Sebacic acid

Iupac Name：decanedioic acid

Molecular Weight：202.24800

Modify Date.: 2022-11-10 17:14

Introduction: 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. View more+

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1. Names and Identifiers

1.1 Name: Sebacic acid
1.2 Synonyms: 1,10-Decanedioic acid 1,10-decanedioicacid 1,8-OCTANEDICARBOXYLIC ACID acidesebacique decane-1,10-dioic acid Decanedioic DECANEDIOIC ACID EINECS 203-845-5 MFCD00004440 octane-1,8-dicarboxylic acid RARECHEM AL BO 0380 SEBACINIC ACID sebacinsaure Sebacinsure Seracic acid UNII-97AN39ICTC

1.3 CAS No.: 111-20-6

1.4 CID: 5192

1.5 EINECS(EC#): 203-845-5

1.6 Molecular Formula: C10H18O4 (isomer)

1.7 Inchi: InChI=1S/C10H18O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-8H2,(H,11,12)(H,13,14)

1.8 InChkey: CXMXRPHRNRROMY-UHFFFAOYSA-N

1.9 Canonical Smiles: C(CCCCC(=O)O)CCCC(=O)O

1.10 Isomers Smiles: C(CCCCC(=O)O)CCCC(=O)O

2. Properties

2.1 Density: 1.21

2.1 Melting point: 133-137°C(lit.)

2.1 Boiling point: 294.5°C100mm Hg(lit.)

2.1 Refractive index: 1.422

2.1 Flash Point: 220 °C

2.1 Precise Quality: 202.12100

2.1 PSA: 74.60000

2.1 logP: 2.27640

2.1 Solubility: ethanol: 100?mg/mL

2.2 Appearance: white powder

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: It is white flaky crystal. It is slightly soluble in water, soluble in alcohol and ether.

2.5 Color/Form: Powder

2.6 Physical: PHYSICAL DESCRIPTION: White granular powder. Melting point 153°F. Slightly soluble in water;. Sublimes slowly at 750 mm Hg when heated to melting point.

2.7 pKa: 4.59, 5.59(at 25℃)

2.8 Water Solubility: 1 g/L (20 oC)

2.9 Stability: Stable. Combustible. Incompatible with strong oxidizing agents, bases, reducing agents.

2.10 StorageTemp: Store below +30°C.

3. Use and Manufacturing

3.1 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 1524 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1511 of 1524 companies. For more detailed information, please visit ECHA C&L website

Of the 5 notification(s) provided by 13 of 1524 companies with hazard statement code(s):

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (92.31%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (69.23%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501

3.2 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 Preparation Products

3.3 Usage: 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.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26-S36

4.1 Fire Hazard: Flash point data for Sebacic acid are not available. Sebacic acid is probably combustible.

4.2 RIDADR: NONH for all modes of transport

4.2 WGK Germany: 1

4.2 RTECS: VS0875000

4.2 Report: Reported in EPA TSCA Inventory.

4.3 Safety: Moderately toxic by ingestion and intraperitoneal routes. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes:?Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S25:Avoid contact with eyes.?
S36:Wear suitable protective clothing.
WGK Germany: 1
RTECS: VS0875000
HS Code: 29171310

4.4 Specification: ?Sebacic acid , with CAS number of 111-20-6, can be called decanedioic acid ; Sebacic acid ; 1, 10-Decanedioic acid ; 1,10-decanedioic acid ; Decanedioic acid ; 1,8-Octanedicarboxylic acid ; decanedioate . It is a?white powder,? Sebacic acid (CAS NO.111-20-6) is also used as an intermediate for antiseptics,aromatics and painting materials.?Sebacic acid (CAS NO.111-20-6) is a low toxic substance, with flammability, burning will produce toxic fumes, so it should be stored in cool and dry environment, dry powder, foam, sand, carbon dioxide, water mist can be used if something urgent happened.

4.5 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mammal (species unspecified)	LC	inhalation	> 900mg/m³ (900mg/m³)	SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION BEHAVIORAL: EXCITEMENT	Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 24(5), Pg. 48, 1980.
mammal (species unspecified)	LD50	intraperitoneal	1175mg/kg (1175mg/kg)	?	Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 24(5), Pg. 48, 1980.
mammal (species unspecified)	LD50	oral	> 11gm/kg (11000mg/kg)	?	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(9), Pg. 72, 1983.
mouse	LD50	intraperitoneal	500mg/kg (500mg/kg)	?	National Technical Information Service. Vol. AD277-689,
mouse	LD50	oral	6gm/kg (6000mg/kg)	?	Biochemical Journal. Vol. 34, Pg. 1196, 1940.
rat	LC50	inhalation	> 4500mg/m³ (4500mg/m³)	?	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 57(2), Pg. 17, 1992.
rat	LD50	oral	14375mg/kg (14375mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: EXCITEMENT BEHAVIORAL: FOOD INTAKE (ANIMAL)	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 57(2), Pg. 17, 1992.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

IR : KBr disc

IR : nujol mull

7. Synthesis Route

111-20-6Total: 29 Synthesis Route

60-33-3 215 Suppliers

110-94-1 208 Suppliers

111-20-6 378 Suppliers

142-62-1 174 Suppliers

107-92-6 190 Suppliers

Literatures:
Ann.Chim.applic., , vol. 29, p. 303 Chem. Zentralbl., , vol. 110, # II p. 4394
Yield: null

693-55-0 15 Suppliers

111-20-6 378 Suppliers

110-40-7 85 Suppliers

Literatures:
Chemische Berichte, , vol. 55, p. 2218
Yield: null

502-75-0 2 Suppliers

503-74-2 152 Suppliers

111-20-6 378 Suppliers

Literatures:
Kromer Journal fuer Praktische Chemie (Leipzig), 1898 , vol. <2>57, p. 454
Yield: null

View all

8. Precursor and Product

precursor:

5810-19-5

112-80-1

7327-98-2

122-62-3

1577-55-5

1119-46-6

1724-39-6

112-47-0

141-22-0

67-56-1

71-43-2

60-33-3

544-78-5

120-92-3

627-91-8

293-96-9

3618-12-0

956-82-1

1740-54-1

502-75-0

693-55-0

64-19-7

830-13-7

View all

product :

3710-30-3

929-77-1

593-50-0

373-44-4

1871-96-1

925-83-7

5166-58-5

462-68-0

6833-06-3

111-19-3

6712-10-3

646-25-3

2561-88-8

818-88-2

111-50-2

818-26-8

1826-76-2

110-94-1

693-54-9

593-15-7

6946-46-9

693-55-0

629-83-4

629-40-3

7512-29-0

View all

9. Other Information

9.0 Merck: 14,8415

9.1 BRN: 1210591

9.2 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 andy.（2016-12-04）

9.3 Chemical properties: It is white flaky crystal. It is slightly soluble in water, soluble in alcohol and ether.

9.4 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.

9.5 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.

9.6 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.

9.7 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.

9.8 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

9.9 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.

9.10 Chemical Properties: white powder

9.11 Uses: Sebacic Acid is a urinary metabolite that has been identified as an anti-fatigue biomarker.

9.12 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.

9.13 Usage: Sebacic acid is used as a monomer for nylon 610, plasticizers, lubricants, hydraulic fluids, cosmetics and candles. It is also used as intermediates in antiseptics, aromatics and painting materials. It is used in the synthesis of poly(glycerol sebacate) and novel bio-nylon. It finds application as adhesives, corrosion inhibitors and solvents. Its derivative, diethyl Sebacate is used in plastics manufacturing and engineering, as well as drug delivery procedures through the use of biodegradable encapsulations.

9.14 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.]

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

9.16 Air & Water Reactions: Insoluble in water.

9.17 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.

9.18 Fire Hazard: Flash point data for Sebacic acid are not available. Sebacic acid is probably combustible.

10. Computational chemical data

Molecular Weight: 202.24800g/mol
Molecular Formula: C₁₀H₁₈O₄
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 202.12050905
Monoisotopic Mass: 202.12050905
Complexity: 157
Rotatable Bond Count: 9
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 74.6
Heavy Atom Count: 14
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceBwOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAACAAACACAgAAACAAAAgAIAACQCAAAAAAAAAAAAAEAAAAAABIAAAAAQAAEAAAAAAGIyKCAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

11. Question & Answer

Sebacic acid—an aliphatic dibasic acid Oct 19 2020
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 ins...

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