CN103289731B - Method for preparing synthetic hydrocarbon containing aromatic hydrocarbon from internal olefin - Google Patents
Method for preparing synthetic hydrocarbon containing aromatic hydrocarbon from internal olefin Download PDFInfo
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- CN103289731B CN103289731B CN201210047320.3A CN201210047320A CN103289731B CN 103289731 B CN103289731 B CN 103289731B CN 201210047320 A CN201210047320 A CN 201210047320A CN 103289731 B CN103289731 B CN 103289731B
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- internal olefin
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Abstract
The invention discloses a method for preparing synthetic hydrocarbon containing aromatic hydrocarbon from internal olefin, and belongs to the technical field of synthetic hydrocarbon preparation. The method is as follows: the synthetic hydrocarbon containing the aromatic hydrocarbon is obtained by carrying out an alkylation reaction under the action of an aluminium trichloride catalyst and a cocatalyst by taking alkylbenzene and the internal olefin as raw materials; the number of carbon atoms contained in the alkyl of the alkylbenzene is 1-260, and the internal olefin contains 8-14 carbon atoms; and the prepared synthetic hydrocarbon containing the aromatic hydrocarbon achieves the aromatic hydrocarbon of 5%-10% by weight, the pour point of -28 to -42 DEG C, the flash point of 250-300 degrees, the kinematic viscosity of 22-110 and the viscosity index of 130-180. The method disclosed by the invention has the advantages of wide raw material source and low price; and the prepared synthetic hydrocarbon not only has all the property of PAO synthetic hydrocarbon oil, but also has the characteristics of alkylbenzene synthetic oil, does not need high temperature and high pressure in a production process and is energy-saving and environment-friendly.
Description
Technical field
The invention belongs to synthesis hydrocarbon preparing technical field, be specifically related to the method for a kind of internal olefin preparation containing aromatic hydrocarbons synthesis hydrocarbon.
Background technology
Synthesis hydrocarbon, also claiming synthetic hydrocarbon oil, is the hydro carbons lubricating oil prepared by chemical process, and it comprises poly-alpha olefins (PAO), polybutene, alkylaromatic hydrocarbon and synthesis cycloalkanes etc.Wherein poly-alpha olefins (PAO) be in the world consumption at most, be considered to have most the synthetic lubricant base oil of development potentiality.Poly-alpha olefins (PAO) synthesis consists essentially of two steps, first 'alpha '-olefin monomers is made to be polymerized in the presence of a catalyst, generate the unsaturated polymer containing double bond, just must carry out hydroprocessing to make double bond saturated thus to improve the performance of product to it afterwards, have after hydrogenation: viscosity index is high, pour point is low, heat-resistant quality and the advantage such as oxidation stability is good.Based on PAO importance industrially, the alpha-olefin cost therefore as its main raw material is higher.
Poly-internal olefin (PIO) is as a kind of new ucon oil, and be once called VI class base oil by ACEA, it is polymerized by internal olefin, its structure and PAO similar, have the fundamental characteristics of PAO, price is also low than PAO by 15 ~ 20%.The number of ways such as by product, low-carbon alkene oligomerisation that internal olefin can produce alpha-olefin by catalytic dehydrogenation-separation of alkane and olefin technique, SHOP method obtains, and internal olefin importance is industrially not as alpha-olefin, thus price comparatively alpha-olefin is cheap.Therefore, based on PIO, oil has a good application prospect in high performance internal combustion engine oil and industry oil.
At present, poly-alpha olefins (PAO) production and obtained in poly-internal olefin (PIO) its preparation process by the method such as internal olefin oligomerisation and need to carry out hydrotreatment.Current industrialization hydrogenation process all adopts high-pressure hydrogenation process, and its energy consumption is high, and industrial device investment is large.If the synthetic hydrocarbon oil with above-mentioned advantageous property can be obtained under the prerequisite not adopting hydrotreatment, it will be a great leap of art technology.
Summary of the invention
A kind of internal olefin is the object of the present invention is to provide to prepare the method for synthesizing hydrocarbon containing aromatic hydrocarbons, the raw materials used wide material sources of the method, cheap, prepared synthesis hydrocarbon not only possesses all properties of PAO synthetic hydrocarbon oil, also possess alkylbenzene synthetic oil characteristic, production process is without the need to High Temperature High Pressure, energy-conserving and environment-protective simultaneously.
Technical scheme of the present invention is:
Internal olefin preparation is containing a method for aromatic hydrocarbons synthesis hydrocarbon, and the method is with alkylbenzene and internal olefin for raw material, carries out alkylated reaction, thus obtain containing aromatic hydrocarbons synthesis hydrocarbon under the effect of aluminum trichloride catalyst and promotor; Its alkyl institute carbon atom quantity of described alkylbenzene is 1 ~ 260, and described internal olefin is the internal olefin containing 8 ~ 14 carbon atoms; In mass fraction, each component content is:
The described internal olefin containing 12 carbon atoms, by the preparation of the dehydrating alkanes of 12 carbon or to gather legal system by propylene four standby; Wherein: the mass content 98% of its linear structure of internal olefin prepared by the dehydrating alkanes of 12 carbon, the mass content 30 ~ 50% of standby its linear chain structure of internal olefin of legal system, the mass content 50 ~ 70% of branched structure is gathered by propylene four.
Described promotor the polyaniline of conductive state and N-Methyl pyrrolidone is mixed afterwards and add ammoniacal liquor to stir the high connductivity state complex compound formed, wherein: the part by weight of the polyaniline of conductive state, N-Methyl pyrrolidone and ammoniacal liquor is (10 ~ 15): (70 ~ 80): (10 ~ 15), temperature of reaction 30 ~ 50 DEG C, churning time 2 ~ 5 hours.
Described alkylated reaction carries out in a nitrogen atmosphere, wherein: nitrogen pressure 2 ~ 2.5kg/cm
2, temperature of reaction 25 ~ 30 DEG C, 1 ~ 6 hour reaction times.
Prepared by aforesaid method, synthesize hydrocarbon containing aromatic hydrocarbons, aromatics quality percentage composition is 5 ~ 10%, pour point-28 ~-42 DEG C, flash-point 250 ~ 300 degree, kinematic viscosity 22 ~ 110, viscosity index 130 ~ 180.
Beneficial effect of the present invention is as follows:
What 1, the present invention was prepared with internal olefin synthesizes hydrocarbon containing aromatic hydrocarbons, not only has all properties of PAO synthetic oil, also has the characteristic of alkylbenzene synthetic oil: the mutual solubility had with mineral oil, synthetic fat; The solvability had with various lubricating oil additive.
2, be all by olefin copolymerization process preparation synthesis hydrocarbon base oil in prior art, alkylation process needs hydrogenation, and the alkylated reaction that the present invention is alkylbenzene and internal olefin to be carried out under the effect of aluminum trichloride catalyst and promotor, the alkene in traditional method is replaced with alkylbenzene, because its alkylated reaction does not need hydrogenation, therefore in production process without High Temperature High Pressure, safety energy-conserving environment protection, and invest little, easy industrialization, and the olefin-copolymerization in traditional method.
3, the present invention replaces the alkene in traditional method with alkylbenzene, thus aromatic hydrocarbon molecule is introduced in synthesis hydrocarbon, compared to the contained aromatic hydrocarbons of traditional synthesis hydrocarbon (PAO), its resistance to emulsion and the property sheared are improved greatly, have good swelling property with various rubber packing material.
4, the present invention carries out alkylation preparation containing aromatic hydrocarbons synthesis hydrocarbon base oil or the first in the world with internal olefin, because internal olefin is cheap, thus greatly reduces costs, can be suitable with mineral oil price; Meanwhile, the prepared aromatic hydrocarbons synthesis hydrocarbon base oil indices that contains reaches or surmounts the synthesis hydrocarbon base oil that ethylene oligomerization alpha-olefin is raw material.
5, the promotor of the present invention's employing is novel unique, active superpower, there is history breakthrough, conductive polyaniline is dissolved in N-Methyl pyrrolidone, the high connductivity state complex compound formed has very strong electronics base under the existence of ammoniacal liquor, it mix with certain proportion with aluminum chloride after to alkane of the present invention, it is changed reaction and has strong katalysis.
Accompanying drawing explanation
Fig. 1 is the hydrogen nuclear magnetic resonance spectrogram that the embodiment of the present invention 3 prepares containing aromatic hydrocarbons synthesis hydrocarbon.
Fig. 2 is the carbon-13 nmr spectra figure that the embodiment of the present invention 3 prepares containing aromatic hydrocarbons synthesis hydrocarbon.
Embodiment
In the present invention, the end group of the alkyl of internal olefin and alkylbenzene reacts, and carbon atom number can reach 30 to 40, not only carries out linear response and also carries out branching reaction.
Below in conjunction with accompanying drawing and embodiment in detail the present invention is described in detail, in embodiment, involved component content is parts by weight.The carbon of internal olefin described in embodiment 12 refers to the internal olefin containing 12 C prepared by the dehydrating alkanes of 12 carbon, its linear content 98%; Described tetrapropylene (carbon 12) refer to by propylene four gather legal system standby containing the internal olefin of 12 C, its straight chain formula structural content 30 ~ 50%, a chain type structural content 50 ~ 70%.In embodiment, corresponding data test method is:
100 DEG C of kinematic viscosity: ASTM D445;
Pour point: ASTM D97;
Viscosity index: ASTM D2270;
Heavy oil fraction boiling Range Distribution Analysis: ASTMD6352 heavy oil fraction boiling Range Distribution Analysis assay method.
Embodiment 1
1, the preparation of promotor:
Under 30 ~ 50 DEG C of conditions, stirring adding ammoniacal liquor 12 parts again after the polyaniline 10 parts of conductive state and N-Methyl pyrrolidone 75 parts mixing 2 hours, obtaining promotor.
2, containing the preparation of aromatic hydrocarbons synthesis hydrocarbon:
Tetrapropylene (carbon 12) 35 parts and dodecylbenzene 10 parts is adopted to be raw material, alkylated reaction is carried out under aluminum trichloride catalyst (1.5 parts) and promotor (0.6 part) effect, alkylated reaction carries out in a nitrogen atmosphere, nitrogen pressure 2 ~ 2.5kg/cm
2, temperature of reaction 25 ~ 30 DEG C, 6 hours reaction times.Carry out washing neutralization after alkylated reaction, after pH value becomes neutrality, refining filtering after underpressure distillation dehydration under 80 DEG C of conditions, obtains containing aromatic hydrocarbons synthesis hydrocarbon.
3, the present embodiment is containing aromatic hydrocarbons synthesis hydrocarbon performance: pour point :-42 degree, flash-point: 252 degree, kinematic viscosity: 100 degree 22, viscosity index: 130.
Embodiment 2
1, the preparation of promotor: with embodiment 1.
2, containing the preparation of aromatic hydrocarbons synthesis hydrocarbon:
12 parts, internal olefin carbon and dodecylbenzene 10 parts is adopted to be raw material, alkylated reaction is carried out under aluminum trichloride catalyst (1.5 parts) and promotor (0.6 part) effect, alkylated reaction carries out in a nitrogen atmosphere, nitrogen pressure 2 ~ 2.5kg/cm
2, temperature of reaction 25 ~ 30 DEG C, 6 hours reaction times.Carry out washing neutralization after alkylated reaction, after pH value becomes neutrality, refining filtering after underpressure distillation dehydration under 80 DEG C of conditions, obtains containing aromatic hydrocarbons synthesis hydrocarbon.
3, the present embodiment is containing aromatic hydrocarbons synthesis hydrocarbon performance: pour point :-40 degree, flash-point: 252 degree, kinematic viscosity: 100 degree 23, viscosity index: 135.
Embodiment 3
1, the preparation of promotor:
Under 30 ~ 50 DEG C of conditions, stirring adding ammoniacal liquor 14 parts again after the polyaniline 11 parts of conductive state and N-Methyl pyrrolidone 70 parts mixing 3.5 hours, obtaining promotor.
2, containing the preparation of aromatic hydrocarbons synthesis hydrocarbon:
Tetrapropylene (carbon 12) 50 parts and dodecylbenzene 5 parts is adopted to be raw material, alkylated reaction is carried out under aluminum trichloride catalyst (1.6 parts) and promotor (0.7 part) effect, alkylated reaction carries out in a nitrogen atmosphere, nitrogen pressure 2 ~ 2.5kg/cm
2, temperature of reaction 25 ~ 30 DEG C, 5 hours reaction times.Carry out washing neutralization after alkylated reaction, after pH value becomes neutrality, refining filtering after underpressure distillation dehydration under 80 DEG C of conditions, obtains containing aromatic hydrocarbons synthesis hydrocarbon.As shown in Figure 1-2, show that product molecular weight distribution is balanced through carbon-13 nmr spectra and proton nmr spectra test observation, and the display of aromatic hydrocarbons peak value obviously.
3, the present embodiment is containing aromatic hydrocarbons synthesis hydrocarbon performance: pour point :-35 degree, flash-point: 282 degree, kinematic viscosity: 100 degree 42, viscosity index: 150.
Record cut boiling Range Distribution Analysis: 350-500 degree: 12%, be greater than 500 degree: 88%.
Embodiment 4
1, the preparation of promotor: with embodiment 3
2, containing the preparation of aromatic hydrocarbons synthesis hydrocarbon:
12 parts, internal olefin carbon and dodecylbenzene 5 parts is adopted to be raw material, alkylated reaction is carried out under aluminum trichloride catalyst (1.6 parts) and promotor (0.7 part) effect, alkylated reaction carries out in a nitrogen atmosphere, nitrogen pressure 2 ~ 2.5kg/cm
2, temperature of reaction 25 ~ 30 DEG C, 5 hours reaction times.Carry out washing neutralization after alkylated reaction, after pH value becomes neutrality, refining filtering after underpressure distillation dehydration under 80 DEG C of conditions, obtains containing aromatic hydrocarbons synthesis hydrocarbon.
3, the present embodiment is containing aromatic hydrocarbons synthesis hydrocarbon performance: pour point :-33 degree, flash-point: 282 degree, kinematic viscosity: 100 degree 45, viscosity index: 152.
Record cut boiling Range Distribution Analysis: 350-500 degree: 12%, be greater than for 500 degree: 88% (as shown in Figure 1-2).
Embodiment 5
1, the preparation of promotor:
Under 30 ~ 50 DEG C of conditions, stirring adding ammoniacal liquor 10 parts again after the polyaniline 13 parts of conductive state and N-Methyl pyrrolidone 75 parts mixing 4 hours, obtaining promotor.
2, containing the preparation of aromatic hydrocarbons synthesis hydrocarbon:
12 parts, internal olefin carbon and toluene 5 parts is adopted to be raw material, alkylated reaction is carried out under aluminum trichloride catalyst (3.3 parts) and promotor (1.3 parts) effect, alkylated reaction carries out in a nitrogen atmosphere, nitrogen pressure 2 ~ 2.5kg/cm
2, temperature of reaction 25 ~ 30 DEG C, 6 hours reaction times.Carry out washing neutralization after alkylated reaction, after pH value becomes neutrality, refining filtering after underpressure distillation dehydration under 80 DEG C of conditions, obtains containing aromatic hydrocarbons synthesis hydrocarbon.
3, the present embodiment is containing aromatic hydrocarbons synthesis hydrocarbon performance: pour point :-28 degree, flash-point: 300 degree, kinematic viscosity: 100 degree 105, viscosity index: 180.
Record cut boiling Range Distribution Analysis: be greater than 500 degree: 100%.
Embodiment 6
1, the preparation of promotor: with embodiment 5.
2, containing the preparation of aromatic hydrocarbons synthesis hydrocarbon:
12 parts, internal olefin carbon and toluene 5 parts is adopted to be raw material, alkylated reaction is carried out under aluminum trichloride catalyst (3.3 parts) and promotor (1.3 parts) effect, alkylated reaction carries out in a nitrogen atmosphere, nitrogen pressure 2 ~ 2.5kg/cm
2, temperature of reaction 25 ~ 30 DEG C, 6 hours reaction times.Carry out washing neutralization after alkylated reaction, after pH value becomes neutrality, refining filtering after underpressure distillation dehydration under 80 DEG C of conditions, obtains containing aromatic hydrocarbons synthesis hydrocarbon.
3, the present embodiment is containing aromatic hydrocarbons synthesis hydrocarbon performance: pour point :-28 degree, flash-point: 300 degree, kinematic viscosity: 100 degree 110, viscosity index: 180.
Record cut boiling Range Distribution Analysis: be greater than 500 degree: 100%.
Above-mentioned example shows simultaneously, and what the present invention was prepared for raw material with alkylbenzene and internal olefin synthesizes hydrocarbon base oil containing aromatic hydrocarbons, has both maintained the fundamental property of PAO, cheap again, using substituting or supplementing and be with a wide range of applications as PAO.
Claims (6)
1. internal olefin preparation is containing a method for aromatic hydrocarbons synthesis hydrocarbon, it is characterized in that: the method is with alkylbenzene and internal olefin for raw material, carries out alkylated reaction, thus obtain containing aromatic hydrocarbons synthesis hydrocarbon under the effect of aluminum trichloride catalyst and promotor; Its alkyl institute carbon atom quantity of described alkylbenzene is 1 ~ 260, and described internal olefin is the internal olefin containing 8 ~ 14 carbon atoms; In mass fraction, each component content is:
Described promotor to add ammoniacal liquor and stir the high connductivity state complex compound formed after the polyaniline of conductive state and N-Methyl pyrrolidone mixing, and the part by weight of the polyaniline of conductive state, N-Methyl pyrrolidone and ammoniacal liquor is (10 ~ 15): (70 ~ 80): (10 ~ 15); In promotor preparation process, temperature of reaction 30 ~ 50 DEG C, churning time 2 ~ 5 hours.
2. method according to claim 1, is characterized in that: described internal olefin is the internal olefin containing 12 carbon atoms.
3. method according to claim 2, is characterized in that: the described internal olefin containing 12 carbon atoms, by the preparation of the dehydrating alkanes of 12 carbon or to gather legal system by propylene four standby; Wherein: the mass content 98% of its linear structure of internal olefin prepared by the dehydrating alkanes of 12 carbon, the mass content 30 ~ 50% of standby its linear chain structure of internal olefin of legal system, the mass content 50 ~ 70% of branched structure is gathered by propylene four.
4. method according to claim 1, is characterized in that: described alkylated reaction carries out in a nitrogen atmosphere, wherein: nitrogen pressure 2 ~ 2.5kg/cm
2, temperature of reaction 25 ~ 30 DEG C, 1 ~ 6 hour reaction times.
5. according to the arbitrary described method of claim 1-4, it is characterized in that: prepared containing aromatic hydrocarbons synthesis hydrocarbon, aromatics quality percentage composition is 5 ~ 10%.
6. according to the arbitrary described method of claim 1-4, it is characterized in that: prepared containing aromatic hydrocarbons synthesis hydrocarbon, pour point-28 ~-42 DEG C, flash-point 250 ~ 300 degree, kinematic viscosity 22 ~ 110, viscosity index 130 ~ 180.
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| CN109749777A (en) * | 2017-11-02 | 2019-05-14 | 中国石油大学(华东) | A method of producing environmental-friendly rubber filling oil |
| CN109749776A (en) * | 2017-11-02 | 2019-05-14 | 中国石油大学(华东) | A method of utilizing diesel production environmental-friendly rubber filling oil |
| EP3896141B1 (en) * | 2020-04-14 | 2023-08-30 | Indian Oil Corporation Limited | Method of controlling kinematic viscosity of polyalphaolefin |
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|---|---|---|---|---|
| US5008460A (en) * | 1989-05-30 | 1991-04-16 | Mobil Oil Corp. | Synthetic lubricants |
| CN101365663A (en) * | 2005-12-20 | 2009-02-11 | 雪佛龙美国公司 | Lubricant or fuel blendstock made by ionic liquid oligomerization of olefins in the presence of isoparaffins |
| CN102344824A (en) * | 2011-09-06 | 2012-02-08 | 刘峰 | Preparation method of arene-containing synthetic hydrocarbon |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| FI941529A (en) * | 1994-03-31 | 1995-10-01 | Neste Oy | Process for oligomerization of C4 oils with long chain olefins |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5008460A (en) * | 1989-05-30 | 1991-04-16 | Mobil Oil Corp. | Synthetic lubricants |
| CN101365663A (en) * | 2005-12-20 | 2009-02-11 | 雪佛龙美国公司 | Lubricant or fuel blendstock made by ionic liquid oligomerization of olefins in the presence of isoparaffins |
| CN102344824A (en) * | 2011-09-06 | 2012-02-08 | 刘峰 | Preparation method of arene-containing synthetic hydrocarbon |
Non-Patent Citations (1)
| Title |
|---|
| "高碳内烯烃在合成聚烯烃润滑油中的应用";许林林等;《天津化工》;20100930;第24卷(第5期);1-3 * |
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