Q-SA√ESS: a methodology to help solvent selection for pharmaceutical manufacture at the early process development stage

Isoni, Valerio; Wong, Loretta; Khoo, Hsien H.; Halim, Iskandar; Sharratt, Paul

doi:10.1039/c6gc02440h

Cited by 35 publications

(36 citation statements)

References 33 publications

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“…Further refinement of streamlined, easy-to-use LCA methodologies for measuring the greenness of chemicals manufacture remains a top priority, and the evolution of LCA in pharmaceutical and chemical applications was recently reviewed. 84 More recently, Isoni and co-workers 85 developed an interesting LCA-based methodology for use in solvent selection during early process development of an API. Quick Sustainability Assessment via Experimental Solvent Selection (Q-SA√ESS) is a three-stage LCA approach in which the full cradle-to-grave life cycle of a solvent is evaluated.…”

Section: ■ Sustainability Metrics and The Environmental Impact Of Wastementioning

confidence: 99%

“…On the other hand, gauging environmental impact by assigning scores to various environmental criteria, albeit based on quantitative data, is also subjective and can vary very much from one company to another. As Isoni et al 85 put it, "Sustainability is an anthropocentric concept based on human judgement of the delicate balance of social, environmental and economic factors, and as such it is not uncommon to observe tradeof fs in borderline situations. "…”

Section: Sustainabilitymentioning

confidence: 99%

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Metrics of Green Chemistry and Sustainability: Past, Present, and Future

Sheldon

2017

ACS Sustainable Chem. Eng.

781

590

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The first green chemistry metricsthe E factor (kgs waste/kg product) and atom economy (mol wt of product/sum of mol wts of starting materials)were introduced in the early 1990s and were actually green chemistry avant la lettre. In the last two decades, these two metrics have been adopted worldwide by both academia and industry. The E factor has been refined to distinguish between simple and complete E factors, for example, and to define the system boundaries. Other mass-based metrics such as process mass intensity (PMI) and reaction mass efficiency (RME) have been proposed. However, mass-based metrics need to be augmented by metrics which measure the environmental impact of waste, such as life cycle assessment (LCA), and metrics for assessing the economic viability of products and processes. The application of such metrics in measuring the sustainability of processes for the manufacture of pharmaceuticals and other fine chemicals is discussed in detail. Mass-based metrics alone are not sufficient to measure the greenness and sustainability of processes for the conversion of renewable biomass vs fossil-based feedstocks. Various metrics for use in assessing sustainability of the manufacture of basic chemicals from renewable biomass are discussed. The development of a sustainable biobased production of chemicals meshes well with the concept of a circular economy, based on resource efficiency and waste minimization by design, to replace traditional linear, take−make−use−dispose economies.

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Section: ■ Sustainability Metrics and The Environmental Impact Of Wastementioning

confidence: 99%

Section: Sustainabilitymentioning

confidence: 99%

Metrics of Green Chemistry and Sustainability: Past, Present, and Future

Sheldon

2017

ACS Sustainable Chem. Eng.

781

590

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“…The need for reliable and quantitative methods for solvent selection in diverse applications has induced the development of several approaches, in some cases including green chemistry considerations. [2][3][4][5][6][7][8][9][10] The solvent can alter both the free energy of reaction (∆G) and the free energy of activation (∆G ‡ ) for each reaction step. Thus, for reactions with very negative free energy of reaction, the activation barrier determines the reaction time, product ratio (selectivity) and yield of a chemical reaction.…”

Section: Introductionmentioning

confidence: 99%

Solvent selection for chemical reactions: automated computational screening of solvents using the SMD model

Dalessandro¹,

Pliego²

2018

Quim. Nova

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Finding the most efficient solvent for a chemical reaction can demand costly experimental procedure and the screening is usually limited to few solvents. The use of theoretical methods could accelerate the search for the best solvent, able to promote most effective kinetics and thermodynamics of a reaction. In this work, it was proposed an automated procedure that calculates the solvent effect for a chemical reaction using all the 179 solvents available in SMD (solvation model density). The reaction of 2-bromoacetophenone with pyridine was used as a test. The SMD model correctly predicts the reactivity trends for five solvents, which experimental data are available. We have found that sulfolane, a less usual solvent, is the best one for this reaction. The present study points out that computational screening of large set of solvents using the SMD model is a viable approach and could be useful for chemical reactions optimization.

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“…Since the synthetic steps were conducted in heterogeneous media, recovery of the material requires only settling and filtration. This is important since the common recovery methods for polymers in solution often require a large amount of solvents (for precipitation) or high amounts of energy for distillation (for example, the distillation of tetrahydrofuran (THF) requires 5474 kJ kg −1 ) [ 80 ] Using the method reported for grafting CTS with synthetic polymer, its properties could be significantly enhanced. Additionally, it has been shown that, postmodification covalent crosslinking prepared this material for use in applications requiring stability in acidic conditions.…”

Section: Discussionmentioning

confidence: 99%

Synthesis of Biohybrid Particles by Modification of Chitosan Beads via RAFT Polymerization in Dispersed Media

Solimando

Champagne

Cunningham

2020

Macro Reaction Engineering

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in various fields including, water and wastewater treatment as adsorbents or coagulation-flocculation agents, medical applications as drug delivery systems, and the cosmetic or agriculture sectors. [2,4,8] However, the properties of unmodified CTS limit its use for some applications. Consequently, researchers have focused on the modification of CTS to improve and tune its properties, such as improved solubility in organic solvents, compatibility with various polymers, or affinity for molecules of interest. Possible chemical modifications of CTS include acylation, alkylation, quaternization, azidation, and phosphonation, [9-19] as well as the grafting of polymers. [20,21] One of the incentives for modifying CTS is to enhance its solubility in organic solvents for the preparation of advanced materials requiring chemical modification in specific solvents. For this purpose, N-phthaloylation was described by Kurita et al. using a method that involved the presence of small amounts of hydroxy-containing compounds for selective N-phthaloylation while avoiding O-6 phthaloylation. [22-24] N-phthaloylation with a high degree of substitution was prepared in acidic aqueous media by Ifuku et al. [25] The same group also successfully prepared N-(4-bromophthaloyl) chitosan exhibiting high solubility in common solvents, such as dimethylsulfoxide (DMSO), N,N-dimethylformamide (DMF), N,N-dimethylacetamide, and N-methylpyrrolidone (NMP). [9] The alkylation of CTS was reported in heterogeneous and homogeneous conditions for the introduction of specific chemical groups, such as aromatic structures, imidazole, sulfonate, or carboxylation. [26-31] Complexation of CTS with surfactants, such as sodium dodecylsulfate or sodium dodecylbenzenesulfonate was also described as a method for improving its solubility in organic solvents. [32-35] The grafting of synthetic polymers on CTS is a powerful and flexible tool among the strategies for preparing innovative materials. [20] Most reports on CTS modification by grafting have examined the use of free radical polymerization, [36-39] ring-opening polymerization, [40,41] γ-radiation, [38,40] or cationic polymerization [37,42] via both "grafting from" and "grafting to" approaches. Controlled radical polymerization, now more commonly known as reversible deactivation radical polymerization (RDRP), has provided a versatile tool for designing new CTSbased materials grafted with well-defined and functional (co) polymers. Atom transfer radical polymerization (ATRP) [43-51] Spherical macroscopic particles (beads) made from chitosan (CTS), a polysaccharide derived from the valorization of food waste, are converted into a biohybrid material by grafting poly(4-vinylpyridine) (P4VP) using a "grafting from" approach via reversible addition-fragmentation chain-transfer (RAFT) polymerization. Varying the time of reaction, and therefore the conversion, allows to readily tune the composition (CTS vs synthetic polymer content) and consequently the bead properties. P4VP has specific affinity for certain compounds. Th...

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Q-SA√ESS: a methodology to help solvent selection for pharmaceutical manufacture at the early process development stage

Abstract: A practicable, LCA based methodology has been developed to evaluate the sustainability implications of solvent selection during early process development for a batch manufacturing process for an API.

Cited by 35 publications

References 33 publications

Metrics of Green Chemistry and Sustainability: Past, Present, and Future

Metrics of Green Chemistry and Sustainability: Past, Present, and Future

Solvent selection for chemical reactions: automated computational screening of solvents using the SMD model

Synthesis of Biohybrid Particles by Modification of Chitosan Beads via RAFT Polymerization in Dispersed Media

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