WO2002088205A2 - Procede de preparation de polyalphaolefine a partir de 1-octene - Google Patents

Procede de preparation de polyalphaolefine a partir de 1-octene Download PDF

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Publication number
WO2002088205A2
WO2002088205A2 PCT/KR2001/000702 KR0100702W WO02088205A2 WO 2002088205 A2 WO2002088205 A2 WO 2002088205A2 KR 0100702 W KR0100702 W KR 0100702W WO 02088205 A2 WO02088205 A2 WO 02088205A2
Authority
WO
WIPO (PCT)
Prior art keywords
decene
polyalphaolefin
octene
viscosity
dodecene
Prior art date
Application number
PCT/KR2001/000702
Other languages
English (en)
Other versions
WO2002088205A3 (fr
Inventor
Ahn-Ki Lee
Byung-Ryul Choi
Sung-Hyeon Baeck
Byung-Il Kim
Original Assignee
Honam Petrochemical Corporation
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Honam Petrochemical Corporation filed Critical Honam Petrochemical Corporation
Priority to CN01823151.9A priority Critical patent/CN1215097C/zh
Priority to PCT/KR2001/000702 priority patent/WO2002088205A2/fr
Publication of WO2002088205A2 publication Critical patent/WO2002088205A2/fr
Publication of WO2002088205A3 publication Critical patent/WO2002088205A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
    • C08F255/08—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having four or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F210/14—Monomers containing five or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
    • C08F297/06—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the coordination type
    • C08F297/08—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the coordination type polymerising mono-olefins

Definitions

  • the present invention generally relates to a method for preparing polyalphaolefin from 1-octene, and more particularly, to a method for preparing high-viscosity polyalphaolefin chiefly used as an industrial oil with high yield under conditions of high temperature and high pressure from 1-octene using a catalyst obtained by prepolymerization of 1 -decene in the presence of ethyl aluminum dichloride (EADC) and t-butyl chloride (TBC).
  • EMC ethyl aluminum dichloride
  • TBC t-butyl chloride
  • polyalphaolefins have excellent fluidity in the wide range of temperature due to their high viscosity index and low-temperature fluidity, as well as narrow molecular weight distribution resulting in a low loss on heating, and high stability for long-term use, and are useful as a base stock for automotive or industrial oils.
  • U.S. Patent No. 4,532,061 describes a method for preparing high-viscosity polyalphaolefins that comprises providing (a) an aluminum compound having the formula R 3 AI 2 X 3 or R n AlX 3-n , wherein R is C ⁇ -C
  • U.S. Patent 4,469.910 also discloses a method for preparing high- viscosity polyalphaolefins that comprises diluting an alkyl aluminum and an alkylhalide catalyst having at least one halogen group with an alphaolefm having at least three carbon atoms, and bringing into contact the diluted alkyl aluminum and alkylhalide catalyst by mixing at a temperature of 42 ⁇ 2 °C.
  • U.S. Patent 4,594,469 describes a method for preparing high-viscosity polyalphaolefins having a kinetic viscosity of at least 300 cSt at 40 °C that comprises bringing an alphaolefm having at least three carbon atoms into contact with a catalyst composition composed of an alkyl aluminum bromide or iodine compound and a cocatalyst (selected from the group consisting of iodoalkyl and bromoalkyl).
  • polyalphaolefins obtained from 1-decene typically have a viscosity index of about 140, but those from 1 -octene have a lower viscosity index in the range from 125 to 130. Disclosure of Invention
  • preparation of polyalphaolefins having a kinetic viscosity of at least 90 cSt at 40 °C and a viscosity index of at least 135 involves prepolymerizing a small amount of 1-decene using a catalyst system composed of ethyl aluminum dichloride (EADC) and /-butyl chloride (TBC) and bringing the prepolymerization product into contact with 1-octene, less expensive and more available than 1 -decene, under conditions of high temperature and high pressure.
  • EADC ethyl aluminum dichloride
  • TBC /-butyl chloride
  • a method for preparing a polyalphaolefin including: prepolymerizing a small amount of 1-decene or 1-dodecene using a catalyst composed of ethyl aluminum dichloride (EADC) and t-butyl chloride
  • TBC THC
  • Normal polyalphaolefins are useful as automobile lubricants or industrial oils, but those prepared according to the present invention method have a high viscosity (for example, kinetic viscosity of at least 90 cSt at 40 °C and viscosity index of at least 135) and are very useful as industrial oils.
  • a catalyst system composed of EADC and TBC is used in the prepolymerization reaction of 1-decene or 1-dodecene.
  • the prepolymer thus obtained is used as a catalyst and brought into contact with 1-octene to produce a high-viscosity polyalphaolefin according to the present invention.
  • the mole ratio of 1 -octene to 1 -decene or 1 -dodecene is in the range from 10 to 50. If the mole ratio is less than 10, the method is inefficient in the economical aspect due to the excess of 1 -decene or 1 -dodecene. Otherwise, if the mole ratio is greater than 50, the added amount of 1-decene or 1-dodecene is too small to provide increased viscosity index.
  • reaction conditions i.e., temperature and pressure during the reaction of the prepolymer and 1-octene are desirably defined as room temperature (i.e., in the range of 20 to 40 °C) and atmospheric pressure (i.e., about 760 mmHg).
  • reaction temperature is lower than 20 °C, energy consumption is required to cool the stock material. Otherwise, if the reaction temperature is higher than 40 °C, the stock material has to be heated.
  • Example 1 300 ml of 1 -octane was added to a IL reactor, which is equipped with a stirrer, a cooling coil and a thermometer and kept under the nitrogen atmosphere at 30 °C.
  • 1-decene was separately added to 5.4 ml of 3.4M ethyl aluminum dichloride (EADC) and 2.1 ml of 8.99M /-butyl chloride (TBC) to have the total volume of 21 ml and a mole ratio of EADC to TBC being 1 :1.
  • EADC 3.4M ethyl aluminum dichloride
  • TBC 8.99M /-butyl chloride
  • EADC and TBC diluted with 1 -decene was injected into the flask using a microinjector with stirring for 5 minutes, and stirred for more 5 minutes to obtain a prepolymer. The prepolymer was then immediately added to the injector.
  • the prepolymer was added to the IL reactor containing 1-octene using a microinjector for 20 minutes.
  • the catalyst residue was removed with 200 ml of 0.1M NaOH.
  • the product removed of the residue was vacuum distilled at 180 °C under 1 torr to remove products having a low boiling point and monomers unturned, followed by filtering out the distillation residue to obtain the final product (77.3 wt% yield).
  • the polyalphaolefin thus obtained was then measured in regard to kinetic viscosity and viscosity index according to the regulations of the KSM 2014. The measurement results are presented in Table 1.
  • Example 1 The procedures as described in Example 1 were performed to cause the prepolymerization reaction and prepare a reactor. The subsequent procedures were performed in the same manner as described in Example 1 , excepting that the prepolymer obtained was added to the IL reactor with a microinjector for 10 minutes in order to obtain a polyalphaolefin having a lower kinetic viscosity (76.8 wt.% yield) through removal of catalyst residue, distillation and filtration.
  • Example 3 The polyalphaolefin thus obtained was also measured in regard to kinetic viscosity and viscosity index as described in Example 1. The measurement results are presented in Table 1.
  • Example 3 The polyalphaolefin thus obtained was also measured in regard to kinetic viscosity and viscosity index as described in Example 1. The measurement results are presented in Table 1.
  • Example 1 In addition, 1-decene was separately added to 5.4 ml of 3.4M EADC and 2.1 ml of 8.99M TBC to have the total volume of 12.4 ml and a mole ratio of EADC to TBC being 1 :1. The mixture was then charged in an injector. Here, the mole ratio of 1 -octene to 1 -decene was 20: 1.
  • the polyalphaolefin thus obtained was also measured in regard to kinetic viscosity and viscosity index as described in Example 1. The measurement results are presented in Table 1.
  • Example 4 The procedures were performed in the same manner as described in Example 1, excepting that the catalyst and 1 -decene added to an injector were injected into the IL reactor for 5 minutes and, after 5 minutes, 300 ml of 1-octene was injected to the prepolymer using a microinjector with stirring for 20 minutes to obtain a polyalphaolefin (75.4 wt.% yield) through removal of catalyst residue, distillation and filtration. The polyalphaolefin thus obtained was also measured in regard to kinetic viscosity and viscosity index as described in Example 1. The measurement results are presented in Table 1.
  • TBC to have the total volume of 20 ml and a mole ratio of EADC to TBC being 1 : 1.
  • the mixture was then charged in an injector.
  • the mole ratio of 1 -octene to 1 -decene was
  • the mixture of EADC and TBC diluted with 1-decene was injected into the flask using a microinjector with stirring for 5 minutes, and stirred for more 5 minutes to obtain a prepolymer.
  • the prepolymer was then immediately added to the injector.
  • the subsequent procedures were performed in the same manner as described in Example 1 to obtain a polyalphaolefin (79.7 wt.% yield).
  • the polyalphaolefin thus obtained was also measured in regard to kinetic viscosity and viscosity index as described in Example 1. The measurement results are presented in Table 1.
  • Example 6 In the same manner as described in Example 1 , 1 -octane was added to a IL reactor and 1 -decene was separately added to 5.4 ml of 3.4M EADC and 2.1 ml of 8.99M TBC to have the total volume of 12.2 ml and a mole ratio of EADC to TBC being 1 : 1. The mixture was then charged in an injector. Here, the mole ratio of 1-octene to 1-decene was 20: 1. The subsequent procedures were performed in the same manner as described in
  • Example 5 to obtain a polyalphaolefin (82.1 wt.% yield).
  • 1-octene was separately added to 5.4 ml of 3.4M EADC and 2.1 ml of 8.99M TBC to have the total volume of 21 ml and a mole ratio of EADC to TBC being 1 : 1. The mixture was then charged in an injector.
  • the mixture of EADC and TBC diluted with 1 -octene was injected into the IL reactor using a microinjector with stirring for 20 minutes. After the completion of injection and 30 minutes of stirring, the catalyst residue was removed with 200 ml of
  • the polyalphaolefin thus obtained was also measured in regard to kinetic viscosity and viscosity index as described in Example 1. The measurement results are presented in Table 1.
  • Comparative Example 1 to prepare the catalyst, inject it into the reactor for 20 minutes and obtain a polyalphaolefin (81.1 wt.% yield) through removal of catalyst residue, distillation and filtration.
  • the polyalphaolefin thus obtained was also measured in regard to kinetic viscosity and viscosity index as described in Example 1. The measurement results are presented in Table 1.
  • the polyalphaolefin thus obtained was also measured in regard to kinetic viscosity and viscosity index as described in Example 1. The measurement results are presented in Table 1.
  • the present invention involves prepolymerizing a small amount of 1-decene or 1 -dodecene using a catalyst system composed of EADC and TBC and bringing the prepolymerization product into contact with 1-octene.
  • the use of 1 -octene less expensive than 1-decene as a main stock material and a small amount of 1-decene or 1 -dodecene makes it possible to produce a polyalphaolefin with high yield at room temperature and under atmospheric pressure, wherein the polyalphaolefin thus obtained has a high kinetic viscosity index almost equal to that of the polyalphaolefin obtained from 1-decene as a monomer and much higher than that of the polyalphaolefin from 1-octene.
  • the present invention also allows it to easily control the kinetic viscosity of the polyalphaolefin by regulating the polymerization reaction or the mole ratio of 1 -octene to 1-decene or 1-dodecene.
  • the polyalphaolefins of the invention have excellent fluidity in the wide range of temperature due to their high viscosity index and low-temperature fluidity, as well as narrow molecular weight distribution resulting in a low loss on heating, and high stability for long-term use, and are useful as a base stock for automotive or industrial oils.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

Abstract

La présente invention concerne un procédé de préparation d'une polyalphaoléfine à viscosité élevée, principalement utile en tant qu'huile industrielle, à rendement élevé dans des conditions de température du laboratoire et de pression atmosphérique, ledit procédé consistant à: prépolymériser du 1-decène ou du 1-dodecène au moyen d'un catalyseur composé de dichlorure en aluminium éthylique (EADC) et de chlorure t-butylique (TBC) pour obtenir un prépolymère, et à mettre du 1-octène en contact avec le prépolymère utilisé en tant que catalyseur dans des conditions de température du laboratoire et de pression atmosphérique. L'utilisation dudit procédé permet la préparation d'une polyalphaoléfine à viscosité élevée à partir de 1-octène plus économique que du 1-decène ou du 1-dodecène, la polyalphaoléfine possédant une viscosité cinétique d'au moins 90 centistokes (cSt) à 40 °C et un indice de viscosité d'au moins 135 permettant de résoudre le problème présenté par une polyalphaoléfine à faible viscosité obtenue à partir de 1-decène ou de 1-dodecène.
PCT/KR2001/000702 2001-04-27 2001-04-27 Procede de preparation de polyalphaolefine a partir de 1-octene WO2002088205A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN01823151.9A CN1215097C (zh) 2001-04-27 2001-04-27 从1－辛烯制备聚α烯烃的方法
PCT/KR2001/000702 WO2002088205A2 (fr) 2001-04-27 2001-04-27 Procede de preparation de polyalphaolefine a partir de 1-octene

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Application Number Priority Date Filing Date Title
PCT/KR2001/000702 WO2002088205A2 (fr) 2001-04-27 2001-04-27 Procede de preparation de polyalphaolefine a partir de 1-octene

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WO2002088205A3 WO2002088205A3 (fr) 2002-12-27

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006078395A1 (fr) * 2005-01-14 2006-07-27 Exxonmobil Chemical Patents Inc. Polyalphaolefines haute viscosite basees sur 1-decene / 1-dodecene
US20140039137A1 (en) * 2012-08-03 2014-02-06 Ramot At Tel-Aviv University Ltd. Polyalphaolefins Prepared Using Modified Salan Catalyst Compounds
US20150158958A1 (en) * 2012-08-03 2015-06-11 Exxonmobil Chemical Patents Inc. Polyalphaolefins Prepared Using Modified Salan Catalyst Compounds
RU2666725C1 (ru) * 2018-06-22 2018-09-12 Публичное Акционерное Общество "Нижнекамскнефтехим" Способ получения полиальфаолефинов с кинематической вязкостью 10-25 сСт
US11198745B2 (en) * 2018-11-29 2021-12-14 Exxonmobil Chemical Patents Inc. Poly(alpha-olefin)s and methods thereof

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3896141B1 (fr) * 2020-04-14 2023-08-30 Indian Oil Corporation Limited Procédé de contrôle de la viscosité cinématique d'une polyalphaoléfine

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4006199A (en) * 1975-04-22 1977-02-01 Lion Fat & Oil Co., Ltd. Method for preparation of liquid polyolefin oil
US4045508A (en) * 1975-11-20 1977-08-30 Gulf Research & Development Company Method of making alpha-olefin oligomers
US4045507A (en) * 1975-11-20 1977-08-30 Gulf Research & Development Company Method of oligomerizing 1-olefins
GB1535325A (en) * 1975-11-27 1978-12-13 Uniroyal Inc Oligomerization of alpha-olefins
US4239927A (en) * 1979-04-05 1980-12-16 Mobil Oil Corporation Removal of organic chlorides from synthetic oils
EP0561360A1 (fr) * 1992-03-16 1993-09-22 Phillips Petroleum Company Procédé de polymérisation pour la préparation de polyoléfine à partir d'alpha-oléfines stériquement empêchées à ramifications méthyl
DE4415912A1 (de) * 1994-05-05 1995-11-09 Linde Ag Verfahren zur Oligomerisierung von alpha-Olefinen zu Poly-alpha-Olefinen

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4006199A (en) * 1975-04-22 1977-02-01 Lion Fat & Oil Co., Ltd. Method for preparation of liquid polyolefin oil
US4045508A (en) * 1975-11-20 1977-08-30 Gulf Research & Development Company Method of making alpha-olefin oligomers
US4045507A (en) * 1975-11-20 1977-08-30 Gulf Research & Development Company Method of oligomerizing 1-olefins
GB1535325A (en) * 1975-11-27 1978-12-13 Uniroyal Inc Oligomerization of alpha-olefins
US4239927A (en) * 1979-04-05 1980-12-16 Mobil Oil Corporation Removal of organic chlorides from synthetic oils
EP0561360A1 (fr) * 1992-03-16 1993-09-22 Phillips Petroleum Company Procédé de polymérisation pour la préparation de polyoléfine à partir d'alpha-oléfines stériquement empêchées à ramifications méthyl
DE4415912A1 (de) * 1994-05-05 1995-11-09 Linde Ag Verfahren zur Oligomerisierung von alpha-Olefinen zu Poly-alpha-Olefinen

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006078395A1 (fr) * 2005-01-14 2006-07-27 Exxonmobil Chemical Patents Inc. Polyalphaolefines haute viscosite basees sur 1-decene / 1-dodecene
US7550640B2 (en) 2005-01-14 2009-06-23 Exxonmobil Chemical Patents Inc. High viscosity PAOs based on 1-decene/1-dodecene
US20140039137A1 (en) * 2012-08-03 2014-02-06 Ramot At Tel-Aviv University Ltd. Polyalphaolefins Prepared Using Modified Salan Catalyst Compounds
US20150158958A1 (en) * 2012-08-03 2015-06-11 Exxonmobil Chemical Patents Inc. Polyalphaolefins Prepared Using Modified Salan Catalyst Compounds
US9365661B2 (en) * 2012-08-03 2016-06-14 Exxonmobil Chemical Patents Inc. Polyalphaolefins prepared using modified salan catalyst compounds
US9382349B2 (en) * 2012-08-03 2016-07-05 Exxonmobil Chemical Patents Inc. Polyalphaolefins prepared using modified Salan catalyst compounds
RU2666725C1 (ru) * 2018-06-22 2018-09-12 Публичное Акционерное Общество "Нижнекамскнефтехим" Способ получения полиальфаолефинов с кинематической вязкостью 10-25 сСт
US11198745B2 (en) * 2018-11-29 2021-12-14 Exxonmobil Chemical Patents Inc. Poly(alpha-olefin)s and methods thereof

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WO2002088205A3 (fr) 2002-12-27
CN1215097C (zh) 2005-08-17
CN1505643A (zh) 2004-06-16

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