PRODUCTS

DECANEDIOIC ACID

CAS NO:693-23-2
EC NO:211-746-3

Decanedioic acid is an alpha,omega-dicarboxylic acid that is dodecane in which the methyl groups have been oxidised to the corresponding carboxylic acids.

Decanedioic acid has a role as an EC 1.1.1.1 (alcohol dehydrogenase) inhibitor and a human metabolite.
Decanedioic acid is an alpha,omega-dicarboxylic acid and a dicarboxylic fatty acid.
Decanedioic acid is a conjugate acid of a dodecanedioate(2-).
Decanedioic acid derives from a hydride of a dodecane.

Decanedioic acid is a natural product found in Phaseolus vulgaris, Trypanosoma brucei, and other organisms with data available.

Decanedioic acid is a metabolite found in the aging mouse brain.

Uses:
Used as intermediate for plasticizers, lubricants, adhesives, polyesters, and others;
INTERMEDIATE.

Decanedioic acid is a saturated, straight-chain naturally occurring dicarboxylic acid with 10 carbon atoms.
Decanedioic acid is a normal urinary acid. In patients with multiple acyl-CoA-dehydrogenase deficiency (MADD), also known as glutaric aciduria type II (GAII), a group of metabolic disorders due to deficiency of either electron transfer flavoprotein or electron transfer flavoprotein ubiquinone oxidoreductase, biochemical data shows an increase in urine sebacic acid excretion.
Decanedioic acid is found to be associated with carnitine-acylcarnitine translocase deficiency and medium chain acyl-CoA dehydrogenase deficiency, which are inborn errors of metabolism.
Decanedioic acid is a white flake or powdered crystal slightly soluble in water that has been proposed as an alternative energy substrate in total parenteral nutrition.
Decanedioic acid was named from the Latin sebaceus (tallow candle) or sebum (tallow) in reference to its use in the manufacture of candles.
Decanedioic acid and its derivatives such as azelaic acid have a variety of industrial uses as plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc.
Decanedioic acid is used in the synthesis of polyamide and alkyd resins.
Decanedioic acid is also used as an intermediate for aromatics, antiseptics and painting materials

Formula: C10H18O4 /HOOC(CH2)8COOH
Molecular mass: 202.3
Boiling point at 13.3kPa: 294°C
See Notes.
Melting point: 131°C
Density: 1.2 g/cm³
Solubility in water, g/100ml: 0.1 (poor)
Flash point: 220°C
Octanol/water partition coefficient as log Pow: 2.2

Decanedioic acid is a naturally occurring dicarboxylic acid with the chemical formula (CH2)8(CO2H)2.
Decanedioic acid 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.
Decanedioic acid is a derivative of castor oil.

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.

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
Acidity (pKa):   4.720, 5.450

Production
Decanedioic acid is produced from castor oil by cleavage of ricinoleic acid, which is obtained from castor oil. Octanol & glycerin is a byproduct.

Decanedioic acid can also be obtained from decalin via the tertiary hydroperoxide, which gives cyclodecenone, a precursor to sebacic acid.

Decanedioic acid is suggested that sebacic acid is converted to its 5-oxo analog during, and thereby stimulates pro-inflammatory cells to contribute to the worsening of, various inflammatory skin conditions.
Decanedioic acid is also found in other lipids that coat the skin surface.

Decanedioic acid is a white granular powder. Melting point 153°F. Slightly soluble in water. Sublimes slowly at 750 mm Hg when heated to melting point.

Decanedioic acid is an alpha,omega-dicarboxylic acid that is the 1,8-dicarboxy derivative of octane.
Decanedioic acid has a role as a human metabolite and a plant metabolite.
Decanedioic acid is an alpha,omega-dicarboxylic acid and a dicarboxylic fatty acid.
Decanedioic acid is a conjugate acid of a sebacate(2-) and a sebacate.
Decanedioic acid derives from a hydride of a decane.

Decanedioic acid is a natural product found in Isatis tinctoria, Phaseolus vulgaris, and other organisms with data available.

Decanedioic acid is used as a raw material for alkyd and polyester resins, plasticizers, polyester rubbers, and polyamide synthetic fibers;
Decanedioic acid is used as a topical emollient;
Decanedioic acid is used as a stabilizer in alkyd resins, maleic and other polyesters, polyurethanes, and fibers;
Decanedioic acid is used in paint products, candles, perfumes, low temperature lubricants, and hydraulic fluids, and to make nylon.

Industry Uses:
-Adhesives and sealant chemicals
-Corrosion inhibitors and anti-scaling agents
-Intermediates
-Ion exchange agents
-Lubricants and lubricant additives
-Paint additives and coating additives not described by other categories
-Plasticizers
-Process regulators
-Reactant
-Surface active agents
-personal care and cosmetics

Consumer Uses
-Adhesives and sealants
-Anti-freeze and de-icing products
-Automotive care products
-Lubricants and greases
-Paints and coatings
-Personal care products
-Water treatment products

Industry Processing Sectors:
-Adhesive manufacturing
-All other basic inorganic chemical manufacturing
-All other basic organic chemical manufacturing
-All other chemical product and preparation manufacturing
-Machinery manufacturing
-Miscellaneous manufacturing
-Paint and coating manufacturing
-Petroleum lubricating oil and grease manufacturing
-Plastic material and resin manufacturing
-Plastics product manufacturing
-Synthetic rubber manufacturing
-Transportation equipment manufacturing
-personal care and cosmetics

General description
Decanedioic acid is a castor oil-derived dicarboxylic acid.
Decanedioic acid is widely used to produce polymers, plasticizers, lubricants, and corrosion retardants.
Decanedioic acid can act as a pH corrector in the cosmetic products formulations.
Decanedioic acid is also used as a precursor to prepare sebacate esters such as diisopropyl sebacate, diethylhexyl sebacate, and dibutyl sebacate.

Application
Decanedioic acid has been used in the synthesis of:
-biodegradable and elastomeric polyesters [poly(glycerol sebacate)]
-novel bio-nylon, PA5.10
-novel temperature-response hydrogel based on poly(ether-ester anhydride) nanoparticle for drug-delivery applications

Properties
-High purity
-100% of vegetal origin
-Linear chain
-Granules or powder forms
-High reactivity to produce a wide range of esters

Major Applications
Decanedioic acid offers a competitve solution in many applications:

To produce polymers
In industry: to produce plasticizers, lubricants, and corrosion retardants
In cosmetics: as buffering ingredient or as a chemical intermediate to produce a wide range of esters

Cosmetic applications
Decanedioic acid can be used directly in cosmetics formulation as a pH corrector (buffering). In this case, the main applications are skin care (mainly face/neck care), and color cosmetics.

Plasticizers applications
The Decanedioic acid (DC 10), is widely used to produce a various range of plastics, and brings to those plastics a bio-based part.

Decanedioic acid is widely used to produce a salt derivative, the (di)sodium sebacate, which is a corrosion inhibitor. The main application of this salt is coolant (anti-freeze) fluids for aircraft, automotive and truck engines.

Decanedioic acid is also a raw material to produce sebacate diesters (DOS, DBS, …), used in complexed greases or lubricants. Generally, diesters are used as base oils for high performance lubricants (automotive, aerospace turbines, high reliability industrial hydraulics and compressor systems).

Physicochemical Information:
Boiling point:   295 °C (133 hPa)
Density:1.210 g/cm3 (20 °C)
Melting Point:   133 - 137 °C
Vapor pressure:   1 hPa (183 °C)
Bulk density:   600 - 620 kg/m3
Solubility:   1 g/l

Chemical properties

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

Uses
Decanedioic 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.
Decanedioic acid 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.
Decanedioic acid 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.

Production method
Almost all of the current industrial production of sebacic acid is using castor oil as raw material.

Description
Decanedioic 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.
Decanedioic acid 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.
Decanedioic 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.
Decanedioic acid is also used as an intermediate for aromatics, antiseptics, and painting materials.

Chemical Properties
White flaky crystals. Slightly soluble in water, soluble in alcohol and ether.

Uses
Decanedioic acid is a urinary metabolite that has been identified as an anti-fatigue biomarker.

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.
Decanedioic acid and its derivatives, as azelaic acid, have a variety of industrial uses as plasticizers, lubricants, diffusion pump oils, cosmetics, candles, etc.
Decanedioic acid 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.

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

About Decanedioic acid
Helpful information
Decanedioic acid is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 tonnes per annum.

Decanedioic acid is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

Consumer Uses
Decanedioic acid is used in the following products: washing & cleaning products, adhesives and sealants, fuels, lubricants and greases, coating products and fertilisers.
Release to the environment of Decanedioic acid can occur from industrial use: of substances in closed systems with minimal release.
Other release to the environment of Decanedioic acid is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use, indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters) and outdoor use in close systems with minimal release (e.g. hydraulic liquids in automotive suspension, lubricants in motor oil and break fluids).

Article service life
Release to the environment of Decanedioic acid can occur from industrial use: formulation of mixtures and in the production of articles. Other release to the environment of Decanedioic acid is likely to occur from: indoor use and outdoor use resulting in inclusion into or onto a materials (e.g. binding agent in paints and coatings or adhesives). Decanedioic acid can be found in products with material based on: plastic (e.g. food packaging and storage, toys, mobile phones) and leather (e.g. gloves, shoes, purses, furniture).

Widespread uses by professional workers
Decanedioic acid is used in the following products: biocides (e.g. disinfectants, pest control products), pH regulators and water treatment products, laboratory chemicals, plant protection products, water softeners and water treatment chemicals.
Decanedioic acid is used in the following areas: formulation of mixtures and/or re-packaging and agriculture, forestry and fishing.
Decanedioic acid is used for the manufacture of: chemicals.
Other release to the environment of Decanedioic acid is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.

Formulation or re-packing
Decanedioic acid is used in the following products: adhesives and sealants, polymers, coating products, lubricants and greases and cosmetics and personal care products.
Release to the environment of Decanedioic acid can occur from industrial use: formulation of mixtures, in processing aids at industrial sites, as processing aid, as an intermediate step in further manufacturing of another substance (use of intermediates), for thermoplastic manufacture, manufacturing of the substance and formulation in materials.

Uses at industrial sites
Decanedioic acid is used in the following products: laboratory chemicals, water treatment chemicals, pH regulators and water treatment products, water softeners and polymers.
Decanedioic acid is used in the following areas: formulation of mixtures and/or re-packaging.
Decanedioic acid is used for the manufacture of: chemicals, plastic products and rubber products.
Release to the environment of Decanedioic acid can occur from industrial use: in processing aids at industrial sites, in the production of articles, formulation of mixtures, as an intermediate step in further manufacturing of another substance (use of intermediates), as processing aid and for thermoplastic manufacture.

Manufacture
Release to the environment of Decanedioic acid can occur from industrial use: manufacturing of the substance.

IUPAC names:
1,10-Decane dioic acid
1,8-octane dicarboxylic acid
1,8-Octanedicarboxylic Acid
decandioic acid
DECANEDIOIC ACID
Decanedioic acid
decanedioic acid
Decanedioic acid
n-Decanedioic acid
Sebacic Acid
Decanedioic acid
sebacic acid
Sebacic Acid
Decanedioic acid
sebacic acid

SYNONYMS:
1,10-decanedioic acid
111-20-6 [RN]
1210591 [Beilstein]
203-845-5 [EINECS]
Acide sebacique [French]
Acide sébacique [French] [ACD/IUPAC Name]
Decanedioic acid [ACD/Index Name]
MFCD00004440 [MDL number]
Decanedioic acid [ACD/IUPAC Name] [Wiki]
Sebacinsaure [German]
Sebacinsäure [German] [ACD/IUPAC Name]
VS0875000
Ipomic acid
Seracic acid
[111-20-6]
1, 10-Decanedioic acid
1,10-Decanedicarboxylic acid
1,10-Decanedioic-2,2,9,9-d4 Acid
1,10-Decanedioic-d16 Acid
1,8-dicarboxyoctane
1,8-Octanedicarboxylic acid
1,8-Octanedicarboxylic acid (Decanedioic acid)
26776-29-4 [RN]
32734-00-2 [RN]
339080-77-2 [RN]
4-02-00-02078 [Beilstein]
4-02-00-02078 (Beilstein Handbook Reference) [Beilstein]
5505-62-4 [RN]
693-23-2 [RN]
72162-23-3 [RN]
73351-71-0 [RN]
Acide sebacique
CHEBI:41865