JP3348893B2 - Method for producing olefin oligomer - Google Patents
Method for producing olefin oligomerInfo
- Publication number
- JP3348893B2 JP3348893B2 JP71493A JP71493A JP3348893B2 JP 3348893 B2 JP3348893 B2 JP 3348893B2 JP 71493 A JP71493 A JP 71493A JP 71493 A JP71493 A JP 71493A JP 3348893 B2 JP3348893 B2 JP 3348893B2
- Authority
- JP
- Japan
- Prior art keywords
- olefin
- decene
- oligomer
- octene
- dodecene
- 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
- 150000001336 alkenes Chemical class 0.000 title claims description 45
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 42
- 238000004519 manufacturing process Methods 0.000 title description 11
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 37
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 26
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims description 23
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 23
- 229910015900 BF3 Inorganic materials 0.000 claims description 13
- 229940069096 dodecene Drugs 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 description 11
- 239000002994 raw material Substances 0.000 description 10
- 239000004711 α-olefin Substances 0.000 description 7
- 239000002199 base oil Substances 0.000 description 5
- 239000010687 lubricating oil Substances 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003426 co-catalyst Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 Alicyclic hydrocarbons Chemical class 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/14—Catalytic processes with inorganic acids; with salts or anhydrides of acids
- C07C2/20—Acids of halogen; Salts thereof ; Complexes thereof with organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明はオレフィンオリゴマーの
製造方法に関し、自動車や冷凍機などに使用する潤滑油
の基油として用いられ、航空機の油圧作動液やグリース
などの原料油、電気絶縁油などの原料油にも用いられ、
特に自動車エンジンの潤滑油の基油として用いられるオ
レフィンオリゴマーの製造方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing an olefin oligomer, which is used as a base oil for lubricating oils used in automobiles and refrigerators, and is used as a base oil for hydraulic fluids and greases for aircraft, electric insulating oil, etc. It is also used for base oils,
In particular, the present invention relates to a method for producing an olefin oligomer used as a base oil of a lubricating oil for an automobile engine.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】粘度指
数および流動点は潤滑油の性能を示す重要な規格であ
る。比較的短鎖のα−オレフィンから得られたオレフィ
ンオリゴマーは粘度指数が低く、一方比較的長鎖のα−
オレフィンから得られたオリゴマーは流動点が高いとい
う欠点を有しているため、粘度指数、流動点共に優れた
潤滑油を製造するためには１−デセンを原料として使用
する必要があった。ところで、１−デセンはα−オレフ
ィン製造装置により製造されるα−オレフィンの一留分
にすぎず、他の多くの留分が同時生産されるため、１−
デセンの生産量には限界がある。そこで、必要に応じて
他の留分を原料として併用できる柔軟性のあるオレフィ
ンオリゴマーの製造方法が求められていた。しかし、１
−デセンへ短鎖のα−オレフィンを加えると、得られる
オリゴマーの粘度指数が低下してしまい、長鎖のα−オ
レフィンを加えると、得られるオリゴマーの流動点が上
昇してしまうため、併用できる他のα−オレフィンは少
量であり、原料選択に柔軟性のあるオレフィンオリゴマ
ーの製造方法ではなかった。BACKGROUND OF THE INVENTION Viscosity index and pour point are important specifications for the performance of lubricating oils. Olefin oligomers obtained from relatively short-chain α-olefins have a low viscosity index, while relatively long-chain α-olefins.
Oligomers obtained from olefins have the drawback of having a high pour point, so that it was necessary to use 1-decene as a raw material in order to produce a lubricating oil having excellent viscosity index and pour point. By the way, 1-decene is only a fraction of an α-olefin produced by an α-olefin production apparatus, and many other fractions are produced simultaneously.
Decene production is limited. Therefore, there has been a demand for a method for producing a flexible olefin oligomer which can be used in combination with another fraction as a raw material if necessary. However, 1
Addition of a short-chain α-olefin to decene lowers the viscosity index of the obtained oligomer, and addition of a long-chain α-olefin increases the pour point of the obtained oligomer, so that it can be used in combination. Other α-olefins were in small amounts, and were not a method for producing olefin oligomers with flexibility in raw material selection.
【０００３】従って本発明の目的は、原料選択に柔軟性
があり、かつ得られたオレフィンオリゴマーが１−デセ
ンから得られた従来のオレフィンオリゴマーと同等の性
能を有するオレフィンオリゴマーの製造方法を提供する
ことにある。[0003] Accordingly, an object of the present invention is to provide a method for producing an olefin oligomer which is flexible in the selection of raw materials and in which the obtained olefin oligomer has the same performance as a conventional olefin oligomer obtained from 1-decene. It is in.
【０００４】[0004]
【課題を解決するための手段】本発明者は、上記目的を
達成するために鋭意検討を加えた結果、１−デセンとと
もに１−デセンよりも短鎖のオレフィンである１−オク
テンと長鎖のオレフィンである１−ドデセンからなり、
１−オクテン／１−ドデセンのモル比率が１／２〜２／
１であるオレフィン混合物を、三フッ化ホウ素および三
フッ化ホウ素と助触媒との錯体とを含む触媒の存在下に
重合させることにより、１−デセンを重合させることに
より得られたオレフィンオリゴマーと同等の性能を有す
るオレフィンオリゴマーが得られることを見い出し、本
発明を完成した。Means for Solving the Problems As a result of intensive studies to achieve the above object, the present inventor has found that 1- octene which is a shorter chain olefin than 1 - decene together with 1- decene.
Consisting of ten and 1-dodecene, a long-chain olefin ,
The molar ratio of 1-octene / 1-dodecene is 1/2 to 2 /
1 is polymerized in the presence of a catalyst containing boron trifluoride and a complex of boron trifluoride and a co-catalyst to obtain an olefin mixture equivalent to an olefin oligomer obtained by polymerizing 1- decene. It has been found that an olefin oligomer having the following properties can be obtained, and the present invention has been completed.
【０００５】すなわち本発明は、１−デセン、１−オク
テンおよび１−ドデセンかならなり、１−オクテン／１
−ドデセンのモル比率が１／２〜２／１であるオレフィ
ン混合物を、三フッ化ホウ素および三フッ化ホウ素と助
触媒との錯体とを含む触媒の存在下に重合させることを
特徴とするオレフィンオリゴマーの製造方法を要旨とす
る。That is, the present invention relates to 1-decene, 1-octane
Ten and 1-dodecene, 1-octene / 1
Polymerizing an olefin mixture in which the molar ratio of dodecene is 1/2 to 2/1 in the presence of boron trifluoride and a catalyst comprising a complex of boron trifluoride and a co-catalyst; The gist of the present invention is a method for producing an olefin oligomer.
【０００６】以下、本発明を詳説する。従来、潤滑油の
基油として用いられるオレフィンオリゴマーは、原料と
して１−デセンを用いて得られていたが、本発明におい
ては、原料として、炭素数１０のオレフィン（１−デセ
ン）と、該オレフィンよりも短鎖のオレフィンである１
−オクテンおよび長鎖のオレフィンである１−ドデセン
とからなるオレフィン混合物が用いられる。上述のよう
に従来法では、原料として生産量に限界があり、高価な
１−デセン単品を用いており、これがオレフィンオリゴ
マー製品のコスト高の原因となっていたが、本発明にお
いては、上記のような炭素数８〜１２のオレフィン混合
物を用いるため、上記従来法のような欠点がなく、原料
選択に柔軟性があり、オレフィンオリゴマー製品のコス
ト低減に資する点で、その工業的かつ商業的価値は極め
て多大である。Hereinafter, the present invention will be described in detail. Conventionally, an olefin oligomer used as a base oil for a lubricating oil has been obtained using 1-decene as a raw material. However, in the present invention, an olefin having 10 carbon atoms ( 1- decene) and the olefin are used as a raw material. 1 which is a shorter chain olefin than
-Octene and 1-dodecene which is a long-chain olefin
An olefin mixture consisting of As described above, in the conventional method, the production amount is limited as a raw material, and expensive 1-decene is used alone, which has caused the cost of the olefin oligomer product to be high. Since such an olefin mixture having 8 to 12 carbon atoms is used, it does not have the drawbacks of the above-described conventional method, has flexibility in selecting raw materials, and contributes to cost reduction of olefin oligomer products, and thus has an industrial and commercial value. Is extremely large.
【０００７】本発明において原料として用いられるオレ
フィン混合物は、１−デセンを４０mole％以上含有し、
残りが１−オクテンおよび１−ドデセンであるのが好ま
しい。１−オクテン／１−ドデセンのモル比率は１／２
〜２／１に限定されるが、１／１またはその近傍である
のが特に好ましい。[0007] Luo les <br/> fins mixture used as a starting material in the present invention contain 1-decene or 40Mole%,
Preferably the balance is 1-octene and 1-dodecene. The molar ratio of 1-octene / 1-dodecene is 1/2
Although it is limited to ~ 2/1, it is particularly preferable that it is 1/1 or its vicinity.
【０００８】上記オレフィン混合物の重合において用い
られる触媒は、三フッ化ホウ素および三フッ化ホウ素と
助触媒との錯体を含む。ここに上記助触媒とは、三フッ
化ホウ素と錯化し重合活性のある錯体を形成する任意の
化合物およびその混合物であり、例えば水、アルコール
類（メタノール、エタノール、ｎ−ブタノール、デカノ
ール等）、カルボン酸類（酢酸、プロピオン酸、酪酸
等）、エーテル類（ジメチルエーテル、ジエチルエーテ
ル等）、酸無水物類（無水酢酸等）、エステル類（酢酸
エチル、プロピオン酸メチル等）、ケトン類（アセト
ン、メチルエチルケトン等）、アルデヒド類（アセトア
ルデヒド、ベンズアルデヒド等）等が挙げられる。[0008] The catalyst used in the polymerization of the olefin mixture includes boron trifluoride and a complex of boron trifluoride and a cocatalyst. Here, the cocatalyst is an arbitrary compound that forms a complex having polymerization activity with boron trifluoride and a mixture thereof, such as water, alcohols (methanol, ethanol, n-butanol, decanol, etc.), Carboxylic acids (acetic acid, propionic acid, butyric acid, etc.), ethers (dimethyl ether, diethyl ether, etc.), acid anhydrides (acetic acid anhydride, etc.), esters (ethyl acetate, methyl propionate, etc.), ketones (acetone, methyl ethyl ketone) Aldehydes (acetaldehyde, benzaldehyde, etc.).
【０００９】オレフィン混合物の重合反応において、三
フッ化ホウ素濃度は特に制限がないが、オレフィンに対
して通常０．０２〜０．２ｗｔ％である。また三フッ化
ホウ素と助触媒との錯体の濃度も特に制限がないが、オ
レフィンに対して通常０．０５〜１０ｗｔ％、好ましく
は０．１〜５ｗｔ％である。In the polymerization reaction of the olefin mixture, the concentration of boron trifluoride is not particularly limited, but is usually 0.02 to 0.2% by weight based on the olefin. The concentration of the complex of boron trifluoride and the cocatalyst is not particularly limited, but is usually 0.05 to 10% by weight, preferably 0.1 to 5% by weight based on the olefin.
【００１０】オレフィン混合物の重合反応において溶媒
は特に使用する必要がないが、所望によりハロゲン化炭
化水素類（四塩化炭素、クロロホルム、塩化メチレン
等）、鎖状飽和炭化水素類（ペンタン、ヘプタン等）、
脂環式炭化水素類（シクロヘキサン、メチルシクロヘキ
サン、デカリン等）を用いても良い。In the polymerization reaction of the olefin mixture, there is no particular need to use a solvent, but if desired, halogenated hydrocarbons (carbon tetrachloride, chloroform, methylene chloride, etc.) and chain saturated hydrocarbons (pentane, heptane, etc.) ,
Alicyclic hydrocarbons (cyclohexane, methylcyclohexane, decalin, etc.) may be used.
【００１１】その他の重合条件は特に制限がなく、通常
のオレフィンのオリゴマー化に採用される条件がそのま
ま採用される。例えば重合温度は通常−２０〜９０℃、
好ましくは−１０〜６０℃である。The other polymerization conditions are not particularly limited, and the conditions employed for ordinary oligomerization of olefins are employed as they are. For example, the polymerization temperature is usually -20 to 90 ° C,
Preferably it is -10 to 60C.
【００１２】このようにして生成したオレフィンオリゴ
マーは通常、未反応オレフィンおよび炭素数３０未満の
低分子量オリゴマーを留去した後、熱的安定性を向上さ
せる目的で水素添加処理が行なわれる。The olefin oligomer thus produced is usually subjected to a hydrogenation treatment for the purpose of improving thermal stability after distilling off unreacted olefin and low molecular weight oligomer having less than 30 carbon atoms.
【００１３】[0013]
【実施例】以下実施例により本発明を更に説明するが、
本発明はこれらの実施例に限定されるものではない。The present invention will be further described with reference to the following examples.
The present invention is not limited to these examples.
【００１４】実施例１ 撹拌機、温度計、ガス導入管およびガス排気管を備えた
重合用フラスコを乾燥窒素ガスにて置換後、１−デセン
６０ｍｌ（５９mole％）、１−オクテン２０ｍｌ（２４
mole％）および１−ドデセン２０ｍｌ（１７mole％）を
入れ、２０℃まで冷却した。三フッ化ホウ素を吹き込み
飽和させた後、三フッ化ホウ素・ブタノール錯体をオレ
フィン１００ｍｌ当たり１．１ｍｌ添加して撹拌を始
め、重合を開始した。２０℃に保つように冷却しながら
２時間重合した。重合終了後５％アンモニア水１００ｍ
ｌを加えて触媒を失活させた後、水洗、乾燥し、未反応
オレフィンおよび炭素数３０未満の低分子量オリゴマー
を留去して目的とするオレフィンオリゴマーを得た。こ
のときのオレフィン転化率、オリゴマー収率およびオリ
ゴマー性状を表１に示す。 Example 1 A polymerization flask equipped with a stirrer, a thermometer, a gas inlet pipe and a gas exhaust pipe was replaced with dry nitrogen gas, and then 60 ml of 1-decene (59 mole%) and 20 ml of 1-octene (24 ml).
mole%) and 20 ml (17 mole%) of 1-dodecene, and cooled to 20 ° C. After blowing and saturating with boron trifluoride, 1.1 ml of boron trifluoride / butanol complex was added per 100 ml of olefin, stirring was started, and polymerization was started. The polymerization was carried out for 2 hours while cooling at 20 ° C. After polymerization, 100% of 5% ammonia water
After adding 1 to deactivate the catalyst, washing with water and drying were carried out, and unreacted olefins and low molecular weight oligomers having less than 30 carbon atoms were distilled off to obtain the desired olefin oligomers. The olefin conversion, oligomer yield and oligomer properties at this time are shown in Table 1.
【００１５】実施例２〜３，参考例，比較例１〜２ 原料オレフィン組成および重合条件を変化させた以外は
実施例１と同様の操作を行った。このときの原料オレフ
ィン組成、重合条件、オレフィン転化率、オリゴマー収
率およびオリゴマー性状を表１に示す。 Examples 2 to 3 , Reference Examples and Comparative Examples 1 to 2 The same operation as in Example 1 was carried out except that the composition of the starting olefin and the polymerization conditions were changed. Table 1 shows the raw material olefin composition, polymerization conditions, olefin conversion, oligomer yield and oligomer properties.
【００１６】[0016]
【表１】 [Table 1]
【００１７】また１−デセンと１−オクテンを用いた比
較例１および１−デセンと１−ドデセンを用いた比較例
２の結果と実施例１〜３の結果と対比すると、１−デセ
ンよりも短鎖の１−オクテンおよび長鎖の１−ドデセン
を併用することが好ましいことが判明した。Also, when the results of Comparative Example 1 using 1-decene and 1-octene and Comparative Example 2 using 1-decene and 1-dodecene are compared with the results of Examples 1 to 3, the results are higher than those of 1-decene. It has been found preferable to use a combination of short-chain 1-octene and long-chain 1-dodecene.
【００１８】[0018]
【発明の効果】以上のように本発明によれば、原料選択
に柔軟性があり、かつ得られたオレフィンオリゴマーが
１−デセンから得られた従来のオレフィンオリゴマーと
同等の性能を有するオレフィンオリゴマーの製造方法が
提供された。As described above, according to the present invention, the selection of raw materials is flexible, and the obtained olefin oligomer has a performance equivalent to that of a conventional olefin oligomer obtained from 1-decene. A manufacturing method has been provided.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ // Ｃ０７Ｂ 61/00 ３００ Ｃ０７Ｂ 61/00 ３００ Ｃ１０Ｎ 30:02 Ｃ１０Ｎ 30:02 40:08 40:08 40:16 40:16 40:25 40:25 40:30 40:30 50:10 50:10 70:00 70:00 (58)調査した分野(Int.Cl.7，ＤＢ名) C07C 2/26 C07C 2/32 C07C 11/02 C10M 105/04 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 7 Identification symbol FI // C07B 61/00 300 C07B 61/00 300 C10N 30:02 C10N 30:02 40:08 40:08 40:16 40:16 40:25 40:25 40:30 40:30 50:10 50:10 70:00 70:00 (58) Field surveyed (Int.Cl. 7 , DB name) C07C 2/26 C07C 2/32 C07C 11 / 02 C10M 105/04
Claims (2)
デセンかならなり、１−オクテン／１−ドデセンのモル
比率が１／２〜２／１であるオレフィン混合物を、三フ
ッ化ホウ素および三フッ化ホウ素と助触媒との錯体とを
含む触媒の存在下に重合させることを特徴とするオレフ
ィンオリゴマーの製造方法。1. 1-decene, 1-octene and 1-de
Decene, 1-octene / 1-dodecene mole
A process for producing an olefin oligomer, comprising polymerizing an olefin mixture having a ratio of 1/2 to 2/1 in the presence of boron trifluoride and a catalyst containing a complex of boron trifluoride and a cocatalyst. .
が１／１またはその近傍である、請求項１に記載の方
法。2. The molar ratio of 1-octene / 1-dodecene
The method of claim 1, wherein is at or near 1/1 .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP71493A JP3348893B2 (en) | 1993-01-06 | 1993-01-06 | Method for producing olefin oligomer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP71493A JP3348893B2 (en) | 1993-01-06 | 1993-01-06 | Method for producing olefin oligomer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06199708A JPH06199708A (en) | 1994-07-19 |
| JP3348893B2 true JP3348893B2 (en) | 2002-11-20 |
Family
ID=11481435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP71493A Expired - Lifetime JP3348893B2 (en) | 1993-01-06 | 1993-01-06 | Method for producing olefin oligomer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3348893B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8598394B2 (en) | 2008-06-30 | 2013-12-03 | Exxonmobil Chemical Patents Inc. | Manufacture of low viscosity poly alpha-olefins |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4891469B2 (en) * | 1998-07-01 | 2012-03-07 | 出光興産株式会社 | Traction drive fluid |
| US6824671B2 (en) * | 2001-05-17 | 2004-11-30 | Exxonmobil Chemical Patents Inc. | Low noack volatility poly α-olefins |
| US6869917B2 (en) * | 2002-08-16 | 2005-03-22 | Exxonmobil Chemical Patents Inc. | Functional fluid lubricant using low Noack volatility base stock fluids |
| US7550640B2 (en) * | 2005-01-14 | 2009-06-23 | Exxonmobil Chemical Patents Inc. | High viscosity PAOs based on 1-decene/1-dodecene |
| JP2008214643A (en) * | 2008-05-07 | 2008-09-18 | Idemitsu Kosan Co Ltd | Method for producing traction drive fluid base oil |
| CN103282331A (en) * | 2011-01-13 | 2013-09-04 | 出光兴产株式会社 | Process for producing olefin oligomer mixture |
| US20140256997A1 (en) * | 2011-05-19 | 2014-09-11 | Idemitsu Kosan Co., Ltd. | 1-octene, 1-decene, 1-dodecene ternary copolymer and lubricant composition containing same |
| JP7055646B2 (en) * | 2018-01-25 | 2022-04-18 | 住鉱潤滑剤株式会社 | Aerosol lubricant composition |
-
1993
- 1993-01-06 JP JP71493A patent/JP3348893B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8598394B2 (en) | 2008-06-30 | 2013-12-03 | Exxonmobil Chemical Patents Inc. | Manufacture of low viscosity poly alpha-olefins |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06199708A (en) | 1994-07-19 |
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