JPH0558039B2 - - Google Patents
Info
- Publication number
- JPH0558039B2 JPH0558039B2 JP24977484A JP24977484A JPH0558039B2 JP H0558039 B2 JPH0558039 B2 JP H0558039B2 JP 24977484 A JP24977484 A JP 24977484A JP 24977484 A JP24977484 A JP 24977484A JP H0558039 B2 JPH0558039 B2 JP H0558039B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- lubricating oil
- monoalkylnaphthalene
- synthetic lubricating
- present
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000010689 synthetic lubricating oil Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- -1 polyol esters Chemical class 0.000 description 37
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 20
- 230000003647 oxidation Effects 0.000 description 18
- 238000007254 oxidation reaction Methods 0.000 description 18
- 239000010687 lubricating oil Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 6
- YLZQHQUVNZVGOK-UHFFFAOYSA-N 2-methylnon-1-ene Chemical compound CCCCCCCC(C)=C YLZQHQUVNZVGOK-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920013639 polyalphaolefin Polymers 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- IAUKWGFWINVWKS-UHFFFAOYSA-N 1,2-di(propan-2-yl)naphthalene Chemical compound C1=CC=CC2=C(C(C)C)C(C(C)C)=CC=C21 IAUKWGFWINVWKS-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- PVAPJEBDTSVWFD-UHFFFAOYSA-N 2-(2-methylheptan-2-yl)naphthalene Chemical compound C1=CC=CC2=CC(C(C)(C)CCCCC)=CC=C21 PVAPJEBDTSVWFD-UHFFFAOYSA-N 0.000 description 1
- CMMITBUEUSCFJC-UHFFFAOYSA-N 2-(2-methylundecan-2-yl)naphthalene Chemical compound C1=CC=CC2=CC(C(C)(C)CCCCCCCCC)=CC=C21 CMMITBUEUSCFJC-UHFFFAOYSA-N 0.000 description 1
- RCBGGJURENJHKV-UHFFFAOYSA-N 2-methylhept-1-ene Chemical compound CCCCCC(C)=C RCBGGJURENJHKV-UHFFFAOYSA-N 0.000 description 1
- SJVKHZYVCVKEGM-UHFFFAOYSA-N 2-methylundec-1-ene Chemical compound CCCCCCCCCC(C)=C SJVKHZYVCVKEGM-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000010725 compressor oil Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 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 1
- 239000003599 detergent Substances 0.000 description 1
- 239000010710 diesel engine oil Substances 0.000 description 1
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 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 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000010711 gasoline engine oil Substances 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 239000000203 mixture Substances 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
- 239000012299 nitrogen atmosphere Substances 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
- 125000002347 octyl 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])[H] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000002958 pentadecyl 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])C([H])([H])[H] 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005377 tertiary alkyl halides Chemical class 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
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 239000010723 turbine oil Substances 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
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Lubricants (AREA)
Description
（発明の技術分野）
本発明は新規な合成潤滑油に関し、さらに詳し
くは特定の構造を有するモノアルキルナフタレン
を主成分とする、酸化安定性に特に優れた新規な
合成潤滑油に関する。
（発明の背景）
潤滑油は一般に長期間の使用に耐えうることが
要求される。そのため通常は潤滑油として高度に
精製された鉱油に必要に応じて適当な酸化防止剤
を配合したものが使用されている。しかし、鉱油
はその酸化安定性に限界があり、温度条件が厳し
い環境下で、長期間使用することは困難である。
そこでより酸化安定性に優れた潤滑油としてジエ
ステル、ポリオールエステルなどのエステル系合
成潤滑油やポリ−α−オレフイン、アルキルベン
ゼンなどの炭化水素系合成油が開発され、現在広
く使用されている。
しかし、これら従来公知の合成潤滑油は鉱油よ
り酸化安定性が高いとされているものの、その酸
化安定性は満足できるものではなかつた。
本発明者らはより高い酸化安定性を有する合成
潤滑油を開発すべく研究を重ねた結果、特定の構
造を有するモノアルキルナフタレンを主成分とす
る合成潤滑油が、公知の合成潤滑油と比較して格
段に高い酸化安定性を有することを見い出し、本
発明を完成するに至つた。
（発明の目的）
本発明は、特に酸化安定性に優れた合成潤滑油
を提供することを目的とする。
（発明の構成）
本発明の合成潤滑油は、一般式
（式中、R1，R2およびR3はそれぞれ炭素数１
〜21のアルキル基であり、かつR1，R2およびR3
の合計炭素数は５〜23である）
で表わされるモノアルキルナフタレンからなる
か、またはこれを主成分としてなることを特徴と
する。
以下、本発明の内容をより詳細に説明する。
本発明の合成潤滑油の主成分であるアルキルナ
フタレンは、
モノアルキルナフタレンであること、
一般式
(Technical Field of the Invention) The present invention relates to a new synthetic lubricating oil, and more particularly to a new synthetic lubricating oil which has particularly excellent oxidative stability and whose main component is monoalkylnaphthalene having a specific structure. (Background of the Invention) Lubricating oils are generally required to withstand long-term use. Therefore, highly refined mineral oil mixed with an appropriate antioxidant as required is usually used as a lubricating oil. However, mineral oil has a limited oxidation stability, and it is difficult to use it for a long period of time in an environment with severe temperature conditions.
Therefore, as lubricating oils with better oxidation stability, ester-based synthetic lubricating oils such as diesters and polyol esters, and hydrocarbon-based synthetic oils such as poly-α-olefins and alkylbenzenes have been developed and are now widely used. However, although these conventionally known synthetic lubricating oils are said to have higher oxidation stability than mineral oils, their oxidation stability has not been satisfactory. As a result of repeated research to develop a synthetic lubricating oil with higher oxidation stability, the inventors of the present invention found that a synthetic lubricating oil whose main component is monoalkylnaphthalene with a specific structure was compared with known synthetic lubricating oils. The present inventors have discovered that they have significantly high oxidation stability, and have completed the present invention. (Objective of the Invention) An object of the present invention is to provide a synthetic lubricating oil particularly excellent in oxidation stability. (Structure of the Invention) The synthetic lubricating oil of the present invention has the general formula (In the formula, R 1 , R 2 and R 3 each have 1 carbon number
~21 alkyl groups, and R 1 , R 2 and R 3
The total number of carbon atoms is 5 to 23). Hereinafter, the content of the present invention will be explained in more detail. The alkylnaphthalene, which is the main component of the synthetic lubricating oil of the present invention, must be a monoalkylnaphthalene and have the general formula
【式】で表わされるアルキル基
のR1，R2およびR3はそれぞれ炭素数１〜21を
有し、かつR1，R2およびR3の合計炭素数が５
〜23であること、
ナフタレン環に直接結合するアルキル基が第
３級アルキル基であること、
の３点を満たすものであることが必要である。上
記３点のうちどれか１点でも要件を満たしていな
いアルキルナフタレンでは、本発明で使用するア
ルキルナフタレンと比べて酸化安定性や潤滑油と
しての物理的特性が劣るため好ましくない。
本発明で用いるモノアルキルナフタレンとして
は一般式
で表わされるα−置換モノアルキルナフタレンで
も、一般式
で表わされるβ−置換モノアルキルナフタレンで
も使用することができるが、入手の容易さ、化合
物としての安定性などの点からβ−置換モノアル
キルナフタレンを用いるのが好ましい。
一方、一般式R 1 , R 2 and R 3 of the alkyl group represented by [Formula] each have 1 to 21 carbon atoms, and the total number of carbon atoms of R 1 , R 2 and R 3 is 5.
23, and the alkyl group directly bonded to the naphthalene ring is a tertiary alkyl group. Alkylnaphthalenes that do not satisfy any one of the above three requirements are not preferred because they have inferior oxidation stability and physical properties as a lubricating oil compared to the alkylnaphthalenes used in the present invention. The monoalkylnaphthalene used in the present invention has the general formula Even α-substituted monoalkylnaphthalenes represented by the general formula Although β-substituted monoalkylnaphthalenes represented by the formula can also be used, it is preferable to use β-substituted monoalkylnaphthalenes from the viewpoint of ease of availability and stability as a compound. On the other hand, the general formula
【式】で表わされる第３級
アルキル基を構成するR1，R2およびR3はそれぞ
れ炭素数１〜21のアルキル基であり、かつR1，
R2およびR3の合計炭素数が５〜23であることが
必要であるが、モノアルキルナフタレンの潤滑油
用としての物理的特性の面からR1，R2およびR3
が炭素数１〜15のアルキル基であり、かつその合
計炭素数が７〜17が好ましい。またその酸化安定
性の点から、R1，R2およびR3がそれぞれ直鎖ア
ルキル基であるものが好ましい。
本発明で使用するモノアルキルナフタレンにお
いて、R1，R2およびR3としては、具体的には、
例えばメチル基、エチル基、プロピル基、ブチル
基、ペンチル基、ヘキシル基、ヘプチル基、オク
チル基、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、ペン
タデシル基などが好ましく用いられる。
さらに本発明で使用するモノアルキルナフタレ
ンにおいて、特にR1とR2がメチル基またはエチ
ル基であり、R3はR1，R2およびR3の合計炭素が
７〜17となるような炭素数の直鎖アルキル基であ
るものがより好ましい。
本発明におけるモノアルキルナフタレンの一般
式R 1 , R 2 and R 3 constituting the tertiary alkyl group represented by the formula are each an alkyl group having 1 to 21 carbon atoms, and R 1 ,
It is necessary that the total carbon number of R 2 and R 3 is 5 to 23, but from the viewpoint of physical properties of monoalkylnaphthalene for lubricating oil, R 1 , R 2 and R 3 are
is an alkyl group having 1 to 15 carbon atoms, and the total number of carbon atoms is preferably 7 to 17. Further, from the viewpoint of oxidative stability, it is preferable that R 1 , R 2 and R 3 are each a straight-chain alkyl group. In the monoalkylnaphthalene used in the present invention, R 1 , R 2 and R 3 are specifically:
For example, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc. are preferably used. . Furthermore, in the monoalkylnaphthalene used in the present invention, in particular, R 1 and R 2 are methyl groups or ethyl groups, and R 3 has a carbon number such that the total carbon number of R 1 , R 2 and R 3 is 7 to 17. More preferably, it is a straight chain alkyl group. General formula of monoalkylnaphthalene in the present invention
【式】で表わされる第３級アルキル基の
好ましいものとしては、具体的には例えば１，１
−ジメチルヘキシル基、１−エチル−１−メチル
ペンチル基、１，１−ジエチルブチル基、１，１
−ジメチルヘプチル基、１−エチル−１−メチル
ヘキシル基、１，１−ジエチルペンチル基、１，
１−ジメチルオクチル基、１−エチル−１−メチ
ルヘプチル基、１，１−ジエチルヘキシル基、
１，１−ジメチルノニル基、１−エチル−１−メ
チルオクチル基、１，１−ジエチルヘプチル基、
１，１−ジメチルデシル基、１−エチル−１−メ
チルノニル基、１，１−ジエチルオクチル基、
１，１−ジメチルウンデシル基、１−エチル−１
−メチルデシル基、１，１−ジエチルノニル基、
１，１−ジメチルドデシル基、１−エチル−１−
メチルウンデシル基、１，１−ジエチルデシル
基、１，１−ジメチルトリデシル基、１−エチル
−１−メチルドデシル基、１，１−ジエチルウン
デシル基、１，１−ジメチルテトラデシル基、１
−エチル−１−メチルトリデシル基、１、１−ジ
エチルドデシル基、１、１−ジメチルペンタデシ
ル基、１−エチル−１−メチルテトラデシル基、
１，１−ジエチルトリデシル基、１，１−ジメチ
ルヘキサデシル基、１−エチル−１−メチルペン
タデシル基、１，１−ジエチルテトラデシル基な
どが挙げられる。
本発明における第３級アルキル基を有するモノ
アルキルナフタレンは通常、フリーデル・クラフ
ツ（Friedel−Crafts）アルキル化反応により合
成できる。すなわちアルキル源として炭素数６〜
24の第３級アルキルハライド、アルコールや二重
結合位が分枝した炭素上にある炭素数６〜24の分
枝モノオレフインのいずれかを、好ましくは分枝
モノオレフインをナフタレンと塩化アルミニウ
ム、塩化亜鉛、塩化鉄などの金属ハロゲン化物、
硫酸、リン酸、五酸化リン、フツ酸、フツ化ホウ
素、酸性白土、活性白土などの酸性触媒の存在下
で反応温度０〜250℃で反応させることにより得
られる。しかしフリーデル・クラフツアルキル化
反応では立体障害などの影響で炭素陽イオンの転
移が起こり、必ずしも第３級アルキル基だけでな
く第２級アルキル基を有するモノアルキルナフタ
レンも生成する可能性があるという欠点がある。
したがつて第３級アルキル基みを有するモノアル
キルナフタレンを得るためには、他にナフタレン
をアシル化し、この生成物をトリメチルアルミニ
ウムで徹底メチル化する方法、第２級アルキル基
を有するモノアルキルナフタレンの分枝位置の炭
素原子に結合した水素原子をハロゲン置換し、ト
リアルキルアルミニウムと反応させる方法なども
ある。
上記のフリーデル・クラフツアルキル化反応で
第３級アルキル基を有するモノアルキルナフタレ
ンを合成する場合、ナフタレン環の８位の水素原
子との立体障害の影響からβ−置換体が主成分と
して生成する。
上記のモノアルキルナフタレンを主成分とする
本発明の合成潤滑油は単独でも通常の潤滑油に要
求される各種性状とともに酸化安定性が特に良い
という優れた性状を兼ね備えているが、本発明の
合成潤滑油に必要に応じて通常使用されている公
知の潤滑油添加剤、たとえば酸化防止剤、清浄分
散剤、粘度指数向上剤、流動点降下剤、油性剤、
耐摩耗性剤、極圧剤、腐食防止剤、金属不活性化
剤、さび止め剤、消泡剤、乳化剤、抗乳化剤、殺
菌剤、着色剤などを添加してもよい。これら各種
添加剤の詳細は、例えば“潤滑油学会誌、第15
巻、第６号”または“桜井俊男編著、「石油製品
添加剤」（幸書房）”などに記載されている。
また本発明の合成潤滑油はその高い酸化安定性
を損ねない範囲において、必要に応じて鉱油や公
知の合成潤滑油を75重量％以下、好ましくは50重
量％以下、特に好ましくは25重量％以下混合する
ことも可能である。
本発明のモノアルキルナフタレンを主成分とす
る合成潤滑油は、例えばガソリンエンジン油、デ
イーゼルエンジン油、タービン油、ギヤー油、油
圧作動油、圧縮機油、金属加工油、すべり案内面
油、軸受油などに利用できる。
（発明の実施例）
以下、本発明の内容を実施例および比較例によ
りさらに具体的に説明する。
実施例 １
４つ口フラスコにナフタレン700重量部を秤量
し、窒素雰囲気下で攪拌しながら150℃まで加熱
し、さらに220℃で焼成した活性白土100重量部を
添加して200℃まで加熱した。そこへ２−メチル
−１−ノネン500重量部を４時間かけて少量ずつ
滴下し、その後200℃に保つたまま１時間攪拌を
続け、ナフタレンと２−メチル−１−ノネンを反
応させた。
反応終了後、生成混合物を100℃に冷却してろ
過し、ろ液を減圧蒸溜してβ−（１，１−ジメチ
ルオクチル）ナフタレンを得た。このβ−（１，
１−ジメチルオクチル）ナフタレンの性状を示
す。
粘 度：14.86 cSt、＠40℃、
流動点：−45℃以下、
沸 点：165℃／１mmＨｇ、
実施例 ２
２−メチル−１−ノネンの代わりに２−メチル
−１−ヘプテンを用い、他は実施例１と同様の手
法でナフタレンのアルキル化を行い、減圧蒸溜に
よりβ−（１，１−ジメチルヘキシル）ナフタレ
ンを得た。このβ−（１，１−ジメチルヘキシル）
ナフタレンの性状を示す。
粘 度：10.65 cSt、＠40℃、
流動点：−45℃以下、
沸 点：144℃／１mmＨｇ、
実施例 ３
２−メチル−１−ノネンの代わりに２−メチル
−１−ウンデセンを用い、他は実施例１と同様の
手法でナフタレンのアルキル化を行い、減圧蒸溜
によりβ−（１，１−ジメチルデシル）ナフタレ
ンを得た。このβ−（１，１−ジメチルデシル）
ナフタレンの性状を示す。
粘 度：17.63 cSt、＠40℃、
流動点：−45℃以下、
沸 点：185℃／１mmＨｇ、
実験（実施例１〜３および比較例１〜４の化合
物）
上記の実施例１〜３により得られた本発明にか
かるモノアルキルナフタレンおよび比較のため平
均分子量約500のデセン−１オリゴマー（比較例
１）、ジオクチルセバケート（比較例２）、ペンタ
エリスリトールテトラカプリエート（比較例３）
およびジイソプロピルナフタレン（比較例４）の
酸化安定性を評価するため、IP−280に規定され
る試験設備を用いて以下の条件で高温酸化試験を
行つた。
試験温度：170℃、
酸素流量：３／hr
触 媒：銅線 １mmφ×80cm
なお、酸化安定性の評価は、試料油の酸価が
1.0mgKOH／ｇとなつた時間を酸化試験寿命と定
義して行つた。その結果を第１表に示す。Preferred examples of the tertiary alkyl group represented by the formula include, for example, 1,1
-dimethylhexyl group, 1-ethyl-1-methylpentyl group, 1,1-diethylbutyl group, 1,1
-dimethylheptyl group, 1-ethyl-1-methylhexyl group, 1,1-diethylpentyl group, 1,
1-dimethyloctyl group, 1-ethyl-1-methylheptyl group, 1,1-diethylhexyl group,
1,1-dimethylnonyl group, 1-ethyl-1-methyloctyl group, 1,1-diethylheptyl group,
1,1-dimethyldecyl group, 1-ethyl-1-methylnonyl group, 1,1-diethyloctyl group,
1,1-dimethylundecyl group, 1-ethyl-1
-methyldecyl group, 1,1-diethylnonyl group,
1,1-dimethyldodecyl group, 1-ethyl-1-
Methylundecyl group, 1,1-diethyldecyl group, 1,1-dimethyltridecyl group, 1-ethyl-1-methyldodecyl group, 1,1-diethylundecyl group, 1,1-dimethyltetradecyl group, 1
-ethyl-1-methyltridecyl group, 1,1-diethyldodecyl group, 1,1-dimethylpentadecyl group, 1-ethyl-1-methyltetradecyl group,
Examples include 1,1-diethyltridecyl group, 1,1-dimethylhexadecyl group, 1-ethyl-1-methylpentadecyl group, and 1,1-diethyltetradecyl group. The monoalkylnaphthalene having a tertiary alkyl group in the present invention can usually be synthesized by a Friedel-Crafts alkylation reaction. In other words, the alkyl source has 6 or more carbon atoms.
24 tertiary alkyl halides, alcohols or any branched monoolefins having 6 to 24 carbon atoms in which the double bond position is on the branched carbon, preferably branched monoolefins, with naphthalene and aluminum chloride, chloride Metal halides such as zinc and iron chloride,
It is obtained by reacting at a reaction temperature of 0 to 250°C in the presence of an acidic catalyst such as sulfuric acid, phosphoric acid, phosphorus pentoxide, hydrofluoric acid, boron fluoride, acid clay, activated clay, or the like. However, in the Friedel-Crafts alkylation reaction, carbon cations are transferred due to steric hindrance, and it is possible that monoalkylnaphthalenes containing not only tertiary alkyl groups but also secondary alkyl groups are produced. There are drawbacks.
Therefore, in order to obtain a monoalkylnaphthalene having a tertiary alkyl group, another method is to acylate naphthalene and thoroughly methylate the product with trimethylaluminum. There is also a method in which the hydrogen atom bonded to the carbon atom at the branch position is substituted with halogen and reacted with trialkylaluminum. When monoalkylnaphthalenes having a tertiary alkyl group are synthesized by the above Friedel-Crafts alkylation reaction, β-substituted products are produced as the main component due to steric hindrance with the hydrogen atom at the 8-position of the naphthalene ring. . The synthetic lubricating oil of the present invention containing the above-mentioned monoalkylnaphthalene as a main component has excellent properties such as particularly good oxidation stability as well as various properties required for ordinary lubricating oils even when used alone. Known lubricating oil additives commonly used as needed in lubricating oils, such as antioxidants, detergent dispersants, viscosity index improvers, pour point depressants, oiliness agents,
Antiwear agents, extreme pressure agents, corrosion inhibitors, metal deactivators, rust inhibitors, antifoaming agents, emulsifiers, demulsifiers, bactericides, colorants, etc. may be added. For details on these various additives, see, for example, "Journal of the Japan Society of Lubricating Oil, Vol. 15"
Volume, No. 6'' or ``Petroleum Product Additives'' edited by Toshio Sakurai (Saiwai Shobo).The synthetic lubricating oil of the present invention may be used as long as it does not impair its high oxidation stability. Depending on the situation, it is also possible to mix up to 75% by weight, preferably up to 50% by weight, particularly preferably up to 25% by weight of mineral oil or known synthetic lubricating oil. The lubricating oil can be used, for example, as gasoline engine oil, diesel engine oil, turbine oil, gear oil, hydraulic oil, compressor oil, metal working oil, sliding guideway oil, bearing oil, etc. (Embodiments of the Invention) The following is an example of the lubricating oil. The content of the present invention will be explained in more detail with reference to Examples and Comparative Examples.Example 1 700 parts by weight of naphthalene was weighed in a four-necked flask, heated to 150°C with stirring under a nitrogen atmosphere, and further heated to 220°C. Added 100 parts by weight of activated clay calcined at 200°C and heated to 200°C.Added 500 parts by weight of 2-methyl-1-nonene dropwise little by little over 4 hours, and then stirred for 1 hour while maintaining the temperature at 200°C. Then, naphthalene and 2-methyl-1-nonene were reacted. After the reaction was completed, the product mixture was cooled to 100°C and filtered, and the filtrate was distilled under reduced pressure to obtain β-(1,1-dimethyloctyl). Naphthalene was obtained. This β-(1,
The properties of 1-dimethyloctyl)naphthalene are shown. Viscosity: 14.86 cSt, @40℃, Pour point: -45℃ or less, Boiling point: 165℃/1mmHg, Example 2 Using 2-methyl-1-heptene instead of 2-methyl-1-nonene, etc. Naphthalene was alkylated in the same manner as in Example 1, and β-(1,1-dimethylhexyl)naphthalene was obtained by distillation under reduced pressure. This β-(1,1-dimethylhexyl)
Shows the properties of naphthalene. Viscosity: 10.65 cSt, @40℃, Pour point: -45℃ or less, Boiling point: 144℃/1mmHg, Example 3 Using 2-methyl-1-undecene instead of 2-methyl-1-nonene, etc. Naphthalene was alkylated in the same manner as in Example 1, and β-(1,1-dimethyldecyl)naphthalene was obtained by distillation under reduced pressure. This β-(1,1-dimethyldecyl)
Shows the properties of naphthalene. Viscosity: 17.63 cSt, @40°C, Pour point: -45°C or less, Boiling point: 185°C/1 mmHg, Experiment (compounds of Examples 1 to 3 and Comparative Examples 1 to 4) According to Examples 1 to 3 above The obtained monoalkylnaphthalene according to the present invention and, for comparison, decene-1 oligomer with an average molecular weight of about 500 (Comparative Example 1), dioctyl sebacate (Comparative Example 2), and pentaerythritol tetracapriate (Comparative Example 3)
In order to evaluate the oxidation stability of and diisopropylnaphthalene (Comparative Example 4), a high temperature oxidation test was conducted under the following conditions using test equipment specified in IP-280. Test temperature: 170℃, Oxygen flow rate: 3/hr Catalyst: Copper wire 1mmφ
The oxidation test life was defined as the time when the value reached 1.0 mgKOH/g. The results are shown in Table 1.
【表】
第１表の酸化試験寿命の結果から明らかなよう
に、本発明にかかるモノアルキルナフタレンから
なる合成潤滑油は非常に高い高温酸化安定性を示
している。それに対して、従来より酸化安定性に
優れるといわれているポリ−α−オレフイン、ジ
エステル、ポリエステル、アルキルナフタレンな
どの化合物は、酸化試験寿命が本発明の化合物よ
り大きく劣つている。
このように本発明のモノアルキルナフタレンを
主成分とする合成潤滑油は従来公知の他の合成潤
滑油では到達し得ない高い酸化安定性を有するも
のである。[Table] As is clear from the oxidation test life results in Table 1, the synthetic lubricating oil comprising monoalkylnaphthalene according to the present invention exhibits extremely high high temperature oxidation stability. On the other hand, compounds such as poly-α-olefins, diesters, polyesters, and alkylnaphthalenes, which are conventionally said to have excellent oxidation stability, have significantly inferior oxidation test life to the compounds of the present invention. As described above, the synthetic lubricating oil containing monoalkylnaphthalene as a main component of the present invention has high oxidation stability that cannot be achieved by other conventionally known synthetic lubricating oils.
Claims (1)
〜21のアルキル基であり、かつR1，R2およびR3
の合計炭素数は５〜23である） で表わされるモノアルキルナフタレンからなる
か、またはこれを主成分とする合成潤滑油。 ２ 前記モノアルキルナフタレンが一般式 （式中、R1，R2およびR3はそれぞれ炭素数１
〜21のアルキル基であり、かつR1，R2およびR3
の合計炭素数は５〜23である） で表わされるβ−置換モノアルキルナフタレンで
あることを特徴とする特許請求の範囲第１項記載
の合成潤滑油。 ３ 前記R1，R2およびR3がそれぞれ直鎖アルキ
ル基であることを特徴とする特許請求の範囲第１
項または第２項に記載の合成潤滑油。[Claims] 1. General formula (In the formula, R 1 , R 2 and R 3 each have 1 carbon number
~21 alkyl groups, and R 1 , R 2 and R 3
A synthetic lubricating oil consisting of a monoalkylnaphthalene represented by (the total number of carbon atoms is 5 to 23) or having this as a main component. 2 The monoalkylnaphthalene has the general formula (In the formula, R 1 , R 2 and R 3 each have 1 carbon number
~21 alkyl groups, and R 1 , R 2 and R 3
The synthetic lubricating oil according to claim 1, wherein the synthetic lubricating oil is a β-substituted monoalkylnaphthalene represented by (the total number of carbon atoms is 5 to 23). 3. Claim 1, wherein each of R 1 , R 2 and R 3 is a straight-chain alkyl group.
Synthetic lubricating oil according to item 1 or 2.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24977484A JPS61127796A (en) | 1984-11-28 | 1984-11-28 | Synthetic lubricant oil |
| GB08516036A GB2163774B (en) | 1984-07-05 | 1985-06-25 | Synthetic lubricating oils |
| DE19853524188 DE3524188A1 (en) | 1984-07-05 | 1985-07-05 | SYNTHETIC LUBRICANTS |
| US07/008,303 US4737297A (en) | 1984-07-05 | 1987-01-29 | Synthetic lubricating oils |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24977484A JPS61127796A (en) | 1984-11-28 | 1984-11-28 | Synthetic lubricant oil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61127796A JPS61127796A (en) | 1986-06-16 |
| JPH0558039B2 true JPH0558039B2 (en) | 1993-08-25 |
Family
ID=17198022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24977484A Granted JPS61127796A (en) | 1984-07-05 | 1984-11-28 | Synthetic lubricant oil |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61127796A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080234157A1 (en) * | 2007-03-20 | 2008-09-25 | Yoon Beth A | Alkylaromatic lubricant fluids |
-
1984
- 1984-11-28 JP JP24977484A patent/JPS61127796A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61127796A (en) | 1986-06-16 |
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