The main method of preparation Chemical properties Uses Uses Production method Toxicity Hazards & Safety Information
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Sebacic acid

The main method of preparation Chemical properties Uses Uses Production method Toxicity Hazards & Safety Information
Product Name
Sebacic acid
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
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Sebacic acid Property

Melting point:
133-137 °C (lit.)
Boiling point:
294.5 °C/100 mmHg (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
pka
4.59, 5.59(at 25℃)
form 
Powder or Granules
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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.00753
Product name
Sebacic acid
Purity
for synthesis
Packaging
100 g
Price
$24.05
Updated
2021/03/22
Sigma-Aldrich
Product number
283258
Product name
Sebacic acid
Purity
99%
Packaging
5g
Price
$27.4
Updated
2021/03/22
Sigma-Aldrich
Product number
8.00753
Product name
Sebacic acid
Purity
for synthesis
Packaging
1 kg
Price
$108.22
Updated
2021/03/22
Sigma-Aldrich
Product number
283258
Product name
Sebacic acid
Purity
99%
Packaging
1kg
Price
$110
Updated
2021/03/22
Sigma-Aldrich
Product number
8.00753
Product name
Sebacic acid
Purity
for synthesis
Packaging
500 g
Price
$67.43
Updated
2021/03/22
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Sebacic acid Chemical Properties,Usage,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

Sebacic acid is widely used in the preparation of sebacic acid esters, such as dibutyl sebacate, dioctyl sebacate, diisooctyl sebacate. These esters can be used as plasticizers for plastics and cold-resistant rubber, as well as for polyamide, polyurethane, alkyd resin, synthetic lubricating oil, lubricating oil additives, spices, coatings, cosmetics, etc. It can also be used as raw material for producing nylon 1010, nylon 910, nylon 810, nylon 610, nylon 9 and high temperature resistant lubricating oil diethylhexyl ester. It is also the raw material for the production of alkyd resins (used as surface coatings, plasticized nitrocellulose coatings, and urea resin varnishes) and polyurethane rubber, cellulose resins, vinyl resins, and synthetic rubber plasticizers, softeners, and solvents.

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.

Toxicity

Sebacic acid, also known as 1, 10-decanedioic acid, belongs to aliphatic dibasic acid. Sebacic acid was present in the leaves of flue-cured tobacco, burley tobacco and aromatic tobacco. Sebacic acid was white crystal in flake form at room temperature. Slightly soluble in water, sebacic acid was insoluble in benzene, petroleum ether, carbon tetrachloride. In contrast, sebacic acid was soluble in ethanol and ethyl ether. Irritant to the eyes, respiratory system and skin irritation, sebacic acid oral harmful. However, sebacic acid was low toxic and flammable.

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.]

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Sebacic acid Suppliers

-Jiangsu Zhongzheng Biochemical Co., Ltd.
Tel
0515-84382661-
Fax
0515-84382661
Email
jszz@cnzzchem.com
Country
China
ProdList
1
Advantage
58
Jinan Hui Feng Da chemical Co., LTD.
Tel
0531-88691900- ;0531-89701765- ;0531-88691900-
Fax
0531-89702765
Email
jnhuifengda@163.com;3148353978@qq.com;3388693927@qq.com
Country
China
ProdList
526
Advantage
58
Chongqing Yuanyuanxiang Technology Development Co. LTD
Tel
023-55703781-
Fax
023-55703781
Email
2022434087@qq.com
Country
China
ProdList
4302
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
21-61259100-
Fax
86-21-61259102
Email
sh@meryer.com
Country
China
ProdList
40264
Advantage
62
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15877
Advantage
69
Chembest Research Laboratories Limited
Tel
021-20908456-
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
5948
Advantage
61
Alfa Aesar
Tel
400-610-6006; 021-67582000
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30159
Advantage
84
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386 / 800-988-0390
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24555
Advantage
81
ShangHai DEMO Chemical Co.,Ltd
Tel
400-021-7337 qq:2355568890
Fax
0086-21-50182339
Email
sales@demochem.com; export1@demochem.com
Country
China
ProdList
2582
Advantage
57
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View Lastest Price from Sebacic acid manufacturers

Hebei Crovell Biotech Co Ltd
Product
Sebacic Acid 111-20-6
Price
US $1.70/Kg/Bag
Min. Order
10g
Purity
99%
Supply Ability
10000kg
Release date
2021-07-05
Zhuozhou Wenxi import and Export Co., Ltd
Product
Sebacic Acid 111-20-6
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-11
Zhuozhou Wenxi import and Export Co., Ltd
Product
Sebacic Acid 111-20-6
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-09

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