JP6195845B2 - 混合ガスからco2を吸収するための方法および吸収媒体 - Google Patents
混合ガスからco2を吸収するための方法および吸収媒体 Download PDFInfo
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- B01D53/34—Chemical or biological purification of waste gases
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- 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
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- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
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- B01D2252/20—Organic absorbents
- B01D2252/204—Amines
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- Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
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- 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
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Description
a)一般式(II)
の少なくとも1種のケトンを、水溶液中のグリシンおよび水素を用いて、固体の水素化触媒の存在下に、N−アルキルグリシンの形成下に還元的アミノ化する工程、
b)工程a)で得られた混合物から水素化触媒を分離する工程、そして
c)水酸化カリウム、炭酸カリウムまたは炭酸水素カリウムを、工程b)で得られた混合物に添加する工程
を有する本発明による吸収媒体の製造方法である。
のアミノ酸塩を5〜50質量%含んでいる。本発明による吸収媒体は、上述の通り、本発明によるCO2の吸収方法の好ましい実施態様の吸収媒体の場合に記載されている通りの組成を有しているのが好ましい。
例1
N−イソプロピルグリシンカリウムの水溶液の製造
グリシン37.52gを、水500mlおよびアセトン147mlからの混合物中に溶解させた。次に、この溶液のpH値を、85質量%の水酸化カリウム1.49gを添加して8.5の値に調節した。5質量%のパラジウム活性炭(湿分50質量%)10gを添加した後、水素を注入して6barにして、前記混合物を、6barの一定の水素圧で14時間、55℃で撹拌した。引き続き、前記触媒を真空ろ過により分離した。得られた溶液の1H−NMRスペクトルは、グリシンの反応生成物として、N−イソプロピルグリシンおよびN−ジイソプロピルグリシンを50:1のモル比で示した。前記溶液をロータリーエバポレーターで約100mlに濃縮した。その後、85質量%の水酸化カリウム31.6gを添加して、この混合物に水を注いで222gにした。
N−(sec−ブチル)グリシンカリウムの水溶液の製造
グリシン75.1gを水450ml中に溶解させて、この溶液のpH値を、85質量%の水酸化カリウム3.3gを添加して8.5の値に調節した。2−ブタノン108.2gおよび5質量%のパラジウム活性炭(湿分50質量%)7.5gを添加した後、水素を注入して5barにして、前記混合物を5barの一定の水素圧で48時間、55℃で撹拌した。引き続き、前記触媒を真空ろ過により分離した。得られた溶液の1H−NMRスペクトルは、グリシンの反応生成物として、N−sec−ブチルグリシンおよび未反応のグリシンを50:1のモル比で示した。前記溶液をロータリーエバポレーターで約200mlに濃縮した。その後、85質量%の水酸化カリウム60gを添加して、この混合物に水を注いで500gにした。
CO2の吸収容量の測定
CO2負荷およびCO2−Hubの測定のために、第1表に記載された割合のアミノ酸および水酸化カリウムを有する水性の吸収媒体150gを、3℃に冷却された還流冷却器が装着された熱安定性の容器に装入した。40℃もしくは100℃に加熱後、前記容器底のフリット(Fritte)を通して、CO2 14体積%、窒素80体積%、および酸素6体積%からの混合ガスを、流速59l/hで前記吸収媒体を通して、還流冷却器から流出するガス流中のCO2濃度を、CO2分析器を有するIR吸収により測定した。導通されたガス流中および流出したガス流中のCO2含有量の差の積分により、吸収されたCO2量を求め、CO2を有する吸収媒体の平衡負荷を算出した。CO2−Hubは、40℃および100℃で吸収されたCO2量の差として算出した。このようにして測定された40および100℃での平衡負荷(CO2 mol/吸収媒体1kg)およびCo2−Hub(CO2 mol/吸収媒体1kg)は、第1表に記載されている。
Claims (21)
- 前記吸収媒体が、一般式(I)のアミノ酸塩を10〜48質量%含んでいることを特徴とする、請求項1または2に記載の方法。
- 一般式(I)のアミノ酸塩の90質量%超が、N−イソプロピルグリシンカリウムであることを特徴とする請求項1から3までのいずれか1項に記載の方法。
- 前記吸収媒体が、水を少なくとも40質量%含んでいることを特徴とする、請求項2から4までのいずれか1項に記載の方法。
- 前記混合ガスが、燃焼排ガス、天然ガスまたはバイオガスであることを特徴とする、請求項1から5までのいずれか1項に記載の方法。
- 前記吸収媒体中に吸収されたCO2が、温度の上昇および/または圧力の低下により再び脱着されて、前記吸収媒体が、CO2の脱着後に、CO2の吸収のために再び使用されることを特徴とする、請求項1から6までのいずれか1項に記載の方法。
- 前記吸収が、0〜80℃の範囲の温度で、および前記脱着が、50〜200℃の範囲の、より高い温度で実施されることを特徴とする、請求項7に記載の方法。
- 前記吸収が、0.8〜50barの範囲の圧力で、および前記脱着が、0.01〜10barの範囲の、より低い圧力で実施されることを特徴とする、請求項7または8に記載の方法。
- 吸収および脱着の工程が、複数回繰り返されることを特徴とする、請求項7から9までのいずれか1項に記載の方法。
- 請求項2に規定される吸収媒体において、炭酸カリウムまたは炭酸水素カリウムの形態のカリウムイオンの、一般式(I)のアミノ酸塩に対するモル比が、水酸化カリウム、炭酸カリウムまたは炭酸水素カリウムの添加により、0.01〜0.1の範囲に保たれることを特徴とする、請求項10に記載の方法。
- 一般式(I)のアミノ酸塩を10〜48質量%含んでいることを特徴とする、請求項12または13に記載の吸収媒体。
- 一般式(I)のアミノ酸塩の90質量%超が、N−イソプロピルグリシンカリウムであることを特徴とする、請求項12から14までのいずれか1項に記載の吸収媒体。
- 水を40質量%超含んでいることを特徴とする、請求項12から15までのいずれか1項に記載の吸収媒体。
- 一般式(II)のケトンが、アセトンであることを特徴とする、請求項17に記載の方法。
- 工程c)において、水酸化カリウムが添加されることを特徴とする、請求項17から18のいずれか1項に記載の方法。
- 工程a)において、0〜150℃の温度、および1〜30barの水素分圧で実施されることを特徴とする、請求項17から19までのいずれか1項に記載の方法。
- 工程a)で、グリシンおよび一般式(II)のケトンの水溶液のpH値が、水素の添加前に、6〜10の範囲の値に調節されることを特徴とする、請求項17から20までのいずれか1項に記載の方法。
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DE102012200907.8 | 2012-01-23 | ||
DE102012200907A DE102012200907A1 (de) | 2012-01-23 | 2012-01-23 | Verfahren und Absorptionsmedium zur Absorption von CO2 aus einer Gasmischung |
PCT/EP2012/073778 WO2013110374A1 (de) | 2012-01-23 | 2012-11-28 | Verfahren und absorptionsmedium zur absorption von co2 aus einer gasmischung |
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JP2017213563A (ja) * | 2012-01-23 | 2017-12-07 | エボニック デグサ ゲーエムベーハーEvonik Degussa GmbH | 混合ガスからco2を吸収するための方法および吸収媒体 |
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DE102012207509A1 (de) | 2012-05-07 | 2013-11-07 | Evonik Degussa Gmbh | Verfahren zur Absorption von CO2 aus einer Gasmischung |
CN104645780B (zh) * | 2015-02-04 | 2016-06-08 | 中国华能集团清洁能源技术研究院有限公司 | 一种捕集二氧化碳的变温浓缩吸收剂及其使用方法 |
DE102015212749A1 (de) | 2015-07-08 | 2017-01-12 | Evonik Degussa Gmbh | Verfahren zur Entfeuchtung von feuchten Gasgemischen |
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US10583388B2 (en) * | 2016-06-03 | 2020-03-10 | West Virginia University | Amino acids react with carbon dioxide (CO2) and form nanofibers and nanoflowers |
DE102016210478A1 (de) | 2016-06-14 | 2017-12-14 | Evonik Degussa Gmbh | Verfahren zur Entfeuchtung von feuchten Gasgemischen |
DE102016210481B3 (de) | 2016-06-14 | 2017-06-08 | Evonik Degussa Gmbh | Verfahren zum Reinigen einer ionischen Flüssigkeit |
EP3257568B1 (de) | 2016-06-14 | 2019-09-18 | Evonik Degussa GmbH | Verfahren zur entfeuchtung von feuchten gasgemischen mit ionischen flüssigkeiten |
DE102016210484A1 (de) | 2016-06-14 | 2017-12-14 | Evonik Degussa Gmbh | Verfahren zur Entfeuchtung von feuchten Gasgemischen |
DE102016210483A1 (de) | 2016-06-14 | 2017-12-14 | Evonik Degussa Gmbh | Verfahren und Absorptionsmittel zur Entfeuchtung von feuchten Gasgemischen |
EP3257843A1 (en) | 2016-06-14 | 2017-12-20 | Evonik Degussa GmbH | Method of preparing a high purity imidazolium salt |
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DE102013212805A1 (de) | 2013-07-01 | 2015-01-08 | Evonik Industries Ag | Verwendung von hoch effizienten Arbeitsmedien für Wärmekraftmaschinen |
KR102071269B1 (ko) | 2013-07-17 | 2020-01-30 | 엔티에이치 디그리 테크놀로지스 월드와이드 인코포레이티드 | 프린트된 산화은 배터리들 |
DE102013226613A1 (de) | 2013-12-19 | 2015-06-25 | Evonik Industries Ag | Verarbeitungsfreundlicher Dianhydridhärter für Epoxidharzsysteme basierend auf 5,5'-Oxybis(isobenzofuran-1,3-dion) |
DE102013226601A1 (de) | 2013-12-19 | 2015-06-25 | Evonik Industries Ag | Verarbeitungsfreundlicher Dianhydridhärter für Epoxidharzsysteme basierend auf 5,5'-Carbonylbis(isobenzofuran-1,3-dion) |
GB2528494B (en) | 2014-07-24 | 2018-01-03 | Worn Again Footwear And Accessories Ltd | Process for extracting polyester and dyes from fabric |
DE102014214670A1 (de) | 2014-07-25 | 2016-01-28 | Evonik Degussa Gmbh | Vereinfachtes Verfahren zur Synthese von Heterozyklen |
DE102014226441A1 (de) | 2014-12-18 | 2016-06-23 | Evonik Degussa Gmbh | Verfahren zum Reinigen einer ionischen Flüssigkeit und Verfahren zum Entfeuchten von Luft |
DE102015212749A1 (de) | 2015-07-08 | 2017-01-12 | Evonik Degussa Gmbh | Verfahren zur Entfeuchtung von feuchten Gasgemischen |
DE102016210481B3 (de) | 2016-06-14 | 2017-06-08 | Evonik Degussa Gmbh | Verfahren zum Reinigen einer ionischen Flüssigkeit |
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2012
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- 2012-11-28 US US14/373,350 patent/US9878285B2/en active Active
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- 2012-11-28 EP EP12791485.1A patent/EP2806965B1/de active Active
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- 2012-11-28 JP JP2014553642A patent/JP6195845B2/ja active Active
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2017213563A (ja) * | 2012-01-23 | 2017-12-07 | エボニック デグサ ゲーエムベーハーEvonik Degussa GmbH | 混合ガスからco2を吸収するための方法および吸収媒体 |
Also Published As
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BR112014017856B1 (pt) | 2021-02-02 |
EP2806965B1 (de) | 2020-01-08 |
CN106943845A (zh) | 2017-07-14 |
DE102012200907A1 (de) | 2013-07-25 |
US20140356268A1 (en) | 2014-12-04 |
EP2806965A1 (de) | 2014-12-03 |
BR112014017856A8 (pt) | 2017-07-11 |
WO2013110374A1 (de) | 2013-08-01 |
BR112014017856A2 (ja) | 2017-06-20 |
CN104093475A (zh) | 2014-10-08 |
US9878285B2 (en) | 2018-01-30 |
JP2017213563A (ja) | 2017-12-07 |
AU2012367110A1 (en) | 2014-07-31 |
MY188201A (en) | 2021-11-24 |
AU2012367110B2 (en) | 2016-11-03 |
ZA201405412B (en) | 2020-05-27 |
JP2015512764A (ja) | 2015-04-30 |
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