CN1505643A - Method for preparing polyalphaolefin from 1-octene - Google Patents
Method for preparing polyalphaolefin from 1-octene Download PDFInfo
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- CN1505643A CN1505643A CNA018231519A CN01823151A CN1505643A CN 1505643 A CN1505643 A CN 1505643A CN A018231519 A CNA018231519 A CN A018231519A CN 01823151 A CN01823151 A CN 01823151A CN 1505643 A CN1505643 A CN 1505643A
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- Prior art keywords
- polyalphaolefin
- decene
- octene
- viscosity
- prepolymer
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- 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
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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
Disclosed is a method for preparing a high-viscosity polyalphaolefin, chiefly useful as an industrial oil, with high yield under conditions of the room temperature and atmospheric pressure, the method including: prepolymerizing 1-decene or 1-dodecene using a catalyst composed of ethyl aluminum dichloride (EADC) and t-butyl chloride (TBC) to obtain a prepolymer, and bringing 1-octene into contact with the prepolymer used as a catalyst under conditions of the room temperature and atmospheric pressure. Using the method makes it possible to prepare a high-viscosity polyalphaolefin from 1-octene less expensive than 1-decene or 1-dodecene, the polyalphaolefin having a kinetic viscosity of at least 90 cSt at 40 DEG C and a viscosity index of at least 135 to overcome the problem with a low-viscosity polyalphaolefin from 1-decene or 1-dodecene.
Description
Technical field
The present invention relates to a kind of method for preparing polyalphaolefin from the 1-octene, more particularly, relate to a kind of use catalyzer that the 1-decene prepolymerization obtains in the presence of ethylaluminum dichloride (EADC) and tertiary butyl chloride (TBC) mainly is used as the high viscosity polyalphaolefin of industry oil from the preparation of 1-octene high productivity under high-temperature and high-pressure conditions method.
Background technology
Usually, the low narrow molecular weight distributions of loss and be beneficial to the high stability of life-time service when polyalphaolefin has excellent flowing because of its high viscosity index (HVI) and low-temperature fluidity and makes its heating in very wide temperature range, and be suitable as the basic raw material of automobile or industry oil.
Along with industrial expansion, carried out the research of many preparation polyalphaolefins.
Important reference is:
The U.S. 4,532, No. 061 patent has been described a kind of method for preparing full-bodied polyalphaolefin, comprising: it is R that general formula is provided
3Al
2X
3Or R
nAlX
3-nAluminum compound (a), wherein R is C
1-C
18Alkyl, C
7-C
9Aralkyl, C
7-C
9Alkaryl or C
6-C
10Aryl, X are Cl, Br or I, and n is that integer and the general formula of 1-3 is (CH
2CR
1R
2)
mY
pMany halons catalyzer, R wherein
1Be hydrogen or C
1-C
3Alkyl, R
2Be the C of straight or branched
1-C
30Alkyl, Y are Cl, Br or I, and m is the integer of 3-3000, and p is at least 3 integer; With the alhpa olefin of at least three carbon atoms dilution above-mentioned (a) and (b), (a) of mixed diluting makes it to contact with (b) under 0-60 ℃ of temperature.
The U.S. 4,469, No. 910 patent also discloses a kind of method for preparing the high viscosity polyalphaolefin, comprise with the alhpa olefin of at least three carbon atoms dilution aluminum alkyls and contain haloalkane catalyzer that at least one halogen rolls into a ball, the aluminum alkyls of mixed diluting contacts them with the haloalkane catalyzer under 42 ± 2 ℃ of temperature.
The U.S. 4,594, kinetic viscosity was at least the method for the high viscosity polyalphaolefin of 300cSt when No. 469 patents had been described 40 ℃ of a kind of preparations, comprised catalyzer and a kind of co-catalyst (being selected from the group that iodine alkyl and bromine alkyl are formed) that the alhpa olefin that makes at least three carbon atoms and a kind of alkyl bromide or aluminum iodide are formed.
Aforesaid method uses various catalyzer and a kind of alhpa olefin in the preparation of polyalphaolefin, particularly because of the expensive and difficult 1-decene that obtains of the increase of demand.In order to overcome this problem, many trials have been carried out from preparing polyalphaolefin than the cheap 1-hexene of 1-decene or 1-octene.But, compare with the polyalphaolefin for preparing from 1-decene from the polyalphaolefin of 1-hexene or the preparation of 1-octene, have the viscosity index of low measurement stability.
More specifically, the polyalphaolefin that obtains from 1-decene typically has about 140 viscosity index, but low from the viscosity index of the polyalphaolefin of 1-octene preparation, in the 125-130 scope.
Summary of the invention
Therefore, the contriver has studied the method for preparing polyalphaolefin from a spot of 1-decene, the polyalphaolefin of preparation has identical viscosity index with those polyalphaolefins of preparing from 1-decene, having kinetic viscosity based on preparation is at least the fact that 90cSt and viscosity index be at least 135 polyalphaolefin 40 ℃ the time and has designed the present invention, this preparation method comprises a spot of 1-decene of catalyst system prepolymerization that uses ethylaluminum dichloride (EADC) and tertiary butyl chloride (TBC) to form, and, prepolymerized product is contacted under High Temperature High Pressure with than the cheap 1-octene that is easy to get of 1-decene.
Therefore, an object of the present invention is to provide a kind of high viscosity polyalphaolefin preparation method, the viscosity index of this polyalphaolefin much larger than before the viscosity index of the polyalphaolefin for preparing from 1-decene from the viscosity index of the polyalphaolefin of 1-octene preparation and before equaling at least.
In order to reach purpose of the present invention, a kind of method for preparing polyalphaolefin is provided, this method comprises: use a spot of 1-decene of catalyzer prepolymerization or the 1-dodecylene be made up of ethylaluminum dichloride (EADC) and tertiary butyl chloride to obtain prepolymer, make the 1-octene contact the acquisition viscosity index with prepolymer as catalyzer and be at least 135 polyalphaolefin.
Hereinafter, the present invention is described below in further detail.
Common polyalphaolefin is used for motor oil or industry oil, and still the polyalphaolefin for preparing according to the present invention has high viscosity (for example kinetic viscosity is at least 90cSt in the time of 40 ℃, and viscosity index is at least 135), is of great use as industry oil.
In more detail, preparing in the method for polyalphaolefin the catalyst system that in the prepolymerization reaction of 1-decene or 1-dodecylene, uses EADC and TBC to form according to the present invention.
According to the present invention, the prepolymer of Huo Deing is used as catalyzer like this, and contacts production high viscosity polyalphaolefin with the 1-octene.
Preferably, the mol ratio of 1-octene and 1-decene or 1-dodecylene is in the 10-50 scope.If mol ratio is less than 10, because 1-decene or 1-dodecylene is excessive, this method is uneconomic.On the contrary, if mol ratio greater than 50, the add-on of 1-decene or 1-dodecylene is too little and the viscosity index that increases can not be provided.
Reaction conditions, i.e. the temperature and pressure of prepolymer and 1-octene reaction, preferred room temperature (for example 20-40 ℃ of scope is interior) and normal atmosphere (that is about 760mmHg).
If temperature of reaction is lower than 20 ℃, requires the expenditure of energy and cool off raw material.Otherwise if temperature of reaction is higher than 40 ℃, raw material must heat.
Embodiment
Hereinafter, describe the present invention further, but be not to limit scope of the present invention in the mode of following Example.
Example 1
300ml 1-octane is added to agitator, spiral coil cooling tube and thermometer is housed, remains under nitrogen atmosphere in 30 ℃ the 1L reactor.
In addition, 1-decene is added to ethylaluminum dichloride (EADC) and the 2.1ml8.99M tertiary butyl chloride (TBC) of 5.4ml 3.4M respectively, and making cumulative volume is 21ml, and the mol ratio of EADC and TBC is 1: 1.This mixture installs in the syringe then.Here the mol ratio of 1-octene and 1-decene is 10: 1.
Agitator, the condenser of band spiral coil cooling tube and the 500ml four neck flasks of thermometer are housed under nitrogen atmosphere, keep 30 ℃.Under agitation be expelled in this flask in 5 minutes with microsyringe with the mixture of the EADC of 1-decene dilution and TBC, restir obtained prepolymer in 5 minutes.Immediately this prepolymer is added in the syringe then.
Then, prepolymer is added in the 1L reactor that contains the 1-octene in 20 minutes with microsyringe.After injection finishes and stirs 30 minutes, remove catalyst residue with 200ml 0.1M NaOH.Lower boiling product and unconverted monomer are removed in the vacuum distilling under 180 ℃ and 1 holder of the product of removing residue, then filter distillation residue and obtain final product (productive rate is 77.3wt%).
Measure the kinetic viscosity and the viscosity index of the polyalphaolefin that obtains according to the regulation of KSM 2014.Measurement result is listed in table 1.
Example 2
Carry out prepolymerization reaction and ready reaction device according to the program that example 1 is described.The same way as that the program of back is described with example 1 is carried out, different is, in order after removing catalyst residue, distillation and filtration, to obtain the polyalphaolefin (productive rate is 76.8wt%) of low kinetic viscosity, the prepolymer that obtains was added in the 1L reactor with microsyringe in 10 minutes.
The polyalphaolefin that obtains is so also measured kinetic viscosity and viscosity index according to the description of example 1.Measurement result is listed in table 1.
Example 3
The same way as that 300ml 1-octane is described with example 1 is added in the 1L reactor.1-decene is added to ethylaluminum dichloride (EADC) and the 2.1ml 8.99M tertiary butyl chloride (TBC) of 5.4ml 3.4M respectively in addition, and making cumulative volume is 12.4ml, and the mol ratio of EADC and TBC is 1: 1.This mixture installs in the syringe then.Here the mol ratio of 1-octene and 1-decene is 20: 1.
The same way as that the program of back is described with example 1 is carried out, and different is that prepolymer was added in the 1L reactor with microsyringe in 20 minutes, obtained polyalphaolefin (productive rate is 80.4wt%) after removing catalyst residue, distillation and filtration.
The polyalphaolefin that obtains is so also measured kinetic viscosity and viscosity index according to the description of example 1.Measurement result is listed in table 1.
Example 4
The same way as that program is described with example 1 is carried out, different is, being added to catalyzer in the syringe and 1-decene is expelled in the 1L reactor in 5 minutes, after 5 minutes, under agitation 300ml 1-octene was expelled in the prepolymer in 20 minutes with microsyringe, after removing catalyzer, distillation and filtration, obtains polyalphaolefin (productive rate is 75.4wt%).
The polyalphaolefin that obtains is so also measured kinetic viscosity and viscosity index according to the description of example 1.Measurement result is listed in table 1.
Example 5
Same way as so that example 1 is described is added to the 1-octene in the 1L reactor, and 1-decene is added to ethylaluminum dichloride (EADC) and the 2.1ml 8.99M tertiary butyl chloride (TBC) of 5.4ml 3.4M respectively, and making cumulative volume is 20ml, and the mol ratio of EADC and TBC is 1: 1.This mixture installs in the syringe then.Here the mol ratio of 1-octene and 1-decene is 10: 1.
Agitator, the condenser of band spiral coil cooling tube and the 500ml four neck flasks of thermometer are housed under nitrogen atmosphere, keep 30 ℃.Be expelled in this flask under agitation 5 minutes with microsyringe with the mixture of the EADC of 1-decene dilution and TBC, restir obtained prepolymer in 5 minutes.Immediately this prepolymer is added in this syringe.The same way as that the program of back is described with example 1 is carried out, and obtains polyalphaolefin (productive rate is 79.7wt%).
The polyalphaolefin that obtains is so also measured kinetic viscosity and viscosity index according to the description of example 1.Measurement result is listed in table 1.
Example 6
Same way as with example 1 description, the 1-octene is added in the 1L reactor, 1-decene is added to ethylaluminum dichloride (EADC) and the 2.1ml 8.99M tertiary butyl chloride (TBC) of 5.4ml 3.4M respectively, and making cumulative volume is 12.2ml, and the mol ratio of EADC and TBC is 1: 1.This mixture installs in the syringe then.Here the mol ratio of 1-octene and 1-decene is 20: 1.
The same way as that the program of back is described with example 5 is carried out, and obtains polyalphaolefin (productive rate is 82.1wt%).
The polyalphaolefin that obtains is so also measured kinetic viscosity and viscosity index according to the description of example 1.Measurement result is listed in table 1.
Comparative Examples 1
300ml 1-octane is added to agitator, spiral coil cooling tube and thermometer is housed, remains under nitrogen atmosphere in 30 ℃ the 1L reactor.
In addition, the 1-octene is added to ethylaluminum dichloride (EADC) and the 2.1ml 8.99M tertiary butyl chloride (TBC) of 5.4ml 3.4M respectively, making cumulative volume is 21ml, and the mol ratio of EADC and TBC is 1: 1.This mixture installs in the syringe then.
Be expelled in this 1L reactor under agitation 20 minutes with microsyringe with the mixture of the EADC of 1-octene dilution and TBC.After injection finishes and stirs 30 minutes, remove catalyst residue with 200ml0.1M NaOH.The same way as that the program of back is described with example 1 is carried out, and obtains polyalphaolefin (productive rate is 80.4wt%) after removing catalyst residue, distillation and filtration.
The polyalphaolefin that obtains is so also measured kinetic viscosity and viscosity index according to the description of example 1.Measurement result is listed in table 1.
Comparative Examples 2
300ml 1-octane and 34.4ml 1-decene are added to agitator, spiral coil cooling tube and thermometer are housed, remain under nitrogen atmosphere in 30 ℃ the 1L reactor.Here the mol ratio of 1-octene and 1-decene is 10: 1.
The same way as that the program of back is described with Comparative Examples 1 is carried out, and prepares catalyzer, is expelled in the reactor in its 20 minutes, obtains polyalphaolefin (productive rate is 79.4wt%) after removing catalyst residue, distillation and filtration.
The polyalphaolefin that obtains is so also measured kinetic viscosity and viscosity index according to the description of example 1.Measurement result is listed in table 1.
Comparative Examples 3
300ml 1-octane and 34.4ml 1-dodecylene are added to agitator, spiral coil cooling tube and thermometer are housed, remain under nitrogen atmosphere in 30 ℃ the 1L reactor.Here the mol ratio of 1-octene and 1-dodecylene is 10: 1.
The same way as that the program of back is described with Comparative Examples 1 is carried out, and prepares catalyzer, is expelled in the reactor in its 20 minutes, obtains poly-C alkene (productive rate is 81.1wt%) after removing catalyst residue, distillation and filtration.
The polyalphaolefin that obtains is so also measured kinetic viscosity and viscosity index according to the description of example 1.Measurement result is listed in table 1.
Comparative Examples 4
The 344ml 1-decene is added to agitator, spiral coil cooling tube and thermometer is housed, remains under nitrogen atmosphere in 30 ℃ the 1L reactor.
In addition, the 1-octene is added to ethylaluminum dichloride (EADC) and the 2.1ml 8.99M tertiary butyl chloride (TBC) of 5.4ml 3.4M respectively, making cumulative volume is 21ml, and the mol ratio of EADC and TBC is 1: 1.This mixture installs in the syringe then.
Be expelled in this 1L reactor under agitation 5 minutes with microsyringe with the mixture of the EADC of 1-octene dilution and TBC.Through after 30 minutes, remove catalyst residue again with 200ml 0.1M NaOH.The same way as that the program of back is described with example 1 is carried out, and obtains polyalphaolefin (productive rate is 82.4wt%) after removing catalyst residue, distillation and filtration.
The polyalphaolefin that obtains is so also measured kinetic viscosity and viscosity index according to the description of example 1.Measurement result is listed in table 1.
Table 1
| The mol ratio of 1-octene/1-decene or 1-octene/1-dodecylene | The prepolymerization time (Min) | Reaction times (Min) | Kinetic viscosity in the time of 40 ℃ (cSt) | Viscosity index | ||
| A | ????1 | ????10 | ????10 | ????20 | ??124.6 | ????138 |
| ????2 | ????10 | ????10 | ????10 | ??94.7 | ????138 | |
| ????3 | ????20 | ????10 | ????20 | ??108.4 | ????136 | |
| ????4 | ????10 | ????5 | ????20 | ??101.5 | ????135 | |
| ????5 | ????10 | ????10 | ????20 | ??128.4 | ????141 | |
| ????6 | ????20 | ????10 | ????20 | ??114.2 | ????137 | |
| ?B | ????1 | ????∝ | ????0 | ????20 | ??77.1 | ????130 |
| ????2 | ????10 | ????0 | ????20 | ??93.5 | ????132 | |
| ????3 | ????10 | ????0 | ????20 | ??97.5 | ????134 | |
| ????4 | ????0 | ????0 | ????20 | ??103.3 | ????139 | |
Attention: A-example; The B-Comparative Examples
As above describe, a small amount of 1-decene of catalyst system prepolymerization or the 1-dodecylene that the present invention relates to use EADC and TBC to form, the prepolymerization product is contacted with the 1-octene.According to the present invention, use than the cheap 1-octene of 1-decene as main raw material, and a spot of 1-decene or dodecylene, making that high productivity is produced polyalphaolefin under the room temperature normal pressure becomes possibility, wherein, the polyalphaolefin that obtains like this has high kinetic viscosity, and the kinetic viscosity of the polyalphaolefin that obtains from the 1-decene monomer no better than is far above the kinetic viscosity of the polyalphaolefin that obtains from the 1-octene.The present invention also can easily control the kinetic viscosity of polyalphaolefin by the mol ratio of adjusting polyreaction or 1-octene and 1-decene or 1-dodecylene.
The applicability of industry
The high viscosity index (HVI) of polyalphaolefin of the present invention and low temperature flow make it have fabulous flowability in wide temperature range, with and narrow molecular weight distribution make when heating loss low, and having the high stability of long-term use, the base stock that can be used as automobile or industry oil uses.
Claims (4)
1. method for preparing polyalphaolefin comprises:
A spot of 1-decene of catalyzer prepolymerization or 1-dodecylene that use is made up of ethylaluminum dichloride (EADC) and tertiary butyl chloride (TBC) obtain prepolymer; And
Make the 1-octene be at least 135 polyalphaolefin with contacting as the prepolymer of catalyzer to obtain viscosity index.
2. method according to claim 1 is characterized in that, the prepolymerization temperature of 1-decene or 1-dodecylene is in 20-40 ℃ of scope, and the prepolymerization time is less than 10 minutes.
3. method according to claim 1 is characterized in that, per 1 mole of 1-decene or 1-dodecylene, and the addition of 1-octene is the 10-50 mole.
4. method according to claim 1 is characterized in that, being reflected under 20-40 ℃ temperature and the normal pressure of prepolymer and 1-octene carried out.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/KR2001/000702 WO2002088205A2 (en) | 2001-04-27 | 2001-04-27 | Method for preparing polyalphaolefin from 1-octene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1505643A true CN1505643A (en) | 2004-06-16 |
| CN1215097C CN1215097C (en) | 2005-08-17 |
Family
ID=19198375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN01823151.9A Expired - Lifetime CN1215097C (en) | 2001-04-27 | 2001-04-27 | Method for preparing polyalphaolefin from 1-octene |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN1215097C (en) |
| WO (1) | WO2002088205A2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113528214A (en) * | 2020-04-14 | 2021-10-22 | 印度石油有限公司 | Method for controlling kinematic viscosity of poly-alpha-olefins |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7550640B2 (en) * | 2005-01-14 | 2009-06-23 | Exxonmobil Chemical Patents Inc. | High viscosity PAOs based on 1-decene/1-dodecene |
| US9382349B2 (en) * | 2012-08-03 | 2016-07-05 | Exxonmobil Chemical Patents Inc. | Polyalphaolefins prepared using modified Salan catalyst compounds |
| CN104411778B (en) * | 2012-08-03 | 2017-07-28 | 埃克森美孚化学专利公司 | The polyalphaolefin prepared using modified Salan catalyst compounds |
| RU2666725C1 (en) * | 2018-06-22 | 2018-09-12 | Публичное Акционерное Общество "Нижнекамскнефтехим" | Method of producing polyalphaolefins with kinematic viscosity of 10-25 cst |
| US11198745B2 (en) * | 2018-11-29 | 2021-12-14 | Exxonmobil Chemical Patents Inc. | Poly(alpha-olefin)s and methods thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51124186A (en) * | 1975-04-22 | 1976-10-29 | Lion Corp | Preparation of liquid olefin polymer |
| US4045507A (en) * | 1975-11-20 | 1977-08-30 | Gulf Research & Development Company | Method of oligomerizing 1-olefins |
| US4045508A (en) * | 1975-11-20 | 1977-08-30 | Gulf Research & Development Company | Method of making alpha-olefin oligomers |
| 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 |
| CA2091303A1 (en) * | 1992-03-16 | 1993-09-17 | Dirk M. Sutherlin | Polymerization process to prepare a polyolefin from sterically hindered, methyl branched, alpha-olefins |
| DE4415912A1 (en) * | 1994-05-05 | 1995-11-09 | Linde Ag | Process for oligomerizing alpha-olefins to poly-alpha-olefins |
-
2001
- 2001-04-27 CN CN01823151.9A patent/CN1215097C/en not_active Expired - Lifetime
- 2001-04-27 WO PCT/KR2001/000702 patent/WO2002088205A2/en active Application Filing
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113528214A (en) * | 2020-04-14 | 2021-10-22 | 印度石油有限公司 | Method for controlling kinematic viscosity of poly-alpha-olefins |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002088205A2 (en) | 2002-11-07 |
| WO2002088205A3 (en) | 2002-12-27 |
| CN1215097C (en) | 2005-08-17 |
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Granted publication date: 20050817 |