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WO2017085600A1 - Heat transfer fluids including deep eutectic solvents - Google Patents

Heat transfer fluids including deep eutectic solvents Download PDF

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Publication number
WO2017085600A1
WO2017085600A1 PCT/IB2016/056771 IB2016056771W WO2017085600A1 WO 2017085600 A1 WO2017085600 A1 WO 2017085600A1 IB 2016056771 W IB2016056771 W IB 2016056771W WO 2017085600 A1 WO2017085600 A1 WO 2017085600A1
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WO
WIPO (PCT)
Prior art keywords
heat transfer
transfer fluid
combinations
metal oxide
group
Prior art date
Application number
PCT/IB2016/056771
Other languages
French (fr)
Inventor
Mohammed Bismillah ANSARI
Syed Azhar Hashmi
Original Assignee
Sabic Global Technologies B.V.
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 Sabic Global Technologies B.V. filed Critical Sabic Global Technologies B.V.
Publication of WO2017085600A1 publication Critical patent/WO2017085600A1/en

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    • 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
    • C09K5/08—Materials not undergoing a change of physical state when used
    • C09K5/10—Liquid materials
    • C09K5/12—Molten materials, i.e. materials solid at room temperature, e.g. metals or salts

Definitions

  • the presently disclosed subject matter relates to deep eutectic solvents for use as heat transfer fluids.
  • Heat transfer fluids can be used in a variety of applications, including reaction cooling and heating, plastic molding, temperature baths, coolant systems and refrigeration systems. Heat transfer fluids can be a medium of heat exchange from one source to another. Heat transfer fluids can be pumped through heat exchange equipment, such as heat exchangers and jackets, to provide or remove heat, and can thereby control the temperature of a vessel or process.
  • the rate of heat exchange can be controlled by altering the surface area and materials of the heat exchange equipment, or the flow of the heat transfer fluid within the heat exchange equipment. Additionally, the rate of heat exchange can be effected by certain properties of the heat transfer fluid, including its specific heat and thermal conductivity. It can be desirable to use a heat exchange fluid that remains liquid in a wide range of operating temperatures and flows freely, i.e., is not overly viscous. Heat transfer fluids can be aqueous, non-aqueous, organic and/or inorganic.
  • the heat transfer fluid can include a deep eutectic solvent.
  • the deep eutectic solvent can include one or more of a quaternary ammonium halide salt, ethylammonium chloride, a metal salt, and a phosphonium salt, and a hydrogen bond donor.
  • the heat transfer fluid can further include metal oxide nanoparticles.
  • the hydrogen bond donor of the deep eutectic fluid can include urea, acetamide, thiourea, trichloroacetic acid, phenylacetic acid, malonic acid, oxalic acid, p-toluene sulfonic acid, m-cresol, phenol, ethylene glycol, and/or gylcerol.
  • the deep eutectic fluid can include a second hydrogen bond donor.
  • the metal oxide nanoparticles can be alkali metal oxides, alkaline earth metal oxides, transition metal oxides, and combinations thereof.
  • the heat transfer fluid can further include an additive such as a metal salt, a metal oxide, an organic solvent, and combinations thereof.
  • the heat transfer fluid can be mixed with water, oil, and/or an organic material prior to use.
  • the presently disclosed subject matter provides a heat transfer fluid including a deep eutectic solvent.
  • the heat transfer fluid can include two components, three components, or four components.
  • the deep eutectic solvent can include a salt.
  • the deep eutectic solvent can include one or more of a quaternary ammonium halide salt, a metal salt, a phosponium salt and ethylammonium chloride.
  • the quaternary ammonium halide salt can be choline chloride, chlorcholine chloride, choline iodide, choline bromide, tetrabutylammonium chloride, triethylbenzylammonium chloride, benzalkonium chloride, benzethonium chloride, methylbenzethonium chloride, cetalkonium chloride, cetylpyridinium chloride, cetrimonium, stearalkonium chloride, dofanium chloride, tetramethylammonium chloride, tetraethylammonium bromide, didecyldimethylammonium chloride and domiphen bromide.
  • the quaternary ammonium halide salt is choline chloride.
  • the metal salt can include Aluminum (Al), Zinc (Zn), Tin (Sn), Iron (Fe), Chromium (Cr), Manganese (Mn), Cobalt (Co), Nickel (Ni), Copper (Cu), and/or Gallium (Ga).
  • the metal salt can be hydrated.
  • the metal salt can include a halide.
  • the phosphonium salt can include a halide.
  • the phosphonium salt can include phosphonium chloride, phosphonium bromide, and/or phosphonium iodide.
  • the phosphonium salt can be a quaternary ammonium salt.
  • the term “about” or “approximately” means within an acceptable error range for the particular value as determined by one of ordinary skill in the art, which will depend in part on how the value is measured or determined, i.e., the limitations of the measurement system. For example, “about” can mean a range of up to 20%, up to 10%, up to 5%), and or up to 1% of a given value.
  • the deep eutectic solvent can further include one or more hydrogen bond donors.
  • Hydrogen bond donors for use in the presently disclosed deep eutectic solvent can include an amide and/or an acid and/or an alcohol.
  • suitable amides can include urea, acetamide, or thiourea.
  • suitable acids can include trichloroacetic acid, phenylacetic acid, malonic acid, oxalic acid, or p-toluene sulfonic acid.
  • Suitable alcohols can include m-cresol, phenol, ethylene glycol, or gylcerol.
  • the hydrogen bond donor can include glycerol.
  • the salt and the hydrogen can be present in the deep eutectic solvent in a particular ratio.
  • the molar ratio of salt to hydrogen bond donor can be from about 1 :5 to about 2: 1.
  • the heat transfer fluid can further include one or more additives.
  • the one or more additives can include a metal salt, an organic solvent, a metal oxide, nanoparticles, and combinations thereof.
  • the heat transfer fluid can include nanoparticles.
  • the nanoparticles can include inorganic metal oxides.
  • the nanoparticles can include alkali metal oxides, alkaline earth metal oxides, transition metal oxides, and combinations thereof.
  • the nanoparticles can have diameters from about 1 nm to about 100 nm.
  • the deep eutectic solvent can contain from about 0.001 wt-% to about 10 wt-% nanoparticles.
  • Heat transfer fluids of the presently disclosed subject matter can exhibit various physical properties.
  • a heat transfer fluid can have a boiling point from about -50°C to about 400°C.
  • a heat transfer fluid can have a melting point from about -100°C to about 100°C.
  • a heat transfer fluid can have low moisture content, for example, less than about 5 wt-% water. In certain embodiments, a heat transfer fluid is non- corrosive.
  • a heat transfer fluid can be mixed with another component prior to use.
  • a heat transfer fluid can be mixed with water, oil, an organic material, or combinations thereof.
  • a heat transfer fluid including a deep eutectic solvent of the presently disclosed subject matter can be used in various applications, including, but not limited to heat exchangers, including shell and tube heat exchangers and plate heat exchangers, jacketed vessels, and heating and cooling coils.
  • the heat transfer fluids of the presently disclosed subject matter can have advantages over certain existing technologies. Exemplary advantages include suitability for use in a broad range of operating temperatures, stability at high operating temperatures, compatibility with existing heat transfer equipment, and improved heat transfer properties.

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  • 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)
  • Lubricants (AREA)

Abstract

The presently disclosed subject matter relates to heat transfer fluids including a deep eutectic solvent. An example heat transfer fluid includes a deep eutectic solvent including one or more of a quaternary ammonium halide salt, ethylammonium chloride, a metal salt, and a phosphonium salt, and a hydrogen bond donor. The heat transfer fluid can further include metal oxide nanoparticles.

Description

HEAT TRANSFER FLUIDS INCLUDING DEEP EUTECTIC SOLVENTS
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application claims priority to and the benefit of U.S. Provisional Application No. 62/256,047, filed November 16, 2015. The contents of the referenced application are incorporated into the present application by reference.
FIELD
[0002] The presently disclosed subject matter relates to deep eutectic solvents for use as heat transfer fluids.
BACKGROUND
[0003] Heat transfer fluids can be used in a variety of applications, including reaction cooling and heating, plastic molding, temperature baths, coolant systems and refrigeration systems. Heat transfer fluids can be a medium of heat exchange from one source to another. Heat transfer fluids can be pumped through heat exchange equipment, such as heat exchangers and jackets, to provide or remove heat, and can thereby control the temperature of a vessel or process.
[0004] The rate of heat exchange can be controlled by altering the surface area and materials of the heat exchange equipment, or the flow of the heat transfer fluid within the heat exchange equipment. Additionally, the rate of heat exchange can be effected by certain properties of the heat transfer fluid, including its specific heat and thermal conductivity. It can be desirable to use a heat exchange fluid that remains liquid in a wide range of operating temperatures and flows freely, i.e., is not overly viscous. Heat transfer fluids can be aqueous, non-aqueous, organic and/or inorganic.
[0005] Certain heat transfer fluids are known in the art. International Patent Publication No. WO 1989/007634 discloses heat transfer fluid compositions including diphenyl ether, terphenyl and at least one additional aromatic compound. Hayyan et al., "Tri ethylene glycol based deep eutectic solvents and their physical properties," J. of the Taiwan Inst, of Chem. Engineers, p. 1-7 (2015) discloses deep eutectic solvents including a tri ethylene glycol hydrogen bond donor that can be used as a heat transfer fluid. French Patent Publication No. FR2440531 discloses a heat exchanger that includes at least one eutectic plate, and which can be filled with a eutectic mixture. International Patent Publication No. WO 2013/153203 discloses deep eutectic solvents including a quaternary ammonium or phosphonium salt in the presence of a hydrogen bond donor that can be used as heat transfer fluids.
[0006] However, there remains a need for improved heat transfer fluids.
SUMMARY OF THE DISCLOSED SUBJECT MATTER
[0007] The presently disclosed subject matter provides heat transfer fluids. In certain embodiments, the heat transfer fluid can include a deep eutectic solvent. The deep eutectic solvent can include one or more of a quaternary ammonium halide salt, ethylammonium chloride, a metal salt, and a phosphonium salt, and a hydrogen bond donor. The heat transfer fluid can further include metal oxide nanoparticles.
[0008] In certain embodiments, the hydrogen bond donor of the deep eutectic fluid can include urea, acetamide, thiourea, trichloroacetic acid, phenylacetic acid, malonic acid, oxalic acid, p-toluene sulfonic acid, m-cresol, phenol, ethylene glycol, and/or gylcerol. In certain embodiments, the deep eutectic fluid can include a second hydrogen bond donor.
[0009] In certain embodiments, the metal oxide nanoparticles can be alkali metal oxides, alkaline earth metal oxides, transition metal oxides, and combinations thereof.
[0010] In certain embodiments, the heat transfer fluid can further include an additive such as a metal salt, a metal oxide, an organic solvent, and combinations thereof.
[0011] In certain embodiments, the heat transfer fluid can be mixed with water, oil, and/or an organic material prior to use. DETAILED DESCRIPTION
[0012] The presently disclosed subject matter provides a heat transfer fluid including a deep eutectic solvent. In certain embodiments, the heat transfer fluid can include two components, three components, or four components.
[0013] In certain embodiments, the deep eutectic solvent can include a salt. In certain embodiments, the deep eutectic solvent can include one or more of a quaternary ammonium halide salt, a metal salt, a phosponium salt and ethylammonium chloride.
[0014] For example, and not limitation, the quaternary ammonium halide salt can be choline chloride, chlorcholine chloride, choline iodide, choline bromide, tetrabutylammonium chloride, triethylbenzylammonium chloride, benzalkonium chloride, benzethonium chloride, methylbenzethonium chloride, cetalkonium chloride, cetylpyridinium chloride, cetrimonium, stearalkonium chloride, dofanium chloride, tetramethylammonium chloride, tetraethylammonium bromide, didecyldimethylammonium chloride and domiphen bromide. In particular non-limiting embodiments, the quaternary ammonium halide salt is choline chloride.
[0015] For example, and not limitation, the metal salt can include Aluminum (Al), Zinc (Zn), Tin (Sn), Iron (Fe), Chromium (Cr), Manganese (Mn), Cobalt (Co), Nickel (Ni), Copper (Cu), and/or Gallium (Ga). In certain embodiments, the metal salt can be hydrated. In certain embodiments, the metal salt can include a halide.
[0016] In certain embodiments, the phosphonium salt can include a halide. For example, and not by way of limitation, the phosphonium salt can include phosphonium chloride, phosphonium bromide, and/or phosphonium iodide. In certain embodiments, the phosphonium salt can be a quaternary ammonium salt.
[0017] As used herein, the term "about" or "approximately" means within an acceptable error range for the particular value as determined by one of ordinary skill in the art, which will depend in part on how the value is measured or determined, i.e., the limitations of the measurement system. For example, "about" can mean a range of up to 20%, up to 10%, up to 5%), and or up to 1% of a given value.
[0018] In certain embodiments, the deep eutectic solvent can further include one or more hydrogen bond donors. Hydrogen bond donors for use in the presently disclosed deep eutectic solvent can include an amide and/or an acid and/or an alcohol. For example, and not limitation, suitable amides can include urea, acetamide, or thiourea. Suitable acids can include trichloroacetic acid, phenylacetic acid, malonic acid, oxalic acid, or p-toluene sulfonic acid. Suitable alcohols can include m-cresol, phenol, ethylene glycol, or gylcerol. In particular embodiments, the hydrogen bond donor can include glycerol.
[0019] In certain embodiments, the salt and the hydrogen can be present in the deep eutectic solvent in a particular ratio. For example, the molar ratio of salt to hydrogen bond donor can be from about 1 :5 to about 2: 1.
[0020] In certain embodiments, the heat transfer fluid can further include one or more additives. For example, and not limitation, the one or more additives can include a metal salt, an organic solvent, a metal oxide, nanoparticles, and combinations thereof.
[0021] In particular embodiments, the heat transfer fluid can include nanoparticles. The nanoparticles can include inorganic metal oxides. For example, and not limitation, the nanoparticles can include alkali metal oxides, alkaline earth metal oxides, transition metal oxides, and combinations thereof. In certain embodiments, the nanoparticles can have diameters from about 1 nm to about 100 nm. In certain embodiments, the deep eutectic solvent can contain from about 0.001 wt-% to about 10 wt-% nanoparticles.
[0022] Heat transfer fluids of the presently disclosed subject matter can exhibit various physical properties. In certain embodiments, a heat transfer fluid can have a boiling point from about -50°C to about 400°C. In certain embodiments, a heat transfer fluid can have a melting point from about -100°C to about 100°C.
[0023] In certain embodiments, a heat transfer fluid can have low moisture content, for example, less than about 5 wt-% water. In certain embodiments, a heat transfer fluid is non- corrosive.
[0024] In certain embodiments, a heat transfer fluid can be mixed with another component prior to use. In particular embodiments, a heat transfer fluid can be mixed with water, oil, an organic material, or combinations thereof.
[0025] A heat transfer fluid including a deep eutectic solvent of the presently disclosed subject matter can be used in various applications, including, but not limited to heat exchangers, including shell and tube heat exchangers and plate heat exchangers, jacketed vessels, and heating and cooling coils.
[0026] The heat transfer fluids of the presently disclosed subject matter can have advantages over certain existing technologies. Exemplary advantages include suitability for use in a broad range of operating temperatures, stability at high operating temperatures, compatibility with existing heat transfer equipment, and improved heat transfer properties.
* * *
[0027] In addition to the various embodiments depicted and claimed, the disclosed subject matter is also directed to other embodiments having other combinations of the features disclosed and claimed herein. As such, the particular features presented herein can be combined with each other in other manners within the scope of the disclosed subject matter such that the disclosed subject matter includes any suitable combination of the features disclosed herein. The foregoing description of specific embodiments of the disclosed subject matter has been presented for purposes of illustration and description. It is not intended to be exhaustive or to limit the disclosed subject matter to those embodiments disclosed. [0028] It will be apparent to those skilled in the art that various modifications and variations can be made in the systems and methods of the disclosed subject matter without departing from the spirit or scope of the disclosed subject matter. Thus, it is intended that the disclosed subject matter include modifications and variations that are within the scope of the appended claims and their equivalents.

Claims

1. A heat transfer fluid comprising:
(a) a deep eutectic solvent comprising a compound selected from the group consisting of a quaternary ammonium halide salt, ethylammonium chloride, a metal salt, a phosphonium salt and combinations thereof and a hydrogen bond donor; and
(b) a nanoparticle comprising a metal oxide.
2. The heat transfer fluid of claim 1, wherein the quaternary ammonium halide salt is choline chloride.
3. The heat transfer fluid of claim 1, wherein the hydrogen bond donor is selected from the group consisting of urea, acetamide, thiourea, trichloroacetic acid, phenylacetic acid, malonic acid, oxalic acid, p-toluene sulfonic acid, m-cresol, phenol, ethylene glycol, gylcerol, and combinations thereof.
4. The heat transfer fluid of claim 1, wherein the hydrogen bond donor is selected from the group consisting of urea, acetamide, thiourea, and combinations thereof.
5. The heat transfer fluid of claim 1, further comprising a second hydrogen bond donor selected from the group consisting of trichloroacetic acid, phenylacetic acid, malonic acid, oxalic acid, p-toluene sulfonic acid, m-cresol, phenol, ethylene glycol, gylcerol, and combinations thereof.
6. The heat transfer fluid of claim 1, wherein the nanoparticle is selected from the group consisting of an alkali metal oxide, an alkaline earth metal oxide, a transition metal oxide, and combinations thereof.
7. The heat transfer fluid of claim 1, further comprising an additive selected from the group consisting of a metal salt, a metal oxide, an organic solvent, and combinations thereof.
8. A heat transfer fluid mixture comprising the heat transfer fluid of claim 1 and a second compound selected from the group consisting of water, oil, an organic material, and combinations thereof.
9. A heat transfer fluid comprising:
(a) a deep eutectic solvent comprising a compound selected from the group consisting of a quaternary ammonium halide salt, choline chloride, ethylammonium chloride, a metal salt, a phosphonium salt and combinations thereof and a hydrogen bond donor;
(b) a nanoparticle comprising a metal oxide selected from the group consisting of an alkaline metal oxide, an alkaline earth metal oxide, a transition metal oxide and combinations thereof; and
(c) an additive selected from the group consisting of a metal salt, a metal oxide, an organic solvent and combinations thereof.
PCT/IB2016/056771 2015-11-16 2016-11-10 Heat transfer fluids including deep eutectic solvents WO2017085600A1 (en)

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US201562256047P 2015-11-16 2015-11-16
US62/256,047 2015-11-16

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE1850195A1 (en) * 2018-02-22 2019-08-23 Kalmarsund Strategic Consultancy Ab Non-ionic deep eutectic mixtures for use as solvents and dispersants
EP4015595A1 (en) * 2020-12-21 2022-06-22 Rolls-Royce plc Machining coolant

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2440531A1 (en) 1978-10-31 1980-05-30 Masson Emilien Cooling panel for refrigerator vehicle - has eutectic mixture between inner and outer panels to increase rate of heat transfer
WO1989007634A1 (en) 1988-02-12 1989-08-24 The Dow Chemical Company Heat-transfer fluids and process for preparing the same
US20130068994A1 (en) * 2011-09-16 2013-03-21 Savannah River Nuclear Solutions, Llc Nanoparticle enhanced ionic liquid heat transfer fluids
WO2013153203A1 (en) 2012-04-12 2013-10-17 Technische Universiteit Eindhoven Pretreatment of lignocellulosic biomass and recovery of substituents using natural deep eutectic solvents/compound mixtures with low transition temperatures

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2440531A1 (en) 1978-10-31 1980-05-30 Masson Emilien Cooling panel for refrigerator vehicle - has eutectic mixture between inner and outer panels to increase rate of heat transfer
WO1989007634A1 (en) 1988-02-12 1989-08-24 The Dow Chemical Company Heat-transfer fluids and process for preparing the same
US20130068994A1 (en) * 2011-09-16 2013-03-21 Savannah River Nuclear Solutions, Llc Nanoparticle enhanced ionic liquid heat transfer fluids
WO2013153203A1 (en) 2012-04-12 2013-10-17 Technische Universiteit Eindhoven Pretreatment of lignocellulosic biomass and recovery of substituents using natural deep eutectic solvents/compound mixtures with low transition temperatures

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* Cited by examiner, † Cited by third party
Title
ESSA ISMAEIL ET AL: "TYPE III DEEP EUTECTIC SOLVENTS (DESs) AS BASE LUBRICANTS Thesis submitted for the degree of Doctor of Philosophy at the University of Leicester", 1 July 2015 (2015-07-01), XP055333770, Retrieved from the Internet <URL:https://lra.le.ac.uk/bitstream/2381/33465/1/2015_Ahmed_E I _ PhD.pdf> [retrieved on 20170110] *
HAYYAN ET AL.: "Triethylene glycol based deep eutectic solvents and their physical properties", J. OF THE TAIWAN INST. OF CHEM. ENGINEERS, 2015, pages 1 - 7
JI-YAO DONG ET AL: "Growth of ZnO Nanostructures with Controllable Morphology Using a Facile Green Antisolvent Method", JOURNAL OF PHYSICAL CHEMISTRY C, vol. 114, no. 19, 20 May 2010 (2010-05-20), US, pages 8867 - 8872, XP055333685, ISSN: 1932-7447, DOI: 10.1021/jp102396f *
LERON RHODA B ET AL: "Molar heat capacities of choline chloride-based deep eutectic solvents and their binary mixtures with water", THERMOCHIMICA ACTA, vol. 530, 2012, pages 52 - 57, XP028884468, ISSN: 0040-6031, DOI: 10.1016/J.TCA.2011.11.036 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE1850195A1 (en) * 2018-02-22 2019-08-23 Kalmarsund Strategic Consultancy Ab Non-ionic deep eutectic mixtures for use as solvents and dispersants
WO2019164442A1 (en) * 2018-02-22 2019-08-29 Kalmarsund Strategic Consultancy Ab Non-ionic deep eutectic mixtures for use as solvents and dispersants
EP4015595A1 (en) * 2020-12-21 2022-06-22 Rolls-Royce plc Machining coolant
US20220195280A1 (en) * 2020-12-21 2022-06-23 Rolls-Royce Plc Machining coolant

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