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Chapter – 1 Introduction


In the history of mankind, microorganisms have played a key role and have made an
enormous social impact and are of economic importance. Without the awareness of their
existence, man has earlier used them in the production of food and beverages. The
knowledge on the production of chemicals such as alcohol and organic acids through
fermentations has been relatively new and the first documented evidence appeared in the
second half of the 19th century. Lactic acid was the first optically active organic acid
produced through industrial fermentation in USA in 1880 (Sheldon, 1993). Later in 1921,
Chapman documented a number of early industrial fermentation processes for organic
chemicals (Turner, 1998). In course of time, microorganisms were identified that could
modify certain compounds by simple, chemically well defined reactions, which were
further catalyzed by enzymes. Nowadays, these processes are termed as
. The essential difference between fermentation and
biotransformation is that a number of catalytic steps are present between transformations
of a substrate(s) to the product in fermentation, while a biotransformation process; there
are only one or two steps involved. Another distinguishing factor is that the chemical
structures of the substrate and the product resemble one another in a biotransformation,
but may not be true in case of fermentation.

Many chemical processes and routes were established for producing different chemicals
which are used as starting materials for producing many industrially important bulk
chemicals and fine chemicals of commercial value. However, the commodity chemicals
derived by this chemical route generate lots of toxic emissions and discharges that pollute
the environment and the water streams. In this regard, industrial biotransformation holds
interesting promises for society to contribute to a more sustainable economy in future.
Compared to current chemical production processes, cases have been identified where
industrial biotransformation has resulted in the production of high value products from
cheaper raw materials with low amounts of energy inputs and release of emissions. The
basic advantages expected using the biotechnology approaches are the bioconversion or
biotransformation is environmental-friendly and allows clean and mild synthesis with
high selectivity and yields, generation of novel products, cost reduction in the production

Chapter – 1 Introduction

process, the developed process uses less energy, and generates less waste vis-a-vis
chemical processes. In the field of fine chemicals, the main application lies in the
exploitation of the outstanding properties of the biocatalysts with respect to
chemoselectivity, regioselectivity and, especially, stereoselectivity for the production of
enantiomerically pure compounds.

Further, recombinant DNA technology has raised high hopes that it would speed up the
technological advances. Nevertheless, a very limited amount of progress has been made
using this technology for the development and application of bioprocesses for low-cost
bulk chemicals. Some of the flagship bioprocesses of today that have reached commercial
status nearly took 10 to 20 years for their development. For example, the acrylamide
process took 20 years for its development and the Lonza process for L-carnitine took 15
years. Despite the fact of the slow pace in the development of a bioprocess, many
traditional chemical companies such as Dow Chemicals, DuPont, Degussa AG, etc. are
under pressure from investors these days to use microbial or enzymatic transformations in
their production processes due to their eco-friendly, clean and green features, to catalyze
chemical reactions leading to the production of various bulk or fine chemicals. This
major shift towards bioprocesses is mainly to establish whether natural feedstocks can
become economical and advantageous over the depleting fossil fuel resources and soaring
crude oil prices.

Nitriles are organic compounds containing a carbon-nitrogen triple bond and commonly
occur in nature, in particular cyanoglycosides and cyanolipids are formed by a number of
plants especially among the members of family Brassicaceae (Conn, 1981). On the other
hand, nitriles such as acetonitrile, adiponitrile and acrylonitrile are widely manufactured
by the chemical industry. In general, nitriles are toxic in nature due to the cyano group
and are generally non-biodegradable. The transformation of nitriles to carboxylic acids is
of synthetic importance, because a variety of carboxylic acids are produced from nitriles
and the corresponding nitrile educts are easily accessible. Commercial success of
hydrolytic enzymes (Kazlauskas, 2004, Domínguez de María, et al., 2005) in past two
decades resulted in intensive search for the next generation hydrolytic biocatalysts
especially for nitrile hydrolysis, as illustrated by the growing number of articles dealing

Chapter – 1 Introduction

with development and application of nitrile hydrolyzing biocatalysts. (Thuku et al., 2009;
Martinkova et al., 2009; Martinkova et al., 2008; Zhu et al., 2007; Singh et al., 2006).

In the past few decades, nitrilases have gained increasing attention and have become
popular in the field of biotransformation and biocatalysis. Their ability to produce a
carboxylic acid from a corresponding nitrile has provided great potential for the use of
this enzyme as nitrile catalyst functioning under relatively mild reaction conditions. Some
of the microorganisms that have gained versatile application in the nitrile
biotransformation include the genus Rhodococcus, Pseudomonas, Arthrobacter,
Alcaligenes, Bacillus, etc. Some of the most well-known commercial processes
developed using nitrile bioconversion using different nitrile-converting microbes are the
manufacture of acrylamide from acrylonitrile and the synthesis of nicotinamide and
nicotinic acid from 3-cyanopyridine.

Acrylic acid and its derivatives (esters, salts, and amides) are the primary building blocks
in the manufacture of acrylate polymers and co-polymers with numerous applications
identified such as surface coatings, adhesives, sealants, textiles, adsorbents, dispersing
agents, flocculants, detergent builder, paper treatment, leather, fibers, personal care
products, non-wovens and as rheology modifiers. Acrylic acid is a commodity chemical
of considerable value, with an estimated annual production capacity of 4.2 million metric
tons (Weissermel and Arpe, 2003), which ranks at the 25th position in the list of organic
chemical products. Roughly three-quarters of the world production is converted directly
into acrylate esters, the remainder being purified into glacial acrylic acid (Burridge,
2002). The demand for acrylic acid has increased from a mere 400,000 tons in 1980 to
3.4 million tones in 2002. This increase in demand is mainly due to the increased use of
acrylate polymers to manufacture super absorbents finding their major use in the personal
care products such as diapers (more than 1 million tons annually). The remainder is used
to produce acrylates that are components of acrylic fibers, coatings, paints and inks. It is
predicted that the world demand is expected to rise to 4 million tons/year by 2009 with an
expectation to reach around 3.7% by the year 2011 (Donberg et al., 1992; Burridge,
2002; Anonymous, 2006; Anonymous, 2010).

Chapter – 1 Introduction

At present, majority of the world wide acrylic acid requirement is fulfilled by the
petrochemical industry through oxidation of propylene, a hydrocarbon gas that is a
byproduct derived from crude oil refining. Currently, 100% of commercial acrylic acid is
produced by partial oxidation of propylene. In the so-called single-step process, the yield
is almost 50-60% and generates large quantities of waste. Some of the problems
encountered during the acrylic acid synthesis using the chemical route include the
damage to the catalysts and the polymerization of the formed products, which cannot be
by-passed. Although propylene is easily available from fossil fuels, it would be desirable
to obtain acrylic acid and its derivatives from renewable resources at an equivalent or
lower cost. Unfortunately, petrochemical carbon sources are not renewable, which
implies that their use contributes to global CO2 emissions, and that they are expected to
become more scarce and expensive in the future. Based on the above facts, the present
study using the microbial route for production of acrylic acid was undertaken.