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. 2026 Jan 7;11(2):2546–2553. doi: 10.1021/acsomega.5c06595

Amine-Functionalized Porous Carbon for Efficient Adsorption of Propylene Oxide

Siyu Kuang 1,*
PMCID: PMC12824964  PMID: 41585633

Abstract

As an important organic chemical raw material, propylene oxide (PO) has a large demand for its production. However, due to its low boiling point (34 °C), the subsequent transportation, loading, and unloading process also faces the risk of leakage of a large amount of volatile gases of propylene oxide, which will have a negative impact on the environment. Therefore, the design of efficient propylene oxide adsorbents has an important impact on the chemical production and transportation process and the environment. This study examined how the pore size of porous carbon affects propylene oxide adsorption using molecular simulation. The results identified the micropore range as optimal for adsorption. Comparative analysis of the impacts of the pore size distribution on the adsorption performance of propylene oxide revealed consistent results between experimental and theoretical calculations. To further enhance the PO uptake performance, amine-functionalized porous carbon was synthesized. Compared to unmodified porous carbon (C0, PO uptake capacity: 3.78 mL/g), the amine-modified porous carbon (C1) exhibited a significant improvement in PO uptake, reaching 12.5 mL/g. The results of Fourier transform infrared spectroscopy show that the primary amine group on porous carbon reacts with propylene oxide via a ring-opening addition reaction during the adsorption process, resulting in better PO uptake performance of amine-functionalized porous carbon than pristine porous carbon. The regeneration performance of the amine-functionalized porous carbon material was also evaluated and proved to be excellent. These experimental and theoretical findings provide new ideas for further designing and developing adsorbents with enhanced uptake performance for propylene oxide.

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1. Introduction

Propylene oxide (PO) is a very important organic compound raw material and is the third largest propylene derivative after polypropylene and acrylonitrile. , Its chemical properties are as follows: active, ease of ring-opening polymerization, can react with water, ammonia, alcohol, carbon dioxide, etc., to generate the corresponding compounds or polymers, can be used as cellulose ester and resin solvent and in the production of surfactants, plasticizers, stabilizers, and other main raw materials, and widely used in chemical, pesticide, automobile, construction, daily chemical, and other industries. With the improvement of real estate construction and the increase in the permeability of automobiles, polyurethane coatings, and other industries to drive the growth of the industry, it is expected that the demand for propylene oxide will continue to maintain rapid growth. At present, in the production process of the downstream products using propylene oxide as the raw material, the conversion rate of propylene oxide cannot reach 100%, and the unconverted propylene oxide is discharged into the atmospheric environment as one of the pollution sources. , Due to the low boiling point of propylene oxide (34 °C), the subsequent transportation and handling process is also faced with the risk of leakage of a large amount of propylene oxide volatile gas, which will also have a negative impact on the environment. Therefore, the effective adsorption of propylene oxide volatile gas has an important impact on the chemical production and transportation process and the environment. Among current environmental treatment strategies, adsorption technology offers a combination of exceptional efficiency and low energy demand. Therefore, developing high-performance solid porous adsorbents is crucial. ,

Porous carbon materials present a compelling advantage over other adsorbents, such as zeolite molecular sieves, − covalent organic frameworks (COFs), − and metal–organic frameworks (MOFs). − Despite the adsorption capabilities of the latter, porous carbons outperform them by combining lower preparation costs, high stability, and good recyclability. , However, due to the weak adsorption of adsorbents and propylene oxide, the removal effect of commonly used adsorbents (such as activated carbon, molecular sieves, silica gel, etc.) is not satisfactory. Therefore, it is particularly important to develop new adsorbents for the specific adsorption of propylene oxide.

In recent years, researchers have improved the adsorption properties of carbon materials by adjusting the pore size and modifying functional groups on the surfaces. According to Liu et al., adsorption and separation performance on carbon materials is primarily governed by van der Waals interactions. These forces are most effective within an optimal pore size range, and a sharp decline in adsorption occurs outside this range due to weakened interactions. By modifying functional groups on the surface of activated carbon, the affinity between the adsorbent and modified activated carbon surface functional groups can be improved, thus effectively improving the adsorption selectivity of organic compounds. − Therefore, according to the physical and chemical properties of propylene oxide, the design of a porous carbon adsorbent with optimal pore size and specific functional group modification is expected to achieve efficient removal of propylene oxide.

Herein, we employed molecular simulations to calculate the adsorption performance of propylene oxide in slit-pore models with different pore sizes. To validate the results obtained from theoretical calculations, we evaluated several porous carbons with different pore size distributions and revealed that the micropore plays a key role in adsorption of propylene oxide. Based on the active chemical properties of propylene oxide, the amine-functionalized porous carbon was designed and synthesized, and the propylene oxide was efficiently removed by nucleophilic addition reaction between the primary amine and the epoxy group, which was further confirmed by FT-IR. Finally, the regeneration performance of the amine-functionalized porous carbon material was evaluated and proved to be excellent. This study provides valuable guidance for the design and development of adsorbents for propylene oxide.

2. Experimental Section

2.1. Simulation Models and Methods

Molecular simulations were performed to evaluate the adsorption behavior of propylene oxide in carbon models featuring different pore sizes. In these simulations, the porous structures were simplified as a series of slit-pore models with graphite walls (Figure S1). , Geometric optimization of both the adsorbate molecules and the graphite sheets was conducted using the Forcite module. , Propylene oxide adsorption at 25 °C was simulated within the SORPTION package employing the COMPASS force field. Van der Waals interactions were treated with an atom-based method, while electrostatic interactions were computed using the Ewald and Group summation method. To ensure that the system reached equilibrium, each simulation included 2 × 107 equilibrium steps and 2 × 107 production steps. ,

2.2. Materials

The porous carbons with different pore distributions were purchased from Calgon Carbon Corporation (c-C1) and TIANNENG Carbon Ltd., China (c-C2 and c-C3). Tris­(hydroxymethyl)­aminomethane (99.8%) was purchased from Macklin. Dopamine hydrochloride (98%) was purchased from Aladdin. Diethylenetriamine, sulfuric acid (H2SO4, 98%), and acetone (99.5%) were purchased from Sinopharm Chemical Reagent Co., Ltd. Standard gas with 0.04 vol% propylene oxide and 99.96 vol% nitrogen was purchased from YUANZHENG Gas Ltd., China. No further purification of the chemicals or gases was conducted prior to use.

2.3. Synthesis of Amine-Functionalized Porous Carbons

The porous carbon c-C1 was soaked in sulfuric acid for 48 h and then cleaned with deionized water several times. Then, the cleaned porous carbon was placed in a vacuum drying oven for 12 h to obtain the dehydrated porous carbon C0.

For the preparation of Tris buffer: 0.12 g of tris­(hydroxymethyl)­aminomethane was placed in a 100 mL volumetric bottle, dissolved with an appropriate amount of deionized water, and then dropped with sulfuric acid to adjust the pH to about 8.5. Then, 0.1 g of dopamine hydrochloride and 0.1 g of diethylenetriamine were fully dissolved in the buffer solution prepared, 8 g of porous carbon C0 after acetone treatment was immersed in the two-component solution of dopamine and diethylenetriamine, and the reaction was carried out at room temperature for 24 h. After the reaction was complete, the porous carbon was cleaned several times with deionized water through filtering and then dried overnight in the oven to obtain the amine-functionalized porous carbon C1. The preparation steps of the amine-functionalized porous carbons C0-5, C1-5, and C2 are consistent with the above steps except that the addition amounts of amine (dopamine and diethylenetriamine) are 0.05, 0.25, and 0.5 g, respectively.

2.4. Characterization

The morphologies of the samples were characterized by scanning electron microscopy (SEM, Thermo Scientific Apreo 2). X-ray photoelectron spectroscopy was used to determine the surface elemental composition of the samples (XPS, ESCALab250 Thermo Fisher electron spectrometer). FT-IR spectroscopy was performed on a Thermo Fisher Nicolet IS50 spectrometer. Thermogravimetric analysis (PerkinElmer TGA Pyris 1) was carried out from 25 to 800 °C with a heating rate of 10 °C min–1 in a flow of N2. N2 adsorption–desorption isotherms were obtained at 77 K using a specific surface area and vapor adsorption analyzer (BeiShiDe Instrument Technology (Beijing), Ltd.). The Brunauer–Emmett–Teller (BET) model was applied to determine the specific surface area, and the pore size distribution was analyzed by nonlocal density functional theory (NLDFT).

Dynamic adsorption experiments for propylene oxide (0.04 vol%) balanced with N2 were performed on the samples employing a single-component adsorption breakthrough curve analyzer (BeiShiDe Instrument Technology (Beijing), Ltd.). A gas mixture was fed into the adsorption column at a flow rate of 70 mL/min. All breakthrough tests were carried out at 25 °C and atmospheric pressure with the effluent concentration being monitored by mass spectrometry (BeiShiDe Instrument Technology (Beijing), Ltd.). The PO desorption experiments were performed after the adsorbent bed reached saturation in the breakthrough experiment, and the inlet stream was switched from the PO/N2 mixture to pure nitrogen (70 mL/min) at 80 °C. The effluent gas from the column during purging was periodically sampled (every 2 min) and analyzed by gas chromatography (GC), and the entire effluent gas stream was directed into a pre-evacuated gas sampling bag over the entire purging period. The purging process continued until the GC signal for PO diminished to the baseline level.

In situ infrared (IR) spectra were collected on a Thermo Scientific Nicolet iS50 spectrometer equipped with an MCT detector. Typically, about 15 mg of the diluted sample was pressed into a self-support wafer with a diameter of 13 mm and located in an in situ IR cell (Xiamen Tuozheng Instrument Development Co., Ltd.). Both sides of the in situ cell were sealed with ZnSe windows. The sample was purged with Ar for 30 min to remove the adsorbed species. The background was recorded at 25 °C. Subsequently, the sample was exposed to propylene oxide for 30 min under atmospheric pressure, and the spectra were collected continuously in the range of 4000–1000 cm–1 by averaging 32 scans at a resolution of 4 cm–1.

3. Results and Discussion

3.1. Propylene Oxide Adsorption by Molecular Simulation

Single-component adsorption simulations employing the Metropolis method were conducted to investigate the uptake of propylene oxide gas across varying pore sizes (1.0–4.0 nm), which were selected based on the kinetic diameter of the adsorbate. As depicted in Figure a, the adsorption density at 101.325 kPa first increases rapidly and then declines sharply with an expanding pore size. Notably, high uptake capacity is confined to the micropore range of 1.0–2.0 nm. This is consistent with the variation trend of the isothermal adsorption curves of propylene oxide at 25 °C for different pore sizes (Figure S2).

1.

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(a) Adsorption performance curves of propylene oxide in different pore sizes and (b) microscopic adsorption morphologies visualized of propylene oxide with different pore sizes at 101.325 kPa and 25 °C.

The optimal pore size for adsorbing light hydrocarbons is primarily determined by the van der Waals forces between the pore walls and the molecules. As illustrated in Figure b, the formation of dense adsorption layers and maximum pore volume utilization occur exclusively within the 1.0–2.0 nm range. Although a dense adsorption layer persists at the pore wall owing to the molecule’s high relative mass, the total quantity adsorbed diminishes with increasing pore size. Consequently, the optimum adsorption for propylene oxide is confined to the 1.0–2.0 nm micropore range.

Therefore, three kinds of porous carbon materials (c-C1, c-C2, and c-C3) with different pore structures were first screened. N2 adsorption analysis further characterized the porosity of the porous carbon materials. As shown in Figure a, the isotherms of c-C1 and c-C2 conform to type I (IUPAC classification), revealing their microporous nature. In contrast, the isotherm of c-C3 exhibits a type IV character, suggesting the development of abundant mesopores. The pore size distribution (PSD) of the porous carbon materials is shown in Figure b, which is obtained based on the NLDFT model. As shown in Table S1, c-C1 has the highest specific surface area (1239 m2/g) and a higher proportion of micropores (54.7%). Although c-C2 has a higher percentage of micropore volume (84.9%), its specific surface area is lower (748 m2/g). While, c-C3 has a higher mesoporous volume ratio (64.7%).

2.

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(a) N2 adsorption–desorption curves measured at 77 K. (b) Pore size distribution of c-C1, c-C2, and c-C3. (c) Dynamic breakthrough curves of propylene oxide (0.04 vol%) balanced with N2 at 25 °C of c-C1, c-C2, and c-C3.

The dynamic breakthrough experiments of the porous carbon materials (c-C1, c-C2, and c-C3) were performed in a single-component adsorption breakthrough curve analyzer for propylene oxide gases at 25 °C with nitrogen as the inert carrier gas. Figure c shows the relevant curves obtained by mass spectrometry. The dynamic adsorption capability of the porous carbon materials is quantified by the breakthrough time (C/C 0 = 5%). Comprehensive dynamic breakthrough data are summarized in Table S2. For propylene oxide, the order of the breakthrough time for the porous carbon materials is c-C1 > c-C2 > c-C3. It shows that these porous carbon materials have different affinities for propylene oxide. At the same time, c-C1 has a longer breakthrough time than c-C3, although the two samples have similar specific surface areas, the difference being that c-C1 has more micropores. Notably, c-C1 exhibits the longest breakthrough time and dynamic adsorption amount (3.8 mL/g) for propylene oxide. The dynamic saturation adsorption capacity is governed by the optimal pore size for propylene oxide capture, which lies within the micropore range of 1.0–2.0 nm, thereby confirming the critical role of pore size on adsorption performance.

In order to evaluate the adsorption performance of propylene oxide gases on the porous carbon materials (c-C1, c-C2, and c-C3), single-component adsorption tests were performed at 25 °C and 1.0 bar pressure. The adsorption isotherms are shown in Figure S3. It is noteworthy that the adsorption amounts of propylene oxide exhibit c-C1 > c-C2 > c-C3. This is because c-C1 has more micropores, which is consistent with the results of dynamic breakthrough experiments.

3.2. Characterization of Amine-Functionalized Porous Carbon

To further improve the uptake performance of propylene oxide, amine-functionalized porous carbon is designed to serve as an adsorbent because of the active amine functional group on its surface, which can effectively capture propylene oxide via click chemistry reaction. An amine grafting method is adopted to prepare the amine-functionalized porous carbons (named C0-5, C1, C1-5, and C2).

The morphological analysis of the samples was observed by SEM. As shown in Figure a–c and Figure S4, all samples show a blocky structure. Compared with the amine-modified porous carbon, the surface of C0 without amine modification is smooth. With the increase in the amount of amine grafted on the porous carbon surface, the surface becomes rough gradually. The N element is uniformly distributed on the porous carbon in C0-5, C1, C1-5, and C2 (Figure b,c and Figure S4), demonstrating that amines have been grafted on the carbon surface. X-ray photoelectron spectroscopy (XPS) and Fourier transform infrared (FT-IR) spectroscopy further confirmed the functionalization of amine on the porous carbon surface. The XPS spectra of C0-5, C1, C1-5, and C2 revealed an obvious peak of nitrogen at ∼400 eV (Figure S5), whereas C0 showed trace signal of N species. It can be seen from Table S3 that the N content of C0-5 is 1.94%, C1 is 4.09%, C1-5 is 6.69%, and 9.27% for C2. The C 1s peaks in high-resolution spectra located at ca. 285.6 and 287.9 eV (Figure d) are attributed to C–N and OC–N species of C1 and C2. , Compared with pristine C0 in FT-IR spectroscopy, C1 and C2 displayed characteristic bands of N–H stretching vibrations at 3300–3500 cm–1, C–N stretching vibration at 1130 cm–1, and CO stretching vibration at 1690 cm–1. , The CO stretching vibration may be attributed to the quinone structure on the polydopamine. As shown in TG curves of C0, C1, and C2 (Figure S6), the porous carbon C0 loses only a small amount of weight over the temperature range due to the absence of attachments. After amine modification (C1 and C2), the weight decreased to a certain extent, indicating that the amine successfully grafted to the porous carbon surface and was decomposed by heat after the temperature increase. With increasing the amine amount of the carbon surface, the weight loss rate increased. The results indicated that amines are successfully grafted to the porous carbon surface.

3.

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SEM and EDS mapping images of (a) C0, (b) C1, and (c) C2. (d) C 1s spectra and (e) FT-IR spectra of C0, C1, and C2.

N2 adsorption measurements were conducted to calculate the specific surface area and pore characteristics of the amine-functionalized porous carbon. As shown in Figure S7, the obtained isotherms exhibited type I behavior for C0, C1, and C2, indicating a pronounced presence of microporosity at low pressures (P/P 0 < 0.01). , The pore size distribution (PSD) of the porous carbon materials is shown in Figure S8, which is obtained based on the NLDFT model. ,, As shown in Table S4, the C0 and C1 have the similar specific surface areas (1239 and 1070 m2/g) and micropore volumes (0.51 and 0.47 cm3/g), which means that moderate amine grafting has little effect on the specific surface area and micropore volume of the porous carbon. However, a higher amine content (C2) leads to a decrease in the specific surface area (768 m2/g) and micropore volume (0.37 cm3/g) on the porous carbon surface.

3.3. Adsorption Performance Evaluation

The dynamic breakthrough experiments of the pristine porous carbon (C0) and amine-functionalized porous carbons (C0-5, C1, C1-5, and C2) in a single-component adsorption breakthrough curve analyzer were performed for propylene oxide gases at 25 °C with nitrogen as the inert carrier gas. Figure a,b shows the relevant curves obtained through mass spectrometry. Comprehensive dynamic breakthrough data are summarized in Table S5. For propylene oxide, the order of breakthrough time for the samples is C1 > C0-5 > C1-5 > C2 > C0, which indicated that the amine-functionalized porous carbon has better uptake performance of propylene oxide when compared with the pristine C0. It is worth noting that the C1 with a moderate amount of amine grafting has the longest breakthrough time and the highest PO uptake capacity (12.5 mL/g). With the further increase in the amount of amine grafting, the breakthrough time of C1-5 and C2 is shortened, and the PO uptake capacity begins to decline (10.5 and 9.7 mL/g, respectively), which may be due to excessive amine grafting blocking the micropore channels on the surface of porous carbon (Table S4) and decreased PO uptake capacity. Therefore, a moderate amount of amine grafting and number of micropores are conducive to the uptake of PO.

4.

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(a) Dynamic breakthrough curves of propylene oxide at 25 °C of C0, C0-5, C1, C1-5, and C2. (b) PO uptake capacity of C0, C0-5, C1, C1-5, and C2 at the dry point. (c) N 1s spectra of C1 before and after PO adsorption. (d) Characterization of the evolution of species on the surface during the treatment with PO, as shown by in situ IR spectra of C1.

Compared with pristine C1 in FT-IR spectroscopy (Figure S9), C1 after the adsorption of propylene oxide (red) showed a stretching vibration at 1598 cm–1 attributed to the secondary amine, which proved that the primary amine group on the surface of C1 reacted with PO to form a secondary amine group via a ring-opening addition reaction. This chemical reaction is the dominant mechanism for PO capture, accounting for approximately 71% (9.39 out of 13.26 mL/g) of the total uptake, as confirmed by a subsequent N2 purge desorption experiment (Table S6). This irreversible chemical fixation, coupled with physisorption in the pores, significantly enhances the material’s overall PO removal performance and delays the breakthrough time. The N 1s spectra of C1 after propylene oxide adsorption (Figure c) reveal the emergence of a new peak at 399.8 eV, which is characteristic of secondary amines (C2–N–H), along with a concomitant decrease in the intensity of the primary amine peak located at 398.0 eV (C–N–H2). These observations suggest that the primary amine groups on the surface of C1 participate in a ring-opening addition reaction with propylene oxide, leading to the formation of secondary amines, which is consistent with the FT-IR results.

Moreover, to dynamically monitor the reaction process, we performed in situ DRIFTS studies of the PO uptake process on the functionalized carbon (Figure d). The results show that the bands at 1598 and 1210 cm–1, assigned to N–H bending and C–N stretching of secondary amines, respectively, increase in intensity within the first 15 min of PO treatment, confirming the generation of secondary amines (C2–N–H). Notably, after 15 min, the intensity of these bands begins to decrease, accompanied by the appearance of the C–N peak at 1310 cm–1 corresponding to the tertiary amine (C3–N). We propose that this is because the initially formed secondary amines can further react with PO, leading to the formation of tertiary amines (Figure S10). This observation provides additional mechanistic insight into the reaction pathway. Moreover, as shown in TG curves of pristine C1 (blue) and C1 after the adsorption of propylene oxide (red) (Figure S11), the weight loss rate increased after adsorption, which indicated that the primary amine group on porous carbon reacts with propylene oxide via ring-opening addition reaction, resulting in an increase in its weight loss rate, further confirming the above analysis.

For practical use, regeneration performance is a key parameter to measure the performance of an adsorbent. Therefore, C1 after propylene oxide adsorption was then calcined and modified by amine functionalization to obtain revived C1. As shown in Figure a,b, the revived C1 shows a blocky structure and with the N element distributed uniformly on the porous surface. N2 adsorption measurements were conducted to calculate the specific surface area and pore characteristics of revived C1. As shown in Figure c, the obtained isotherms exhibited type I behavior for revived C1, indicating a pronounced presence of microporosity at low pressures (P/P 0 < 0.01), indicating that the revived C1 still has a similar pore distribution to the pristine C1. However, the specific surface area of revived C1 decreased slightly due to the collapse of micropore walls during the process of calcination (Table S7). To further investigate the PO uptake performance of revived C1, the dynamic breakthrough experiments were conducted (Figure d). The breakthrough time of revived C1 (3150.4 s) is close to that of pristine C1 (3255.8 s), indicating that the amine-functionalized porous carbon has excellent regeneration properties.

5.

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(a) SEM and (b) EDS mapping images of revived C1. (c) N2 adsorption–desorption curves of revived C1. (d) Dynamic breakthrough curves of propylene oxide at 25 °C of pristine C1 (orange) and revived C1 (dark red).

4. Conclusions

In summary, the pore size of porous carbon materials was investigated by using molecular simulations to analyze the adsorption performance of propylene oxide. The results demonstrated that the micropore structure plays a crucial role in the adsorption capacity of propylene oxide. To validate the theoretical calculations, we evaluated three types of porous carbon materials with different pore size distributions. Comparative analysis of the impacts of pore size distribution on the adsorption performance of propylene oxide revealed consistent results between experimental and theoretical calculations. In order to further improve the PO uptake performance of porous carbon, amine-functionalized porous carbon with various amounts of amine grafting was synthesized and evaluated. The results of FT-IR show that the primary amine group on porous carbon reacts with propylene oxide via ring-opening addition reaction during the adsorption process, resulting in better PO uptake performance of amine-functionalized porous carbon than pristine porous carbon. Excess amine grafting obstructs pores and thus diminishes the propylene oxide uptake. Conversely, a moderate grafting density alongside a well-developed microporous structure is essential for enhancing the uptake. Finally, the regeneration performance of the amine-functionalized porous carbon material was evaluated and proved to be excellent. These experimental and theoretical findings provide a foundation for further designing and developing adsorbents with an enhanced uptake performance for propylene oxide.

Supplementary Material

ao5c06595_si_001.pdf (482.4KB, pdf)

Acknowledgments

This work was supported by the SINOPEC science and technology project (324012).

The data that support the findings of this study are available on request from the corresponding author. The data are not publicly available due to privacy or ethical restrictions.

The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsomega.5c06595.

  • Specific surface area, pore distribution, propylene oxide breakthrough data, elemental composition, quantitative results from desorbed propylene oxide experiments, adsorption isotherms, simulation model details, SEM images and EDS mappings, XPS spectra, TG curves, N2 adsorption–desorption curves, and FT-IR spectra of the amine-functionalized porous carbons with varying amine amounts (PDF)

The author declares no competing financial interest.

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

ao5c06595_si_001.pdf (482.4KB, pdf)

Data Availability Statement

The data that support the findings of this study are available on request from the corresponding author. The data are not publicly available due to privacy or ethical restrictions.

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