CN105536866B - Class ionic liquid and preparation method thereof and the application in preparing alkylate oil - Google Patents
Class ionic liquid and preparation method thereof and the application in preparing alkylate oil Download PDFInfo
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0285—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre also containing elements or functional groups covered by B01J31/0201 - B01J31/0274
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0279—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the cationic portion being acyclic or nitrogen being a substituent on a ring
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
- B01J31/0282—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aliphatic ring, e.g. morpholinium
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/56—Addition to acyclic hydrocarbons
- C07C2/58—Catalytic processes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
Abstract
The present invention provides type ionic liquid and preparation method thereof and the application in preparing alkylate oil.Amide compound is reacted with the first metallic compound and more than one second metallic compounds, class ionic liquid is made.Using such ionic liquid as catalyst, isoparaffin is alkylated with alkene and is reacted, detach class ionic liquid, alkylate oil is made.The class ionic liquid synthesis material of the present invention is easy to get, synthetic method is simple, cheap, and the alkylated reaction high selectivity using it as catalyst, C8 components and the octane number of trimethylpentane proportion and alkylate oil greatly improve.
Description
Technical field
The present invention relates to a type ionic liquids, more particularly to type ionic liquid and preparation method thereof and are preparing
Application in alkylate oil.
Background technology
As people are to the pay attention to day by day of environmental protection, quality of gasoline is to unleaded, low alkene and arene content, low steam
Pressure, hyposensitivity, high-octane rating direction are developed and are continuously improved.In this case, it is dimension that alkylate oil is called in into gasoline
Hold a kind of effective ways of gasoline high-octane rating, hyposensitivity and low-steam pressure.
Currently, catalyst used by industrial alkylation process is mainly the liquid strong acids such as the concentrated sulfuric acid, hydrofluoric acid.So
And hydrofluoric acid has severe toxicity and volatile formation aerosol, once leakage will cause seriously to production environment and surrounding ecological environment
Harm；It is big using the concentrated sulfuric acid as catalyst spent acid discharge capacity, and meeting severe corrosion equipment, subsequent processing difficulty are big.In environmental law
It advises under increasingly strict main trend, the advantage of alkylate oil is more prominent, and the defect of the traditional catalysts such as the concentrated sulfuric acid, hydrofluoric acid
Also it becomes increasingly conspicuous.Therefore, research and development a new generation is a problem to be solved efficiently with environmentally friendly catalyst for alkylation reaction.
Solid acid catalyst is as the novel alkylation catalyst having gradually developed in recent years, with the concentrated sulfuric acid, hydrofluoric acid
Etc. traditional catalysts compare, have many advantages, such as that volatility is low, corrosivity is low, pollution is small.However, solid acid catalyst centre of surface
Property and space steric effect, the temperature for making to be formed needed for carbonium ion is higher than traditional catalysts such as the concentrated sulfuric acid, hydrofluoric acid, and
The carbonium ion of isomery is not easy to generate and be stabilized；Also, carbonium ion is very easy further to react with alkene and is given birth to
At polyolefin, so as to cause a large amount of generations of polyolefins by-product.In addition, solid acid catalyst also have easy coking and deactivation,
It is catalyzed the defects of selecting response is poor.
Ionic liquid because have many advantages, such as corrosivity it is low, it is acid it is adjustable, easily detach with product, cyclic utilization rate it is high, make
It becomes the new catalyst of the traditional catalysts such as a kind of alternative hydrofluoric acid, the concentrated sulfuric acid.Notification number is the China of CN1203032
Patent discloses a kind of using compound ion liquid as the method for catalyst in preparing alkylated oil, the compound ion liquid catalyst
Cation source is in the hydrohalide of the amine containing alkyl or the hydrohalide of pyridine, and anion is two or more metal
Composite anion made from compound.C8 components and three in the alkylated oil prepared although with compound ion liquid catalysis
Methylpentane (TMP) proportion increases, however the synthesis of ionic liquid to synthesis ingredient requirement it is higher, synthetic method compared with
For complexity, and price is relatively expensive；In addition, it is limited with the selectivity of the ionic liquid-catalyzed alkylated reaction, and alkyl
It still needs further improvement for the octane number of dispersant.
Invention content
The present invention provides type ionic liquid and preparation method thereof and the application in preparing alkylate oil, with such from
The octane of the high selectivity of the alkylated reaction of sub- liquid catalyst, C8 components and trimethylpentane proportion and alkylate oil
Value greatly improves, and the synthesis material of such ionic liquid is more easy to get in addition, synthetic method is simple and cheap.
The present invention provides the preparation method of a type ionic liquid, by amide compound and the first metallic compound and one kind
Above second metallic compound is reacted.
In the present invention, the quantity of the second metallic compound is not limited strictly, such as can is a kind of to three kinds.And
And conventional method may be used and prepare the class ionic liquid.
In one embodiment, the preparation method of class ionic liquid includes the following steps：
Using hydrocarbon as solvent, under protective atmosphere, amide compound is added in the first metallic compound, is stirred at room temperature
After be warming up to 80-180 DEG C, continue stirring to complete reaction, detach hydrocarbon, obtain reactant；
Under protective atmosphere, be added more than one the second metallic compounds into above-mentioned reactant, keep it is temperature-resistant or
It is continuously heating to be no more than 180 DEG C, continues stirring to complete reaction, obtain class ionic liquid；
Wherein, the hydrocarbon be selected from the linear paraffin of carbon number 2-10, carbon number 2-10 branched paraffin and carbon number 6-12 aromatic hydrocarbons
In it is one or more.
Further, the hydrocarbon can be selected from pentane, normal hexane, normal heptane, normal octane, isopentane, isohexane, different heptan
One or more, for example, normal heptane of alkane, benzene,toluene,xylene, trimethylbenzene and mellitene；The protective atmosphere can be with nitrogen
Gas etc. is used as protective gas；It is described that be stirred at room temperature the time can be 15-60min；The continuation mixing time can be that 2-6 is small
When.
In another embodiment, the preparation method of class ionic liquid includes the following steps：
First metallic compound is uniformly mixed with more than one second metallic compounds, obtains metal mixture；
In dry air, amide compound is added in the metal mixture, 80- is warming up to after being stirred at room temperature
180 DEG C, continues stirring to complete reaction, obtain class ionic liquid.
Further, it can be 15-60min that the time, which is stirred at room temperature,；It can be 2-6 hours to continue mixing time.
In the present invention, the molar ratio of the amide compound and the first metallic compound can be 1：0.1 to 1：10, example
Such as 1：(1-2)；The molar ratio of first metallic compound and the second metallic compound can be 1:100 to 100:1, such as 1：
(0.05-0.55)。
Further, the amide compound can be selected from general formula R1CONR2R3Chain amide and general formula R1CONR2R3's
It is one or more in cyclic amide；General formula R1CONR2R3In, R1For hydrogen, the alkyl or-NR of carbon number 1-102R3, R2、R3Respectively solely
The vertical alkenyl selected from hydrogen, the alkyl of carbon number 1-10 or carbon number 1-10.
In the concrete scheme of the present invention, the amide compound is selected from urea, formamide, N-METHYLFORMAMIDE, N, N-
Dimethylformamide, acetamide, N- methylacetamides, DMAC N,N' dimethyl acetamide, acrylamide, 2-Pyrrolidone, N- methyl
It is one or more in pyrrolidones and 1,3- dimethyl-2-imidazolinones.
Further, first metallic compound be the first metal halide, sulfate or nitrate, described first
Metal is aluminium or gallium, such as aluminium；Second metallic compound be bimetallic halide, sulfate or nitrate, it is described
Second metal is copper, iron, zinc, nickel, cobalt, silver, molybdenum or platinum, such as copper, nickel or silver.The present invention to first metallic compound and
The valence state of metal does not limit strictly in second metallic compound, and the compound of multivalent state metal can be under its various valence state
Metallic compound, such as the halide of copper can be copper or cuprous halide etc..
The present invention concrete scheme in, first metallic compound be alchlor, alchlor, gallium trichloride or
Tribromide gallium；Second metallic compound is stannous chloride, copper chloride, copper nitrate, copper sulphate, silver chlorate, silver nitrate, sulfuric acid
Silver, nickel chloride or nickel nitrate.
The present invention also provides a type ionic liquids, are made according to any of the above-described preparation method.
The present invention also provides application of any of the above-described class ionic liquid in preparing alkylate oil.Specifically, should
Class ionic liquid is when preparing alkylate oil as catalyst application.
The present invention also provides a kind of methods preparing alkylate oil, using any of the above-described class ionic liquid as catalysis
Isoparaffin is alkylated with alkene and reacts by agent, detaches class ionic liquid, and alkylate oil is made.
Further, the isoparaffin is iso-butane；The alkene is selected from the linear alkene and carbon number 2- of carbon number 2-10
It is one or more in 10 branched-chain alkene.In the concrete scheme of the present invention, the alkene is selected from isobutene, 2- butylene, 1-
One or more, the especially isobutene and/or 2- butylene of butylene, propylene and amylene.
The present invention does not limit the reaction condition of the alkylated reaction strictly, can be the normal condition of this field；
For example, it is lower limit that the selection of reaction pressure, which can ensure that reaction raw materials keep liquid condition under alkylation reaction condition,.
Further, the molar ratio of the isoparaffin and alkene is 1:1 to 200:1, such as 10:1 to 100:1；It is described
The temperature of alkylated reaction is -20-100 DEG C, such as -10-25 DEG C；Absolute pressure can be 0.12-2.0MPa, such as 0.1-
1.6MPa；Reaction time can be 0.01-60min, such as 15-30min.
In the present invention, the alkylated reaction can carry out in the reactor；Wherein, used reactor can be
The conventional reactor of this field, such as the tank reactor with agitating device, tubular reactor, industrial sulfuric acid process or hydrofluoric acid
Continuous production device, other continuous reaction apparatus that method alkylated reaction uses etc..
The implementation of the present invention, at least has the advantage that：
1, class ionic liquid of the invention can be used as a kind of good ionic liquid substitute, not only possess and ionic liquid
Similar physicochemical characteristic, and synthesis material is more easy to get, synthetic method is simpler and price is relatively cheap；In addition, this
The class ionic liquid of invention has stronger water resistance and higher Lewis acid, has higher solubility to iso-butane, easily
It is detached with alkylate oil, the mode for restoring catalytic activity is simple.
2, to equipment almost without corrosivity, non-volatile, water sensibility reduces, is making class ionic liquid of the invention
For catalyst preparation alkylate oil when production operation it is easy, it is at low cost, not can cause environmental pollution, be good for the environment, be one
The alkylation process of kind green；In addition, such ionic liquid can fully improve the selection of trimethylpentane in C8 isoparaffins
Property, alkylation products have higher octane number, while the yield of alkylation products also improves a lot.
When 3, using the class ionic liquid of the present invention as catalyst preparation alkylate oil, the yield of alkylate oil can reach
The 170-180% of olefin feedstocks volume, C8 components proportion can reach 70-95% in alkylate oil, front three in C8 components
The ratio of base pentane can reach 70-93% or more, and RON (research octane number (RON)) can reach 93-103 in addition.
4, using the present invention class ionic liquid as the alkylate oil obtained by catalyst all isoparaffins of composition,
Alkene and aromatic hydrocarbons without macromolecular generate, and illustrate that the method for the present invention can inhibit the side reactions hair such as olefinic polymerization and cyclisation
It is raw；In particular, the class ionic liquid of the present invention can be used continuously 48 hours or more and catalytic activity does not subtract, the alkyl produced
The volume of carburetion can reach 150 times or more of class ionic-liquid catalyst volume, the service life length of class ionic liquid, consumption
It measures low, advantageously reduces production cost.
Specific implementation mode
To make the object, technical solutions and advantages of the present invention clearer, below in conjunction with the embodiment of the present invention, to this
Technical solution in inventive embodiments is clearly and completely described, it is clear that described embodiment is that a part of the invention is real
Example is applied, instead of all the embodiments.Based on the embodiments of the present invention, those of ordinary skill in the art are not making creation
Property labour under the premise of the every other embodiment that is obtained, shall fall within the protection scope of the present invention.
The preparation of embodiment one kind ionic liquid
Embodiment 1-1
The acetamide of 0.065 mole (3.84 grams) is slowly added to the AlCl of 0.1 mole (13.34 grams)3In, with normal heptane
Solvent is made, with nitrogen protection, stirs 30 minutes at ambient temperature, is then heated to 80 DEG C, continue stirring 2 hours, with
Make that the reaction was complete, obtains reaction mixture.Then, reaction mixture is cooled down, is divided into two-phase after cooling, be positive heptan at the middle and upper levels
Alkane, lower layer are reactant, and after detaching upper layer normal heptane, 0.015 mole (1.48 grams) are added into reactant under nitrogen protection
CuCl and be warming up to 120 DEG C, continue stirring 2 hours so that CuCl reacts completely, obtain class ionic liquid.
Embodiment 1-2
In dry air, solvent is made without normal heptane, by the CuCl of 0.015 mole (2.02 grams)2With 0.1 mole
The AlCl of (13.34 grams)3It is uniformly mixed, obtains metal mixture；Then, the acetamide of 0.065 mole (3.84 grams) is slow
It is added in above-mentioned metal mixture, is stirred at room temperature after mixing and is warming up to 120 DEG C and is reacted, reaction process heat release simultaneously forms palm fibre
Brown liquid controls reaction temperature at 120 DEG C, continues stirring 4 hours to complete the reaction, obtains class ionic liquid.
Embodiment 1-3
The acetamide of 0.065 mole (3.84 grams) is slowly added to the AlCl of 0.1 mole (13.34 grams)3In, with normal heptane
Solvent is made, with nitrogen protection, stirs 15 minutes at ambient temperature, is then heated to 80 DEG C, continue stirring 6 hours, with
Make that the reaction was complete, obtains reaction mixture.Then, reaction mixture is cooled down, is divided into two-phase after cooling, be positive heptan at the middle and upper levels
Alkane, lower layer are reactant, and after detaching upper layer normal heptane, 0.015 mole (1.48 grams) are added into reactant under nitrogen protection
CuCl and 0.015 mole (1.94 grams) NiCl2And 120 DEG C are warming up to, continue stirring 2 hours so that CuCl and NiCl2Completely
Reaction, obtains class ionic liquid.
Embodiment 1-4
The urea of 0.065 mole (3.90 grams) is slowly added to the AlCl of 0.1 mole (13.34 grams)3In, it is done with normal heptane
Solvent is stirred 60 minutes with nitrogen protection, is then heated to 80 DEG C at ambient temperature, continues stirring 4 hours, so that
The reaction was complete, obtains reaction mixture.Then, reaction mixture is cooled down, is divided into two-phase after cooling, be positive heptan at the middle and upper levels
Alkane, lower layer are reactant, and after detaching upper layer normal heptane, 0.015 mole (2.81 grams) are added into reactant under nitrogen protection
Cu (NO3)2And 120 DEG C are warming up to, continue stirring 2 hours so that Cu (NO3)2Reaction completely, obtains class ionic liquid.
Embodiment 1-5
In dry air, solvent is made without normal heptane, by the CuSO of 0.015 mole (2.39 grams)4With 0.1 mole
The AlCl of (13.34 grams)3It is uniformly mixed, obtains metal mixture；Then, the formamide of 0.065 mole (2.93 grams) is slow
It is added in above-mentioned metal mixture, is stirred at room temperature after mixing and is warming up to 120 DEG C and is reacted, reaction process heat release simultaneously forms palm fibre
Brown liquid controls reaction temperature at 120 DEG C, continues stirring 4 hours to complete the reaction, obtains class ionic liquid.
Embodiment 1-6
The N-METHYLFORMAMIDE of 0.065 mole (3.84 grams) is slowly added to the AlCl of 0.1 mole (13.34 grams)3In, with
Normal heptane is cooked solvent, with nitrogen protection, is stirred 30 minutes at ambient temperature, is then heated to 80 DEG C, it is small to continue stirring 2
When, to complete the reaction, obtain reaction mixture.Then, reaction mixture is cooled down, is divided into two-phase after cooling, at the middle and upper levels
For normal heptane, lower layer is reactant, after detaching upper layer normal heptane, is added 0.015 mole into reactant under nitrogen protection
The AgNO of (2.54 grams)3And 120 DEG C are warming up to, continue stirring 2 hours so that AgNO3Reaction completely, obtains class ionic liquid.
Embodiment 1-7
In dry air, solvent is made without normal heptane, by the Ag of 0.015 mole (4.68 grams)2SO4With 0.1 mole
The AlCl of (13.34 grams)3It is uniformly mixed, obtains metal mixture；Then, by the N of 0.065 mole (4.75 grams), N- dimethyl
Formamide is slowly added into above-mentioned metal mixture, is stirred at room temperature after mixing and is warming up to 120 DEG C and is reacted, reaction process is put
Heat simultaneously forms brown liquid, and reaction temperature is controlled at 120 DEG C, continues stirring 4 hours to complete the reaction, obtains class ionic liquid
Body.
Embodiment 1-8
The acetamide of 0.075 mole (4.43 grams) is slowly added to the AlCl of 0.1 mole (13.34 grams)3In, with normal heptane
Solvent is made, with nitrogen protection, stirs 30 minutes at ambient temperature, is then heated to 80 DEG C, continue stirring 2 hours, with
Make that the reaction was complete, obtains reaction mixture.Then, reaction mixture is cooled down, is divided into two-phase after cooling, be positive heptan at the middle and upper levels
Alkane, lower layer are reactant, and after detaching upper layer normal heptane, 0.025 mole (4.21 grams) are added into reactant under nitrogen protection
Ni (NO3)2And 120 DEG C are warming up to, continue stirring 2 hours so that Ni (NO3)2Reaction completely, obtains class ionic liquid.
Embodiment 1-9
In dry air, solvent is made without normal heptane, by the NiSO of 0.005 mole (0.67 gram)4With 0.1 mole
The AlCl of (13.34 grams)3It is uniformly mixed, obtains metal mixture；Then, by the N- methyl vinyls of 0.085 mole (6.21 grams)
Amine is slowly added into above-mentioned metal mixture, is stirred at room temperature after mixing and is warming up to 80 DEG C and is reacted, reaction process heat release is simultaneously
Brown liquid is formed, reaction temperature is controlled at 80 DEG C, continues stirring 6 hours to complete the reaction, obtains class ionic liquid.
Embodiment 1-10
The DMAC N,N' dimethyl acetamide of 0.095 mole (8.72 grams) is slowly added to the AlCl of 0.1 mole (13.34 grams)3
In, solvent is done with normal heptane, with nitrogen protection, stirs 30 minutes at ambient temperature, is then heated to 80 DEG C, continues to stir
It mixes 2 hours, to complete the reaction, obtains reaction mixture.Then, reaction mixture is cooled down, is divided into two-phase after cooling, wherein
Upper layer is normal heptane, and lower layer is reactant, after detaching upper layer normal heptane, 0.035 is added into reactant under nitrogen protection and rubs
The CuCl of your (4.71 grams)2And 140 DEG C are warming up to, continue stirring 2 hours so that CuCl2Reaction completely, obtains class ionic liquid.
Embodiment 1-11
In dry air, solvent is made without normal heptane, by the CuSO of 0.045 mole (7.17 grams)4With 0.1 mole
The AlCl of (13.34 grams)3It is uniformly mixed, obtains metal mixture；Then, by the N- methylpyrroles of 0.100 mole (9.91 grams)
Alkanone is slowly added into above-mentioned metal mixture, is stirred at room temperature after mixing and is warming up to 180 DEG C and is reacted, reaction process heat release
And brown liquid is formed, reaction temperature is controlled at 180 DEG C, continues stirring 2 hours to complete the reaction, obtains class ionic liquid
Body.
Embodiment 1-12
The 2-Pyrrolidone of 0.050 mole (4.25 grams) is slowly added to the AlCl of 0.1 mole (13.34 grams)3In, with just
Heptane makees solvent, with nitrogen protection, stirs 30 minutes at ambient temperature, is then heated to 80 DEG C, it is small to continue stirring 2
When, to complete the reaction, obtain reaction mixture.Then, reaction mixture is cooled down, is divided into two-phase after cooling, at the middle and upper levels
For normal heptane, lower layer is reactant, after detaching upper layer normal heptane, is added 0.055 mole into reactant under the protection of nitrogen
The CuCl of (7.41 grams)2And 120 DEG C are warming up to, continue stirring 2 hours so that CuCl2Reaction completely, obtains class ionic liquid.
The preparation of embodiment dialkyl group carburetion
Embodiment 2-1
The class ionic liquid 200ml prepared in above-described embodiment 1-1 is added in the reaction kettle with stirring, with nitrogen pressurising
It to 0.5MPa, is vigorously stirred, squeezes into the mixed raw material 1200ml of iso-butane and 2- butylene using high-pressure pump, isobutyl in mixed raw material
The molar ratio (i.e. alkane alkene ratio) of alkane and 2- butylene is 10:1, alkylated reaction 20 minutes at 10 DEG C.It detaches after reaction not
The iso-butane of reaction, and reaction product is placed in separatory funnel and is stood, reaction product is divided into two layers, and wherein lower layer is class ion
Liquid, upper layer are alkylate oil.After detaching lower layer's class ionic liquid, alkylate oil is obtained.
The component of abovementioned alkyl carburetion is detected using chromatography, detects the research octane number (RON) of alkylate oil in addition
RON, testing result are shown in Table 1.
Embodiment 2-2
The class ionic liquid 200m1 prepared in above-described embodiment 1-1 is added in the reaction kettle with stirring, with nitrogen pressurising
It to 0.5MPa, is vigorously stirred, the mixed raw material 1200ml of iso-butane and 1- butylene, mixed raw material iso-butane is squeezed into using high-pressure pump
Molar ratio with 1- butylene is 20:1, alkylated reaction 20 minutes at 0 DEG C.Unreacted iso-butane is detached after reaction,
And reaction product is placed in separatory funnel and is stood, reaction product is divided into two layers, and wherein lower layer is class ionic liquid, and upper layer is alkane
Base carburetion.After detaching lower layer's class ionic liquid, alkylate oil is obtained.
The component of abovementioned alkyl carburetion is detected using chromatography, detects the research octane number (RON) of alkylate oil in addition
RON, testing result are shown in Table 1.
Embodiment 2-3
The class ionic liquid 200ml prepared in above-described embodiment 1-2 is added in the reaction kettle with stirring, with nitrogen pressurising
It to 0.8MPa, is vigorously stirred, squeezes into the mixed raw material 800ml of iso-butane and isobutene using high-pressure pump, isobutyl in mixed raw material
The molar ratio of alkane and isobutene is 20:1, alkylated reaction 20 minutes at 25 DEG C.Unreacted isobutyl is detached after reaction
Alkane, and reaction product is placed in separatory funnel and is stood, reaction product is divided into two layers, and wherein lower layer is class ionic liquid, upper layer
For alkylate oil.After detaching lower layer's class ionic liquid, alkylate oil is obtained.
The component of abovementioned alkyl carburetion is detected using chromatography, detects the research octane number (RON) of alkylate oil in addition
RON, testing result are shown in Table 1.
Embodiment 2-4
The class ionic liquid 200ml prepared in above-described embodiment 1-3 is added in the reaction kettle with stirring, with nitrogen pressurising
It to 1.5MPa, is vigorously stirred, squeezes into the mixed raw material 600ml of iso-butane and 2- butylene using high-pressure pump, isobutyl in mixed raw material
The molar ratio of alkane and 2- butylene is 20:1, alkylated reaction 15 minutes at 10 DEG C.Unreacted isobutyl is detached after reaction
Alkane, and reaction product is placed in separatory funnel and is stood, reaction product is divided into two layers, and wherein lower layer is class ionic liquid, upper layer
For alkylate oil.After detaching lower layer's class ionic liquid, alkylate oil is obtained.
The component of abovementioned alkyl carburetion is detected using chromatography, detects the research octane number (RON) of alkylate oil in addition
RON, testing result are shown in Table 1.
Embodiment 2-5
The class ionic liquid 200ml prepared in above-described embodiment 1-4 is added in the reaction kettle with stirring, with nitrogen pressurising
It to 1.0MPa, is vigorously stirred, squeezes into the mixed raw material 400ml of iso-butane and 1- butylene using high-pressure pump, isobutyl in mixed raw material
The molar ratio of alkane and 1- butylene is 30:1, it is reacted 15 minutes at 15 DEG C.Unreacted iso-butane is detached after reaction, and will
Reaction product is placed in separatory funnel and stands, and reaction product is divided into two layers, and wherein lower layer is class ionic liquid, and upper layer is alkylation
Oil.After detaching lower layer's class ionic liquid, alkylate oil is obtained.
The component of abovementioned alkyl carburetion is detected using chromatography, detects the research octane number (RON) of alkylate oil in addition
RON, testing result are shown in Table 1.
Embodiment 2-6
The class ionic liquid 200ml prepared in above-described embodiment 1-5 is added in the reaction kettle with stirring, with nitrogen pressurising
It to 0.1MPa, is vigorously stirred, squeezes into the mixed raw material 1200ml of iso-butane and isobutene using high-pressure pump, isobutyl in mixed raw material
The molar ratio of alkane and isobutene is 10:1, alkylated reaction 30 minutes at -10 DEG C.Unreacted isobutyl is detached after reaction
Alkane, and reaction product is placed in separatory funnel and is stood, reaction product is divided into two layers, and wherein lower layer is class ionic liquid, upper layer
For alkylate oil.After detaching lower layer's class ionic liquid, alkylate oil is obtained.
The component of abovementioned alkyl carburetion is detected using chromatography, detects the research octane number (RON) of alkylate oil in addition
RON, testing result are shown in Table 1.
Embodiment 2-7
The class ionic liquid 200ml prepared in above-described embodiment 1-6 is added in the reaction kettle with stirring, with nitrogen pressurising
It to 0.1MPa, is vigorously stirred, squeezes into the mixed raw material 1200ml of iso-butane and propylene using high-pressure pump, iso-butane in mixed raw material
With propylene than molar ratio be 10:1, alkylated reaction 30 minutes at -10 DEG C.Unreacted isobutyl is detached after reaction
Alkane, and reaction product is placed in separatory funnel and is stood, reaction product is divided into two layers, and wherein lower layer is class ionic liquid, upper layer
For alkylate oil.After detaching lower layer's class ionic liquid, alkylate oil is obtained.
The component of abovementioned alkyl carburetion is detected using chromatography, detects the research octane number (RON) of alkylate oil in addition
RON, testing result are shown in Table 1.
Embodiment 2-8
The class ionic liquid 200ml prepared in above-described embodiment 1-7 is added in the reaction kettle with stirring, with nitrogen pressurising
It to 0.1MPa, is vigorously stirred, squeezes into the mixed raw material 1200ml of iso-butane and amylene using high-pressure pump, iso-butane in mixed raw material
Molar ratio with amylene is 10:1, alkylated reaction 30 minutes at -10 DEG C.Unreacted iso-butane is detached after reaction,
And reaction product is placed in separatory funnel and is stood, reaction product is divided into two layers, and wherein lower layer is class ionic liquid, and upper layer is alkane
Base carburetion.After detaching lower layer's class ionic liquid, alkylate oil is obtained.
The component of abovementioned alkyl carburetion is detected using chromatography, detects the research octane number (RON) of alkylate oil in addition
RON, testing result are shown in Table 1.
Embodiment 2-9
The class ionic liquid 200ml prepared in above-described embodiment 1-1 is added in the reaction kettle with stirring, with nitrogen pressurising
It to 0.5MPa, is vigorously stirred, the mixed raw material 1200ml of iso-butane, propylene, amylene and isobutene is squeezed into using high-pressure pump, mix
Molar ratio in raw material between iso-butane, propylene, amylene and isobutene is 45：1：1：1, alkylated reaction 20 minutes at 0 DEG C.
Unreacted iso-butane is detached after reaction, and reaction product is placed in separatory funnel and is stood, reaction product is divided into two layers,
Wherein lower layer is class ionic liquid, and upper layer is alkylate oil.After detaching lower layer's class ionic liquid, alkylate oil is obtained.
The component of abovementioned alkyl carburetion is detected using chromatography, detects the research octane number (RON) of alkylate oil in addition
RON, testing result are shown in Table 1.
Embodiment 2-10
The class ionic liquid 200ml prepared in above-described embodiment 1-5 is added in the reaction kettle with stirring, with nitrogen pressurising
It to 0.1MPa, is vigorously stirred, the mixed raw material 1500ml of iso-butane, 2- butylene and 1- butylene is squeezed into using high-pressure pump, mixing is former
Molar ratio in material between iso-butane, 2- butylene and 1- butylene is 30：1：1, alkylated reaction 30 minutes at -10 DEG C.Reaction
After detach unreacted iso-butane, and reaction product is placed in separatory funnel and is stood, reaction product is divided into two layers, wherein
Lower layer is class ionic liquid, and upper layer is alkylate oil.After detaching lower layer's class ionic liquid, alkylate oil is obtained.
The component of abovementioned alkyl carburetion is detected using chromatography, detects the research octane number (RON) of alkylate oil in addition
RON, testing result are shown in Table 1.
Embodiment 2-11
The class ionic liquid 200ml prepared in above-described embodiment 1-1 is added in the reaction kettle with stirring, with nitrogen pressurising
It to 1.6MPa, is vigorously stirred, the mixed raw material 1200ml of iso-butane, 2- butylene, 1- butylene and isobutene is squeezed into using high-pressure pump,
Molar ratio in mixed raw material between iso-butane, 2- butylene, 1- butylene and isobutene is 45：1：1：1, it is alkylated at -5 DEG C anti-
It answers 20 minutes.Unreacted iso-butane is detached after reaction, and reaction product is placed in separatory funnel and is stood, reaction product
It is divided into two layers, wherein lower layer is class ionic liquid, and upper layer is alkylate oil.After detaching lower layer's class ionic liquid, it is alkylated
Oil.
The component of abovementioned alkyl carburetion is detected using chromatography, detects the research octane number (RON) of alkylate oil in addition
RON, testing result are shown in Table 1.
Embodiment 2-12
The class ionic liquid 200ml prepared in above-described embodiment 1-1 is added in the reaction kettle with stirring, with nitrogen pressurising
It to 1.0MPa, is vigorously stirred, squeezes into the mixed raw material 1200ml of iso-butane and 1- butylene using high-pressure pump, isobutyl in mixed raw material
The molar ratio of alkane and 1- butylene is 100:1, alkylated reaction 20 minutes at 10 DEG C.Unreacted isobutyl is detached after reaction
Alkane, and reaction product is placed in separatory funnel and is stood, reaction product is divided into two layers, and wherein lower layer is class ionic liquid, upper layer
For alkylate oil.After detaching lower layer's class ionic liquid, alkylate oil is obtained.
The component of abovementioned alkyl carburetion is detected using chromatography, detects the research octane number (RON) of alkylate oil in addition
RON, testing result are shown in Table 1.
Embodiment 2-13
The class ionic liquid 200ml prepared in above-described embodiment 1-8 is added in the reaction kettle with stirring, with nitrogen pressurising
It to 0.5MPa, is vigorously stirred, squeezes into the mixed raw material 1200ml of iso-butane and 2- butylene using high-pressure pump, isobutyl in mixed raw material
The molar ratio of alkane and 2- butylene is 10:1, alkylated reaction 20 minutes at 10 DEG C.Unreacted isobutyl is detached after reaction
Alkane, and reaction product is placed in separatory funnel and is stood, reaction product is divided into two layers, and wherein lower layer is class ionic liquid, upper layer
For alkylate oil.After detaching lower layer's class ionic liquid, alkylate oil is obtained.
The component of abovementioned alkyl carburetion is detected using chromatography, detects the research octane number (RON) of alkylate oil in addition
RON, testing result are shown in Table 1.
Embodiment 2-14
The class ionic liquid 200ml prepared in above-described embodiment 1-9 is added in the reaction kettle with stirring, with nitrogen pressurising
It to 0.5MPa, is vigorously stirred, squeezes into the mixed raw material 1200ml of iso-butane and 2- butylene using high-pressure pump, isobutyl in mixed raw material
The molar ratio of alkane and 2- butylene is 10:1, alkylated reaction 20 minutes at 10 DEG C.Unreacted isobutyl is detached after reaction
Alkane, and reaction product is placed in separatory funnel and is stood, reaction product is divided into two layers, and wherein lower layer is class ionic liquid, upper layer
For alkylate oil.After detaching lower layer's class ionic liquid, alkylate oil is obtained.
The component of abovementioned alkyl carburetion is detected using chromatography, detects the research octane number (RON) of alkylate oil in addition
RON, testing result are shown in Table 1.
Embodiment 2-15
The class ionic liquid 200ml prepared in above-described embodiment 1-10 is added in the reaction kettle with stirring, is filled with nitrogen
It is depressed into 0.5MPa, is vigorously stirred, squeezes into the mixed raw material 1200ml of iso-butane and 2- butylene using high-pressure pump, it is different in mixed raw material
The molar ratio of butane and 2- butylene is 10:1, alkylated reaction 20 minutes at 10 DEG C.It detaches after reaction unreacted different
Butane, and reaction product is placed in separatory funnel and is stood, reaction product is divided into two layers, and wherein lower layer is class ionic liquid, on
Layer is alkylate oil.After detaching lower layer's class ionic liquid, alkylate oil is obtained.
The component of abovementioned alkyl carburetion is detected using chromatography, detects the research octane number (RON) of alkylate oil in addition
RON, testing result are shown in Table 1.
Embodiment 2-16
The class ionic liquid 200ml prepared in above-described embodiment 1-11 is added in the reaction kettle with stirring, is filled with nitrogen
It is depressed into 0.5MPa, is vigorously stirred, squeezes into the mixed raw material 1200ml of iso-butane and 2- butylene using high-pressure pump, it is different in mixed raw material
The molar ratio of butane and 2- butylene is 10:1, alkylated reaction 20 minutes at 10 DEG C.It detaches after reaction unreacted different
Butane, and reaction product is placed in separatory funnel and is stood, reaction product is divided into two layers, and wherein lower layer is class ionic liquid, on
Layer is alkylate oil.After detaching lower layer's class ionic liquid, alkylate oil is obtained.
The component of abovementioned alkyl carburetion is detected using chromatography, detects the research octane number (RON) of alkylate oil in addition
RON, testing result are shown in Table 1.
Embodiment 2-17
The class ionic liquid 200ml prepared in above-described embodiment 1-12 is added in the reaction kettle with stirring, is filled with nitrogen
It is depressed into 0.5MPa, is vigorously stirred, squeezes into the mixed raw material 1200ml of iso-butane and 2- butylene using high-pressure pump, it is different in mixed raw material
The molar ratio of butane and 2- butylene is 10:1, alkylated reaction 20 minutes at 10 DEG C.It detaches after reaction unreacted different
Butane, and reaction product is placed in separatory funnel and is stood, reaction product is divided into two layers, and wherein lower layer is class ionic liquid, on
Layer is alkylate oil.After detaching lower layer's class ionic liquid, alkylate oil is obtained.
The component of abovementioned alkyl carburetion is detected using chromatography, detects the research octane number (RON) of alkylate oil in addition
RON, testing result are shown in Table 1.
The continuous preparation of embodiment trialkyl carburetion
The class ionic liquid 200ml prepared in above-described embodiment 1-1 is added in the reaction kettle with stirring, with nitrogen pressurising
It to 0.5MPa, is vigorously stirred, squeezes into the mixed raw material of iso-butane and 2- butylene using high-pressure pump, iso-butane and 2- in mixed raw material
The molar ratio of butylene is 10:1, reaction, wherein reaction mass continuous sample introduction are alkylated at 10 DEG C, continuously discharge is anti-for product
Kettle is answered, measures the composition of olefin(e) centent and alkylate oil in tail gas per hour.
The result shows that：
1, C4 alkene is not detected in successive reaction 48 hours in tail gas, illustrate that alkene is totally converted, and the alkyl produced
The volume of carburetion reaches 150 times or so of class ionic-liquid catalyst volume.
2, during 48 hours, the composition of alkylate oil does not change successive reaction, all isoparaffins of composition,
There is no the alkene of macromolecular and aromatic hydrocarbons to generate, illustrate the class ionic-liquid catalyst of the present invention can effectively inhibit olefinic polymerization and
The side reactions such as cyclisation occur.
3, in alkylate oil, the volumn concentration of C8 components is the volume basis of trimethylpentane in 96%, C8 components
Content is 92%, and research octane number (RON) RON reaches 103；Illustrate anti-using class ionic liquid of the present invention as the alkylation of catalyst
High selectivity, C8 components and the octane number of trimethylpentane proportion and alkylate oil is answered to greatly improve.
Reference examples 1
The acetamide of 0.065 mole (3.84 grams) is slowly added to the AlCl of 0.1 mole (13.34 grams)3In, with normal heptane
Solvent is made, with nitrogen protection, stirs 30 minutes at ambient temperature, is then heated to 80 DEG C, continue stirring 2 hours, with
Make that the reaction was complete, obtains reaction mixture.Then, reaction mixture is cooled down, is divided into two-phase after cooling, be positive heptan at the middle and upper levels
Alkane, lower layer are class ionic liquid, containing only a kind of metallic compound in such ionic liquid.
The class ionic liquid 200ml of above-mentioned preparation is added in the reaction kettle with stirring, 0.5MPa is pressurized to nitrogen, it is acute
Strong stirring, squeezes into the mixed raw material 1200ml of iso-butane and 2- butylene using high-pressure pump, iso-butane and 2- butylene in mixed raw material
Molar ratio be 10:1, alkylated reaction 20 minutes at 10 DEG C.Unreacted iso-butane is detached after reaction, and will reaction
Product is placed in separatory funnel and stands, and reaction product is divided into two layers, and wherein lower layer is class ionic liquid, and upper layer is alkylate oil.
After detaching lower layer's class ionic liquid, alkylate oil is obtained.
The component of abovementioned alkyl carburetion is detected using chromatography, detects the research octane number (RON) of alkylate oil in addition
RON, testing result are shown in Table 1.
The testing result of 1 alkylate oil of table
Mark：The conversion ratio of alkene is the of poor quality and ratio for the quality for reacting preceding alkene of the front and back alkene of reaction.
Reference examples 2
By the AlCl of 0.56 mole (74.98 grams)3It is slowly added in the hydrochloric acid triethyl ammonium of 0.282 mole (39.76 grams),
Solvent, nitrogen protection are done with normal heptane, stirs 30 minutes at ambient temperature, is then heated to 80 DEG C, it is small to continue stirring 2
When, to complete the reaction.Reactant is divided into two-phase after cooling, and upper layer is heptane, and lower layer is that composition is [NEt3H+][Al2Cl7 -]
Ionic liquid.Under the protection of nitrogen, to synthetic [NEt3H+][Al2Cl7 -] 0.056 mole (5.54 is added in ionic liquid
Gram) CuCl, and be warming up to 100 DEG C, stirring obtains ionic liquid until CuCl reacts completely.
The ionic liquid 200ml of above-mentioned preparation is added in the autoclave with stirring, is pressurized to 0.5MPa with nitrogen, acutely
The mixed raw material of iso-butane and 2- butylene is squeezed into stirring using high-pressure pump, and alkane alkene ratio is 10 in raw material：1, alkane is carried out at 10 DEG C
Glycosylation reaction；Wherein, olefin feed continuous sample introduction is reacted, reaction kettle is continuously discharged in product, measures alkene in tail gas per hour and contains
The composition of amount and alkylate oil.
The result shows that：In 48 hours tandem reaction sequences, C8 components account for trimethylpentane in 70%, C8 components and account for
74%, research octane number (RON) RON are 93, and the volume of the alkylate oil of production reaches 25 times of left sides of class ionic-liquid catalyst volume
It is right.
Finally it should be noted that：The above embodiments are only used to illustrate the technical solution of the present invention., rather than its limitations；To the greatest extent
Present invention has been described in detail with reference to the aforementioned embodiments for pipe, it will be understood by those of ordinary skill in the art that：Its according to
So can with technical scheme described in the above embodiments is modified, either to which part or all technical features into
Row equivalent replacement；And these modifications or replacements, various embodiments of the present invention technology that it does not separate the essence of the corresponding technical solution
The range of scheme.
Claims (5)
1. the preparation method of a type ionic liquid, which is characterized in that by amide compound and the first metallic compound and one kind
Above second metallic compound is reacted；
Include the following steps：
Using hydrocarbon as solvent, under protective atmosphere, amide compound is added in the first metallic compound, is risen after being stirred at room temperature
Temperature continues stirring to complete reaction, detaches hydrocarbon, obtain reactant to 80-180 DEG C；
Under protective atmosphere, more than one the second metallic compounds are added into above-mentioned reactant, keep temperature-resistant or continue
It is warming up to and is no more than 180 DEG C, continue stirring to complete reaction, obtain class ionic liquid；
Wherein, in linear paraffin, the branched paraffin of carbon number 2-10 and the aromatic hydrocarbons of carbon number 6-12 of the hydrocarbon selected from carbon number 2-10
It is one or more；
The amide compound is selected from general formula R1CONR2R3Chain amide and general formula R1CONR2R3Cyclic amide in one kind
Or it is a variety of；General formula R1CONR2R3In, R1For hydrogen, the alkyl or-NR of carbon number 1-102R3, R2、R3It is each independently selected from hydrogen, carbon number 1-
10 alkyl or the alkenyl of carbon number 1-10；
First metallic compound is halide, sulfate or the nitrate of the first metal, and first metal is aluminium or gallium；
Second metallic compound be bimetallic halide, sulfate or nitrate, second metal be copper, iron, zinc,
Nickel, cobalt, silver, molybdenum or platinum；
The molar ratio of the amide compound and the first metallic compound is 1：0.1 to 1：10, first metallic compound with
The molar ratio of second metallic compound is 1：100 to 100：1.
2. a type ionic liquid, which is characterized in that preparation method described in accordance with the claim 1 is made.
3. a kind of method preparing alkylate oil, which is characterized in that using the class ionic liquid described in claim 2 as catalysis
Isoparaffin is alkylated with alkene and reacts by agent, detaches class ionic liquid, and alkylate oil is made.
4. according to the method described in claim 3, it is characterized in that, the isoparaffin is iso-butane, the alkene is carbon number
The linear alkene of 2-10 or the branched-chain alkene of carbon number 2-10.
5. method according to claim 3 or 4, which is characterized in that the molar ratio of the isoparaffin and alkene is 1：1 to
200：1, the temperature of the alkylated reaction is -20-100 DEG C, absolute pressure 0.12-2.0MPa, reaction time 0.01-
60min。
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| CN112403515B (en) * | 2020-12-04 | 2022-09-02 | 江苏棋成化工有限公司 | Asymmetric bimetal dication ionic liquid catalyst, preparation method and application thereof |
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| CN113336614B (en) * | 2021-05-31 | 2023-03-14 | 中国石油大学(北京) | Preparation method of alkylbenzene based on catalysis of ionic liquid |
| CN114014775A (en) * | 2021-11-26 | 2022-02-08 | 华东理工大学 | Functionalized surface active ionic liquid and preparation method and application thereof |
| CN115181585B (en) * | 2022-08-09 | 2023-11-07 | 中国石油大学(北京) | Alkane isomerization method based on ionic liquid catalysis |
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