Hydrocarbons, hydrocarbon ethylene derivs. from

As primary alcohols must contain the group (—CH2—OH), it is plain that the simplest primary alcohol of the ethylene hydrocarbons must be derived from the first hydrocarbon of this series which contains a methyl group. This will be the three carbon member, viz., propene, CH2 = CH—CH3. As ethene, CH2 = CH2, contains no such methyl group it can not yield a primary alcohol. 

It is apparent from the data in Table 13.1 that most organic chemical commodities are extracted from hydrocarbon mixtures, are derived from hydrocarbons, or are the basic raw materials for the manufacture of other products. As the ranking decreases, many of the high-volume chemicals are used as feedstocks for lower ranked organic chemicals. Ethylene and propylene are the top two organic chemicals. They are used as feedstocks for many of the... 

Stannous fluoride Knoevenagel condesation Synthesis of ethylene derivatives from aldehydes and hydrocarbons... 

According to Olah s investigations the conversion of methyl alcohol over bifunctional acidic-basic catalyst after initial acid-catalyzed dehydration to dimethyl ether involves oxonium ion formation catalyzed also by the acid functionality of the catalyst. This is followed by basic site catalyzed deprotonation to a reactive surface-bound oxonium ylide, which is then immediately methylated by excess methyl alcohol or dimethyl ether leading to the crucial - 2 conversion step. The ethyl methyl oxonium ion formed subsequently eliminates ethylene. All other hydrocarbons are derived from ethylene by known oligomerization-fragmentation chemistry. Propylene is formed via a cyclopropane intermediate. The overall reaction sequence is depicted in Scheme 19. 

Ethylene derivatives from a / -ethyleneketones s. 12,115 limitations s. Soc. 1960, 1406 Hydrocarbons from carboxylic acids... 

Olefins are produced primarily by thermal cracking of a hydrocarbon feedstock which takes place at low residence time in the presence of steam in the tubes of a furnace. In the United States, natural gas Hquids derived from natural gas processing, primarily ethane [74-84-0] and propane [74-98-6] have been the dominant feedstock for olefins plants, accounting for about 50 to 70% of ethylene production. Most of the remainder has been based on cracking naphtha or gas oil hydrocarbon streams which are derived from cmde oil. Naphtha is a hydrocarbon fraction boiling between 40 and 170°C, whereas the gas oil fraction bods between about 310 and 490°C. These feedstocks, which have been used primarily by producers with refinery affiliations, account for most of the remainder of olefins production. In addition a substantial amount of propylene and a small amount of ethylene ate recovered from waste gases produced in petroleum refineries. 

Polymers. Hydrocarbons from petroleum and natural gas serve as the raw material for virtually all polymeric materials commonly found in commerce, with the notable exception of rayon which is derived from cellulose extracted from wood pulp. Even with rayon, however, the cellulose is treated with acetic acid (qv), much of which is manufactured from ethylene (see Fibers, regenerated cellulosics). 

Although acetylene production in Japan and Eastern Europe is stiU based on the calcium carbide process, the large producers in the United States and Western Europe now rely on hydrocarbons as the feedstock. Now more than 80% of the acetylene produced in the United States and Western Europe is derived from hydrocarbons, mainly natural gas or as a coproduct in the production of ethylene. In Russia about 40% of the acetylene produced is from natural gas. 

A second major use for chlorine derives from its reactivity with organic materials, in particular with hydrocarbons. Two chlorinated hydrocarbons, ethylene dichloride (lUPAC name 1,2-dichloroethane) and vinyl chloride (lUPAC... 

The alkene series of hydrocarbons is characterized by having one double bond in the carbon chain. The characteristic formula for members of the series is C H2 . Since there must be at least two carbon atoms present to have a carbon-to-carbon double bond, the first member of this series is ethene, C2H4, also known as ethylene. Propene (propylene), C,Hh, and butene (butylene), C4HK, are the next two members of the series. Note that the systematic names of these compounds denote the number of carbon atoms in the chain with the name derived from that of the alkane having the same number of carbon atoms (Table 21-2). Note also that the characteristic ending -ene is part of the name of each of these compounds. 

Although we have included acetic acid manufacture under ethylene derivatives, as you can see it is made from three of the seven basic organics ethylene, C4 hydrocarbons, and methane, with the most important method being from methane. Pure 100% acetic acid is sometimes called glacial acetic because when cold it will solidity into layered crystals similar in appearance to a glacier. It is a colorless liquid with a pungent, vinegar odor and sharp acid taste, bp 118°C, and mp 17°C. 

The large volume solvents, trichloroethylene and perchloroethylene, are still chiefly made from acetylene, but appreciable amounts of the former are derived from ethylene. The competitive situation between these source materials runs through the whole chlorinated hydrocarbon picture, and extends on to other compound classes as well—for example, acrylonitrile is just on the threshold of a severalfold expansion, as demand grows for synthetic fibers based thereon. Acrylonitrile can be made either from ethylene oxide and hydrogen cyanide, from acetylene and hydrogen cyanide, or from allylamines. The ethylene oxide route is reported to be the only one in current commercial use, but new facilities now under construction will involve the addition of hydrogen cyanide to acetylene (27). 

The most versatile starting material presently derived from petroleum for the production of polymeric products is ethylene. This gaseous hydrocarbon is produced in large volumes in cracking processes and is recovered from refinery gases (i) for direct polymerization or for conversion to other polymerizable monomers. The production of ethylene for use in chemical processes has undergone a fourfold increase in the last 10 years in 1950, production for this purpose was almost 1.5 billion pounds (<2). 

Alkyl one. An organic radical derived from an unsaturated hydrocarbon eg, ethylene, propylene, etc... 

Another major chlorinated hydrocarbon is vinyl chloride. For many years acetylene was the sole raw material for the production of vinyl chloride by a catalytic fixed bed vapor-phase process. This process is characterized by high yields and modest capital investment. Nevertheless, the high relative cost of acetylene provided an incentive to replace it in whole or in part by ethylene. The first step in this direction was the concurrent use of both raw materials. Ethylene was chlorinated to di-chloroethane, and the hydrogen chloride derived from the subsequent dehydrochlorination reacted with acetylene to form additional vinyl chloride. 

The U.S. ethylene industry has been based primarily on the cracking of ethane and propane derived from natural gas. The quantities and liquid contents of U.S. natural gases have been such as to permit substantial quantities of these light hydrocarbons to be recovered for use as economically attractive ethylene feedstocks. In Europe and Japan, however, naphthas have been generally the available and preferred feeds to pyrolysis. 

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