Ethylene glycol, from methanol

The DuPont process (the oldest syngas process to produce ethylene glycol) reacts formaldehyde with CO in the presence of a strong mineral acid. The intermediate is glycolic acid, which is esterified with methanol. The ester is then hydrogenated to ethylene glycol and methanol, which is recovered. The net reaction from either process could he represented as ... 

A new route to ethylene glycol from ethylene oxide via the intermediate formation of ethylene carbonate has recently been developed by Texaco. Ethylene carbonate may be formed by the reaction of carbon monoxide, ethylene oxide, and oxygen. Alternatively, it could be obtained by the reaction of phosgene and methanol. 

Consumption of small amounts of antifreeze can be deadly. Poisonous constituents are typically ethylene glycol and methanol. There is no home treatment aside from standard first-aid and cardiopulmonary resuscitation (CPR) for signs of shock or cardiac arrest. Gastric treatment and dialysis may be immediately necessary for survival depending on the dose, and long-term kidney and brain damage are possible. 

Fig. 4. Dielectric constant (D) of hydroorganic solvents as a function of percentage in volume. DMSO, dimethyl sulfoxide EGOH, ethylene glycol MeOH, methanol PrOH, propylene glycol MPD, 2-methyl-2,4-pentanediol. Temperature, 20°C. From Douzou (1977b). Reprinted with permission of Academic Press.

Fig. 13. Proton activity of buffered solutions in water (30%)-ethylene glycol (10%)-methanol (60%) as a function of temperature. The number on each curve indicates pH value in pure water. From Travers et al. (1975). Reprinted with permission of Biochimie. Copyright by the Societe de Chimie Biologique.

The apparent acid dissociation constants (p s)Ka) of two water-insoluble drugs, ibuprofen and quinine, were determined pH-metrically in ACN water, dimethyl-formamide water, DMSO water, 1,4-dioxane-water, ethanol water, ethylene glycol-water, methanol water, and tetrahydrofuran water mixtures. A glass electrode calibration procedure based on a four-parameter equation (pH = alpha-i- SpcH -i-jH[H+] -i-jOH[OH ]) was used to obtain pH readings based on the concentration scale (pcH). We have called this four-parameter method the Four-Plus technique. The Yasuda Shedlovsky extrapolation p s)K a + log [H2O] = A/epsllon -1- B) was used to derive acid dissociation constants in aqueous solution (pKa). It has been demonstrated that the pK a values extrapolated from such solvent-water mixtures are consistent with each other and with previously reported measurements. The suggested method has also been applied with success to determine the pKa values of two pyridine derivatives of pharmaceutical Interest. Spectrometric, ultraviolet (UV) ... 

Fig. 4. Permeability of human red blood cell membranes to non-electrolytes in relation to ether/water partition coefficients. Ordinate permeability on a logarithmic scale, in units of mol/dyne/s. Abscissa partition coefficients tor the ether/water system. Data measured at room temperature (20 to 21 °C). Permeants are numbered as follows 1, water 2. formamide 3, acetamide 4, propionamide 5, butyramide 6, obutyramide 7, valcramide 8, /sovaleramide 9, urea 10, methylurea 11, (1,3)-dimethylurea 12, (l,3)-propandiol 13, (l,4)-butandiol 14, (l,3)-butandiol 15, (2,3)-butandiol 16, ethylene glycol 17, methanol 18, malonamide A, acetic acid B, butyric acid F, formic acid P, propionic acid V, valeric acid. Data from Savitz and Solomon [12] tor permeants 2, 9, 16, and 17 from Kocke et al. [13] for A througli V from Sha afi et al. [11] for all others.

Fig. 3 Comparison of the catalytic the performances in the glycerol hydrogenolysis over modified Rh/Si02 [33]. Reaction conditions glycerol 4 g, water 16 g, Rh-M0 j/Si02 (M/Rh = 0.25) 0.15 g, F(H2) = 8 MPa, r = 393 K, / = 5 h. Re/Rh = 0.5, r = 1 h. PrD propanediol, PrOH propanol. Degradation ethylene glycol + ethanol + methanol + methane. Reprinted with permission from...

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