Research Project-I (CH6993)

Topic

Reactive Extraction of phenol using sunflower

oil
by

Name: Mahima Baid

Roll number: 220CH1630

Under the guidance of

< Prof. Basudeb Munshi >

Department of chemical engineering

National Institute of Technology Rourkela

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 ACKNOWLEDGEMENT
With immense please I , Ms Mahima Baid prepared ‘Extraction of phenol’ project report as
part of the curriculum of ‘M.TECH in chemical engineering’.
I wish to thank all the people who gave me unending support.

I express my profound thanks to Prof. Abanti Sahoo HOD , Prof. Basudeb Munshi and all
those who have guided and helped me in preparation of this report.

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 Content

 Introduction
 Material and Method
 Types of Solvents
 Factors considering while selecting solvent
 Extraction techniques
 Conventional methods
 Unconventional methods
 Recovery of phenol
 Future scope
 Conclusion
 References

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 Aim:
 To extract phenolic compounds from biomass.
 To recover phenol using reactive-extraction method.
 To enhance the percentage yield of phenol using different reactive
extractants.

Introduction to Natural Phenolics

Chemical Compounds with equal to or greater than one benzene ring having one or more -
OH ion is known as phenolic(s), hugely classified in plants. They have the most secondary
metabolites (8100 known phenolic molecules), through polymerized compounds like tannins
to simple phenolic acids. These are pervasive in parts of plant and are vital for human diet.
They are the ingredients of plant foods (cereals, olive, legumes, vegetable and fruits) and
partly accountable for the flavour of foods. For instance, the sourness and acerbity of juices
and fruits. Among the six subclasses of a large class of phenolics one of them includes
Anthocyanins, called as flavonoids, are accountable for the indigo, vermillion, orange and
violet colours of most of the green commodities such as beets, onions, apple, and berries.
These react with O2 and are vital for the wine's preservation and ageing. They are identified
as utmost important compounds influencing flavour and colour difference among pink, red
and white wines; Plant phenolics include tannins, flavonoids, phenolic acids lignans [1].
Complexes of Benzoic acid say acidic ferulic and cinnamic are the further two sets of
phenolic compounds mainly present in food(s), esterified with a major phenolic compound in
coffee such as quinine as in alkaloids. Another specimen says, ferulic acid when reacted
alcohol and with hemicelluloses present in the wall of the cell, found in cereals. Tannins, one
of the subgroups found in our diets are of two types: (a) hydrolysable and dehydrated tannins.
Gallo tannins are an example of hydrolysable tannin(s), containing glucose core centre or
polyol also called ellagitannins esterified and reacted with gallic acid, or with hexahydroxy
diphenic acid.

1. Extraction by Solvents

1.1. Types of Solvents used for different methods

The rate of polyphenol(s) extracted and the amount is the outcome of the use of right solvent
[2-3]. Generally, aqueous acetone favors extraction of heavy polyphenol(s) while the lower
atomic mass flavanol(s) can be treated using methanol [4-7]. Ethyl alcohol is good and non-
hazardous for polyphenolic extraction [8]- [10]. An acidified organic non-polar solvent,

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mainly CH3OH or C2H50H, is used in developing anthocyanin-abundant phenolic extracts
from biomass. The solvent ruptures the cell membranes, at the same time dissolves the
anthocyanins and gives stability. Although, caution should indeed be considered while adding
excess acid as it hydrolyses sugar residues, throughout evaporation. To attain the yield of
anthocyanin extraction, weak carboxyl acids, such as methanoic or ethanoic, citric,
phosphoric, dihydroxybutanedioic acid and, and dilute strong acids, such as 0.4-3.1% of tri-
fluoro-acetic acid less than 1.1% of HCl are suggested[11], [12] . For the reduction of organic
non-polar solvent and extraction cost sulphured water can be used as extraction solvent [13].
As extraction temperature increases it promotes more analyte miscibility by improving mass
transfer. Moreover, enhancing the temperature supports solvents to penetrate inside the
medium, increases extraction, lowers the surface tension and dynamic viscosities. But
increasing the temperature very high can reduce the yield of phenolics.

For the extraction of various compounds, water the greenest solvent is a resourceful due to its
characteristics and moreover water is widely available, anti-toxic, clean, inflammable, and
sustainable in the environment [14], [15]. But it is unsuitable for less polar substance
extraction. In addition, replacing petroleum-based solvents by “Bio-solvents” is another
possible eco-friendly solvent. For example, “bio-ethanol” formed by fermentation. This
solvent is cheap due to the advancement of bio-refinery based procedures for the
fundamentals of lignin and cellulosic biomass, replacing ethanol [16], [17].

At temperatures below one-hundred-degree cations and anions (inorganic or organic) with

physio-chemical parameters forms ILs are known as liquid molten salts and another solvent
called natural deep eutectic solvents (NADES) are naturally present chemical mixtures that
exist at eutectic point temperatures lower than an ideal liquid solution. These green and clean
solvents are derived from “low-priced, rich and bio-degradable natural materials behave as an
alternative to the regular solvents and also thereby making the extraction process more
efficient and eco-friendlier.

Finally, the effort totals to reducing the price and sampling hours during regular extraction. In
each and every situation, the extraction step is necessary, as its result will evaluate the
discharge of analytes of the sample into the medium, and this permits the measurable
determination of the extract. Strategies for characterization and preparation of phenolic
samples [18]– [23] from biomass is given below [24]

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 Strategies for characterization and preparation of
phenolic sample from biomass [24]

1.2. Solvent Properties

A sum of properties is important while taking LLE as a sample method. Among these, the
solvent selection is extremely necessary to attain the goal of extraction. This includes either
the component extraction or the segregation of matrices elements. However, may be
sometimes it is possible that either of the LLE solvents participating in the extraction
operation can be selected meanwhile its properties is determined by other features too. For
instance, it is likely that for the liquified sample only the organic non-polar solvent can be
chosen. However, certain factors limit the nature of the solvent for instance, connected to the
chromatographic exigency. Also, in some situations extracting a significant amount of the
components is undesirable for further steps in the analysis as it requires necessary clean-up of
the extract. In some instances, a solvent is preferred when it extracts utmost of the analytes
but ensures not to liquidate (or extract) much of the sample and always able to attain a more
thorough extraction. For the chromatographic analysis the organic solvent extract is preferred
and the extracted analytes are segregated, dehydrated, and evaporated partly. Then, in next
step the treated sample is either reused or recycled. For the ease of get rid of it after
extraction the low boiling point solvent is selected to concentrate the analytes. But organic
phase volume may behave as a source of errors in determining the molarity of the analyte.
However, Solvents of high boiling points are usually kept away as they are not recovered
easily. The evaporation technique is time-consuming and might result in analyte deterioration

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or loss, especially when vaporization is essential. In the choice of a solvent the degree of
miscibility, the specific gravities, emulsions forming tendencies, also viscosities should be
considered. For the organic toxicity, chemical reactivity, and safety must also be well-
thought-out.

Some of the features of solvents and the miscibility of various solvents is based on
experimental results.

Fig: Features of Solvents

Image Source: Google

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2. Extraction Techniques

There is currently no widely acknowledged method for recovering all phenol molecules or a
specific molecule from biomass. As a result, an improved technique for recovering phenolic
chemicals from plant sources is required. Along with the greater extent of enzymatic activity
found in most sources, recovering polyphenols is a time-consuming process. As a result,
selecting an extraction method must be done with extreme caution in order to avoid chemical
changes to the target molecules. In this section there are updated guidelines for extraction
procedures used in identifying phenolic chemicals in plant materials, ranging from traditional
to unusual approaches.

2.1. Conventional Methods

Decoction, percolation, and Soxhlet extraction are few examples of traditional phenolic
compound extraction procedures. The decoction approach entails heating the sample for a
brief period or adding saturated water to the samples and letting the combination hold for a
short period. Thermally and chemically stabilized phytochemicals from fresh medicines are
most suited to this approach. In percolation process sample is crushed and placed in a
controlled volume system and solvent is added from the top. For the Soxhlet extraction
procedure the crushed materials are inserted in extraction chamber (which consists of
cellulose thimbles) placed above the collecting chamber and below a condenser. The solvent,
which has previously been put to the chamber is heated to form vapor and condensed using
sub-cooled water and thereby falling down in the chamber. Soxhlet extraction is a continuous
process where reflux is constant, requires shorter period and solvent than percolation
procedures[25], [26].
However, some drawbacks raise the unconventional techniques (MAE, UAE, SC-CO2, EAE,
and PLE) which includes less recovery of solvents, limited yields, longer residence time, and
enormous accumulation of residues.

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2.2. Unconventional Methods
Pressurized liquefied extraction (PFE), Super-critical CO2 extraction [27], ultrasound assisted
(UAE)[28], enzyme-assisted (EAE), microwave-aided extraction (MAE)[29], or a fusion of
these methods are examples of such techniques. According to the research, these innovative
extraction methods appear to be the preferred way over traditional methods since they
provide several benefits such as lower hazardous residues, better process repeatability, lower
solvent volume, higher yields, and shorter extraction times. These unconventional extraction
procedures were covered in the subsections below.

2.2.1.
Ultrasound Assisted Extraction
Ultrasound waves of extremely high strength sound vibrations say, around 18 kHz are used.
UAE's functioning is based on pressure fluctuations that create microbubbles, leading in
microturbulence and a high particle collision rate. Ultrasound vibrations induce
microparticles to collapse, so solvent can penetrate deeper into the cellular material,
disrupting cell walls and boosting intracellular chemical release into the extraction media.

2.2.2. Supercritical Fluid Extraction

It is the technique of separating one component (the extractant) from another (the matrix)
using supercritical fluids as the extracting solvent. It is often performed on a solid matrix,
although it may also be performed on liquids. In the supercritical zone, the solvent's mixed
behaviour as both a liquid and a gas facilitate and improves mass transfer [30]. Methanol,
water, Ethane, argon, and carbon dioxide are some of the solvents utilised in SFE, with
carbon dioxide being the most widely used owing to its anti-toxic nature, safety, easy to

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reuse, and normal room temperature, which is essential for thermolabile mixtures). However,
CO2, on the other hand, is typically blended with polar co-solvents like ethanol for the
extraction of polar polyphenols due to its non-polar nature. CO2's solvating capacity is
increased in this way. To raise the solubility of phenolic plants fractionated SFE is used to
extract polyphenols, firstly supercritical CO2 is used and then polar solvents. For instance, a
fractional SFE performed by Braga et al. of pine bark; firstly, non-polar CO 2 soluble
compounds is removed, and then polar molecules is eliminated by using ten percent EtOH.
This method attained a better yield of molecules say catechin and epicatechin than Soxhlet
extraction. Because EtOH in second step improves polyphenol withdrawal. As a result, SFE
outperformed traditional extraction methods by decreasing the quantity of solvent needed,
being adaptable enough to extract particular chemicals, and working at low thermal
environment, which maintains the value of the extracted product.

3. Recovery of phenolics from Biomass

The recovery of bio-active, viable, and refined biomolecules from plant materials is a
necessary stage in the reuse of environmental assets for extremely important to develop in
cosmetic applications, food additives, medicinal and preservatives, nutritional including
vitamin supplements. Natural extract extraction is influenced by a variety of elements,
including the technique used, the parameters linked with the procedure (such as temperature,
duration, as well as solvent), and the composition of the raw resources [31]. Phenolic
chemicals are metabolites found in cell vacuoles, according to research [32]. So, it is
significant to encourage the loosening of pore(s) or the disintegration of the cell membrane to
enable chemicals to be discharged into the solution. In this regard, it is critical to investigate
all process factors to optimise the extraction method's huge potential for a highly efficient
process. All variables in the process must allow for the production of an acceptable and
excellent quality final product (eco-extract), as well as the maximum extraction. Researchers
also looked at the consequence of unlike solvents on antioxidant phenolic(s) from pine by-
products, and discovered that the composition varies depending on the solvent employed. For
example, an experiment by Venkatesan and colleagues [33] the impact of diverse solvents
(such as isopropanol, ethyl alcohol, propanone, methyl alcohol, and acetonitrile) was
analysed to find the anti-oxidant activity of Pinus bark. After the research, their result showed
that phenolic(s) with reduced molarity of ethanol and acetonitrile are favourable for high
antioxidant activity.

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3.2.1. Reactive extraction

The petrochemical, medicinal, surveying, nutraceutical, and nuclear sectors chemically

produces soaps, antibiotics, polycarbonates, linear alkylbenzene sulfonates, Polyurethanes
and amides by a chemical treatment followed by an aqueous extraction process using this
above-mentioned method [34].

For phenol recovery, in reactive extraction molecules are converted to phenoxide (i.e.,
phenolates) and then by a neutralization reaction compound solubilizes into aqueous phase
and segregated from other insoluble compounds in the organic medium by Liquid-Liquid
extraction. Zha et al. [35][36] reported that the reaction for phenol recovery (C6H6O) is
flexible and occurs instantly. Reactive extraction uses a specific extractant that yields a
greater partition value has been proposed as a possible method for recovering phenols. Both
chemical and physical phenomena are linked in reactive extraction, which was created to
improve separation using solvent extraction (dissolution and dispersion of the reaction
components). Extractants have a significant role in the reaction and separation of reactive
extraction. It mainly depends on various factors such as formation constant, complexes types,
the partition coefficient, extent of extraction, loading proportion, (1:1, 2:1, etc., phenol-
extractant reaction, solvent nature (raffinate and extract), temperature, etc. This separation
process has several advantages, including (i) being effective at high substrate concentrations
in the wastewater stream, (ii) the phenol can be recovered and the extractant reused, and (iii)
products formed are immiscible with the reaction phase.

3.2.2. Alkaline solvent extraction

Selective Alkaline Extraction Method: This is an integration of solvent extraction/distillation,

and a selective alkaline extraction technique. Firstly, a suitable solvent is used to extract a
fraction containing primarily the methoxyphenols and other thermally stable components in
the biomass Then fractionally distilled to obtain a crude MP-mixtures. boiling between 165
°C and 315 °C. In the subsequent step, the crude MP-mixture is preferentially extracted by
exploiting slight differences between the pH of the phenolics present. As a result, a
bioproduct containing phenolic compounds is obtained [37].

Future Scope

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  To employ Reactive Extraction successfully in recovery of chemical species from
dilute solutions with high selectivity and capacity.
 To explore the possibilities of reactive extraction, further studies are to be carried out
with different phenol(s) dissolved in different categories of extractant and diluents.
 Environmentally friendly solvents to be used in the reaction are major challenges with
this method.

So, in near future, there is need to explore more environment friendly solvents like 1-
decanol liquid for the separation method.

Conclusion

Because of their characteristics, phenol(s) have gotten a lot of interest. Seeking innovative
phenol extracts from various plants has evolved a prominent focus on health as well as
medical study in recent years. This review gives an up-to-date and in-depth look into
extraction, refinement, evaluation, and quantization of phenol(s)

To conclude, new ecologically friendly approaches have been investigated to lower the
significant volumes of organic-solvents, energy consumption, and waste creation associated
with traditional solvent extraction operations. Although there has been progress in replacing
conventional methods with non-conventional ones, more work is needed for the thorough
understanding of the methods and intensifying it. “UAE, MAE, SFE, and PLE”, are only a
few of the new potential methods for extracting bioactive chemicals in accordance with

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 Green Chemistry principles. In terms of the extraction stage, the most suited procedures vary
according compounds to be recovered and the ultimate functionality/application desired.
However, there is no one method of extraction that can be used to extract all phenolics as the
phenolic content of various species varies.

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