CN108479308A - A method of removing carbonyl sulfur using ionic liquid compounding agent - Google Patents
A method of removing carbonyl sulfur using ionic liquid compounding agent Download PDFInfo
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- CN108479308A CN108479308A CN201810264976.8A CN201810264976A CN108479308A CN 108479308 A CN108479308 A CN 108479308A CN 201810264976 A CN201810264976 A CN 201810264976A CN 108479308 A CN108479308 A CN 108479308A
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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
- B01D53/1456—Removing acid components
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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
- B01D53/1425—Regeneration of liquid 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
- B01D53/1493—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
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/30—Ionic liquids and zwitter-ions
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Abstract
The present invention relates to a kind of method removing carbonyl sulfur using ionic liquid compounding agent, carbonyl sulfur condition is in the ionic liquid compounding agent absorbing and removing tail gas of sulphur：It is 20 to absorb temperatureoC‑60oC, the tail gas of sulphur volume space velocity containing COS are 0.01h‑1‑10 h‑1, the removal efficiency of carbonyl sulfur is up to 80% 99.5%；By the ionic liquid compounding agent after failure 90oC‑120 oC heats 2h 5h, after the COS desorptions after absorbing, realizes the regeneration of ionic liquid compounding agent, the ionic liquid compounding agent after regeneration recycles；Ionic liquid compounding agent is mixed to prepare by alkanolamine solution, ionic liquid, absorption enhancement agent, water.The present invention effectively raises the removal efficiency of COS by the synergistic effect of alkanolamine solution chemical absorbing and ionic liquid Physical Absorption in ionic liquid compounding agent, can COS in deep removal tail gas of sulphur.
Description
Technical field
The present invention relates to tail gas of sulphur field of purification, and in particular to a kind of to remove carbonyl sulfur using ionic liquid compounding agent
Method.
Background technology
H is mainly contained in tail gas of sulphur2S、SO2、COS、CS2It is natural gas and oil with the sulfur-bearings ingredient such as elemental sulfur steam
The sour gas of refining industry postpones the tail gas being discharged from sulfur plants by Sulfur recycling installment.The processing work of tail gas of sulphur at present
Skill is mainly the SCOT techniques of Shell companies of Holland exploitation, and process is：Hydrogenating reduction is first passed through to convert various forms sulphur to
H2S, then with the most H of alkanolamine solution absorbing and removing2S is to realize that tail gas clean-up, purified tail gas are converted into poison by burning
The smaller SO of evil property2High altitude discharge afterwards.
New gas discharge standard（GB31570-2015）In, SO after tail gas of sulphur burns2Con trolling index by marking originally
Accurate 960mg/Nm3It is reduced to 100mg/Nm3；For the developed area that environmental carrying capacity is limited, practical control is more reduced to
50mg/Nm3.In actual condition, when using hydrogenating reduction sulfide, by the how many difference of difference, the COS contents of tail gas of sulphur composition
Not and the factors such as the length of catalyst usage time influence, and COS can not be made to be fully converted into H2S.Thus, when not by
When the COS concentration of conversion is high, since amine industrial at present takes off very low to the removal efficiency of COS in processing procedure, only 30% left side
The right side, COS contents are higher than 50mg/Nm after causing hydrogenation on tail gas of sulphur to handle3The case where it is more, tail gas of sulphur burn after, it is difficult to reach
The SO required to GB31570-20152Less than 100mg/Nm3Con trolling index.
The de- processing of the amine of carbonyl sulfur at present is main insufficient：（1）COS removal efficiencies are low.Usually ensure efficient removal inorganic sulfur
Compound H2S, water content is larger in absorbent, is unfavorable for the dissolving of organic sulfur compound COS, therefore the performance of its de- COS in this way
It is poor.（2）Absorbent regeneration is of high cost.For COS, the small feature of solubility improves to strengthen absorption in aqueous solution
A certain amount of isopropanol can be added in absorbent in its removal efficiency, and enhancement factor maximum is up to 4（Modern chemical industry, volume 24,19-
22,2004）.But the defect of the method is：Since the boiling point of isopropanol is relatively low（82.45oC）, in absorbent heats regenerative process
There is a large amount of loss, to ensure COS removal efficiencies, needs constantly to add isopropanol so that operating cost constantly improves.
In conclusion a kind of method of the carbonyl sulfur of efficient removal that can be inexpensive of offer is that this field is urgently to be resolved hurrily
Problem.
Ionic liquid has unique performance as a kind of efficient " green organic solvent "：There is wider liquid state range；
It is non-volatile；Almost without vapour pressure；It is not easy to explode；Preferable thermal stability and chemical stability.Using to organic sulfur especially
COS has carbonyl sulfur in the ionic liquid compounding agent of good solubility and thermal stability removing tail gas of sulphur, to tail gas of sulphur dirt
Dye object control has great importance.
Invention content
It is this to utilize ion the object of the present invention is to provide a kind of method removing carbonyl sulfur using ionic liquid compounding agent
The method of liquid compounding agent removing carbonyl sulfur is used to solve very low to the removal efficiency of COS in the de- processing procedure of amine industrial at present
The problem of.
The technical solution adopted by the present invention to solve the technical problems is：It is this to remove carbonyl using ionic liquid compounding agent
The method of sulphur：
Carbonyl sulfur condition is in ionic liquid compounding agent absorbing and removing tail gas of sulphur：It is 20 to absorb temperatureoC-60oC, containing COS's
Tail gas of sulphur volume space velocity is 0.01h-1-10 h-1, the removal efficiency of carbonyl sulfur reaches 80%-99.5%；By the ionic liquid after failure
Compounding agent is 90oC-120 oC heats 2h-5h, after the COS desorptions after absorbing, realizes ionic liquid compounding agent again
Raw, the ionic liquid compounding agent after regeneration recycles；
Ionic liquid compounding agent is mixed to prepare by alkanolamine solution, ionic liquid, absorption enhancement agent, water, wherein ionic liquid quality
Score is 10wt %-30wtThe mass fraction of %, alkanolamine solution are 10wt%-50wt%；Absorption enhancement agent mass fraction is 15wt%-50wt%, surplus are water；Absorption enhancement agent is dimethyl sulfoxide, sulfolane, N- N-formyl morpholine Ns, N-Methyl pyrrolidone, poly- second
One or both of glycol, propene carbonate；
Ionic liquid preparation method：Into organic compounds containing nitrogen A, halogenated hydrocarbon compound B is added dropwise in constant pressure dropwise, makes nitrogenous to have
The molar ratio of machine compound A and halogenated hydrocarbon compound B are 1：1-1：3, in reaction temperature 10oC-120oUnder C, uniform stirring fills
After dividing reaction 6h-24h, then through rotary evaporation in vacuo purification, washing, drying, obtain C+X-Ionic liquid, wherein C+For nitrogenous sun
Ion, X-For halide anion；Organic compounds containing nitrogen A is、、In one kind
Or two kinds；C+For imidazole cation（）, pyridine type cation（）, pyrroles's type sun from
Son（）, in it is one or two kinds of；Wherein R1、R2The alkyl for being 1-12 for carbon atom number.
Rotary evaporation in vacuo purification, washing, dry specific method are in said program：Rotary evaporation in vacuo purifies
40min-120 min, product are washed 3-5 times with ether, then 60oC-110 oDry 6h-24h under C.
Halogenated hydrocarbon compound B is one or both of RCl, RBr, RI in said program, and wherein R is that carbon atom number is
The alkyl of 1-12；X-For：Cl-、Br-、I-One or both of.
Alkanolamine solution is triethanolamine (TEA), diglycolamine (DGA), diisopropanolamine (DIPA) (DIPA), first in said program
At least one of base diethanol amine (MDEA).
Absorption enhancement agent is dimethyl sulfoxide, sulfolane, N- N-formyl morpholine Ns, N-Methyl pyrrolidone, poly- second in said program
One or both of glycol, propene carbonate.
Carbonyl sulfur condition is in said program intermediate ion liquid compounding agent absorbing and removing tail gas of sulphur：Absorbing temperature is
20oC-50oC, gas volume air speed are 0.01h-1-7 h-1, COS removal efficiencies reach 90%-99.5%.
The invention has the advantages that：
1, the present invention removes carbonyl sulfur in tail gas of sulphur with ionic liquid compounding agent, passes through alkanolamine solution in ionic liquid compounding agent
The synergistic effect of chemical absorbing and ionic liquid Physical Absorption effectively raises the removal efficiency of COS, can deep removal sulphur tail
COS in gas.
2, ionic liquid compounding agent absorbent prepared by the present invention, more conventional alkanolamine solution absorbent have stronger organic sulfur
Dissolubility, and yield is higher in ionic liquid building-up process, preparation process is simple, has broad application prospects.
3, intermediate ion liquid compounding agent regenerative process of the present invention is simple, it is only necessary to which the COS that heating parsing absorbs can be realized
It is recycled.Ionic liquid is non-volatile, almost without vapour pressure, and has good thermal stability, therefore, in regenerative process
Loss is few, the long lifespan of absorbent, and operating cost is low.
Specific implementation mode
The present invention is further illustrated below：
Embodiment 1：
This method for removing carbonyl sulfur using ionic liquid compounding agent：
Carbonyl sulfur condition is in ionic liquid compounding agent absorbing and removing tail gas of sulphur：It is 30 to absorb temperatureoC, tail gas of sulphur air speed
For 6h-1, after imidazole type ion liquid compounding agent absorption, COS contents are by 48mg/m in tail gas of sulphur3Drop to 2.1mg/
m3, while H is not detected2The total removal efficiency of S, COS is 95.6%.
When COS removal efficiencies be less than 90%, imidazole type ion liquid compounding agent is regenerated, 100o2h is heated under C, is made
It desorbs the COS absorbed, and imidazole type ion liquid compounding agent is regenerated.
Prepare ionic liquid：By the n-octane bromide of 62.2g（C8H17Br）Constant pressure is added drop-wise to dropwise has been added 24.6g N-
Methylimidazole（）In, 25oAfter uniform stirring fully reacts 6h under C, by liquid after reaction 80 oVacuum under C
Rotary evaporation purifies, and product is washed 4 times with ether, by gained thick liquid 100 oDry 8h, it is pungent to obtain 1- methyl -3- under C
Base imidazoles hydrobromate () imidazole type ion liquid.
Prepare ionic liquid compounding agent：Imidazole type ion liquid compounding agent forms based on mass fraction：20wt%1- methyl -3- is pungent
Base imidazoles hydrobromate（）Ionic liquid, 20wt% methyl diethanolamines (MDEA), 5wt% diisopropanolamine (DIPA)s (DIPA), 20wt% sulfolane（）, 35wt% water.
Embodiment 2：
This method for removing carbonyl sulfur using ionic liquid compounding agent：
Carbonyl sulfur condition is in ionic liquid compounding agent absorbing and removing tail gas of sulphur：It is 40 to absorb temperatureoC, tail gas of sulphur air speed
For 6 h-1, after pyrroles's type ionic liquid compounding agent absorption, COS contents are by 48mg/m in tail gas of sulphur3Drop to 1.4mg/
m3, while H is not detected2The total removal efficiency of S, COS is 97.1%.
When COS removal efficiencies be less than 90%, pyrroles's type ionic liquid compounding agent is regenerated, 100o2.5h is heated under C,
The COS for making its desorption absorb, pyrroles's type ionic liquid compounding agent are regenerated.
Prepare ionic liquid：By the chloro-normal butane C of 5.8g4H9Cl constant pressures are added drop-wise to dropwise has been added 5g N- methylpyrroles
Alkane（）In, 70oAfter uniform stirring fully reacts 12h under C, by liquid after reaction 70 oVacuum rotating steams under C
Hair purification, product is washed 3 times with ether, by gained thick liquid 100 oDry 6h under C.N- methyl-N- butyl pyrroles can be obtained
Cough up hydrochloride () pyrroles's type ionic liquid.
Prepare ionic liquid compounding agent：Ionic liquid compounding agent forms：25wt%N- methyl-N- fourths
Base pyrrole hydrochloride () ionic liquid, 30wt% methyl diethanolamines (MDEA), 20wt% dimethyl sulfoxides（DMSO）, 25wt%
Water.
Embodiment 3
This method for removing carbonyl sulfur using ionic liquid compounding agent：
Carbonyl sulfur condition is in ionic liquid compounding agent absorbing and removing tail gas of sulphur：It is 40 to absorb temperatureoC, tail gas of sulphur air speed
For 7h-1, after ionic liquid compounding agent absorption, COS contents are by 48mg/m in tail gas of sulphur3Drop to 1.6mg/m3, simultaneously
H is not detected2The total removal efficiency of S, COS is 96.7%.
When COS removal efficiencies be less than 90%, pyridine type ionic liquid compounding agent is regenerated, 110o2.5h is heated under C,
The COS for making its desorption absorb, pyridine type ionic liquid compounding agent are regenerated.
Prepare ionic liquid：By the chloro n-dodecane C of 20.5g12H25Cl constant pressures are added drop-wise to dropwise has been added 6.2g pyridines
（）In, 100oUniform stirring fully reacts 6h under C, by solution after reaction 80 oRotary evaporation in vacuo purifies under C, production
Object is washed 3 times with ether, by gained golden yellow thick liquid 110 oDry 8h under C.N- dodecyls-pyridine hydrochloric acid can be obtained
Salt () ionic liquid.
Prepare ionic liquid compounding agent：Ionic liquid compounding agent is based on mass fraction：18wt% N- dodecyls-pyridine
Hydrochloride () ionic liquid, 30wt% methyl diethanolamines (MDEA), 15wt% sulfolane（）, 35wt% water.
Embodiment 4：
This method for removing carbonyl sulfur using ionic liquid compounding agent：
Carbonyl sulfur condition is in ionic liquid compounding agent absorbing and removing tail gas of sulphur：It is 40 to absorb temperatureoC, tail gas of sulphur air speed
For 5h-1, after ionic liquid compounding agent absorption, COS contents are by 48mg/m in tail gas of sulphur3Drop to 0.45mg/m3, simultaneously
H is not detected2The total removal efficiency of S, COS is 99.1%.
When COS removal efficiencies be less than 90%, compound ion liquid compounding agent is regenerated, 100o2h is heated under C, makes it
The COS absorbed is desorbed, compound ion liquid compounding agent is regenerated.
Prepare ionic liquid：By the iodomethane CH of 28.3g3I constant pressures are added drop-wise to dropwise has been added 7.2g N- crassitudes
（）In, 15oAfter uniform stirring fully reacts 10h under C, by liquid after reaction 70 oRotary evaporation in vacuo under C
Purification, product is washed 4 times with ether, by gained thick liquid 100 oDry 6h under C.N, N- dimethyl pyrrole hydrogen iodine can be obtained
Hydrochlorate () ionic liquid.
Prepare ionic liquid compounding agent：Ionic liquid compounding agent mass fraction is calculated as：15wt% N, N- dimethyl pyrrole hydrogen
Iodate () ionic liquid, 10wt%1- methyl -3- octylimidazole hydrobromates（）Ionic liquid,
30wt% methyl diethanolamines (MDEA), 10wt% dimethyl sulfoxides（DMSO）, 10wt% sulfolane（）, 25wt% water.
Claims (6)
1. a kind of method removing carbonyl sulfur using ionic liquid compounding agent, it is characterised in that：It is this to be compounded using ionic liquid
The method that agent removes carbonyl sulfur：
Carbonyl sulfur condition is in ionic liquid compounding agent absorbing and removing tail gas of sulphur：It is 20 to absorb temperatureoC-60oC, the sulphur containing COS
Sulphur exhaust gas volumes air speed is 0.01h-1-10 h-1, the removal efficiency of carbonyl sulfur reaches 80%-99.5%；Ionic liquid after failure is answered
Ingredients is 90oC-120 oC heats 2h-5h, after the COS desorptions after absorbing, realizes the regeneration of ionic liquid compounding agent,
Ionic liquid compounding agent after regeneration recycles；
Ionic liquid compounding agent is mixed to prepare by alkanolamine solution, ionic liquid, absorption enhancement agent, water, wherein ionic liquid quality
Score is 10wt %-30wtThe mass fraction of %, alkanolamine solution are 10wt%-50wt%；Absorption enhancement agent mass fraction is 15wt%-50wt%, surplus are water；Absorption enhancement agent is dimethyl sulfoxide, sulfolane, N- N-formyl morpholine Ns, N-Methyl pyrrolidone, poly- second
One or both of glycol, propene carbonate；
Ionic liquid preparation method：Into organic compounds containing nitrogen A, halogenated hydrocarbon compound B is added dropwise in constant pressure dropwise, makes nitrogenous to have
The molar ratio of machine compound A and halogenated hydrocarbon compound B are 1：1-1：3, in reaction temperature 10oC-120oUnder C, uniform stirring fills
After dividing reaction 6h-24h, then through rotary evaporation in vacuo purification, washing, drying, obtain C+X-Ionic liquid, wherein C+For nitrogenous sun
Ion, X-For halide anion；Organic compounds containing nitrogen A is、、In one kind or two
Kind；C+For imidazole cation（）, pyridine type cation（）, pyrroles type cation（）, in it is one or two kinds of；Wherein R1、R2The alkyl for being 1-12 for carbon atom number.
2. the method according to claim 1 for removing carbonyl sulfur using ionic liquid compounding agent, it is characterised in that：Described
Rotary evaporation in vacuo purification, washing, dry specific method are：Rotary evaporation in vacuo purifies 40min-120 min, product second
Ether washs 3-5 times, then 60oC-110 oDry 6h-24h under C.
3. the method according to claim 2 for removing carbonyl sulfur using ionic liquid compounding agent, it is characterised in that：Described
Halogenated hydrocarbon compound B is one or both of RCl, RBr, RI, and wherein R is the alkyl that carbon atom number is 1-12；X-For：
Cl-、Br-、I-One or both of.
4. the method according to claim 3 for removing carbonyl sulfur using ionic liquid compounding agent, it is characterised in that：Described
Alkanolamine solution is at least one of triethanolamine, diglycolamine, diisopropanolamine (DIPA), methyl diethanolamine.
5. the method according to claim 4 for removing carbonyl sulfur using ionic liquid compounding agent, it is characterised in that：Described
Absorption enhancement agent is in dimethyl sulfoxide, sulfolane, N- N-formyl morpholine Ns, N-Methyl pyrrolidone, polyethylene glycol, propene carbonate
It is one or two kinds of.
6. the method according to claim 5 for removing carbonyl sulfur using ionic liquid compounding agent, it is characterised in that：Described
Carbonyl sulfur condition is in ionic liquid compounding agent absorbing and removing tail gas of sulphur：It is 20 to absorb temperatureoC-50oC, gas volume air speed
For 0.01h-1-7 h-1, COS removal efficiencies reach 90%-99.5%.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111871193A (en) * | 2020-07-15 | 2020-11-03 | 中石化南京化工研究院有限公司 | Absorbent for removing hydrogen sulfide and carbonyl sulfide from acid gas |
| CN113058561A (en) * | 2021-04-09 | 2021-07-02 | 浙江工业大学 | Recyclable ionic liquid adsorbent and preparation method and application thereof |
| CN113058419A (en) * | 2021-04-08 | 2021-07-02 | 浙江工业大学 | Supported ionic liquid desulfurization material and preparation method and application thereof |
| CN113070040A (en) * | 2021-04-22 | 2021-07-06 | 浙江工业大学 | Carbon material-loaded ionic liquid adsorption material for removing carbonyl sulfide and application thereof |
| CN113101782A (en) * | 2021-04-08 | 2021-07-13 | 浙江工业大学 | Functionalized ionic liquid absorption liquid and preparation method and application thereof |
| CN113368665A (en) * | 2021-07-01 | 2021-09-10 | 浙江工业大学 | Renewable complex ionic liquid desulfurizer as well as preparation method and application thereof |
| CN114762789A (en) * | 2021-01-15 | 2022-07-19 | 中国石油化工股份有限公司 | High-sulfur high-heavy hydrocarbon oilfield associated gas absorbent and using method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111871193A (en) * | 2020-07-15 | 2020-11-03 | 中石化南京化工研究院有限公司 | Absorbent for removing hydrogen sulfide and carbonyl sulfide from acid gas |
| CN114762789A (en) * | 2021-01-15 | 2022-07-19 | 中国石油化工股份有限公司 | High-sulfur high-heavy hydrocarbon oilfield associated gas absorbent and using method thereof |
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| CN113058419A (en) * | 2021-04-08 | 2021-07-02 | 浙江工业大学 | Supported ionic liquid desulfurization material and preparation method and application thereof |
| CN113101782A (en) * | 2021-04-08 | 2021-07-13 | 浙江工业大学 | Functionalized ionic liquid absorption liquid and preparation method and application thereof |
| CN113058419B (en) * | 2021-04-08 | 2023-02-28 | 浙江工业大学 | Supported ionic liquid desulfurization material and preparation method and application thereof |
| CN113058561A (en) * | 2021-04-09 | 2021-07-02 | 浙江工业大学 | Recyclable ionic liquid adsorbent and preparation method and application thereof |
| CN113070040A (en) * | 2021-04-22 | 2021-07-06 | 浙江工业大学 | Carbon material-loaded ionic liquid adsorption material for removing carbonyl sulfide and application thereof |
| CN113368665A (en) * | 2021-07-01 | 2021-09-10 | 浙江工业大学 | Renewable complex ionic liquid desulfurizer as well as preparation method and application thereof |
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