Surfactant production, intermediates alkylphenol

In more recent in-depth investigations on this issue [22], a series of chlorinated and brominated by-products of alkylphenolic surfactants and their degradation intermediates formed during chlorine disinfection of raw water were identified using mass spectrometry (Table 6.6.2). 

Ethylene oxide is an important intermediate chemical not only for the production of nonionic surfactants like fatty alcohol ethoxylates, alkylphenol ethoxy lates, or propylene oxide/ethylene oxide block copolymers, but also for manufacturing of anionic surfactants like alcohol ether sulfates. 

Monoester salts of phosphoric acid derived from fatty alcohol ethylene oxide adduct or alkylphenol ethylene oxide adduct useful as surfactants are prepared by addition of R(OCH2CH2) OH, alkali fluoride and (C12P0)20 in a molar ratio of 0.9-1.5 0.05-1 1.0 at -50 to + 10°C and hydrolysis of the Cl-containing intermediates with a base. The monoester phosphates showed comparable or better washing and foaming efficiency than commercial products [12]. 

Alkylphenol. Alkylphenol is a common surfactant intermediate used to produce alkylphenol ethoxylates. Phenol reacts with an olefin thermally without a catalyst but with relatively poor yields. Catalysts for the reaction include sulfuric acid p-toluene sulfonic acid (PTSA), strong acid resins, and boron trifluoride (BF3). Of these, strong acid resins and BF3 are mostly widely used for the production of surfactant-grade alkylphenols. The most common alkylphenols are octylphenol, nonylphenol, and dodecylphe-nol. Mono nonylphenol (MNP) is by far the most common hydrophobe. It is produced by the alkylation of phenol with nonene under acid conditions. All commercially produced MNP is made with nonene based on propylene trimer. Because of the skeletal rearrangements that occur during propylene oligomerization, MNP is a complex mixture of branched isomers. 

Higher n-olefins of Cs-Ci4 are used as intermediates in the manufacture of several types of surfactant materials. Linear internal olefins are used in the production of linear alkylbenzene alkylphenol detergent alcohols, which in turn is used to produce alcohol sulfates, alcohol ethoxylates, and alcohol ether sulfates and synthetic lubricants. a-Olefins are used in the production of detergent alcohols, linear alkylbenzene, synthetic lubricants, and a-olefin sulfonates (another ionic surfactant). 

The worldwide annual production of all alkylphenols exceeds 1 billion pounds. The direct use of alkylphenols is, however, limited to only a few minor applications. The vast majority of alkylphenols are used as intermediates in the synthesis of derivatives, which (in turn) have a wide range of applications ranging from surfactants to pharmaceuticals. The principal markets for alkylphenols are nonionic surfactants, lube-oil additives, phenolic resins, polymer additives, and agrochemicals. The alkylphenols that are most significant in surfactant and applications, along with their general mode of manufactme and other major commercial applications are... 

Alkylphenol ethoxylate (APE) surfactants make up approximately 10% of overall consumption. While effective in many industrial applications, they face a number of environmental challenges that could greatly reduce their use in the future. Of major importance are questions concerning their relatively slow rate of biodegradation and the possible toxicity of degradation intermediates, especially phenols and other aromatic species. In the United States and western Europe, many detergent manufacturers have voluntarily discontinued their use in household products. 

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