CN102344824A - Preparation method of arene-containing synthetic hydrocarbon - Google Patents
Preparation method of arene-containing synthetic hydrocarbon Download PDFInfo
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- CN102344824A CN102344824A CN2011102628793A CN201110262879A CN102344824A CN 102344824 A CN102344824 A CN 102344824A CN 2011102628793 A CN2011102628793 A CN 2011102628793A CN 201110262879 A CN201110262879 A CN 201110262879A CN 102344824 A CN102344824 A CN 102344824A
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- synthetic hydrocarbon
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- olefin
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
The invention provides a preparation method of an arene-containing synthetic hydrocarbon, belonging to the technical field of synthetic hydrocarbon preparation. The preparation method comprises the following steps of: carrying out an alkylation reaction on alkylbenzene and alpha-olefin used as raw materials under the action of an aluminum trichloride catalyst and a catalyst promoter; refining the product obtained after the alkylation reaction in an ion exchanger; and removing the catalyst, assistants, hydrogen chloride and chloride ions in the product through an ion exchange resin in the ion exchanger to obtain the arene-containing synthetic hydrocarbon. By adopting the alkylation reaction, a hydrogenation process is not required, thereby ensuring no high pressure and high temperature in the production process; and in the post-treatment refining process, the ion exchange resin is used to remove the catalyst promoter, oxide and chloride ions in the synthetic oil, thereby greatly improving the oxidation stability of the product and having the advantages of energy conservation and environmental protection. The prepared arene-containing synthetic hydrocarbon has all the properties of PAO (poly-alpha-olefin) synthetic hydrocarbon oil, and also has the characteristics of alkylbenzene synthetic oil.
Description
Technical field
The invention belongs to synthetic hydrocarbon preparing technical field, be specifically related to a kind of preparation method who contains the synthetic hydrocarbon of aromatic hydrocarbons.
Background technology
Synthetic hydrocarbon is also claimed synthetic hydrocarbon oil, is the hydro carbons lubricating oil by the chemical process preparation, and it comprises poly-alpha olefins (PAO), polybutene, alkylaromatic hydrocarbon and synthetic cycloalkanes etc.Wherein PAO has consequence in lubricating oil market.With respect to crude mineral oils; PAO has higher thermostability, viscosity index and oxidation-resistance; The loss of low high temperature evaporation, good low-temperature fluidity, frictional behaviour, stability to hydrolysis, erosion resistance, and nontoxicity, coking are few, can be miscible with mineral oil and ester.Based on above-mentioned performance, PAO is widely used in high-grade I. C. engine oil, compressor oil, hydraulic efficiency oil, gear oil and lubricating grease.Along with people for energy-conservation and attention environmental protection, also make the fast development of speed of poly-alpha olefins with about 10-15% in every year.
The production of poly-alpha olefins generally is to be raw material with the alpha-olefin, in the presence of catalyzer such as aluminum halide, aikyl aluminum halide, BF3, carries out (CN101054332A) that polymerization prepares.Use alkali metal aluminosilicate (United States Patent (USP) 3322848) and zeolite catalyst carry out polyolefinic synthetic (United States Patent (USP) 6703356B1 number) also bibliographical information have been arranged.The method that is used to produce the PAO lubricant is disclosed in many patents.For example referring to United States Patent (USP) No. 3149178, No. 3382291, No. 3742082, No. 3780128, No. 4172855, No. 4956122 and Chinese patent CN101102982, CN1332005C etc.
United States Patent (USP) has been described for No. 3113167 halogenated titanium has been combined with aikyl aluminum halide, through changing the character that catalyst proportion and reaction conditions change product.Disclosed in Chinese patent ZL200310120887 number generated in-situ aluminum chloride catalyst has been loaded on the gama-alumina with mesoporous and macropore, made alpha-olefin polymerization in fixed-bed reactor, to carry out.Also many bibliographical informations have been arranged phosphoric acid (No. the 4982026th, United States Patent (USP)), alcohol promotor such as (No. the 5994605th, United States Patent (USP)s) are combined with catalyzer to use, to improve the performance of product.Chinese patent has then been described a kind of alpha-olefin synthetic catalyst system of uniqueness for ZL02817015.6 number; This catalyst system uses the Metallocenic compound catalyzer of metals such as zirconium, titanium, hafnium; Be aided with the aluminum alkoxide promotor, make the product make not contain isomerization basically and the tertiary hydrogen that produces.
One Chinese patent application discloses has pointed out a kind of preparation to be used for the method for the polyalphaolefin of industry oil in CN1505643A number.In this method, at first in the presence of haloalkyl aluminium and halogenated alkane catalyzer, make 1-decene and 1 one dodecylene generation oligomerizations to generate a spot of oligopolymer.Then in the presence of this oligomer mixture, make the 1-decene generation polymerization that price is comparatively cheap, generate and have required full-bodied poly-alpha olefins.Above-mentioned high viscosity PAO is meant through the described method of ASTM D445 and records kinematic viscosity under 100 ℃ greater than the PAO of 20cst, usually by linear alpha-alkene through the cationic oligomeric prepared in reaction.
Above-mentioned different patent all is to improve performance of products and productive rate from different perspectives, reduce production costs and complexity, to improve competitiveness of product.A kind of mode is to adopt composite catalyst, and a kind of to be to use a certain proportion of comparatively cheap hydro carbons be the high-quality synthetic hydrocarbon oil of raw material production.
In above-mentioned patent documentation; PAO synthetic consists essentially of two steps; At first make 'alpha '-olefin monomers in the presence of catalyzer, carry out polymerization; Generation contains the unsaturated polymer of two keys; Thereby just must carry out hydroprocessing so that the antioxidative stabilizer of the saturated raising of two key product afterwards to it; Industrialization hydrogenation process all adopts high-pressure hydrogenation process at present, and its energy consumption is high, and the industrialization facility investment is big.If can under the prerequisite that does not adopt hydrotreatment, make synthetic hydrocarbon oil, will be a great leap of art technology with above-mentioned advantageous property.
Summary of the invention
The object of the present invention is to provide a kind of preparation method who contains the synthetic hydrocarbon of aromatic hydrocarbons, this preparation method does not need hydrogenation because of alkylated reaction, and the aftertreatment process for refining adopts ion-exchange method to replace traditional washing process, and production process does not have High Temperature High Pressure, energy-conserving and environment-protective.Prepared synthetic hydrocarbon not only possesses all properties of PAO synthetic hydrocarbon oil, also has alkylbenzene synthetic oil characteristic.
Technical scheme of the present invention is: a kind of preparation method who contains the synthetic hydrocarbon of aromatic hydrocarbons is specially:
Alkylation process: with alkylbenzene and alpha-olefin is raw material, under the effect of aluminum trichloride catalyst and promotor, carries out alkylated reaction, obtains containing the synthetic hydrocarbon crude product of aromatic hydrocarbons; Said alkylbenzene is the alkylbenzene that alkyl contains 1 to 260 carbon atom, and said alpha-olefin is the alpha-olefin that contains 8 to 14 carbon atoms; The parts by weight of above-mentioned each component are:
Said alkylated reaction carries out under nitrogen atmosphere; Nitrogen pressure 2～2.5kg/cm
2, 10～30 ℃ of temperature of reaction, 1～6 hour reaction times.
Said promotor prepares process: after polyvinyl alcohol and ethanol mixing; Add aqua ammonia (ammoniacal liquor) down at 30～40 ℃; Add sodium hydroxide and potassium hydroxide after 5～6 hours again, under 70～150 rotary speeds, stir the basic complex that formed in 2～3 hours and be promotor; Said polyvinyl alcohol is a low molecular weight polyethylene alcohol, and molecular weight is 25000～35000.
The parts by weight of above-mentioned each component are following:
Aftertreatment technology: with gained behind the alkylated reaction contain the synthetic hydrocarbon crude product of aromatic hydrocarbons send in the ion-exchanger refining, remove catalyzer, auxiliary agent and the chlorion in the product through the ion exchange resin in the ion-exchanger after, make and contain the synthetic hydrocarbon of aromatic hydrocarbons.
The prepared synthetic hydrocarbon of aromatic hydrocarbons that contains, aromatic hydrocarbons quality percentage composition is 5～10%, pour point-20～-50 ℃, 230～350 ℃ of flash-points, kinematic viscosity 15～120, viscosity index 120～200.
The present invention has following beneficial effect:
1, the present invention contains the synthetic hydrocarbon of aromatic hydrocarbons, not only has all properties of PAO synthetic hydrocarbon oil, also has the characteristic of alkylbenzene synthetic oil: with mineral oil, synthetic fat good mutual solubility is arranged; With various lubricating oil additives good solvability is arranged; Contained aromatic hydrocarbons makes it have good resistance to emulsion and the property sheared, and with various rubber packing materials good swelling property is arranged.
2, the present invention so does not have High Temperature High Pressure, safety energy-conserving environment protection because alkylated reaction does not need hydrogenation in the production process, and invests for a short time, is prone to industrialization.
3, aftertreatment process for refining of the present invention adopts ion exchange resin can remove promotor, oxide compound and chlorion in the synthetic oil, improves the oxidation-stabilized performance of product greatly, than traditional washing process, also has advantages of energy saving and environmental protection.
Embodiment
The end group of the alkyl of a-alkene and alkylbenzene reacts among the present invention, and the carbon atom number can reach 30 to 40, not only carries out linear response and also carries out branching reaction.Through embodiment the present invention is detailed below.
Institute's spent ion exchange resin is purchased the auspicious promise chemical industry company limited in Qingdao among the embodiment, comprises two kinds:
1, the resin trade mark: KC-10
Describe: KC-10 gel-type polystyrene polymeric adsorbent; It is the polymeric adsorbent of modification on traditional gel-type phenylethylene resin series basis; Making resin have better absorption and analysis feature through the improved resins skeleton structure, is the polymeric adsorbent product of new generation of the auspicious promise chemical industry research and development in Qingdao.
KC-10 polymeric adsorbent composition: poly styrene sulfonate composition 50%, moisture 50%.
Outward appearance: transparent spherical particle.
Technical indicator: size range 16-50 order, moisture 45-55%, density 0.6-0.8g/ml.
2, the resin trade mark: KC-10H
Describe: KC-10H macroporous type polystyrene polymeric adsorbent; It is the polymeric adsorbent of modification on traditional macroporous type phenylethylene resin series basis; Making resin have better absorption and analysis feature through the improved resins skeleton structure, is the polymeric adsorbent product of new generation of the auspicious promise chemical industry research and development in Qingdao.
KC-10H polymeric adsorbent composition: poly styrene sulfonate composition 50%, moisture 50%.
Outward appearance: brown spherical particle.
Technical indicator: size range 16-50 order, moisture 45-55%, density 0.6-0.8g/ml.
The corresponding data test method of following embodiment is:
100 ℃ 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, promotor preparation:
After polyvinyl alcohol and ethanol mixing, 30 ℃ add aqua ammonia (ammoniacal liquor) down, add sodium hydroxide and potassium hydroxide after 5 hours again, and 80 rotary speeds stir 2 hours formation promotors down;
The parts by weight of above-mentioned each component are following:
2, adopt dodecylbenzene and C
10Alpha-olefin, aluminum chloride and promotor alkylated reaction, the raw material weight umber is:
Dodecylbenzene: 10 parts
C
10Alhpa olefin: 35 parts
Aluminum chloride: 1.5 parts
Promotor: 0.6 part
Processing condition: earlier dodecylbenzene is pumped in the reactor, aluminum chloride and promotor is added again, agitator is full of nitrogen in the reactor again, nitrogen pressure 2～2.5Kg/cm
2, with pumping C
10Alhpa olefin slowly drips, 10 ℃ of temperature of reaction, 1 hour reaction times.
3, sintetics is refining
Behind the alkylated reaction product is sent in the ion-exchanger refining.
Ion exchange resin is housed in the ion-exchanger.
The product pour point-45 that present embodiment obtains ℃, 252 ℃ of flash-points, 100 ℃ of kinematic viscosity 20, viscosity index 138; Record cut boiling Range Distribution Analysis: 350-500 ℃: 20%, greater than 500 ℃: 80%.
Embodiment 2
1, promotor preparation:
After polyvinyl alcohol and ethanol mixing, 35 ℃ add aqua ammonia (ammoniacal liquor) down, add sodium hydroxide and potassium hydroxide after 5 hours again, and 140 rotary speeds stir 2 hours formation promotors down;
The parts by weight of above-mentioned each component are following:
2, adopt dodecylbenzene and C
10Alpha-olefin, aluminum chloride and promotor alkylated reaction, the raw material weight umber is:
Dodecylbenzene: 10 parts
C
10Alhpa olefin: 35 parts
Aluminum chloride: 0.9 part
Promotor: 0.4 part
Processing condition: earlier dodecylbenzene is pumped in the reactor, aluminum chloride and promotor is added again, agitator is full of nitrogen in the reactor again, nitrogen pressure 2～2.5Kg/cm
2, with pumping C
10Alpha-olefin slowly drips, 10 ℃ of temperature of reaction, 1 hour reaction times.
3, sintetics is refining
Behind the alkylated reaction product is sent in the ion-exchanger refining.
The product pour point-48 that present embodiment obtains ℃, 242 ℃ of flash-points, 100 ℃ of kinematic viscosity 18, viscosity index 130.
Embodiment 3
1, promotor preparation:
After polyvinyl alcohol and ethanol mixing, 35 ℃ add aqua ammonia (ammoniacal liquor) down, add sodium hydroxide and potassium hydroxide after 6 hours again, and 100 rotary speeds stir 3 hours formation promotors down;
The parts by weight of above-mentioned each component are following:
2, adopt dodecylbenzene and C
10Alpha-olefin, aluminum chloride and promotor alkylated reaction, the raw material weight umber is:
Dodecylbenzene: 5 parts
C
10Alhpa olefin: 50 parts
Aluminum chloride: 1.6 parts
Promotor: 0.7 part
Processing condition: earlier dodecylbenzene is pumped in the reactor, aluminum chloride and promotor is added again, agitator is full of nitrogen in the reactor again, nitrogen pressure 2～2.5Kg/cm
2, with pumping C
10Alpha-olefin slowly drips, 30 ℃ of temperature of reaction, 4 hours reaction times
3, sintetics is refining
Behind the alkylated reaction product is sent in the ion-exchanger refining.
The product pour point-39 that present embodiment obtains ℃, 282 ℃ of flash-points, 100 ℃ of kinematic viscosity 39.5, viscosity index 152.Record cut boiling Range Distribution Analysis: 350-500 ℃: 12%, greater than 500 ℃: 88%.
Embodiment 4
1, promotor preparation:
After polyvinyl alcohol and ethanol mixing, 35 ℃ add aqua ammonia (ammoniacal liquor) down, add sodium hydroxide and potassium hydroxide after 5 hours again, and 70 rotary speeds stir 2.5 hours formation promotors down;
The parts by weight of above-mentioned each component are following:
2, adopt dodecylbenzene and C
10Alpha-olefin, aluminum chloride and promotor alkylated reaction, the raw material weight umber is:
5 parts of dodecylbenzene: 250g
C
10105 parts of alhpa olefin: 5250g
3.3 parts of aluminum chloride: 165g
1.3 parts of promotor: 66g
Processing condition: earlier dodecylbenzene is pumped in the reactor, aluminum chloride and promotor is added again, agitator is full of nitrogen in the reactor again, nitrogen pressure 2～2.5Kg/cm
2, with pumping C
10Alpha-olefin slowly drips, 30 ℃ of temperature of reaction, 5 hours reaction times.
3, sintetics is refining
Behind the alkylated reaction product is sent in the ion-exchanger refining.
The product pour point-31 that present embodiment obtains ℃, 300 ℃ of flash-points, 100 ℃ of kinematic viscosity 105, viscosity index 185.Record the cut boiling Range Distribution Analysis: greater than 500 ℃: 100%.
Embodiment 5
1, adopts toluene and C
8Alpha-olefin, aluminum chloride and promotor (embodiment 1 is made) alkylated reaction, the raw material weight umber is:
Toluene: 4 parts
C
8Alhpa olefin: 41.6 parts
Aluminum chloride: 1.7 parts
Promotor: 0.7 part
Processing condition: earlier dodecylbenzene is pumped in the reactor, aluminum chloride and promotor is added again, agitator is full of nitrogen in the reactor again, nitrogen pressure 2～2.5Kg/cm
2, with pumping C
8Alhpa olefin slowly drips, 10 ℃ of temperature of reaction, 1 hour reaction times.
3, sintetics is refining
Behind the alkylated reaction product is sent in the ion-exchanger refining.
The product pour point-40 that present embodiment obtains ℃, 280 ℃ of flash-points, 100 ℃ of kinematic viscosity 41, viscosity index 148.
Embodiment 6
1, adopt the alkylbenzene (A1) that alkyl contains 200 carbon to mix, with C with the alkylbenzene (A2) that alkyl contains 260 carbon
14Alpha-olefin, aluminum chloride and promotor (embodiment 2 is made) alkylated reaction, the raw material weight umber is:
A1:2 part
A2:2 part
C
14Alhpa olefin: 47.6 parts
Aluminum chloride: 1.14 parts
Promotor: 0.45 part
Processing condition: earlier alkylbenzene is pumped in the reactor, aluminum chloride and promotor is added again, agitator is full of nitrogen in the reactor again, nitrogen pressure 2～2.5Kg/cm
2, with pumping C
14Alhpa olefin slowly drips, 30 ℃ of temperature of reaction, 4 hours reaction times.
3, sintetics is refining
Behind the alkylated reaction product is sent in the ion-exchanger refining.
The product pour point-25 that present embodiment obtains ℃, 295 ℃ of flash-points, 100 ℃ of kinematic viscosity 98.5, viscosity index 190.
Product in the foregoing description show that through nuclear-magnetism carbon spectrum hydrogen spectrum test observation product molecular weight distribution is balanced, and the aromatic hydrocarbons peak value shows obviously.
Above-mentioned instance shows that simultaneously the dosage of ratio and the aluminum chloride promotor of alkylbenzene and alpha-olefin should be an amount of synthetic hydrocarbon base oil that contains aromatic hydrocarbons that could obtain different model, all can not draw the qualified synthetic hydrocarbon oil that contains aromatic hydrocarbons if ratio and dosage are high with hanging down.
Claims (8)
1. one kind contains the preparation method that aromatic hydrocarbons synthesizes hydrocarbon, and it is characterized in that: with alkylbenzene and alpha-olefin is raw material, under the effect of aluminum trichloride catalyst and promotor, carries out alkylated reaction, obtains containing the synthetic hydrocarbon crude product of aromatic hydrocarbons; Said alkylbenzene is the alkylbenzene that alkyl contains 1 to 260 carbon atom, and said alpha-olefin is the alpha-olefin that contains 8 to 14 carbon atoms; The parts by weight of above-mentioned each component are:
Said promotor prepares process: after polyvinyl alcohol and ethanol mixing, add aqua ammonia, add sodium hydroxide and potassium hydroxide after 5～6 hours again, the basic complex that stirs back formation is promotor;
The parts by weight of above-mentioned each component are following:
2. according to the described preparation method of claim 1, it is characterized in that: said polyvinyl alcohol is a low molecular weight polyethylene alcohol, and molecular weight is 25000～35000.
3. according to the described preparation method of claim 1, it is characterized in that: said alkylated reaction carries out under nitrogen atmosphere; Nitrogen pressure 2～2.5kg/cm
2, 10～30 ℃ of temperature of reaction, 1～6 hour reaction times.
4. according to the described preparation method of claim 1, it is characterized in that: promotor prepares in the process, 30～40 ℃ of temperature of reaction, 2～3 hours reaction times.
5. according to the described preparation method of claim 1; It is characterized in that: gained behind the alkylated reaction is contained the synthetic hydrocarbon crude product of aromatic hydrocarbons send in the ion-exchanger refining; After removing catalyzer, auxiliary agent and the chlorion in the product through the ion exchange resin in the ion-exchanger, make and contain the synthetic hydrocarbon of aromatic hydrocarbons.
6. according to the described preparation method of claim 5, it is characterized in that: said ion exchange resin is feedstock production with the poly styrene sulfonate.
7. according to the described preparation method of claim 5, it is characterized in that: the prepared synthetic hydrocarbon of aromatic hydrocarbons that contains, aromatic hydrocarbons quality percentage composition is 5～10%.
8. according to the described preparation method of claim 5, it is characterized in that: the prepared synthetic hydrocarbon of aromatic hydrocarbons that contains, pour point-20～-50 ℃, 230～350 ℃ of flash-points, kinematic viscosity 15～120, viscosity index 120～200.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103289731A (en) * | 2012-02-28 | 2013-09-11 | 赵阳 | Method for preparing synthetic hydrocarbon containing aromatic hydrocarbon from internal olefin |
| CN103739422A (en) * | 2014-01-27 | 2014-04-23 | 锦州康泰润滑油添加剂股份有限公司 | Preparation method of dialkyl benzene |
| CN108795535A (en) * | 2018-06-29 | 2018-11-13 | 烟台智本知识产权运营管理有限公司 | A kind of preparation of arene-containing synthetic hydrocarbon base oil |
| CN108885197A (en) * | 2016-03-31 | 2018-11-23 | 埃克森美孚研究工程公司 | Screening hydrocarbon is to limit the composition and method that potential toxicology endangers |
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| CN103289731A (en) * | 2012-02-28 | 2013-09-11 | 赵阳 | Method for preparing synthetic hydrocarbon containing aromatic hydrocarbon from internal olefin |
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| CN108885197A (en) * | 2016-03-31 | 2018-11-23 | 埃克森美孚研究工程公司 | Screening hydrocarbon is to limit the composition and method that potential toxicology endangers |
| CN108795535A (en) * | 2018-06-29 | 2018-11-13 | 烟台智本知识产权运营管理有限公司 | A kind of preparation of arene-containing synthetic hydrocarbon base oil |
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