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Alkylphenols and Alkylphenol Ethcpwlates Their Impact on Living Organisms, Biodegradation, and Environmental Pollution
Published in Ederio Dino Bidoia, Renato Nallin Montagnolli, Biodegradation, Pollutants and Bioremediation Principles, 2021
Tomasz Grześkowiak, Andrzej Szymański, Agnieszka Zgoła-Grześkoviak, Czarczyńska-Goślińska Beata, Robert Frankowskil
Alkylphenols, mainly nonylphenol (NP) and octylphenol (OP), are widely manufactured chemicals, which are produced during alkylation of phenol with nonene (obtained from trimerization of propene) or octene (obtained from dimerization of butene) in the presence of a catalyst. APs can be transformed to alkylphenol ethoxlyates, which are commonly used surfactants (Reed 1978, Groshart et al. 2001). NP is used mostly for production of nonylphenol ethoxylates (NPEs), and in plastic industry (e.g., for production of resins and tri(4-nonylphenyl) phosphite)—a heat stabilizer), and also in the production of oximes (used for manufacturing metals) (Groshart et al. 2001, SUBSPORT 2013). On the other hand, OP is rarely used in the synthesis of octylphenol ethoxylates (OPEs), and it is estimated that 98% of OP is used in the production of phenolic resins (OSPAR 2006). NPEs are used in many applications, including industrial cleaning, textile and leather processing, paper production, metal processing, extraction of crude petroleum and natural gas, paints and lacquer manufacturing, as well as pest control products (Groshart et al. 2001, SUB SPORT 2013). OPEs are mainly used in emulsion polymerization, but also in the production of octylphenol ether sulphates, textile and leather processing, pesticide formulations, and paints (OSPAR 2006). As a result of their widespread usage and problematic biodegradation, APs and APEs are directed to the environment, and are ubiquitous in both surface waters and sediments (Fig. 1.1).
Alkylene Oxides: Manufacture, Chemistry, and Applications
Published in F. E. Bailey, Joseph V. Koleske, Alkylene Oxides and Their Polymers, 2020
F. E. Bailey, Joseph V. Koleske
The principal uses of ethylene oxide (about 60 percent) are as automotive antifreeze and as the dihydroxy intermediate in manufacture of terephthalate polymer for polyester fibers, films, and bottles. The second largest use of ethylene oxide is in nonionic surfactants, principally ethylene oxide adducts of linear alcohols to provide biodegradable surfactants for heavy-duty home laundry formulations and anionic ether sulfates for home laundry and dishwashing formulations. Ethoxylated alkylphenols used in industrial and household detergents are also made. Alkanolamines are used in a wide variety of ways, including production of soaps, detergents, and textile chemicals. The glycol ethers have been widely used as industrial coating solvents. The polyglycols are used as intermediates, solvents, humectants, and lubricants.
Household and Personal Care Products: Cleaning up and Looking Good
Published in Richard J. Sundberg, The Chemical Century, 2017
The alkylphenol ethoxylates (Section 6.1.3.1) have come under particular scrutiny. The issue is the biotransformation, including in water treatment facilities, to alkylphenols, particularly octyl- and nonylphenol, which exhibit both toxicity to aquatic organisms and weak estrogenic effects.32 While the alkylphenol ethoxylates are effectively biodegraded under aerobic conditions, they can accumulate in anaerobic sludge. The phenolic metabolites have been detected in significant quantity downstream of plants that use the surfactants in manufacturing, such as wool and paper processers. Among the degradation products are octyl and nonylphenol. Since the side chains of these phenols are highly branched, they are quite resistant to oxidative degradation. Both octyl and nonyl phenols show estrogenic activity, which is not surprising given their general structural similarity to estradiol. One of the problems is that the nonyl phenols is a mixture of as many as 20 different isomers, making it difficult to identify and study specific degradation products. The products were voluntarily removed from many European household products beginning in 1995 and from industrial products in 2000.33 In contrast, these materials remain available in the United States. An industry-sponsored review of data available in 2008 concluded that neither the products nor their metabolites meet the criteria for persistent, bioacumulative, and toxic compounds.34
Improve Bastnaesite Flotation via Synergistic Effect of Octyl Hydroxamic Acid and Octyl Phenol Ethoxylated Surfactants
Published in Mineral Processing and Extractive Metallurgy Review, 2023
Xu Wu, Yiwen Hu, Sultan Ahmed Khoso, Zhao Cao
Anionic-nonionic surfactants have the advantages of improving solubility, selective adsorption, ionic resistance, and hydrophobicity of the mineral surface in mineral flotation (Filippova et al. 2014; Li et al. 2018; Liu et al. 2017; Qiao et al. 2020). Alkylphenol ethoxylates are commonly used nonionic surfactants. Since the properties can be adjusted according to the lengths of the polyethylene oxide chains, they are widely used in various fields, such as foaming, emulsification, and dyes (Furlong and Aston 1982). In the past several years, alkylphenol ethoxylates have been successfully utilized as surfactants to optimize the hydrophobicity of mineral surfaces (Misra, Mishra, and Somasundaran 2003; Misra, Panigrahi, and Somasundaran 2006). Octyl phenol ethoxylates and sodium oleate have been used together to recover apatite by flotation. The results show that Octyl phenol ethoxylates can reduce the influence of calcium ions in the solution on oleate, improve the adsorption efficiency of sodium oleate, and enhance the hydrophobicity of mineral surfaces. Moreover, Octyl phenol ethoxylates has been successfully applied to practical mineral flotation processes (Sis and Chander 2003). Although anion-nonionic combination surfactants have displayed significant flotation benefits in bastnaesite flotation, there are few reports on their potential applications and mechanisms.
Detection of APEO in textiles by HPLC
Published in The Journal of The Textile Institute, 2021
Alkylphenol ethoxylates (APEO) were mainly referred to nonylphenol ethoxylates (NPEO) and octylphenol ethoxylates (OPEO). They have widely been used as a kind of polyoxyethylene nonionic surfactants in chemical processing of textile products when dyeing and finishing. Human may face a higher exposure to APEO through skin contact by textile transmission. Considering their alleged ‘toxicity, persistence, and the liability to bioaccumulate’ on several animal species, especially human health, Alkylphenol ethoxylates have been prohibited or restricted by many countries and organizations. The European Union has implemented sales and use restrictions on certain applications in which Alkylphenol ethoxylates are used (ISO 13528, 2005; ISO 18254-1, 2016). The step followed similar measures in mainland China. The method standard called GB/T23322-2009 ‘Textiles - Determination of sufactan-Alkylphenol ethoxylates’ has been all round implemented (Chen et al. 2009). The method standards include extraction procedure and satisfactory separation of all analytes using High-Performance Liquid Chromatography. The extraction procedure using Soxhlet Extraction described in GB code method standard is different from the reference test methods around European Union. In summary, there are two methods using both Ultrasonic Extraction and Soxhlet Extraction to achieve the goals for the extraction step. To get comparable results and create less pollution (Inoue et al., 2003; Tsuda et al., 2000), these different pre-processing methods were evaluated while using for simultaneous determination the concentration of Octylphenol ethoxylates, and Nonylphenol ethoxylates in textiles by High-Performance Liquid Chromatography (Jahnke et al., 2004). In this study, the comparisons have been made between the described Soxhlet Extraction and Ultrasonic Extraction. The reproducibility, precision, recovery, and interference issues of these methods were also discussed．