Linear alpha olefins

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. 

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. 

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). 

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). 

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). 

Linear alpha olefins Methyl ethyl ketone Xylene... 

Hexamethylenediamine Hydrogen cyanide Linear alpha olefins... 

A feature of the FT process is that the primary hydrocarbon products are linear alpha olefins. Since chain branching is a temperature sensitive secondary reaction, a higher yield of linear olefins is obtained when the FT process is operated at lower temperatures (eg see the data in Table III comparing the low temperature Arge with the high temperature Synthol process). 

Alternate products of a high degree of linearity can be produced by oxonation of linear alpha olefins. By this process, one can obtain alcohols of any desired chain length, including the odd-numbered ones. Except for tridecyl alcohol, odd-numbered alcohols in the plasticizer range are not currently produced in volume at attractive prices in the United States. 

For our study, individual samples of linear alpha olefins, containing from six to eleven carbons, were subjected to oxo synthesis to produce primary alcohols containing from 7 to 12 carbons. Analysis of the alcohols showed them to contain on the average 50% or more of the straight chain primary alcohols the remaining alcohols were also primary and consisted mainly of the 2-methyl isomers. To distinguish between 100% straight chain on the one hand, and 100% branched chain on the other, we call these new alcohols linear. ... 

For a hsting of selected physical properties of linear alpha olefins, see Table 8. 

Read, C.S.. R. Wilhalm, and Y. Yoslnda SRI Chemical Economics Handbook Linear Alpha Olefins, SRI International, Menlo Park, CA, Oct. 1993 Rubin, IT). Poly (1-Butene) Its Preparation and Properties, Gordon Breach, New York, 1968. 

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. 

With wax consisting of linear paraffins, an olefin product containing as much as 90% linear alpha olefins can be prepared. 

Production of higher olefins from lower and higher linear alpha olefins via isomerization and disproportionation (I/D). This is the detergent olefin production part of the SHOP unit. 

Al-Jarallah, A. M., Anabtawi, J. A., Siddiqui, M. A. B., Aitani, A. M. and Al-Sa doun, A. W. Ethylene dimerization and oligomerization to butene-i and linear alpha-olefins a review of catalytic systems and processes. Catal. Today, 1992, 14, 1-121. 

Probably the first example of a process employing the biphasic concept is the Shell process for ethylene oligomerization in which the nickel catalyst and the ethylene reactant are dissolved in 1,4-butanediol, while the product, a mixture of linear alpha olefins, is insoluble and separates as a second (upper) liquid phase (see Fig. 7.1). This is the first step in the Shell Higher Olefins Process (SHOP), the largest single feed application of homogeneous catalysis [7]. 

Alkylbenzene, linear Alpha olefins, linear Ammonia... 

One intriguing aspect of the Fischer-Tropsch process is the production of linear alpha-olefins. These can be separated as intermediates in the process and in theory the process could be optimised to produce these valuable products from coal or gas. 

C. S. Read, R. Willhalm, Y. Yoshida in Linear Alpha-Olefins, The Chemical Economics Handbook Marketing Research Report, SRI International, Oct. 1993, 681.5030A. 

Butene-1 is the first member of the linear alpha olefins (LAO)family. It is a basic petrochemical and it can be converted to products such as polybutene-1 and butylene oxide. However, the main use of butene-1 is as a co-monomer with ethylene for the polyethylene production (LLDPE and HDPE)which accounts for approximately 80% of the butene-1 market [1]... 

As the long chain olefins produced in the low temperature FT synthesis are almost exclusively linear alpha olefins, they are ideal for producing easily biodegradable detergents. Cuts from the Cg to products are reacted with benzene to produce alkyl benzenes which are sulphonated to give the detergents. The paraffins in the feedstock pass through the process, are chlorinated and used as plasticisers. Linear olefins can also be hydrofor-mulated to yield linear aldehydes and alcohols. 

When hydroformylating a Linear Alpha Olefin (LAO), rhodium inserts the aldehyde group 52% onto carbon one (70% for cobalt) and 48% onto carbon two (30% for cobalt). 

Axens Olefins, linear alpha Ethylene AlphaSelect process offers flexible product slate, low investment, low operating costs, liquid-phase homogenous catalysis to make high-purity C -C, linear alpha olefins NA NA... 

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