9-decanoic acid methyl esters: A perspective into green solvents

Industry : Renewable Chemicals    

9-DAME is a medium-chain saturated fatty acid and has a number of commercial uses which include flavorings, supplements, cosmetics, soaps, dietetics, etc. Coconut oil and palm oil are the key raw materials used for manufacturing 9-decanoic acid methyl ester and other oleochemicals.

The Philippines is the world’s largest producer of coconut oil. Indonesia and Malaysia together account for around 85% of the global palm oil production.

9-DAME being naturally derived, adds to the popularity of these materials in manufacturing various products related to flavors, fragrances, pharmaceuticals, etc. A majority of the oleochemicals today are produced using naturally derived raw materials as these are environment-friendly and are renewable feedstock.

Palm oil, palm kernel oil, and coconut oil can be converted into methyl esters and glycerin by trans-esterification process. Trans-esterification of natural glycerides with methanol to form methyl esters is an important reaction which has been widely adopted in the soap and detergent manufacturing industry.

In the trans-esterification process, triglyceride i.e. fat or oil reacts with alcohol to form glycerol as well as methyl esters. The methyl esters, thus formed, are processed further and fractioned into different methyl esters with a single carbon chain length ranging from C6 to C18 fractions.

Different proprietary processes have been developed by various manufacturers to produce green chemicals, fatty acid methyl esters, etc. wherein 9-decanoic acid methyl ester is also produced as a co-product. Metathesis is one such process which has been patented by key manufacturers.

Metathesis refers to a catalytic reaction that involves interchange of alkylidene units among compounds containing one or more double bonds via the formation of carbon-carbon double bonds. Metathesis may occur between two same molecules, which is also known as self-metathesis, or between two different molecules also known as cross-metathesis.

Market players are developing new methods to manufacture 9-DAME. One such example is that of Cargill, Inc. The company has developed a process for producing industrially relevant chemicals from renewable sources such as linoleic acid which can be obtained from various vegetable oils. This process can be used to produce 1-octene along with methyl ester of 9-Decanoic acid and butadiene from linoleic acid via an enzyme-mediated isomerization reaction, followed by a metathesis reaction with ethylene.

Extraction cost of esters from naturally occurring oils poses a major challenge. The cost of extraction is high owing to the high cost of catalyst that is essential for metathesis. Also, the yield obtained from natural sources is very low as compared to that obtained from synthetic sources. Another reason attributing to the high cost is the varying quality and volume of glycerol produced, which is mostly obtained during biodiesel production.

9-Decanoic acid methyl ester prices are expected to be influenced by processing cost and energy consumed and will overcome by adapting bulk production process. A technological breakthrough for replacing the current extensive production process is needed to control the product pricing.

Companies are thus focusing on merger and acquisition to enhance their technology and thus expand their product portfolio. These strategies have long term effects on the pricing policies which is likely to play a pivotal role in positioning their products in emerging markets.

Some of the key mergers and acquisition include:

   • In 2016, Merck KGaA, Darmstadt, Germany completed the acquisition of Sigma-Aldrich Corporation to form MilliporeSigma and operate in the U.S. and Canada. With this acquisition, Merck has plans to serve life sciences customers worldwide with established brand such as SAFC and BioReliance.
   • In 2012, Elevance Renewable Sciences and Arkema announced a partnership to develop and produce renewable polymers. Through this partnership, both companies will work on the development of specialty bio-based polymers based on Elevance specialty methyl ester intermediate.

To summarize, focus on green chemistry has resulted in awareness regarding energy efficiency during the chemical processes. In the upcoming years, investment for developing bio-based chemicals is expected to be dependent on raw material availability, the production cost, and financial support available from the government. All these factors will play a crucial role in expanding the demand for 9-DAME in coming years.

  In-depth report on global 9-decanoic acid methyl esters market by Grand View Research:


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