Ethylene glycol bicarbonate

Ethylene glycol was originally commercially produced in the United States from ethylene chlorohydrin [107-07-3J, which was manufactured from ethylene and hypochlorous acid (eq. 8) (see Chlorohydrins). Chlorohydrin can be converted direcdy to ethylene glycol by hydrolysis with a base, generally caustic or caustic/bicarbonate mix (eq. 9). An alternative production method is converting chlorohydrin to ethylene oxide (eq. 10) with subsequent hydrolysis (eq. 11). 

Bisethylenedioxypregn-5-ene. Method A. A mixture of progesterone (10 g), freshly distilled ethylene glycol (80 ml) and benzene (350 ml) is slowly distilled for 15 min to remove traces of water. p-Toluenesulfonic acid monohydrate (0.3 g) is added and the mixture is heated under reflux with stirring for 5 hr with a water separator. Saturated sodium bicarbonate solution is added to the cooled mixture and the benzene layer is separated. The organic layer is washed twice with water, dried and evaporated in vacuo. The residue is crystallized twice from acetone-methanol to give 4.15 g (32%) of bisketal, mp 178-181°. 

Ji-Methoxy-ll, 11-ethylenedioxy-lS-methylestra-1,3,5(lO)-tnene. A solution of (+)3-methoxy-18-methylestra-l,3,5(10)-trien-17-one (5 g) dissolved in ethylene glycol (5 ml) and ethyl orthoformate (10 ml) containing />-toluenesulfonic acid (0.3 g) is heated under reflux for 2 hr in a nitrogen atmosphere. The resulting solution is diluted with methylene chloride and washed with dilute sodium bicarbonate and water. The organic phase is dried over sodium sulfate and evaporated to dryness in the presence of a trace of pyridine. Trituration of the residue with petroleum ether yields 4.7 g (82 %) of the pure ketal. 

Ethylene glycol is made by reacting chlorohydrin with sodium bicarbonate,... 

Chemical/Physical. Reacts with aqueous sodium bicarbonate solutions at 105 °C producing ethylene glycol (Patnaik, 1992). 

Management of methanol and ethylene glycol poisoning is similar. Symptomatic support of respiration and circulation is augmented by correction of metabolic acidosis with intravenous bicarbonate infusion, and control of seizures with diazepam. Ethanol inhibits the metabolism of methanol and ethylene glycol to the toxic metabolites, and can give time for further treatment. The goal is to maintain blood ethanol concentrations between 100 and 150 mg per decilitre, sufficient to saturate alcohol... 

For patients who have ingested more than 30 ml of (pure) methanol or ethylene glycol, dialysis is recommended, and haemodialysis is more effective than peritoneal dialysis. Dialysis both removes the alcohols and their metabolites, and corrects the renal and metabolic disturbances and so is the preferred treatment in severe poisoning. The maintenance dose of ethanol required may be tripled during haemodialysis as ethanol is also removed. Early treatment is indicated if ethylene glycol concentrations are above 20 mg/100 ml (200 mg/1), if the arterial pH is below 7.3, if serum bicarbonate concentrations are less than 20 mM/1, and when there are oxalate crystals in the urine. 

Benzene, Arsenic trichloride, Aluminum chloride. Hexanes Acetic anhydride. Nitric acid, Hexamine, Acetic acid, Methylene chloride. Sodium bicarbonate, Magnesium sulfate, Dioxane, Hydrogen chloride, Acetone, Sodium azide m-phenylenediamine, Methanol, Sodium carbonate, Ethyl chloromate, Ethylene glycol dimethyl ether, Sulfuric acid, Nitric acid... 

A mixture of 11.8 g of (+/-)-3a,6,7,7a-tetrahydro-4-methyl-2-oxo-ip-indaheptanoic acid methyl ester, 27 ml of ethylene glycol and 300 mg of p-toluene sulfonic acid mono-hydrate in 600 ml of benzene was refluxed with stirring for 18 hours using a Dean-Stark trap to separate the water formed in the reaction. The reaction mixture was cooled and added to 300 ml of cold 5% potassium bicarbonate. The aqueous layer extracted twice with 2 1 benzene-hexene. The combined organic fractions were washed 3 times with saturated aqueous NaCI, dried over sodium sulfate and evaporated to dryness... 

A solution of 0.144 g of the 3-ethylene glycol ketal of 5a,lip,17a,21 -tetrahydroxy-6p-fluoro-16a-methylallopregnane-3,20-dione-21 acetate in 12 ml of chloroform and 0.1 ml of absolute alcohol was cooled to -10°C in an ice-salt bath and a stream of anhydrous hydrochloric acid was gently bubbled through the solution for 2.5 hours while the temperature was maintained between -5°C and -15°C. The solution was then diluted with 25 ml of chloroform, washed with dilute sodium bicarbonate and water, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure at 60°C or less to give 6a-fluoro-lip,17a,21-trihydroxy-16a-methyl-4-pregnene-3,20-dione 21-acetate. 

In addition, because one of the effects of ethylene glycol is to cause the blood and tissues to become more acidic, treatment also involves giving the patient an intravenous infusion of bicarbonate of soda (sodium... 

Fortunately, treatment is possible, using alcohol (that is, ethyl alcohol), the same treatment as for ethylene glycol poisoning. The acidity is also treated with bicarbonate of soda. Methyl alcohol is eliminated from the body slowly, and so repeated intake, as in those who drink meths, could lead to cumulative poisoning. 

Modifications are made also in order to use this reaction to conjugate nucleosides to erythrocyte surfaces, allowing use of the coated cells as targets for assays of antibody-forming splenic lymphocytes. Nucleoside, 10-20 mg, is oxidized in 1.5 ml of 0.1 M sodium periodate in 0.15M NaHCOa for 20 min at room temperature the reaction is stopped by the addition of 15 /zl of ethylene glycol. Sheep erythrocytes are washed twice with 0.15 M NaHCOs, and 0.5 ml of packed cells is then suspended in 2.0 ml of the bicarbonate solution in a40-ml centrifuge tube. The oxidized nucleoside is added dropwise to the cell suspension and the mixture is kept at room temperature for 15 min. fert-Butylamine borane (Aldrich Chemical Co.), 100 mg in 5 ml of 0.15 M NaHCOs, is added. The suspension is kept at room temperature for 3 min, and the tube is then quickly filled with bicarbonate solution and centrifuged at 1500 rpm for 10 min. 

Treatment of ethylene glycol toxicity is with ethanol, which inhibits alcohol dehydrogenase, fomepizole, which also inhibits alcohol dehydrogenase, and bicarbonate to treat acidosis (33). In some cases hemodialysis has been used (34,35). 

Treatment should include correction of metabolic acidosis, inhibition of ethylene glycol metabolism and if necessary, extracorporeal elimination of the parent alcohol and metabolites. Acidemia likely increases tissue penetration of toxic metabolites and hinders renal clearance. Although evidence is lacking, bicarbonate administration should be given to correct acidemia. Although more expensive, fomepizole is preferred to ethanol for ADH inhibition due to proven efficacy, predictable pharmacokinetics, and lack of adverse effects [105]. Inhibition of ADH with fomepizole prevents formation of toxic metabolites and renal injury, and improves add-base status [106]. Elimination half-life of ethylene glycol with fomepizole in patients with preserved renal function is approximately 20 hours [107]. Pyridoxine and thiamine should be administered to promote glyoxyhc add conversion less toxic metabolites than oxalate [108]. 

In the conditions discussed above (diabetic ketoacidosis, lactic acidosis, uremia, and ingestion of salicylate, ethylene glycol, or methanol) metabolic acidosis is associated with an increased anion gap. In the face of excess metabolic acids, bicarbonate is depleted in the process of buffering excess hydrogen ions. Provided that the renal functions is normal, the kidney attempts to compensate by secreting an acid urine and retaining bicarbonate. 

The synthesis of 18F-FET is carried out in two steps (Wester et al, 1999) First, ethylene glycol-1,2-ditosylate in acetonitrile is reacted with dry 18F-containing Kryptofix 2.2.2 and potassium bicarbonate at 90°C for 10 min. The product is purified by absorbing it on a polystyrene cartridge and then eluting with dimethylsulfoxide. Second, the eluate is mixed with dipotassium sodium salt of L-tyrosine and heated at 90°C for 10min. The mixture is purified by HPLC and cation exchange to afford 18F-FET. The radiochemical yield is about 40-45% with purity between 97 and 99%. 

Systemically administered ethanol is confined to the treatment of poisoning by methyl alcohol and ethylene glycol. Treatment consists of sodium bicarbonate to combat acidosis, hemodialysis, and the administration of ethanol, which slows the formation of methanol s metabolites, formaldehyde and formic acid, by competing with methanol for metabolism by ADH (Figure 22-1). Formic acid causes nerve damage its effects on the retina and optic nerve can cause blindness. 

The hydrolysis of the amyl chlorides with sodium oleate and caustic soda solution to form the corresponding alcohols is the basis of a flourishing industry and is discussed on another page. The ease of removal of halogen increases markedly from chlorine to iodine and with increasing complexity of the compound. Ethylene chlorohydrin, for example, is easily and smoothly hydrolyzed to ethylene glycol by aqueous sodium bicarbonate CH,0HCH,C1 + NaHCO, aq. - CH,OHCH,OH -H CO. + NaCl... 

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