Patent Application
20220169593
Alkyl-aryl amine-rich small molecules (Ph-XX—YY) were prepared by nucleophilic substitution from tri- and hexa-bromine-substituted aromatic cores with various aliphatic diamines. The resulting products were subsequently subjected by solution impregnation into solid mesoporous supports. Various types of Ph-XX—YY molecules filled the support's pores up to ˜90% and displayed good thermal stability.
The present invention discloses a versatile one-pot synthetic method to prepare different types of amine-rich small molecules (Ph-XX—YY) of various compositions. Nucleophilic substitution was employed to react tri- and hexa-bromine-substituted aromatic cores with excess ethylenediamine and propane-1,3-diamine. The excess diamine prevents oligomerization and favored high yields of products. Synthesis of alky-aryl amines was confirmed by 1H, 13C NMR and high-resolution mass spectrometry (HR-MS). Also described composite materials made of various organic loadings of Ph-XX—YY molecules combined with various mesoporous support materials; first with SBA-15 mesoporous silica a prototypical example, through solution impregnation. In addition, porous supports such as alumina, carbon, titania, porous polymers, and MOFs can also be used. The wet impregnation approach yielded composite materials, such as Ph-XX—YY/SBA-15. Thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) were used to investigate the thermal behavior of the pure Ph-XX—YY and composite materials. It was found that encapsulation in the SBA-15 pores shields Ph-XX—YY molecules, slowing their thermal degradation. N2 physisorption analysis was used to assess the porosity of the composite materials and determine the pore structure parameters of the Ph-XX—YY/SBA-15 composites. The specific BET surface area decreased with the increase in Ph-XX—YY loadings, a trend also followed by the total pore volume and average pore size. These results confirmed the presence of Ph-XX—YY within the cylindrical pores of SBA-15. Together the data indicate that, due to their good thermal stability and uniform distribution within mesoporous solid supports, Ph-XX—YY/solid mesoporous support (e.g. silica, γ-Al2O3, porous carbon) composites are appealing platforms for various applications, in particular integration into direct air CO2 capture (DAC) or other CO2 capture technologies as well as H2S capture.
Benzene substituted with various functional groups has been found as an appealing core for the preparation of star-like small molecules and polymers. Sun et.al prepared a series of polymers by facile nucleophilic substitution reactions using inexpensive and readily available 2,4,6-tris(chloromethyl)mesitylene (TCM) and diamine monomers.1, 2 Because of the halogen group's affinity to amines, the reaction was carried out at a mild temperature (60° C.) and did not require any catalyst. Two invention disclosures by Looper et al. have described the methods for preparing a variety of polyamines containing an aromatic core anchored by one, two and three amine-rich side arms.3, 4 In order to achieve the desired biocidal activity, the authors have used a three-step synthesis that, in the case of some products, required protection of one terminal primary amine of spermine and of its polyamine homologues. In addition, the preparation also required the use of metal catalysts (e.g. Pd) and pyrophorics (e.g. NaH).3 In another multi-step approach. Stawicki et al. have reported dipodal and tripodal amine scaffolds that were subsequently used to prepare ligand adducts for in-vivo uranyl removal. In order to prepare these amines, the authors have reacted bis- and tris-bromo-methyl-aryl derivatives with excess diamine (e.g. ethylenediamine, 1,3-propylenediamine, 1,4-butandiamine).5 A relatively similar route was proposed by Guo et al., but, additionally, they have explored 1,3,5-tricarboxyaldehides to synthesize polyamino tripodal ligands.6 The diamines used, N-ethyl-ethylenediamine, N-n-propyl-ethylenediamine and N-n-butyl-ethylenediamine were more complex and richer in primary and secondary amine groups than those reported by Stawicki et al.6-8 The same tricarboxyaldehydes were used by Still et al. in an invention that synthesized a series of polyamine molecules for use as synthetic receptors.9 The composition of amine-containing materials described in these examples was highly complex because their target applications required multifunctionality. Reaction of aromatic dialdehydes and guanidine groups recently reported by Seipp et al. has yielded crystalline, amine-rich molecules for use as adsorbents in CO2 capture.10 In their approach the authors have used an aqueous solution of the synthesized 2,6-pyridine-bis(iminoguanidine) that was allowed to slowly crystallize in ambient air conditions. CO2 and water were adsorbed as a part of a crystal hydrate form that, upon heating at 120° C. were released, according to optical microscopy (crystal color change) and thermogravimetry. Indeed, this is another example of innovative approach but it is rather challenging to achieve good CO2 adsorption/desorption properties. The departure of CO2 from the crystalline phase requires elevated temperature that makes the process costly.
Aromatic carboxylic acids were also investigated for their reactivity toward amines as a potential pathway leading to amine-rich compounds. Nagata et al. have reported aliphatic-aromatic and aromatic polyimines through reaction of trimesic and pyromellitic acids with hexa-, deca-, and dodecamethylenediamine.11 Melt condensation between trimesic acid and diamines (e.g. hexamethylene, dodecamethylenediamine) was employed by Kiyotsukuri et al. to prepare transparent polyamide films that were insoluble in organic solvents.12 Additionally, the authors have used aromatic diamines such as 4,4′-oxydianiline, 1,4-phenylenedimethanamine, benzene-1,4-diamine, benzene-1,3-diamine and piperazine that reacted with trimesic acid afforded aromatic polyamido-amines with high resistance to thermal degradation.13 Similar hyperbranched polyamides derived from trimesic acid were also reported by Jikei et al.14 Edwards and Robinson have disclosed the synthesis of organic salts, namely poly(pyromellitimide)s.15 In order to afford high-molecular-weight salts, the authors converted pyromellitic acid to its aldehyde homologue that was subsequently reacted with 4,4-dimethylheptamethylene diamine, nonamethylene diamine and 3-methylheptamethylene diamine. Recently, pyromellitic dianhydride was used in combination with Jeffamine D-400 by Yu et al. to prepare amine hardeners.16 Investigations performed by Kumar et al. showed that the reaction mechanism between pyromellitic dianhydride and aromatic diamines occurred in two stages.17 First the formation of a prepolymer complex was observed, which in the presence of excess dianhydride led to high molecular weight poly(amic acid).17 While these polyamido-amines presented an increase in resistance to thermal degradation, their synthetic route may be regarded as a difficult to scale up process due to the associated costs, especially for technologies such as DAC.
Other amine-rich molecules used in tandem with solid supports have been explored as adsorbent materials for DAC as well as other mixtures of gases, such as natural gas and flue gases.18 The most used method for preparation of these composite materials is solution impregnation leading to both physical binding of amine molecules to the substrate surface and partial or complete pore filling.19, 20 Depending on their porosity,21 solid supports are able to carry varied amounts of amine content.22 They also prolong the life time use of amine active sorbents because of their improved stability under ambient and thermally treated conditions. In this regard, mesoporous silicas,19, 23-25 alumina,26, 27 zeolites,28 graphene oxide,29 porous polymers,30 carbons,31, 32 MOFs33, 34 and carbon nanotubes35, 36 are a few examples of supports investigated for extending the library of amine-containing composite materials for CO2 capture.
Many aspects of the present disclosure can be better understood with reference to the following drawings. The components in the drawings are not necessarily to scale, with emphasis instead being placed upon clearly illustrating the principles of the disclosure. Moreover, in the drawings, like reference numerals designate corresponding parts throughout the several views.
Synthesis of Ph-3-ED. 1,3,5-tris(bromomethyl)benzene (2 g, 5.6 mmol) was dissolved in dry THF (60 mL) under argon at room temperature. This solution was added dropwise to excess ethylenediamine (13.5 g, 224 mmol) at room temperature under argon. After complete addition, the reaction mixture was stirred overnight at room temperature. The solvent and excess ethylenediamine were removed under reduced pressure (rotary evaporation). Subsequently, the resulting brown viscous oil was dissolved in methanol (15 mL). Potassium hydroxide (0.9 g, 16.8 mmol) was added and the mixture was stirred for 1 hour. The inorganic salt (KBr) was precipitated by addition of diethyl ether and removed by filtration. The filtrate was rotary evaporated to afford a high viscous yellow oil (1.58 g, 96% yield). 1H NMR, (D2O, 700 MHz), δ (ppm): 7.21 (3H, s), 3.73 (6H,s), 2.71 (6H,t), 2.61 (6H,t). 13C NMR, (D2O, 175 MHz), δ (ppm): 139.76, 127.39, 52.14, 50.01, 39.82. m/z: found; [M+H]+ 295.2607, calc. for [M+H]+ 295.2605.
Synthesis of Ph-3-PD: 1,3,5-tris(bromomethyl)benzene(2 g, 5.6 mmol) was dissolved in dry THF (60 mL) under argon at room temperature. This solution was added dropwise to excess propane-1,3-diamine (16.6 g, 224 mmol) at room temperature under argon. After complete addition, the reaction mixture was stirred overnight at room temperature. The solvent and excess propane-1,3-diamine were removed under reduced pressure. Subsequently, the resulting colorless viscous oil was dissolved in methanol (15 mL). Potassium hydroxide (0.95 g, 16.8 mmol) was added and stirred for 1 hour. The inorganic salt (KBr) was precipitated by addition of diethyl ether and removed by filtration. The filtrate was rotary evaporated to afford a highly viscous yellow product (1.8 g, 95% yield). 1H NMR, (D2O, 700 MHz), δ (ppm): 7.20 (3H, s), 3.72 (6H, s), 2.67 (6H, t), 2.58 (6H,t), 1.65 (6H, q). 13C NMR, (D2O, 175 MHz), δ (ppm): 139.56, 127.52, 52.17, 45.38, 38.48, 30.48. m/z: found; [M+H]+ 337.3078, calc. for [M+H]+ 337.3074.
Synthesis of Ph-6-ED: In a round bottom flask 1,2,3,4,5,6-hexakis(bromomethyl)benzene (1.5 g, 2.36 mmol), excess ethylenediamine (8.5 g, 141.5 mmol) and KOH (0.7 g, 14.2 mmol) were added under argon atmosphere. The reaction mixture was stirred overnight at room temperature. Excess diamine was removed under reduced pressure (rotary evaporation). The resulting brown and viscous product was dissolved in methanol (10 mL). The inorganic salt (KBr) was precipitated by addition of diethyl ether and removed by filtration. The filtrate was rotary evaporated to afford a highly viscous brown liquid. The product was dried on a high vacuum line to remove trace amine (0.7 g, 58% yield). 1H NMR, (D2O, 700 MHz), δ (ppm): 3.80 (12H, s), 2.80 (24H, m). 13C NMR (D2O, 175 MHz), δ (ppm): 137.46, 51.76, 47.03, 39.79. m/z: Found; [M+H]+ 511.4663, calc. for [M+H]+ 511.4667.
Synthesis of Ph-6-PD: In a round bottom flask 1,2,3,4,5,6-hexakis(bromomethyl)benzene (1.5 g, 2.36 mmol), excess propane-1,3-diamine (10.5 g, 141.59 mmol) and KOH (0.82 g, 14.63 mmol) were added under argon atmosphere. The reaction mixture was stirred overnight at room temperature. Excess propane-1,3-diamine was removed under reduced pressure (rotary evaporation). Subsequently, the resulting colorless viscous product was dissolved in methanol (10 mL). The inorganic salt (KBr) was precipitated by addition of diethyl ether and separated by filtration. The filtrate was evaporated to afford a highly viscous yellow liquid (1.2 g, 85% yield). 1H NMR, (D2O, 700 MHz), δ (ppm): 3.78 (12H, s), 2.77 (12H, t), 2.67 (12H, t), 1.69 (12H, q). 13CNMR, (D2O, 175 MHz), δ (ppm): 137.42, 47.22, 46.90, 38.76, 31.38. m/z: found; [M+H]+ 595.5602, calc. for [M+H]+ 595.5606.
Pluronic P-123 block copolymer ((EO)20(PO)70(EO)20) (12 g) was dissolved in deionized water (318 mL). HCl solution (60 mL, 21.1 M) was added to the mixture and vigorously stirred for 3 h until a clear solution was formed. Tetraethyl orthosilicate (TEOS, 23.3 g) was dropwise added to the reaction mixture under constant stirring. After TEOS dropwise addition, the temperature was raised to 40° C. and held for 24 h. During this time a white precipitate has formed. Then the stirring was stopped and the temperature was raised to 100° C. for additional 20 h. Afterwards the reaction was quenched with 400 mL deionized water and the precipitate was filtered and washed copiously with deionized water. The filtered precipitate was dried for 12 h in an oven at 75° C. under ambient air conditions. The dried sample was then calcined according to the following temperature program: heat to 200° C. at 1.2° C. min−1, hold at 200° C. for 1 h, heat to 550° C. at 1.2° C. min−1, hold at 550° C. for 12 h, uncontrolled cooling to room temperature. The resulting white powder was stored in a glass jar at ambient conditions.
SBA-15 was loaded with Ph-XX—YY by wet impregnation. Before use SBA-15 was dried overnight under vacuum (<20 mTorr) at 110° C. to remove trace water. Then for each composite formulation SBA-15 (200 mg) and methanol (50 mL) was mixed into a round bottom flask and stirred for 2 h. Separately, the desired amount of Ph-XX—YY was dissolved in methanol 10 mL and stirred for 10-15 min. This solution was added to SBA-15/methanol mixture and stirred overnight at room temperature. The solvent was removed under reduced pressure (rotary evaporation). The resulting powder was dried overnight under vacuum (<20 mTorr) at 50° C. All prepared composite powders were stored in glass vials at ambient conditions.
The preparation of these composites followed the same steps, conditions and amounts of materials as described above for Ph-XX—YY/SBA-15.
1. Composites of Ph-XX—YY and mesoporous silica (SBA-15). Tri and hexa-amine substituted benzene molecules were synthesized by one-step reaction between commercially available analogous bromomethyl-substituted benzene and excess diamines (Table 1). Ph-3-ED was prepared by nucleophilic substitution between excess ethylenediamine and 1,3,5-tris(bromomethyl)benzene (Scheme 1). Dry THF solution of 1,3,5-tris(bromomethyl)benzene was added dropwise to excess ethylenediamine. Excess and slow addition is required to prevent oligomerization/polymerization. The resulting viscous oil was dissolved in KOH/methanol solution. The inorganic salts were precipitated by addition of diethyl ether and removed by filtration to obtain the desired Ph-3-ED in excellent yield (>95%). A similar strategy was employed to synthesize Ph-3-PD. Nucleophilic substitution between excess propane-1,3-diamine and 1,3,5-tris(bromomethyl)benzene gave a transparent viscous liquid in a yield of 96% (Scheme 2). The 1H NMR spectrum of Ph-3-ED showed three protons of the phenylene ring appearing as singlets at 7.21 ppm. The proton signal of the methylene group directly connected to phenyl ring appeared as singlet at 3.73 ppm. A pair of triplets centered at 2.61 and 2.71 ppm was assigned to methylene protons belonging to the alkyl chain of the diamine: one connected to the secondary amine and the other one to the primary amine, respectively. HR-MS of the Ph-3-ED evaluated the m/z ratio as 295.2607 Da (calc. 295.2605). The 1H NMR spectrum of Ph-3-PD showed similar peaks as compared to that of Ph-3-ED except an additional peak observed at 1.65 ppm for the additional methylene protons. HR-MS of the Ph-3-PD gave an m/z ratio of 337.3078 Da (calc. 337.3074).
Hexa-amine substituted benzene molecules were synthesized using a similar method as stated above. Hexakis(bromomethyl)benzene was treated with excess of ethylenediamine or 1,3-diaminopropane to obtain the corresponding Ph-6-ED and Ph-6-PD, respectively. As expected, the 1H NMR spectra of Ph-6-ED and Ph-6-PD did not show any phenyl protons confirming their full substitution with alkyl diamines. Methylene protons directly connected to the phenyl ring were observed at ˜3.8 ppm for Ph-6-ED and Ph-6-PD, as was similarly observed for Ph-3-YY (˜3.72 ppm). For Ph-6-ED, the methylene protons between the primary and secondary amines were observed as multiplets (2.75-2.85 ppm). In contrast, for Ph-6-PD, two triplets were observed centered at 2.67 and 2.77 ppm for the methylene protons directly connected to the primary and secondary amines. HR-MS of the Ph-6-ED showed the molecular ion at 511.4663 Da (m/z) (511.4667 calc.). The 1H NMR spectrum of Ph-6-PD showed similar peaks as compared to the Ph-3-ED, with an additional peak at 1.69 ppm for methylene protons. HR-MS of the Ph-6-PD observed the molecular ion at 595.5602 Da (m/z) (595.5606 calc.).
The SBA-15 support was functionalized with Ph-XX—YY using a wet impregnation method. In a typical synthesis process, the desired amount of Ph-XX—YY was dissolved in methanol (10 mL). In a separate round bottom flask, the SBA-15 support material (200 mg) was added to 50 mL of methanol and stirred vigorously for 1h. Subsequently, the Ph-XX—YY solution was added to the SBA-15/methanol suspension and the final mixture was stirred overnight at room temperature. After that, the solvent was removed using rotary evaporation and dried overnight under high vacuum. The percentage loading of the polymer in the composite was varied by using equation 1.
where α represents the mass of added Ph-XX—YY (g) and β represents the mass of SBA-15 silica support (g).
Thermogravimetric analysis (TGA) was used to evaluate the decomposition profiles of organic and inorganic constituents of the pure and Ph-X—YY/SBA-15 composites. As shown in
Differential scanning calorimetry (DSC) performed in tandem with TGA revealed additional information about the thermal behavior of these composite materials.
The described peaks have changed their positions in the Ph-XX—YY/SBA-15 composites. A sharp endothermic event assigned to alkyl chains gaining mobility within the SBA-15 pores was centered at about 180-225° C. The ‘fluidization’ of aromatic rings event shifted up with ˜20-30 centigrades (550° C.-580° C.). The shift in the position of the two peak ranges is likely associated with desorption of the alkyl branches and aromatic core from the support pore walls. Overall the TG/DSC data indicate that pure Ph-XX—YY and their composites with SBA-15 have a broad decomposition profile accompanied by phase and structural changes. These data suggest that confinement of Ph-XX—YY in the mesoporous support leads to good thermal stability necessary for many practical applications.
N2 physisorption analysis was further used to determine the porosity and pore structure parameters of the support SBA-15 before and after impregnation with Ph-XX—YY molecules. As shown in
For example, as shown in Table 2, the total pore volume of 20% Ph-3 -ED/SBA-15 composite decreased from 0.96 cm3/g to 0.71 cm 3/g (26% pore filling). The reduction in the total pore volume and pore size of the SBA-15 was correlated to the increase in organic loadings. An increase of 30, 40 and 50% in organic content was reflected in a further decrease in pore volume 0.59 cm3/g, 0.41 cm3/g and 0.18 cm3/g, respectively. These values correspond to a pore filling percentage of 39, 57 and 82% respectively. The same trend was assessed by amine loadings obtained by elemental analysis (EA). The amine loadings in the samples increased from 3.3 mmole N/g at 20% loading to 11 mmole N/gSiO2 at 50% loading, coinciding with the increasing Ph-3-ED samples loading in the pores of SBA-15 (Table 2). Similar trends were observed for the other composite samples (Table 2). The calculated pore filling values for 20, 30, 40 and 50% organic loading were 20%, 40% 61% and 90% for Ph-3-PD/SBA-15, 34%, 55%, 77% and 94% for Ph-6-ED/SBA-15 and 39%, 49%, 69% and 92% for Ph-6-PD/SBA-15. The amine loadings in Ph-3-PD/SBA-15 composite increased from 3.94 to 12.45 mmol N/gSiO2 for organic loadings between 20-50%. As expected in case of Ph-6-ED and Ph-6-PD, a higher amine loading range was observed 4.54-16.7 mmol N/gSiO2 and 4.23-15.45 mmol N/gSiO2, respectively. Additionally,
Another important parameter that confirmed successful impregnation of Ph-XX—YY into the SBA-15 supports was the specific surface area. As listed in Table 2, the BET surface area of bare SBA-15 was 700 m2/gSiO2. In general, variation of this parameter for the composite samples was in the 400-30 m2/gSiO2 range following the trend in pore filling. As expected, the slightly smaller specific surface area and slightly higher total pore filling of Ph-6-YY, as compared to the Ph-3-YY, is due to the fact that Ph-6-YY molecules are bulkier and occupy a larger volume.
ED/SBA-15 and (d) Ph-6-PD/SBA15 composites. Each graph contains the trace of neat SBA15.
The DSC traces recorded in conjunction with TGA (
N2 physisorption measurements were further performed to determine the pore characteristics of the two substrates and their composite materials, as shown in
Three and six alkyl diamine-substituted aryl cores (Ph-XX—YY) were prepared by nucleophilic substitution from the corresponding tri and hexa bromomethyl substituted benzene with excess ethylenediamine and 1,3-diaminopropane. The one-pot synthesis of these amine-rich molecules was confirmed by 1H, 13C NMR and high resolution mass spectroscopy (HR-MS). All products were obtained in high yields. Subsequently, these molecules were loaded by solution impregnation into mesoporous solid substrates (SBA-15, mesoporous carbon and γ-Al2O3) at various concentrations. The organic loading of the composite materials was confirmed by TGA and elemental analysis and was comparable to the theoretical value. Both DSC and TGA analyses performed on these mixtures revealed good thermal stability spanning from 180° C. to 560° C.
The porosity and pore structure of the Ph-XX—YY/solid substrate composites were assessed by N2 physisorption measurements. The presence of the Ph-XX—YY molecules in the support pores was confirmed by a decrease in both the average pore size and surface area of the composite materials. The highest pore filling achieved for 50% organic loading was 94% for Ph-6-ED/SBA-15. This value was slightly higher when compared to Ph-3-ED/SBA-15, Ph-3-ED/mesoporous carbon and Ph-3-ED/γ-Al2O3 homologues. Different values were also evaluated for SBA-15-based composites containing Ph-3-ED vs. those containing Ph-3-PD. These data indicated that the molecular structure of the Ph-XX—YY was tightly associated with the pore characteristics of the composites. Importantly, results obtained from TGA and N2 physisorption measurements showed that no Ph-XX—YY loss occurred during the preparation of the adsorbent and suggested that almost all Ph-XX—YY was introduced into the pores.
The ability to prepare thermally stable alky-aryl amine rich small molecules by a scalable one-pot approach offers great potential in using them in multiple applications. They are appealing candidates for integration as adsorbents in gas separation, direct air CO2 capture and H2S capture technologies.
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Alkyl-aryl amine-rich small molecules (Ph-XX—YY) were prepared by nucleophilic substitution from tri- and hexa-bromine-substituted aromatic cores with various aliphatic diamines. The resulting products were subsequently introduced by solution impregnation into solid mesoporous supports. Various types of Ph-XX—YY molecules filled the support's pores up to ˜90% and displayed good thermal stability.
Amine molecules or polymers supported on/in solid supports are known materials with diverse applications. Here we synthesize a family of amine molecules based on a phenyl core with alkyl amine branches and incorporate these materials on/in solid supports. While some related amine molecules with an aromatic core are known (see prior art), many molecules reported here are new. While solid-supported forms of other amine molecules and polymers are known, these compositions are new, with no reports of supported versions of these amine molecules known. The alky-aryl amine rich small molecules are thermally stable. They are made in the one-step process, with mild reaction conditions and chemicals that do not prose safety concerns. Impregnation of these molecules into mesoporous substrates provides them higher thermal stability when compared to linear alkyl amines.
The present invention discloses the preparation of amine-rich small molecules (Ph-XX—YY) of various compositions. Nucleophilic substitution was employed to react tri- and hexa-bromine-substituted aromatic cores with excess ethylenediamine and propane-1,3-diamine. The excess diamine prevents oligomerization and favored high yields of products. Synthesis of alky-aryl amines was confirmed by 1H, 13C NMR and high-resolution mass spectrometry (HR-MS). Also escribed composite materials made of various organic loadings of Ph-XX—YY molecules combined with various mesoporous support materials; first with SBA-15 mesoporous silica a prototypical example, through solution impregnation. In addition, porous supports such as alumina, carbon, titania, porous polymers, and MOFs can also be used. The wet impregnation approach yielded composite materials, such as Ph-XX—YY/SBA-15. Thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) were used to investigate the thermal behavior of the pure Ph-XX—YY and composite materials. It was found that encapsulation in the SBA-15 pores shields Ph-XX—YY molecules, slowing their thermal degradation. N2 physisorption analysis was used to assess the porosity of the composite materials and determine the pore structure parameters of the Ph-XX—YY/SBA-15 composites. The specific Bet surface area decreased with the increase in Ph-XX—YY loadings, a trend also followed by the total pore volume and average pore size. These results confirmed the presence of Ph-XX—YY within the cylindrical pores of SBA-15. Together the data indicate that, due to their good thermal stability and uniform distribution within mesoporous solid supports, Ph-XX—YY/solid mesoporous support (e.g., silica, y-A1203, porous carbon) composites are appealing platforms for various applications, in particular integration into direct air CO2 capture (DAC) or other CO2 capture technologies as well as H2S capture.
What are the commercial applications for the invention?
The capture of acid gasses from gas mixtures, including (CO2, SO2, NO, NO2, H2S, etc.). While Global Thermostat has an interest primarily in CO2, we have also shown the materials to be effective for H2S capture, which could open the field of licensees substantially. A separate IP will be filed on H2S capture application with different inventors.
What are the advantages of the invention over present technologies?
The alkyl-aryl small molecules contain a high amount of amine groups and due to the aryl core, have better thermal stability than regular linear alkyl amines. Impregnation of these molecules into mesoporous substrates further increases their thermal stability.
This application claims priority to, and the benefit of the contents of U.S. provisional application entitled “Alkyl-Aryl Amine-Rich Small Molecules and Their Composites with Solid Mesoporous Substrates” having Ser. No. 63/034,001 filed on Jun. 3, 2020, which is entirely incorporated herein by reference.
| Number | Date | Country | |
|---|---|---|---|
| 63034001 | Jun 2020 | US |
