SEBACINIC ACID

SEBACINIC ACID - Names and Identifiers

Name	Sebacic acid
Synonyms	SEBACIC ACID decanedioate Sebacic acid SEBACINIC ACID acidesebacique DECANEDIOIC ACID Decanedioic acid RARECHEM AL BO 0380 1,10-decanedioicacid 1,10-Decanedioic acid 1,8-Octanedicarboxylic acid 1,8-OCTANEDICARBOXYLIC ACID Octane-1,8-dicarboxylic acid
CAS	111-20-6
EINECS	203-845-5
InChI	InChI=1/C10H18O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-8H2,(H,11,12)(H,13,14)/p-2
InChIKey	CXMXRPHRNRROMY-UHFFFAOYSA-N

SEBACINIC ACID - Physico-chemical Properties

Molecular Formula	C10H18O4
Molar Mass	202.25
Density	1.21
Melting Point	133-137 °C (lit.)
Boling Point	294.5 °C/100 mmHg (lit.)
Flash Point	220 °C
Water Solubility	1 g/L (20 ºC)
Solubility	Soluble in alcohols, esters and ketones, slightly soluble in water. 1g dissolved in 700 ml of water and 60 ml of boiling water
Vapor Presure	1 mm Hg ( 183 °C)
Appearance	White crystal
Color	White to off-white
Merck	14,8415
BRN	1210591
pKa	4.59, 5.59(at 25℃)
Storage Condition	Store below +30°C.
Stability	Stable. Combustible. Incompatible with strong oxidizing agents, bases, reducing agents.
Sensitive	Easily absorbing moisture
Refractive Index	1.422
MDL	MFCD00004440
Physical and Chemical Properties	Character: white patchy crystal. melting point 134~134.4 ℃ boiling point 294.5 ℃ relative density 1.2705 refractive index 1.422 solubility slightly soluble in water, soluble in alcohol and ether.
Use	Used as raw materials for cold-resistant plasticizer, resin and nylon

SEBACINIC ACID - Risk and Safety

Hazard Symbols	Xi - Irritant
Risk Codes	36/37/38 - Irritating to eyes, respiratory system and skin.
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S24/25 - Avoid contact with skin and eyes.
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

SEBACINIC ACID - Upstream Downstream Industry

Raw Materials	Castor oil Sulfuric acid Sodium hydroxide
Downstream Products	1,10-Decanediol DMS Poly(hexamethylene sebacamide) (Nylon 6\|10) dibutyl sebacate dibutyl sebacate Dioctyl sebacate

SEBACINIC ACID - Nature

Open Data Verified Data

White Flake Crystal, flammable. The melting point was 134-134.4 °c. The boiling point is 294.5 ℃(13. 3kPa) and the relative density is 1. 2705. Refractive index 422. Molar heat of combustion 5.424 MJ/mol. Slightly soluble in water, soluble in alcohol and ether.

Last Update：2024-01-02 23:10:35

SEBACINIC ACID - Preparation Method

Open Data Verified Data

castor oil cracking method Castor oil is hydrolyzed by heating under the action of alkali to generate ricinoleic acid sodium soap, and then sulfuric acid is added to generate ricinoleic acid; In the presence of diluent cresol, alkali is added and heated to 260~280 ℃ for cracking to generate sebacic acid disodium salt, secondary octanol and hydrogen. After the lysate is diluted with water, the disodium salt becomes monosodium salt; The neutralized solution is boiled and acid is added, sebacic acid crystallized and precipitated to obtain the finished product.
petroleum n-decane fermentation sebacic acid was obtained by fermenting 19-2 Candida Lipolysis Using N-decane isolated from 200# solvent naphtha or a fraction of 166-182 °c.
The new cyclopentanone method uses Palladium Salt-copper or iron as the catalyst, in ethanol, propanol or other alcohol solvent, under mild conditions of low temperature and normal pressure of 40~60 C, cyclopentene is oxidized with air to form cyclopentanone, followed by oxidation and dimerization with an iron catalyst.

Last Update：2022-01-01 10:31:55

SEBACINIC ACID - Introduction

Gas chromatography tailing agent, separation and analysis of fatty acids, can be used for precipitation and quantitative determination of thorium, and thorium and cerium and other rare earth elements to separate.

Last Update：2022-10-16 17:12:03

SEBACINIC ACID - Use

Open Data Verified Data

It is mainly used as a raw material for sebacate plasticizer and nylon molding resin, and can also be used as a raw material for high temperature resistant lubricating oil. Its main ester products are methyl ester, isopropyl Ester, butyl ester, octyl Ester, nonyl ester and benzyl ester, commonly used esters are dibutyl sebacate and sebacic acid dioctyl grains. Decyl Diester plasticizer can be widely used in polyvinyl chloride, alkyd resin, polyester resin and polyamide molding resin, because of its low toxicity and high temperature resistance, it is often used in some special purpose resin. The nylon molding resin produced from sebacic acid has high toughness and low moisture absorption, and can also be processed into many special purpose products. Sebacic acid is also a raw material for rubber softeners, surfactants, coatings and fragrances.

Last Update：2022-01-01 10:31:54

SEBACINIC ACID - Safety

Open Data Verified Data

sebacic acid is essentially non-toxic, but the cresol used in the production is toxic and should be protected from poisoning (see cresol). Production equipment should be closed. Operators should wear masks and gloves. Packed in woven or hemp bags lined with plastic bags, each bag has a net weight of 25kg, 40kg, 4SKG or 50kg. Store in a cool and ventilated place, fire and moisture. Do not mix with liquid acid and alkali. According to the provisions of flammable storage and transportation.

Last Update：2022-01-01 10:31:55

SEBACINIC ACID - Reference Information

LogP	1.5 at 23℃
NIST chemical information	Information provided by: webbook.nist.gov (external link)
EPA chemical information	Information provided by: ofmpub.epa.gov (external link)
main preparation method	(1) castor oil is used as raw material, ricinoleic acid is separated from castor oil, and caustic soda is subjected to alkali melting under pressure and 280~300 ℃, and heated for 10h to prepare sodium salt of sebum acid, and 2-octanol is by-product. Dissolve the sodium salt in water, add sulfuric acid to neutralize, decolorize, cool the solution, precipitate sebum acid, wash with cold water, and finally recrystallize. 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) is synthesized from fatty acid (adipic acid). Adipic acid and methanol undergo esterification reaction to form dimethyl adipate, which is electrolytically oxidized by ion exchange membrane to form dimer, namely dimethyl sebacate, which reacts with sodium hydroxide to form disodium salt, and then neutralizes with hydrochloric acid (or sulfuric acid) to obtain sebum acid.
use	used as raw material for cold-resistant plasticizer, resin, nylon, etc. used as analytical reagent, etc. mainly used as raw material for sebacate plasticizer and nylon molding resin, and also used as raw material for high temperature resistant lubricating oil. Its main ester products are methyl ester, isopropyl ester, butyl ester, octyl ester, nonyl ester and methyl benzene. Commonly used esters are dibutyl sebacate and dioctyl sebacate. Sebacic acid plasticizer can be widely used in polyvinyl chloride, alkyd resin, polyester resin and polyamide molding resin. Because of its low toxicity and high temperature resistance, it is often used in some special purpose resins. The nylon molding resin produced with sebacic acid has high toughness and low moisture absorption, and can also be processed into many special-purpose products. Sebacic acid is also a rubber softener, surfactant, paint and perfume raw material. gas chromatography tailing agent, separation and analysis of fatty acids, can be used for precipitation and quantitative determination of thorium, and thorium and cerium and other rare earth element cable separation. Plasticizers, synthetic resins and synthetic fibers. Used for separation and analysis of fatty acids; used as a gas chromatography tailing agent; used as a plasticizer, etc.
production method	made from natural castor oil or adipic acid monoester. Sebacic acid can also be obtained by polymerization with ethylene and carbon tetrachloride, but almost all of the sebacic acid produced by industry in the world is made of castor oil. 1. Castor oil cracking method Castor oil is heated and hydrolyzed under the action of alkali to generate ricinoleic acid sodium soap, and then sulfuric acid is added to acidolysis to generate ricinoleic acid; in the presence of diluent cresol, add alkali and heat to 260-280 ℃ for cracking to generate sebic acid double sodium salt, secondary octanol and hydrogen. After the lysate is diluted with water, heat and add acid to neutralize, and turn the double sodium salt into a single sodium salt; then use the neutralization solution after decolorization, the monosodium salt of sebacic acid becomes sebacic acid crystals and precipitates, and then separates and dries to obtain the finished product. Raw material consumption quota: castor oil (industrial products) 2100kg/t, sulfuric acid (98%)1600kg/t, caustic soda (95%)1200kg/t, cresol (industrial products) 100kg/t. 2. Petroleum n-decane fermentation method uses n-decane separated from 200# solvent oil or 166-182 ℃ fraction to produce sebacic acid by fermentation with 19-2 Candida lipolysis. 3. The new cyclopentanone method uses palladium salt-copper or iron as a catalyst, in the solvent of ethanol, propanol or other alcohols, at a low temperature of 40-60 ℃ and atmospheric pressure Under mild conditions, cyclopentene is oxidized to produce cyclopentanone, and then oxidized and dimerized with iron catalyst.
category	flammable liquid
toxicity classification	low toxicity
acute toxicity	oral-rat LD50: 14375 mg/kg; Oral-mouse LD50: 6000 mg/kg
flammability hazard characteristics	combustible, spicy and irritating smoke from the fire site
storage and transportation characteristics	warehouse ventilation and low temperature drying
fire extinguishing agent	dry powder, foam, sand, water

Last Update：2024-04-09 02:00:06

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