DODECANEDIOIC ACID
DODECANEDIOIC ACID
Dodecanedioic acid = DDDA
CAS Number: 693-23-2
EC Number: 211-746-3
Chemical formula: C12H22O4
Molar mass: 230.304 g·mol−1
Dodecanedioic acid (DDDA) is a pure C12 dibasic acid that is mainly used in antiseptics, painting materials, top-grade coatings, corrosion inhibitors, surfactants and engineering plastics.
Dodecanedioic acid is available in a white, flaky form and has a long shelf life of approximately 3 years, depending on the storage methods.
There are two different ways to make DDDA: synthetic production and biotech production.
Dodecanedioic Acid is mainly used in top-grade powder coatings and paint, adhesives, pulp & paper, chemical and industrial facilities, surfactants, antiseptics.
In combination with Amine, DDDA is used to produce engineering plastics polyamide resins wich is a high performance nylon 6-12, adhesives, diester synthetic lubricants, fibers, curatives, plasticizers, polyester coatings, epoxy resins.
When used Dodecanedioic acid in a mixture with other dibasic acids DDDA is especially effective as a ferrous corrosion inhibitor for metalworking fluids, engine coolants, metal cleaners, aqueous hydraulic fluids.
DDDA can also be used as a complexing agent for lithium complex grease which will increase dropping point and improve mechanical stability.
Common Applications for DDDA:
Dodecanedioic acid is water soluble and has a metabolic pathway intermediate that is similar to lipids and carbohydrates.
This is why DDDA is currently being tested as a possible medication for type diabetes 2 patients.
Early research shows that DDDA can help patients maintain normal blood sugar and energy levels without raising blood glucose.
When discussing DDDA, however, Dodecanedioic acid almost always refers to industrial use.
Below are some of the most common applications for DDDA:
-High performance nylon 6, 12
-Adhesives
-Molding resins
-Powder coatings
-Fibers
-Plasticizers
-Epoxy resins
-Polyester coatings
-Polyamide resins
-Corrosion inhibitors
-Corrosion inhibitors (mixed with other dibasic acids)
Dodecanedioic acid (DDA) is highly useful to the chemical industry as a versatile precursor for producing the polyamide nylon-6,12, which is used for many technical applications, such as heat and chemical-resistant sheaths.
However, DDA synthesis has several drawbacks, such as high energy input and cost-intensive removal of by-products.
Therefore, alternative bio-based production routes are required due to increasing industrial demand for green chemicals and renewable products.
Candida tropicalis converts petrochemical-based n-dodecanes to the corresponding dicarboxylic acids by targeted functionalization.
To increase sustainability of the DDA production process, we tested dodecanoic acid methyl ester, which can be easily obtained from transesterification of coconut oil, in whole-cell biotransformation by C. tropicalis.
By modifying selected process parameters, a final DDA concentration of 66 g/L was achieved using a highly reliable, small-scale bioreactor system.
Crucial process development included a gradual pH shift, an optimized substrate feeding strategy, and monitoring the transcriptional profile.
Dodecanedioic acid (DDDA) is a dicarboxylic acid mainly used in antiseptics, top-grade coatings, painting materials, corrosion inhibitors, surfactants, and engineering plastics such as nylon 612.
Experimental work with dodecanedioic acid in type 2 diabetic patients has demonstrated that IV infusion helps to maintain normal blood sugar and energy levels without increasing the blood glucose load in the process.
Dodecanedioic Acid is a dicarboxylic acid used in the manufacturing of nylon 6, 12, adhesives, powder coatings and paints.
In addition DDDA is used in the production of corrosion inhibitors, which are extensively used for water treatment, pulp & paper, chemical facilities and other industrial facilities.
When used in a mixture with other dibasic acids DDDA is especially effective as a ferrous corrosion inhibitor for metalworking fluids, engine coolants, metal cleaners, aqueous hydraulic fluids, and die cast release agents.
DDDA can also be used as a complexing agent for lithium complex grease which will increase dropping point and improve mechanical stability.
Uses of Dodecanedioic acid:
Dodecanedioic acid (DDDA) is a pure C12 dibasic acid that is mainly used in antiseptics, painting materials, top-grade coatings, corrosion inhibitors, surfactants and engineering plastics.
Dodecanedioic acid is available in a white, flaky form and has a long shelf life of approximately 3 years, depending on the storage methods.
Dodecanedioic Acid (DDDA) is a highly pure C12 dibasic acid that is available in white flake form.
Dodecanedioic acid is commonly used in adhesives, corrosion inhibitors, capacitor electrolytes, diester synthetic lubricants, fibers, powder coating curatives, plasticizers, polyester coatings, epoxy resins, and polyamide resins.
Dodecanedioic acid is used extensively in many applications, such as resins, powder coatings, lubricants, and adhesives.
The resin application segment accounts for the largest share of the dodecanedioic acid market.
The powder coating application segment will be the fastest growing application segment over the forecast period due to the increased demand for paints and coatings from the automobile and construction industries.
Dodecanedioic acid Production:
DDDA is currently produced by both chemical and biological routes.
Chemical process of Dodecanedioic acid:
Dodecanedioic acid has traditionally been produced from butadiene using a multi-step chemical process.
Butadiene is first converted to cyclododecatriene through a cyclotrimerization process.
Cyclododecatriene is converted to dodecanedioic acid by hydrogenation to cyclododecane followed by air oxidation in the presence of boric acid at elevated temperatures to a mixture of the alcohol and the ketone.
In the final step, this mixture oxidized further by nitric acid.
DDA is used as a raw material for polyurethane resins, polyester resins, and polyamide resins, as well as a curing agent for acrylic powder paints.
When reacting with various alcohols and diamines, it produces polyester and polyamide resins with excellent performance, especially in hydrolytic resistance, flexibility, and heat stability.
CAS Number: 693-23-2
CHEBI: 4676
ChemSpider: 12213
ECHA InfoCard: 100.010.680
KEGG: C02678
PubChem CID: 12736
UNII: 978YU42Q6I
CompTox Dashboard (EPA): DTXSID3027297
Traditionally, DDDA is produced from butadiene using a chemical process.
First, the butadiene is converted into cyclododecatriene through a cyclotrimerization process.
The cyclododecatriene is then converted into dodecanedioic acid.
A newer approach is biotech production.
Using biotechnology, DDDA is created from paraffin wax.
This has made DDDA a cost-effective compound that is transforming the nylon market and showing up in products such as toothbrushes, cosmetics, adhesives, coatings, paints, automotive lubricants and corrosion inhibitors.
Dodecanedioic acid is a dicarboxylic acid which is water soluble and involves in a metabolic pathway intermediate to those of lipids and carbohydrates.
Dodecanedioid acid is an indicator of hepatic carnitine palmitoyltransferase I (CPT IA) deficiency.
CPT IA deficiency is characterized by hypoketotic dicarboxylic aciduria with high urinary levels of dodecanedioic acid.
This C12 dicarboxylic aciduria suggests that carnitine palmitoyltransferase I may play a role in the uptake of long-chain dicarboxylic acids by mitochondria after their initial shortening by beta-oxidation in peroxisomes.
Dodecanedioic acid Biological process
Paraffin wax can be converted into DDDA with a special strain of Candida tropicalis yeast in a multi-step process.
Renewable plant-oil feedstocks sourced from switchgrass can also be used to produce DDDA.
Chemical formula: C12H22O4
Molar mass: 230.304 g·mol−1
Appearance: White flakes
Density: 1.066 g/cm3
Melting point: 127–129 °C (261–264 °F; 400–402 K)
Boiling point: 245 °C (473 °F; 518 K)
Solubility in water: pH dependent
Dodecanedioic Acid (DDDA) is a dicarboxylic acid used in the manufacturing of nylon 6, 12, adhesives, powder coatings and paints.
The global demand for DDDA is anticipated to grow due to it being a key raw material for the production of Nylon 6, 12 which has a wide range of applications including polyesters, greases, coatings, detergents, adhesives, and fragrances.
In addition, DDDA is used in the production of corrosion inhibitors, which are extensively used for water treatment, pulp & paper, chemical facilities and other industrial facilities.
The rise in protective coatings and paints containing zero volatile organic compounds has also contributed to the growth of the chemical.
Recently manufacturers have been researching bio-based methods of manufacturing DDDA in order to meet the growing demand for eco-friendly products.
Dodecanedioic acid is traditionally produced from butadiene but the exploration has allowed manufacturers to switch to a lower cost plant-oil sourced feedstock.
DodecaneDioic Acid (DDDA)
Cas: 693-23-2
Dodecanedioic acid (DDDA) is a dibasic acid.
Dodecanedioic acid’s a white flakes solid with a molecular formula C12H22O4.
Dodecanedioic acid (DDDA) is a dicarboxylic acid mainly used in antiseptics, top-grade coatings, painting materials, corrosion inhibitors, surfactants, and engineering plastics such as nylon 612.
Experimental work with dodecanedioic acid in type 2 diabetic patients has demonstrated that IV infusion helps to maintain normal blood sugar and energy levels without increasing the blood glucose load in the process.
Dodecanedioic acid is used extensively in the production of polyamides, one of the most important raw materials required for manufacturing nylon-based products.
The increased demand for nylon products from India and China in the APAC region is one of the key factors for the growth of the dodecanedioic acid market.
The sudden growth of the construction and automotive industries, and the increased demand for paints and coatings will enhance the growth of the dodecanedioic acid market.
Nylon is also used to manufacture thermoplastics.
Synonym(s): Decane-1,10-dicarboxylic acid
Linear Formula: HOOC(CH2)10COOH
CAS Number: 693-23-2
Molecular Weight: 230.30
Beilstein/REAXYS Number: 1782580
EC Number: 211-746-3
MDL number: MFCD00002735
PubChem Substance ID: 24893317
NACRES: NA.22
Dodecanedioic acid Description:
Dodecanedioic acid is used in the production of nylon (nylon – 6,12), polyamides, coatings, adhesives, greases, polyesters, dyestuffs, detergents, flame retardants, and fragrances.
Dodecanedioic acid is now produced by fermentation of long-chain alkanes with a specific strain of Candida tropicalis.
Dodecanedioic acids monounsaturated analogue (traumatic acid) is described below.
Dodecanedioic acid Chemical Properties: white crystalline powder
Dodecanedioic acid Uses: Induced mutation of dodecanedioic acid producing Candida tropicalis.
Dodecanedioic acid Definition: ChEBI: An alpha,omega-dicarboxylic acid that is dodecane in which the methyl groups have been oxidised to the corresponding carboxylic acids.
Dodecanedioic acid Purification Methods: Crystallise the dioic acid from water, 75% or 95% EtOH (solubility is 10%), or glacial acetic acid.
Dodecanedioic acid informally referred to as DDDA is a saturated aliphatic dicarboxylic acid mainly used in antiseptics, top-grade coatings, painting materials, corrosion inhibitor, surfactant, and plastics.
Experimental work with Dodecanedioic acid in type 2 diabetic patients has demonstrated that IV infusion helps to maintain normal blood sugar and energy levels without increasing the blood glucose load in the process.
Quality Level: 100
vapor pressure: 21 mmHg ( 222 °C)
assay: 99%
bp: 245 °C/10 mmHg (lit.)
mp: 127-129 °C (lit.)
solubility: H2O: slightly soluble 3 g/L at 23 °C
SMILES string: OC(=O)CCCCCCCCCCC(O)=
InChI: 1S/C12H22O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h1-10H2,(H,13,14)(H,15,16)InChI key: TVIDDXQYHWJXFK-UHFFFAOYSA-N
Dodecanedioic Acid is a family of organic compounds with a chemical formula of HOOC(CH2)10COOH.
These compounds are known as ‘long-chain dicarboxylic acids’ when the total carbon number is greater than nine (n>7).
Long-chain diacids provide greater flexibility and strength than short-chain diacids due to their ability to bend, which minimizes breakage as well as reduces the number of links in a polymer.
Is produced from paraffin through fermentation followed by purification, rather than the traditional multi-step chemical process.
Dodecanedioic acid is used in clear powder coatings.
Production
There are two different routes to produce DDDA: synthetic production and biological production.
Traditionally, DDDA is produced from butadiene using a chemical process.
The butadiene is converted into cyclododecatriene through a cyclotrimerization process.
The cyclododecatriene is then converted into dodecanedioic acid.
Feedstock is methanol
A newer approach is biological production. Using biotechnology, DDDA is created from Paraffin wax with yeast (Candida Tropicalis).
This way has made DDDA a cost-effective compound.
Alternate Names: Decane-1,10-dicarboxylic acid; 1,10-Decanedicarboxylic acid
Application: Dodecanedioic acid is a saturated aliphatic dicarboxylic acid used in many applications
CAS Number: 693-23-2
Purity: 99%
Molecular Weight: 230.30
Molecular Formula: C12H22O4
Dodecanedioic acid is a chemical substance produced from butadiene by a chemical process.
A new way of producing Dodecanedioic acid by using yeast is coming into use, making it a cost advantage method.
At room temperature Dodecanedioic acid is solid with a slight odor.
Dodecanedioic acid is used in the manufacture of other chemicals like polyesters.
Dodecanedioic acid has no consumer uses.
Dodecanedioic acid is used in the manufacturing of tooth brushes, cosmetics, adhesives, coatings, paints, lubricants, automotive parts, fragrances, pharmaceuticals, fuel line tubing, etc.
Dodecanedioic acid also has laboratory use.
Dodecanedioic acid has a wide variety of applications – High performance polyamides, Polyester coatings, Diester synthetic lubricants, Adhesives, Corrosion inhibitors, Fibers, Powder coating curative, Plasticizers and Epoxy resin.
Catalogue Number: D494533
Chemical Name: Dodecanedioic-d20 Acid
Synonyms: 1,10-Decanedicarboxylic Acid-d20; 1,10-Dicarboxydecane-d20; 1,12-Dodecanedioic Acid-d20; Corfree M 2-d20; Decamethylenedicarboxylic Acid-d20; NSC 400242-d20; SL-AH-d20; n-Dodecane-α,ω-dioic Acid-d20; n-Dodecanedioic Acid-d20
CAS Number: 89613-32-1
Alternate CAS #: 693-23-2 unlabelled
Molecular Formula: C₁₂H₂D₂₀O₄
Appearance: White to Off-White Solid
Melting Point: 121- 124°C
Molecular Weight: 250.42
Storage: Refrigerator, under inert atmosphere
Solubility: DMSO (Slightly), Methanol (Slightly)
Category: Standards; Isotopic Labeled Analogues;
Dodecanedioic acid Applications: Dodecanedioic-d20 Acid is labelled Dodecanedioic Acid (D494530) which induces mutation of dodecanedioic acid producing Candida tropicalis.
Dodecanedioic Acid Market is segmented as below:
-Application
-Resins
-Powder Coatings
-Adhesives
-Lubricants
-Others
Dodecanedioic acid (DDA) is highly useful to the chemical industry as a versatile precursor for producing the polyamide nylon-6,12, which is used for many technical applications, such as heat and chemical-resistant sheaths.
However, DDA synthesis has several drawbacks, such as high energy input and cost-intensive removal of by-products.
Therefore, alternative bio-based production routes are required due to increasing industrial demand for green chemicals and renewable products.
Candida tropicalis converts petrochemical-based n-dodecanes to the corresponding dicarboxylic acids by targeted functionalization.
To increase sustainability of the DDA production process, we tested dodecanoic acid methyl ester, which can be easily obtained from transesterification of coconut oil, in whole-cell biotransformation by C. tropicalis.
By modifying selected process parameters, a final DDA concentration of 66 g/L was achieved using a highly reliable, small-scale bioreactor system.
Crucial process development included a gradual pH shift, an optimized substrate feeding strategy, and monitoring the transcriptional profile.
Melting point: 127-129 °C (lit.)
Boiling point: 245 °C/10 mmHg (lit.)
Density: 1,15 g/cm3
vapor pressure: 21 mm Hg ( 222 °C)
refractive index: 1.4437 (estimate)
RTECS: JR2370000
Flash point: 220 °C
storage temp: Sealed in dry, Room Temperature
solubility ethanol: 0.1 g/mL, clear
pka: 4.48±0.10(Predicted)
form: Pellets or Powder
color: White
PH5: (H2O, 20℃)(aqueous suspension)
Water Solubility: < 0.1 g/L (20 ºC)
Sensitive: Air Sensitive
Dodecanedioic acid (DDDA), is a highly pure C12 dibasic acid that is available in white flake form.
Dodecanedioic acid (DDDA), is a highly pure C12 dibasic acid that is available in white flake form.
Dodecanedioic acid Applications
Dodecanedioic acid in Coatings, Paints & Inks
-adhesives
-corrosion inhibitors
-powder coatings
Dodecanedioic acid in Lubricants, Fluids & Oilfield
-corrosion inhibitors
Dodecanedioic acid in Plastics
-nylon fibers
-plasticizers
Dodecanedioic acid Consumer Products
-organic compounds
Dodecanedioic acid Other Applications
-Adhesives
-Corrosion inhibitors
-Capacitor electrolyte
-Diester synthetic lubricants
-Fibers
-Plasticizers
-Polyester coatings
-Epoxy resins
-Polyamide resins
Production of dodecanedioic acid (DDDA), a platform chemical used as raw material for various commodities and polymers, has been studied through a biological process.
This process was conducted by using a wild-type of Candida tropicalis which can be obtained easily from natural resources.
The aim of this research was to study the characteristics of DDDA production from methyl laurate through batch fermentation process.
Growth phase was carried out for 20 h, as the beginning of fermentation, then continued to conversion phase for 5 until 6 days.
Utilization of methyl laurate and production of DDDA were analysed using gas chromatography, which proved the ability of C.
tropicalis in assimilating methyl laurate to convert it become DDDA.
The highest value of cells yield (Yx/s) and DDDA yield (Yp/s) successfully obtained were 0.86 g cells/g methyl laurate and 0.20 g DDDA/g methyl laurate, respectively.
This study also showed the possibility of fermentation products accumulation as intermediate, or accumulation of DDDA inside the cells.
Thus, this study can be applied as an alternative in addition to the use of mutant microorganism in producing DDDA.
Molecular Formula: C12H22O4
Molecular Weight: 230.30067
Physical State: Solid
Purity: >98%
Smiles: OC(=O)CCCCCCCCCCC(=O)O
Supplied As: Neat
Synonyms: Decamethylenedicarboxylic acid
Dicarboxylic acids (DA) are formed from the ω-oxidation of monocarboxylic acids when the β-oxidation of free fatty acids is impaired.
Medium-chain DA have the peculiar characteristic of being water soluble due to the presence of two carboxylic terminal groups in the molecule.
Contrary to both long- and medium-chain triglycerides which are administered as emulsions, they can be given by a peripheral vein as inorganic salts.
DA are β-oxidized at level of both peroxisomes and mitochondria via carnitine-independent pathway.
The products of β-oxidation of odd-chain DA are acetyl-CoA and malonyl-CoA, which cannot be oxidized further, are used in lipogenesis.
Moreover even-chain DA produce acetyl-CoA and succinyl-CoA, which is a gluconeogenetic precursor.
Azelaic acid (C9), does not show acute or chronic toxicity effects in animals but much of Dodecanedioic acid islost in urine (more than 50% of the given dose).
Sebacic acid (C10) is lost in urine to a smaller extent (about 12% of the administered dose) and its energy density (6.64 Kcal/g) is greater than that of C9 (4.97 Kcal/g).
Dodecanedioic acid (C12) seems to be the best candidate for parenteral nutrition, because Dodecanedioic acid is eliminated in the urine only in minimal amounts (3.90% of the given dose), Dodecanedioic acid is rapidly utilized by tissues, and Dodecanedioic acid has a high energy density (7.20 Kcal/g).
The linear dicarboxylic acid 1,12-dodecanedioic acid (DDDA) has a melting point of 128°C.
Dodecanedioic acid is virtually insoluble in water at room temperature.
The most important area of application of DDDA is for production of polyamides such as polyamide 612 or specialty polyamide.
DDDA is also used in the production of hotmelt adhesives and as a crosslinker for powder coatings.
DDDA finds application in corrosion inhibitors.
Dodecanedioic acid also serves a starting material in the fragrance industry.
DODECANEDIOIC ACID
693-23-2
1,12-Dodecanedioic acid
1,10-Decanedicarboxylic acid
Decamethylenedicarboxylic acid
1,10-Dicarboxydecane
MFCD00002735
n-Dodecanedioic acid
UNII-978YU42Q6I
CHEBI:4676
978YU42Q6I
1,10-Decanedicarboxylic acid, 99%
NSC400242
DSSTox_CID_7297
DSSTox_RID_78394
DSSTox_GSID_27297
CAS-693-23-2
HSDB 5745
EINECS 211-746-3
NSC 400242
n-Dodecanedioate
dodecane dioic acid
Corfree M 2
128017-64-1
1,12-Dodecanedioate
n-Dodecane-a,w-dioate
PubChem18097
1,10-dicarboxy decane
ACMC-1BHHD
SL-AH
Decamethylenedicarboxylate
1,10-Decanedicarboxylate
Dodecanedioic acid, 99%
n-Dodecane-a,w-dioic acid
EC 211-746-3
SCHEMBL29467
Dodecanedioic acid, homopolymer
1, 10-Decanedicarboxylic acid
Decane-1,10-dicarboxylic acid
CHEMBL3182356
DTXSID3027297
ZINC1529497
Dodecanedioic acid-1,12-[13C2]
Tox21_201954
Tox21_303308
ANW-35636
BBL018825
LMFA01170009
s6267
SBB060281
STL195386
AKOS015892807
CS-W012957
HY-W012241
MCULE-6168408668
NSC-400242
NCGC00163995-01
NCGC00163995-02
NCGC00257191-01
NCGC00259503-01
AC-10611
AK-96039
DS-18055
R902
D0013
FT-0606028
ST51046498
C02678
Q5287812
53037-60-8
1,10-Decanedicarboxylic acid
1,12-Dodecanedioate
1782580 [Beilstein]
211-746-3 [EINECS]
693-23-2 [RN]
Acide dodécanedioïque [French] [ACD/IUPAC Name]
Corfree M 2 [Trade name]
decamethylenedicarboxylic acid
Decane-1,10-dicarboxylic acid
Dodecandisäure [German] [ACD/IUPAC Name]
Dodecanedioic acid [ACD/Index Name] [ACD/IUPAC Name] [Wiki]
MFCD00002735 [MDL number]
n-Dodecanedioate
n-Dodecanedioic acid
n-Dodecane-α,ω-dioic acid
1,10-decane dicarboxylic acid
1,10-decanedicarboxylic acid 98%
1,10-decanedicarboxylic acid, 99%
1,10-dicarboxydecane
1,12 DODECANEDIOIC ACID
1,12-Dodecandisure
1,12-DODECANEDIOIC ACID
2,2,11,11-Tetradeuteriododecanedioic acid
2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11-Icosadeuteriododecanedioic acid
89613-32-1 [RN]
97543-02-7 [RN]
ammoniumdodecanedioate
DDDA
Dodecanedicarboxylic acid
dodecanedioic acid 99%
dodecanedioic acid, 99%
Dodecanedioic acid;DDDA
n-Dodecane-a,w-dioic acid
十二烷二酸 [Chinese]
十二烷二酸