627-93-0

Basic information

• Product Name: Dimethyl adipate
• Synonyms: Dimethylhexaneo-lionate;hexadioic acid, dimethyl ester;Dimethyl hexanedionate ;DIMETHYL ADIPATE, 99+%;Dimethyl Adipate-13C6;DIBASICESTERS;Dimethyladipat;HEXANEDIOICACID,DIMETHYLEST
• CAS NO: 627-93-0
• Molecular Formula: C₈H₁₄O₄
• Molecular Weight: 174.19
• EINECS: 211-020-6
• Product Categories: Fatty Acid Esters (Plasticizer);Functional Materials;Plasticizer;Ester series;C8 to C9;Carbonyl Compounds;Esters;Plasticizers;Polymer Additives;Polymer Science;solvent
• Mol File: 627-93-0.mol
• Article Data: 153

Chemical Properties

• Melting Point: 8 °C(lit.)
• Boiling Point: 109-110 °C14 mm Hg(lit.)
• Flash Point: 225 °F
• Appearance: Clear/Liquid
• Density: 1.062 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.2 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.428(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: <1g/l
• Explosive Limit: 0.81-8.1%(V)
• Water Solubility: Miscible with alcohols and ether. Immiscible with water.
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, acids, bases reducing agents.
• Merck: 14,162
• BRN: 1707443
• CAS DataBase Reference: Dimethyl adipate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl adipate(627-93-0)
• EPA Substance Registry System: Dimethyl adipate(627-93-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 1
• RTECS: AV1645000
• TSCA: Yes
• Hazardous Substances Data: 627-93-0(Hazardous Substances Data)

Usage

Description

Dimethyl adipate (DMA) is a colourless and flammable liquid. It is soluble in alcohol and ether but sparingly soluble in water. DMA is incompatible with strong oxidising agents, and on decomposition, it emits carbon monoxide, irritating and toxic fumes and gases, and carbon dioxide. DMA reacts with acids, alkalis, and strong oxidants. DMA is synthesised by the esterification of adipic acid. DMA is part of a dibasic ester (DBE) blend used as a major ingredient in several paint strippers, and the DBE blends used in paint stripping formulations contain a major portion (about 90%) of DMA. DMA is used as a chemical intermediate (polymers, agrochemicals), cellulose resins, a speciality solvent (inks, coatings, adhesives), and an emollient and can also be utilised as a paint remover and plasticiser.

Chemical Properties

Dimethyl adipate is a colorless liquid. It is a fatty acid methyl ester.

Uses

Different sources of media describe the Uses of 627-93-0 differently. You can refer to the following data:
1. Dimethyl adipate is used in cosmetics (in emollients and skin conditioning).It is used as a plasticizer for cellulose-type resins and a finish remover.It is also used in agrochemicals and dye as well as a precursor for the preparation of active pharmaceutical ingredients. Further, it serves as a polymer intermediate. In addition to this, it is employed as a solvent for paint stripping and resins.
2. Dimethyl adipate is used in cosmetics (in emollients and skin conditioning). It acts as a cosmetic plasticizer. It is also used in agrochemicals and dye as well as a precursor for the preparation of active pharmaceutical ingredients. Further, it serves as a polymer intermediate. In addition to this, it is employed as a solvent for paint stripping and resins.

Production Methods

Dimethyl adipate is manufactured via esterification of adipic acid and methanol in the presence of an acid catalyst.

General Description

Colorless liquid.

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.

InChI:InChI=1/C8H14O4/c1-11-7(9)5-3-4-6-8(10)12-2/h3-6H2,1-2H3

Upstream product

• 110-86-1 pyridine 
• 67-56-1 methanol 
• 3878-55-5 methyl hydrogen succinate 
• 54322-10-0 glutaric acid monobenzyl ester 
• 124-41-4 sodium methylate 
• 629-11-8 1,6-hexanediol 
• 6654-36-0 methyl 6-oxohexanoate 
• 1445-45-0 Trimethyl orthoacetate 
• 124-04-9 Adipic acid 
• 3242-56-6 2-diazocyclohexanone 
• 110-83-8 cyclohexene 
• 627-91-8 adipic acid monomethyl ester 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 186581-53-3 diazomethane 

Downstream Products

• 30196-39-5 2,3-dioxo-cyclohexane-1,4-dicarboxylic acid dimethyl ester 
• 65170-34-5 BAHA 
• 65169-69-9 adipic acid bis-(2-dimethylamino-ethyl ester) 
• 627-91-8 adipic acid monomethyl ester 
• 62808-73-5 6-oxo-7-phenyl-heptanoic acid 
• 6838-67-1 1,2-bis(trimethylsilyloxy)cyclohex-1-ene 
• 105064-45-7 2-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-hexanedioic acid 1-methyl ester 
• 105064-49-1 2-[1-(3-Chloro-phenyl)-meth-(E)-ylidene]-hexanedioic acid 1-methyl ester 
• 105064-47-9 2-[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-hexanedioic acid 1-methyl ester 
• 105064-48-0 2-[1-(2-Bromo-phenyl)-meth-(E)-ylidene]-hexanedioic acid 1-methyl ester 
• 332887-47-5 methyl 7-phenylsulfinyl-6-oxo-heptanoate 
• 1445-91-6 (S)-1-phenylethanol 
• 143394-10-9 (S,S)-α,α'-dimethyl-1,4-benzenedimethanol 
• 118207-34-4 2-(pyrrolidin-1-yl)cyclohexanone 

Relevant articles and documents

Oxidation of cyclohexanone and/or cyclohexanol catalyzed by Dawson-type polyoxometalates using hydrogen peroxide

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

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

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.