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VibhuPRODUCT PROFILESebacic Acid: A Techno-Commercial ProfilePANKAJ [email protected] ally exports over 20,000-tons, represent- Sebacic acid is a bi-carboxylic acid ing over 90% of global trade of the prod- with structure (HOOC)(CH ) (COOH), and uct. In the industrial setting, uses of se- is naturally occurring. It was named from bacic acid and its analogs such as azelaic Parameter the Latin sebaceus (tallow candle) or acid can be found in plasticizers, lubri- sebum (tallow), in reference to its use in cants, hydraulic fluids, cosmetics, Appearance candles, etc. Sebacic acid is also used as Sebacic acid In its pure state it is a white flake or tics and painting materials.
scribed as non-hazardous, though in its Properties nition (a typical risk in handling fine or- dered crystal. It is resolved in ethanol, Packaging ether and soluble slightly in water.
Sebacic acid and its derivatives such tained from thousands of potential start- as azelaic acid have a variety of indus- ing materials. Esters are formed by re- trial uses as plasticizers, lubricants, hy- moval of water from an acid and an alco- draulic fluids, cosmetics, candles, etc. hol, e.g., carboxylic acid esters, phos- It is used in the synthesis of polyamide phoric acid esters, and sulfonic acid es- Sebacic acid is a derivative of castor and alkyd resins. It is also used as an ters. Carboxylic acid esters are used as oil, with the vast majority of world pro- intermediate for aromatics, antiseptics in a variety of direct and indirect appli- duction being done in China, which annu- and painting materials.
solvent carriers and coupling agents.
8-Octanedicarboxylic acid; decanedioic acid; 1,10-decanedioic acid; n-decanedioic acid; acide wide range of viscosity, specific gravity, va- sebacique; dicarboxylic acid C ; sebacinsaure; por pressure, boiling point, and other physi- cal and chemical properties for the proper Bis(tetrahydrofurfuryl) sebacate 4650-79-7 Di-tert-butyl bisperoxysebacate 22537-96-8 Dimethyl hexadecafluorosebacate 4590-24-3 In order of importance, two products with castor oil.
in making chemical compounds, may be substituted for sebacic acid: aze- (mostly esters and polymer resins). laic acid and adipic acid. Azelaic acid can Sebacic acid is also polymerized to be used as a substitute in HMPA (hot seed, the fruit of Ricinus communis, a make nylon 6/10, which, in turn, is fab- melt polyamide); while adipic acid could subtropical shrub, by mechanical ricated into products such as tooth- be used as a substitute for HMPA, es- pressing and/or solvent extraction.
brush bristles, fishing lines and paper ters, and nylon. In corrosion inhibitors Some castor seed is traded interna- machine felts. It also may be polymer- too alternative products not containing tionally, but most castor oil is pro- ized to produce polyester resins, coat- sebacic acid are available.
Other substitutions possible include: and Brazil. Countries producing castor produce sebacate esters. These esters are w In metal treatment: replacing sebacic oil consume a large portion of their plastics and resins) in polyvinyl chloride w In anti-freeze production: replacing siderable amount is also traded inter- sebacic acid with 2-ethyl hexanoic acid; nationally.
flexibility and freedom from cracking. Se- bacic acid is also used directly in formu- ants, as corrosion inhibitors in cutting Manufacture In theory, sebacic acid can be pro- fatty acids. Castor oil contains approxi- formulated products such as coatings, duced in a number of ways including mately 89.5% ricinoleic acid, along with from petrochemical feedstocks but lesser amounts of dihydroxystearic acid, palmitic acid, stearic acid, oleic acid, li- cic acid to precipitate from the solution. acid. The process consists of three noleic acid, linolenic acid, eicosanoic It is then filtered, water washed, and fi- steps.
1. Adipic acid is partially esterified to the noleic acid in castor oil. One of the manu- have been described, and include the use 2. Electrolysis of the potassium salt of facturing process challenges is how to of white mineral oil having a boiling range deal with the other fatty acids and con- of 300-400°C or the use of a mixture of stituents contained in castor oil without cresols. These materials act to reduce losing their intrinsic value as potential the reaction mixtures viscosity, thus 3. The last step is the hydrolysis of dime- There were two recognized produc- salts, lead oxide, and salts.
caustic fusion process and an integrated, Indian Institute of Chemical Technol- From butadiene continuous process reportedly used by ogy (IICT, Hyderabad) has developed an several of the larger Chinese producers. efficient laboratory process for the sebacic acid involves a four-step process.
preparation of sebacic acid from castor First, butadiene is oxycarbonylated to me- The castor oil or ricinoleic acid and oil in excellent yields and purity.
ized, using a palladium catalyst, to give a Monel or nickel) at a temperature of 180- In this process castor oil is split to triply unsaturated dimethyl sebacate inter- 270°C where the ricinoleic acid under- produce fatty acids, which are subjected mediate. This unsaturated intermediate is goes a series of reactions with evolution to alkali fusion. The products are neu- hydrogenated to dimethyl sebacate, which of hydrogen to give disodium sebacate tralized to separate 2-octanol and other can be hydrolyzed to sebacic acid.
further acidification, which is separated When the reaction is complete, the and purified. Processing is simpler and mers are removed through solvent crys- soaps are dissolved in water and acidi- cost effective.The process-upscaling tallizations, giving sebacic acid purities fied to a pH of about 6. At this pH, the work by batch and continuous process- of greater than 98%.
soaps of the monobasic acids (C-16 to ing modes is in progress with partial fund- C-20 plus dimer acids) are converted to ing from TIFAC (DST).
free acids that are insoluble in water. The disodium sebacate is only partially neu- Electrooxidation process An electrooxidation process was de- disodiooctadiene. Carbonation of the water soluble. The oil and aqueous lay- veloped by Asahi Chemical Industry in mixture using dry ice gives the unsatur- ers are separated. The aqueous layer Japan, and was also piloted by BASF in ated acids, 3,7-decadienedioic acid, 2- containing the half salt is acidulated to a Germany. It produces high purity seba- vinyl-5-octenoic acid, and 2,5- pH of about 2 causing the resulting seba- cic acid from readily available adipic divinyladipic acid in a ratio of about 2,5-diethyl-adipic. Sebacic acid is sepa- rated by fractional crystallization in about Source: Vikram Ricinol Derivatives Ltd.
Vikram Ricinol Derivatives Ltd. 2-octanol and glycerine with a capac- merly known as Jayant Vegoils & Chemi- (VRDL) claims to be the only manufac- ity of 2,000-tpa. Products are available cals P. Ltd.) is a fully integrated producer turer of sebacic acid in India. The com- for marketing in India and abroad (ex- of castor oil and its derivative pany has established a manufacturing cept West Europe & North America).
Imports & exports of azelaic acid, sebacic acid and their salts & esters [Quantity in tons; value in Rs. Million] Countrywise imports of azelaic acid, sebacic acid and their salts & w Manufacture of Nylon 6,10 & Nylon 11 isooctyl, benzyl and methyl sebacate.
w Lubricating oils and hydraulic fluid.
any industrial significance. Nylon 11 too is Countrywise exports of azelaic acid, sebacic acid and their salts & [Quantity in tons; value in Rs. Million] ture of number of sebacates like dioctyl used as plasticizers. Sebacate plasticizers are primarily used because of their supe- sebacate and dibutyl sebacate are used as part plasticizers to resist migration and to Imports & exports of sebacic acid, salts & esters from China [Quantity in tons; value in thousand US$] of Wayne, NJ, was the sole U.S. producer iary of International Paper. Arizona Chemi- cals ceased production of sebacic acid in bacic acid from inventory through 2003. The cilities, or other resources in place for the production, sale, or marketing of sebacic acid, though it does continue to import se- bacic acid. Caschem Inc., a subsidiary of increase sulphur staining. It is used as sta- Trade in India bilizers for PVC products requiring low tem- India has been importing as well as ing and producing sebacic acid with a pro- perature properties. Some producers of exporting small quantities of sebacic acid. prietary manufacturing process and a dedi- w Krishna Anti-oxidants P. Ltd. (Mumbai) Global scenario China is a major supplier of sebacic acid in the world having a share of about 60% of and 2-octanol at higher purities than prod- the global market. The total global market ucts on the market. The US sebacic acid The estimated demand for sebacic is estimated to be in the region of 65,000 industry changed significantly in Decem- acid for sebacate plasticizers is around tons. Most imports of sebacic acid into In- ber 2002 with the exit of two players, dia are also from China. According to data Caschem and Arizona Chemical, and the available with customs, imports of seba- entrance of a newcomer, Genesis Chemi- cic acid in the period January 1, 2005 to cal Inc., which began producing sebacic Sebacic acid is also used in the manu- May 31, 2007 (29 months) were about 442- acid at its Loveland, Ohio plant. The two facture of saturated/unsaturated polyester tons, almost all of which came from China. companies both opted to leave the market resin. It is also used in the manufacture of Prices of imported material have hovered late-2001 under pressure from low-priced alkyd resins. There are a number of substi- around Rs. 110-120 over this period.
tutes for sebacic acid for synthetic resin manufacture and its use level in the syn- thetic resins industry is negligible.
w Hengshui Dongfeng Chemical Co.Ltd.
sole US producer of sebacic acid, but the company ceased production of sebacic acid Sebacic acid is used as additives for low w Jiheng Chemical in 2004, again owing to pressure from cheap temperature lubricants at high altitudes. They w Kong Associates Chinese supplies. Sebacic acid is one of the are used as additive in lubricants for aircrafts w Qingdao Great Chemical Inc.
strategic materials stored in the National engines and also as additives in hydraulic w Shandong Haihua Tianhe Organic Chemi- Defense Stockpile maintained by the U.S.
fluids. The use of sebacic acid in lubricants is confined to aircrafts for use at high alti- w Shandong Weifang Import And Export would be needed to supply the military, in- tude levels. Synthetic lubricating oils are dustrial, and essential civilian needs of the generally used instead of Sebacic acid.The w Shanghai AiLiJiu Import And Export Co., United States during a national emergency present Indian demand for sebacic acid is and are not found or produced in the United estimated to be around 3,500-tons per an- w Shijiazhuang Summit Chemcial Co., Ltd. States in sufficient quantities to meet such num, with a modest growth rate of 6-7 per w Tonliao Xinghe Chemical Co., Ltd need. The proposed stockpile of sebacic w Wuhan Xinda E&T Dev. Co., Ltd.
acid for fiscal year 2005 is 600,000 lbs.
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