Linear primary alcohols

The Ziegler process, based on reactions discovered in the 1950s, produces predorninandy linear, primary alcohols having an even number of carbon atoms. The process was commercialized by Continental Oil Company in the United States in 1962, by Condea Petrochemie in West Germany (a joint venture of Continental Oil Company and Deutsche Erdid, A.G.) in 1964, by Ethyl Corporation in the United States in 1965, and by the USSR in 1983. 

Alkylation of aluminum with ethyleae yields products that fiad appHcatioa as iaitiators and starter compounds ia the productioa of a-olefias and linear primary alcohols, as polymerization catalysts, and ia the syathesis of some monomers like 1,4-hexadieae. Triethyl aluminum [97-93-8] A1(C2H3)2, is the most important of the ethylene-derived aluminum alkyls. 

The Alfol process (Figure 7-7) for producing linear primary alcohols is a four-step process. In the first step, triethylaluminum is produced by the reaction of ethylene with hydrogen and aluminum metal ... 

Alcohol and alcohol ether sulfates are commonly considered as extremely rapid in primary biodegradation. The ester linkage in the molecule of these substances, prone to chemical hydrolysis in acid media, was considered the main reason for the rapid degradation. The hydrolysis of linear primary alcohol sulfates by bacterial enzymes is very easy and has been demonstrated in vitro. Since the direct consequence of this hydrolysis is the loss of surfactant properties, the primary biodegradation, determined by the methylene blue active substance analysis (MBAS), appears to be very rapid. However, the biodegradation of alcohol sulfates cannot be explained by this theory alone as it was proven by Hammerton in 1955 that other alcohol sulfates were highly resistant [386,387]. 

Linear primary alcohol sulfates can also be biodegraded under anaerobic conditions but the process seems to be limited to the hydrolysis of the sulfate [407]. 

Linear primary alcohol sulfates often need only one day for 95 % primary biodegradation and degrade faster than other anionic surfactants, which usually need several days. This difference has been confirmed by Ruschenberg [412, 413]. 

However, they behave similarly to alcohol sulfates since linear alcohol ether sulfates are more easily biodegradable than branched alcohol ether sulfates. Also linear secondary alcohol ether sulfates are poorer than linear primary alcohol ether sulfates [425]. 

Steinle et al. [426] studied the primary biodegradation of different surfactants containing ethylene oxide, such as sulfates of linear primary alcohols, primary oxoalcohols, secondary alcohols, and primary and secondary alkyl-phenols, as well as sulfates of all these alcohols and alkylphenols with different degrees of ethoxylation. Their results confirm that primary linear alcohol sulfates are slightly more readily biodegradable than primary oxoalcohol sulfates and that secondary alcohol sulfates are also somewhat worse than the corresponding linear primary. 

If primary alcohols with a straight chain of 10-20 carbon atoms are initially alkoxylated by a mixture of ethylene and propylene oxides followed by phosphorylation, a pour point depression to 8°C will occur, whereas phosphate esters derived from nonylphenol are liquid at temperatures as low as 2°C. Phosphoric acid esters on the base of linear primary alcohols (Cn-Cl5) generally solidify below 24°C [50] (Table 2). 

Surfactant alcohols are linear, primary alcohols with carbon chain lengths in the C12-C14 and the C16-C18 range. Surfactant alcohols can be derived from either petrochemical or oleochemical feedstocks, and thus are referred to either as synthetic alcohols or as natural (oleochemical) alcohols. Petrochemical feedstocks used for surfactant alcohol production are ethylene and, to a lesser degree, paraffins. 

The oxo and modified oxo process involve the reaction of mixed a- and internal olefins with hydrogen and carbon monoxide to give predominantly linear primary alcohols, although both processes yield some branched alcohols. 

Alfol Also called the Conoco process and the Muhlheim process. The same name is used for the products as well. A process for making linear primary alcohols, from C2 to C28, from ethylene. The ethylene is reacted with triethyl aluminum, yielding higher alkyl aluminums These are oxidized with atmospheric oxygen under mild conditions to aluminum alkoxides, which are then hydrolyzed by water to the corresponding alcohols ... 

Linear Primary Alcohols CH3CH2( CH2CH2)xOH CH3CH2 (CH2CH2)yOH CH CH2 (CH2CH2)zOH... 

Fig. 1.11. Scheme for the formation of linear primary alcohols out of ethylene according to... 

For linear, primary alcohols (n-alkanols) the strength of complexation with CDs, expressed by pKs = —logKs, where Ks is the dissociation constant of the complex, correlates strongly with their coefficients for partition (Pe) between diethyl ether and water (Matsui and Mochida, 1979 Matsui et al., 1985), with slopes close to 1 (la and lb). It has also been... 

Linear Primary Alcohol Ethoxylates (LPAE). The hydrophobes of LPAE are made in several ways ... 

Figure 6. Suggested biodegradation pathway for hydrophobe of linear primary alcohol ethoxylates.

A C1215 essentially linear primary alcohol ethoxylate having an average of 9 ethylene oxide (EO) units per mole of alcohol (C12.15LPAE-9). The alcohol was prepared from Ci i.u olefins using catalytic addition of CO and H2. Approximately 80% of this alcohol contained linear alkyl chains. The 20% remaining contained 2-alkyl branches, mostly methyl. 

Instead of the displacement reaction, aluminum alkyls may be oxidized with dry air to produce aluminum alkoxides that, after hydrolysis with dilute sulfuric acid or water, yield linear primary alcohols with an even number of carbon atoms (fatty... 

C12-15 linear, primary alcohol ethoxylate or equivalent, such as Neodol 25-9 (Shell). 

Neodol 25-3 Ethoxylate Linear primary alcohol. MW 336 Shell... 

RAW MATERIALS Neodol 25-3 Ethoxylate CHEMICAL DESCRIPTION Linear primary alcohol SOURCE Shell... 

Evans et al. [4] carried out a quantitative determination of linear primary alcohol ethyoxylate surfactants in environmental waters by thermospray liquid chromatography-mass spectrometry. 

Ethylene Oligomers (Alpha Olefins) and Linear Primary Alcohols... 

Linear primary alcohols and alpha olefins in the C6-C 8 range have enjoyed remarkable growth in the last three decades. As esters, the C6—C,0 alcohols are used for plasticizing PVC. In the C 2-C]g range, the alcohols are used to make readily biodegradable surfactants of various types such as ethoxylates (nonionic), alcohol sulfates, and sulfates of ethoxylates (anionic). Alpha olefins are used as polyethylene comonomer (33%) and as raw materials for detergent alcohols (22%), oxo alcohols (10%), and lubricants and lube oil additives (18%). 

Activation Parameters for the Carbonylation of Linear Primary Alcohols with the Rhodium-Iodide Systenf... 

Surfactant critical micelle concentration (cmc) may be related to chemical structure using multiple correlation analysis. The cmc value plays an important role in surfactant adsorption, foaming, and interfacial tension properties. The 25 C cmc values of a series of high purity single component highly linear primary alcohol ethoxylates (Table 6) were analyzed using equation 4 ... 

The correlation equation obtained using the data summarized in Table 10 was 0.938. The modest correlation coefficient may be due to the use of commercial linear primary alcohol ethoxylates from two different manufacturers. Variatiofts in hydrophobe linearity, hydrophobe carbon number distribution about the average value, and EO chain length distribution about the average value were not considered in equation 8. This interpretation is supported by the observation that inclusion of data for three secondary (methyl branched at the alpha position of the hydrophobe) alcohol ethoxylates in the analysis resulted in a decrease of the correlation coefficient to <0.90. 

NEODOL ethoxylates are nonionic surfactants made from blends of linear primary alcohols with carbon numbers ranging from C9 to CIS. The alcohol blends are reacted with ethylene oxide (EO) to produce NEODOL ethoxylates with average chain lengths ranging from 2.5 to 13. For example, NEODOL 25-3 designates a surfactant based on NEODOL 25 alcohol reacted with an average of 3 moles of ethylene oxide (EO). 

Hydrocarboxylation of the Ce-Cs a-olefins with cobaltcarbonyl/pyridine catalysts at 200 °C and 20 MPa gives predominantly the linear carboxylic acids. The acids and their esters are used as additives for lubricants. The Ce-Cio a-olefins are hydroformylated to odd-numbered linear primary alcohols, which are converted to polyvinylchloride (PVC) plasticizers with phthalic anhydride. Oligomerization of (preferably) 1 -decene, applying BF3 catalysts, gives oligomers used as synthetic lubricants known as poly-a-olefins (PAO) or synthetic hydrocarbons (SHC) [11, 12]. The C10-C12 a-olefins can be epoxidized by peracids this opens up a route to bifunctional derivatives or ethoxylates as nonionic surfactants [13]. 

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