1119-40-0

Basic information

• Product Name: Methyl glutarate
• Synonyms: DBE-2;DIMETHYLE GLUTARATE;DBE-5 DIBASIC ESTER, 98% (DIMETHYL GLUTA RATE);DBE-2 DIBASIC ESTER (MIXTURE OF DIMETHY&;DibasicEsterDimethylGlutarate;Dimethylglutarat;PENTANEDIOICACID,DIMETHYLES;Dimethyl glutarate, Glutaric acid dimethyl ester
• CAS NO: 1119-40-0
• Molecular Formula: C₇H₁₂O₄
• Molecular Weight: 160.17
• EINECS: 214-277-2
• Mol File: 1119-40-0.mol

Chemical Properties

• Melting Point: −13 °C(lit.)
• Boiling Point: 96-103 °C15 mm Hg(lit.)
• Flash Point: 218 °F
• Appearance: Clear colorless/Liquid
• Density: 1.09 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.2 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.424(lit.)
• Storage Temp.: 2-8°C
• Solubility: 4.3g/l
• Explosive Limit: 0.9-7.9%(V)
• Water Solubility: 53 g/L
• Stability: Stable. Combustible. Incompatible with acids, bases, reducing agents, oxidizing agents.
• Merck: 14,4473
• BRN: 1771444
• CAS DataBase Reference: Methyl glutarate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl glutarate(1119-40-0)
• EPA Substance Registry System: Methyl glutarate(1119-40-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 1
• TSCA: Yes
• Hazardous Substances Data: 1119-40-0(Hazardous Substances Data)

Usage

Uses

Used in Industrial Applications:
Dimethyl glutarate is used as an intermediate and solvent in the packing and formulation of mixtures and substances. It serves as an intermediate in the manufacture of cleaning agents, lubricants, coating agents, rolling oils, metal working fluids, and blowing agents. Additionally, it is utilized in laboratories, polymer processing, water treatment chemicals, and rubber production and processing.
Used in Professional Work Applications:
In gas and oil field production and drilling operations, dimethyl glutarate is employed for its various applications. It is also used in de-icing and anti-icing applications, construction and road applications, and as a release and binder agent.
Used in Consumer Applications:
The compound finds use in the production of agrochemicals and water treatment chemicals. It is also applied as paint and graffiti removers, nail polish removers, hand cleaners, adhesives, sealants and caulks, automotive cleaning products, bathroom and tile cleaners, general purpose cleaners, spot removers, and floor maintenance products.

Synthesis Reference(s)

Synthesis, p. 555, 1985 DOI: 10.1055/s-1985-31275

Air & Water Reactions

Flammable. Hydrolyzed by strong mineral acids and strong alkalis.

Reactivity Profile

Glutaric acid dimethyl ester 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.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C10H11NO/c1-7-8-5-6-11-9(8)3-4-10(7)12-2/h3-6,11H,1-2H3

Upstream product

• 67-56-1 methanol 
• 110-94-1 1,5-pentanedioic acid 
• 826-34-6 dimethyl cis-cyclopropane-1,2-dicarboxylate 
• 826-35-7 dimethyl trans-1,2-cyclopropanedicarboxylate 
• 5009-28-9 cyclopropanone methyl hemiacetal 
• 107-13-1 acrylonitrile 
• 186581-53-3 diazomethane 
• 6705-49-3 7-oxabicyclo[4.1.0]heptan-2-one 
• 112-63-0 Methyl linoleate 
• 1501-26-4 methyl 4-(chlorocarbonyl)butyrate 
• 930-29-0 1-chlorocyclopent-1-ene 
• 123775-25-7 1-Chlor-5-methyl-6,7,8-trioxabicyclo<3.2.1>octan 
• 123775-23-5 1,5-Dichlor-6,7,8-trioxabicyclo<3.2.1>octan 
• 108-55-4 glutaric anhydride, 

Downstream Products

• 1501-27-5 Pentanedioic acid, monomethyl ester 
• 101789-61-1 methyl 5,5-diphenyl-4-pentenoate 
• 90466-96-9 1,5,5-triphenyl-4-penten-1-one 
• 1070-62-8 5-ethoxy-5-oxopentanoic acid 
• 99440-98-9 2-hydroxycyclopentanone 
• 28569-95-1 2-(4-Carbomethoxybutyryl)cyclohexane 
• 158727-08-3 1,1,5,5-tetraphenyl-pentane-1,5-diol 
• 7147-66-2 2,2'-(1,3-propanediyl)bis(1H-benzimidazole) 
• 29238-07-1 Methyl-4-methoxycarbonyloctadecanoat 
• 17797-67-0 α-(3-Methoxybenzoyl)-glutarsaeure-dimethylester 
• 1508-67-4 glutaric dihydrazide 
• 13424-80-1 N,N,N′,N′-tetramethylglutaramide 
• 33446-28-5 6-(p-tolyl)-heptan-2,6-diol 
• 142-68-7 TETRAHYDROPYRANE 

Relevant articles and documents

Synthesis of α,ω-dicarboxylic acid dimethyl esters from cycloalkanones

Reaction of cycloalkanones with [hydroxy(2,4-dinitrobenzenesulfonyloxy)iodo]benzene and subsequent treatment of α-[(2,4-dinitrobenzene)sulfonyl]oxy cycloalkanone intermediates with Oxone and PTSA in MeOH-H2O (6:1, v/v) solution provided dicarboxylic acid dimethyl esters in high yields.

Straightforward synthesis of functionalized (E)-3-acylacrylic acids

An experimentally simple, mild and straightforward synthetic route towards diversely functionalized (E)-3-acylacrylic acids is described, with Horner-Wadsworth-Emmons (HWE) reaction as the key step. The substrate scope and limitations of the HWE reaction were investigated with a range of β-ketophosphonates. Glyoxylic acid monohydrate was demonstrated to be fully compatible with the HWE reaction conditions, thus avoiding a troublesome hydrolysis of the corresponding 3-acylacrylates in the last step and providing a valuable synthetic shortcut.

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.

Sulfonic acid-functionalized organic knitted porous polyaromatic microspheres as heterogeneous catalysts for biodiesel production

The use of renewable energy sources decreases the consequences of greenhouse gas emission from fossil fuels. Biodiesel, an easily burning and biodegradable fuel, is an alternative to conventional diesel fuel. The esterification of long-chain fatty acids and transesterification of triglycerides are two major reactions widely used to convert vegetable oils or animal fats into biodiesel. As solid acid catalysts are considered promising candidates for biodiesel production, we have synthesized a series of organic knitted porous polyaromatics (OPPs) using pyrene, anthracene, and naphthalene as monomers via Friedel-Crafts alkylation, followed by crosslinking reactions. The resultant polymers showed good surface morphology, stability and swelling property, high capacity for functionalization due to the unreacted bromomethyl groups on the surface, and excellent hydrophobicity. The sulfonated polymer microspheres obtained by the surface sulfonation showed good surface acidity; thus, they can be employed as heterogeneous solid acid catalysts for the esterification of long-chain fatty acids and transesterification of triglycerides, and they are reusable without any leaching of functional groups.

Palladium-catalyzed selective generation of CO from formic acid for carbonylation of alkenes

A general and selective palladium-catalyzed alkoxycarbonylation of all kinds of alkenes with formic acid (HCOOH, FA) is described. Terminal, di-, tri-, and tetra-substituted including functionalized olefins are converted into linear esters with high yields and regioselectivity. Key-to-success is the use of specific palladium catalysts containing ligands with built-in base, e.g., L5. Comparison experiments demonstrate that the active catalyst system not only facilitates isomerization and carbonylation of alkenes but also promotes the selective decomposition of HCOOH to CO under mild conditions.

Efficient and selective oxidation of aldehydes with dioxygen catalysed by vanadium-containing heteropolyanions

The heteropolyacids “H3+n[PMo12–nVnO40]·aq” (denoted as HPA-n; n = 2, 3, 8) catalyse the oxidation of aldehydes to carboxylic acids in the presence of dioxygen with very good yields. The effect on the catalytic activity of various parameters such as the precursors, solvent, temperature or catalyst/substrate ratio was examined. The process is particularly selective for linear and aromatic aldehydes. The oxidation of adipaldehyde with dioxygen in mild conditions, in the presence of HPA-2 as a catalyst, leads to the formation of adipic acid together with a significant amount of other byproducts. Thus, several modifications of the catalytic systems have been carried out to improve their selectivity. The effect of cocatalysts was investigated and, among the species tested, complex Ni(acac)2 was found to be the most efficient yielding 60% of adipic acid.

Metal-catalyzed reductive deamination of glutamic acid to bio-based dimethyl glutarate and methylamines

Glutamic acid is a promising renewable platform molecule which is abundantly available in biomass waste streams; it is also efficiently manufactured by fermentation. Here we report the reductive deamination of glutamic acid to bio-based dimethyl glutarate and methylamines. In order to recycle nitrogen in an industrially relevant co-product, glutamic acid was modified to N,N-dimethylglutamic acid by a mild reductive alkylation with Pd/C. Subsequently, selective C-N hydrogenolysis in methanol resulted in dimethyl glutarate and trimethylamine. A wide screening of transition metals (Pt, Pd, Rh and Ru) immobilized on various supports showed that the highest yields of dimethyl glutarate were obtained with Pt/TiO2. An FTIR study and kinetic experiments on metal-loaded and unloaded supports demonstrate that the interplay between the metal and the moderate acidity of the support results in the excellent C-N hydrogenolysis activity and selectivity. Finally, reaction parameter optimization resulted in 81% yield of dimethyl glutarate with 1 wt% Pt/TiO2 at 225 °C, 30 bar H2 after 8 h.

PROCESS FOR DOUBLE CARBONYLATION OF ALLYL ETHERS TO CORRESPONDING DIESTERS

The invention relates to a process for doubly carbonylating allyl ethers to the corresponding diesters, wherein a linear or branched allyl ether is reacted with a linear or branched alkanol (alcohol) with supply of CO and in the presence of a catalytic system composed of a palladium complex and at least one organic phosphorus ligand and in the presence of a hydrogen halide selected from HCl, HBr and HI.

Methylation of mono- and dicarboxylic acids with dimethyl carbonate catalyzed with binder-free zeolite NaY

Synthesis of methyl mono- and dicarboxylates was developed consisting in treating the corresponding acids with dimethyl carbonate in the presence of a heterogenic catalyst, crystalline aluminosilicate whose mechanically strong granules to 90–95% were built of crystal aggregates of zeolite Y with modulus of about 5.0 in the Na-form. Optimum catalyst and reagents ratio and the reaction conditions were found for the preparation in high yields of methyl esters of mono- and dicarboxylic acids.

PROCESS FOR DOUBLE CARBONYLATION OF ALLYL ALCOHOLS TO CORRESPONDING DIESTERS

The invention relates to a process for doubly carbonylating allyl alcohols to the corresponding diesters, wherein a linear or branched allyl alcohol is reacted with a linear or branched alkanol (alcohol) with supply of CO and in the presence of a catalytic system composed of a palladium complex and at least one organic phosphorus ligand and in the presence of a hydrogen halide selected from HCl, HBr and HI.