JPH0425994B2 - - Google Patents
Info
- Publication number
- JPH0425994B2 JPH0425994B2 JP59137887A JP13788784A JPH0425994B2 JP H0425994 B2 JPH0425994 B2 JP H0425994B2 JP 59137887 A JP59137887 A JP 59137887A JP 13788784 A JP13788784 A JP 13788784A JP H0425994 B2 JPH0425994 B2 JP H0425994B2
- Authority
- JP
- Japan
- Prior art keywords
- oil
- synthetic lubricating
- present
- oxidation stability
- lubricating oil
- 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 18
- KUWXWSOGHBXOGK-UHFFFAOYSA-N 2-(2-methylbutan-2-yl)naphthalene Chemical group C1=CC=CC2=CC(C(C)(C)CC)=CC=C21 KUWXWSOGHBXOGK-UHFFFAOYSA-N 0.000 claims description 9
- 230000003647 oxidation Effects 0.000 description 18
- 238000007254 oxidation reaction Methods 0.000 description 18
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 7
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 6
- 239000010687 lubricating oil Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- -1 polyol esters Chemical class 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 2
- 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
- 239000002253 acid Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 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
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 229920013639 polyalphaolefin Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 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
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001336 alkenes 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
- 238000009835 boiling Methods 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
- 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
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation 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
- 239000010720 hydraulic oil Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 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
- 239000000463 material Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003209 petroleum derivative Substances 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
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- CRNIHJHMEQZAAS-UHFFFAOYSA-N tert-amyl chloride Chemical compound CCC(C)(C)Cl CRNIHJHMEQZAAS-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000010723 turbine oil Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Lubricants (AREA)
Description
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ナフタレン誘導体を主成
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。
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なかつた。
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。
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
造を有するナフタレン誘導体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。
すなわち本発明は、２−ｔ−アミルナフタレン
を主成分とする合成潤滑油を提供するものであ
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は下記の構造式で示される
２−ｔ−アミルナフタレンを主成分とするもので
ある。
この化合物の合成法は任意であるが、例えばナ
フタレンとｔ−アミルクロライドとをフリーデル
クラフツ型触媒の存在下で反応させたり、またナ
フタレンと２−メチル−１−ブテンや２−メチル
−２−ブテンとをアルキル化剤の存在下で反応さ
せることにより得られる。反応温度は通常20〜
250℃である。またフリーデルクラフツ型触媒と
しては、例えば塩化アルミニウム、塩化亜鉛、塩
化鉄などが挙げられる。アルキル化剤としては、
例えば上記のフリーデルクラフツ型触媒や硫酸、
リン酸、五酸化リン、フツ酸、酸性白土、活性白
土などの酸性触媒が挙げられる。
通常、本発明のナフタレン誘導体の合成法とし
ては、原料の入手が容易な点などから、ナフタレ
ンと２−メチル−１−ブテンや２−メチル−２−
ブテンなどのオレフイン、特に２−メチル−２−
ブテンとを反応させる方法が最も好ましい。
本発明のナフタレン誘導体を主成分とする合成
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混合することも可能である。
本発明のナフタレン誘導体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。
以下、本発明の内容を合成例、実施例および比
較例によりさらに具体的に説明する。
合成例
４つ口フラスコにナフタレン1000重量部を秤量
し、窒素雰囲気下で撹拌しながら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
−２−ブテン300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時間撹拌を
続けナフタレンと２−メチル−２−ブテンを反応
させた。
反応終了後、生成混合物を100℃に冷却してろ
過し、ろ液を減圧蒸留して目的とする２−ｔ−ア
ミルナフタレンを得た。２−メチル−２−ブテン
をベースとする収率は76％だつた。なお、得られ
た２−ｔ−アミルナフタレンの性状を以下に示
す。
粘 度：5.2cSt、40℃、
：1.5cSt、100℃、
流動点：＜−45℃、
沸 点：128℃、2.0mmHg、
実施例１および比較例１〜５
上記合成例により得られた２−ｔ−アミルナフ
タレン（実施例１）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）、ジイソ
プロピルナフタレン（比較例４）、ポリｔ−アミ
ルナフタレン（比較例５）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。
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 a naphthalene derivative having a specific structure. 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, ester-based synthetic lubricating oils such as diesters and polyol esters, and hydrocarbon-based synthetic oils such as polyα-olefins have been developed as lubricating oils with better oxidation stability, 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. An object of the present invention is to provide a synthetic lubricating oil that has particularly excellent oxidation stability. As a result of repeated research aimed at developing synthetic lubricating oils with higher oxidation stability, the inventors of the present invention found that synthetic lubricating oils containing naphthalene derivatives having a specific structure as a main component compared to known synthetic lubricating oils. The present inventors have discovered that the oxidation stability is significantly high, and have completed the present invention. That is, the present invention provides a synthetic lubricating oil containing 2-t-amylnaphthalene as a main component. Hereinafter, the content of the present invention will be explained in more detail. The synthetic lubricating oil of the present invention has 2-t-amylnaphthalene represented by the following structural formula as a main component. The synthesis method for this compound is arbitrary, but for example, naphthalene and t-amyl chloride may be reacted in the presence of a Friedel-Crafts type catalyst, or naphthalene and 2-methyl-1-butene or 2-methyl-2- It is obtained by reacting with butene in the presence of an alkylating agent. The reaction temperature is usually 20~
The temperature is 250℃. Examples of Friedel-Crafts type catalysts include aluminum chloride, zinc chloride, and iron chloride. As an alkylating agent,
For example, the Friedel-Crafts type catalyst mentioned above, sulfuric acid,
Examples include acidic catalysts such as phosphoric acid, phosphorus pentoxide, hydrofluoric acid, acid clay, and activated clay. Generally, the naphthalene derivatives of the present invention are synthesized by combining naphthalene with 2-methyl-1-butene or 2-methyl-2-butene, since the raw materials are easily available.
Olefins such as butenes, especially 2-methyl-2-
The most preferred method is to react with butene. The synthetic lubricating oil containing the naphthalene derivative of the present invention as a main component has excellent properties such as particularly good oxidation stability as well as various properties required of ordinary lubricating oils, but the synthetic lubricating oil of the present invention has If necessary, commonly used lubricating oil additives 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. Details of these various additives are described in, for example, "Journal of the Japan Society of Lubricating Oil, Volume 15, No. 6" or "Petroleum Product Additives" edited by Toshio Sakurai (Saiwai Shobo). The synthetic lubricating oil of the present invention can be mixed with mineral oil or known synthetic lubricating oil as necessary, as long as its high oxidation stability is not impaired. 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.The contents of the present invention will be described below with synthetic examples. A more specific explanation will be provided by Examples and Comparative Examples. Synthesis Example Activated clay 100 in which 1000 parts by weight of naphthalene was weighed in a four-necked flask, heated to 150°C while stirring in a nitrogen atmosphere, and further calcined at 220°C. 300 parts by weight of 2-methyl-2-butene was added dropwise little by little over 4 hours, and stirring was continued for 1 hour while maintaining the temperature at 200°C to form naphthalene and 2-butene. Methyl-2-butene was 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 the desired 2-t-amylnaphthalene. 2-methyl- The yield based on 2-butene was 76%.The properties of the obtained 2-t-amylnaphthalene are shown below: Viscosity: 5.2 cSt, 40°C, : 1.5 cSt, 100°C, Flow. Point: <-45℃, Boiling point: 128℃, 2.0mmHg, Example 1 and Comparative Examples 1 to 5 2-t-Amylnaphthalene (Example 1) obtained by the above synthesis example and for comparison, average molecular weight of 500 decene-1 oligomer (Comparative Example 1), dioctyl sebacate (Comparative Example 2), pentaerythritol tetracapriate (Comparative Example 3), diisopropylnaphthalene (Comparative Example 4), polyt-amylnaphthalene (Comparative Example 5) In order to evaluate the oxidation stability of the material, a high temperature oxidation test was conducted using the test equipment specified in IP-280 under the following conditions: Test temperature: 170℃, Oxygen flow rate: 3/hr, Catalyst: Copper wire 1 mmφ x 80 cm. The oxidation stability evaluation is based on the acid value of the sample oil.
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、本発明の合成潤滑油である２−ｔ−アミルナ
フタレン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２−ｔ−アミルナフタレン
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 of the present invention, 2-t-amylnaphthalene, exhibits extremely high high temperature oxidation stability. On the other hand, compounds such as polyα-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 2-t-amylnaphthalene as a main component of the present invention has high oxidation stability that cannot be achieved with other conventionally known synthetic lubricating oils.
Claims (1)
成潤滑油。1 Synthetic lubricating oil whose main component is 2-t-amylnaphthalene.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13788784A JPS6119696A (en) | 1984-07-05 | 1984-07-05 | Synthetic lubricating 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 |
|---|---|---|---|
| JP13788784A JPS6119696A (en) | 1984-07-05 | 1984-07-05 | Synthetic lubricating oil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6119696A JPS6119696A (en) | 1986-01-28 |
| JPH0425994B2 true JPH0425994B2 (en) | 1992-05-06 |
Family
ID=15208997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13788784A Granted JPS6119696A (en) | 1984-07-05 | 1984-07-05 | Synthetic lubricating oil |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6119696A (en) |
-
1984
- 1984-07-05 JP JP13788784A patent/JPS6119696A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6119696A (en) | 1986-01-28 |
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