WO2011000989A1 - Organic/inorganic microporous crystalline material based on alkaline-earth cations, preparation method and uses - Google Patents

Abstract

The present invention relates to a family of organic/inorganic microporous crystalline materials containing alkaline-earth cations and dicarboxylic acids, the method for preparation thereof and the use thereof as reusable heterogeneous catalysts for reactions in organic chemistry, as molecular sieves and as gas and liquid absorbents.

Description

 ORGANIC-INORGANIC MICROPOROUS CRYSTAL MATERIAL BASED ON ALKALINOTERAL CATIONS, PROCEDURE FOR

 PREPARATION AND USES The present invention relates to a family of crystalline microporous organ-inorganic materials containing alkaline earth cations and dicarboxylic acids, their preparation process and their use as reusable heterogeneous catalysts for reactions in organic chemistry, as molecular sieves and as gas absorbers and liquids

STATE OF THE TECHNIQUE

Nanostructured organ-inorganic hybrid materials, also called MOFs (Metal-Organic Frameworks), have demonstrated their potential use as multifunctional crystalline materials with interesting properties and promising applications over the past few years. As an example, it is worth mentioning the use of such materials as heterogeneous catalysts, molecular sieves, gas absorbers, LED emitters and their most recent application in controlled drug release (B. Wang et al., Nature. 2008. 453 , 207; F. Gándara et al., Cryst. Growth Des. 2008, 8, 2, 378; P. Horcajada et al., J. Am. Chem. Soc. 2008. 130, 6774). Currently, many research groups are trying to prepare MOFs with new structures and composition that lead to the substantial improvement of the properties of these systems.

During the last years, the use of divalent and trivalent cations derived from transition metals and, more recently, from rare earths, has resulted in the preparation of a great variety of this family of microporous crystalline materials. However, if we extend our search to MOFs based on alkaline earth cations, we find few reported examples (RKB Nielsen et al., Solid State Science. 2006, 8, 1237; C. Vo Ikringer et al., Solid State Science. 2007, 9, 455; C. Volkringer et al., Cryst. Growth Des. 2008, 8, 658; S. Chen et al., Anorg. AIIg. Chem. 2008. 634, 1591; CA Williams et al., Cryst. Growth Des. 2008, 8 (3), 911), despite the interesting properties of sorption (O ₂ , H ₂ , CO ₂ ) (M. Dinca et al., J. Am. Chem. Soc. 2005, 127, 9376) and catalytic behavior (J. Spielmann et al., Angew. Chem. Int. Ed. 2008, 47, 9434) that offer these elements.

More specifically, it should be noted that MOFs have been proposed as a new class of heterogeneous catalysts, due, above all, to:

 - First, MOFs have a good dispersion of catalytically active centers, because they are part of an organic matrix.

 - Secondly, a large number of these compounds have micro or mesoporism, which not only favors the catalytic activity but also has a very significant influence on the selectivity.

 - In addition, due to the hybrid nature of these organo-inorganic materials, these are proposed as potential bifunctional catalysts, taking advantage of the acid-base characteristics of the organic ligands and the reactive properties of the metals.

 - On the other hand, these types of compounds are mainly indicated for reactions in fine chemistry and obtaining products with high added value, since these are carried out under mild conditions.

Therefore, and as will be shown throughout the report, the design of MOFs-type systems based on alkaline earth cations and possessing catalytic and sorption properties is presented as a low-cost alternative and, above all, a lower environmental impact, compared to the systems currently used at industrial level. Table 1 shows the metals on which commonly used catalysts are based, for some of the most demanded reactions at the industrial level.

Entre los más importantes, Ia industria petroquímica utiliza anualmente grandes cantidades de metales preciosos soportados en diversos materiales porosos, como sílice o sales inorgánicas divididas (CaCOs), como catalizador de reacciones de hidrogenación, especialmente de olefinas. DESCRIPCIÓN DE LA INVENCIÓN Table 1

Among the most important, the petrochemical industry annually uses large amounts of precious metals supported in various porous materials, such as silica or divided inorganic salts (CaCOs), as a catalyst for hydrogenation reactions, especially olefins. DESCRIPTION OF THE INVENTION

Therefore, in a first aspect, the present invention refers to an AEPF crystalline microporous organ-inorganic material, of the English Alkaline Earth Polymeric Framework (from now on material of the invention), characterized in that it presents as a repeating unit the following formula generic:

[M (HOOC-R-COOH) _x (OOC-R-COO) _and (H ₂ O) ₂ nA] where:

 - M is an alkaline earth cation, in oxidation state +2,

 - A is a host molecule, comprising a solvent selected from the list comprising ethanol, propanol, butanol, toluene, cyclohexane, hexane, heptane, octane, pyridine and any combination thereof, from the reaction medium,

 - R is an organic group, preferably it is an aromatic group selected from phenyl, naphthyl or diphenyl, which is branched or not with other groups, that is, an isolated or several aromatic group linked together by means of an alkyl (Ci-Cβ) ) linear or branched, which in turn may be substituted, preferably substituted by a halogen,

- x represents a value less than or equal to 4 (x <4), preferably less than 2 (x <2),

 - and represents a value between 0.5 and 2, (0.5≤ and ≤2),

- z represents a value between O and 4, (O <z <4) and - n is the number of host molecules and represents a value between 0 and 4 (0 <n <4), preferably between 0 and 2 (0 <n <2).

The term "alkyl" refers, in the present invention, to aliphatic, linear or branched chains, having 1 to 6 carbon atoms, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, tere-butyl, sec-butyl, n-pentyl, n-hexyl, etc. Preferably, the alkyl group has between 1 and 4 carbon atoms. The alkyl groups may be optionally substituted by one or more substituents such as halogen, hydroxyl, azide or carboxylic acid.

By "halogen" is meant, in the present invention, an atom of bromine (Br), chlorine (Cl), iodine (I) or fluorine (F), preferably fluorine (F).

In a preferred embodiment, M is selected from Mg, Ca, Sr or Ba.

In another preferred embodiment, A is a solvent selected from the list comprising ethanol, propanol, butanol, toluene, cyclohexane, hexane, heptane, octane, pyridine or any combination thereof. In another preferred embodiment, R is represented by the general formula Ri-C (R ₂ ) ₂ -Ri, where Ri is an aromatic group selected from phenyl, naphthyl or diphenyl and R ₂ is a group selected from methyl, ethyl, Isopropyl, terbutyl or CF3. Preferably, Ri is a phenyl group and R ₂ is a CF3 group and, therefore, R is represented by:

In another preferred embodiment, the ratio x: y: z is 0.5: 1: 1 and n represents a value between 0 and 2 (0 <n <2). "AEPF crystalline microporous organ-inorganic materials" in the present invention means those nanostructured hybrid organ-inorganic materials, also called MOFs (from English, Metal-Organic Frameworks), which have demonstrated their potential use over the last few years. as multifunctional crystalline materials with interesting properties and promising applications. These MOFs are crystalline compounds that consist of metal ions or clusters often coordinated to rigid organic molecules to form structures of one, two or three dimensions that can be porous. In some cases, the pores are stable to the elimination of host molecules (often solvents) and can be used for the storage of gases such as hydrogen and carbon dioxide. MOFs are also known as hybrid and polymer coordination matrices, although these terms are not strictly identical.

Scheme 1 represents in a generic way the family of carboxylic acids components of AEPF.

HOOC R COOH

 Scheme 1

In Scheme 2 a preferred embodiment of the family of carboxylic acids components of AEPF is represented, where R is a diphenyl as described above:

Scheme 2 In a preferred embodiment, in the chemical composition of the organo-inorganic material of the invention, M is Ca, the ratio x: y: z is 0.5: 1: 1 and n is less than 1 (n <1). More preferably, the organ-inorganic material of the invention is AEPF-1, and is represented by the following unit of repetition of empirical formula:

[Ca (Ci ₇ H ₁₀ O ₄ F ₆ ) _X (Ci ₇ H ₈ O ₄ F ₆ ) _and (H ₂ O) _z -nA]

 where:

 - x represents a value of 0.5,

 - and represents a value of 1,

 - z represents a value of 1,

 - n represents a value of 0.7 and

 - A is selected from ethanol, propanol, butanol, toluene, cyclohexane, hexane, heptane, octane or any combination thereof. Preferably propanol, and even more preferably isopropanol.

In another more preferred embodiment, the chemical composition of the organo-inorganic material of the invention, AEPF-2, is represented by the following unit of repetition of empirical formula:

[Ca (Ci ₇ HioO ₄ F ₆ ) _x (Ci ₇ H ₈ O ₄ F ₆ ) _and (H ₂ O) _Z ] where:

 - x represents a value of 0.5,

 - and represents a value of 1,

 - z represents a value of 1,

 - n represents a value of 0.

In another preferred embodiment, in the chemical composition of the organo-inorganic material of the invention, M is Sr, the ratio x: y: z is 0.5: 1: 1, n is less than 1 (n <1) and A It is pyridine. More preferably, the organ-inorganic material of the invention is AEPF-3, and is represented by the following unit of repetition of empirical formula:

[Sr (Ci ₇ H ₁₀ O ₄ F ₆ ) _X (Ci ₇ H ₈ O ₄ F ₆ ) _and (H ₂ O ^ nC ₅ H ₅ N] where:

- x represents a value of 0.5, - and represents a value of 1,

 - z represents a value of 1,

 - n represents a value between 0 and 1 (0 <n≤ 1). In a second aspect, the present invention relates to a process for preparing the organ-inorganic material of the invention (from now on the method of the invention), which comprises:

 a) preparation of a reaction mixture comprising:

 an alkaline earth cation M,

- a HOOC-R _r C (R ₂ ) ₂ -Ri-COOH dicarboxylic acid, where Ri is an aromatic group selected from phenyl, naphthyl or diphenyl and R ₂ is a group selected from methyl, ethyl, isopropyl, terbutyl or CF ₃ , preferably in salt form,

- a host molecule A, which comprises a solvent selected from the list comprising ethanol, propanol, butanol, toluene, cyclohexane, hexane, heptane, octane, pyridine and any combination thereof, which comes from the reaction medium and

 - Water;

 b) heat treatment of the reaction mixture of stage (a) at a temperature between 80 ° C and 220 ° C, until its crystallization is achieved.

In a preferred embodiment of the process of the invention, the reaction mixture has a composition, in terms of molar ratios, between the intervals:

 - M / dicarboxylic acid = 0.25-1

- H ₂ O / S = 4.5-10.3

- H ₂ O / M = 300-800

In another preferred embodiment of the process of the invention, the heat treatment to which the reaction mixture is subjected in step (b) is carried out at a temperature between 100 ° C and 200 ° C. Preferably, the heat treatment is carried out at a temperature between 130 ° C and 180 ° C. Said heat treatment can be performed in static or with agitation of the mixture. Once the crystallization is finished, the crystalline product is filtered off, washed with water and common organic solvents and air dried.

Therefore, another preferred embodiment of the process of the invention also includes:

 c) separation, washing and heat treatment of the crystalline product obtained in stage (b) at a temperature between 40 ° C and 150 ° C.

More preferably, the stage of separation, washing and heat treatment of the crystalline product obtained in stage (b) is carried out at a drying temperature of between 100 ° C and 120 ° C and under vacuum for a time between 10 and 2O h.

Thermogravimetry analysis determines the content (n) of A when the material is heated at temperatures up to 150 ° C in an inert atmosphere of N ₂ .

The IR spectroscopy technique allows the characterization of these materials. Thus, the IR spectra of these materials can be recorded in the transmission mode by preparing wafers of these solids that are transparent to infrared radiation by compression at pressures between 1 and 10 Tm x cm ² for a time between 1 and 5 min.

X-ray diffraction demonstrates the purity and crystallinity of the material.

The surface area of these materials can be determined by gas adsorption isotherms (N ₂ and Ar) by applying Langmuir algorithms. In a final aspect, the present invention refers to the use of the organ-inorganic material of the invention as a catalyst in a process of conversion of compounds, which comprises contacting a feed of compounds, as substrates, with an amount of the material of the invention and other reactive compounds.

In a more preferred embodiment, the compound conversion process is a hydrogenation of alkenes using H ₂ as a reducing agent. (Scheme 3).

 Scheme 3

 Where R, R ', R ", R'" represent alkyl or aryl groups.

In another more preferred embodiment, the compound conversion process is a hydroformylation of alkenes. (Scheme 4).

 Scheme 4

 Where R represents an alkyl or aryl group

In another more preferred embodiment, the compound conversion process is a hydrosilylation of aldehydes using as a reagent an organic compound derived from silane. (Scheme 5).

 Scheme 5

 Where R, R ', R ", Ri represent alkyl or aryl groups.

In another more preferred embodiment, the compound conversion process is a hydrosilylation of ketones using as a reagent an organic compound derived from the silane. (Scheme 6).

Scheme 6

 Where R, R ', R ", Ri, R2 represent alkyl or aryl groups.

In another more preferred embodiment, the compound conversion process is a hydrosilylation of alkenes using as a reagent an organic compound derived from the silane. (Scheme 7).

 Scheme 7

Where R, R ', R ", Ri, R ₂ represent alkyl or aryl groups. In another more preferred embodiment, the compound conversion process is an intermolecular hydroamination of linear aminoalkenes.

Esquema 8

Scheme 8

 where Ri represents an alkyl group.

In another aspect, the present invention refers to the use of the organo-inorganic material of the invention as a selective absorbent component of compounds, which comprises contacting a feed of a mixture of compounds, including isomers, with an amount of the material of the invention .

In another aspect, the present invention refers to the use of the organo-inorganic material of the invention as a selective molecular sieve, which comprises contacting a feed of a mixture of compounds, including isomers, with an amount of the material of the invention passing through said material only those molecules that by their shape and / or size can do so, retaining the others.

In another aspect, the present invention refers to the use of the organo-inorganic material of the invention as a controlled drug delivery system.

Those skilled in the art will assess that the present invention can be carried out within a wide range of parameters, concentrations and equivalent conditions without departing from the spirit and scope of the invention and without undue experimentation. While this invention has been described in relation to said embodiments, it is understood that it may be subject to further modifications. This document is intended to cover any variant, use or adaptation of the invention following the general principles of The same and including the variants coming from the present disclosure, such as the known or customary practices of the technical sector to which the invention belongs. DESCRIPTION OF THE FIGURES

Fig. 1. Shows the powder X-ray diffraction pattern for the AEPF-1 compound. Fig. 2. Shows the powder X-ray diffraction pattern for the AEPF-2 compound.

Fig. 3. Shows the powder X-ray diffraction pattern for the AEPF-3 compound.

Fig. 4. Shows the structural view of the AEPF-1 compound. The molecules of the host organic compound have been removed from the figure for greater understanding of the structure. EXAMPLES

The following examples are presented as an additional guide for the average expert in the field and in no case should they be considered as a limitation of the invention. These tests carried out by the inventors show the specificity and effectiveness of the microporous crystalline organ-inorganic AEPF material object of the present invention.

Example 1. Synthesis of AEFP-1 A solution of H ₂ L (400 mg, 1 mmol) in 9 ml of isopropanol (Propan-2-ol, CH ₃ CH (OH) CH ₃ ) is mixed with another solution of Ca ( CH ₃ CO ₂ ) ₂ -4 H ₂ O (178 mg, 1 mmol) in 10 ml of distilled water, under continuous and vigorous stirring. The resulting dispersion is heated at 170 ° C, under autogenous system pressure, for 72 h. Then, the mixture is rapidly cooled to room temperature. The product is filtered and washed successively with distilled water and acetone.

Scheme 2 depicts the carboxylic acid component of AEPF-1, referred to as H ₂ L from now on. In AEPF-1, the X-ray diffraction pattern of [Ca (C _{25 5} F ₉ O ₆ Hi ₅ ) 0.7C ₃ H ₇ O] as synthesized, obtained by the powder method using a divergence slit Fixed, with a Bruker Advance equipment equipped with copper anti-cathode, it is characterized by the angular values, the corresponding inter-planar spacings (d) and the relative intensities (1/10) shown in Table 2 and in Figure 1. An estimated 0.3 ° discrepancy, depending on the alignment of the equipment, the crystallinity of the sample and degree of purity.

The structure of the AEPF-1 material has been determined by monocrystalline X-ray diffraction. It belongs to the monoclinic crystalline system, spatial group P 2 / n and the cell parameters are: a = 18,791 (1) A, b = 7,5961 (5) A, c = 20,9987 (5) A, β = 104, 6 (1) °.

Following the same procedure, replacing propanol with butanol (C4H10O), toluene (methylbenzene, CeH ₅ CH ₃ ), hexane (CeHi ₄ ) heptane (C ₇ Hi ₆ ), octane (C ₈ Hi ₈ ), the respective AEPF compound is obtained -1 isostructural, [Ca (C _{25 5} FgOeHi ₅ ) nA] (0 <n <1), with a slight variation in the relative intensity of the diffraction peaks due to the variation in composition according to A used. Example 2. Synthesis of AEFP-2 Through a drying process, between 100 ° C and 120 ° C and under vacuum for a time between 10 and 20 h, the AEPF-1 compound is obtained. Scheme 2 depicts the carboxylic acid component of AEPF-2.

In AEPF-2, the X-ray diffraction pattern of [Ca (C255F ₉ θ6Hi ₅ )] as synthesized, obtained by the powder method using a fixed divergence slit, with a Bruker Advance equipment equipped with an anti-cathode of copper, is characterized by angular values, corresponding inter-planar spacings (d) and relative intensities (1/10) shown in Table 3 and Figure 2. A discrepancy of 0.3 ° is estimated, depending on the alignment of the equipment , The crystallinity of the sample and degree of purity. The spatial group and cell parameters of the AEPF-2 material have been determined by X-ray diffraction of the polycrystalline sample. It belongs to the monoclinic crystalline system, spatial group P 2 / c and the cell parameters are: a = 24,614 (1) A, b = 7,367 (5) A, c = 31,519 (5) A, β = 89,858 (1) °. Example 3. Synthesis of AEFP-3

101 mg of H ₂ L (1 mmol) and 51 mg of Sr (CH ₃ C 2) 2 are added to a mixture of 10 ml of H ₂ O and 0.5 ml of pyridine (C ₅ H ₅ N). The resulting mixture is heated at 180 ° C, under autogenous system pressure, for 48 h. Then, the mixture is rapidly cooled to room temperature. The product is filtered and washed successively with distilled water and acetone. The diffraction pattern of the solid obtained white is shown in Figure 3.

In AEPF-3, the X-ray diffraction pattern of [Sr (C _{25 5} F ₉ O ₆ Hi ₅ ) nC ₅ H ₅ N] (0 <n <1) as synthesized, obtained by the method of powder using a Fixed divergence slit, with a Bruker Advance equipment equipped with copper anti-cathode, is characterized by the angular values, the corresponding inter-planar spacings (d) and the relative intensities (I / lo) shown in Table 4 and Figure 3. It is estimated a discrepancy of 0.3 °, depending on the alignment of the equipment, the crystallinity of the sample and degree of purity.

The structure of the AEPF-3 material has been determined by single crystal X-ray diffraction. They belong to the monoclinic crystalline system, spatial group P 2 / n and the cell parameters are: a = 18,588 (1) A, b = 7,8223 (5) A, c = 21, 399 (1) A, β = 105, 9 (1) °.

Table 2

10

 fifteen

 twenty

 25

30 10

 fifteen

 twenty

25

30 Table 3

10

 fifteen

 twenty

 25

30 10

 fifteen

 twenty

25

30 Table 4

10

 fifteen

 twenty

 25

30 10

fifteen

twenty

Example 4. Application

Hydrogenation of alkenes

Hydrogenation of styrene (vinylbenzene, CsH ₈ ) with H ₂ (Scheme 7) is achieved with 100% selectivity and 100% alkene conversion by treating a mixture of alkene dissolved in toluene with a pressure of H ₂ of 5 atm, in the presence of the catalyst of Example 1 in a catalyst / alkene ratio of 1 mol%. The reaction temperature can vary between room temperature and 100 ° C, achieving an optimum speed at 70 ° C.

 Scheme 9

 Example 5. Application

Aldehyde Hydrosilylation

Hydrosilylation of benzaldehyde (CeH ₅ CHO) with diphenylsilane (Scheme 8) is achieved with 100% selectivity and 100% aldehyde conversion by treating a mixture of aldehyde and silane in a ratio of 1: 2 dissolved in dry toluene in the presence of the catalyst of Example 1 in a

relación catalizador/aldehido del 10% molar.

10% molar catalyst / aldehyde ratio.

 Scheme 10

Example 6. Hydrosilylation application of ketones

Hydrosilylation of acetophenone with diphenylsilane (Scheme 9) achieves 100% selectivity and conversion of acetophenone greater than 70% by treating a mixture of ketone and silane in a ratio of 1: 2 dissolved in dry toluene at 90 ° C, in the presence of the catalyst of Example 1 in a catalyst / acetone ratio of 10 mol%.

 Scheme 11

Example 7. Application

Alkene Hydrosilylation

Hydrosilylation of styrene with diphenylsilane (Scheme 10) achieves 100% selectivity to the linear product and conversion of 100% alkene by treating a mixture of alkene and silane in a 3: 1 ratio dissolved in dry toluene at 90 ° C, in the presence of the catalyst of Example 1 in a catalyst / alkene ratio of 10 mol%.

 Scheme 12

 Example 8. Application

Intermolecular hydroamination of alkenes.

Scheme 13

The intermolecular hydroamination of 1-amino-2,2-dimethylhex-5-ene (Scheme 13) is achieved in 2 hours, with 100% selectivity, in benzene at 80 ⁰ C, in the presence of the catalyst of Example 1 in a ratio of 10% molar catalyst / aminoalkene.

Claims

1. Organ-inorganic material of formula: [M (HOOC-R-COOH) _x (OOC-R-COO) _and (H ₂ O) ₂ nA]  where:  M is an alkaline earth cation,  - A is a host molecule, which comprises a solvent selected from the list comprising ethanol, propanol, butanol, toluene, cyclohexane, hexane, heptane, octane, pyridine and any combination thereof,  R is an aromatic group selected from phenyl, naphthyl or diphenyl, which is branched or not with other groups,  - x represents a value less than or equal to 4,  - and represents a value between 0.5 and 2,  - z represents a value between O and 4 and  n represents a value between O and 4. 2. Material according to claim 1, wherein M is selected from Mg, Ca, Sr or Ba. 3. Material according to any of claims 1 or 2, wherein the ratio x: y: z is 0.5: 1: 1 and n represents a value between O and 2. 4. Material according to any of claims 1 to 3, wherein R is represented by the general formula Ri-C (R ₂ ) ₂ -Ri, where Ri is an aromatic group selected from phenyl, naphthyl or diphenyl and R ₂ is a group selected from methyl, ethyl, isopropyl, terbutyl or CF ₃ . 5. Material according to claim 4, wherein Ri is a phenyl group and R ₂ is a CF ₃ group, and is represented by:

6. Material according to any of claims 1 to 5, of formula: [Ca (CI ₇ HI ₀ O ₄ F ₆ ) X (Ci ₇ H ₈ O ₄ F6) and (H ₂ O) _z -nA] where:  - x represents a value of 0.5,  - and represents a value of 1,  - z represents a value of 1,  - n represents a value of 0.7 and  - A is selected from ethanol, propanol, butanol, toluene, cyclohexane, hexane, heptane, octane or any combination thereof. 7. Material according to any of claims 1 to 6, of formula: [Ca (Ci ₇ HioO ₄ F ₆ ) _x (Ci ₇ H ₈ O ₄ F ₆ ) _and (H ₂ O) _Z ] where:  - x represents a value of 0.5,  - and represents a value of 1,  - z represents a value of 1,  n represents a value of 0. 8. Material according to any of claims 1 to 7, of formula: [Sr (Ci ₇ H ₁₀ O ₄ F ₆ ) _X (Ci ₇ H ₈ O ₄ F ₆ ) _and (H ₂ O ^ nC ₅ H ₅ N] where:  - x represents a value of 0.5, - and represents a value of 1, - z represents a value of 1,  - n represents a value between 0 <n <1.  9. Procedure for preparing the material according to any of the  claims 1 to 8, comprising:  a) preparation of a reaction mixture comprising:  - an alkaline earth cation M, - a HOOC-Ri-C (R ₂ ) ₂ -Ri-COOH dicarboxylic acid, where Ri is an aromatic group selected from phenyl, naphthyl or biphenyl , and _R2 is a group selected from methyl, ethyl, isopropyl, tert - butyl or CF _3,  - a host molecule A, comprising a solvent selected from the list comprising ethanol, propanol, butanol, toluene, cyclohexane, hexane, heptane, octane, pyridine and any combination thereof and  - Water;  b) heat treatment of the reaction mixture of stage (a) at a temperature between 80 ° C and 220 ° C until its crystallization is achieved. 10. Process according to claim 9, wherein in the dicarboxylic acid HOOC-Ri-C (R ₂ ) 2-Ri-COOH, Ri is a phenyl group and R ₂ is a CF ₃ group. 11. Method according to any of claims 9 or 10, wherein the dicarboxylic acid of the reaction mixture of step (a) is in the form of salt. 12. Method according to any of claims 9 to 11, wherein the reaction mixture has a composition, in terms of molar ratios, comprised between the intervals:  - M / dicarboxylic acid = 0.25-1 - H ₂ O / S = 4.5-10.3 - H ₂ O / M = 300-800 13. Method according to any of claims 9 to 12, wherein the heat treatment to which the reaction mixture is subjected in stage (b) is carried out at a temperature between 130 ° C and 200 ° C. 14. Method according to any of claims 9 to 13, further comprising:  a) separation, washing and heat treatment of the crystalline product obtained in stage (b) at a drying temperature between 40 ° C and 150 ° C. 15. Method according to claim 14, wherein the separation, washing and heat treatment of the crystalline product obtained in step (b) is carried out at a drying temperature of between 100 ° C and 120 ° C and under vacuum for a period of between 10 and 20 h. 16. Use of the material according to any of claims 1 to 8 as a catalyst in a compound conversion process. 17. Use of the material according to claim 16, wherein the compound conversion process is a hydrogenation of alkenes using H ₂ as reducing agent. 18. Use of the material according to claim 16, wherein the process of conversion of compounds is a hydroformylation of alkenes. 19. Use of the material according to claim 16, wherein the process of conversion of compounds is a hydrosilylation of aldehydes using as reagent an organic compound derived from silane. 20. Use of the material according to claim 16, wherein the process of conversion of compounds is a hydrosilylation of ketones using as reagent an organic compound derived from silane. 21. Use of the material according to claim 16, wherein the process of conversion of compounds is a hydrosilylation of alkenes using as reagent an organic compound derived from silane. 22. Use of the material according to claim 16, wherein the compound conversion process is an intermolecular hydroamination of linear aminoalkenes. 23. Use of the material according to any of claims 1 to 8 as a compound absorbent. 24. Use of the material according to any of claims 1 to 8 as a molecular sieve. 25. Use of the material according to any of claims 1 to 8 as a controlled drug delivery system.