Basic information The main method of preparation Chemical properties Uses Production method Hazards & Safety Information Safety Related Supplier
ChemicalBook >  Product Catalog >  Organic Chemistry >  Carboxylic acids and derivatives >  Acyclic carboxylic acid >  Sebacic acid

Sebacic acid

Basic information The main method of preparation Chemical properties Uses Production method Hazards & Safety Information Safety Related Supplier
Sebacic acid Basic information
Sebacic acid Chemical Properties
  • Melting point:133-137 °C(lit.)
  • Boiling point:294.5 °C100 mm Hg(lit.)
  • Density 1.21
  • vapor pressure 1 mm Hg ( 183 °C)
  • refractive index 1.422
  • Flash point:220 °C
  • storage temp. Store below +30°C.
  • solubility ethanol: 100 mg/mL
  • form Powder or Granules
  • pka4.59, 5.59(at 25℃)
  • color White to off-white
  • Water Solubility 1 g/L (20 ºC)
  • Merck 14,8415
  • BRN 1210591
  • Stability:Stable. Combustible. Incompatible with strong oxidizing agents, bases, reducing agents.
  • InChIKeyCXMXRPHRNRROMY-UHFFFAOYSA-N
  • CAS DataBase Reference111-20-6(CAS DataBase Reference)
  • NIST Chemistry ReferenceDecanedioic acid(111-20-6)
  • EPA Substance Registry SystemDecanedioic acid(111-20-6)
Safety Information
  • Hazard Codes Xi
  • Risk Statements 36/37/38
  • Safety Statements 26-36-24/25
  • WGK Germany 1
  • RTECS VS0875000
  • TSCA Yes
  • HS Code 29171310
  • ToxicityLD50 orally in Rabbit: 3400 - 14500 mg/kg LD50 dermal Rat > 2000 mg/kg
MSDS
Sebacic acid Usage And Synthesis
  • The main method of preparation(1) Castor oil is as raw material, ricinoleate is separated from castor oil, with the condition of inflating and 280~300℃, caustic soda proceeds alkali fusion and the reaction is heated for 10h, sebum acid sodium salt can obtain, deputy product is 2-octanol. The sodium salt is dissolved in water, adding sulfuric acid to neutralize, after bleaching, the solution is cooled to precipitate sebum acid, it is washed with cold water, and finally recrystallized.
    CH3 (CH2) 5CH (OH) CH2CH = CH (CH2) 7COOH +
    2NaOH → CH3 (CH2) 5CH (OH) CH3 + NaOOC (CH2) 8COONa + H2
    NaOOC (CH2) 3COONa + H2SO4 → HOOC (CH2) 8COOH + Na2SO4
    (2) Adipic acid (hexane diacid) is as raw material to synthesize. Adipic acid and methanol can proceed esterification reaction to form dimethyl adipate, ion exchange membrane proceeds electrolytic oxidation to get dimer, i.e., dimethyl sebacate, and then reacts with sodium hydroxide to form the disodium salt, hydrochloric acid (or sulfuric acid) is used to neutralize and Sebacic acid can obtain.
    Chemical properties, uses and methods of preparation of sebacic acid are edited by Chemicalbook andy.(2016-12-04)
  • Chemical propertiesIt is white flaky crystal. It is slightly soluble in water, soluble in alcohol and ether.
  • Uses1. Sebacic acid can be used as cold plasticizer, nylon resins and other raw material.
    2. It can be used as analytical reagents, etc.
    3. Sebacic acid is mainly used as sebate plasticizer and nylon molding resin raw material, it is also used for high-temperature lubricant raw material. Its main product is methyl ester, isopropyl, butyl, octyl, nonyl phenyl ester and methyl ester, common ester is dibutyl sebacate and dioctyl sebacate. Sebacic acid plasticizers can be widely used in polyvinyl chloride, alkyd resins, polyester resins and polyamide molding resin due to its low toxicity and high temperature performance, so it is often used in the resin of some special purposes. Nylon molding resin which producted by sebacic acid has high toughness and low moisture absorption, it can also be processed into many special-purpose products. Sebacic acid is also rubber softener, surfactant, coating and fragrance raw materials.
    4. Sebacic acid is used as GC Less tail agent, separation and analysis of fatty acids, it can be used to precipitate and quantitative determination of thorium, separation of thorium, cerium and other rare earth elements. Plasticizers, synthetic resins and synthetic fibers.
  • Production methodIt can be obtained by raw materials of natural castor oil or adipic acid monoester. Sebacic acid can be obtained by polymerization reaction with ethylene and carbon tetrachloride, but the world's industrial production of sebacic acid almost all use castor oil as raw material.
    1. castor oil cracking process: under effect of alkali, castor oil is heated to proceed hydrolysis and generates sodium castor oil soap, then sulfuric acid is added to acidolysis and ricinoleic acid is obtained; in the presence of diluent cresol , alkali is added and it is heated to 260-280℃ to proceed splitting decomposition and generates sebacic acid and sodium bis octanol and hydrogen, lysate is diluted with water, heated and adding acid to neutralize, double salt is turned into monosodium salt; and then neutralized liquid after actived carbon decoloration is boiling and added acid, sebacic acid monosodium salt turns into sebacic acid and seeds out, after separation, drying can derive products. Material consumption fixed: castor oil (industrial) 2100kg/t, sulfuric acid (98%) 1600kg/t, caustic soda (95%) 1200kg/t, cresol (industrial) 100kg/t. 2.Oil n-decane fermentation method: n-decane is obtained by the separation of 200 # solvent oil or 166-182℃ fraction, sebacic acid is obtained by 19-2 Solutions Candida lipolytica fermentation.
    2. New cyclopentanone method: palladium salt-copper or iron is as catalyst, in the solvent of ethanol, propanol or other alcohol, in the eased condition of low temperature of 40-60℃ and ordinary pressure, cyclopentene is oxidated by air to generate cyclopentanone, then it is obtained by oxidated of iron catalyst and titanium.
  • Hazards & Safety InformationCategory: Flammable liquid
    Toxicity: grading toxicity
    Acute oral toxicity-rat LD50: 14375 mg/kg; Oral-Mouse LD50: 6000 mg/kg
    Flammability hazard characteristics: flammable, the fire discharges acrid smoke
    Storage characteristics: Treasury ventilation low-temperature drying
    Extinguishing agent: Dry powder, foam, sand, water
  • DescriptionSebacic acid is a dicarboxylic acid with structure (HOOC)(CH2)8(COOH), and is naturally occurring.
    In its pure state it is a white flake or powdered crystal. The product is described as non-hazardous, though in its powdered form it can be prone to flash ignition (a typical risk in handling fine organic powders).
    Sebaceus is Latin for tallow candle, sebum (tallow) is Latin for tallow, and refers to its use in the manufacture of candles. Sebacic acid is a derivative of castor oil, with the vast majority of world production occurring in China which annually exports over 20,000 metric tonnes, representing over 90 % of global trade of the product.
    In the industrial setting, sebacic acid and its homologues such as azelaic acid can be used in plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc. Sebacic acid is also used as an intermediate for aromatics, antiseptics, and painting materials.
  • Chemical Propertieswhite powder
  • UsesDecanedioic acid was named by Thenard LJ (1802) from the Latin sebaceus(tallow candle) or sebum (tallow) in reference to its use in the manufacture of candles. Thenard LJ isolated this compound from distillation products of beef tallow. In 1954, it was reported that it was produced in excess of 10,000 tons annually by alkali fission of castor oil. Sebacic acid and its derivatives, as azelaic acid, have a variety of industrial uses as plasticizers, lubricants, diffusion pump oils, cosmetics, candles, etc. It is also used in the synthesis of polyamide, as nylon, and of alkyd resins. An isomer, isosebacic acid, has several applications in the manufacture of vinyl resin plasticizers, extrusion plastics, adhesives, ester lubricants, polyesters, polyurethane resins and synthetic rubber.
  • General DescriptionWhite granular powder. Melting point 153°F. Slightly soluble in water. Sublimes slowly at 750 mm Hg when heated to melting point.
  • Air & Water ReactionsInsoluble in water.
  • Reactivity ProfileSebacic acid reacts exothermically to neutralize bases, both organic and inorganic. May react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Can react with active metals to form gaseous hydrogen and a metal salt. Such reactions are slow in the dry, but systems may absorb enough water from the air to allow corrosion of iron, steel, and aluminum parts and containers. Reacts slowly with cyanide salts to generate gaseous hydrogen cyanide. Reacts with solutions of cyanides to cause the release of gaseous hydrogen cyanide. May generate flammable and/or toxic gases and heat with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. May react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Can be oxidized exothermically by strong oxidizing agents and reduced by strong reducing agents. May initiate polymerization reactions.
  • Fire HazardFlash point data for Sebacic acid are not available. Sebacic acid is probably combustible.
  • Purification MethodsPurify sebacic acid via the disodium salt which, after crystallisation from boiling water (charcoal), is again converted to the free acid. The free acid is crystallised repeatedly from hot distilled water or from Me2CO/pet ether and dried under vacuum. [Beilstein 2 IV 2078.]
Sebacic acid Preparation Products And Raw materials
Sebacic acid(111-20-6)Related Product Information
Sebacic acidSupplierMore
  • Company Name:J & K SCIENTIFIC LTD.
  • Tel:400-666-7788 +86-10-82848833
  • Email:jkinfo@jkchemical.com;market6@jkchemical.com
  • Products Intro:Product Name:Sebacic acid, 98%
    CAS:111-20-6
    Purity:98% Package:1KG;250G
  •  
  • Company Name:Meryer (Shanghai) Chemical Technology Co., Ltd.
  • Tel:+86-(0)21-61259100(Shanghai) +86-(0)755-86170099(ShenZhen) +86-(0)10-62670440(Beijing)
  • Email:sh@meryer.com
  • Products Intro:Product Name:Sebacic Acid
    CAS:111-20-6
    Purity:>98.0%(GC)(T) Package:25g;500g Remarks:S0022
  •  
  • Company Name:3B Pharmachem (Wuhan) International Co.,Ltd.
  • Tel:86-21-50328103 * 801、802、803、804 Mobile:18930552037
  • Email:3bsc@sina.com
  • Products Intro:Product Name:Sebacic acid
    CAS:111-20-6
    Purity:99% HPLC Package:1Mg ; 5Mg;10Mg ;100Mg;250Mg ;500Mg ;1g;2.5g ;5g ;10g
  •  
  • Company Name:Chembest Research Laboratories Limited
  • Tel:+86(0)21-20908456
  • Email:sales@biochembest.com; market@biochembest.com
  • Products Intro:Product Name:Decanedioic acid
    CAS:111-20-6
    Remarks:C10610
  •  
  • Company Name:Alfa Aesar
  • Tel:400-610-6006; 021-67582000
  • Email:saleschina@alfa-asia.com
  • Products Intro:Product Name:Sebacic acid, 98+%
    CAS:111-20-6
    Package:100g Remarks:A14158
  •