CN102895844A - Liquid carbon dioxide absorbent and preparation method thereof - Google Patents
Liquid carbon dioxide absorbent and preparation method thereof Download PDFInfo
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Abstract
The invention relates to a liquid carbon dioxide absorbent and a preparation method thereof, belonging to the technical field of novel chemical materials and preparation thereof. The liquid carbon dioxide absorbent is represented by formula (I), wherein AA- is an amino acid radical, concretely is one of glycine radical, L-valine radical, DL-leucine radical, L-leucine radical, L-alanine radical, and L-serine radical. The preparation method comprises the following steps: reacting 1,8-diazabicyclo[5,4,0]undec-7-ene with amino acid in an organic solvent, removing the organic solvent from the reaction liquid by vacuum distillation to obtain the liquid carbon dioxide absorbent disclosed herein. According to the invention, the absorbent disclosed herein used for absorbing carbon dioxide has the characteristics of large absorbing amount, high stability and low regeneration energy consumption, and can be used for absorbing carbon dioxide in flue gas and natural gas.
Description
Technical field
The present invention relates to a kind of gas absorbent and preparation method thereof, be specifically related to carbon-dioxide absorbent of a kind of liquid state and preparation method thereof, belong to new type chemical material and preparing technical field thereof.
Background technology
The global warming that greenhouse effects cause is considered to one of urgent and the most serious now environmental problem.It has been generally acknowledged that now the release that the main cause of greenhouse effects is so-called greenhouse gases in the atmosphere.Wherein, topmost greenhouse gases are carbon dioxide, and it is mainly by the burning of fossil fuel such as coal, oil and natural gas and discharge.
A kind of mode of cutting down release of carbonate dioxide is absorbing carbon dioxide effectively and economically from its source.In a single day carbon dioxide is absorbed and can be completely cut off in the geology series of rocks, also can be used as the synthetic organic-fuel of raw material and chemical products.
At present, there are several different methods such as absorption and sorption and film separation etc. to be used to absorbing carbon dioxide from flue gas or natural gas.Wherein, most popular method is absorption process on the commercial scale, and the absorbent of use mainly is the alkanolamine aqueous solution, such as MEA, N methyldiethanol amine, diethanol amine and triethanolamine etc.The alkanolamine aqueous solution and carbon dioxide generation chemical bond and absorb, when applying heat to it, the chemical bond key between absorbent and the carbon dioxide is destroyed, so that carbon dioxide is desorbed, absorbent regeneration, and the absorbent of regeneration is reused for absorbing carbon dioxide.Yet, there are some shortcomings in alkanolamine aqueous solution absorbent, can cause alkanolamine that irreversible decomposition occurs such as the high temperature that is used for destroying chemical bond key between absorbent and the carbon dioxide in the absorbent regeneration process, alkanolamine itself or catabolite have certain corrosivity to absorption plant, and a large amount of decentralized medium water causes the regenerative process energy consumption very high.Therefore, be necessary the development of new carbon-dioxide absorbent.
In recent years, the ion liquid type carbon-dioxide absorbent receives people's concern.Ionic liquid is a kind of low temperature molten salt, is being lower than under 100 ℃ of conditions the liquid that is made of anion and cation fully.U.S. Patent Publication No. 6,849,774, U.S. Patent Publication No. 6,623,659 and Chinese patent application publication No. CN 101935311 A in the ion liquid type carbon-dioxide absorbent of different structure is disclosed, the characteristics such as these absorbents have the heat endurance height, volatility is low and the regeneration energy consumption is low.But these absorbents are compared with the alkanolamine absorbent, and the ability of absorbing carbon dioxide significantly reduces, and manufacturing cost is very high.
(Bates E D, Mayton R D, Ntai I, the Davis J H. CO such as Bates
2Capture by a task-specific ionic liquid. J. Am. Chem. Soc., 2002,124:926-927) disclose the ion liquid type carbon-dioxide absorbent that contains amido on a kind of cation, this absorbent carbon dioxide absorption amount at normal temperatures and pressures can reach 0.5 mol
Carbon dioxide/ mol
Absorbent, absorbability is suitable with the alkanolamine absorbent.But this absorbent synthesis technique is complicated, and behind the absorbing carbon dioxide, the viscosity of absorbent can significantly rise, and this has limited the application of its absorbing carbon dioxide in flue gas or natural gas.
The New Policy that uses ion liquid type absorbent and alkanolamine absorbent to form mixed absorbent is disclosed among Chinese patent application publication No. CN 101700454 A, Chinese patent application publication No. CN 102451597 A and Chinese patent application publication No. CN 101804292 A, this mixed absorbent has that uptake is large, infiltration rate is fast and absorb after the advantages such as viscosity amplification is little, but exist the alkanolamine volatility to reach greatly the problems such as circulation ability is poor.
(Zhang J M, Zhang S J, Dong K, Zhang Y Q, Shen Y Q, the Lu X M. Supported absorption of CO such as Zhang
2By tcetrabutylphosphonium amino acid ionic liquids. Chem. Eur. J., 2006,12:4021-4026) He among Chinese patent application publication No. CN 102008870 A disclose amino acid ion liquid type carbon-dioxide absorbent, carbon dioxide absorption amount at normal temperatures and pressures can be near 0.5 mol
Carbon dioxide/ mol
Absorbent, absorbability is suitable with the alkanolamine absorbent, and equipment is not had corrosivity, also non-volatile loss of absorbent consistency in the process of absorption-Desorption of Carbon Dioxide repeatedly.This class absorbent has higher viscosity, and this has limited the application of its absorbing carbon dioxide in flue gas or natural gas.
For the problem that carbon-dioxide absorbent exists, develop that a kind of uptake is large, stability is high, viscosity is low and the low ion liquid type carbon-dioxide absorbent of regeneration energy consumption is very necessary.
Summary of the invention
The technical problem to be solved in the present invention provides a kind of carbon-dioxide absorbent of liquid state, described carbon-dioxide absorbent has large, the stable height of uptake, viscosity is hanged down and reached the characteristics such as the regeneration energy consumption is low, is particularly suitable for the carbon dioxide in absorption from flue gas or the natural gas; The present invention provides the preparation method of this class absorbent simultaneously for this reason.
For solving the problems of the technologies described above, the technical solution used in the present invention is:
The invention provides a kind of carbon-dioxide absorbent of liquid state, its structural formula is as follows:
Wherein, AA
_Be amino acid group, it is specially one of following: glycine root, Valine root, DL-leucine root, L-Leu root, ALANINE root, Serine root.
The present invention also provides the preparation method of the carbon-dioxide absorbent of above-mentioned liquid state, and it is concrete
Step is as follows: with 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene is added drop-wise in the reaction bulb that amino acid and organic solvent are housed, the control rate of addition, make that temperature is lower than 10 ℃ in the reaction bulb, dropwise, rising temperature to 30 ~ 35 ℃, stirring reaction 10 ~ 12 hours, decompression distillation eliminates organic solvent, and cool to room temperature namely gets described absorbent.
The carbon dioxide absorption of liquid state provided by the invention specifically mainly contains: glycineization 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene carbon-dioxide absorbent, Valineization 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene carbon-dioxide absorbent, DL-leucineization 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene carbon-dioxide absorbent, L-Leuization 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene carbon-dioxide absorbent, ALANINEization 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene carbon-dioxide absorbent and Serineization 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene carbon-dioxide absorbent.
The carbon-dioxide absorbent of liquid state provided by the invention can be under the condition of 40 ~ 50 ℃ of temperature, pressure 0.1 ~ 1.0 MPa carbon dioxide in absorption from flue gas or the natural gas, uptake is the highest under 0.1 MPa condition can reach 0.74 mol
Carbon dioxide/ mol
AbsorbentForm with a phase behind the described absorbent absorbing carbon dioxide exists, and namely carbon dioxide is absorbed into the separation that does not produce solids of sedimentation or second liquid phase in the described absorbent.Described absorbent maintains lower viscosity in whole absorption process, this is conducive to the carrying out of carbon dioxide absorption and desorption process, and under the condition of 40 ℃ and 0.1 MPa, the peak of viscosity is 75 mPaS during described absorbent saturated absorption.In addition, described absorbent absorbing carbon dioxide is very fast, and its infiltration rate is suitable with alkanolamine aqueous solution absorbent.
The carbon-dioxide absorbent of liquid state provided by the invention can carry out desorb by the mode that passes into nitrogen to the carbon dioxide that absorbs after absorption is saturated, make absorbent regeneration.The temperature of desorption and regeneration is between 60 ~ 70 ℃, and the pressure of desorption and regeneration is between 0.01 ~ 0.1 MPa, and desorption efficiency is higher than 95%, and the absorbent after the desorb can be reused for absorbing carbon dioxide, and circulating, uptake does not reduce after 10 times.
Carbon-dioxide absorbent of liquid state provided by the invention and preparation method thereof compared with prior art has following remarkable result:
1, the present invention is to provide the novel liquid carbon dioxide absorbent of a class, developed the new varieties of carbon-dioxide absorbent.
2, the carbon-dioxide absorbent volatility of liquid state provided by the invention is very low, and repeatedly the rear uptake of circulation does not reduce, and has high stability.
3, the carbon-dioxide absorbent of liquid state provided by the invention has large uptake and lower viscosity.
4, the carbon-dioxide absorbent of liquid state provided by the invention is by passing into the nitrogen desorb, and the regeneration energy consumption is low.
5, the raw materials of the carbon-dioxide absorbent of liquid state provided by the invention more easily obtains, and is cheap, has low preparation cost.
6, the carbon-dioxide absorbent preparation method of liquid state provided by the invention is easy, and equipment needed thereby is simple, and suitable for mass production is used.
Description of drawings
Fig. 1 shows the schematic diagram that the present invention measures the equipment of carbon dioxide absorption/desorption ability.
The specific embodiment
The present invention illustrates by following examples, but the present invention is not limited to following embodiment, and under the scope of described aim, change is included in the technical scope of the present invention before and after not breaking away from.
Embodiment 1
37.54 g(0.50 mol will be housed) reaction bulb of glycine and 50 milliliters of acetone places ice-water bath, in reaction bulb, drip 76.12 g(0.50 mol) 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene, the control rate of addition, make the interior temperature of reaction bulb be lower than 10 ℃, dropwise, rising temperature to 35 ℃, stirring reaction 12 hours, decompression distillation eliminates acetone, cool to room temperature (25 ℃), colourless transparent liquid, be glycineization 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene carbon-dioxide absorbent, productive rate is 98%, and structural formula is as follows:
58.58 g(0.50 mol will be housed) reaction bulb of Valine and 50 milliliters of acetone places ice-water bath, in reaction bulb, drip 76.12 g(0.50 mol) 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene, the control rate of addition, make the interior temperature of reaction bulb be lower than 10 ℃, dropwise, rising temperature to 35 ℃, stirring reaction 10 hours, decompression distillation eliminates acetone, cool to room temperature (25 ℃), light yellow transparent liquid, be Valineization 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene carbon-dioxide absorbent, productive rate is 97%, and structural formula is as follows:
Embodiment 3
65.85 g(0.50 mol will be housed) reaction bulb of DL-leucine and 100 milliliters of oxolanes places ice-water bath, in reaction bulb, drip 76.12 g(0.50 mol) 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene, the control rate of addition, make the interior temperature of reaction bulb be lower than 10 ℃, dropwise, rising temperature to 35 ℃, stirring reaction 12 hours, decompression distillation eliminates oxolane, cool to room temperature (25 ℃), light yellow transparent liquid, be DL-leucineization 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene carbon-dioxide absorbent, productive rate is 95%, and structural formula is as follows:
73.10 g(0.50 mol will be housed) reaction bulb of L-Leu and 100 milliliters of oxolanes places ice-water bath, in reaction bulb, drip 76.12 g(0.50 mol) 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene, the control rate of addition, make the interior temperature of reaction bulb be lower than 10 ℃, dropwise, rising temperature to 30 ℃, stirring reaction 12 hours, decompression distillation eliminates oxolane, cool to room temperature (25 ℃), light yellow transparent liquid, be L-Leuization 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene carbon-dioxide absorbent, productive rate is 96%, and structural formula is as follows:
Embodiment 5
44.55 g(0.50 mol will be housed) reaction bulb of ALANINE and 50 milliliters of acetone places ice-water bath, in reaction bulb, drip 76.12 g(0.50 mol) 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene, the control rate of addition, make the interior temperature of reaction bulb be lower than 10 ℃, dropwise, rising temperature to 30 ℃, stirring reaction 12 hours, decompression distillation eliminates acetone, cool to room temperature (25 ℃), light yellow transparent liquid, be ALANINEization 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene carbon-dioxide absorbent, productive rate is 98%, and structural formula is as follows:
52.55 g(0.50 mol will be housed) reaction bulb of Serine and 50 milliliters of acetone places ice-water bath, in reaction bulb, drip 76.12 g(0.50 mol) 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene, the control rate of addition, make the interior temperature of reaction bulb be lower than 10 ℃, dropwise, rising temperature to 35 ℃, stirring reaction 12 hours, decompression distillation eliminates acetone, cool to room temperature (25 ℃), light yellow transparent liquid, be Serineization 1,8-diazabicylo [5. 4. 0] 11 carbon-7-alkene carbon-dioxide absorbent, productive rate is 97%, and structural formula is as follows:
Test implementation example 1
Fig. 1 schematically shows for the equipment of measuring carbon dioxide absorption/desorption ability.The said equipment comprises: high-pressure carbon dioxide air accumulator 1, high pressure nitrogen air accumulator 2, mass flow controller 3, mixed gas tank 4, Pressure gauge 5, triple valve 6, absorption-desorb reactor 7, balance 8, thermometer 9, holding furnace 10 and infrared flue gas analyzer 11.
Carry out in the following way carbon dioxide absorption/desorption ability test:
At first, utilize nitrogen (nitrogen gas purity is higher than 99.99%) to purge successively main road and bypath system, residual air in the system is removed clean;
Rotate triple valve, keep the bypass opening state, certain a kind of carbon-dioxide absorbent of (with 100 milliliters of stainless steel reaction tanks of thermometer) injection is weighed in absorptions-desorb reactor embodiment 1 to embodiment 6;
Absorption-desorb reactor is installed in the holding furnace (OF-22 of Jeiotech company type, 25 ~ 180 ℃ of heat-preserving ranges, precision ± 0.1 ℃), to keep certain temperature;
Holding temperature is set, reached behind the design temperature constant temperature 2 hours;
Require mass flow controller (Kofloc company 8500 types according to simulated flue gas concentration and volume flow rate, control range 2% ~ 100%, precision ± 1.5%FS) arrange, nitrogen is fully mixed in mixed gas tank with carbon dioxide, the preparation simulated flue gas is treated (Photon of Madur company type, measurement category 0 ~ 50% in the infrared flue gas analyzer, resolution ratio 0.01%) after gas concentration lwevel is stablized, triple valve is turned to the main road opening state;
Carry out the carbon dioxide absorption aptitude tests, monitoring absorption-desorb reactor weight change (BAS124S-CW of Sartorius company type electronic balance, range of weighing 0 ~ 500 g, precision ± 0.01 g);
The absorbability test finishes after constant weight;
Triple valve is turned to the bypass opening state;
Close high-pressure carbon dioxide air accumulator (carbon dioxide purity is higher than 99.99%), only open nitrogen, purge whole bypath system, treat that infrared flue gas analyzer shows that gas concentration lwevel is in the exit gas at 0 o'clock, nitrogen is switched to the main road system, as the desorb source of the gas;
Desorption temperature is set, reached behind the design temperature constant temperature 2 hours;
Carry out the desorption ability test, monitoring absorption-desorb reactor weight change;
The desorption ability test finishes after constant weight;
Repeat above operation and finish repeatedly absorption-desorption cycle.
Test implementation example 2
Utilize the carbon dioxide absorption/desorption ability of the carbon-dioxide absorbent of the liquid state that testing of equipment embodiment 1 to embodiment 6 shown in Figure 1 provides.
The absorbability test condition: 50 milliliters of absorbent consumptions, absorption pressure 0.1 MPa absorbs 40 ℃ and 50 ℃ of temperature, carbon dioxide volumetric concentration 10% in the simulated flue gas, simulated flue gas volume flow rate 500 ml/min.
Desorption ability test condition: desorption pressures 0.1 MPa, 70 ℃ of desorption temperatures, stripping gas volume source flow rate 500 ml/min.
In the above-mentioned test, being defined as from beginning to absorption-desorb reactor, soak time passes into simulated flue gas to the used time of absorption-desorb reactor constant weight; Desorption time is defined as from beginning to the absorption of saturated absorption-pass into the desorb source of the gas to the used time of absorption-desorb reactor constant weight the desorb reactor; The ratio of the total carbon dioxide volume that the difference that desorption efficiency is defined as amount of carbon dioxide residual after total carbon dioxide volume that absorbent absorbs and the desorb and absorbent absorb; Soak time and desorption time use the SEIKO Seiko S143 of company type stopwatch record, precision ± 0.01 second; Viscosity is used the Fei Kete NDJ-7 of company type rotary viscosity design determining, 75 rev/mins of rotating speeds, measurement category 1 ~ 10
6MPaS, precision ± 2%.Test result is recorded in the table 1.
Table 1
Claims (13)
1. the carbon-dioxide absorbent of a liquid state is characterized in that, the change of described absorbent
Formula is suc as formula shown in (I):
AA
_Be amino acid group, it is specially one of following: glycine root, Valine root, DL-leucine root, L-Leu root, ALANINE root, Serine root.
2. the preparation method of the carbon-dioxide absorbent of liquid state as claimed in claim 1, it is characterized in that, 1,8-diazabicylo [5. 4. 0], 11 carbon-7-alkene is added drop-wise in the reaction bulb that amino acid and organic solvent are housed, the control rate of addition, make that temperature is lower than 10 ℃ in the reaction bulb, dropwise, rising temperature to 30 ~ 35 ℃, stirring reaction 10 ~ 12 hours, decompression distillation eliminates organic solvent, and cool to room temperature namely gets described absorbent.
3. the preparation method of the carbon-dioxide absorbent of liquid state as claimed in claim 2 is characterized in that, and is described 1, and 8-diazabicylo [5. 4. 0] 11 carbon-7-alkene and amino acid whose mol ratio are 1:1.
4. the preparation method of the carbon-dioxide absorbent of liquid state as claimed in claim 2 is characterized in that, described dropping process is to carry out in ice-water bath, with temperature in the control reaction bulb.
5. the preparation method of the carbon-dioxide absorbent of liquid state as claimed in claim 2 is characterized in that, described amino acid is selected from one of glycine, Valine, DL-leucine, L-Leu, ALANINE and Serine.
6. the preparation method of the carbon-dioxide absorbent of liquid state as claimed in claim 2 is characterized in that, described organic solvent is selected from acetone or oxolane.
7. such as the preparation method of the carbon-dioxide absorbent of the described liquid state of claim 1 to 6, it is characterized in that described absorbent exists with the form of a phase behind absorbing carbon dioxide.
8. such as the preparation method of the carbon-dioxide absorbent of the described liquid state of claim 1 to 6, it is characterized in that the temperature of described absorbent absorbing carbon dioxide is between 40 ~ 50 ℃.
9. such as the preparation method of the carbon-dioxide absorbent of the described liquid state of claim 1 to 6, it is characterized in that the pressure of described absorbent absorbing carbon dioxide is between 0.1 ~ 1.0 MPa.
10. such as the preparation method of the carbon-dioxide absorbent of the described liquid state of claim 1 to 9, it is characterized in that the carbon dioxide that described absorbent absorbs makes absorbent regeneration by passing into the nitrogen desorb, and the absorbent of regeneration is reused for absorbing carbon dioxide.
11. the preparation method of the carbon-dioxide absorbent of liquid state as claimed in claim 10 is characterized in that making absorbent regeneration by passing into nitrogen, the purity of described nitrogen is higher than 99.99%.
12. the preparation method of the carbon-dioxide absorbent of liquid state as claimed in claim 10 is characterized in that making absorbent regeneration by passing into nitrogen, the temperature of described absorbent regeneration is between 60 ~ 70 ℃.
13. the preparation method of the carbon-dioxide absorbent of liquid state as claimed in claim 10 is characterized in that making absorbent regeneration by passing into nitrogen, the pressure of described absorbent regeneration is between 0.01 ~ 0.1 MPa.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103933830A (en) * | 2014-02-12 | 2014-07-23 | 南昌航空大学 | CO2 trapping agent and preparation method thereof |
| CN106422994A (en) * | 2016-10-21 | 2017-02-22 | 北京沃特尔水技术股份有限公司 | Method and device for preparing ammonium carbonate extraction solution |
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| CN101745289A (en) * | 2008-12-12 | 2010-06-23 | 南化集团研究院 | Method for selectively removing H2S from gas mixture containing CO2 |
| CN101804292A (en) * | 2010-03-25 | 2010-08-18 | 南京大学 | Special MDEA formula solution activated by functional ion liquid for CO2 gas absorption separation |
| CN102451597A (en) * | 2010-10-22 | 2012-05-16 | 中国石油化工集团公司 | Ion liquid solution for collecting carbon dioxide |
| CN102574050A (en) * | 2009-07-29 | 2012-07-11 | 联邦科学及工业研究组织 | Ionic liquids |
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| CN1709553A (en) * | 2005-06-02 | 2005-12-21 | 中国科学院过程工程研究所 | Amino acid ion liquid for acidic gas absorption |
| CN101745289A (en) * | 2008-12-12 | 2010-06-23 | 南化集团研究院 | Method for selectively removing H2S from gas mixture containing CO2 |
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| CN101700454A (en) * | 2009-11-25 | 2010-05-05 | 南京大学 | Green carbon dioxide absorbent |
| CN101804292A (en) * | 2010-03-25 | 2010-08-18 | 南京大学 | Special MDEA formula solution activated by functional ion liquid for CO2 gas absorption separation |
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| CN103933830A (en) * | 2014-02-12 | 2014-07-23 | 南昌航空大学 | CO2 trapping agent and preparation method thereof |
| CN106422994A (en) * | 2016-10-21 | 2017-02-22 | 北京沃特尔水技术股份有限公司 | Method and device for preparing ammonium carbonate extraction solution |
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Application publication date: 20130130 |