Glycol ether esters manufacture

About 130 years after the 1795 discovery of ethylene [2, 3], the lower olefins became important intermediates for manufacturing many industrial chemicals, including glycol, glycol mono- and di-esters, glycol mono- and di-ethers, glycol ether esters, polyethylene glycols, ethanolamines, and morpholine [2, 5]. 

Process Raw Material. Industrial solvents are raw materials in some production processes. Eor example, only a small proportion of acetone is used as a solvent, most is used in producing methyl methacrylate and bisphenol A. Alcohols are used in the manufacture of esters and glycol ethers. Diethylenetriamine is also used in the manufacture of curing agents for epoxy resins. Traditionally, chlorinated hydrocarbon solvents have been the starting materials for duorinated hydrocarbon production. 

VOCs found in water-based paints in the Netherlands and Denmark (by a survey of manufacturers) are presented in Table 16.3. VOC emission assessments have shown that most of these VOCs are emitted from water-based paints, though with significant variation from product to product in type and quantity of VOC emitted. For example, Table 16.4 presents the VOC emissions from wet products under identical test conditions (Brown, 2000). WBP1 has no 1,2-propylene glycol while the other paints all use large quantities, apparently replacing the glycol ethers and esters. 

OTHER COMMENTS used as a solvent for fats, waxes, resins, shellac, varnish, gums, etc. used in the preparation of esters, especially butyl acetate used in the manufacture of hydraulic fluids and detergent formulations also used as an azeotropic dehydrating agent chemical intermediate for butylamines, glycol ethers, and butyl acrylate used as an extractant in the manufacture of antibiotics, vitamins, and hormones. 

The active surfactant in a fabric softener is an ester quat (quaternary ammonium compound with ester links to improve biodegradability). These active ingredients are supplied to the product manufacturers as a mobile liquid which contains isopropanol. Other solvents, such as glycol ethers, can be used but, mainly for cost reasons, over 90% of the market uses isopropanol. 

Other applications that utilize glycol ethers include adhesives, leather dyes, jet fuel anti-icing additive, rosin soldering flux solvent, mineral oil dewaxing, safety glass manufacture, and as chemical intermediates in the production of ester-type chemicals. 

CH3 CH0H CH20H, a colourless, almost odourless liquid. It has a sweet taste, but is more acrid than ethylene glycol b.p. 187. Manufactured by heating propylene chlorohydrin with a solution of NaHCO under pressure. It closely resembles dihydroxyethane in its properties, but is less toxic. Forms mono-and di-esters and ethers. Used as an anti-freeze and in the preparation of perfumes and flavouring extracts, as a solvent and in... 

Although synthetic lubrication oil production amounts to only about 2% of the total market, volume has been increasing rapidly (67). Growth rates of the order of 20% per year for poly( a-olefin)s, 10% for polybutenes, and 8% for esters (28) reflect increasing automotive use and these increases would accelerate if synthetics were adopted for factory fill of engines by automotive manufacturers. The estimated production of poly( a-olefin)s for lubricants appears to be approximately 100,000 m /yr, esters 75,000, poly(alkylene glycol)s 42,000, polybutenes 38,000, phosphates 20,000, and dialkyl benzene 18,000 (28,67). The higher costs reflected in Table 18 (18,28) have restricted the volume of siUcones, chlorotrifluoroethylene, perfluoroalkylpolyethers, and polyphenyl ethers. 

Ahyl alcohol undergoes reactions typical of saturated, aUphatic alcohols. Ahyl compounds derived from ahyl alcohol and used industriahy, are widely manufactured by these reactions. For example, reactions of ahyl alcohol with acid anhydrides, esters, and acid chlorides yield ahyl esters, such as diahyl phthalates and ahyl methacrylate reaction with chloroformate yields carbonates, such as diethylene glycol bis(ahyl carbonate) addition of ahyl alcohol to epoxy groups yields products used to produce ahyl glycidyl ether (33,34). 

Ethanol s many uses can be conveniently divided into solvent and chemical uses. As a solvent, ethanol dissolves many organic-based materials such as fats, oils, and hydrocarbons. As a chemical intermediate, ethanol is a precursor for acetaldehyde, acetic acid, and diethyl ether, and it is used in the manufacture of glycol ethyl ethers, ethylamines, and many ethyl esters. 

FORMAMIDE. Form amide (meibanamide), HCONHi. is the lirsi member of the primary amide series and is the only one liquid at room temperature. II is hygroscopic and has a faint odor of ammonia. Formamide is a colorless to pale yellowish liquid, freely miscible with water, lower alcohols and glycols, and lower esters and acetone. It is virtually immiscible in almost all aliphatic and aromatic hydrocarbons, chlorinated hydrocarbons, and ethers. By virtue of its high dielectric constant, close to that of water and unusual for an organic compound, formamide has a high solvent capacity lor many heavy-metal salts and for salts of alkali and alkalinc-carth metals. It is an important solvent, in particular for resins and plasticizers. As a chemical intermediate, formamide is especially useful in the synthesis of heterocyclic compounds, pharmaceuticals, crop protection agents, pesticides, and for the manufacture of hydrocyanic acid. 

Abstract The chemical nature and technology of the main synthetic lubricant base fluids is described, covering polyalphaolefins, alkylated aromatics, gas-to-liquid (GTL) base fluids, polybutenes, aliphatic diesters, polyolesters, polyalkylene glycols or PAGs and phosphate esters. Other synthetic lubricant base oils such as the silicones, borate esters, perfluoroethers and polyphenylene ethers are considered to have restricted applications due to either high cost or performance limitations and are not considered here. Each of the main synthetic base fluids is described for their chemical and physical properties, manufacture and production, their chemistry, key properties, applications and their implications when used in the environment. 

Tables 14.22.1 and 14.22.2 provide data on releases and transfers from both polymer manufaeturing and man-made fiber produetion in flie USA. Carbon disulfide, methanol, xylene, and ethylene glycol are used in the largest quantities. Carbon disulfide is used in manufacture of regenerated cellulose and rayon. Efliylene glycol is used in the manufacture of polyethylene terephthalate, the manufacture of aUcyd resins, and as cosolvent for cellulose ethers and esters. Methanol is used in several processes, the largest being in the production of polyester. This industry is the 10th largest contributor of VOC and 7th largest in releases and transfers.

There is a series of polymers having a chemical structure — [(CHR) —O— which are derived as polyacetal resins, and are known as polyalkyene oxides or polyalkylene glycols. In the above structure, the polymer with R=H and M = 1 is polyoxymethylene, which is known as Delrin. This material is a high polymer of formaldehyde, which is terminated by an ether or ester function added to stabilize the final product. Other manufactured products include copolymers with ethylene oxide or propylene oxide. The IR and Raman spectra of polyoxymethylene are shown in Reference Spectrum 55. A strong peak at 1098 cm and a doublet at 936 and 900 cm in the IR spectrum are assigned to the C—O—C stretching vibration. It is not possible to determine if the sample is a homopolymer or copolymer from this spectrum. 

---