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

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

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.

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 
• 108-30-5 succinic acid anhydride 
• 124-04-9 Adipic acid 
• 110-82-7 cyclohexane 
• 96-36-6 methyl phosphite 
• 292638-85-8 acrylic acid methyl ester 
• 186581-53-3 diazomethane 
• 6705-49-3 7-oxabicyclo[4.1.0]heptan-2-one 
• 4316-49-8 exogonic acid 
• 112-63-0 Methyl linoleate 

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 
• 629-11-8 1,6-hexanediol 
• 856348-26-0 1,1,6,6-tetrakis-(3-methoxy-phenyl)-hexane-1,6-diol 
• 628-94-4 adipamide 
• 533-60-8 cyclohexanone-2-ol 
• 10472-24-9 methyl 2-oxocyclopentane-1-carboxylate 
• 62808-73-5 6-oxo-7-phenyl-heptanoic acid 
• 4341-27-9 6,6'-butane-1,4-diyl-bis-[1,3,5]triazine-2,4-diamine 
• 61551-94-8 1,10-diphenyl-decane-1,3,8,10-tetraone 
• 855911-09-0 1,1,6,6-tetrakis-(2-methoxy-phenyl)-hexane-1,6-diol 
• 6838-67-1 1,2-bis(trimethylsilyloxy)cyclohex-1-ene 

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.]

Diphosphine compound, catalyst system containing diphosphine compound and application of diphosphine compound

The present invention provides a diphosphine compound, a catalyst system containing the same, and applications of the diphosphine compound, the diphosphine compound has a structure represented by a formula I or a formula II, a phosphorus atom and a benzene ring are connected through methylene, and a nitrogen-containing heteroaryl structure is matched, such that carbon monoxide can be easily activated after phosphorus and a metal are coordinated, and an alkoxy carbonylation reaction is facilitated. The catalyst system comprises a bimetallic catalyst and the diphosphine compound, and when the catalyst system is used for catalyzing conjugated olefin to prepare 1, 6-dicarboxylic ester compounds, the conversion rate of raw materials can be effectively improved, and the yield and regioselectivity of products are improved.

Efficient Palladium-Catalyzed Carbonylation of 1,3-Dienes: Selective Synthesis of Adipates and Other Aliphatic Diesters

The dicarbonylation of 1,3-butadiene to adipic acid derivatives offers the potential for a more cost-efficient and environmentally benign industrial process. However, the complex reaction network of regioisomeric carbonylation and isomerization pathways, make a selective and direct transformation particularly difficult. Here, we report surprising solvent effects on this palladium-catalysed process in the presence of 1,2-bis-di-tert-butylphosphin-oxylene (dtbpx) ligands, which allow adipate diester formation from 1,3-butadiene, carbon monoxide, and methanol with 97 % selectivity and 100 % atom-economy under scalable conditions. Under optimal conditions a variety of di- and triesters from 1,2- and 1,3-dienes can be obtained in good to excellent yields.

Biomass-derived dibasic acids to diesters with inorganic ligand-supported catalyst: synthesis, optimization, characterization

Several attempts have been made to obtain aliphatic dicarboxylic diesters from esterification reaction to develop the biomass-derived platform molecules and green manufacturing processes. In this paper, Na3(H2O)6[AlMo6O18(OH)6], an Anderson-type polyoxometalate, firstly, was reported as a catalyst for diester synthesis from dicarboxylic acid to diester which showed an well productivity and selectivity characterized by 1H and 13C. Response surface methodology (RSM) integrated with the desirability function approach was used to determine the best operative conditions, and the optimal reaction parameters for maximum dipropyl succinate yield (77 ± 2.5%) were identified as 1.19?mol.% catalyst loading, 4.9:1 propanol/succinic acid ratio, 113?°C, and 9.6?h. Three batches of tests were carried for catalyst recycling with 78–75% yield even after 6 cycles of esterification. In addition, the substrate carbon chain was increased for investigation of substrate scope achieving satisfactory results and all products were characterized by 1H and 13C nuclear magnetic resonance spectroscopy.

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.

Ruthenium-catalysed oxidative coupling of vinyl derivatives and application in tandem hydrogenation

The first ruthenium-catalyzed oxidative homo- and cross-coupling of exclusive vinyl derivatives giving highly valued 1,3-diene building blocks is reported. The catalytic system is based on readily available reagents and it mainly delivers the E,E isomer. This methodology also enables the synthesis of adipic acid ester derivatives in a one-pot fashion after in situ ruthenium-catalyzed hydrogenation.

A general platinum-catalyzed alkoxycarbonylation of olefins

Hydroxy- and alkoxycarbonylation reactions constitute important industrial processes in homogeneous catalysis. Nowadays, palladium complexes constitute state-of-the-art catalysts for these transformations. Herein, we report the first efficient platinum-catalysed alkoxycarbonylations of olefins including sterically hindered and functionalized ones. This atom-efficient catalytic transformation provides straightforward access to a variety of valuable esters in good to excellent yields and often with high selectivities. In kinetic experiments the activities of Pd- and Pt-based catalysts were compared. Even at low catalyst loading, Pt shows high catalytic activity.

NOVEL ESTERIFICATION CATALYST AND USES THEREOF

Tin (II) glucarate is found to be effective alone and in combination with other tin compounds for catalyzing the reaction of carboxylic acids such as furan-2,5-dicarboxylic acid, terephthalic acid and adipic acid with alcohols such as the C1-C3 alcohols.

Ultralow-Molecular-Weight Stimuli-Responsive and Multifunctional Supramolecular Gels Based on Monomers and Trimers of Hydrazides

The simpler, the better. A series of simple, neutral and ultralow-molecular-weight (MW: 140–200) hydrazide-derived supramolecular gelators have been designed and synthesized in two straightforward steps. For non-conjugated cyclohexane-derived hydrazides, their monomers can self-assemble to form gels through intermolecular hydrogen bonds and dipole-dipole interactions. Significantly, conjugated phthalhydrazide can self-aggregate into planar and circular trimers through intermolecular hydrogen bonds and then self-assemble to form gels through intermolecular π–π stacking interactions. It is interesting that these simple gelators exhibit unusual properties, such as self-healing, multi-response fluorescence, and visual and selective recognition of chiral (R)/(S)-1,1′-binaphthalene-2,2′-diamine and S2? through much different times of gel re-formation and blue-green color change, respectively. These results underline the importance of supramolecular gels and extend the scope of supramolecular gelators.