CN106731489A - A kind of method of use fluoride ion liquid high-temperature digestion hydrocarbon gas - Google Patents
A kind of method of use fluoride ion liquid high-temperature digestion hydrocarbon gas Download PDFInfo
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- CN106731489A CN106731489A CN201510828349.9A CN201510828349A CN106731489A CN 106731489 A CN106731489 A CN 106731489A CN 201510828349 A CN201510828349 A CN 201510828349A CN 106731489 A CN106731489 A CN 106731489A
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1493—Selection of liquid materials for use as absorbents
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1487—Removing organic compounds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/30—Ionic liquids and zwitter-ions
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/70—Organic compounds not provided for in groups B01D2257/00 - B01D2257/602
- B01D2257/702—Hydrocarbons
- B01D2257/7022—Aliphatic hydrocarbons
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/70—Organic compounds not provided for in groups B01D2257/00 - B01D2257/602
- B01D2257/702—Hydrocarbons
- B01D2257/7022—Aliphatic hydrocarbons
- B01D2257/7025—Methane
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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
- Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
- Y02C20/00—Capture or disposal of greenhouse gases
- Y02C20/20—Capture or disposal of greenhouse gases of methane
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Abstract
The present invention provides a kind of method of use fluoride ion liquid high-temperature digestion hydrocarbon gas, belongs to chemical industry dissolving technology field.The method course of dissolution is operated using high-pressure installation, add ionic liquid, it is filled with gas to be dissolved, the high-temperature digestion of hydrocarbon gas is realized, fluoride ion liquid can be for kation alkyl fluorine richness ionic liquid, anionic alkyl group fluorine richness ionic liquid or zwitterion while alkyl fluoride modified ionic liquid；The fluoride ion liquid physical chemistry is stable in properties, prepares simply, can be used for hydrocarbon dissolving transformation system, compared to the solute effect that aqueous phase system improves 40 times, moreover it can be used to the storage transport of hydrocarbon gas.
Description
Technical field
The invention belongs to chemical industry dissolving technology field, and in particular to one kind uses fluoride ion liquid high-temperature digestion
The method of hydrocarbon gas.
Background technology
Hydrocarbon is main energy sources composition, and the activation of c h bond and product conversion enjoy favor always.With
Last decade, substantial amounts of shale gas are verified and exploited, the hydrocarbon such as methane therein and ethane it is molten
Solve and be converted into the task of top priority.
By taking methane as an example, the conversion of methane mainly has two kinds of heterogeneous conversion and equal inversion of phases.At heterogeneous turn
In change, Dalian Chemistry and Physics Institute teacher Bao Xinhe is mentioned in methane directly non-oxide conversion, it is possible to achieve methane is arrived
The Efficient Conversion of ethene and aromatic hydrocarbons, but temperature is extremely harsh, to 1173K.Remaining heterogeneous conversion
Selectivity is all extremely undesirable.The selectivity of methane then can be strictly controlled to reach more than 90% in equal inversion of phases.
But in equal inversion of phases, general water is solvent, and the solubility of water beetle alkane is low, and methane is caused to a certain extent
Conversion ratio it is undesirable.
Ionic liquid has water and the unexistent special nature of OOS such as：Almost without vapour pressure,
It is non-combustible, physicochemical properties stabilization etc..It is widely used for oxidation reaction, hydrogenation reaction, isomerization
Etc. substituting organic solvent in various reactions.Ionic liquid for hydrocarbon gas conversion mainly has
[Bmim][Cl],[Bmim][HSO4] etc., its dissolubility to hydrocarbon gas is extremely low, all the time as system
About factor.
At present, research of the hydrocarbon in ionic liquid focuses primarily upon the absorption and separation from hydrocarbon
Carbon dioxide, hydrogen sulfide is with remaining sulfide.Dissolution studies for hydrocarbons such as methane are less；Slowly
Bright grade has invented a kind of method that utilization ionic liquid purifies mine mash gas extraction forever, is symmetrical using cation
The phosphine ionic liquid of structure or side-chain structure long, anion is NTf2, purifying first is collected by absorbing repeatedly
Alkane, solution temperature is narrow, only 18 DEG C~25 DEG C；John M.Prausnitz in 2013 publish an article proposition
[P (14) 666] [TMPP], [P4444] [TMPP], [P8111] [TMPP] has good suction to hydrocarbon gas
Produce effects really, its solution temperature is 26~80 DEG C.The research of the dissolving of hydrocarbon has been achieved with progress, but
It is that one side cation long-chain or multichained construction phosphine ionic liquid building-up process are sufficiently complex, on the other hand contains
The ionic liquid of C-H can be destroyed in the C-H of catalyst system and catalyzing intermediate ion liquid itself, be not suitable for reaction system
In serve as solvent.The ionic liquid being modified containing fluorine richness or perfluor proposed by the present invention, not only viscosity is low molten
Xie Gao, excellent in stability, the absorption of hydrocarbon gas can be promoted, and eliminate reaction system
The destruction of ionic liquid is a kind of very good high-temperature digestion and converts the solvent of gaseous state nytron.
It is good that Fabrice Mutelet in 2014 once referred to that cation or anion containing fluoroalkyl had
The effect of good absorption methane.But this article data is unreliable.First, its calculating process uses reason
Think equation of gas state PV=nRT, this equation should be corrected in actual gas using compressibility factor etc..
Second, methane dissolves variation with temperature in ionic liquid and very much not tallies with the actual situation very much.With [Emim] [NTf2]
As a example by, in the research of Fabrice Mutelet, temperature from 26~39 DEG C when, its KHIncrease from 25.8MPa
To 125.9MPa.And in the result of Hohn M.Prausnitz during 30~60 DEG C of temperature, KHFor 52.2MPa~
59.2MPa.There is the gas of Alexia Finotello in 2008 to dissolve temperature 0~70 in selective etc. result again
DEG C when, KHFor between 53MPa~58MPa, same its solute effect is with temperature in my experimental result
Change is not obvious.3rd, its result shows at 44 DEG C, [C2‐OHmim][PF6] solute effect is better than
[C2‐mim][NTf2], this result and its conclusion for drawing are disagreed.
The content of the invention
It is an object of the invention to provide a kind of method of fluoride ion liquid high-temperature digestion hydrocarbon, the party
Method low cost, dissolved efficiency is high, and solute effect is high 40 times compared with water.Hydrocarbon can effectively be solved
The dissolved efficiency of (especially methane).
A kind of method of use fluoride ion liquid high-temperature digestion hydrocarbon gas, the method course of dissolution
Operated using high-pressure installation, add ionic liquid, be filled with gas to be dissolved, realize that hydrocarbon gas are molten
Solution；
The ionic liquid is kation alkyl fluorine richness ionic liquid, anionic alkyl group fluorine richness ionic liquid
Or zwitterion is while alkyl fluoride modified ionic liquid.
Described hydrocarbon is C1-C4 alkane, C2-C4 alkene or C2-C4 alkynes.
Described C1-C4 alkane optimization methane or ethane；Described C2-C4 alkene optimal ethylenes, it is described
The preferred acetylene of C2-C4 alkynes.
The alkyl fluoride modified anion of described anionic alkyl group fluorine richness ionic liquid is：RF1SO3 -, RF2BF3 -
Or RF3CH2CN-, in the case of the anion of above-described ionic liquid, cation type is imidazoles,
Pyridines, croak pyridine class, pyroles, quaternary phosphine salt, quaternary ammonium salt.
The RF1SO3 -, RF1=CmF2m+1, m is 2~12；
The RF2BF3 -, RF2=CnF2n+1, n is 1~4；
The RF3CH2CN-, RF3=CiHjF2i+1-j, i is that 1~6, j is 2~9.
Its structure of the cation type is as follows：
Wherein, R is hydrocarbon chain, or alkyl chain and aryl chain containing fluorine richness.
The structure of the kation alkyl fluorine richness ionic liquid alkyl fluoride modified cation is：
Wherein n is 0~7；
OrWherein RF=CnF2n+1, n is 1~7；
Described ionic liquid is for more than in the case of four kinds of fluorine richness cations, and anionic type is as follows：HSO4 ‐,
H2PO4 ‐,BF4 ‐,PF6 ‐,Cl‐,Br‐,NTf2 ‐,TFA‐,Ac‐Or OTf‐。
The form of the ionic liquid absorption, at least a kind of ionic liquid can be pure ionic liquid, from
Sub- liquid film, is supported on remaining material.
The solution temperature of the dissolving method is 60-180 DEG C, and solution presasure is 0.5-15MPa.
A kind of method of fluoride ion liquid high-temperature digestion hydrocarbon that the present invention is provided, described ion
The form of liquid absorption, at least a kind of ionic liquid can be pure ionic liquid, and ionic liquid film is born
It is loaded on remaining material.
The present invention calculates the solubility of hydrocarbon gas using Henry's law.
H=Px wherein H are Henry's constant, and units MPa, P is the equilibrium partial pressure of hydrocarbon gas
MPa, x are hydrocarbon molar fraction in the liquid phase.
Be applied in the dissolving with high temperature to hydrocarbon ionic liquid containing fluorine richness, such as by the present invention
[Bmim] [PFBS] is general ionic liquid (such as [Bmim] [H to the dissolved fraction of methane2SO4]) 4.4 times,
Solution temperature can be from 60 DEG C~180 DEG C.On the one hand in reaction, increase the concentration of methane, improve liquid gas anti-
The efficiency answered, is conducive to the conversion of hydrocarbon.
Advantages of the present invention：A kind of side of fluoride ion liquid high-temperature digestion hydrocarbon that the present invention is provided
Method.The fluoride ion liquid physical chemistry is stable in properties, prepares simply, can be used for hydrocarbon dissolving
Transformation system, compared to the solute effect that aqueous phase system dissolving molar fraction improves 40 times, moreover it can be used to gaseous carbon
The storage transport of hydrogen compound.
Brief description of the drawings
Fig. 1 is dissolution equipment schematic diagram of the present invention, wherein 1 gas cylinder, 2 air accumulators (V1), 3 solution presasures
Kettle (V2), 4 pressure sensors, 5 recording instrument without paper, 6 temperature sensors, 7 oil bath heatings.
Specific embodiment
By taking methane and ethane dissolving as an example, embodiment party of the present invention is further illustrated by embodiment and comparison example
Formula and produced effect, but protection scope of the present invention is not limited to the content listed by embodiment.
Embodiment 1,
Methane is in 1- butyl -3- methylimidazoles perfluoro butyl sulfosalt [Bmim] [PFBS] at illustrating 140 DEG C
Solute effect.
15ml 1- butyl -3- methylimidazoles perfluoro butyl sulfosalt [Bmim] [PFBS] is weighed in the reaction of 55ml
In kettle, under vacuum stir 10 minutes, toward air accumulator in fill 4MPa, 3MPa, 2MPa, 1MPa CH4,
After after pressure and temperature stabilization, gas in air accumulator is filled with reactor, 140 DEG C of temperature control, stirred, treat first
Pressure and temp stabilization is realized in alkane absorption equilibrium (dissolution equipment is shown in Fig. 1).
Methane content is absorbed by the volumetric pressure temperature computation of each kettle, by the uptake under four groups of different pressures
Further it is converted into Henry's constant.Obtain result as shown in table 1：
The solubility of 140 DEG C of methane in table 1 [Bmim] [PFBS]
With [Bmim] [PFBS] ionic liquid, the Henry's constant of dissolving is 30.9MPa, by H=Px during 4MPa
Converse the assimilation effect of 13% molar fraction.
Embodiment 2,
Methane is in 1- ethyl-3-methylimidazoles trifluoro (trifluoromethyl) borate at illustrating 140 DEG C
[Bmim][CF3BF3] in solute effect.
, with embodiment 1, methane is in 1- ethyl-3-methylimidazole trifluoro (fluoroforms at 140 DEG C of measurement for experimental technique
Base) borate [Bmim] [CF3BF3] in solubility, calculate Henry's constant.Obtain result as shown in table 2：
Table 2 [Bmim] [CF3BF3] in 140 DEG C of methane solubility
Embodiment 1-2 illustrates solution absorption effect of the different alkyl fluoride modified ionic liquids to methane.
Embodiment 3
Methane is in 1- butyl -3- methylimidazoles perfluoro butyl sulfosalt [Bmim] [PFBS] at illustrating 60 DEG C
Solute effect.
, with embodiment 1, methane is in 1- butyl -3- methylimidazole perfluoro butyl sulfonic acid at 60 DEG C of measurement for experimental technique
Solubility in salt [Bmim] [PFBS], calculates Henry's constant.Obtain result as shown in table 3：
The solubility of 60 DEG C of methane in table 3 [Bmim] [PFBS]
From 60 DEG C~140 DEG C with the wide variation of temperature, to first in present invention design fluoride ion liquid
The solvability influence of alkane is little, and ionic liquid can at high temperature keep Methane solubility high, and herein
At a temperature of, most of water and organic reagent have reached boiling point or decomposition, steady at high temperature with ionic liquid
Surely dissolve the invention of hydrocarbon gas, can be applied to the main gaseous state fossil energy such as methane, ethane into
In the efficient utilization for dividing, the dissolving conversion of methane is advantageous to.
Comparative example 4
Methane is in 1- ethyl-3-methylimidazoles disulfate [Bmim] [HSO at illustrating 140 DEG C4] in dissolving
Effect.
, with embodiment 1, methane is in 1- ethyl-3-methylimidazole disulfates at 140 DEG C of measurement for experimental technique
[Bmim][HSO4] in solubility, calculate Henry's constant.Obtain result as shown in table 4：
Table 4 [Bmim] [HSO4] in 140 DEG C of methane solubility
With [Bmim] [HSO4] ionic liquid, Henry's constant is 98.4MPa, and only 4% is conversed during 4MPa
The assimilation effect of molar fraction, compared to the same terms under, [Bmim] [PFBS] be its dissolving molar fraction 4
Times.
Comparative example 5
Methane is in 1- ethyl-3-methylimidazoles disulfate [Bmim] [HSO at illustrating 60 DEG C4] in dissolving effect
Really.
, with embodiment 1, methane is in 1- ethyl-3-methylimidazole disulfates at 60 DEG C of measurement for experimental technique
[Bmim][HSO4] in solubility, calculate Henry's constant.Obtain result as shown in table 5：
Table 5 [Bmim] [HSO4] in 60 DEG C of methane solubility
Methane is in 1- ethyl-3-methylimidazoles disulfate [Bmim] [HSO at illustrating 60 DEG C4] in dissolving effect
Fruit is even worse, not as 140 DEG C.
Comparative example 6
Illustrate solute effect of the methane in water at 60 DEG C.
Experimental technique calculates Henry's constant with embodiment 1, solubility of the methane in water at 60 DEG C of measurement.
Obtain result as shown in table 6：
The solubility of 60 DEG C of methane in the water of table 6
From comparative example as can be seen that being free of alkyl fluoride modified ionic liquid or water, the absorption to methane
Ability is extremely limited, and under 4MPa, dissolution system molar fraction is 0.33%, at 60 DEG C, [Bmim] [PFBS]
It is high 40 times in the absorptance water of methane in ionic liquid.No matter alkyl fluoride modified ionic liquid is to gas reaction
Or storage transport is all particularly significant.
Embodiment 7
Ethane is in 1- butyl -3- methylimidazoles perfluoro butyl sulfosalt [Bmim] [PFBS] at illustrating 140 DEG C
Solute effect.
, with embodiment 1, ethane is in 1- butyl -3- methylimidazole perfluoro butyl sulfonic acid at 140 DEG C of measurement for experimental technique
Solubility in salt [Bmim] [PFBS], calculates Henry's constant.Obtain result as shown in table 7：
The solubility of 140 DEG C of ethane in table 7 [Bmim] [PFBS]
Ionic liquid not only can be with dissolved methane, while it is hydrocarbon to dissolve the gaseous states such as ethane, ethene, acetylene
Compound, methane is wherein most insoluble gas, and remaining gas dissolving advantage becomes apparent.
Claims (9)
1. a kind of method of use fluoride ion liquid high-temperature digestion hydrocarbon gas, it is characterised in that：
The method course of dissolution is operated using high-pressure installation, adds ionic liquid, is filled with gas to be dissolved and is realized gaseous state
Hydrocarbon dissolves；
The ionic liquid is kation alkyl fluorine richness ionic liquid, anionic alkyl group fluorine richness ionic liquid
Or zwitterion is while alkyl fluoride modified ionic liquid.
2. according to a kind of side of the use fluoride ion liquid high-temperature digestion hydrocarbon described in claim 1
Method, it is characterised in that：Described hydrocarbon is C1-C4 alkane, C2-C4 alkene or C2-C4 alkynes.
3. according to a kind of side of the use fluoride ion liquid high-temperature digestion hydrocarbon described in claim 2
Method, it is characterised in that：Described C1-C4 alkane optimization methane or ethane；Described C2-C4 alkene is preferred
Ethene, the preferred acetylene of C2-C4 alkynes.
4. according to a kind of method of use fluoride ion liquid high-temperature digestion hydrocarbon described in claim 1,
It is characterized in that the alkyl fluoride modified anion of described anionic alkyl group fluorine richness ionic liquid is：RF1SO3 -,
RF2BF3 -Or RF3CH2CN-, in the case of the anion of above-described ionic liquid, cation type is miaow
Azole, pyridines, croak pyridine class, pyroles, quaternary phosphine salt, quaternary ammonium salt.
5. according to a kind of method of use fluoride ion liquid high-temperature digestion hydrocarbon described in claim 4,
It is characterized in that the RF1SO3 -, RF1=CmF2m+1, m is 2~12；
The RF2BF3 -, RF2=CnF2n+1, n is 1~4；
The RF3CH2CN-, RF3=CiHjF2i+1-j, i is that 1~6, j is 2~9.
6. according to a kind of method of use fluoride ion liquid high-temperature digestion hydrocarbon described in claim 4,
It is characterized in that its structure of the cation type is as follows：
Wherein, R is hydrocarbon chain, or alkyl chain and aryl chain containing fluorine richness.
7. according to a kind of method of the use fluoride ion liquid high-temperature digestion hydrocarbon described in claim 1,
It is characterized in that the structure of kation alkyl fluorine richness ionic liquid alkyl fluoride modified cation is：
Wherein n is 0~7；
OrWherein RF=CnF2n+1, n is 1~7；
Described ionic liquid is for more than in the case of four kinds of fluorine richness cations, and anionic type is as follows：HSO4 ‐,
H2PO4 ‐,BF4 ‐,PF6 ‐,Cl‐,Br‐,NTf2 ‐,TFA‐,Ac‐Or OTf.
8. according to a kind of method of the use fluoride ion liquid high-temperature digestion hydrocarbon described in claim 1,
It is characterized in that the form of ionic liquid absorption, at least a kind of ionic liquid, can be pure ionic liquid,
Ionic liquid film, is supported on remaining material.
9. according to a kind of method of the use fluoride ion liquid high-temperature digestion hydrocarbon described in claim 1,
It is characterized in that solution temperature is 60-180 DEG C, solution presasure is 0.5-15MPa.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114656317A (en) * | 2020-12-22 | 2022-06-24 | 中国石油化工股份有限公司 | Method and system for preparing olefin through oxidative coupling of methane and application of method and system |
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| CN101038249A (en) * | 2006-03-14 | 2007-09-19 | 中国科学院过程工程研究所 | Method and device for measuring absorbing capacity of organic solvent volatile gas in ion liquid |
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| CN114656317A (en) * | 2020-12-22 | 2022-06-24 | 中国石油化工股份有限公司 | Method and system for preparing olefin through oxidative coupling of methane and application of method and system |
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