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Sebacic acid information


Sebacic acid
Skeletal formula of sebacic acid
Ball-and-stick model of the sebacic acid molecule
Names
Preferred IUPAC name
Decanedioic acid
Other names
1,8-Octanedicarboxylic acid
Decane-1,10-dioic acid
Identifiers
CAS Number
  • 111-20-6 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:41865 checkY
ChemSpider
  • 5004 checkY
ECHA InfoCard 100.003.496 Edit this at Wikidata
EC Number
  • 203-845-5
MeSH C011107
PubChem CID
  • 5192
UNII
  • 97AN39ICTC checkY
CompTox Dashboard (EPA)
  • DTXSID7026867 Edit this at Wikidata
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) ☒N
    Key: CXMXRPHRNRROMY-UHFFFAOYSA-N ☒N
  • 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)
    Key: CXMXRPHRNRROMY-UHFFFAOYAE
SMILES
  • OC(=O)CCCCCCCCC(=O)O
Properties
Chemical formula
C10H18O4
Molar mass 202.250 g·mol−1
Density 1.209 g/cm3
Melting point 131 to 134.5 °C (267.8 to 274.1 °F; 404.1 to 407.6 K)
Boiling point 294.4 °C (561.9 °F; 567.5 K) at 100 mmHg
Solubility in water
0.25 g/L[1]
Acidity (pKa) 4.720, 5.450[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Sebacic acid is a naturally occurring dicarboxylic acid with the chemical formula HO2C(CH2)8CO2H. It is a white flake or powdered solid. Sebaceus is Latin for tallow candle, sebum is Latin for tallow, and refers to its use in the manufacture of candles. Sebacic acid is a derivative of castor oil.[2]

In the industrial setting, sebacic acid and its homologues such as azelaic acid can be used as a monomer for nylon 610, plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc.

It can be used as a surfactant in the lubricating oil industry to increase the antirust properties of lubricating oils on metals.

  1. ^ a b Bretti, C.; Crea, F.; Foti, C.; Sammartano, S. (2006). "Solubility and Activity Coefficients of Acidic and Basic Nonelectrolytes in Aqueous Salt Solutions. 2. Solubility and Activity Coefficients of Suberic, Azelaic, and Sebacic Acids in NaCl(aq), (CH3)4NCl(aq), and (C2H5)4NI(aq) at Different Ionic Strengths and at t = 25 °C". J. Chem. Eng. Data. 51 (5): 1660–1667. doi:10.1021/je060132t.
  2. ^ Cornils, Boy; Lappe, Peter (2000). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_523. ISBN 978-3527306732.

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Sebacic acid

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Sebacic acid is a naturally occurring dicarboxylic acid with the chemical formula HO2C(CH2)8CO2H. It is a white flake or powdered solid. Sebaceus is Latin...

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Dicarboxylic acid

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including other names, ids, toxicity and safety. Acids from the two-carbon oxalic acid to the ten-member sebacic acid may be remembered using the mnemonic 'Oh...

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Nylon

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adipic acid; PA 66/610: [NH−(CH2)6−NH−CO−(CH2)4−CO]n−[NH−(CH2)6−NH−CO−(CH2)8−CO]m made from hexamethylenediamine, adipic acid and sebacic acid. The term...

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Sebacoyl chloride

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aliphatic acyl chlorides. Sebacoyl chloride can be prepared by reacting sebacic acid with an excess of thionyl chloride. Residual thionyl chloride can be...

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Ricinoleic acid

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oil. The first attempts to prepare ricinoleic acid were made by Friedrich Krafft in 1888. Sebacic acid ((CH2)8(CO2H)2), which is used in preparing certain...

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List of carboxylic acids

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Carboxylic acids are organic acids characterized by a carboxyl (-COOH) functional group. The naming of these compounds is governed by IUPAC nomenclature...

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Dioctyl sebacate

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DOS, DEHS, and BEHS) is an organic compound which is the diester of sebacic acid and 2-ethylhexanol. It is an oily colorless liquid and is used as a plasticizer...

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Castor oil

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fragrance component and a specialized solvent, and the dicarboxylic acid sebacic acid. Hydrogenation of castor oil saturates the alkenes, giving a waxy...

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Azelaic acid

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Coefficients of Acidic and Basic Nonelectrolytes in Aqueous Salt Solutions. 2. Solubility and Activity Coefficients of Suberic, Azelaic, and Sebacic Acids in NaCl(aq)...

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Decalin

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tertiary hydroperoxide, which rearranges to cyclodecenone, a precursor to sebacic acid. Decalin is the saturated analog of naphthalene and can be prepared from...

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Kolbe electrolysis

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industrial applications. In one example, sebacic acid has been produced commercially by Kolbe electrolysis of adipic acid. Kolbe electrolysis has been examined...

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Suberic acid

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Coefficients of Acidic and Basic Nonelectrolytes in Aqueous Salt Solutions. 2. Solubility and Activity Coefficients of Suberic, Azelaic, and Sebacic Acids in NaCl(aq)...

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Arkema

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Braven makes sealants for insulation and construction. Casda manufactures sebacic acid from castor oil. Arkema operates through industrial facilities in Europe...

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Dibutyl sebacate

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Dibutyl sebacate (DBS) is an organic chemical, a dibutyl ester of sebacic acid. Its main use is as a plasticizer in production of plastics, namely cellulose...

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Polyester

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biodegradable polyesters of ethylene glycol and butylene glycol from sebacic acid". Acta Biomaterialia. 8 (8): 2911–8. doi:10.1016/j.actbio.2012.04.026...

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Nerve guidance conduit

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microstresses. PGS is synthesized by a polycondensation reaction of glycerol and sebacic acid, which can be melt processed or solvent processed into the desired shape...

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C10H18O4

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molecular formula C10H18O4 (molar mass: 202.25 g/mol) may refer to: Sebacic acid 1,4-Butanediol diglycidyl ether This set index page lists chemical structure...

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Justinus Kerner

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medical books, dealing with animal magnetism, the first treatise on sebacic acid and botulism, Das Fettgift oder die Fettsäure und ihre Wirkung auf den...

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List of compounds with carbon number 11

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Adipic acid dihydrazide

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organic acid with hydrazine. Other dihydrazides with different backbones are also common, including isophthalic dihydrazide (IDH) and sebacic dihydrazide...

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Dinalbuphine sebacate

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pain. The compound is a diester of nalbuphine (Nubain) joined via a sebacic acid linker, and acts as a long-lasting prodrug of nalbuphine via slow hydrolysis...

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Elmer Keiser Bolton

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fibers could not be made from castor oil, the only practical source of sebacic acid. To use an agricultural product as a primary feedstock would mean the...

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