Ethyl ether decomposition

The ethyl ether decomposition reactions are endothermic and above 200 °C temperatures favor decomposition. 

Triiodoacetic acid [594-68-3] (I CCOOH), mol wt 437.74, C2HO2I3, mp 150°C (decomposition), is soluble in water, ethyl alcohol, and ethyl ether. It has been prepared by heating iodic acid and malonic acid in boiling water (63). Solutions of triiodoacetic acid are unstable as evidenced by the formation of iodine. Triiodoacetic acid decomposes when heated above room temperature to give iodine, iodoform, and carbon dioxide. The sodium and lead salts have been prepared. 

Beryllium Hydride. BeryUium hydride [13597-97-2] is an amorphous, colorless, highly toxic polymeric soHd (H = 18.3%) that is stable to water but hydroly2ed by acid (8). It is insoluble in organic solvents but reacts with tertiary amines at 160°C to form stable adducts, eg, (R3N-BeH2 )2 (9). It is prepared by continuous thermal decomposition of a di-/-butylberylhum-ethyl ether complex in a boiling hydrocarbon (10). 

The heavy metal salts, ia contrast to the alkah metal salts, have lower melting points and are more soluble ia organic solvents, eg, methylene chloride, chloroform, tetrahydrofiiran, and benzene. They are slightly soluble ia water, alcohol, ahphatic hydrocarbons, and ethyl ether (18). Their thermal decompositions have been extensively studied by dta and tga (thermal gravimetric analysis) methods. They decompose to the metal sulfides and gaseous products, which are primarily carbonyl sulfide and carbon disulfide ia varying ratios. In some cases, the dialkyl xanthate forms. Solvent extraction studies of a large number of elements as their xanthate salts have been reported (19). 

Chloro-l,2-propanediol [96-24-2] HOCH2CHOHCH2CI, a liquid with = 1.4831 (6), boils at 213°C and 101.3 kPa (1 atm) with decomposition. It can be distilled at 114—120°C at 1.87 kPa (14 mm Hg). Synonyms for this compound include 3-chloro-l,2-dihydroxypropane, glycerol monochlorohydrin, a-chlorohydrin, and 3-chloropropylene glycol. It is miscible in water, ethanol, ethyl ether, and acetone [67-64-1] (8) and is soluble in hot... 

In 1911 Benary reported a modification of Feist s original procedure. He reacted chloroacetaldehyde (8), generated in situ from the ammonia promoted decomposition of 1,2-dichloroethyl ethyl ether (7), with ethyl acetoacetate (9) and ammonia to yield ethyl 2-methyl 3-furoate (10). ... 

Decomposition HT will hydrolyze to form hydrochloric acid, thiodiglycol, and bis-(2-(2-hydroxyethylthio) ethyl ether. 

Presence of carbon dioxide in solutions of the hydride in dimethyl or bis(2-methoxy-ethyl) ether can cause a violent decomposition on warming the residue from evaporation. Presence of aluminium chloride tends to increase the vigour of decomposition to explosion. Lithium tetrahydroaluminate may behave similarly, but is generally more stable. 

B,j3,B"-Trichloroborazine forms white crystalline needles, m.p. 83.9 to 84.5°. It is extremely sensitive to moisture and decomposes violently in water. It is soluble without decomposition in anhydrous nonprotonic organic solvents such as benzene, ethyl ether, and carbon tetrachloride. 

HAZARDOUS DECOMPOSITION PRODUCTS T will hydrolyze to form HC1 and di-2-(2-hydroxy ethyl thio) ethyl ether. 

Chloromethyl ethyl ether 98 was lithiated in the presence of a catalytic amount of DTBB (5%) and an electrophile in THF at 0°C, to give after hydrolysis the expected functionahzed ethers 99 (Scheme 41) . Alternatively, the same process can be carried out in a two-step reaction, but performing the lithiation at —90°C in order to avoid the decomposition of a-ethoxymethyllithium 100 followed by the introduction of the electrophile. 

Action of Aliphatic Amines on Slow Oxidation of Acetaldehyde and Ethyl Ether, and on Decomposition of Organic Peroxides in the Gas Phase... 

Aliphatic amines have much less effect on the later reactions of the gas-phase oxidation of acetaldehyde and ethyl ether than if added at the start of reaction. There is no evidence that they catalyze decomposition of peroxides, but they appear to retard decomposition of peracetic acid. Amines have no marked effect on the rate of decomposition of tert-butyl peroxide and ethyl tert-butyl peroxide. The nature of products formed from the peroxides is not altered by the amine, but product distribution is changed. Rate constants at 153°C. for the reaction between methyl radicals and amines are calculated for a number of primary, secondary, and tertiary amines and are compared with the effectiveness of the amine as an inhibitor of gas-phase oxidation reactions. 

The higher decomposition points were obtained when adrenochrome methyl and ethyl ethers were prepared by oxidation of the appropriate catecholamine in methanol with silver oxide. The BOlid aminochromes were then obtained as microcrystalline solids on addition of dry ether and cooling the resultant solution to — 80°. The slightly less pure products were obtained when the oxidation was carried out in acetonitrile. [R. A. Heacock and B. D. Scott, loc. cit. (footnote c )]. 

The constant for the decomposition of gaseous propionic aldehyde falls away steadily below about 80 mm., that for the decomposition of diethyl ether below about 150 mm., that for the decomposition of diethyl ether below about 300 mm. Several other ethers, dipropyl ether, methyl propyl ether and methyl ethyl ether behave in a similar manner. The velocity constant for the decomposition of azomethane also diminishes but not until lower pressures are reached for example at 290° C. k at 0-259 mm. has one-fourth of its value at 707-9 mm. In several reactions, such as the racemization of pinene, and the decomposition of gaseous acetone the falling off of the velocity constant has not actually been looked for. The decomposition of azoisopropane is unimolecular down to pressures of 0-25 mm. 

Tellurium O-ethylisobutyrylacetone trichloride (Formula I).— Tellurium tetrachloride (1 mol.) is heated with isobutyrylacetone (B.pt. 95° C.) (2 mols.) in chloroform solution for one hour, the reaction mixture filtered from free tellurium and evaporated in a vacuum. The trichloride thus obtained in about 30 per cent, yield crystallises from benzene-petroleum mixture as pale yellow flakes or needles, M.pt. 103° C. with decomposition. It gives no coloration with ferric chloride, and is decomposed by 5N sodium hydroxide, the odour of the O-ethyl ether of the j8-diketone being noticed. 

As an alternative method of procedure, the following may be substituted for Steps 4 to 7 inclusive of the above process. After distilling the benzol, the tarry mass may be stirred directly with 2000 mL of hot 0.3 N NaOH with a mechanical stirrer. The suspension is chilled and the supernatant Liquid poured or siphoned off. Repetition of the extraction two or three times is advisable. The alkaline aqueous solution is then extracted five or six times with 400 mL portions of sulfuric ether, thus transferring the hormone to ether solution. After distillation of the ether the residue is steam distilled as long as a distillate other than water is obtained. The condensed water is removed by vacuum distillation and the small amount of dark tarry residue leached 5 times with 50 mL of hot 0.3 N NaOH. This solution is filtered and the filtrate extracted with sulfuric ether (100 mL, 6 times). The ether solution is distilled and the residue leached with cold 0.3 N NaOH using 20 mL five times. This alkaline solution is filtered and extracted with 50 mL of sulfuric ether five times. Upon distillation of the ether and solution of the residue in a small quantity of hot ethyl alcohol, the hormone separates in semi-crystalline balls which may be filtered off. A further quantity is obtained by adding 3 volumes of water to the alcoholic solution. It may be recrystallized from 25% aqueous ethyl alcohol or from 25% aqueous acetone or from any of the following chloroform, benzol, ethyl acetate, ethyl ether or petroleum ether. The final product consists of colorless crystals which, when crystallized from dilute alcohol, possess a distinct rhomboid outline. The crystals melt at 242-243°C (248-249°C corrected) with some decomposition. 

Later it was found that the decomposition of benzenediazonium salts with ethanol actually yields phenyl ethyl ether contaminated with a little benzene. This, coupled with the fact that a number of instances of ether formation had been recorded, led to the suggestion that the normal products of reaction between diazonium salts and ethanol are the ethers. 

One hundred grams of each sample were ground to a powder and extracted with a total volume of 1000 mL redistilled ethyl ether in two aliquots. Oil, carotenoids and other nonvolatile ether-extractable materials were removed from the extract by a modified Nicker-son-Likens procedure (4). The resulting distillate was dried with anhydrous sodium sulfate and concentrated with a spinning band still to a final volume of lOOpL. The concentrated extracts were stored in a freezer at -40°C to reduce further reactions or decompositions. 

Tetraethylammonium tetrafluoroborate. A solution of 5.3 g (25 mmol) of EttNBr in about 8 mL of water is reacted with HBF4 and concentrated. Next, it is diluted with ethyl ether and filtered to yield 4.6 g (85%) of the crude salt MP 375-378°C with decomposition. Two recrystallizations from a methanol-petroleum ether (BP 30-60°C) mixture yields 3.7 g (69%) of pure Et4NBF4 as white needles MP (after drying) 377-378°C with decomposition. 

The first study of a nucleophilic aromatic substitution in which formation of a Meisenheimer-type complex and its subsequent decomposition were separately observable was reported by Orvik and Bunnett (1970). The study involved the reaction of 2,4-dinitro-l-naphthyl ethyl ether [7] with n-butyl- and t-butylamine in DMSO. The use of DMSO in this kinetic study enabled the rate behaviour to be unambiguously interpreted by avoiding complications due to aggregation phenomena, while stabilizing any a-complexes which are formed. The reaction sequence is given in equation (28). In this OEt... 

The decomposition of eserethole methiodide to yield physostigmol ethyl ether is analogous to the reaction of thebaine methiodide (XI)... 

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