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US20110056656A1 - Method for Producing a Latent Heat Storage Material and Dialkyl Ether as a Latent Heat Storage Material - Google Patents

Method for Producing a Latent Heat Storage Material and Dialkyl Ether as a Latent Heat Storage Material Download PDF

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Publication number
US20110056656A1
US20110056656A1 US12/863,643 US86364309A US2011056656A1 US 20110056656 A1 US20110056656 A1 US 20110056656A1 US 86364309 A US86364309 A US 86364309A US 2011056656 A1 US2011056656 A1 US 2011056656A1
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new
mass
heat storage
latent heat
residues
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US12/863,643
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Holger Ziehe
Achim Weitze
Thoralf Gross
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C9/00—Aliphatic saturated hydrocarbons
    • C07C9/22—Aliphatic saturated hydrocarbons with more than fifteen carbon atoms
    • 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
    • C09K5/06—Materials undergoing a change of physical state when used the change of state being from liquid to solid or vice versa
    • 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
    • C09K5/06—Materials undergoing a change of physical state when used the change of state being from liquid to solid or vice versa
    • C09K5/063—Materials absorbing or liberating heat during crystallisation; Heat storage materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
    • C07C2523/74—Iron group metals
    • C07C2523/755—Nickel

Definitions

  • the invention relates to a method for producing a latent heat storage material from linear alcohols and dialkyl ether as a latent heat storage material.
  • Phase change materials may release or absorb, respectively, or store, respectively, heat by melting or solidifying, respectively, within a defined temperature range, and thus function as latent heat storage materials.
  • This principle of heat storage may also be used, for example, in the wall insulation of buildings.
  • Such latent heat storage materials are, e.g. in the form of micro-capsules, introduced into the wall plaster or into gypsum plasterboards and liquefy during the day with high heat input. The heat absorbed is stored in the wall and keeps the interior cool. Following cooling during the evening hours and at night, the liquid storages solidify and release the crystallization heat to the environment. In that, the interior is warmed up.
  • paraffins and paraffin mixtures are used as latent heat storage materials.
  • Commercially available paraffin mixtures for PCM applications are, for example, Rubitherm® 27 and Rubitherm® 31.
  • the main component of the above Rubitherm® mixtures is C 18 paraffin with a content of only 59 or 39% by mass, respectively.
  • These paraffin mixtures consist of even- and odd-numbered linear paraffins in the chain length range of C 17 to C 21 or C 17 to approx. C 30 , respectively, however, have a portion of linear chains of 98.0 or 95.6% by mass, respectively.
  • Paraffins may also be produced by hydrating commercially available alpha-olefins. These, however, only have linearities of approx. 90 to less than 95% by mass in the C 16 to C 18 range, and have the disadvantage that due to the branched side products, their melting enthalpy is clearly lower in comparison to that of highly linear paraffins.
  • the object of the present invention therefore is the provision of highly linear compounds, like paraffins, with a defined chain length for use as latent heat storage materials.
  • highly linear compounds like paraffins
  • the melting range of highly pure paraffins is clearly narrower compared to paraffin mixtures, and thus the full storage capacity can be used at low temperature differences already.
  • the melting enthalpy of the pure substance is clearly higher than that of the mixtures.
  • the melting temperature of the PCM can be set across a wide temperature range.
  • paraffins preferably fulfill the following specification independent from each other:
  • the dialkyl ethers respectively have two residues R, so that the limit values are respectively lower.
  • the dialkyl ethers preferably fulfill the following specification independent from each other:
  • the alcohols are purified or selected, respectively, such that they already fulfill the above limit values for the paraffins, for producing the dialkyl ethers as well as for producing the paraffins.
  • the latent heat storage material is obtainable by dehydrating linear fatty alcohols to dialkyl ethers or to olefins, wherein the latter are subsequently hydrated to paraffins.
  • Fatty alcohols in terms of this invention are alcohols with C-numbers higher than or equal to 6 and preferably with terminal hydroxy groups.
  • Particularly suitable starting materials in case of the paraffins are cetyl alcohol or stearyl alcohol, and in case of the dialkyl ethers lauryl alcohol or myristyl alcohol.
  • linear paraffins are suited as linear paraffins for PCM applications, which can be produced by dehydrating linear alcohols to linear olefins and their subsequent hydration.
  • the linear alcohols used are easily available as single sections and are preferably based on renewable vegetable or animal raw materials, in particular vegetable ones, like e.g. palm oil, palm kernel oil, coconut oil, rapeseed oil or other vegetable oils.
  • Alcohols obtainable from natural raw materials are characterized by an increased linearity of e.g. >98% by mass.
  • the paraffins produced therefrom are therefore surprisingly well suited for application in PCMs.
  • paraffins may also be used, which can be produced by dehydrating synthetic alcohols.
  • chain length range C 16 to C 18 normally these frequently only have linearities from 93 to 99%.
  • linear paraffins as PCMs is known, just like the production of paraffins from fatty alcohols. So far, however, no paraffins have been described for this application as latent heat storage material, which are produced from dehydrated alcohols, in particular such ones, which are available from renewable raw materials.
  • the prices of the paraffins are higher than the prices of fatty alcohols.
  • the required quantities of latent heat storage used directly correlate with the melting heat used, i.e. that substances which have a 20% higher melting heat, also accordingly have to be used in lesser quantities in order to achieve the same effect.
  • textiles can be produced with the same storage capacity with a lesser weight, and thus the wearing comfort can be clearly increased.
  • a further dehydration product of linear fatty alcohols are dialkyl ethers. These are likewise very non-polar and are characterized by sharp melting peaks and a high melting heat. In particular didodecyl ether and ditetradecyl ether have similar melting temperatures like e.g. C 18 or C 22 paraffins, respectively.
  • Suitable catalysts for the dehydration to dialkyl ethers are clays, including boehmitic clays.
  • the dialkyl ethers In the comparison of products produced by means of dehydrating fatty alcohol, dialkyl ethers and olefins/paraffins, the dialkyl ethers have the advantage that they can be produced economically, since for every 2 mol of fatty alcohol, only 1 mol of water has to be eliminated.
  • the ethers may be stabilized against peroxide formation by means of antioxidants, wherein it is assumed, that in the micro- or macro-capsules, in which PCMs are frequently used, a decomposition of the ethers is sufficiently minimized by the capsule layer (frequently a polymer layer).
  • the latent heat storage material is preferably encapsulated by a polymer material as the capsule wall in micro-capsules with average particle sizes in the range from 1 to 200 ⁇ m, or in macro-capsules with average particle sizes in the range of more than 200 ⁇ m to 2 cm.
  • Suitable polymer materials are, e.g., styrene divinylbenzene polymers or unsaturated polyesters.
  • Preferred wall materials since they are very resistant to ageing, particularly are thermoset polymers.
  • Suitable thermoset polymer materials are, for example, cross-linked formaldehyde resins, cross-linked polyureas and cross-linked polyurethanes as well as cross-linked methacrylic acid ester polymers.
  • Melting temperature and melting heat are determined by means of DSC analytics. With a defined heating and cooling rate, the onset temperature (melting temperature) and the area below the curve (melting heat) are determined. The melting temperatures and heats of the paraffins and paraffin mixtures determined by means of DSC are respectively represented in the experiment part.
  • FIG. 1 C-chain distribution, of paraffins Rubitherm® 27 and Rubitherm® 31;
  • FIG. 2 DSC diagram of C16 to C22 paraffins (pure);
  • FIG. 3 DSC diagram for comparison of Rubitherm® 31/Di-C12 ether/C20 paraffin
  • FIG. 4 DSC diagram for comparison of Rubitherm® 27/C18 paraffin/C16 paraffin
  • FIG. 5 DSC diagram Di-C12/C14/C16/C18 ethers
  • FIG. 6 DSC diagram for comparison of hexadecane from a synthetic/native source.
  • Rubitherm® 27 and Rubitherm® 31 have the composition as apparent from FIG. 1 (determined via GC) and furthermore show the following characteristic determined via DSC:
  • Dehydrating fatty alcohols to linear olefins 2474 g of NACOL® 16-99 (purity 99.5%, based on renewable raw materials) were mixed with 500 g of Al 2 O 3 and 60 ml of xylene in a 6 l flask and heated at up to 295° C. at the water separator for 4.5 hours. In that, 180 ml of water were formed. The hexadecene formed was distilled in vacuum. The yield was a mixture of alpha- and internal olefins.
  • Octadecane and Docosane were mixed at weight ratios of 1:1, 2:1, and 3:1, and the DSC curves were measured again.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Thermal Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Combustion & Propulsion (AREA)
  • Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Medicinal Preparation (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
US12/863,643 2008-01-23 2009-01-15 Method for Producing a Latent Heat Storage Material and Dialkyl Ether as a Latent Heat Storage Material Abandoned US20110056656A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102008005721A DE102008005721C5 (de) 2008-01-23 2008-01-23 Verfahren zur Herstellung eines Latentwärmespeichermaterials
DE102008005721.5 2008-01-23
PCT/DE2009/000036 WO2009092349A2 (fr) 2008-01-23 2009-01-15 Procédé de fabrication d'un matériau à changement de phase et éther dialkylé comme matériau à changement de phase

Related Parent Applications (1)

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PCT/DE2009/000036 A-371-Of-International WO2009092349A2 (fr) 2008-01-23 2009-01-15 Procédé de fabrication d'un matériau à changement de phase et éther dialkylé comme matériau à changement de phase

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US (2) US20110056656A1 (fr)
EP (1) EP2242734B1 (fr)
JP (1) JP5670202B2 (fr)
KR (2) KR101710016B1 (fr)
DE (1) DE102008005721C5 (fr)
ES (1) ES2650473T3 (fr)
PL (1) PL2242734T3 (fr)
TW (1) TWI400227B (fr)
WO (1) WO2009092349A2 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9000248B2 (en) 2009-10-30 2015-04-07 Kao Corporation Method for manufacturing olefins
US20150203734A1 (en) * 2012-08-10 2015-07-23 Jsr Corporation Heat storage material composition
US9968914B2 (en) 2012-12-26 2018-05-15 Kao Corporation Method for producing olefin
US20220340800A1 (en) * 2021-04-27 2022-10-27 Kyodo Yushi Co., Ltd. Cold and heat storage agent composition

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DE102009013315A1 (de) * 2009-03-18 2010-09-23 Sasol Germany Gmbh Beschichtungen unter Einsatz von Dialkyl-/Dialkenylethern als Hydrophobierungsmittel, deren Verwendung und Metalle versehen mit der Beschichtung
DE102009054802B4 (de) * 2009-12-16 2017-08-17 Holmenkol Gmbh Verwendung von Fettalkoholethern als Gleitmittel für Sportgeräte, Gleitmittelzusammensetzung und Verfahren zur Beschichtung eines Sportgeräts
US8957133B2 (en) 2010-07-20 2015-02-17 Basf Se Polyamide moldings comprising microencapsulated latent-heat-accumulator material
CN103108899A (zh) 2010-07-20 2013-05-15 巴斯夫欧洲公司 包含微胶囊化潜热蓄热器材料的聚酰胺模制品
CN102417812A (zh) * 2011-09-28 2012-04-18 兰州理工大学 正十四醇相变微胶囊及其制备方法
CN103468223A (zh) * 2013-09-30 2013-12-25 天津工业大学 一种相变储能材料大胶囊及其制备方法
CN112368355A (zh) * 2018-06-28 2021-02-12 株式会社钟化 蓄热材料组合物和其应用
EP4335838A1 (fr) 2022-09-06 2024-03-13 Sasol Chemicals GmbH Huiles d'insectes comme matières premières naturelles pour la production d'alcool

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9000248B2 (en) 2009-10-30 2015-04-07 Kao Corporation Method for manufacturing olefins
US20150203734A1 (en) * 2012-08-10 2015-07-23 Jsr Corporation Heat storage material composition
US9968914B2 (en) 2012-12-26 2018-05-15 Kao Corporation Method for producing olefin
US20220340800A1 (en) * 2021-04-27 2022-10-27 Kyodo Yushi Co., Ltd. Cold and heat storage agent composition
US12291667B2 (en) * 2021-04-27 2025-05-06 Kyodo Yushi Co., Ltd. Cold and heat storage agent composition

Also Published As

Publication number Publication date
WO2009092349A3 (fr) 2009-12-23
PL2242734T3 (pl) 2018-02-28
JP2011510140A (ja) 2011-03-31
US20160257628A1 (en) 2016-09-08
KR20160032256A (ko) 2016-03-23
TWI400227B (zh) 2013-07-01
ES2650473T3 (es) 2018-01-18
DE102008005721C5 (de) 2012-04-19
KR101710016B1 (ko) 2017-02-24
WO2009092349A2 (fr) 2009-07-30
JP5670202B2 (ja) 2015-02-18
US10654765B2 (en) 2020-05-19
DE102008005721B4 (de) 2010-03-18
EP2242734B1 (fr) 2017-09-06
DE102008005721A1 (de) 2009-08-06
TW200940492A (en) 2009-10-01
KR20100106593A (ko) 2010-10-01
EP2242734A2 (fr) 2010-10-27

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