WO2013050242A1 - Sorbant pour pompes à chaleur à absorption - Google Patents

Sorbant pour pompes à chaleur à absorption Download PDF

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Publication number
WO2013050242A1
WO2013050242A1 PCT/EP2012/068357 EP2012068357W WO2013050242A1 WO 2013050242 A1 WO2013050242 A1 WO 2013050242A1 EP 2012068357 W EP2012068357 W EP 2012068357W WO 2013050242 A1 WO2013050242 A1 WO 2013050242A1
Authority
WO
WIPO (PCT)
Prior art keywords
refrigerant
ionic liquid
absorption heat
reaction
use according
Prior art date
Application number
PCT/EP2012/068357
Other languages
German (de)
English (en)
Inventor
Matthias Seiler
Marc-Christoph Schneider
Olivier Zehnacker
Thomas Kuebelbaeck
Original Assignee
Evonik Degussa Gmbh
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Evonik Degussa Gmbh filed Critical Evonik Degussa Gmbh
Publication of WO2013050242A1 publication Critical patent/WO2013050242A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C09K5/047—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for absorption-type refrigeration systems
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
    • F25B—REFRIGERATION MACHINES, PLANTS OR SYSTEMS; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS
    • F25B30/00—Heat pumps
    • F25B30/04—Heat pumps of the sorption type

Definitions

  • Working medium must not fall below a water concentration of 35 to 40 wt .-% in the working medium, otherwise it would lead to the crystallization of lithium bromide and thereby disruption up to a solidification of the
  • WO 91/14678 and WO 2009/074535 describe the preparation of 1,3-dialklyimidazolium salts by reacting an alpha-dicarbonyl compound, an aldehyde, a
  • Electrolyte with improved ionic conductivity and as a microwave absorbing medium Electrolyte with improved ionic conductivity and as a microwave absorbing medium.
  • the invention accordingly provides the use of an ionic liquid prepared by imple mentation of formaldehyde, at least one Ci-4-alkylamine, at least one Ci-5-carboxylic acid and glyoxal, as a sorbent in an absorption heat pump.
  • absorption heat pump includes all devices that absorb heat at a low temperature level and at a higher Temperature level is released again and by
  • Absorptive heat pumps according to the invention thus include both absorption chillers and absorption heat pumps in the narrower sense, in which absorber and evaporator are operated at a lower working pressure than desorber and condenser, as well as absorption heat transformers in which absorber and evaporator at a higher
  • Ci-4-alkylamine at least one Ci-5-carboxylic acid and glyoxal produced.
  • Ci-4-Alkylamin are all primary alkylamines having 1 to 4 carbon atoms. Preference is given to methylamine,
  • ammonia is also used in the preparation of the ionic liquid.
  • the molar ratio of a C 1-4 -alkylamine is also used in the preparation of the ionic liquid.
  • Formaldehyde and glyoxal are preferably used as aqueous solutions.
  • formaldehyde at least one
  • Ci-4-alkylamine at least one Ci-5-carboxylic acid and glyoxal can be carried out in a solvent.
  • reaction takes place without addition of an organic solvent.
  • the implementation takes place
  • the ionic liquid obtained by the reaction of formaldehyde, at least one C 1-4 -alkylamine, at least one C 1-5 -carboxylic acid and glyoxal can be used as sorbent in an absorption heat pump without further purification
  • the working medium may contain, in addition to refrigerant and ionic liquid, further additives, preferably corrosion inhibitors.
  • the proportion of corrosion inhibitors is preferably 10 to 50,000 ppm, more preferably 100 to 10,000 ppm, based on the mass of the ionic
  • Preferred inorganic corrosion inhibitors are Li 2 Cr0 4 , Li 2 Mo0 4 , Li 3 VO, LiVO 3 , NiBr 2 , Li 3 PO 4 , CoBr 2 and LiOH.
  • Suitable organic corrosion inhibitors are amines and alkanolamines, preferably 2-aminoethanol,
  • Phosphoric acid esters in particular phosphoric acid esters of ethoxylated fatty alcohols, and fatty acid-alkanolamine mixtures.
  • Preferred organic corrosion inhibitors are benzimidazole and especially benzotriazole.
  • the working medium can also be used as an additive to improve the efficiency of a monohydric aliphatic alcohol having 6 to 10
  • the alcohol is preferably a primary alcohol having a branched alkyl group, and more preferably 2-ethyl-1-hexanol.
  • the working medium is a refrigerant and a by reacting formaldehyde, at least one Ci-4-alkylamine, at least one Ci-5-carboxylic acid and glyoxal produced ionic
  • Ci-4-alkylamine, Ci-5-carboxylic acid and glyoxal produced.
  • ionic liquid 95% by weight of ionic liquid and more preferably 20 to 67% by weight of refrigerant and 30 to 80% by weight of ionic liquid.
  • vapor refrigerant is absorbed in low-refrigerant working medium in the absorber to obtain a
  • the absorption heat pump according to the invention can be designed both in one stage and in several stages with several coupled circuits of the working medium.
  • the absorption heat pump according to the invention can be designed both in one stage and in several stages with several coupled circuits of the working medium.
  • Absorption heat pump is an absorption chiller and in the evaporator heat from a medium to be cooled
  • Liquid can not be used as a sorbent because of their corrosivity in contact with the working medium.
  • Reaction temperature is maintained by cooling to 10 ° C. After stirring for 60 minutes, 580 g (4.00 mol) of 40% by weight aqueous glyoxal are metered in at 15 to 20 ° C., and
  • Example 1 is repeated, but 296 g (4.00 mol) of propionic acid are used instead of acetic acid. There are obtained 660 g (97%) of 1, 3-dimethylimidazolium propionate.
  • Example 1 Preparation of 1,3-dimethylimidazolium butyrate Example 1 is mixed with 188 g (2.40 mol) of 40 wt% aqueous methylamine, 98 g (1.20 mol) of 37 wt% aqueous
  • Example 3 is repeated, but instead of the butyric acid 123 g (1.20 mol) of pivalic acid is used. There are obtained 206 g (94%) of 1, 3-dimethylimidazolium pivalate.
  • the corrosion rate of copper material number 2.0060 (E-Cu57 according to DIN) and of stainless steel, was determined by measuring the potentiodynamic polarization resistance and evaluation by panel plot according to the method ASTM G59-97 (2009). Material number 1.4463, determined.
  • the investigated ionic liquids and their trade names, the proportions by weight of ionic liquid and corrosion inhibitor and the specific corrosion rates are summarized in Tables 1 and 2.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Combustion & Propulsion (AREA)
  • Thermal Sciences (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Sorption Type Refrigeration Machines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'utilisation d'un liquide ionique produit au moyen d'une réaction consistant à faire réagir un formaldéhyde, au moins une alkylamine en C1-4, au moins un acide carboxylique en C1-5 et un glyoxal, en tant que sorbant dans une substance active pour pompes à chaleur à absorption permet d'empêcher la corrosion de la substance actif par comparaison à des liquides ioniques courants dans le commerce.
PCT/EP2012/068357 2011-10-04 2012-09-18 Sorbant pour pompes à chaleur à absorption WO2013050242A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102011083976A DE102011083976A1 (de) 2011-10-04 2011-10-04 Sorptionsmittel für Absorptionswärmepumpen
DE102011083976.3 2011-10-04

Publications (1)

Publication Number Publication Date
WO2013050242A1 true WO2013050242A1 (fr) 2013-04-11

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2012/068357 WO2013050242A1 (fr) 2011-10-04 2012-09-18 Sorbant pour pompes à chaleur à absorption

Country Status (2)

Country Link
DE (1) DE102011083976A1 (fr)
WO (1) WO2013050242A1 (fr)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8623123B2 (en) 2009-02-02 2014-01-07 Evonik Degussa Gmbh CO2 absorption from gas mixtures using an aqueous solution of 4-amino-2,2,6,6-tetramethyl piperidine
US8932478B2 (en) 2008-02-05 2015-01-13 Evonik Degussa Gmbh Process for the absorption of a volatile substance in a liquid absorbent
US9221007B2 (en) 2011-11-14 2015-12-29 Evonik Degussa Gmbh Method and device for separating acid gases from a gas mixture
US9630140B2 (en) 2012-05-07 2017-04-25 Evonik Degussa Gmbh Method for absorbing CO2 from a gas mixture
US9840473B1 (en) 2016-06-14 2017-12-12 Evonik Degussa Gmbh Method of preparing a high purity imidazolium salt
DE102016210483A1 (de) 2016-06-14 2017-12-14 Evonik Degussa Gmbh Verfahren und Absorptionsmittel zur Entfeuchtung von feuchten Gasgemischen
EP3257568A1 (fr) 2016-06-14 2017-12-20 Evonik Degussa GmbH Procede de deshumidification de melanges gazeux humides par des liquides ioniques
EP3257569A1 (fr) 2016-06-14 2017-12-20 Evonik Degussa GmbH Procede de deshumidification des melanges gazeux humides
US9878285B2 (en) 2012-01-23 2018-01-30 Evonik Degussa Gmbh Method and absorption medium for absorbing CO2 from a gas mixture
US10138209B2 (en) 2016-06-14 2018-11-27 Evonik Degussa Gmbh Process for purifying an ionic liquid
US10500540B2 (en) 2015-07-08 2019-12-10 Evonik Degussa Gmbh Method for dehumidifying humid gas mixtures using ionic liquids
US10512883B2 (en) 2016-06-14 2019-12-24 Evonik Degussa Gmbh Process for dehumidifying moist gas mixtures
US10512881B2 (en) 2016-06-14 2019-12-24 Evonik Degussa Gmbh Process for dehumidifying moist gas mixtures
US11207635B2 (en) 2018-12-04 2021-12-28 Evonik Operations Gmbh Process for dehumidifying moist gas mixtures

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102015001190B4 (de) 2015-01-31 2016-09-01 Karlfried Pfeifenbring Kühlelement für metallurgische Öfen sowie Verfahren zur Herstellung eines Kühlelements
DE102022111427A1 (de) 2022-05-09 2023-11-09 Vaillant Gmbh Zwischenraum-Wärmeübertrager

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4450277A (en) 1979-10-08 1984-05-22 Basf Aktiengesellschaft Preparation of 1-substituted imidazoles
WO1991014678A1 (fr) 1990-03-29 1991-10-03 E.I. Du Pont De Nemours And Company Preparation de sels d'imidazolium 1,3-disubstitue
WO2002094883A2 (fr) 2001-01-22 2002-11-28 Covalent Associates, Inc. Procede en une etape de preparation de sels hydrophobes exempts d'halogenure
WO2005113702A1 (fr) 2004-05-21 2005-12-01 Basf Aktiengesellschaft Nouvelles paires de substances pour des pompes a chaleur a absorption, des machines frigorifiques a absorption et des transformateurs thermiques
WO2006134015A1 (fr) 2005-06-17 2006-12-21 Evonik Degussa Gmbh Milieux de travail d'un genre nouveau pour processus de refrigeration
WO2009027250A2 (fr) 2007-08-31 2009-03-05 Basf Se Distillation de fluides ioniques
WO2009074535A2 (fr) 2007-12-12 2009-06-18 Basf Se Procédé de production de sels d'imidazolium disubstitués
EP2246651A2 (fr) * 2009-04-27 2010-11-03 Basf Se Pompes à chaleur à absorption, machines frigorifiques à absorption et transformateurs thermiques à absorption à base d'acétate EMIM / méthanol
WO2011056924A2 (fr) 2009-11-04 2011-05-12 The Board Of Trustees Of The University Of Alabama Procédés permettant de dissoudre des polymères à l'aide de mélanges de différents liquides ioniques et compositions contenant ces mélanges

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4450277A (en) 1979-10-08 1984-05-22 Basf Aktiengesellschaft Preparation of 1-substituted imidazoles
WO1991014678A1 (fr) 1990-03-29 1991-10-03 E.I. Du Pont De Nemours And Company Preparation de sels d'imidazolium 1,3-disubstitue
WO2002094883A2 (fr) 2001-01-22 2002-11-28 Covalent Associates, Inc. Procede en une etape de preparation de sels hydrophobes exempts d'halogenure
WO2005113702A1 (fr) 2004-05-21 2005-12-01 Basf Aktiengesellschaft Nouvelles paires de substances pour des pompes a chaleur a absorption, des machines frigorifiques a absorption et des transformateurs thermiques
WO2006134015A1 (fr) 2005-06-17 2006-12-21 Evonik Degussa Gmbh Milieux de travail d'un genre nouveau pour processus de refrigeration
WO2009027250A2 (fr) 2007-08-31 2009-03-05 Basf Se Distillation de fluides ioniques
WO2009074535A2 (fr) 2007-12-12 2009-06-18 Basf Se Procédé de production de sels d'imidazolium disubstitués
EP2246651A2 (fr) * 2009-04-27 2010-11-03 Basf Se Pompes à chaleur à absorption, machines frigorifiques à absorption et transformateurs thermiques à absorption à base d'acétate EMIM / méthanol
WO2011056924A2 (fr) 2009-11-04 2011-05-12 The Board Of Trustees Of The University Of Alabama Procédés permettant de dissoudre des polymères à l'aide de mélanges de différents liquides ioniques et compositions contenant ces mélanges

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8932478B2 (en) 2008-02-05 2015-01-13 Evonik Degussa Gmbh Process for the absorption of a volatile substance in a liquid absorbent
US8623123B2 (en) 2009-02-02 2014-01-07 Evonik Degussa Gmbh CO2 absorption from gas mixtures using an aqueous solution of 4-amino-2,2,6,6-tetramethyl piperidine
US9221007B2 (en) 2011-11-14 2015-12-29 Evonik Degussa Gmbh Method and device for separating acid gases from a gas mixture
US9878285B2 (en) 2012-01-23 2018-01-30 Evonik Degussa Gmbh Method and absorption medium for absorbing CO2 from a gas mixture
US9630140B2 (en) 2012-05-07 2017-04-25 Evonik Degussa Gmbh Method for absorbing CO2 from a gas mixture
US10500540B2 (en) 2015-07-08 2019-12-10 Evonik Degussa Gmbh Method for dehumidifying humid gas mixtures using ionic liquids
EP3257568A1 (fr) 2016-06-14 2017-12-20 Evonik Degussa GmbH Procede de deshumidification de melanges gazeux humides par des liquides ioniques
EP3257569A1 (fr) 2016-06-14 2017-12-20 Evonik Degussa GmbH Procede de deshumidification des melanges gazeux humides
DE102016210483A1 (de) 2016-06-14 2017-12-14 Evonik Degussa Gmbh Verfahren und Absorptionsmittel zur Entfeuchtung von feuchten Gasgemischen
US10105644B2 (en) 2016-06-14 2018-10-23 Evonik Degussa Gmbh Process and absorbent for dehumidifying moist gas mixtures
US10138209B2 (en) 2016-06-14 2018-11-27 Evonik Degussa Gmbh Process for purifying an ionic liquid
US10493400B2 (en) 2016-06-14 2019-12-03 Evonik Degussa Gmbh Process for dehumidifying moist gas mixtures
US9840473B1 (en) 2016-06-14 2017-12-12 Evonik Degussa Gmbh Method of preparing a high purity imidazolium salt
US10512883B2 (en) 2016-06-14 2019-12-24 Evonik Degussa Gmbh Process for dehumidifying moist gas mixtures
US10512881B2 (en) 2016-06-14 2019-12-24 Evonik Degussa Gmbh Process for dehumidifying moist gas mixtures
US11207635B2 (en) 2018-12-04 2021-12-28 Evonik Operations Gmbh Process for dehumidifying moist gas mixtures

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