CN105837581A - Hexafluorophosphate containing low-temperature phase change compound and preparation method and application thereof - Google Patents

Hexafluorophosphate containing low-temperature phase change compound and preparation method and application thereof Download PDF

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CN105837581A
CN105837581A CN201610271074.8A CN201610271074A CN105837581A CN 105837581 A CN105837581 A CN 105837581A CN 201610271074 A CN201610271074 A CN 201610271074A CN 105837581 A CN105837581 A CN 105837581A
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phase change
compound
low temperature
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change compound
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CN105837581B (en
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陈立庄
曹星星
薛迪
潘其建
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Jiangsu University of Science and Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems
    • 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
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

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Abstract

The invention belongs to the field of phase change materials and discloses a hexafluorophosphate containing low-temperature phase change compound and a preparation method and application thereof .The chemical formula of the compound is C9H20P2F12N2; at the temperature of 296 K, crystals belong to an orthorhombic system, and the space group is Pbca; at the temperature of 123 K, the crystals belong to a monoclinic system, and the space group is P21/c .At room temperature, a triethylene diamine derivative reacts with hexafluorophosphoric acid, the solution is subjected to slow volatilization, crystallization and self-assembly at the room temperature, and the phase change compound is prepared .According to the compound with a low-temperature phase change property, the adopted material preparation process is simple and easy to operate, raw material sources are sufficient, the production cost is low, the yield is high, and repeatability is good; the compound is not prone to be dissolved in a general solvent, the thermal decomposition temperature point is relatively high, and crystal particles are uniform .The phase change compound has huge application potential in the fields of textiles and garments, greenhouse planting, construction industry and the like.

Description

A kind of low temperature phase change compound containing hexafluoro-phosphate radical, preparation method and applications
Technical field
The invention belongs to phase-change material field, be specifically related to a kind of low temperature phase change compound containing hexafluoro-phosphate radical, Preparation method and applications.
Background technology
Phase-change material, is called for short PCM, is that phase transformation that is absorbable during phase-state change or that release energy stores Material, unnecessary energy storage can be got up by it, is discharged when needs energy again.Phase transition process Refer to that material maintains isothermal or approximation isothermal under certain condition, and be attended by substantial amounts of energy absorption or release Phase-state change process.This characteristic constitutes phase-change material and has the most wide variety of theoretical foundation.
From the point of view of current domestic and international present Research, simple molecular ion type phase-change material causes more and more Notice, such as Liu, M.L.Acta Crystal Sec E.2012, E68, m652；Chen,L.Z.；Huang,D. D.；Pan,Q.J.；Ge,J.Z.RSC Adv.2015,5,13488；W.Zhang,H.Y.Ye,H.L.Cai,J.Z. Ge,R.G.Xiong S.D.Huang,J.Am.Chem.Soc.,2010,132,7300；Y.Zhang,W. Zhang,S.H.Li,Q.Ye,H.L.Cai,F.Deng,R.G.Xiong,S.D.Huang,J.Am.Chem.Soc., Study in 2012,134,11044.Due to the change of temperature, turning of the order-disorder of acid ion Change, the generation of phase transformation can be caused.This kind of hybrid inorganic-organic materials is through well-designed and regulation and control, Ke Yichong Divide the respective advantage utilizing inorganic material and organic material, reach the effect maximized favourable factors and minimized unfavourable ones, be that this type of material presents Go out the character of novelty.
1,4-diazabicylo [2,2,2] octane (Dabco) directly with the joining of some slaine or inorganic acid formation Position compound undergoes phase transition at low temperatures, and then shows good dielectric and ferroelectric property, therefore to Dabco The series phase transformation of complex, ferroelectricity Quality Research gradually increase.By pungent to 1,4-diazabicylo [2,2,2] Alkane is modified, and the triethylene diamine derivative of gained and slaine or inorganic acid form the phase with dielectric property Change compound, wherein conventional inorganic acid is perchloric acid and tetrafluoro boric acid.At present, Dabco is derived by people The research breadth and depth of thing is the most shallow, and different Dabco derivatives is produced from different ligands to be situated between Electrical property or phase transition property require further study developing.
Summary of the invention
Goal of the invention: in order to overcome the deficiencies in the prior art, the present invention provides a kind of containing hexafluoro-phosphate radical There are the molecular ion based compound of low temperature phase change character, preparation method and applications, by well-designed tune Control triethylene diamine derivative can make, to prepare, the compound that phase-change material uses with acid material, and further Expand the breadth and depth of this phase-change material application.
Technical scheme: for achieving the above object, the present invention by the following technical solutions:
A kind of low temperature phase change compound containing hexafluoro-phosphate radical, the chemical formula of this compound is C9H20P2F12N2。
Further, the construction unit of described compound is: at a temperature of 296K, crystal belongs to rhombic system, Space group is Pbca；At a temperature of 123K, crystal is monoclinic system, and space group is P21/c。
Present invention further proposes the preparation method of the above-mentioned low temperature phase change compound containing hexafluoro-phosphate radical, including Following steps: at normal temperatures, put in beaker by triethylene diamine derivative, are slowly added to distilled water stirring molten Solve, be subsequently placed in ventilating kitchen, be slowly added dropwise hexafluorophosphoric acid, while add the stirring of distillation waterside, then filter, take Subnatant, left at room temperature a period of time, i.e. obtains described by the crystallization self assembly of room temperature slow evaporating solution Low temperature phase change compound C9H20P2F12N2。
As preferably, described triethylene diamine derivative is that bromination 1-isopropyl-Isosorbide-5-Nitrae-diazabicylo [2.2.2] is pungent Alkane.
As preferably, described bromination 1-isopropyl-Isosorbide-5-Nitrae-diazabicylo [2.2.2] octane and hexafluorophosphoric acid mole Ratio is 1:2 4.
As preferably, described bromination 1-isopropyl-Isosorbide-5-Nitrae-diazabicylo [2.2.2] octane and hexafluorophosphoric acid The amount of material is respectively 10mmol and 20mmol, is used for dissolving bromination 1-isopropyl-Isosorbide-5-Nitrae-diazabicylo The volume of the distilled water of [2.2.2] octane is 10mL.
Present invention also offers the above-mentioned low temperature phase change compound containing hexafluoro-phosphate radical textile garment, chamber planting, Application in building trade field.
Beneficial effect: compared with prior art, the invention have the advantages that
(1) hexafluorophosphoric acid chosen, has the highest symmetry, at different temperature, hexafluoro-phosphate radical It is susceptible to the transformation of order-disorder, is easily caused the generation of phase transformation；
(2) bromination 1-isopropyl-Isosorbide-5-Nitrae-diazabicylo [2.2.2] octane selected is a kind of aminated compounds, Easily react with acid hexafluorophosphoric acid generation acid-base neutralization, improve the possibility of phase-change product synthesis.
(3) preparation method that the present invention provides is at ambient temperature, by solution nature solvent flashing from group Dress synthesis, material structure stability is higher, and the structural controllability of this compound is relatively strong, productivity is high and repeats Property good, preparation method is simple, easily operates, and the sufficient raw, the production cost that are used are low；
(4) the low temperature phase change compound that the present invention proposes, in textile garment, chamber planting, building trade etc. Field all has the application of the biggest potentiality.
Accompanying drawing explanation
Fig. 1 is the compounds of this invention C9H20P2F12N2Synthetic route chart；
Fig. 2 is chemicals C in embodiment 19H20P2F12N2Structure cell (Fig. 2 a 296K, figure at different temperatures 2b 123K) variation diagram；
Fig. 3 is compound C in embodiment 19H20P2F12N2The one-dimensional chain hydrogen bond structure figure formed；
Fig. 4 is compound C in embodiment 19H20P2F12N2Infrared spectrum；
Fig. 5 is compound C in embodiment 19H20P2F12N2Powder PXRD diffraction pattern；
Fig. 6 is compound C in embodiment 19H20P2F12N2Thermogravimetric TGA analysis chart；
Fig. 7 is compound C in embodiment 19H20P2F12N2Means of differential scanning calorimetry dsc analysis figure；
Fig. 8 is compound C in embodiment 19H20P2F12N2Jie under 100kHZ and 1MHZ frequency Electric scanning figure.
Detailed description of the invention
With embodiment, the present invention is further explained below in conjunction with the accompanying drawings.Fig. 1 is the compounds of this invention C9H20P2F12N2Synthetic route chart.Embodiment 1-4 prepares low temperature phase change compound according to this synthetic route.
Embodiment 1
At normal temperatures, 10mmol triethylene diamine derivative is put in beaker, be slowly added to 10ml distillation Water stirring and dissolving, is subsequently placed in ventilating kitchen, is slowly added dropwise 20mmol hexafluorophosphoric acid, while add 5ml distillation Waterside is stirred, and filters afterwards, takes its subnatant, left at room temperature a period of time, slowly volatilized by room temperature molten Liquid crystallization self assembly has the compound of low temperature phase change character described in i.e. obtaining.
Embodiment 2
At normal temperatures, 10mmol triethylene diamine derivative is put in beaker, be slowly added to 10ml distillation Water stirring and dissolving, is subsequently placed in ventilating kitchen, is slowly added dropwise 30mmol hexafluorophosphoric acid, while add 5ml distillation Waterside is stirred, and filters afterwards, takes its subnatant, left at room temperature a period of time, slowly volatilized by room temperature molten Liquid crystallization self assembly has the compound of low temperature phase change character described in i.e. obtaining.
Embodiment 3
At normal temperatures, 10mmol triethylene diamine derivative is put in beaker, be slowly added to 10ml distillation Water stirring and dissolving, is subsequently placed in ventilating kitchen, is slowly added dropwise 40mmol hexafluorophosphoric acid, while add 10ml distillation Waterside is stirred, and filters afterwards, takes its subnatant, left at room temperature a period of time, slowly volatilized by room temperature molten Liquid crystallization self assembly has the compound of low temperature phase change character described in i.e. obtaining.
Embodiment 4
At normal temperatures, 10mmol triethylene diamine derivative is put in beaker, be slowly added to 10ml distillation Water stirring and dissolving, is subsequently placed in ventilating kitchen, is slowly added dropwise 20mmol hexafluorophosphoric acid, while add 10ml distillation Waterside is stirred, and filters afterwards, takes its subnatant, left at room temperature a period of time, slowly volatilized by room temperature molten Liquid crystallization self assembly has the compound of low temperature phase change character described in i.e. obtaining.
Phase transition compound crystal prepared by embodiment 1 is analyzed, chooses suitable size under the microscope Monocrystalline, with through graphite monochromatised Mo K alpha ray during room temperatureAt Bruker Apex II Measuring the X-ray diffraction structure of monocrystalline on CCD diffractometer, the crystallographic parameter result of this phase transition compound is shown in Table 1.Carrying out semiempirical absorption correction by SADABS method, cell parameter least square method determines, number Using SAINT and SHELXL program bag to complete respectively according to reduction and structure elucidation, all non-hydrogen atoms are with complete Matrix least square method carries out anisotropy refine, and the unit cell of compound changes as shown in Figure 2.At 296K bar Under part (Fig. 2 a), structure cell also has an independent [C9H20N2]2+Cation, two hexafluoro-phosphate radical anion, Wherein having a hexafluoro-phosphate radical to be in disordered state, each F atom occupies two positions；Drop at a temperature of when During 123K (Fig. 2 b), containing two independent [C in structure cell9H20N2]2+Cation, four hexafluoro-phosphate radical the moon Ion, wherein has a hexafluoro-phosphate radical to be in disordered state, and triethylene diamine derivative ring there occurs distortion.
The crystallographic data of table 1 compound
Fig. 3 is compound C9H20P2F12N2One-dimensional chain hydrogen bond structure figure.Can be seen that from this structure chart [C9H20N2]2+Cation is connected with each other by N-H F and C-H F hydrogen bond with hexafluoro-phosphate radical, forms one Dimension chain hydrogen bond structure.
Infrared spectrum characterization to the compound in embodiment 1, as shown in Figure 4.At 3457cm-1Place, has One strong absworption peak, is the stretching vibration absworption peak of C-H singly-bound on triethylene diamine derivative；1428 cm-1There is a strong absworption peak, be the flexural vibrations absworption peak of C--C single bond.
Fig. 5 is the PXRD analysis and characterization to the compound in embodiment 1, can from powder PXRD diffraction pattern To find out, simulated diffraction peak and actual experiment record the fine of diffraction maximum contrast, illustrate that compound has the highest Phase purity.
Fig. 6 is that the thermogravimetric analysis to the compound in embodiment 1 characterizes, permissible from thermogravimetric analysis (TGA) Finding out, compound has the highest stability.But it is as the rising of temperature, at about 250 DEG C, chemical combination Triethylene diamine derivant structure in thing starts to cave in, and caves in completely to 400 DEG C of tiled configuration.
Use differential scanning calorimetric analysis (DSC) that the compound in embodiment 1 is carried out phase transition performance research, Specifically comprise the following steps that and weigh this compound 2.67mg, then survey at Perkin-Elmer Diamond DSC On examination instrument, testing under the speed that heating and cooling are 5K/min, the DSC scanning figure of this compound is such as Shown in Fig. 7.From Fig. 7, find, when lowering the temperature at 130.9K, have obvious exothermic peak, in intensification be During 135.4K, there is obvious endothermic peak, illustrate that what this compound occurred becomes single order phase transformation mutually.
Use dielectric scanning that the compound in embodiment 1 is carried out phase transition performance research, specifically comprise the following steps that choosing Take the sample that this compound is appropriate, tablet press machine be processed as the original shape testing sample that thickness is 0.5mm, In the both sides up and down of compressing tablet, coat conductive silver glue, then enterprising at Tonghui TH2828A measurement instrument Row test.This compound research obtained is found by we: in the frequency scanning of 100kHZ and 1MHZ Under, rise under gentle cooling mode, occur in that obvious reversible dielectric difference peak, this compound at about 140K Dielectric scanning result as shown in Figure 8.
Above description is for implementing some optimal modes of the present invention and other embodiments, simply to the present invention Technology design play description example effect, can not limit the scope of the invention with this, art technology Personnel, without departing from the spirit and scope of technical solution of the present invention, modify and equivalent, all should fall Within protection scope of the present invention.

Claims (7)

1. the low temperature phase change compound containing hexafluoro-phosphate radical, it is characterised in that: the chemistry of described compound Formula is C9H20P2F12N2。
Low temperature phase change compound containing hexafluoro-phosphate radical the most according to claim 1, it is characterised in that: The construction unit of described compound is: at a temperature of 296K, and crystal belongs to rhombic system, and space group is Pbca； At a temperature of 123K, crystal is monoclinic system, and space group is P21/c。
3. a preparation method for the low temperature phase change compound containing hexafluoro-phosphate radical according to claim 1, It is characterized in that: described preparation method comprises the steps: at normal temperatures, triethylene diamine derivative is put into In beaker, it is slowly added to distilled water stirring and dissolving, is subsequently placed in ventilating kitchen, is slowly added dropwise hexafluorophosphoric acid, slow Slow dropping distilled water stirring and dissolving, then filters, takes subnatant, left at room temperature a period of time, pass through room Temperature slowly evaporating solution crystallization self assembly i.e. obtains described low temperature phase change compound C9H20P2F12N2。
The preparation method of the low temperature phase change compound containing hexafluoro-phosphate radical the most according to claim 3, its It is characterised by: described triethylene diamine derivative is bromination 1-isopropyl-1,4-diazabicylo [2.2.2] octane.
5. according to the preparation method of the low temperature phase change compound containing hexafluoro-phosphate radical described in claim 3 or 4, It is characterized in that: described bromination 1-isopropyl-1,4-diazabicylo [2.2.2] octane and the mol ratio of hexafluorophosphoric acid For 1:2 4.
The preparation method of the low temperature phase change compound containing hexafluoro-phosphate radical the most according to claim 5, it is special Levy and be: described bromination 1-isopropyl-Isosorbide-5-Nitrae-diazabicylo [2.2.2] octane and hexafluorophosphoric acid material Amount is respectively 10mmol and 20-40mmol, is used for dissolving bromination 1-isopropyl-Isosorbide-5-Nitrae-diazabicylo [2.2.2] The volume of the distilled water of octane is 10mL.
7. the low temperature phase change compound containing hexafluoro-phosphate radical according to claim 1 and 2 is in weaving Application in clothes, chamber planting, building trade field.
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Cited By (4)

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CN110724275A (en) * 2019-10-21 2020-01-24 新疆农业大学 Molybdenum-based supermolecular phase-change crystal material and preparation method thereof
CN113429362A (en) * 2021-06-01 2021-09-24 南昌大学 Cyclic amine perchloric acid reversible phase-change material and preparation method thereof
CN113604204A (en) * 2021-07-27 2021-11-05 中国科学院金属研究所 Application of inorganic plastic crystal material in solid refrigeration
CN114085227A (en) * 2021-11-24 2022-02-25 江苏科技大学 High-temperature molecular-based phase change compound with switchable dielectric switch performance, preparation method and application

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110724275A (en) * 2019-10-21 2020-01-24 新疆农业大学 Molybdenum-based supermolecular phase-change crystal material and preparation method thereof
CN113429362A (en) * 2021-06-01 2021-09-24 南昌大学 Cyclic amine perchloric acid reversible phase-change material and preparation method thereof
CN113604204A (en) * 2021-07-27 2021-11-05 中国科学院金属研究所 Application of inorganic plastic crystal material in solid refrigeration
CN113604204B (en) * 2021-07-27 2022-05-31 中国科学院金属研究所 Application of inorganic plastic crystal material in solid refrigeration
CN114085227A (en) * 2021-11-24 2022-02-25 江苏科技大学 High-temperature molecular-based phase change compound with switchable dielectric switch performance, preparation method and application
CN114085227B (en) * 2021-11-24 2024-05-24 江苏科技大学 High Wen Fenzi-base phase change compound with switchable dielectric switch performance, preparation method and application

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