what properties does a liquid need to have to work as a biosolvent

Abstruse

One of the current trends in dark-green analytical chemical science is the introduction of green solvents, some of which are biobased. At the same time, the development of the biorefinery concept has immune more biochemicals to be obtained with increased efficiency and from a wider range of feedstocks. The first examples of the utilise of biosolvents in analytical applications included extractions performed with alcohols, esters, and terpenes. Notwithstanding, many more applications of biosolvents in extractions of bioactive compounds from various establish materials have also been reported, which hints at a wider range of potential analytical applications of biosolvents. It should also be noted that the biobased solvents practical in belittling chemistry are non ever green, as some of them are toxic towards aquatic organisms.

Graphical abstract

Introduction

The concept of green analytical chemical science (GAC) involves the introduction of the 12 principles of green chemistry into analytical laboratories [one]. The main aims of this push for greener chemistry are the miniaturization of analytical techniques, specially extraction techniques, the simplification of procedures in society to avoid unnecessary steps, and the awarding of less chancy reagents, derivatization agents [2], and solvents [iii]. The optimal way to implement the principles of GAC is to utilise solventless extraction techniques. It should exist noted that the concept of cleaner belittling chemistry is non new; it was intuitively introduced into analytical chemistry long earlier the acronym "GAC" was first used.

1 of the trends in modernistic analytical chemistry is the introduction of dark-green solvents [4]. These can be less harmful organic solvents, ionic liquids, deep eutectic solvents (DESs), or supercritical fluids [five]. Nonetheless, the latter three examples crave the awarding of complex devices or modified equipment, or their greenness has been questioned, equally in the example of ionic liquids, given that they are more often than not characterized by high toxicity towards aqueous organisms [6]. While the negligible vapor pressures of ionic liquids are a favorable characteristic, because there is then no possibility of exposure through inhalation, this property makes ionic liquids incompatible with gas chromatography. DESs are a grade of ILs that are usually relatively inexpensive and easy to produce, and are biodegradable [vii]. Another advantage is the possibility of obtaining DESs from biosources; this is particularly true of choline derivatives, organic acids, and aminoacids [viii]. The primary limitations on their utilization in belittling chemistry are their loftier viscosities and their solid state at room temperature. Among supercritical fluids, the almost ordinarily used compound is carbon dioxide, which is nontoxic, incombustible, easily available, and inexpensive. Its properties can exist altered past irresolute the temperature and pressure, and it can easily be separated from the extract past relaxing the conditions to room temperature and pressure level [ix]. The main limitations of supercritical fluid engineering science are the need for sophisticated equipment and its high energy demands. Nosotros tin therefore conclude that the main focus of the search for practicable green solvents should be less harmful organic solvents.

1 of the main lines of greenish solvent development is the awarding of biobased solvents that are of renewable origin (which are usually readily biodegradable and less toxic than most of the solvents that derive from petroleum-related sources) in both analytical chemistry [8] and general dark-green chemistry [10]. As the applied application of biobased solvents appears to be on the most horizon in many areas of chemical technology, the potential applications of these solvents in analytical chemical science have been largely overlooked. The primary potential applications of biobased reagents in analytical chemistry relate to spectrophotometric and electrochemical techniques. Indeed, as discussed in [11], natural products tin be used directly or with small preparation every bit reagents in many analytical procedures, just the main issue encountered when applying them is a tendency for higher limits of detection.

1 of the current trends in chemical technology is to shift the sources of chemical feedstocks from fossil fuels to biobased ones [12]. Biomass, a by-product of many areas of agriculture and industry, is valorized to obtain useful chemicals or fuels. Industrial biomass valorization is currently undergoing rapid evolution; a wider range of biomass feedstocks are being considered and a greater fraction of the biomass is being valorized. The shift from petroleum-based sources towards renewable sources of materials besides seems to be unavoidable for analytical laboratories. The crucial question to reply in this regard is if analytical chemistry no longer needs to rely on petroleum-based solvents. In other words, the question is whether analytical chemistry can manage in a biobased economy, and even benefit from it.

Feedstocks and a brief introduction to the biorefinery concept

Most of the chemicals currently produced industrially are petrogenic in origin. The transition from a fossil-fuel-based economy towards a biobased economy is unavoidable in the case of chemical and fuel production. To meet these demands, the concept of biorefineries has been intensively adult in recent years. The products of the processing of unlike feedstocks by biorefineries can be of energetic value or of material value. The feedstock—the raw material that is processed in a biorefinery, analogously to how crude oil is refined in a traditional refinery—can be obtained from various sources. The most common of these are [13]: agricultural, such every bit waste matter from production (which ofttimes originates from citrus processing [14]) or from crops grown for this purpose; forestry and wood processing; processing waste from other industries, and biomass of marine origin, such as algae.

The iii principal pathways to obtaining solvents from biosources are the fermentation of carbohydrates, vegetable oils, and the steam distillation of wood [fifteen]. In the second case, the products of biomass processing are platform chemicals that are afterwards used in syntheses of desirable products. Examples of building block chemicals used in biosolvent production from lignocellulosic mass include the following [sixteen]:

• three-Hydroxypropionic acid, with i,3-propanediol, propiolactone, and malonic acid every bit finish products

• n-Butanol, ethanol, methanol, and due north-propanol, with the aforementioned or other molecules (such as acetic acid, acetone, acetaldehyde, ethyl acetate, butyl acetate, isobutene, or p-xylene) as final products

• Furans, with cease products such as formic acrid and tetrahydrofuran

• Lactic acid, with butyl lactate, ethyl lactate, and propyl lactate equally finish products

• Succinic acid, with terminate products of i,4-butanediol and tetrahydrofuran

Another important production that is widely recognized to exist a chemical derived from biomass is ethanol. It is obtained from sugar-containing plants or institute waste product, lignocellulosic mass, marine algae and microalgae, straw, and other sources. Solvents that can exist obtained from bioethanol include ethyl esters (through ethylene), acerb acid, due north-butyl acetate (through ethanal), and other esters (through acerb acid) [17].

Another biobased solvent worth mentioning, ethyl lactate, is obtained from corn and soybeans by fermenting the biomass and reacting 2 fermentation products—ethanol and lactic acid [18]. As information technology is biodegradable, nontoxic, and exhibits relatively low volatility, ethyl lactate is used to extract phytochemicals [19].

Biosolvents used in analytical chemical science

Extraction with biobased solvents

There are already belittling procedures in which traditional solvents have been replaced with their biobased counterparts. 1 example of a biobased solvent already used in belittling exercise is D-limonene, which is employed instead of toluene to determine moisture with the Dean–Stark apparatus [20]. Importantly, this substitution was recommended past the American Oil Chemists' Society (AOCS) for official method Ja 2a-46, which is used routinely. Irresolute solvent did non significantly bear on procedural operation. This terpene has as well been applied instead of n-hexane for the determination of fats and oils in olive seeds [21]. Apart from switching to a less toxic and less hazardous solvent, the proposed procedure included a successful solvent recycling stride. Thus, the possibility of recovering and reusing D-limonene is another advantage. Information technology has also been used every bit substitute for n-hexane when determining the total lipids in various foods [22]. The ecology impact of the extraction solvent is reduced by selecting the (relatively) beneficial D-limonene equally solvent equally well as past significantly reducing the volume of solvent used. This can be achieved through the use of microextraction techniques, such as dispersive liquid–liquid microextraction (DLLME) [23]. β-Cyclodextrin was determined using a DLLME method in which 200 μL of D-limonene were employed equally extraction solvent and one mL of acetone as dispersive solvent. DLLME combined with spectrophotometric decision yielded an adequate LOD and linear range. Interestingly, β-cyclodextrin forms a colored complex with β-carotene, a bioreagent obtained from carrots, which means that the belittling procedure is completely biobased. However, information technology should be mentioned at this point that D-limonene is highly toxic towards aquatic organisms [24].

Menthol has also been used as a biobased extraction solvent in the DLLME of 5 phthalate esters [25]. Fifty milligrams of menthol were applied together with i.25 mL of acetone, and the resulting LODs were within the range one–8 μg L⁻¹. The precision, expressed as the coefficient of variance, was within the range 4–8%. Diethyl carbonate, a light-green solvent that can exist synthesized from ethanol, has been applied to extract chlorophenols from water using DLLME [26]. Metrological values were comparable with those obtained using other belittling procedures based on extraction with toluene, chlorobenzene, or butyl acetate.

A polyethylene glycol water solution was applied for the microwave-assisted extraction of flavones and coumarin from plant samples [27]. This process permitted almost 100% efficient extraction in 2–half-dozen min depending on the analyte, and the performance was better than that achieved with methanol.

Several biosolvents were tested for the extraction of biocides from fish tissue samples via vortex-assisted matrix solid-phase dispersion extraction [28]. Almost all of the investigated solvents—acetone, hexane, ethyl acetate, tetrahydrofuran, a methanol–acetic acid mixture, ethanol, methanol (notation that all of these are biosolvents except for hexane)—permitted extraction efficiencies of >96%. As these solvents all met the required analytical performance criteria, other factors were considered when selecting the extraction solvent. Ultimately, ethanol was chosen, as information technology was the least toxic and has benign physicochemical backdrop. Another study showed that ethyl acetate is the all-time option for extracting fatty acids from salmon tissues [29], as it was plant to allow a slightly better extraction efficiency than those attained with 2-methyltetrahydrofuran, cyclopentyl methyl ether, dimethyl carbonate, isopropanol, ethanol, ethyl acetate, p-cymene, and D-limonene.

An investigation aiming to discern the best biosolvent from among ethanol, D-limonene, and ethyl lactate to apply in the pressurized liquid extraction of thymol from thyme essential oil [xxx] showed that all iii biosolvents facilitated the extraction of thymol, but D-limonene was observed to give the best response, due to its lipophilic backdrop.

Information technology should exist noted that the number of analytical procedures that utilize biosolvents is still not very high. Biosolvents are more widely applied in other branches of chemistry, especially to obtain biologically active compounds from plant materials. This fact demonstrates the potentially broad applicability of biosolvents in analytical extractions, albeit under 2 conditions. The first is that the extraction efficiency of target compounds should be close to 100%. The second condition is that it is possible to obtain a high-purity biosolvent or a biosolvent contaminated with compounds that are not interferents. When the biosolvent is used in chromatographic techniques, any contaminants of the biosolvent must non elute together with the analyte, and when the concluding decision is fabricated spectrophotometrically, the contaminants must not absorb radiations at the wavelength at which the analyte absorbs. Biosolvent purification can be achieved through well-established methods such equally distillation or the application of a dehydrating or deoxygenating agent [31].

An example of a biosolvent applied in constitute material processing is eucalyptol, which tin can be equally constructive at extracting phenolic compounds from algae equally a i:1 v/v mixture of dichloromethane–methanol mixture [32]. Another example is the awarding of methyltetrahydrofuran for the extraction of steroids from rapeseeds equally efficiently as northward-hexane [33]. A chloroform–methanol mixture or n-hexane can be replaced with 2-methyltetrahydrofuran–isoamyl alcohol or 2-methyltetrahydrofuran–ethanol [34], or with ethanol and ethyl acetate [35], for the extraction of lipids from microalgae.

Biobased versus green solvents

The solvents that are generally applied as mobile phases in liquid chromatography are methanol, ethanol, and acetonitrile. The latter cannot be considered a biosolvent, and it causes more environmental problems than the other 2 solvents. The application of methanol and ethanol with advisable modifiers should give satisfactory results in the bulk of liquid-chromatographic separations. There are too enough of polar solvents that are applied to extract polar or moderately polar compounds from many solid matrices. It may be more problematic to find suitable nonpolar biobased solvents for the extraction of nonpolar analytes from h2o samples. The primary options in this area are terpenes, which are associated with certain environmental bug [36]. The primary business here is their high potential to facilitate the generation of photochemical smog, which reminds us that a solvent derived from a biosource is not necessarily green. This upshot has already been discussed in relation to furfural, which is obtained from biosources but is considered to be toxic and carcinogenic [37]. Many of the solvents included in Table 1 have been investigated regarding their applicability as green solvents [38], and the findings support the statement that analytical chemistry lacks opportunities for the application of nonpolar biobased solvents except for terpenes. Table 1 lists biosolvents together with their greenness scores, their toxicities towards fish, and their biodegradabilities. While most of the biobased solvents are readily biodegradable, some of them (such as terpenes) are toxic towards fish. Results for the GSK assessment of solvent greenness bespeak that some of the biobased solvents are problematic.

Table 1 Bones greenness parameters of biobased solvents

Full size tabular array

Some authors state that the greenness comparison should be contextualized and that the cess should be done for a detail process or application (see the instance written report of ILs in [39]). The assessment of biobased solvents is a multistep process in which the number of candidates is trimmed at each footstep and the candidates are considered in increasing particular as the process proceeds [xl]. Most of the steps are relevant to analytical applications: pick of replacement candidates, in silico prediction of properties, testing physical properties, toxicology assessment, and greenness and life-wheel cess.

The benefits of deriving solvents from carbohydrates in corn, from lignin in biomass, and from carbohydrate non-corn feedstocks were assessed based on a comparison of life-cycle greenhouse gas emissions with those of their fossil fuel-based counterparts (expressed in percent, with positive values showing increased greenhouse gas emissions and negative values indicating decreased emissions) [41]. Acetic acrid obtained from corn carbohydrate is associated with a 44% increase in emissions, whereas the values for ethyl lactate and n-butanol are −87 and − 66%, respectively. Obtaining methanol from lignin-based material results in a 76% decrease in greenhouse gas emissions. The values for solvents obtained from not-corn carbohydrate-rich materials (sugarbeet, potato juice, white potato molasses, sugarcane, and switchgrass) were −168% for n-butanol, −94% for i-butanol, −7% for acetic acid, and 12% for p-xylene. This shows that biobased solvents are not always greener options, or are at least not greener in all aspects.

The utilise of D-limonene derived from citrus waste matter every bit a substitute for toluene in cleaning applications shows that biosolvent utilization is feasible only in areas that generate high levels of citrus waste [42].

Outlook

Based on the aspects described in a higher place, nosotros can await the use of biobased organic solvents in belittling applications to gain in popularity. Still, the driving force for the development and application of new biosolvents is (green) chemical applied science, not analytical chemistry. Therefore, analysts who wish to apply new biobased solvents or develop novel analytical procedures based on such solvents need to monitor trends in green chemistry and technological separation processes. Greenness assessments of biosolvents should be supported by fast computational methods, such as quantitative structure–activity relationships [43]. The search for water-insoluble and green biosolvents that are applicable to extractions is particularly important, equally such solvents are urgently needed.

The development of and research into applications of biosolvents in belittling extractions and related fields are becoming increasingly noticeable. The focus so far has largely been on alcohols, esters, and terpenes. It appears that some of the solvent requirements of analytical chemistry can be satisfied by polar biosolvents, which are practical as extraction solvents or mobile-stage constituents in liquid chromatography, only it is difficult to find nonpolar biosolvents that are applicable in extractions of lipophilic substances from polar media. The present discussion of biosolvents shows that about of them (specially the polar ones) can be treated as greener solvents, only too that biobased solvents are non automatically light-green (this is true of terpenes, for instance).

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1. Department of Analytical Chemical science, Chemical Kinesthesia, Gdańsk University of Technology (GUT), 11/12 One thousand. Narutowicza St., lxxx-233, Gdańsk, Poland

   Marek Tobiszewski

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Tobiszewski, M. Belittling chemical science with biosolvents. Anal Bioanal Chem 411, 4359–4364 (2019). https://doi.org/10.1007/s00216-019-01732-two

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• Received: 21 November 2018

• Revised: 06 Feb 2019

• Accustomed: 27 Feb 2019

• Published: 26 March 2019

• Outcome Date: 19 July 2019

• DOI : https://doi.org/10.1007/s00216-019-01732-two

Keywords

• Biobased solvents
• Biobased economy
• Green belittling chemistry
• Renewable resources
• Biorefinery
• Extraction

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