Metal–Organic Frameworks for Removal of Chemical Warfare Agents: History
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Contributor:
Madeleine C. Oliver
,
Liangliang Huang

The destruction of chemical warfare agents (CWAs) is a crucial area of research due to the ongoing evolution of toxic chemicals. Metal–organic frameworks (MOFs), a class of porous crystalline solids, have emerged as promising materials for this purpose. Their remarkable porosity and large surface areas enable superior adsorption, reactivity, and catalytic abilities, making them ideal for capturing and decomposing target species. Moreover, the tunable networks of MOFs allow customization of their chemical functionalities, making them practicable in personal protective equipment and adjustable to dynamic environments.

  • metal-organic framework
  • Zr-MOFs
  • chemical warfare agent
  • degradation
  • hydrolysis
  • oxidation
  • reaction mechanism

1. Introduction

Chemical warfare agents (CWAs) are lethal weapons of mass destruction that have been utilized in military conflict since their introduction in World War I. The first ever recorded large-scale chemical attack was the release of chlorine gas by German troops against the Allies in 1915, which resulted in more than a thousand casualties [1][2]. Once this proof of their extreme toxicity and devastating effects came to light, continuous efforts were made to investigate and store various toxic compounds for use as fatal devices against soldiers and civilians [1][3]. The most significant use is dated to the Iraq–Iran War, where a massive chemical attack on the city of Halabja resulted in 200 fatalities in 1988 [4]. While the production and use of CWAs were prohibited by the Chemical Weapons Convention shortly after, in 1993 [2], their evolution remains ongoing, and military personnel face growing uncertainty in complex battlefield environments. Terrorist organizations have also increased the relevancy of chemical warfare agents used against civilians, the most notable incidents being fatal nerve agent attacks in the city of Matsumoto and a Tokyo subway system in the late 1990s. Advancements in personal protective equipment that incorporate highly efficient filtration media for the rapid capture and decomposition of CWAs are urgently needed to mitigate the extreme threat these chemical weapons pose to individuals and military operations.
Measures to protect against CWAs must occur before the chemicals reach their biological targets, as the time frame to apply effective treatment after exposure can be as short as minutes [3]. Current protective technologies have been developed using solid materials such as activated carbons, which can collect and retain CWAs released into the atmosphere but cannot decompose them [5]. Metal oxides, mesoporous silica, zeolites, and surfactants have also been investigated [6][7]; however, complications including low adsorption capacities, competition with atmospheric constituents, deactivation of active sites, and slow reaction kinetics render these materials generally incapable of adequate chemical decomposition [7][8][9]. Research efforts have thus shifted to the design of adsorbents, particularly nanoporous materials, with the ability to both capture and efficiently degrade CWAs under operationally relevant field conditions [10]. Metal–organic frameworks (MOFs) are a class of porous crystalline solids that have sparked interest in this area. MOFs consist of metal ion clusters connected by multidirectional carbon-based bridging linkers, yielding pores with sites for both organic and inorganic chemistry [11]. With tunable networks that provide customizable chemical functionalities, MOFs are adjustable to dynamic environments, making them useful in a wide variety of practical applications, such as gas storage, separations, drug delivery, chemical sensing, and catalysis [11][12][13]. In recent years, MOFs have been identified as superior materials for detecting and breaking down target species, owing to their excellent adsorption, reactivity, and catalytic abilities [1]. Coupled with their exceptional porosities and large surface areas, many MOFs provide an ideal setting for the selective capture and detoxification of CWAs [1][8][9][11][14][15][16][17].

2. Properties of Chemical Warfare Agents

2.1. Nerve Agents, Vesicants, and Their Simulants

CWAs can be divided into several types, including nerve agents, blister agents (vesicants), blood agents, tear agents, and choking agents. The most common are nerve agents and vesicants, which can be further split into categories based on their chemical structures. Nerve agents belong to the chemical group of organophosphorus compounds. They can be either G-type or V-type, where G-type indicates fluorine (GB, GD, GF)- or cyanide (GA)-containing compounds, and V-type (VX) indicates sulfur-containing compounds [18]. G-type nerve agents, such as sarin (GB) and soman (GD), are among the most toxic of CWAs, causing inhibition of proper muscle responses in the body within seconds of exposure and death within minutes [18][19]. Blister agents are less threatening than nerve agents, primarily intended to injure rather than kill people [18]. There are three categories of blister agents, including mustards (HD, HN-1, HN-2, HN-3), arsenicals (L, HL, PD), and urticants (CX). Mustards are the most prominent members of the vesicant family [20], existing in the form of nitrogen mustard (HN) or sulfur mustard (HD). Damage from these CWAs usually occurs in the tissues, in the form of blisters on the skin or irritation of the eyes [21]. Still, like nerve agents, vesicants are typically disseminated as vapors or liquids and can be inhaled and readily absorbed through the skin. While nerve agents range in persistency, all vesicants are relatively persistent, making fatality a possibility depending on exposure conditions (especially in the case of repeated exposures).
The literature reviewed in this work is primarily concentrated on the degradation of the nerve agents GB, GD, and VX and the blister agent HD. Due to their high toxicity, experimental research using CWAs can be hazardous and is restricted in most laboratories. The most straightforward approach to overcoming this challenge is to detect and analyze respective CWA simulants, as they mimic the chemical behavior of CWAs by exhibiting similar chemical and physical properties with lower toxicity [1].
The researchers note that while these simulants have been widely utilized in experiments to help predict and correlate the degradation mechanisms and behaviors of their corresponding CWAs [1], it is unrealistic to expect that any simulant can satisfactorily represent all the properties of a given CWA [22]. For example, studies of organophosphate agent and simulant interactions in aqueous solution have reported that DMMP and DIFP mimic the interactions of soman and sarin with water reasonably well [23][24]. In contrast, studies on the adsorption of nerve agents in MOFs have found that the adsorption properties of soman and sarin are poorly correlated with those of DMMP and DIFP, respectively [25][26]. DFT models of the hydrolysis reaction mechanism have also revealed that many commonly used simulants in the literature, like DMMP, demonstrate large energy barrier deviations from GB and GD [27], which underlines the risk of choosing simulants based on the literature precedent alone. In addition to closely matching the chemical structure of the CWA, the selection of an appropriate simulant evidently requires detailed knowledge and evaluation of the properties that strongly affect the process at hand, as the simulant that is most appropriate to simulate a particular process in a particular environment may not be the best choice for all processes in all environments [22][28]. First-principles calculations and other computational approaches have thus become of special importance in this field, both for gaining insight into the relevant properties of ideal simulants for experimental study and for modeling the behaviors of real CWAs in a given system of interest.

2.2. Degradation Mechanisms

The proposed mechanisms of CWA degradation in the current literature are predominantly hydrolysis and oxidation [1]. Nerve agent removal occurs mainly via hydrolysis but differs depending on the type of CWA, particularly with respect to the reaction products. Hydrolysis of the nerve agent GD generates pinacolyl methylphosphonic acid (PMPA) and hydrofluoric acid. In contrast, ethyl methylphosphonic acid (EMPA) and the organosulfur compound 2-(diisopropyl)aminoethanethiol (DIAT) are the hydrolysis products of VX [29]. GB, not pictured here, hydrolyzes similarly to GD, with a hydrofluoric acid product accompanied by isopropyl methylphosphonic acid (iPMPA). Besides differences in their products, GB and GD have greater volatility and reactivity to water than VX, persist for a shorter time in the environment (hydrolyze at a faster rate), and have less complex reaction mechanisms [30]. In general, the various alkyl methylphosphonic acid (AMPA) compounds produced in the degradation of these and other nerve agents can all be even further hydrolyzed into the stable product of methyl phosphonic acid (MPA).
Degradation strategies for HD include hydrolysis, dehydrohalogenation, and selective oxidation [11][31][32]. An important obstacle of degradation via hydrolysis, which arises in both mustard agent and nerve agent removal, is the formation of acid byproducts that can lead to catalyst poisoning and inhibition of subsequent reactions. While this issue can often be confronted with modifications to materials and operating conditions, the hydrolysis of HD is also primordially rate-limited by the compound’s immiscibility in water [33][34]. Likewise, the degradation of sulfur mustard by dehydrohalogenation is considered too slow [11] since it typically requires a high pH environment that is corrosive to most materials [34]. Given these roadblocks, oxidation is the most effective mechanism for HD removal in real-time applications. Sulfur mustard oxidation can be partial or complete, producing desirable and undesirable products. Partial oxidation to sulfoxide (HDO) is an attractive decontamination strategy, as this product displays improved chemical stability that makes it rather inert towards biological systems [33]. On the other hand, complete oxidation produces the di-oxidized product sulfone (HDO2), which has vesicant properties similar to the parent HD [35]. Selective partial oxidation is therefore required for the safe degradation of HD to the nontoxic HDO [33][35]. For a 100% selective reaction to be achieved, mild oxidizing agents such as photosensitizers must be used [31] and exceedingly careful monitoring must be enforced to avoid detrimental over-oxidation to HDO2 [33].

3. CWA Removal by Metal–Organic Frameworks (MOFs)

3.1. Structural Features of Promising MOFs

While MOFs offer a large variety of structures for use against CWAs and emerging hazards, their exploitation depends critically on understanding the structure–activity relationship needed for efficient uptake and decomposition under operationally relevant battlefield conditions. A principal quality to consider when evaluating these materials for CWA removal is thus their stability and reactivity toward environmental constituents, particularly water. MOF functionality in humid conditions can be determined by several thermodynamic and kinetic factors, including the strength and geometry of metal–linker coordination bonds, pore sizes and connectivity, hydrophilic or hydrophobic framework components, and metal ion valency [36]. Many MOFs show limitations of weak mechanical and chemical stability in the presence of water that stems from hydrophilic functional groups, easily accessible active sites, water-susceptible linkages between metal nodes and ligands [37], or some combination of the three. In chemical reaction applications, these features can also lead to problems beyond structural stability, such as hindered target species adsorption and slow reaction kinetics.

3.2. Nerve Agent Hydrolysis

In the heterogeneous catalytic hydrolysis of organophosphorus-based nerve agents, MOFs with Zr6 nodes and displaceable -OH and -OH2 ligands such as UiO-66, NU-1000, and MOF-808 are among the fastest synthetic catalysts reported to date [6][7][19][38][39][40]. While the effectiveness of these MOFs towards nerve agents and simulant hydrolysis has been widely examined both experimentally and computationally, several puzzles still exist regarding the most kinetically favored hydrolysis mechanism, the performance of solid-state materials, and the role of environmental water.

3.3. Sulfur Mustard Oxidation

As stated previously, oxidation is thought to be the most effective strategy for the degradation of sulfur mustard, and selective partial oxidation is necessary for achieving decomposition into a nontoxic product. Complete selective oxidation requires a mild oxidizing agent, as strong agents such as hydrogen peroxide or tert-butyl hydroperoxide are often observed to generate both partially and fully oxidized products [35][41]. The most desirable mild oxidant is singlet oxygen (1O2), a reactive species commonly produced from ground state O2 using a photosensitizer [42]. Unfortunately, many prominent photosensitizers have a proclivity to aggregate in aqueous media, which diminishes their ability to absorb light and produce 1O2 [35][41][43]. MOFs are an attractive potential solution to this problem, as their tunable networks allow easy incorporation and post-synthetic modification of an array of discrete photoactive moieties at their organic linkers, and their 3D structures allow those moieties to be isolated by surrounding metal nodes [11][44].
Like nerve agent hydrolysis, the most promising and most frequently investigated MOFs for HD photooxidation are Zr-based. In addition to chemical stability, the high valence metal nodes in Zr-MOFs offer excellent thermal stability and reusability [44], making them especially appealing supports for generating singlet oxygen [45] and subsequent catalytic and selective oxidation [42]. Many research efforts have thus been motivated to design and utilize Zr-MOFs as photocatalysts.

This entry is adapted from the peer-reviewed paper 10.3390/nano13152178

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