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SYNTHESIS OF INDIGO DYE
Indigo, or indigotin, is a dyestuff originally extracted from the varieties of the indigo and woad plants. Indigo was known throughout the ancient world for its ability to color fabrics a deep blue. Egyptian artifacts suggest that indigo was employed as early as 1600 B.C. and it has been found in Africa, India, Indonesia, and China. The dye imparts a brilliant blue hue to fabric. In the dying process, cotton and linen threads are usually soaked and dried 15-20 times. By comparison, silk threads must be died over 40 times. After dying, the yarn may be sun dried to deepen the color. Indigo is unique in its ability to impart surface color while only partially penetrating fibers. When yarn died with indigo is untwisted, it can be seen that the inner layers remain uncolored. The dye also fades to give a characteristic wom look and for this reason it is commonly used to color denim. Originally extracted from plants, today indigo is synthetically produced on an industrial scale. It is most commonly sold as either a 100% powder or as a 20% solution. Through the early 1990s, indigo prices ranged near $44/lb ($20/kg).
The name indigo comes from the Roman term indicum, which means a product of India. This is somewhat of a misnomer since the plant is grown in many areas of the world, including Asia, Java, Japan, and Central America. Another ancient term for the dye is nil from which the Arabic term for blue, al-nil, is derived. The English word aniline comes from the same source. The dye can be extracted from several plants, but historically the indigo plant was the most commonly used because it is was more widely available. It belongs to the legume family and over three hundred species have been identified. Indigo tinctoria and I. suifruticosa are the most common. In ancient times, indigo was a precious commodity because plant leaves contain only about small amount of the dye (about 2-4%). Therefore, a large number of plants are required to produce a significant quantity of dye. Indigo plantations were founded in many parts of the world to ensure a controlled supply. Demand for indigo dramatically increased during the industrial revolution, in part due to the popularity of Levi Strauss's blue denim jeans. The natural extraction process was expensive and could not produce the mass quantities required for the burgeoning garment industry. So chemists began searching for synthetic methods of producing the dye. In 1883 Adolf von Baeyer (of Baeyer aspirin fame) researched indigo's chemical structure. He found that he could treat omega-bromoacetanilide with an alkali (a substance that is high in pH) to produce oxindole. Later, based on this observation, K. Heumann identified a synthesis pathway to produce indigo. Within 14 years their work resulted in the first commercial production of the synthetic dye. In 1905 Baeyer was awarded the Nobel Prize for his discovery. At the end of the 1990s, the German based company BASF AG was the world's leading producer, accounting for nearly 50% of all indigo dyestuffs sold. In recent years, the synthetic Prepared By: Muhammad Furqan
The chemical found in plant leaves is really indican. Only the leaves are used since they contain the greatest concentration of dye molecules. This allows the air to oxidize the indoxyl to indigotin. New. woad. An enzyme known as indimulsin is added to hydrolyze. RAW MATERIALS The raw materials used in the natural production of indigo are leaves from a variety of plant species including indigo. The mixture is allowed to ferment for about one week to form the dye pigment which is called sukumo. lye ash. Polygonum Indigo Fera Indigo Plant Woad THE MANUFACTURING PROCESS NATURAL EXTRACTION Plant extraction of indigo requires several steps because the dye itself does not actually exist in nature. After about 14 hours. The upper layer of liquid is siphoned away and the settled pigment is transferred to a third tank where it is heated to stop the fermentation process. a series of tanks are arranged in a step wise fashion. During this process carbon dioxide is given off and the broth in the tank turns a murky yellow.Synthesis Of Indigo Dye process used to produce indigo has come under scrutiny because of the harsh chemicals involved. In this process the plant is mixed with wheat husk powder. a precursor to indigo. the resulting liquid is drained into a second tank. more environmentally responsible methods are being sought by manufacturers. the indican into indoxyl and glucose. the Japanese have used another method which involves extracting indigo from the polygonum plant. The upper-most tank is a fermentation vessel into which the freshly cut plants are placed. Historically. the indoxyl-rich mixture is stirred with paddles to mix it with air. Here. and polygonum. In this process. and sake. limestone powder. The resultant mixture is filtered to remove impurities and dried to form a thick paste. which settles to the bottom of the tank. In the synthetic process. a number of chemicals are employed as described below. Prepared By: Muhammad Furqan . or break down. The ancient process to extract indican from plant leaves and convert it to indigo has remained unchanged for thousands of years.
A number of other chemical byproducts are also produced in this reaction. a few methods invented by the Germans for continuous process manufacturing. All these processes involve combining a series of chemical reactants under controlled conditions. However. the amount of dye yielded by this process is very low. Another. Prepared By: Muhammad Furqan . a method which uses sodamide with alkali to convert phenylglycine to indoxyl. thus lowering the overall reaction temperature from almost 570°F (300°C) to 392°F (200°C). In this method. formaldehyde.Synthesis Of Indigo Dye SYNTHETIC PRODUCTION A variety of synthetic chemical processes have been used to produce indigo. These synthesis reactions are conducted in large stainless steel or glass reaction vessels. which can be converted to indigotin by contact with air. Heumann's original synthesis of indigo Pfleger's synthesis of indigo FINISHING OPERATIONS After the chemical reaction process is complete. Currently. There are. for over 30 years. the finished dye must be washed to remove impurities and then dried. however. This process was popular with major manufacturers. A variation of this method (which has become widely used) involves the reaction of aniline. such as BASF and Hoechst. more efficient. TYPES OF REACTIONS The first commercial method of producing indigo was based on Heumann's work. This results in a much more efficient reaction process. These vessels are equipped with jackets to allow steam or cold water to flow around the batch as the reactions progress. the dye is usually made in batch quantities. and hydrogen cyanide to form phenylglycinonitrile. N-phenylglycine is treated with alkali to produce indoxyl. This material is then hydrolyzed to yield phenylglycine which is then converted to indigotin. The reactants undergo a series of reactions which result in the formation of the indigo molecule. Sodamide reacts with excess water. Because of the complexity of these chemical processes. The dried powder can be packed in drums or reconstituted with water to form a 20% solution and filled in pails. synthesis route utilizes anthranilic acid.
These waste chemicals can enter the environment in at least three different ways. and the reaction time (which determines the degree of completion). If any of these variables deviate from specifications. the resulting reaction product can be affected. of Rochester New York. One promising future method involves using biocatalysts in the dye reaction process. QUALITY CONTROL During indigo manufacture. and the third is when the dye is eluted into the wash water during the initial stonewashing or wet processing of the fabric. there are other reaction side products that are produced along with the indigo. According Prepared By: Muhammad Furqan ." BYPRODUCTS/WASTE Indigo production produces a variety of waste products which must be handled carefully. THE FUTURE Much of the need for indigo is being met with other types of blue dyes and today most of the indigo used by the world is made out-side the United States. The second is when the dye is applied to the yarn. is evaluating a process to produce indigo using biotechnology. To ensure that manufacturers can consistently purchase the same shade of dye. Genencor International. Some of these materials are considered to be hazardous and must be disposed of in accordance with local and federal chemical waste disposal guidelines. poor quality control results in lower yield of the dye. Typically. This last route typically occurs during the production of denim fabric. It is designated as "CI Natural Blue CI 75780. Researchers are concentrating on new methods of indigo manufacture that are more environmentally friendly. The first is during the actual manufacture of the molecule. Indigo dye may be one of the first high-volume chemicals made through a biological route.Synthesis Of Indigo Dye The chemical symbol for indican. In addition to the reactants described above. the reaction process is continuously monitored to ensure the chemicals are combined in the proper ratios. Key elements that must be controlled include the pH (or acid/base quality of the batch). indigo is assigned a Color Index number that defines its shade. which increases costs for the manufacturer. the compound found in the leaves of the indigo plant that is used to make indigo dye. the temperature (which controls the speed of the reaction).
pumice stone handling and storage costs are reduced. this new process not only reduces garment damage. pumice stones which help give the fabric its faded look." which allows indigo dye in the fabric to break down 50% faster in the stonewash cycle. Genencor is seeking a major market partner to work with them in the development of this new technology. along with time required to separate pumice from garments after stonewashing. but also reduces waste produced by the stones and bleach. at this time the technology is expensive and production costs could be prohibitive. Therefore. BIBLIOGRAPHY http://www. Burlington's Denim Division introduced a technology in 1994 they call "Stone Free.Synthesis Of Indigo Dye to Charles T. However. if any. It also uses much less bleach. Manufacturers who use indigo in dying operations are also seeking to improve their use of the dye. indigo produced by this method is chemically the same as the regular synthetic dye and behaves identically in dyeing tests. For example. Goodhue.madehow. Genencor's Program Director/Biocatalysis Research and Development. Therefore. Compared to traditional methods of stonewashing fabric dyed with indigo.html Prepared By: Muhammad Furqan .com/Volume-6/Indigo. their new process uses few.
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