627-93-0 Usage
Description
Dimethyl adipate (DMA) is a colorless, flammable liquid that is soluble in alcohol and ether but sparingly soluble in water. It is a fatty acid methyl ester and is synthesized by the esterification of adipic acid. DMA is incompatible with strong oxidizing agents and, upon decomposition, emits carbon monoxide, irritating and toxic fumes and gases, and carbon dioxide. It reacts with acids, alkalis, and strong oxidants.
Uses
Used in Cosmetics:
Dimethyl adipate is used as an emollient and skin conditioning agent in the cosmetics industry. It acts as a cosmetic plasticizer, providing a smooth and soft texture to the skin.
Used in Plasticizers:
Dimethyl adipate is used as a plasticizer for cellulose-type resins, enhancing the flexibility and workability of the material.
Used in Paint Stripping:
Dimethyl adipate serves as a solvent for paint stripping, effectively removing paint from various surfaces.
Used in Cellulose Resins:
Dimethyl adipate is used in the production of cellulose resins, which are utilized in various applications, including coatings and adhesives.
Used in Agrochemicals and Dyes:
Dimethyl adipate is employed as a precursor in the preparation of active pharmaceutical ingredients and is also used in the agrochemical and dye industries.
Used as a Polymer Intermediate:
Dimethyl adipate is used as a chemical intermediate in the synthesis of polymers and agrochemicals.
Used in Specialty Solvents:
Dimethyl adipate is utilized as a specialty solvent in inks, coatings, and adhesives, providing specific properties and performance characteristics to these products.
Production Methods
Dimethyl adipate is manufactured via esterification of adipic
acid and methanol in the presence of an acid catalyst.
Reactivity Profile
Dimethyl adipate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
Health Hazard
Exposures to dimethyl adipate cause toxicity and adverse health effects in laboratory
animals and humans. Workplace exposures to dimethyl adipate by inhalation, ingestion,
or skin absorption cause harmful and irritation effects to users.
Flammability and Explosibility
Nonflammable
Safety Profile
Moderately toxic by
intraperitoneal route. Experimental
teratogenic and reproductive effects. When
heated to decomposition it emits acrid
smoke and irritating fumes.
Synthesis
Dimethyl adipate was synthesized by immobilized Candida antarctica lipase B-catalyzed esterification of adipic acid and methanol.According to the general procedure described above, Dimethyl adipate has been synthesized from adipic acid (730mg, 5 mmol) and methanol (10 ml). Yield: 9%.1H NMR (400.1 MHz, CDCl3): δ = 3.56 (6H, s, H1-H10), 2.23 (4H, m, H4-H7), 1.56 (4H, m, H5-H6).13C NMR (100.5 MHz, CDCl3): δ = 173.4 (C3-C8), 51.2 (C1-C10), 33.4 (C4-C7), 24.1 (C5-C6)https://pubmed.ncbi.nlm.nih.gov/20632329/
Carcinogenicity
In a chronic inhalation toxicity
study of dimethyl adipate, groups of male and female rats
were exposed to 400 mg/m3 of dimethyl adipate over a
90-day period. Focal respiratory metaplasia of the olfactory
epithelium was found. These nonneoplastic lesions were
minimal to mild in severity .
Precautions
During handling of dimethyl adipate, occupational workers should be careful and use
self-contained breathing apparatus, rubber boots, and heavy rubber gloves and avoid prolonged
period of exposures. Workers should avoid contact of dimethyl adipate with skin,
eyes and nose.
Check Digit Verification of cas no
The CAS Registry Mumber 627-93-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 7 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 627-93:
(5*6)+(4*2)+(3*7)+(2*9)+(1*3)=80
80 % 10 = 0
So 627-93-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H14O4/c1-11-7(9)5-3-4-6-8(10)12-2/h3-6H2,1-2H3
627-93-0Relevant articles and documents
Thomas,Lux
, p. 965 (1972)
Oxidation of cyclohexanone and/or cyclohexanol catalyzed by Dawson-type polyoxometalates using hydrogen peroxide
Dermeche, Leila,Idrissou, Yasmina,Mazari, Tassadit,Moudjahed, Mohammed,Rabia, Cherifa
, (2022/03/07)
The oxidation of cyclohexanone, cyclohexanol or cyclohexanone/cyclohexanol mixture using as catalyst, Dawson-type polyoxometalates (POMs) of formula, α- and β-K6P2W18O62, α-K6P2Mo6W12O62 and α1-K7P2Mo5VW12O62 and hydrogen peroxide, carried out at 90 °C with a reaction time of 20 h, led to a high number of mono- and di-acids which were identified by GC-MS. Levulinic, 6-hydroxyhexanoic, adipic, glutaric and succinic acids, major products were evaluated by HPLC. Regardless of the substrate nature, all POMs exhibited high catalytic activity with 94–99% of conversion, whereas the formation of the different products is sensitively related to both the composition and symmetry of the POMs and the substrate nature. The main products are adipic acid in the presence of α-K6P2Mo6W12O62 and α1-K7P2Mo5VW12O62, levulinic acid in the presence of α1-K7P2Mo5VW12O62 and β-K6P2W18O62 and 6-hydroxyhexanoic acid in the presence of α- and β-K6P2W18O62. Graphical abstract: High catalytic activity was observed with?α- and?β-K6P2W18O62, α-K6P2Mo6W12O62 and α1-K7P2Mo5VW12O62 Dawson-type for the oxidation of cyclohexanone, cyclohexanol or cyclohexanone/cyclohexanol mixture, in the hydrogen peroxide presence, to several oxygenated products. Adipic, levulinic and 6-hydroxyhexanoic acids are the main products. The peroxo- species formed in situ could be the active sites.[Figure not available: see fulltext.]
Efficient Catalysts for the Green Synthesis of Adipic Acid from Biomass
Deng, Weiping,Yan, Longfei,Wang, Binju,Zhang, Qihui,Song, Haiyan,Wang, Shanshan,Zhang, Qinghong,Wang, Ye
supporting information, p. 4712 - 4719 (2021/01/20)
Green synthesis of adipic acid from renewable biomass is a very attractive goal of sustainable chemistry. Herein, we report efficient catalysts for a two-step transformation of cellulose-derived glucose into adipic acid via glucaric acid. Carbon nanotube-supported platinum nanoparticles are found to work efficiently for the oxidation of glucose to glucaric acid. An activated carbon-supported bifunctional catalyst composed of rhenium oxide and palladium is discovered to be powerful for the removal of four hydroxyl groups in glucaric acid, affording adipic acid with a 99 % yield. Rhenium oxide functions for the deoxygenation but is less efficient for four hydroxyl group removal. The co-presence of palladium not only catalyzes the hydrogenation of olefin intermediates but also synergistically facilitates the deoxygenation. This work presents a green route for adipic acid synthesis and offers a bifunctional-catalysis strategy for efficient deoxygenation.
H2-Free Re-Based Catalytic Dehydroxylation of Aldaric Acid to Muconic and Adipic Acid Esters
Ho?evar, Brigita,Pra?nikar, An?e,Hu?, Matej,Grilc, Miha,Likozar, Bla?
, p. 1244 - 1253 (2020/12/09)
As one of the most demanded dicarboxylic acids, adipic acid can be directly produced from renewable sources. Hexoses from (hemi)cellulose are oxidized to aldaric acids and subsequently catalytically dehydroxylated. Hitherto performed homogeneously, we present the first heterogeneous catalytic process for converting an aldaric acid into muconic and adipic acid. The contribution of leached Re from the solid pre-reduced catalyst was also investigated with hot-filtration test and found to be inactive for dehydroxylation. Corrosive or hazardous (HBr/H2) reagents are avoided and simple alcohols and solid Re/C catalysts in an inert atmosphere are used. At 120 °C, the carboxylic groups are protected by esterification, which prevents lactonization in the absence of water or acidic sites. Dehydroxylation and partial hydrogenation yield monohexenoates (93 %). For complete hydrogenation to adipate, a 16 % higher activation barrier necessitates higher temperatures.