Olefin alpha

Linear hydrocarbons with a double bond at the end of the carbon chain are produced by the polymerization, or more correctly, the oligomerization of ethylene. 

Compounds with 6 to 18 carbons are the most common alpha olefins (a-olefins) and Ziegler catalysts are used in this process. Certain olefins such as nonene (C9) and dodecene (C12) can also be made by cracking and dehydrogenation of n-paraffins, as practiced in the petrochemical section of a refinery. 

Linear alpha olefins can be copolymerized with polyethylene to form linear low-density polyethylene (LLDPE) and 1-hexene (C6) and 1-octene (C8) are especially useful for this purpose. In addition, linear alpha olefins are used to make detergent alcohols, oxo alcohols for plasticizers, lubricants, lube oil additives, and surfactants are other important products from linear alpha olefins. 

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Olefin polymers alpha-olefin polymers (PAO), polybutenes and alkylaromatics, in particular the dialkylbenzenes (DAB). This class of compounds is the most widespread and accounted for 44% of the synthetic base market in France in 1992. 

Alpha olefins Alpha-olefin sulfonates Alphaprodine [77-20-3]... 

Exxon Chemical Erance, Hames, Erance 125 /-Cg,C2,Cio / -C2,C i,Ci2,Ci5 polygas olefins, alpha olefins... 

Exxon Chemical, Baton Rouge, La., U.S. 295 /-Cg to polygas olefins, alpha olefins, butene... 

There are two important side reactions, particularly above 120°C (/) aluminum alkyls decompose to form diaLkylalurninum hydrides and alpha olefins (the diaLkylalurninum hydrides rapidly react with ethylene to regenerate a trialkylalurninum) ... 

This second reaction leads to the small amount of branching (usually less than 5%) observed in the alcohol product. The alpha olefins produced by the first reaction represent a loss unless recovered (8). Additionally, ethylene polymerisation during chain growth creates significant fouling problems which must be addressed in the design and operation of commercial production faciUties (9). 

A.luminum Jilkyl Chain Growth. Ethyl, Chevron, and Mitsubishi Chemical manufacture higher, linear alpha olefins from ethylene via chain growth on triethyl aluminum (15). The linear products are then used as oxo feedstock for both plasticizer and detergent range alcohols and because the feedstocks are linear, the linearity of the alcohol product, which has an entirely odd number of carbons, is a function of the oxo process employed. Alcohols are manufactured from this type of olefin by Sterling, Exxon, ICI, BASE, Oxochemie, and Mitsubishi Chemical. 

Shell Higher Olefin Process) plant (16,17). C -C alcohols are also produced by this process. Ethylene is first oligomerized to linear, even carbon—number alpha olefins using a nickel complex catalyst. After separation of portions of the a-olefins for sale, others, particularly C g and higher, are catalyticaHy isomerized to internal olefins, which are then disproportionated over a catalyst to a broad mixture of linear internal olefins. The desired fraction is... 

The latest of three ethylene recovery plants was started in 1991. Sasol sold almost 300,000 t of ethylene in 1992. Sasol also produces polypropylene at Secunda from propylene produced at Sasol Two. In 1992 Sasol started constmction of a linear alpha olefin plant at Secunda to be completed in 1994 (40). Initial production is expected to be 100,000 t/yr pentene and hexene. Sasol also has a project under constmction to extract and purify krypton and xenon from the air separation plants at Sasol Two. Other potential new products under consideration at Sasol are acrylonitrile, acetic acid, acetates, and alkylamines. 

A.lpha-Olefm Sulfonates. Sulfonation of alpha-olefins yields a mixture of alkene sulfonates, hydroxyalkane sulfonates, and some amount of various disulfonates. These detergents are excellent foamers with good detergency properties. They are unaffected ia hard water and thek effects are considered superior to the alkyl ether sulfates (9). 

Alkenylsuccinic anhydrides made from several linear alpha olefins are used in paper sizing, detergents, and other uses. Sulfosuccinic acid esters serve as surface active agents. Alkyd resins (qv) are used as surface coatings. Chlorendric anhydride [115-27-5] is used as a flame resistant component (see Flame retardants). Tetrahydrophthalic acid [88-98-2] and hexahydrophthalic anhydride [85-42-7] have specialty resin appHcations. Gas barrier films made by grafting maleic anhydride to polypropylene [25085-53-4] film are used in food packaging (qv). Poly(maleic anhydride) [24937-72-2] is used as a scale preventer and corrosion inhibitor (see Corrosion and corrosion control). Maleic anhydride forms copolymers with ethylene glycol methyl vinyl ethers which are partially esterified for biomedical and pharmaceutical uses (189) (see Pharmaceuticals). 

The even-numbered carbon alpha olefins (a-olefins) from through C q are especially useful. For example, the C, C, and Cg olefins impart tear resistance and other desirable properties to linear low and high density polyethylene the C, Cg, and C q compounds offer special properties to plasticizers used in flexible poly(vinyl chloride). Linear C q olefins and others provide premium value synthetic lubricants linear 145 olefins are used in... 

Chevron Permit AppHcations and Reports to the Texas Air Control Board for Alpha Olefins Plants NAOU-1791 and NAOU-1797, Chevron Research and Technology Co. 

N. B. Godrej and co-workers. Proceedingsfirom "Alpha Olefins from Oleochemical Raw Materials," The Third World Detergent Confierence, Montreux, Switzerland, Sept. 1993. 

Gravity override of low density steam leads to poor volumetric sweep efficiency and low oil recovery in steam floods. Nonchemical methods of improving steam volumetric sweep efficiency include completing the injection well so steam is only injected in the lower part of the oil-bearing zone (181), alternating the injection of water and steam (182), and horizontal steam injection wells (183,184). Surfactants frequently are used as steam mobihty control agents to reduce gravity override (185). Field-proven surfactants include alpha-olefin sulfonates (AOS), alkyltoluene sulfonates, and neutralized... 

Thermal stabihty of the foaming agent in the presence of high temperature steam is essential. Alkylaromatic sulfonates possess superior chemical stabihty at elevated temperatures (205,206). However, alpha-olefin sulfonates have sufficient chemical stabihty to justify their use at steam temperatures characteristic of most U.S. steamflood operations. Decomposition is a desulfonation process which is first order in both surfactant and acid concentrations (206). Because acid is generated in the decomposition, the process is autocatalytic. However, reservoir rock has a substantial buffering effect. 

The alpha-olefin sulfonates (AOS) have been found to possess good salt tolerance and chemical stabiUty at elevated temperatures. AOS surfactants exhibit good oil solubilization and low iaterfacial tension over a wide range of temperatures (219,231), whereas less salt tolerant alkylaromatic sulfonates exhibit excellent chemical stabiUty. The nature of the alkyl group, the aryl group, and the aromatic ring isomer distribution can be adjusted to improve surfactant performance under a given set of reservoir conditions (232,233). 

Linear alpha-olefins are the source of the largest volume of ahphatic amine oxides. The olefin reacts with hydrogen bromide in the presence of peroxide catalyst, to yield primary alkyl bromide, which then reacts with dimethylamine to yield the corresponding alkyl dimethyl amine. Fatty alcohols and fatty acids are also used to produce amine oxides (Fig. 1). 

Thermally stable foam additives, such as alkylaryl sulfonates and C -C g alpha-olefin sulfonates, are being used in EOR steam flooding for heavy od production. The foam is used to increase reservoir sweep efficiency (178,179). Foaming agents are under evaluation in chemical CO2 EOR flooding to reduce CO2 channeling and thus increase sweep efficiency (180). 

Anhydrous sulfonic acids, particularly linear alkylben2enesulfonic acids, are typically stored ia stainless steel containers, preferably type 304 or 316 stainless steel. Use of other metals, such as mild steel, contaminates the acid with iron (qv), causiag a darkening of the acid over time (27). The materials are usually viscous oils which may be stored and handled at 30—35°C for up to two months (27). AH other detergent-grade sulfonic acids, eg, alcohol sulfates, alcohol ether sulfates, alpha-olefin sulfonates, and alpha-sulfomethyl esters, are not stored owiag to iastabiUty. These are neutrali2ed to the desired salt. 

Specialty sulfonic acid-based surfactants make up a rather large portion of surfactant production in the United States. Approximately 136,000 metric tons of specialty sulfonic acid-based surfactants were produced in 1992, which included alpha-olefin sulfonates, sulfobetaines, sulfosuccinates, and alkyl diphenyl ether disulfonates (64). These materials found use in the areas of household cleaning products, cosmetics (qv), toiletries, emulsion polymerization, and agricultural chemical manufacture. 

In tanneries, sodium bisulfite is used to accelerate the unhairing action of lime. It is also used as a chemical reagent ia the synthesis of surfactants (qv). Addition to alpha-olefins under radical catalyzed conditions yields sodium alkylsulfonates (wetting agents). The addition of sodium bisulfite under base-catalyzed conditions to dialkyl maleates yields the sulfosucciaates. 

Miscellaneous Copolymers. VP has been employed as a termonomer with various acryUc monomer—monomer combinations, especially to afford resins usehil as hair fixatives. Because of major differences in reactivity, VP can be copolymerized with alpha-olefins, but the products are actually PVP grafted with olefin or olefin oligomers (151,152). Likewise styrene can be polymerized in the presence of PVP and the resulting dispersion is unusually stable, suggesting that this added resistance to separation is caused by some grafting of styrene onto PVP (153). The Hterature contains innumerable references to other copolymers but at present (ca 1997), those reviewed in this article are the only ones known to have commercial significance. 

PVP/alpha-olefins ISP/Ganex various (olefin chain length surface active film formers waterproofing... 

Oligomerization of Ethylene. 1-Butene is a small by-product in the production of linear alpha-olefins by oligomerisation of ethylene. Linear alpha-olefins have one double bond at the terminal position and comprise the homologous series of compounds with carbon atoms between 4 and 19. The primary use of alpha-olefins is in the detergent industry. About 245,000 t/yr of 1-butene was produced for chemical use in the Gulf Coast of the United States in 1988 (72). 

Rhodium catalyst is used to convert linear alpha-olefins to heptanoic and pelargonic acids (see Carboxylic acids, manufacture). These acids can also be made from the ozonolysis of oleic acid, as done by the Henkel Corp. Emery Group, or by steam cracking methyl ricinoleate, a by-product of the manufacture of nylon-11, an Atochem process in France (4). Neoacids are derived from isobutylene and nonene (4) (see Carboxylic acids, trialkylacetic acids). 

Alpha Olefins Applications Handbook, edited by George R. Lappin and Joseph L. Sauer... 

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