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Sebacic acid

The main method of preparation Chemical properties Uses Production method Hazards & Safety Information
Sebacic acid
Sebacic acid structure
CAS No.
111-20-6
Chemical Name:
Sebacic acid
Synonyms
sebacic;usafhc-1;USAF hc-1;Ipomic acid;SEBCIC ACID;Decanedioic;Sebacinsure;SEBACIC ACID;Sabacic acid;sebacinsaure
CBNumber:
CB0329394
Molecular Formula:
C10H18O4
Formula Weight:
202.25
MOL File:
111-20-6.mol

Sebacic acid 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
pka
4.59, 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.
InChIKey
CXMXRPHRNRROMY-UHFFFAOYSA-N
CAS DataBase Reference
111-20-6(CAS DataBase Reference)
NIST Chemistry Reference
Decanedioic acid(111-20-6)
EPA Substance Registry System
Sebacic acid (111-20-6)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36-24/25
WGK Germany  1
RTECS  VS0875000
TSCA  Yes
HS Code  29171310
Toxicity LD50 orally in Rabbit: 3400 - 14500 mg/kg LD50 dermal Rat > 2000 mg/kg

Sebacic acid price More Price(15)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 283258 Sebacic acid 99% 111-20-6 5g $25.5 2019-12-02 Buy
Sigma-Aldrich 283258 Sebacic acid 99% 111-20-6 1kg $104 2019-12-02 Buy
TCI Chemical S0022 Sebacic Acid >98.0%(GC)(T) 111-20-6 25g $14 2019-12-02 Buy
TCI Chemical S0022 Sebacic Acid >98.0%(GC)(T) 111-20-6 500g $33 2019-12-02 Buy
Alfa Aesar A14158 Sebacic acid, 98+% 111-20-6 100g $17.6 2019-12-02 Buy

Sebacic acid Chemical Properties,Uses,Production

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 properties

It is white flaky crystal. It is slightly soluble in water, soluble in alcohol and ether.

Uses

1. 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 method

It 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 Information

Category: 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

Description

Sebacic 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 Properties

white powder

Uses

Decanedioic 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 Description

White granular powder. Melting point 153°F. Slightly soluble in water. Sublimes slowly at 750 mm Hg when heated to melting point.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Sebacic 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 Hazard

Flash point data for Sebacic acid are not available. Sebacic acid is probably combustible.

Purification Methods

Purify 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

Raw materials

Preparation Products


Sebacic acid Suppliers

Global( 347)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Xiamen AmoyChem Co., Ltd
+86 592-605 1114
sales@amoychem.com CHINA 6372 58
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sale@mainchem.com CHINA 32447 55
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259
0755-23311925 Abel@chembj.com CHINA 3194 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22633 55
Shanghai Time Chemicals CO., Ltd.
+86-021-57951555
+86-021-57951555 jack.li@time-chemicals.com CHINA 1365 55
Hangzhou FandaChem Co.,Ltd.
0086 158 5814 5714 (Mobile
+86-571-56059825 fandachem@gmail.com CHINA 2928 55
Hefei TNJ Chemical Industry Co.,Ltd.
86-0551-65418684 18949823763
86-0551-65418684 info@tnjchem.com China 1878 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29996 58
Chemwill Asia Co.,Ltd.
86-21-51086038
86-21-51861608 chemwill_asia@126.com;sales@chemwill.com;chemwill@hotmail.com;chemwill@gmail.com CHINA 23981 58
Haihang Industry Co.,Ltd
86-531-88032799
+86 531 8582 1093 export@haihangchem.com CHINA 8815 58

View Lastest Price from Sebacic acid manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-07-23 Sebacic acid
111-20-6
US $7.69 / KG 1KG 99.5% 1000TON career henan chemical co

Sebacic acid Spectrum


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