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Sebacic Acid

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Sebacic Acid is a white flake or powdered crystal. It is resolved in ethanol, ether and soluble slightly in water. Sebacic Acid was named from the Latin sebaceus (tallow candle) or sebum (tallow) in reference to its use in the manufacture of candles. Sebacic Acid and its derivatives such as azelaic acid have a variety of industrial uses as plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc. It is used in the synthesis of polyamide and alkyd resins. It is also used as an intermediate for aromatics, antiseptics and painting materials.

Sebacic acid is a dicarboxylic acid and is a derivative of castor oil.

Chemical, Physical Properties & Specifications of Sebacic Acid

 

Chemical Names

Decanedioic acid

1,8-Octanedicarboxylic Acid

Dicarboxylic acid C10

Chemical Formula

C10H18O4

CAS#

111-20-6

Physical State and Appearance

White flake or powdered crystal in its pure state

Molecular weight

202.24 g/mole

Color

Colorless to light yellow

Odour

Mild odor of fatty acid

Boiling Point

Decomposes

Melting Point

132°C (269.6°F)

Specific Gravity

1.207 (Water = 1)

Density at 25 deg0 C

1.209 g per cubic centimeter

Dispersion Properties

See solubility in water, methanol, diethyl ether, acetone

 

Sebacic Acid Production

There are two primary methods: the traditional method uses castor oil as the starting point while a new method uses adipic acid as the starting point

Sebacic Acid from Castor Oil

Sebacic acid can be synthesized from phenols and cresols, but castor oil oxidation is considered a ―greener‖ process.

Sebacic acid is manufactured by heating castor oil to high temperatures (about 250oC) with alkali. This treatment results in saponification of the castor oil to ricinoleic acid that is then cleaved to give capryl alcohol (2-octanol) and sebacic acid. Although the sebacic acid yields are low, this route has been found to be cost competitive.

Ricinoleic Acid  Alkali Fusion @ 250 deg C  2-Octanol CH3(CH2)5CH(OH)CH3+ Sebacic Acid COOH(CH2)8COOH+ H2

The process is based on the caustic oxidation of castor oil. The type of reaction used affects the purity of the sebacic acid; the modern conversion technology results in a higher purity (There is an older domestic conversion which uses a mixture of molten caustic soda and caustic potash). The modern method, which also claims higher yields, uses castor oil and molten caustic. The type of reaction used affects the purity of the sebacic acid, and the modern conversion technology is reported to yield sebacic acid with a higher purity.

Pyrolysis of ricinoleic acid results in heptaldehyde and undecenoic acid. Alkali fusion of this mixture results in 10-hydroxydecanoic acid.

With 10-hydroxydecanoic acid, an increase to two moles of alkali/mole ricinoleate and at temperatures of 250 to 275oC produces capryl alcohol (also called 2-Octanol - C8H18O) and sebacic acid.

In the actual reaction, the castor oil and caustic are fed to a reactor at a temperature of 180 to 270 oC where the ricinoleic acid undergoes a series of reactions with evolution of hydrogen to give disodium sebacate and capryl alcohol.

When the reaction is complete, the soaps are dissolved in water and acidified to a pH of about 6.

At this pH, the soaps are converted to free acids that are insoluble in water. The disodium sebacate is then partialy neutralized to the half acid salt which is water soluble. The oil and aqueous layers are separated. The aqueous layer containing the half salt is acidulated to a pH of about 2, causing the resulting sebacic acid to precipitate from the solution.

It is then filtered, water washed, and finaly dried.

A number of process improvements have been described, which include the use of white mineral oil having a boiling range of 300 to 400 oC or the use of a mixture of cresols. These materials act to reduce the reaction mixture's viscosity, thus improving mixing. Higher sebacic acid yields are claimed by the use of catalysts such as barium salts, cadmium salts, lead oxide, and salts.

Production of Sebacic Acid from Adipic Acid

An electro oxidation process was developed by Asahi Chemical Industry in Japan and was also piloted by BASF in Germany. It produces high purity sebacic acid from adipic acid.

The process consists of three steps

1. Adipic acid is partially esterfied to the monomethyl adipate

2. Electrolysis of the potassium salt of monomethyl adipate in a mixture of methanol and water gives dimethyl sebacate

3. The last step is the hydrolysis of dimethyl sebacate to sebacic acid

Overall yields are reported to be about 85%.

Demand - Supply Estimates for Sebacic Acid

According to the industry nomenclature, generation I derivatives include hydrogenated castor oil, 12-hydroxy stearic acid, dehydrated castor oil acid, and ethoxylated castor oil among others. Generation II castor oil derivatives include sebacic acid, undecyclenic acid, heptaldehyde, polyols and dimer acid. Generation III derivatives include the esters and salts of generation II derivatives as well as derivatives such as methyl-12-hydroxystearate.

The global market for generation II castor oil derivatives is estimated at $300 million (based on 2007 data). For generation III derivatives, where half of the generation II derivatives are converted, the estimated market worth is close to $350 million (based on 2007 data).

Overall, the castor oil and derivatives industry have shown an average demand growth of about 4% per annum for the period 2000-2007.

Current Demand-Supply Estimates for Sebacic Acid

Global Demand

Global demand level: Approximately 140,000 metric tonnes per annum

Global supply

Global installed capacity: Approximately 150,000 metric tonnes per annum

China is currently the primary producer of SBA. The United States and India are also producers.

Hengshui Dongfeng and Hengshui Jinghua Chemical Plant, China’s largest Sebacic acid producers manufacture 23000 tons and 30000 tons per year respectively. Sebacic Acid India, India’s largest supplier produces 10000 T/yr.

Amount of castor oil used for sebacic acid

We have not been able to determine this yet

Price of Sebacic Acid

FOB Price (Tianjin, China) – Sep 2009

$3,584.00/MT - $3,602.00/MT CIF Mumbai (Origin port: Tianjin, China)

$3,648.00/MT - $3,666.00/MT Palletized CIF price: $3,686.00/MT - $3,704.00/MT

Note: All data for Sep 2009

Historical price data

We were not able to get continuous data for sebacic acid from 2000. However, we have been able to get some discrete sets of data

Period / Month

Price ($/T)

Sep 2009

3600

Dec 2004

4625

Jul 2002

4175

2001-02

5600

 

Sebacic Acid Applications

·         Sebacic Acid was named from the Latin sebaceus (tallow candle) or sebum (tallow) in reference to its use in the manufacture of candles

·         One of the largest uses of Sebacic Acid is in the manufacture of Nylon 6-10. Sebacic acid and hexamethylene diisocyanate react through condensation polymerization to produce Nylon 6-10.

·         Sebacic Acid and its derivatives such as Azelaic acid have a variety of industrial uses in plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc. They are used in the synthesis of polyamide and alkyd resins. An isomer, isosebacic acid, has other applications in the manufacture of extrusion plastics, adhesives, polyesters, polyurethane resins and synthetic rubber.

·         Sebacic Acid is also used as an intermediate for aromatics, antiseptics and painting materials. A large number of esters can be obtained from thousands of potential starting materials.

·         It is used as a corrosion inhibitor in metalworking fluids and as a complexing agent in greases. When mixed with amines, Sebacic acid can give a very effective water soluble corrosion inhibitor for metal working fluids.

·         Lithium hydroxystearate complex greases often utilize dibasic acids such as sebacic acid for the more unusual performance parameters. These greases require the esters of sebacic acid, which were developed for specific performance criteria under varying conditions. Examples: DOS (dioctyl sebacate) is very functional in low temperature formulations and DSS (disodium sebacate) has been used to replace sodium nitrites in aluminum greases. Its fine particle size allows it to be added to the grease during the cool down period with no additional processing. DMS/DBS (dimethyl sebacate/dibutyl sebacate) are synthetic base stocks that can replace the mineral oils for environmentally friendly applications. DOS or DMS in complexed greases improve workability and low temperature properties particularity for applications in aircraft, trucks, automobiles and equipment exposed to arctic conditions.

·         The esters of sebacic acid also are used as plasticizers for vinyl resins and in the manufacture of dioctyl sebacate - a jet lubricant and lubricant in aircooled combustion motors.

Two derivatives of sebacic acid are used in a range of applications as well.

Dibutyl Sebacate (DBS) - Di-n-bibutyl Sebacate (DBS), is transparent oil liquid, dissolves ethanol and ether. This product is widely used as rocket propellant. Being non-toxic, used in food & pharma industry as packing material It is also used as cold resistant plasticizer for synthetic resin and synthetic rubber.

Dioctyl Sebacate (DOS) - Dioctyl Sebacate (DMS) a transparent light yellow oil liquid with a distinct smell This product with low volatility and high-resistant, lightproof, and electrical insulation dissolve in hydracarbons, alcohol, ether, benzene and other organic solvents.

It is mainly used by PVC, chloroethylene copolymer, nitrocellulose, ethyl cellulose and synthetic rubber industries as plasticizer and suitable for cold resistant cables, leatherette, thin film, sheet material, etc.

Application Sectors for Sebacic Acid

Application Sector

Nature of Application

Nylon

Nylon 6,10

Plasticizer

Dimethyl sebacate

Dioctyl sebacate

Dibutyl sebacate

Diisopropyl sebacate

Lubricant

Heat resistance lubricant oil

Epoxy solidified agent

Sebacic anhydride

Synthetic lubricating grease

Derivatives

Azelaic acid

Isosebacic acid(Isomer)

Miscellaneous

Perfumery

Pharmaceuticals

 

Largest Users of Sebacic Acid

·         Du Pont

·         BASF

Main Countries Producing Sebacic Acid

·         China

·         Japan

·         Brazil

·         India

·         United Kingdom

Top Suppliers of Sebacic Acid Worldwide:

Name of the Manufacturer

Location

Fulida Industry co Hebei

China

Green International

Germany

Hengshui Dongfeng Chemical Co

China

Hengshui Jinghua Chemical Plant

China

Hengshui OK Enterprises Hebei Inner Mongolia Tianrun

China

Castor Development Co., Ltd

China

Jiheng Chemical

China

Mitsu Toatsu Chemicals

Japan

Persulphate Ltd

China

Qingdao Great Chemical Inc

China

Ronas Chemicals Ind. Co., Ltd.

Taiwan

Shandong Haihua Tianhe Organic Chemical Co., Ltd

China

Shandong Ocean Chemical Group

China

Shenzhen Pharmaceutical Factory

Shenzhen, Guangdong, China

Shijiazhuang Jihua, Chemical Textile Co

China

Sinochem Tianjin

Tianjin, China

Suny Chem International Co., Ltd

Yantai Shandong, China

Taizhou Donghai Chemical Co.Ltd.,

Zhejiang Province, China

Tianjin No.1 Chemical Reagent Factory

Tianjin, China

Tianjin Zhonghe Chemical Plant

Tianjin, China

Tonliao Xinghe Chemical Co., Ltd

Inner Mongolia, China

Unitchem Co Ltd

China

Weifang Tianhe Organic Chemical Co.,

China

Zouping County Tianxing Chemical Industry Co., Ltd

China