Vapor-Phase Hydration of Ethylene

Bliss, R. Harding; Dodge, Barnett F.

doi:10.1021/ie50325a004

Cited by 18 publications

(7 citation statements)

References 4 publications

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“…The numerous data obtained confirm previous work (4,10) in showing that the determination of olefins, aromatics, and saturates by simple extraction with sulfuric acid is unsatisfactory since highly inaccurate results may be obtained. However, in spite of its recognized shortcomings in the precise determination of hydrocarbon types, sulfuric acid can be used with considerable satisfaction for characterizing hydrocarbon oils conveniently, rapidly, and economically.…”

Section: Discussionsupporting

confidence: 85%

“…Since several -workers (4, 5,10,13) have shown that sulfuric acid reacts selectively with olefins, aromatics, and saturates, usually in the order named, attention was directed to this reagent. Consideration of the literature showed that little work had been done on the reactions of sulfuric acid with oils produced by coal hydrogenation and that all attempts to develop a simple and accurate method of determining olefinic, aromatic, and saturated hydrocarbons in other neutral oils were disappointing (4,10). Moreover, there are objections to classifying oils containing compounds with two or more functional groups (such as styrene and similar compounds of higher molecular weight) as mixtures of olefins, aromatics, and saturates.…”

Section: Discussionmentioning

confidence: 99%

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AEROGEL CATALYSTS Dehydrations and Decarboxylations

Kearby¹,

Swann²

1940

Ind. Eng. Chem.

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A comparison is made of the activities of aerogels, xerogels, and precipitates as catalysts for the dehydration of alcohols, the esterification of acetic acid with ethanol and the dehydration and decarboxylation of aliphatic acids. The aerogels were often, but not always, the most active catalysts. The advantages of the aerogel form are found to be of smaller magnitude than was predicted from earlier work. THIS communication is an extension of the general problem of evaluating aerogels as catalysts, which is being carried out in this laboratory. Kistler, Swann, and Appel (11) showed that thoria aerogel was a more active catalyst than the xerogel (ordinary dried gel) or precipitate for decarboxylating aliphatic acids and esters to ketones. In a study of the vapor-phase oxidation of acetaldehyde to acetic acid over silica and platinized silica, Foster and Keyes (7) showed that the best aerogels and xerogels have about the same activity. These gels appear to be the best vapor-phase

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Section: Discussionsupporting

confidence: 85%

Section: Discussionmentioning

confidence: 99%

AEROGEL CATALYSTS Dehydrations and Decarboxylations

Kearby¹,

Swann²

1940

Ind. Eng. Chem.

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“…As an example of the utilization of equilibrium data to obtain a free energy equation for an industrially important reaction, we shall consider the equilibrium in the hydration of ethylene. C2H< (gas) + H20 (gas) = C2HBOH (gas) The equilibrium in this reaction has been studied by several investigators (7,9,35). The free energy of the reaction was calculated indirectly by Parks from the third law of thermodynamics (34) and with more accuracy by Schumann and the author (S3) who also made the calculation from the heat of reaction and statistical mechanics.…”

Section: General Free Energy Relationsmentioning

confidence: 99%

Sources of Thermodynamic Data. Methods of Application to the Industry

Aston¹

1942

Ind. Eng. Chem.

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“…This fact has focused attention on determination of equilibrium constants and equilibrium yields (147)(148)(149). The results of these determinations are as follows:…”

Section: Equilibrium Constantmentioning

confidence: 99%

Ethanol

Logsdon¹

2004

Kirk-Othmer Encyclopedia of Chemical Technology

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ETHANOL 1 a Refs. 6-14. b To convert kPa to atm, divide by 101.3. c To convert J to cal, divide by 4.184. d To convert C·m to debye, divide by 3.336 × 10 −30 (esu = D × 10 −18 ) .A summary of physical properties of ethyl alcohol is presented in Table 1. Detailed information on the vapor pressure, density, and viscosity of ethanol can be obtained from References 6-14. A listing of selected binary and ternary azeotropes of ethanol is compiled in Reference 15. Chemical PropertiesThe chemistry of ethyl alcohol is largely that of the hydroxyl group, namely, reactions of dehydration, dehydrogenation, oxidation, and esterification. The hydrogen atom of the hydroxyl group can be replaced by an active metal, such as sodium, potassium, and calcium, to form a metal ethoxide (ethylate) with the evolution of hydrogen gas (see Alkoxides, metal). 2 C 2 H 5 OH + 2 M −→ 2 C 2 H 5 OM + H 2 Sodium ethoxide [141-52-6] can be prepared by the reaction of absolute ethyl alcohol and sodium, or by refluxing absolute ethyl alcohol with anhydrous sodium hydroxide (16): CH 3 CH 2 OH + NaOH −→ CH 3 CH 2 ONa + H 2 O ETHANOL 3Commercially, water is removed by azeotropic distillation with benzene (17). Sodium ethoxide precipitates upon addition of anhydrous acetone (18). This strong base hydrolyzes readily to give ethyl alcohol and sodium and hydroxyl ions.Sodium ethoxide can also be prepared by the reaction of sodium amalgam with ethyl alcohol.Sodium ethoxide is used in organic synthesis as a condensing and reducing agent. The reaction between sodium ethoxide and sulfur monochloride yields diethyl thiosulfite (19).2 CH 3 CH 2 ONa + S 2 Cl 2 −→ (CH3CH2O) 2 S 2 + 2 NaCl Barbiturates (Veronal, Barbital, Luminal, Amytal), ethyl orthoformate, and other chemicals are produced commercially from sodium ethoxide.Aluminum and magnesium also react to form ethoxides, but the reaction must be catalyzed by amalgamating the metal (adding a small amount of mercury).6 CH 3 CH 2 OH + 2 Al −→ 2 (CH3CH2O) 3 Al + 3 H 2 2 CH 3 CH 2 OH + Mg −→ (CH3CH2O) 2 Mg + H 2 Well-cleaned aluminum filings react at room temperature in the presence of mercuric chloride (20, 21). In an autoclave, metallic aluminum and ethyl alcohol react without a catalyst at 120 • C (22). The reaction can also be promoted by the addition of sodium ethoxide (23). Aluminum should be avoided as a material of construction for ethanol service.Other reactions involving the hydrogen atom of the hydroxyl group in ethyl alcohol include the opening of epoxide rings to form hydroxy ethers, and the addition to acetylene [74-86-2] to form ethyl vinyl ether [104-92-2].These reactions are carried out in the presence of acidic and basic catalysts. The acid-catalyzed addition of ethyl alcohol to acetylene or to a vinyl ether produces acetals (diethers of 1,1-dihydroxyethane). The acid-catalyzed reaction of ethyl alcohol with an aldehyde or ketone also gives acetals.The hydroxyl group can be replaced by halogens from inorganic acid halides or phosphorus halides to give two different products, ethyl esters of the...

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Vapor-Phase Hydration of Ethylene

Cited by 18 publications

References 4 publications

AEROGEL CATALYSTS Dehydrations and Decarboxylations

AEROGEL CATALYSTS Dehydrations and Decarboxylations

Sources of Thermodynamic Data. Methods of Application to the Industry

Ethanol

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