a and 1b at 40 ° C and 100 ° C. Compounds 1a, 1b, a synthetic lubricating oils embodiment of the present invention, each kinematic viscosity 40 ° C. and 100 ℃, 25~32mm 2 / sec about, at about 5 to 6 mm 2 / sec, the kinematic viscosity with temperature The change is relatively small compared to other synthetic oils excluding the ester series, and the viscosity index is a relatively large value of about 120 to 140. Therefore, it is considered that the synthetic lubricating oil of the examples of the present invention can be suitably used in an environment of high temperature at least slightly exceeding normal temperature to 100 ° C.
［比較例］
＜化合物Ａ〜Ｎの動粘度、粘度指数＞
［化３］中に示される比較例の各種化合物Ａ〜Ｎを合成し、実施例３と同様にして、４０℃と１００℃の動粘度を測定し、粘度指数を算出した。それらの結果を表２に示す。表２から明らかなように、４０℃の動粘度が２０〜４０mm2/secの範囲であり、かつ、１００℃の動粘度が４.５〜６.５mm2/secの範囲のものも多少存在したが(化合物Ｊ、Ｋ)、それらは、いずれもエステル結合を有するもので、加水分解安定性に懸念があるものであった。
[Comparative example]
<Kinematic viscosity and viscosity index of compounds A to N>
Various compounds A to N of Comparative Examples shown in [Chemical Formula 3] were synthesized, and the kinematic viscosities at 40 ° C. and 100 ° C. were measured in the same manner as in Example 3 to calculate the viscosity index. The results are shown in Table 2. As is apparent from Table 2, the kinematic viscosity at 40 ° C. is in the range of 20 to 40 mm 2 / sec, and some of the kinematic viscosity at 100 ° C. is in the range of 4.5 to 6.5 mm 2 / sec. However, (Compounds J and K), all of them had ester bonds, and there was concern about hydrolytic stability.
本発明の合成潤滑油は、そのまま又は潤滑油組成物の基油などとして、常温から１００℃を少なくとも多少超える高温の環境において好適に使用することができる。また、水が浸入する可能性がある環境下においても、加水分解による劣化の恐れなく使用することができる。 The synthetic lubricating oil of the present invention can be suitably used as it is or as a base oil of a lubricating oil composition in a high temperature environment at least slightly higher than room temperature to 100 ° C. Moreover, it can be used without fear of deterioration due to hydrolysis even in an environment where water may enter.
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