WO2012093853A2 - Absorbeur de dioxyde de carbone non aqueux contenant une alcanolamine secondaire et un diol dans lequel un encombrement stérique est introduit - Google Patents

Absorbeur de dioxyde de carbone non aqueux contenant une alcanolamine secondaire et un diol dans lequel un encombrement stérique est introduit Download PDF

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Publication number
WO2012093853A2
WO2012093853A2 PCT/KR2012/000088 KR2012000088W WO2012093853A2 WO 2012093853 A2 WO2012093853 A2 WO 2012093853A2 KR 2012000088 W KR2012000088 W KR 2012000088W WO 2012093853 A2 WO2012093853 A2 WO 2012093853A2
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WO
WIPO (PCT)
Prior art keywords
amino
diol
carbon dioxide
glycol
absorption
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PCT/KR2012/000088
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English (en)
Korean (ko)
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WO2012093853A3 (fr
Inventor
김훈식
정민석
임진규
홍성윤
최영섭
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경희대학교 산학협력단
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Publication of WO2012093853A3 publication Critical patent/WO2012093853A3/fr

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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
    • B01D53/1475—Removing carbon dioxide
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • 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
    • 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
    • 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
    • B01D53/34—Chemical or biological purification of waste gases
    • B01D53/46—Removing components of defined structure
    • B01D53/62—Carbon oxides
    • 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
    • B01D2252/20—Organic absorbents
    • B01D2252/202—Alcohols or their derivatives
    • 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
    • B01D2252/20—Organic absorbents
    • B01D2252/204—Amines
    • B01D2252/20426—Secondary amines
    • 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
    • B01D2252/40—Absorbents explicitly excluding the presence of water
    • 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
    • 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
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/20—Air quality improvement or preservation, e.g. vehicle emission control or emission reduction by using catalytic converters
    • 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
    • Y02C20/40—Capture or disposal of greenhouse gases of CO2

Definitions

  • the present invention relates to a non-aqueous carbon dioxide absorbent comprising secondary alkanolamines and diols in which steric hindrance is introduced. More specifically, the present invention relates to a non-aqueous carbon dioxide absorbent comprising secondary alkanolamine and diol having introduced steric hindrance, which has excellent carbon dioxide absorbing ability and very little energy consumption for absorbent regeneration.
  • Absorption, adsorption, separation membrane, deep cooling, etc. are used to separate CO 2 from the exhaust gas and natural gas of chemical plants, power plants, and large boilers.
  • absorption or adsorption methods are often used.
  • Absorption or adsorption methods are widely used because it can selectively separate only some of the gas absorbed or adsorbed to the adsorbent or adsorbent, but there is a disadvantage that the periodic replacement is necessary because the adsorbent and the adsorbent is chemically modified during the separation process. Therefore, when the solid adsorbent is used, it is advantageous to apply it only when the adsorbent replacement cycle is long due to the small chemical deformation of the adsorbent.
  • the absorbent method uses a liquid absorbent, so it is easy to replace the absorbent and has a larger absorption capacity than the adsorbent.
  • the absorbent is chemically or thermally modified.
  • amines such as monoethanolamine (MEA), N-methyldiethanolamine (MDEA), and diethanolamine (DEA) are most widely used. If the alkanolamine absorbent forms a chemical bond with CO 2 and then heats it, the bond is broken and CO 2 is removed and recovered, and the absorbent can be regenerated. However, this process has some serious problems, especially the decomposition of amines by impurities such as SOx and NOx contained in absorbent gases and the high temperatures used to break the chemical bond between CO 2 and the absorbent during the regeneration of the absorbent.
  • impurities such as SOx and NOx contained in absorbent gases
  • Low CO 2 absorption capacity organic solvents typically exhibits a much lower CO 2 absorption capacity compared to the amine solution and a high circulation rate of the absorbent is therefore required a larger equipment.
  • High circulation rate The physical absorption process by organic solvents usually requires twice as much absorbent circulation rate as in the case of amine solutions, which requires more capital and equipment costs.
  • Ionic liquids that maintain the liquid phase as absorbents.
  • Ionic liquids are polar salt compounds composed of organic cations and organic or inorganic anions and have a property of dissolving gas molecules such as CO, CO 2 , SO 2 , and N 2 O well.
  • the solubility of the gas absorbed by the ionic liquid depends on the degree of interaction between the gas and the ionic liquid.
  • the polarity, acidity and basicity of the ionic liquid are properly modified by modifying the cations and anions of the ionic liquid.
  • the solubility in a particular gas can be controlled to some extent.
  • Representative ionic liquids include nitrogen containing organic cations such as quaternary ammonium, such as imidazolium, pyrazolium, triazium, pyridinium, pyridazinium, pyrimidinium and Cl - , Br - , I - Such as halogen, BF 4 - , PF 6 - , (CF 3 SO 2 ) 2 N - , CF 3 SO 3 - , MeSO 3 - , NO 3 - , CF 3 CO 2 - , CH 3 CO 2 -
  • Compounds composed of anions such as these are known, and in particular, when anions contain fluorine atoms, they have been reported to have relatively high carbon dioxide absorption ability. However, these ionic liquid absorbers also have CO 2 There is a problem that the economic efficiency is low because the absorption capacity is significantly low and the manufacturing cost is too high.
  • ionic liquids have relatively high solubility in acidic gases such as carbon dioxide and carbon disulfide, in order to synthesize these ionic liquids, the ionic liquids usually require two or more complex manufacturing processes, and the manufacturing cost is too high. There are many problems to use.
  • the present inventors have studied diligently to solve the problems of the conventional carbon dioxide absorbent, and as a result, when using a carbon dioxide absorbent containing a secondary alkanolamine and diol introduced steric hindrance, it is possible to drastically lower the regeneration temperature of the absorbent Not only can the energy consumption be greatly reduced, but the absorption performance is increased compared to the conventional alkanolamine aqueous solution absorbent, and as the regeneration temperature is lowered, the corrosiveness is reduced and the solvent loss during regeneration can be greatly reduced.
  • the invention was completed.
  • the present invention relates to a carbon dioxide absorbent comprising a secondary alkanolamine represented by the following formula (1) and a diol represented by the formula (2) or (3).
  • R 1 , R 2 and R 3 are each independently an alkyl group of C 1 to C 4 ,
  • R 4 , R 5 and R 6 are each independently hydrogen or an alkyl group of C 1 to C 4 ,
  • R 7 is hydrogen or an alkyl group of C 1 to C 4 ,
  • n 2 to 8
  • n is an integer of 2-8.
  • an alkyl group of C 1 to C 4 means a straight or branched hydrocarbon having 1 to 4 carbon atoms, for example methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl t-butyl, and the like, but is not limited thereto.
  • Secondary alkanolamine represented by the formula (1) is, for example, 1-[(1,1-dimethylethyl) amino] -2-propanol, 2-[(1,1-dimethylethyl) amino] ethanol, 2 -[(1,1-dimethylpropyl) amino] ethanol, 1-[(1,1-dimethylpropyl) amino] -2-propanol, 2-[(1,1,2-trimethylbutyl) amino] ethanol, 1 -[(1,1,2-trimethylbutyl) amino] -2-propanol, 1-[(1,1-dimethylethyl) amino] -2-butanol, 1-[(1,1-dimethylpropyl) amino] -2-methyl-2-propanol, 1-[(1,1-dimethylethyl) amino] -2-methyl-2-propanol, 3-[(1,1-dimethylethyl) amino] -2-butanol, 1 -[(1,1-di
  • the diol represented by the formula (2) is, for example, ethane-1,2-diol (ethylene glycol), propane-1,2-diol (propylene glycol), propane-1,3-diol, butane-1,2- Diol, butane-1,3-diol, butane-1,4-diol, pentane-1,3-diol, pentane-1,5-diol, 2-ethyl-hexane-1,3-diol, octane-1, 8-diol and the like, but not limited thereto.
  • the diol represented by the formula (3) is, for example, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, tetraethylene glycol, tetrapropylene glycol, pentaethylene glycol, pentapropylene glycol, hexaethylene glycol, hexapropylene Glycols, octaethylene glycols, and the like.
  • the amount of the secondary alkanolamine is preferably 5 to 60% by weight, more preferably 20 to 40% by weight. If the amount of the secondary alkanolamine is less than 5% by weight, the CO 2 absorption capacity is significantly lowered. If the amount of the secondary alkanolamine is more than 60% by weight, the increase in the amount of CO 2 absorption is slight, but the viscosity of the absorbent liquid is too high. have.
  • the carbon dioxide absorbent according to the present invention is a non-aqueous absorbent in which a secondary alkanolamine having a steric hindrance introduced therein is dissolved in diol, and a conventional alkanolamine (for example, monoethanolamine) is shown in Scheme 1 below.
  • a conventional alkanolamine for example, monoethanolamine
  • the nitrogen atom of the amine group and CO 2 react to form a carbamate having a high thermal stability
  • the secondary alkanolamine introducing a steric hindrance according to the present invention is a hydroxy group as shown in Scheme 2 below. Oxygen atoms of and CO 2 reacts to form carbonate that is less thermally stable than carbamate.
  • the use of the absorbent of the present invention enables regeneration of the absorbent even at a low temperature, thereby reducing the energy of the overall absorption process, and greatly reducing the problems of corrosion and absorbent loss derived from the high regeneration temperature.
  • diol having a high boiling point and a low heat capacity is used as a solvent instead of water having a large latent heat of evaporation, it is much more energy-efficient than conventional alkanolamine-based absorbents using water as a solvent and dehydration of recovered CO 2 There is also an advantage that does not require a process.
  • the diol serves to stabilize the carbonate formed through the hydroxyl group as well as the solvent.
  • the present invention relates to a method for separating carbon dioxide from a gas mixture using the carbon dioxide absorbent according to the present invention, the separation method of the present invention
  • the preferred temperature is in the range of 0 ° C to 80 ° C, more preferably in the range of 20 ° C to 50 ° C, and the preferred pressure is in the range of atmospheric pressure to 50 atmospheres, more preferably at atmospheric pressure to 40 atmospheres. Range.
  • the lower the temperature and the higher the pressure the higher the amount of carbon dioxide absorption.
  • the preferred temperature is in the range from 40 ° C. to 100 ° C., more preferably in the range from 50 ° C. to 80 ° C., and the preferred pressure is from atmospheric pressure to 10 atmospheres, more preferably atmospheric pressure.
  • an exhaust gas of a chemical plant, a power plant, a large boiler, natural gas, or the like may be used.
  • Non-aqueous carbon dioxide absorbents including secondary alkanolamines and diols incorporating steric hindrance according to the present invention show superior absorption and fast absorption rates as compared with those based on conventional alkanolamine-based aqueous solutions.
  • the absorbent regeneration temperature is significantly lower, and thus, the total energy consumption required for the absorption process can be greatly reduced, and the recovered CO 2 can be prevented from being contaminated with moisture and absorbent vapor.
  • the absorbent of the present invention can maintain almost the initial absorption capacity even when repeated absorption and degassing can be used as an effective CO 2 separation medium.
  • the device of FIG. 1 is a 60 mL stainless steel absorption reactor (R1) with a thermometer (T2) attached, a pressure transducer (P1) for high pressure (0 to 70 atmospheres), 75 mL with a thermometer (T1) attached. It consists of a cylinder for storing CO 2 (S2) and a stirrer (1), it is installed in a thermostat to measure the CO 2 absorption capacity at a constant temperature. In addition, a CO 2 supply container S1 and a pressure gauge P2 were installed outside the thermostat.
  • valve (V4) close the valve (V4), raise the temperature of the absorption reactor (R1) to 60 ⁇ 100 °C, open the valve (V4), valve (V5) and valve (V6), and 20 mL / min nitrogen CO 2 was stripped off while feeding to the absorption reactor (R1).
  • the CO 2 absorption experiment was carried out in the same manner as in Example 1 while fixing the absorption temperature at 40 ° C., the absorption pressure at 1 atm, and changing the secondary alkanolamine. After one run, the amount of CO 2 absorption was measured, and the valve (V5) was opened to lower the pressure to atmospheric pressure and stripped at 80 ° C., and the nitrogen flow rate was fixed at 20 mL / min.
  • V5 the valve
  • the absorption and degassing of the first CO 2 is completed, absorption and degassing are repeated five times under the same conditions, and the initial CO 2 absorption amount and the fifth CO 2 absorption amount are shown in Table 6 below.
  • the absorption temperature was fixed at 40 DEG C, the absorption pressure at 1 atm, and 1-[(1,1-dimethylethyl) amino] -2-propanol was used as the secondary alkanolamine, while changing the stripping temperature.
  • CO 2 absorption and stripping experiments were carried out in the same manner as shown in Table 7 below.

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  • Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Biomedical Technology (AREA)
  • Environmental & Geological Engineering (AREA)
  • Gas Separation By Absorption (AREA)
  • Treating Waste Gases (AREA)

Abstract

Cette invention concerne un absorbeur de dioxyde de carbone non aqueux contenant une alcanolamine secondaire et un diol dans lequel un encombrement stérique est introduit. L'absorbeur de dioxyde de carbone selon l'invention manifeste une excellente force d'absorption et une vitesse d'absorption rapide comparativement à un absorbeur à base d'une solution d'alcanolamine classique. De plus, une température de régénération d'absorbeur est remarquablement abaissée comparativement à un absorbeur classique. Par conséquent, toute la consommation d'énergie requise pour une étape d'absorption est largement réduite et la contamination du CO2 récupéré provoquée par l'humidité et la vapeur de l'absorbeur est évitée.
PCT/KR2012/000088 2011-01-04 2012-01-04 Absorbeur de dioxyde de carbone non aqueux contenant une alcanolamine secondaire et un diol dans lequel un encombrement stérique est introduit WO2012093853A2 (fr)

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KR10-2011-0000626 2011-01-04
KR1020110000626A KR101193087B1 (ko) 2011-01-04 2011-01-04 입체장애가 도입된 2급 알칸올아민과 디올을 포함하는 비수계 이산화탄소 흡수제

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9579602B2 (en) 2015-02-26 2017-02-28 University Of Wyoming Catalytic CO2 desorption for ethanolamine based CO2 capture technologies
KR20170034587A (ko) 2015-09-21 2017-03-29 경희대학교 산학협력단 이산화탄소 흡수제
CN107427759A (zh) * 2015-03-26 2017-12-01 新日铁住金株式会社 用于分离和捕集二氧化碳的吸收液以及使用所述吸收液分离和捕集二氧化碳的方法
CN113101786A (zh) * 2021-05-10 2021-07-13 浙江浙能技术研究院有限公司 一种基于有机溶剂吸收-萃取再生循环的烟气二氧化碳捕集系统及方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101588244B1 (ko) * 2014-10-16 2016-01-25 경희대학교 산학협력단 함산소디아민을 포함하는 이산화탄소 흡수제

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US6270739B1 (en) * 2000-06-16 2001-08-07 Eastman Chemical Company Process for the removal of carbon dioxide from 3,4-epoxy-1-butene process recycle streams
US6436174B1 (en) * 1998-06-29 2002-08-20 Basf Aktiengesellschaft Method for removing acid gas components from gases
US20070148069A1 (en) * 2005-12-23 2007-06-28 Shrikar Chakravarti Carbon dioxide recovery from flue gas and the like
US20080293976A1 (en) * 2006-08-10 2008-11-27 Olah George A Nano-structure supported solid regenerative polyamine and polyamine polyol absorbents for the separation of carbon dioxide from gas mixtures including the air

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Publication number Priority date Publication date Assignee Title
US6436174B1 (en) * 1998-06-29 2002-08-20 Basf Aktiengesellschaft Method for removing acid gas components from gases
US6270739B1 (en) * 2000-06-16 2001-08-07 Eastman Chemical Company Process for the removal of carbon dioxide from 3,4-epoxy-1-butene process recycle streams
US20070148069A1 (en) * 2005-12-23 2007-06-28 Shrikar Chakravarti Carbon dioxide recovery from flue gas and the like
US20080293976A1 (en) * 2006-08-10 2008-11-27 Olah George A Nano-structure supported solid regenerative polyamine and polyamine polyol absorbents for the separation of carbon dioxide from gas mixtures including the air

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9579602B2 (en) 2015-02-26 2017-02-28 University Of Wyoming Catalytic CO2 desorption for ethanolamine based CO2 capture technologies
CN107427759A (zh) * 2015-03-26 2017-12-01 新日铁住金株式会社 用于分离和捕集二氧化碳的吸收液以及使用所述吸收液分离和捕集二氧化碳的方法
EP3275526A4 (fr) * 2015-03-26 2018-12-12 Nippon Steel & Sumitomo Metal Corporation Solution absorbante pour séparer et récupérer du dioxyde de carbone, et pour séparer et récupérer du dioxyde de carbone dans lequel cette dernière est utilisée
US10717038B2 (en) 2015-03-26 2020-07-21 Research Institute Of Innovative Technology For The Earth Absorbing solution for separating and capturing carbon dioxide, and method for separating and capturing carbon dioxide in which same is used
KR20170034587A (ko) 2015-09-21 2017-03-29 경희대학교 산학협력단 이산화탄소 흡수제
US10543454B2 (en) 2015-09-21 2020-01-28 University-Industry Cooperation Group Of Kyung Hee University Carbon dioxide absorbent
CN113101786A (zh) * 2021-05-10 2021-07-13 浙江浙能技术研究院有限公司 一种基于有机溶剂吸收-萃取再生循环的烟气二氧化碳捕集系统及方法
CN113101786B (zh) * 2021-05-10 2022-06-28 浙江浙能技术研究院有限公司 一种基于有机溶剂吸收-萃取再生循环的烟气二氧化碳捕集系统及方法

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KR20120079382A (ko) 2012-07-12
WO2012093853A3 (fr) 2012-09-27

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