CN101601961A - Absorb SO with halogenated alkyl quaternary ammonium salt ionic liquid 2The method of gas - Google Patents

Absorb SO with halogenated alkyl quaternary ammonium salt ionic liquid 2The method of gas Download PDF

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CN101601961A
CN101601961A CNA2009100748011A CN200910074801A CN101601961A CN 101601961 A CN101601961 A CN 101601961A CN A2009100748011 A CNA2009100748011 A CN A2009100748011A CN 200910074801 A CN200910074801 A CN 200910074801A CN 101601961 A CN101601961 A CN 101601961A
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ionic liquid
gas
ammonium
halogenated alkyl
quaternary ammonium
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郭斌
段二红
任爱玲
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Hebei University of Science and Technology
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Hebei University of Science and Technology
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Abstract

The invention provides with halogenated alkyl quaternary ammonium salt ionic liquid and absorb SO 2The method of gas relates to the method for processing organic wastewater technical field.This method absorbs SO with halogenated alkyl quaternary ammonium salt ionic liquid 2The method of gas is characterized in that with halogenated alkyl quaternary ammonium salt ionic liquid as SO 2The absorbent of gas makes the absorbed SO of desire 2Gas is by this ionic liquid, or this ion liquid solution, or the carrier of or load composite by this ionic liquid.The present invention has overcome the deficiency of prior art, has method uniqueness, simple, easy to operate, the SO of technical process 2Absorption efficiency height, cost are low, non-secondary pollution, can be recycling, effective, the characteristics of applied range, economic benefit, environmental benefit and social benefit are good.The ionic liquid building-up process that is adopted is simple, green non-pollution, can be recycling, can also reclaim high purity liquid SO 2, prepare sulfuric acid simultaneously.

Description

Absorb SO with halogenated alkyl quaternary ammonium salt ionic liquid 2The method of gas
Technical field
The present invention relates to the method for processing organic wastewater technical field.
Background technology
Since early 1980s, along with Chinese economic development, to energy industry, particularly the demand of power industry also increases rapidly, and as a few is based on one of country of coal in the world, the consumption of coal in China increases day by day, SO 2Discharge capacity also increase thereupon, China has become SO at present 2Pollute one of the most serious country.Flue gas desulfurization is to reduce industry coal-boiler SO 2The effective ways of discharging, along with the continuous increase of desulphurization plant operation quantity and the continuous expansion of scale, there is a sharp increase in output for desulfuration byproduct, and it is handled problems also to become and becomes increasingly conspicuous.In the flue gas desulfurization technique of present commercial Application, method commonly used is wet method and semi-dry desulfurizing process, but the comprehensive utilization of accessory substance gypsum has restricted the development and the application of above-mentioned technology.The desulfuration byproduct gypsum is idle mostly at present stacks, and forms a large amount of solid and liquid debris, not only takies valuable land resource but also cause secondary pollution.
In recent years because atmosphere pollution is serious day by day and the limitation of existing treatment technology, so have very important application prospect as the absorbent that absorbs sour gas with ionic liquid.But a lot of ionic liquids of research are to SO now 2Solubility all less, and exist viscosity big, synthetic cost height, generative process is long, pollutes limitation such as more serious.
Summary of the invention
The purpose of this invention is to provide with halogenated alkyl quaternary ammonium salt ionic liquid and absorb SO 2The method of gas has method uniqueness, simple, easy to operate, the SO of technical process 2Absorption efficiency height, cost are low, non-secondary pollution, can be recycling, effective, the characteristics of applied range, economic benefit, environmental benefit and social benefit are good.
Main technical schemes of the present invention is: absorb SO with halogenated alkyl quaternary ammonium salt ionic liquid 2The method of gas is characterized in that with halogenated alkyl quaternary ammonium salt ionic liquid as SO 2The absorbent of gas makes the absorbed SO of desire 2Gas is by this ionic liquid, or this ion liquid solution, or the carrier of or load composite by this ionic liquid.
Optimum range during described the absorption is: the temperature optimum range is-10 ℃ to 150 ℃, and the pressure optimum range is 1kPa to 10MPa.
The absorbed SO of described desire 2Gas can be pure SO 2Gas is perhaps for containing 0.01%～30% SO 2Mist or flue gas.
Describedly absorb SO with halogenated alkyl quaternary ammonium salt ionic liquid 2The method of gas can be with high-purity SO after the absorption 2Gas prepares liquid SO 2, with low concentration SO 2Gas through catalytic oxidation again with water prepared in reaction sulfuric acid, recycle.
The method for making of described halogenated alkyl quaternary ammonium salt ionic liquid is: at a certain temperature, have urea, thiocarbamide and caprolactam to react with the quaternary ammonium salt of tetramethyl ammonium chloride, ammonium thiocyanate or similar structures respectively, generate a series of quaternary ammonium salts ionic liquid.Its structural formula is as follows:
Figure G2009100748011D00021
M is respectively: caprolactam, urea, thiocarbamide
R 1, R 2, R 3And R 4Be respectively: H, CH 3, CH 2CH 3, (CH 2) 2CH 3, (CH 2) 3CH 3, (CH 2) 4CH 3, (CH 2) 5CH 3, (CH 2) 6CH 3, (CH 2) 7CH 3, (CH 2) 8CH 3, (CH 2) 9CH 3, (CH 2) 10CH 3, (CH 2) 11CH 3, (CH 2) 12CH 3, (CH 2) 13CH 3, (CH 2) 14CH 3, (CH 2) 15CH 3
X is respectively: Br, Cl, SCN
Described halogenated alkyl quaternary ammonium salt ionic liquid, a compounds are caprolactam, urea or thiocarbamide.
Described halogenated alkyl quaternary ammonium salt ionic liquid, another kind of compound are tetramethyl ammonium chloride, 4 bromide, etamon chloride, tetraethylammonium bromide, 4-propyl ammonium chloride, 4-propyl bromide, tetrabutylammonium chloride, TBAB, four pentyl ammonium chloride, the four pentyl ammonium bromide, four hexyl ammonium chlorides, four hexyl ammonium bromides, four heptyl ammonium chlorides, four heptyl ammonium bromides, four octyl group ammonium chlorides, four octyl group ammonium bromides, four nonyl ammonium chlorides, four nonyl ammonium bromides, four decyl ammonium chlorides, four decyl ammonium bromides, the undecyl trimethyl ammonium chloride, the undecyl trimethylammonium bromide, DTAC, DTAB, the tridecyl trimethyl ammonium chloride, the tridecyl trimethylammonium bromide, tetradecyl trimethyl ammonium chloride, TTAB, the pentadecyl trimethyl ammonium chloride, the pentadecyl trimethylammonium bromide, hexadecyltrimethylammonium chloride, softex kw, the hydroxyethyl trimethyl ammonium chloride, ammonium thiocyanate, ammonium chloride or ammonium bromide etc.
The present invention has following remarkable result: overcome the deficiency of prior art, had method uniqueness, simple, easy to operate, the SO of technical process 2Absorption efficiency height, cost are low, non-secondary pollution, can be recycling, effective, the characteristics of applied range, economic benefit, environmental benefit and social benefit are good.The ionic liquid building-up process that is adopted is simple, green non-pollution, and cost is low, absorbs SO 2The efficient height can be recycling, can alleviate present SO 2Gas treatment can also reclaim high purity liquid SO to a large amount of consumption of resource, the energy with to the pollution of environment 2, and finally obtain sulfuric acid.
Be described further below in conjunction with embodiment, but not as a limitation of the invention.
The specific embodiment
Process of the present invention is: use halogenated alkyl quaternary ammonium salt ionic liquid as SO 2The absorbent of gas makes the absorbed SO of desire 2Gas is by this halogenated alkyl quaternary ammonium salt ionic liquid, or the aqueous solution of halogenated alkyl quaternary ammonium salt ionic liquid, or by the carrier of composite between the halogenated alkyl quaternary ammonium salt ionic liquid or load, temperature range is-10 ℃ to 150 ℃, and pressure limit is 1kPa to 10MPa.The absorbed SO of desire 2Gas is pure SO 2Gas is perhaps for containing 0.01%～30% SO 2Mist or flue gas can be with high-purity SO 2Gas prepares liquid SO 2, with low concentration SO 2Gas through catalytic oxidation again with water prepared in reaction sulfuric acid.
The method for making of halogenated alkyl quaternary ammonium salt ionic liquid is: at a certain temperature, have urea, thiocarbamide and caprolactam to react with the quaternary ammonium salt of tetramethyl ammonium chloride, ammonium thiocyanate or similar structures respectively, generate a series of quaternary ammonium salts ionic liquid.
Embodiment 1:
1), synthetic ion liquid experimental rig is reactor, condensing unit, agitating device and Minton dryer.With the caprolactam of accurate weighing, to reactor, open agitator and stir, progressively add an amount of tetrabutylammonium chloride.And at 80 ℃ of following reaction 10h.With gained liquid 50 ℃ of dry 1h in vacuum drying chamber, get the ionic liquid of caprolactam-tetrabutylammonium chloride at last then.
2), with the ionic liquid of the caprolactam-tetrabutylammonium chloride of accurate weighing to absorber, in 25 ℃ of constant temperature.Speed with 10mL/min feeds SO in absorber 2Gas.Absorb the tail gas outlet and feed in the sodium hydroxide solution, absorb SO 2Tail gas.The weight of weighing absorber at regular intervals is until constant weight.SO after the balance 2Mole fraction solubility in ionic liquid is 0.69.
Embodiment 2:
1), synthetic ion liquid experimental rig is reactor, condensing unit, agitating device and Minton dryer.The caprolactam of accurate weighing to reactor, is opened agitator and stirred, progressively add an amount of ammonium thiocyanate.And at 80 ℃ of following reaction 10h.With gained liquid 50 ℃ of dry 1h in vacuum drying chamber, get the ionic liquid of caprolactam-ammonium thiocyanate at last then.
2), with the ionic liquid of the caprolactam-ammonium thiocyanate of accurate weighing to absorber, in 50 ℃ of constant temperature.Speed with 10mL/min feeds SO in absorber 2Gas.Absorb the tail gas outlet and feed in the sodium hydroxide solution, absorb SO 2Tail gas.The weight of weighing absorber at regular intervals is until constant weight.SO after the balance 2Mole fraction solubility in ionic liquid is 0.75.
Embodiment 3:
1), synthetic ion liquid experimental rig is reactor, condensing unit, agitating device and Minton dryer.The urea of accurate weighing to reactor, is opened agitator and stirred, progressively add an amount of hydroxyethyl trimethyl ammonium chloride.And at 120 ℃ of following reaction 10h.With gained liquid 50 ℃ of dry 1h in vacuum drying chamber, get the ionic liquid of urea-hydroxyethyl trimethyl ammonium chloride at last then.
2), with the ionic liquid of the urea-hydroxyethyl trimethyl ammonium chloride of accurate weighing to absorber, in 80 ℃ of constant temperature.Speed with 10mL/min feeds SO in absorber 2Gas.Absorb the tail gas outlet and feed in the sodium hydroxide solution, absorb SO 2Tail gas.The weight of weighing absorber at regular intervals is until constant weight.SO after the balance 2Mole fraction solubility in ionic liquid is 0.64.
Embodiment 4:
1), synthetic ion liquid experimental rig is reactor, condensing unit, agitating device and Minton dryer.The urea of accurate weighing to reactor, is opened agitator and stirred, progressively add an amount of TBAB.And at 120 ℃ of following reaction 10h.With gained liquid 50 ℃ of dry 1h in vacuum drying chamber, get the ionic liquid of urea-TBAB at last then.
2), with the ionic liquid of the urea-TBAB of accurate weighing to absorber, in 80 ℃ of constant temperature.Speed with 10mL/min feeds SO in absorber 2Gas.Absorb the tail gas outlet and feed in the sodium hydroxide solution, absorb SO 2Tail gas.The weight of weighing absorber at regular intervals is until constant weight.SO after the balance 2Mole fraction solubility in ionic liquid is 0.80.
Embodiment 5:
1), synthetic ion liquid experimental rig is reactor, condensing unit, agitating device and Minton dryer.With the caprolactam of accurate weighing, to reactor, open agitator and stir, progressively add an amount of tetrabutylammonium chloride.And at 80 ℃ of following reaction 10h.With gained liquid 50 ℃ of dry 1h in vacuum drying chamber, get the ionic liquid of caprolactam-tetrabutylammonium chloride at last then.
2), the water of the ionic liquid of the caprolactam-tetrabutylammonium chloride of accurate weighing and different proportion is composite to absorber, in 25 ℃ of constant temperature.Speed with 10mL/min feeds SO in absorber 2Gas.Absorb the tail gas outlet and feed in the sodium hydroxide solution, absorb SO 2Tail gas.The weight of weighing absorber at regular intervals is until constant weight.SO after the balance 2Mole fraction solubility in ionic liquid is 0.74.
Embodiment 6:
1), synthetic ion liquid experimental rig is reactor, condensing unit, agitating device and Minton dryer.With the caprolactam of accurate weighing, to reactor, open agitator and stir, progressively add an amount of tetrabutylammonium chloride and TBAB.And at 80 ℃ of following reaction 10h.With gained liquid 50 ℃ of dry 1h in vacuum drying chamber, get the ionic liquid of caprolactam-tetrabutylammonium chloride-TBAB at last then.
2), with the ionic liquid of the caprolactam-tetrabutylammonium chloride-TBAB of accurate weighing to absorber, in 25 ℃ of constant temperature.Speed with 10mL/min feeds SO in absorber 2Gas.Absorb the tail gas outlet and feed in the sodium hydroxide solution, absorb SO 2Tail gas.The weight of weighing absorber at regular intervals is until constant weight.SO after the balance 2Mole fraction solubility in ionic liquid is 0.69.
Embodiment 7:
Contain the above SO of 2000ppm from smeltery or burner 2Gas by dedusting and de-watering apparatus, feed No. 1 packed absorber and halogenated alkyl quaternary ammonium salt class ionic liquid counter-current absorption SO of the present invention then 2Gas, SO in the tail gas that the absorption tower absorbs 2Content reaches China's " discharge standard of air pollutants ", contains SO simultaneously 2The ionic liquid of gas is through desorption column desorption SO 2, high-purity SO 2Through condensation, drying, filtration, compressed again liquefaction makes the sulfur dioxide liquid finished product.
Embodiment 8:
Contain the above SO of 2000ppm from smeltery or burner 2Gas by dedusting and de-watering apparatus, feed No. 1 packed absorber and halogenated alkyl quaternary ammonium salt class ionic liquid counter-current absorption SO of the present invention then 2Gas, SO in the tail gas that the absorption tower absorbs 2Content reaches China's " discharge standard of air pollutants ", contains SO simultaneously 2The ionic liquid of gas is through desorption column desorption SO 2, high-purity SO 2Deliver to low-temperature condenser after drying, under normal pressure, carry out condensation, below liquefaction point-10 ℃, make the sulfur dioxide liquid finished product with ammonia freezing holding temperature.
Embodiment 9:
Contain the above SO of 2000ppm from smeltery or burner 2Gas by dedusting and de-watering apparatus, feed No. 1 packed absorber and halogenated alkyl quaternary ammonium salt class ionic liquid counter-current absorption SO of the present invention then 2Gas, SO in the tail gas that the absorption tower absorbs 2Content reaches China's " discharge standard of air pollutants ", contains SO simultaneously 2The ionic liquid of gas is through desorption column desorption SO 2, low concentration SO 2(content is up to more than 3%), high-load SO 2Through catalytic bed catalysis, catalytic gas obtains sulfuric acid, the SO of low content through No. 2 packed absorbers and water counter-current absorption 2Gas is recycling through No. 1 packed absorber.
Other embodiment: ionic liquid is respectively: caprolactam, urea, thiocarbamide, tetramethyl ammonium chloride, 4 bromide, etamon chloride, tetraethylammonium bromide, 4-propyl ammonium chloride, 4-propyl bromide, tetrabutylammonium chloride, TBAB, four pentyl ammonium chloride, the four pentyl ammonium bromide, four hexyl ammonium chlorides, four hexyl ammonium bromides, four heptyl ammonium chlorides, four heptyl ammonium bromides, four octyl group ammonium chlorides, four octyl group ammonium bromides, four nonyl ammonium chlorides, four nonyl ammonium bromides, four decyl ammonium chlorides, four decyl ammonium bromides, the undecyl trimethyl ammonium chloride, the undecyl trimethylammonium bromide, DTAC, DTAB, the tridecyl trimethyl ammonium chloride, the tridecyl trimethylammonium bromide, tetradecyl trimethyl ammonium chloride, TTAB, the pentadecyl trimethyl ammonium chloride, the pentadecyl trimethylammonium bromide, hexadecyltrimethylammonium chloride, softex kw, the hydroxyethyl trimethyl ammonium chloride, ammonium thiocyanate, ammonium chloride, ammonium bromide, effect is (process is with above-mentioned, slightly) all better.
The present invention is not limited to above-mentioned specific embodiment, and all foundations technical scheme flesh and blood of the present invention is to any simple modification, equivalent variations and replacement etc. that above embodiment did, all in protection scope of the present invention.

Claims (7)

1, absorbs SO with halogenated alkyl quaternary ammonium salt ionic liquid 2The method of gas is characterized in that with halogenated alkyl quaternary ammonium salt ionic liquid as SO 2The absorbent of gas makes the absorbed SO of desire 2Gas is by this ionic liquid, or this ion liquid solution, or the carrier of or load composite by this ionic liquid.
2, according to claim 1ly absorb SO with halogenated alkyl quaternary ammonium salt ionic liquid 2The method of gas, the temperature range when it is characterized in that absorbing is-10 ℃ to 150 ℃, pressure limit is 1kPa to 10MPa.
3, according to claim 2ly absorb SO with halogenated alkyl quaternary ammonium salt ionic liquid 2The method of gas is characterized in that the absorbed SO of described desire 2Gas is pure SO 2Gas is perhaps for containing 0.01%～30% SO 2Mist or flue gas.
4, according to claim 3ly absorb SO with halogenated alkyl quaternary ammonium salt ionic liquid 2The method of gas is characterized in that high-purity SO 2Gas prepares liquid SO 2, with low concentration SO 2Gas through catalytic oxidation again with water prepared in reaction sulfuric acid.
5, according to claim 1ly absorb SO with halogenated alkyl quaternary ammonium salt ionic liquid 2The method of gas, the method for making that it is characterized in that described halogenated alkyl quaternary ammonium salt ionic liquid is: at a certain temperature, there are urea, thiocarbamide and caprolactam to react with the quaternary ammonium salt of tetramethyl ammonium chloride, ammonium thiocyanate or similar structures respectively, generate a series of quaternary ammonium salts ionic liquid.
6, describedly absorb SO according to claim 1,2,3,4 or 5 with halogenated alkyl quaternary ammonium salt ionic liquid 2The method of gas is characterized in that described halogenated alkyl quaternary ammonium salt ionic liquid, and a compounds is caprolactam, urea or thiocarbamide.
7, describedly absorb SO according to claim 1,2,3,4 or 5 with halogenated alkyl quaternary ammonium salt ionic liquid 2The method of gas, it is characterized in that described halogenated alkyl quaternary ammonium salt ionic liquid, another kind of compound is a tetramethyl ammonium chloride, 4 bromide, etamon chloride, tetraethylammonium bromide, 4-propyl ammonium chloride, 4-propyl bromide, tetrabutylammonium chloride, TBAB, four pentyl ammonium chloride, the four pentyl ammonium bromide, four hexyl ammonium chlorides, four hexyl ammonium bromides, four heptyl ammonium chlorides, four heptyl ammonium bromides, four octyl group ammonium chlorides, four octyl group ammonium bromides, four nonyl ammonium chlorides, four nonyl ammonium bromides, four decyl ammonium chlorides, four decyl ammonium bromides, the undecyl trimethyl ammonium chloride, the undecyl trimethylammonium bromide, DTAC, DTAB, the tridecyl trimethyl ammonium chloride, the tridecyl trimethylammonium bromide, tetradecyl trimethyl ammonium chloride, TTAB, the pentadecyl trimethyl ammonium chloride, the pentadecyl trimethylammonium bromide, hexadecyltrimethylammonium chloride, softex kw, the hydroxyethyl trimethyl ammonium chloride, ammonium thiocyanate, ammonium chloride or ammonium bromide.
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CN101879402A (en) * 2010-05-18 2010-11-10 上海古堡实业有限公司 Method for removing sulfur dioxide in flue by using desulfurization liquor
CN101961598A (en) * 2010-09-02 2011-02-02 河北科技大学 Method for absorbing hydrogen sulfide gas by using ionic liquid
CN101745290B (en) * 2010-01-21 2012-08-22 南京大学 Mixed ionic liquid solution special for absorbing SO2 gas and preparation method thereof
CN103111264A (en) * 2013-02-16 2013-05-22 河北科技大学 Preparation method and application of ionic liquid and metal dual-modified mushroom dreg active carbon
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CN103908871A (en) * 2013-10-16 2014-07-09 泰兴电除尘设备厂有限公司 Solvent for absorbing sulfur dioxide in smoke gas flow
CN105214458A (en) * 2015-09-11 2016-01-06 河北科技大学 Absorb SO 2composite absorber and using method
CN106268317A (en) * 2016-08-30 2017-01-04 西安热工研究院有限公司 A kind of method that ionic liquid and carbamide carry out denitrating flue gas
CN106512657A (en) * 2016-12-18 2017-03-22 上海镁锶钡实业有限公司 Inorganic waste gas absorbent and method for treating inorganic waste gas in air
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Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101745290B (en) * 2010-01-21 2012-08-22 南京大学 Mixed ionic liquid solution special for absorbing SO2 gas and preparation method thereof
CN101879402A (en) * 2010-05-18 2010-11-10 上海古堡实业有限公司 Method for removing sulfur dioxide in flue by using desulfurization liquor
CN101961598A (en) * 2010-09-02 2011-02-02 河北科技大学 Method for absorbing hydrogen sulfide gas by using ionic liquid
CN103111264A (en) * 2013-02-16 2013-05-22 河北科技大学 Preparation method and application of ionic liquid and metal dual-modified mushroom dreg active carbon
CN103111333A (en) * 2013-02-16 2013-05-22 河北科技大学 Preparation method and application of ionic liquid and metal dual-modified sepiolite
CN103111333B (en) * 2013-02-16 2015-06-24 河北科技大学 Preparation method and application of ionic liquid and metal dual-modified sepiolite
CN103111264B (en) * 2013-02-16 2015-09-09 河北科技大学 The preparation method of a kind of ionic liquid and the two modification bacterium slag active carbon of metal and application
CN103908871B (en) * 2013-10-16 2016-02-03 江苏蓝电环保股份有限公司 A kind of solvent of sulfur dioxide absorption from flue gas stream
CN103908871A (en) * 2013-10-16 2014-07-09 泰兴电除尘设备厂有限公司 Solvent for absorbing sulfur dioxide in smoke gas flow
CN105214458A (en) * 2015-09-11 2016-01-06 河北科技大学 Absorb SO 2composite absorber and using method
CN106268317A (en) * 2016-08-30 2017-01-04 西安热工研究院有限公司 A kind of method that ionic liquid and carbamide carry out denitrating flue gas
CN106268317B (en) * 2016-08-30 2019-08-20 西安热工研究院有限公司 A method of denitrating flue gas is carried out with ionic liquid and urea
CN106512657A (en) * 2016-12-18 2017-03-22 上海镁锶钡实业有限公司 Inorganic waste gas absorbent and method for treating inorganic waste gas in air
CN110172365A (en) * 2019-06-14 2019-08-27 山东管理学院 The removal methods of the preparation of hydrogen sulfide absorption liquid, regeneration method and hydrogen sulfide
CN110180329A (en) * 2019-06-25 2019-08-30 中国石油大学(华东) Novel benzene series volatile organic compounds absorbent and its preparation method and application
CN110180330A (en) * 2019-06-25 2019-08-30 中国石油大学(华东) For removing the New Absorbent and its preparation method and application of sulfide in exhaust gas

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Application publication date: 20091216