Liquid hydrogen storage material

Abstract

Disclosed is a liquid hydrogen storage material, and more particularly, a hydrogen storage material which contains m-phenyltoluene (m=2, 3) and undergoes reversible dehydrogenation/hydrogenation reactions or contains a binary eutectic mixture or a ternary eutectic mixture of m-phenyltoluene (m=2, 3, 4).

Claims

1. A liquid hydrogen storage material comprising a ternary eutectic mixture of m-phenyltoluene (m=2, 3, 4), wherein the ternary eutectic mixture of m-phenyltoluene has a molar ratio of 2-phenyltolyene: 3-phenyltoluene: 4-phenyltoluene=a: b: c (where a+b+c=1, a>0, b>0, and 0<c<0.4.

2. A liquid hydrogen storage material comprising a binary eutectic mixture selected from the group consisting of 2-phenyltoluene and 3-phenyltoluene, 2-phenyltoluene and 4-phenyltoluene or 3-phenyltoluene and 4-phenyltoluene, wherein the eutectic mixture of 2-phenyltoluene and 3-phenyltoluene among the binary eutectic mixtures has a molar ratio of 2-phenyltoluene: 3-phenyltoluene=0.001 to 0.999: 0.999 to 0.001, the eutectic mixture of 2-phenyltoluene and 4-phenyltoluene among the binary eutectic mixtures has a molar ratio of 2-phenyltoluene: 4-phenyltoluene=0.6 to 0.999: 0.4 to 0.001 and the eutectic mixture of 3-phenyltoluene and 4-phenyltoluene among the binary eutectic mixtures has a molar ratio of 3-phenyltoluene: 4-phenyltoluene=0.6 to 0.999: 0.4 to 0.001.

Description

BRIEF DESCRIPTION OF THE FIGURES

(1) The above and other objects and features of the inventive concept will become apparent by describing in detail exemplary embodiments thereof with reference to the accompanying drawings.

(2) FIG. 1 illustrates an apparatus for conducting a hydrogenation reaction to hydrogenate the hydrogen storage material of the inventive concept and measuring the hydrogen storage capacity;

(3) FIG. 2 illustrates the results for .sup.1H NMR analysis conducted after hydrogenation of the hydrogen storage material according to an embodiment of the inventive concept;

(4) FIG. 3 illustrates a dehydrogenation reaction apparatus for dehydrogenating a hydrogenated hydrogen storage material;

(5) FIG. 4 illustrates (a) the results for .sup.1H NMR analysis conducted after the dehydrogenation reaction of 2-phenyltoluene, which is a hydrogen storage material of the inventive concept, and (b) the results for the dehydrogenation reaction of 2-phenyltoluene with time;

(6) FIG. 5 illustrates the results for eutectic point prediction of a eutectic mixture of 2-phenyltoluene (2-PT) and 3-phenyltoluene (3-PT);

(7) FIG. 6 illustrates the results for eutectic point prediction of a binary eutectic mixture containing 2-phenyltoluene (2-PT) and 4-phenyltoluene (4-PT);

(8) FIG. 7 illustrates the results for eutectic point prediction of a binary eutectic mixture containing 3-phenyltoluene (3-PT) and 4-phenyltoluene (4-PT);

(9) FIG. 8 illustrates the results for eutectic point prediction of a ternary m-phenyltoluene (m=2, 3, 4) eutectic mixture;

(10) FIG. 9 illustrates the reaction conversion rate data obtained through the dehydrogenation reactions of hydrogenated 3-PT and 4-PT pure materials and a m-phenyltoluene (m=2, 3, 4) eutectic mixture (molar ratio of 2-PT:3-PT:4-PT=0.60:0.25:0.15) as a graph; and

(11) FIG. 10 illustrates the results for .sup.1H NMR analysis of the structures of products obtained after the synthesis, hydrogenation reaction, and then dehydrogenation reaction of a m-phenyltoluene (m=2, 3, 4) eutectic mixture (molar ratio of 2-PT:3-PT:4-PT=0.60:0.25:0.15).

DETAILED DESCRIPTION

(12) Below, the inventive concept will be more fully described with reference to accompanying drawings. First, it should be noted that the same component or part in drawings indicates the same reference marks/numeral so far as possible. In describing the inventive concept, the detailed description associated with a related known function or configuration is omitted to avoid the ambiguousness of the inventive concept.

(13) In the specification, the terms used to express the degree, such as approximately, about, and substantially, may be used as a meaning approximate to a numeral value when fabrication and material tolerance inherent to a mentioned meaning is suggested, and may be used to prevent an infringer from unconscientiously using the present disclosure in which an exact or absolute numerical value is mentioned for better understanding of the inventive concept.

(14) Embodiments of the inventive concept described herein relate to a liquid hydrogen storage material containing m-phenyltoluene (m=2, 3).

(15) 2-phenyltoluene (2-PT) and 3-phenyltoluene (3-PT) are present as a liquid substance at room temperature (25 C.). In other words, 2-phenyltoluene (2-PT) and 3-phenyltoluene (3-PT) are present as a liquid at room temperature as the melting point of 2-phenyltoluene (2-PT) is 0 C. and the melting point of 3-phenyltoluene (3-PT) is from 4 to 5 C.

(16) In addition, 2-phenyltoluene (2-PT) and 3-phenyltoluene (3-PT) maintain the liquid state even at a high temperature as the boiling point of 2-phenyltoluene (2-PT) is 255 C. and the boiling point of 3-phenyltoluene (3-PT) is 272 C., and it can be thus seen that the temperature range in which these can store hydrogen is wide.

(17) The m-phenyltoluene (m=2, 3), which is a hydrogen storage material of the inventive concept, can store hydrogen through hydrogenation, and the m-phenyltoluene (m=2, 3) can undergo reversible dehydrogenation/hydrogenation reactions.

(18) The hydrogenation/dehydrogenation reactions of m-phenyltoluene (m=2, 3) can reversibly take place as follows.

(19) ##STR00001##

(20) The hydrogen weight capacity can be 6.7 wt % when m-phenyltoluene (m=2, 3) is hydrogenated, and this is a higher hydrogen storage capacity than 5.8 wt % of NEC (N-ethylcarbazole) to be used as a conventional hydrogen storage material.

(21) FIG. 1 illustrates an apparatus for conducting a hydrogenation reaction to hydrogenate the hydrogen storage material of the inventive concept and measuring the hydrogen storage capacity.

(22) The hydrogenation reaction takes place by introducing m-phenyltoluene (m=2, 3), a catalyst and H.sub.2 into the reactor.

(23) A catalyst is required in the hydrogenation reaction, and either of Ru/Al.sub.2O.sub.3 or Ru/C may be used as the hydrogenation catalyst. A ruthenium-based catalyst may be utilized as the hydrogenation catalyst.

(24) In addition, the hydrogenation reaction using the hydrogen storage material of the inventive concept takes place at from 50 to 70 bar and from 150 C. to 180 C.

(25) In addition, the amount of the hydrogenation catalyst to be introduced into the reactor is preferably from 10 to 20 wt % of the mass (g) of m-phenyltoluene (m=2, 3) of the reactant.

(26) The hydrogen weight capacity to be stored using the hydrogen storage material of the inventive concept is 6.7 wt %, and this can be measured by using a hydrogen storage capacity measuring apparatus.

(27) The apparatus for conducting the hydrogenation reaction and measuring the hydrogen storage capacity may be equipped with 1) a temperature controller of a heating mantle, 2) a pressure gauge, 3) a reactor, 4) and 5) a hydrogen storage vessel, 6) a stirrer, and 7) a heating mantle.

(28) The temperature of 7) the heating mantle can be controlled by using 1) the temperature controller of the heating mantle. The heating mantle surrounds 3) the reactor, and the reaction can be conducted by raising the temperature to the desired temperature. 2) The pressure gauge measures the pressure of hydrogen in the reactor, and the hydrogen pressure decreases as the reaction takes place since the reaction is a hydrogenation reaction. It can be judged that the reaction has been completed when the pressure does not change any more.

(29) The measurement of hydrogen mass is conducted utilizing the principle of measuring the mass of hydrogen reacted in the reactor by the hydrogen pressure difference in the hydrogen storage vessel (reference cell).

(30) The volume of 5) the hydrogen storage vessel (reference cell) can be accurately measured by the mass difference of liquefied carbon dioxide. In the experiment of the inventive concept, the volume of 5) the hydrogen storage vessel (reference cell) was 213.68 mL. (V.sub.ref=213.68 mL)

(31) In the inventive concept, the experiment of hydrogenation reaction is conducted as follows.

(32) m-phenyltoluene (m=2, 3) of the reactant, a catalyst and H.sub.2 are injected into the reactor, then the pressure (P.sub.reac,1) in the reactor is set to 70 bar in a constant-temperature water bath (20 C.), and the pressure (P.sub.ref) in the reference cell is set to 100 bar and stabilized.

(33) Thereafter, the reactor is taken out from the constant-temperature water bath and then heated to from 150 C. to 180 C. by using a heating jacket, and the hydrogenation reaction is conducted.

(34) After the reaction is terminated, the pressure (P.sub.reac,2) in the reactor is stabilized in a constant-temperature water bath (20 C.).

(35) Thereafter, the hydrogen in the reference cell is injected into the reactor by using the metering valve, and the pressure in the reactor after the reaction is adjusted to P.sub.reac,1 of the pressure before the reaction (P.sub.reac,2.fwdarw.P.sub.reac,1).

(36) The mass of hydrogen can be determined by measuring the pressure (P.sub.reac,2) in the reactor after the reaction and calculating the amount of hydrogen reacted in the reactor using Equation (1).
m.sub.H.sub.2=[.sub.H.sub.3(T,P.sub.ref,1).sub.H.sub.2(T,P.sub.ref,2)]V.sub.refEquation 1

(37) : density of hydrogen, P.sub.ref,1: hydrogen pressure in 5) hydrogen storage vessel (before reaction), P.sub.ref,2: hydrogen pressure in 5) hydrogen storage vessel (after reaction), V.sub.ref: volume of 5) hydrogen storage vessel (213.68 ml)

(38) (Here, the hydrogen density data required for calculation of hydrogen mass refer to NIST TRC data)

(39) FIG. 2 illustrates the results for .sup.1H NMR analysis conducted after hydrogenation of the hydrogen storage material according to an embodiment of the inventive concept.

(40) FIG. 2 illustrates the results for .sup.1H NMR analysis conducted after 5 g of 2-phenyltoluene (2-PT) and 5 g of 3-phenyltoluene (3-PT) are hydrogenated using 0.5 g of Ru/Al.sub.2O.sub.3 as a catalyst at 160 C.

(41) As illustrated in FIG. 2, it is confirmed that complete hydrogenation takes place since the proton (H) peaks attributed to sp2-carbon of the aromatic ring at between 7 and 8 ppm all disappear and the peaks attributed to sp3-carbon newly appear at between 0 and 2.5 ppm through .sup.1H NMR analysis conducted after the hydrogenation reaction.

(42) The capacity at which hydrogen is stored after the hydrogenation has completely proceeded is 6.7 wt % of an ideal capacity.

(43) These results are presented in the following Table 1.

(44) TABLE-US-00001 TABLE 1 Feed(g) Reaction material/ Ideal Experimental Material Catalyst condition catalyst wt % wt % 2- Ru/Al.sub.2O.sub.3 160 C./ 5/0.5 6.7 wt % Confirmed phenyltoluene 30 min that material is completely hydrogenated through NMR analysis 3- Ru/Al.sub.2O.sub.3 160 C./ 5/0.5 6.7 wt % Confirmed phenyltoluene 30 min that material is completely hydrogenated through NMR analysis

(45) In addition, the hydrogen storage material of the inventive concept can be dehydrogenated when it is hydrogenated, and the dehydrogenation reaction can take place as a reverse reaction in the reaction formula since a reversible reaction is possible.

(46) FIG. 3 illustrates a dehydrogenation reaction apparatus for dehydrogenating a hydrogenated hydrogen storage material.

(47) Referring to FIG. 3, the dehydrogenation reaction apparatus is equipped with 1) a heating mantle, 2) a batch reactor, 3) a condenser, 4) a MFM, 5) an oil burette, and 6) a mass measuring device.

(48) When the dehydrogenation reaction takes place, the signals from the MFM and the mass measuring apparatus can be monitored in real time by using a computer to measure the hydrogen release rate. The mass of the oil from the oil burette is compared when a fixed amount of hydrogen is injected into the reactor in order to enhance the accuracy of quantitative measurement of hydrogen to be released in this manner.

(49) The dehydrogenation reaction is conducted as follows: the dehydrogenation reaction takes place and hydrogen is released when the hydrogenated material and the catalyst are introduced into 2) the reactor and the temperature thereof is raised. The release rate of hydrogen can be measured by using the MFM or oil burette and the mass measuring apparatus. The released hydrogen passes through 3) the condenser and 4) the MFM and pushes the oil in 5) the oil burette into the glass bottle on 6) the mass measuring apparatus. The oil pushed out changes the weight of the glass bottle on the mass measuring apparatus and this mass change can be measured in real time by using a computer. The total amount of hydrogen released during the dehydrogenation reaction can be obtained through such a mass measurement.

(50) The mass is measured using the oil pushed out, but this mass value does not match the amount of hydrogen released (volume of hydrogen: ml). The exact amount of hydrogen can be determined by calibration in order to confirm the correlation between the mass of the oil pushed out and the amount of hydrogen released (ml).

(51) In other words, the same condition as when the reaction actually takes place is maintained in a state (empty state) in which the catalyst and the reactant are not present in the reactor, a fixed amount of hydrogen is injected into the reactor, and the value indicated on the mass measuring apparatus is confirmed after the injection is completed. The correlation between the amount of hydrogen injected and the mass value measured using oil is confirmed through this. The mass value measured in the experiment of dehydrogenation reaction can be calibrated through this and the amount of hydrogen released can be accurately measured.

(52) In the dehydrogenation reaction, any one of Pd/C, Pd/Al.sub.2O.sub.3, Pt/C or Pt/Al.sub.2O.sub.3 may be used as the dehydrogenation catalyst. In the dehydrogenation reaction, palladium or a platinum-based catalyst is used.

(53) It is preferable that the dehydrogenation catalyst is contained at from 10 to 20 wt % of the material to be introduced into the reactor.

(54) In the dehydrogenation reaction, it is preferable that the reaction temperature is set to from 250 C. to 350 C.

(55) FIG. 4 illustrates (a) the results for .sup.1H NMR analysis conducted after the dehydrogenation reaction of 2-phenyltoluene, which is a hydrogen storage material of the inventive concept, and (b) the results for the dehydrogenation reaction of 2-phenyltoluene with time.

(56) In FIG. 4, the dehydrogenation reaction of hydrogenated 2-phenyltoluene (2-PT) is conducted at 250 C. for about 60 minutes using Pd/C as a dehydrogenation catalyst.

(57) Referring to (a) of FIG. 4, it is confirmed that the dehydrogenation reaction qualitatively takes place by confirming that the proton (H) peaks attributed to sp2-carbon of the aromatic ring appear again at between 7 and 8 ppm and, at the same time, the proton peaks attributed to the methyl group shift to 2.28 ppm of the original position through .sup.1H NMR analysis of dehydrogenated 2-phenyltoluene (2-PT).

(58) In addition, in (b) of FIG. 4, the black line in the graph indicates the hydrogen release rate measured by using MFM and the red line indicates the total amount of hydrogen determined by calibrating the mass measured by using the mass measuring apparatus. The percentage means the calibrated volume value of released hydrogen measured in an experiment with respect to the total amount of hydrogen (theoretical hydrogen volume) that can be released from 5 g of reaction sample, and 100% means that hydrogen in the reactant is completely dehydrogenated.

(59) It can be seen that 90% or more of the theoretical dehydrogenation amount is dehydrogenated when 30 minutes elapses from the start of dehydrogenation through this.

(60) Meanwhile, in the inventive concept, eutectic mixtures in which two or three m-phenyltoluenes (m=2, 3, 4) are mixed can be utilized as a hydrogen storage material.

(61) The melting points of 2-phenyltoluene, 3-phenyltoluene and 4-phenyltoluene are 0 C., from 4 to 5 C. and from 44 to 47 C., respectively, as presented in the following Table 2.

(62) TABLE-US-00002 TABLE 2 Hydrogen storage Melting Constituent capacity point material Constitutional formula (wt %) ( C.) 2- phenyltoluene 6.7 0 3- phenyltoluene 6.7 4 to 5 4- phenyltoluene 6.7 44 to 47

(63) The eutectic mixture can maintain the liquid state at room temperature when these two materials or three materials are appropriately mixed.

(64) A hydrogen storage material can be prepared by a binary system in which two materials are mixed.

(65) Hydrogen storage materials can be prepared by mixing (1) 2-phenyltoluene and 3-phenyltoluene, (2) 2-phenyltoluene and 4-phenyltoluene, and (3) 3-phenyltoluene and 4-phenyltoluene.

(66) First, among the binary eutectic mixtures, it is preferable that the molar ratio of 2-phenyltoluene to 3-phenyltoluene is 0.001 to 0.999:0.999 to 0.001. The eutectic mixture of 2-phenyltoluene and 3-phenyltoluene can maintain the liquid state at normal temperature even though these are mixed in all molar ratio ranges.

(67) In addition, it is most preferable that the molar ratio of 2-phenyltoluene to 3-phenyltoluene is 0.53:0.47, and the eutectic point at this time is 24.25 C. and the eutectic mixture can maintain the liquid state at a significantly low temperature.

(68) In addition, among the binary eutectic mixtures, it is preferable that the molar ratio of 2-phenyltoluene to 4-phenyltoluene is 0.6 to 0.999:0.4 to 0.001. The eutectic mixture of 2-phenyltoluene and 4-phenyltoluene maintains the liquid state at normal temperature when the molar ratio is in the above range. In addition, it is most preferable that the molar ratio of 2-phenyltoluene to 4-phenyltoluene is 0.77:0.23, and the eutectic point at this time is 10.75 C.

(69) In addition, among the binary eutectic mixtures, it is preferable that the molar ratio of 3-phenyltoluene to 4-phenyltoluene is 0.6 to 0.999:0.4 to 0.001. The eutectic mixture of 3-phenyltoluene and 4-phenyltoluene maintains the liquid state at normal temperature when the molar ratio is in the above range. In addition, it is most preferable that the molar ratio of 3-phenyltoluene to 4-phenyltoluene is 0.74:0.26, and the eutectic point at this time is 7.45 C.

(70) In addition, in the inventive concept, a hydrogen storage material can be prepared by a ternary system in which three materials are mixed.

(71) A eutectic mixture of 2-phenyltoluene, 3-phenyltoluene, and 4-phenyltoluene has a molar ratio of a:b:c, where the following relation may be satisfied: a+b+c=1, a>0, b>0, and c<0.4.

(72) In other words, the eutectic mixture of 2-phenyltoluene, 3-phenyltoluene and 4-phenyltoluene can maintain the liquid state at room temperature when 2-phenyltoluene and 3-phenyltoluene are appropriately mixed in a case in which the molar ratio of 4-phenyltoluene is less than 0.4.

(73) In addition, it is most preferable to mix 2-phenyltoluene, 3-phenyltoluene, and 4-phenyltoluene at a molar ratio of 0.47:0.41:0.12, the melting point of the eutectic mixture may fall to a maximum of 28.85 C. when these are mixed at the above molar ratio. In addition, the hydrogen storage capacity thereof is 6.7 wt %, which is higher than that of the conventional liquid hydrogen storage material, and the eutectic mixture can reversibly store and release hydrogen.

(74) The eutectic point of such a ternary system or binary system can be predicted by the thermodynamic relation. In other words, the eutectic point can be predicted by calculating the eutectic points of binary and ternary eutectic mixtures of 2-phenyltoluene, 3-phenyltoluene and 4-phenyltoluene using the thermodynamic relation.

(75) The thermodynamic relation is as follows.

(76) $\begin{array}{cc}{x}_i^l=\exp \frac{H_i^{\mathrm{sl}}}{{\mathrm{RT}}_{\mathrm{mi}}}\left(\frac{T-T_{\mathrm{mi}}}{T}\right)& \mathrm{Equation}\left(2\right)\end{array}$

(77) Here, R is an ideal gas constant, T.sub.mi is the melting point of each pure material, and H.sup.sl.sub.i is the heat of fusion of each pure material. The H.sup.sl.sub.i value is estimated through the Marrero and Gani group-contribution method.

(78) FIG. 5 illustrates the results for eutectic point prediction of a eutectic mixture of 2-phenyltoluene (2-PT) and 3-phenyltoluene (3-PT).

(79) When 2-phenyltoluene (2-PT) and 3-phenyltoluene (3-PT) are mixed at a molar ratio of 0.53:0.47, it can be predicted the eutectic point of the eutectic mixture is 24.25 C. and the eutectic mixture is present as a liquid even at temperatures to be considerably lower than the melting points of the respective pure materials.

(80) In addition, it can be seen that the eutectic mixture can maintain the liquid state at room temperature even though these are mixed in all molar ratio ranges.

(81) FIG. 6 illustrates the results for eutectic point prediction of a binary eutectic mixture containing 2-phenyltoluene and 4-phenyltoluene.

(82) In addition, FIG. 7 illustrates the results for eutectic point prediction of a binary eutectic mixture containing 3-phenyltoluene and 4-phenyltoluene.

(83) The melting point of 4-phenyltoluene is from 44 C. to 47 C., but the melting point may be lowered when being mixed with 2-phenyltoluene or 3-phenyltoluene.

(84) Referring to FIGS. 6 and 7, the eutectic mixture can be present as a liquid at room temperature when 2-phenyltoluene and 4-phenyltoluene or 3-phenyltoluene and 4-phenyltoluene are mixed and the molar ratio of 4-phenyltoluene is 0.4 or less.

(85) In addition, as the lowest eutectic point, the eutectic point is 10.75 C. when the molar ratio of 2-phenyltoluene to 4-phenyltoluene is 0.77:0.23 and the eutectic point is 7.45 C. when the molar ratio of 3-phenyltoluene to 4-phenyltoluene is 0.74:0.26.

(86) In addition, in the case of a ternary eutectic mixture in which three materials of 2-phenyltoluene (2-PT), 3-phenyltoluene (3-PT) and 4-phenyltoluene (4-PT) are mixed, the eutectic point can be generated at a temperature lower than the eutectic point of a eutectic mixture of 2-phenyltoluene and 3-phenyltoluene.

(87) In addition, it is confirmed from the results illustrated in FIGS. 6 and 7 that a binary eutectic mixture containing 4-phenyltoluene maintains the liquid state at normal temperature when the molar ratio of 4-phenyltoluene (4-PT) is less than 0.4. Accordingly, it is preferable that the molar ratio of 4-phenyltoluene (4-PT) is less than 0.4 when the inventive concept is a ternary m-phenyltoluene (m=2, 3, 4) eutectic mixture.

(88) FIG. 8 illustrates the results for eutectic point prediction of a ternary m-phenyltoluene (m=2, 3, 4) eutectic mixture.

(89) In FIG. 8, the green line indicates the solid-liquid phase equilibrium of eutectic mixtures at 19.85 C. In other words, a mixture having a molar composition inside the green line is present as a liquid at 19.85 C. In the same manner, the blue line indicates the solid-liquid phase equilibrium of eutectic mixtures at 24.85 C. A mixture having a molar composition inside the blue triangle is present as a liquid at 24.85 C. In addition, in case of mixing 2-phenyltoluene, 3-phenyltoluene and 4-phenyltoluene at a molar ratio of 0.47:0.41:0.12 (tertiary eutectic point), the solid-liquid phase equilibrium is obtained at 28.85 C. and it is confirmed that the eutectic mixture can be present as a liquid down to near this temperature.

(90) Meanwhile, a catalyst is required for hydrogenation/dehydrogenation of a binary or ternary hydrogen storage material of m-phenyltoluene (m=2, 3, 4), and it is possible to use the same materials as the catalysts described above.

(91) In other words, either of Ru/Al.sub.2O.sub.3 or Ru/C may be used as the hydrogenation catalyst to be used in the hydrogenation.

(92) In addition, any one of Pd/C, Pd/Al.sub.2O.sub.3, Pt/C or Pt/Al.sub.2O.sub.3 is used as the dehydrogenation catalyst to be used in the dehydrogenation.

(93) The hydrogenation reaction of a ternary eutectic mixture of m-phenyltoluene (m=2, 3, 4) may be conducted by using the apparatus illustrated in FIG. 1.

(94) For example, for hydrogenation, a m-phenyltoluene (m=2, 3, 4) eutectic mixture (molar ratio of 2-PT:3-PT:4-PT=0.60:0.25:0.15) and the Ru/Al.sub.2O.sub.3 catalyst are introduced into a reactor and the reactor is purged with hydrogen for 30 minutes. The temperature of the reactor is raised to 150 C. by using a heating jacket, and the hydrogen pressure in the reactor is adjusted to 60 bar. Stirring is conducted by using the magnetic stirrer in the reactor during the hydrogenation reaction. The reaction is continuously conducted until the pressure does not change any more, and then the catalyst and the product are separated from each other through filtration. The product is subjected to .sup.1H NMR analysis to judge whether the hydrogenation reaction has taken place.

(95) In addition, the dehydrogenation is conducted by using the apparatus illustrated in FIG. 3. The Pt/C catalyst is introduced into the reactor and then the reactor is heated to the desired temperature by using a heating mantle while purging the reactor with nitrogen. When the temperature reaches the reaction temperature (200 C., 250 C.), nitrogen purge is stopped and the reactor and the oil burette are connected to each other and stabilized. The m-phenyltoluene (m=2, 3, 4) eutectic mixture hydrogenated is injected into the batch reactor by using a syringe. Hydrogen generated by the dehydrogenation reaction pushes the oil out of the oil burette and the mass of the oil pushed out is measured in real time by using a mass measuring apparatus. The mass of the oil pushed out is converted to the volume of hydrogen generated. When there is no more change in the mass measuring apparatus, the reaction is terminated and the structural change of the product is determined through .sup.1H NMR analysis to judge whether the dehydrogenation reaction has taken place.

(96) FIG. 9 illustrates the reaction conversion rate data obtained through the dehydrogenation reactions of hydrogenated 3-PT and 4-PT pure materials and a m-phenyltoluene (m=2, 3, 4) eutectic mixture (molar ratio of 2-PT:3-PT:4-PT=0.60:0.25:0.15) as a graph.

(97) In the dehydrogenation experiment at 200 C., the reaction is completed within 30 minutes and the dehydrogenation conversion rate is from 40% to 50%. In the dehydrogenation experiment at 250 C., the reaction is completed within 20 minutes and the dehydrogenation conversion rate is from 85% to 95%. Hence, it is confirmed that the dehydrogenation reaction of hydrogenated m-phenyltoluene (m=2, 3) or a m-phenyltoluene (m=2, 3, 4) eutectic mixture is effective at a temperature of 250 C. or more. In addition, it is confirmed that dehydrogenation can proceed to a maximum of 95% at 250 C. to be relatively lower than a temperature of 300 C. or more that is the temperature for dehydrogenation reaction of conventional hydrocarbons.

(98) FIG. 10 illustrates the results for .sup.1H NMR analysis of the structures of products obtained after the synthesis, hydrogenation reaction, and then dehydrogenation reaction of a m-phenyltoluene (m=2, 3, 4) eutectic mixture (molar ratio of 2-PT:3-PT:4-PT=0.60:0.25:0.15).

(99) Referring to FIG. 10, the pure component ratio in the eutectic mixture after being synthesized can be judged by comparing the areas of the methyl group peaks with one another. It is confirmed that the methyl group peak of 2-phenyltoluene appears at 2.312 ppm, the methyl group peak of 3-phenyltoluene appears at 2.457 ppm, and the methyl group peak of 4-phenyltoluene appears at 2.431 ppm.

(100) It is confirmed that the aromatic proton peaks at from 7 to 8 ppm all shift to the aliphatic proton peaks at from 0.5 to 2 ppm when the m-phenyltoluene (m=2, 3, 4) eutectic mixture synthesized is hydrogenated, and this means that the hydrogenation completely (100%) proceeds.

(101) In addition, from the results for structural analysis conducted after the dehydrogenation reaction at 250 C., it is confirmed that the proton (H) peaks attributed to sp2-carbon of the aromatic ring appear again at between 7 and 8 ppm and, at the same time, the proton peaks attributed to the methyl group shift to 2.28 ppm of the original position, and it is confirmed that the dehydrogenation reaction qualitatively takes place through this.

(102) Consequently, binary and ternary m-phenyltoluene (m=2, 3, 4) eutectic mixtures of the hydrogen storage material according to the inventive concept can maintain the liquid state at a low temperature, and particularly, a ternary eutectic mixture has a eutectic point at a maximum of 28.85 C.

(103) In addition, it can be seen that the binary and ternary m-phenyltoluene (m=2, 3, 4) eutectic mixtures have a high hydrogen storage capacity of 6.7 wt % and can reversibly undergo the hydrogenation/dehydrogenation reactions. In addition, it can be seen that the dehydrogenation reaction of the hydrogenated m-phenyltoluene (m=2, 3, 4) eutectic mixtures of the inventive concept smoothly takes place even at a relatively low temperature of 250 C. while a high temperature of 300 C. or more is required for the dehydrogenation reaction of conventional hydrocarbon materials.

(104) While the inventive concept has been described with reference to exemplary embodiments thereof, it will be apparent to those of ordinary skill in the art that various changes and modifications may be made thereto without departing from the spirit and scope of the inventive concept as set forth in the following claims.