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WO2017006244A1 - Liquides ioniques pour absorption de dioxyde de carbone et leur préparation - Google Patents

Liquides ioniques pour absorption de dioxyde de carbone et leur préparation Download PDF

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Publication number
WO2017006244A1
WO2017006244A1 PCT/IB2016/054021 IB2016054021W WO2017006244A1 WO 2017006244 A1 WO2017006244 A1 WO 2017006244A1 IB 2016054021 W IB2016054021 W IB 2016054021W WO 2017006244 A1 WO2017006244 A1 WO 2017006244A1
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WO
WIPO (PCT)
Prior art keywords
ionic liquid
carbon dioxide
group
dihydroxyalkyl
present disclosure
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/IB2016/054021
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English (en)
Inventor
Prathmesh Pradeep SALVI
Vivek RAJE
Parasuveera Uppara
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Reliance Industries Ltd
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Reliance Industries Ltd
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Filing date
Publication date
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Publication of WO2017006244A1 publication Critical patent/WO2017006244A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2258/00—Sources of waste gases
    • B01D2258/06—Polluted air
    • 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
    • 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
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/151—Reduction of greenhouse gas [GHG] emissions, e.g. CO2

Definitions

  • the present disclosure relates to ionic liquids for carbon dioxide absorption.
  • an ionic liquid for absorption of carbon dioxide comprises a cation derived from nitrogen containing heterocyclic compound and an anion.
  • the nitrogen containing heterocyclic compound is substituted with a dihydroxyalkyl group selected from 1 ,2-dihydroxyalkyl, and 1,3-dihydroxyalkyl.
  • the nitrogen containing heterocyclic compound is at least one selected from the group consisting of 1-methylimidazole, pyridine, 4-aminopyridine, 2-aminopyridine, 4- methylpyridine, 4-(dimethylamino)pyridine (DMAP), and l,4-diazabicyclo[2.2.2]octane (DABCO).
  • the dihydroxyalkyl group is at least one selected from the group consisting of 1,2- dihydroxypropyl, and 1,3-dihydroxypropyl.
  • the anion is at least one selected from the group consisting of hydroxyl, phosphate, carbonate, and phenoxide.
  • the process for the preparation of the ionic liquid comprises the following steps.
  • the nitrogen containing heterocyclic compound is reacted with a dihydroxyalkyl halide in at least one first fluid medium at a temperature in the range of 55 °C to 80 °C for 5 hours to 30 hours to obtain halide salt of dihydroxyalkyl substituted nitrogen containing heterocyclic compound.
  • the halide salt is reacted with at least one source of anion in at least one second fluid medium at a temperature in the range of 10 °C to 50 °C for 5 hours to 15 hours to obtain a suspension.
  • the suspension is filtered to obtain a residue and a filtrate, and the filtrate is evaporated to obtain the ionic liquid.
  • the dihydroxyalkyl halide is selected from the group consisting of 2-chloro- 1,3 -propanediol, and 3-chloro-l,2-propanediol.
  • the first fluid medium is at least one selected from the group consisting of methanol, ethanol, and toluene.
  • the second fluid medium is at least one selected from the group consisting of methanol, ethanol, propanol, acetone, and methylene chloride.
  • the source of anion is at least one compound selected from the group consisting of potassium hydroxide, tripotassium phosphate, potassium carbonate, sodium carbonate, sodium hydroxide, potassium phenoxide, and sodium phenoxide.
  • a process for absorbing carbon dioxide using the ionic liquid comprises the following steps.
  • the ionic liquid is mixed with water in the pre-determined weight ratio to obtain a first mixture.
  • the carbon dioxide gas or a gas containing carbon dioxide is purged in the first mixture at a flow rate of 0.1 liter/minute to 5 liter/minute at a temperature in the range of 0 °C to 40 °C for 20 minutes to 60 minutes to obtain a second mixture containing absorbed carbon dioxide.
  • the pre-determined weight ratio of the ionic liquid and water is in the range of 5: 1 to 1 :10.
  • the amount of carbon dioxide absorbed using the ionic liquid is in the range of 0.05 mole to 2.0 mole of carbon dioxide per mole of the ionic liquid.
  • Figure 1 illustrates ⁇ -NMR of 4-amino-l-(2,3-dihydroxypropyl)pyridinium hydroxide, [ADPPY][OH] ;
  • Figure 2 illustrates 1J C-NMR of 4-amino- 1 -(2,3-dihydroxypropyl)pyridinium hydroxide, [ADPPY][OH] DETAILED DESCRIPTION
  • the carbon dioxide (C(3 ⁇ 4) level in the atmosphere is increasing, which has instigated extensive research and development for methods aimed at reversing this condition.
  • Industries and manufacturing plants, nowadays, are employing various methods to absorb carbon dioxide from exhaust or air.
  • Use of organic solvents have certain drawbacks such as low solubility of carbon dioxide, high cost for solvent regeneration, need for use of absorption activators, and the like.
  • the present disclosure envisages a new approach for carbon dioxide absorption to mitigate the drawbacks mentioned herein above.
  • the present disclosure provides an ionic liquid comprising a cation derived from nitrogen containing heterocyclic compound and an anion.
  • the cation of the ionic liquid of present disclosure is derived from nitrogen containing heterocyclic compound, which is substituted with a dihydroxyalkyl group selected from 1 ,2-dihydroxyalkyl, and 1,3- dihydroxyalkyl.
  • the alkyl chain in the dihydroxyalkyl group of the ionic liquid of the present disclosure can be in the range of C2 to C28- The presence of the dihydroxy substituents on the alkyl group affords desirable carbon dioxide absorption properties to the ionic liquid of the present disclosure.
  • the nitrogen containing heterocyclic compound of the ionic liquid is at least one selected from the group consisting of 1-methylimidazole, pyridine, 4-aminopyridine, 2-aminopyridine, 4-methylpyridine, 4- (dimethylamino)pyridine (DMAP), and l,4-diazabicyclo[2.2.2]octane (DAB CO).
  • the nitrogen containing heterocyclic compound is 4-aminopyridine.
  • the nitrogen containing heterocyclic compound is pyridine.
  • the nitrogen containing heterocyclic compound is 1-methylimidazole.
  • the ionic liquid of the present disclosure prepared from nitrogen containing heterocyclic compound substituted with an amino group show more carbon dioxide absorption capacity as compared to the ionic liquid prepared from nitrogen containing heterocyclic compound that does not have amino group substitution.
  • the dihydroxyalkyl group of the ionic liquid is at least one selected from the group consisting of 1,2-dihydroxypropyl, and 1,3-dihydroxypropyl.
  • the dihydroxyalkyl group is 1 ,2-dihydroxypropyl.
  • the anion of the ionic liquid is at least one selected from the group consisting of hydroxyl, phosphate, carbonate, and phenoxide.
  • the anion is hydroxyl group.
  • the anion is phosphate group.
  • the choice of the cation and the anion has a large impact on the solubility of the carbon dioxide in the ionic liquid.
  • a process for the preparation of the ionic liquid comprises the following steps.
  • the nitrogen containing heterocyclic compound is reacted with a dihydroxyalkyl halide in at least one first fluid medium at a temperature in the range of 55 °C to 80 °C for 5 hours to 30 hours to obtain halide salt of dihydroxyalkyl substituted nitrogen containing heterocyclic compound.
  • the halide salt is reacted with at least one source of anion in at least one second fluid medium at a temperature in the range of 10 °C to 50 °C for 5 hours to 15 hours to obtain a suspension.
  • the suspension is filtered to obtain a residue and a filtrate.
  • the filtrate is evaporated to obtain the ionic liquid.
  • the dihydroxyalkyl halide of the present disclosure is selected from the group consisting of 2-chloro- 1,3 -propanediol, and 3-chloro-l,2-propanediol.
  • the dihydroxyalkyl halide is 3- chloro- 1 ,2-propanediol.
  • the first fluid medium is at least one selected from the group consisting of methanol, ethanol, and toluene.
  • the first fluid medium is absolute ethanol.
  • the second fluid medium of the present disclosure is at least one selected from the group consisting of methanol, ethanol, propanol, acetone, and methylene chloride.
  • the second fluid medium is methylene chloride.
  • the source of anion of the ionic liquid is at least one compound selected from the group consisting of potassium hydroxide, tripotassium phosphate, potassium carbonate, sodium carbonate, sodium hydroxide, potassium phenoxide, and sodium phenoxide.
  • the source of anion is potassium hydroxide.
  • the source of anion is tripotassium phosphate.
  • the process for preparation of the ionic liquid of the present disclosure is simple, and uses readily available chemicals or reagents. Therefore, the process for the preparation of ionic liquid of the present disclosure is economic. Further, the ionic liquid used for carbon dioxide absorption can be recycled and reused.
  • a process for absorbing carbon dioxide using the ionic liquid comprises the following steps.
  • the ionic liquid is mixed with water in the pre-determined weight ratio to obtain a first mixture.
  • the carbon dioxide gas or a gas containing carbon dioxide is purged in the first mixture at a flow rate of 0.1 liter/minute to 5 liter/minute at a temperature in the range of 0 °C to 40 °C for 20 minutes to 60 minutes to obtain a second mixture containing absorbed carbon dioxide.
  • the pre-determined weight ratio of the ionic liquid and water is in the range of 5: 1 to 1 : 10. In accordance with one embodiment of the present disclosure, the pre-determined weight ratio of the ionic liquid and water is 1: 1.
  • the amount of carbon dioxide absorbed using the ionic liquid is in the range of 0.05 mole to 2.0 mole of carbon dioxide per mole of the ionic liquid.
  • the amount of carbon dioxide absorbed using the ionic liquid is in the range of 0.20 mole to 0.80 mole of carbon dioxide per mole of the ionic liquid.
  • the amount of carbon dioxide absorbed using the ionic liquid is 0.65 mole of carbon dioxide per mole of the ionic liquid.
  • the amount of carbon dioxide absorbed using the ionic liquid is 0.40 mole of carbon dioxide per mole of the ionic liquid.
  • the amount of carbon dioxide absorbed using the ionic liquid is 0.28 mole of carbon dioxide per mole of the ionic liquid.
  • the ionic liquid of the present disclosure show excellent carbon dioxide absorption capacity using a simple process for carbon dioxide absorption.
  • Step-I Synthesis of 4-amino-l-(2,3-dihydroxypropyl)pyridinium chloride [ADPPY][C1]
  • a mixture of 4-aminopyridine (4.7 gm, 50 mmol) and 3-chloro-l,2-propanediol (4.15 mL, 50 mmol) was charged into a reactor.
  • the mixture was stirred at 68 °C for 24 hours in absolute ethanol.
  • the solvent was removed under reduced pressure to obtain a residue.
  • the residue was washed with ethyl acetate (3 x 10 mL) and dried under reduced pressure to obtain [ADPPY][C1].
  • the solubility of carbon dioxide in the ionic liquid (IL), as prepared in Step-I, was determined by applying the weight gain - loss method.
  • a pre-determined mass of [ADPPY] [OH] was loaded into an absorption vessel.
  • the viscosity of the ionic liquid was high, it was mixed with water in the weight ratio of 1 :1 for effective carbon dioxide absorption.
  • the experimental determination of the gas solubility in the liquid was based on the bubble point method. 1 gm of [ADPPY] [OH] and 1 gm of water were charged into a glass reaction vessel (open system). Carbon dioxide gas was purged by 1.5 lit/min flow rate into the reaction vessel at 25 °C for 30 minutes.
  • Tripotassium phosphate (4.24 gm, 20 mmol) and [ADPPY] [C1] (6.08 gm, 20 mmol) were introduced in methylene chloride (20 mL) followed by vigorous stirring at 25 °C for 10 hours.
  • the resultant mixture was filtered to separate precipitated KCl and the filtrate was evaporated to obtain [ADPPY] [P0 4 ] as viscous liquid product.
  • the present disclosure described herein above has several technical advantages including, but not limited to, the realization of an ionic liquid: having carbon dioxide absorption capacity in the range from 0.05 mole to 2.0 mole of carbon dioxide per mole of the ionic liquid; and that is easy to synthesize, economical, and reusable.

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

Abstract

La présente invention concerne des liquides ioniques pour l'absorption de dioxyde de carbone. La présente invention concerne un liquide ionique comprenant un cation obtenu à partir de composé hétérocyclique contenant de l'azote, et un anion. Le composé hétérocyclique contenant de l'azote est substitué par un groupe dihydroxyalkyle choisi parmi 1,2-dihydroxyalkyle et 1,3-dihydroxyalkyle. La présente invention concerne également un procédé pour la préparation du liquide ionique. Le liquide ionique selon la présente invention a une capacité d'absorption de dioxyde de carbone dans la plage de 0,05 mole à 2,0 mole de dioxyde de carbone par mole du liquide ionique.
PCT/IB2016/054021 2015-07-06 2016-07-05 Liquides ioniques pour absorption de dioxyde de carbone et leur préparation Ceased WO2017006244A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2580MU2015 2015-07-06
IN2580/MUM/2015 2015-07-06

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WO2017006244A1 true WO2017006244A1 (fr) 2017-01-12

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115193219A (zh) * 2021-04-08 2022-10-18 中国科学院物理研究所 用于吸收co2气体的溶液及co2的吸收、释放方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013147369A1 (fr) * 2012-03-29 2013-10-03 한국에너지기술연구원 Liquide ionique à base d'imidazolium pour une séparation de dioxyde de carbone, et son utilisation
CN101935311B (zh) * 2009-06-29 2015-06-10 现代自动车株式会社 哌嗪鎓三氟乙酸盐化合物和使用该物的二氧化碳吸收剂

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101935311B (zh) * 2009-06-29 2015-06-10 现代自动车株式会社 哌嗪鎓三氟乙酸盐化合物和使用该物的二氧化碳吸收剂
WO2013147369A1 (fr) * 2012-03-29 2013-10-03 한국에너지기술연구원 Liquide ionique à base d'imidazolium pour une séparation de dioxyde de carbone, et son utilisation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115193219A (zh) * 2021-04-08 2022-10-18 中国科学院物理研究所 用于吸收co2气体的溶液及co2的吸收、释放方法
CN115193219B (zh) * 2021-04-08 2024-04-05 中国科学院物理研究所 用于吸收co2气体的溶液及co2的吸收、释放方法

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