Phenol ethoxylates, alkyl

These were probably the first ethoxylates produced in large quantities and were important from the mid- 1940s. They were largely based on nonylphenol with much smaller quantities of octyl and dodecylphenol derivatives. The first mole of ethylene oxide adds with relative ease to the alkyl phenol and then additional moles of ethylene oxide add to produce a Poisson distribution certainly up to the 10-mol derivative [8, 9]. 

Production of a 9-mol nonylphenol ethoxylate is carried out at 130-150°C as described in Section 5.2. The importance of water removal from the feedstock can be seen in Table 5.1. 

Derivatives of nonylphenol up to about the 12-mol ethoxylate are liquid at ambient temperature and do not require heated storage. They are used for reducing oil-water interfacial tension and are excellent for removing oily soils. The major drawback is the biodegradation resistance of the benzene ring, which limits the use to industrial applications in which waste can be treated before any discharge to waterways. However, their relative cheapness has maintained their use in some formulations destined for the household market in certain parts of the world. 

As can be seen from Table 5.2, nonylphenol ethoxylates have a steeply increasing cloud point for very little addition of ethylene oxide. Most industrial products have a rounded up/down value of ethylene oxide in their nomenclature. Thus, NP9 from one company could be actually NP9.25 and from another could be NP8.75. The cloud point for these two products could be 15° C different and in some applications, such as in solubilisation of a fragrance or flavouring, this could be crucial. This is almost certainly due to the sharp (compared to alcohol-based products) Poisson isomer distribution and also variable polyethylene glycol levels in different manufacturers products. Therefore, it is suggested that product should always be purchased on a cloud point specification and not to an EO number. 

With the slow demise of the nonylphenol ethoxylate market due to legislation, the fatty alcohol market has the chance to design alternatives by subtle changes to the hydrophobe chain lengths and alkoxylate levels. The effects must be achieved with biodegradability as 

These are prepared by the reaction of EO with an appropriate alkyl phenol. The most common surfactants of this type are those based on nonyl phenol they are cheap to produce but suffer from problems of biodegradability and potential toxicity (the byproduct of degradation is nonyl phenol, which is considerably toxic in fish and mammals). Despite these problems, nonyl phenol ethoxylates are still used in many industrial properties, due mainly to their advantageous properties such as 

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Besides the use of anionics such as sulfonates and nonionics such as alkyl-phenol ethoxylates, in 1977 the use of ether carboxylates was also described [183] in terms of its excellent temperature, electrolyte, and hard water stability and low interfacial tension, especially in case of the C12-C14 ether carboxylic acid with 4.5 mol EO. 

Sun, C. and Baird, M. (1998). The determination of alkyl phenol ethoxylates in wool-scouring effluent. Journal of the Textile Institute 89, 677-685. 

Alkyl orthophosphate triesters, 79 41 terteAlkyl peroxycarbamates, decomposition of, 78 486 Alkyl peroxyesters, 78 478-487 chemical properties of, 78 480 487 physical properties of, 78 480 primary and secondary, 78 485 synthesis of, 78 478-480 synthetic routes to, 78 479 tert-Alkyl peroxyesters, 78 480 84, 485 as free-radical initiators, 74 284-286 properties of, 78 481-483t uses of, 78 487 Alkylperoxy radical, 74 291 Alkyl phenol ethoxylates, 8 678, 693 ... 

The foregoing is in line with earlier work which showed that acclimated river water degraded an alkyl phenol ethoxylate when measured by foam volume reduction(11a). 

SAE can be generally utilized as biodegradable detergents or surfactants for many industries in which the conventional alkyl-phenol ethoxylates have been used. 

The most common nonionic surfactants are those based on ethylene oxide, referred to as ethoxylated surfactants. Several classes can be distinguished alcohol ethoxylates, alkyl phenol ethoxylates, fatty acid ethoxylates, sorbitan ester ethoxylates, fatty amine ethoxylates, and ethylene oxide-propylene oxide copolymers (sometimes referred to as polymer surfactants). Another important class of nonionics are the multihydroxy products such as glycol esters, glycerol (and polyglycerol) esters, glucosides (and polyglucosides), and sucrose esters. Amine oxides and sulfinyl surfactants represent nonionic with a small head group. 

DeForest Enterprises Inc. DelONIC Series Alkyl phenol ethoxylates... 

ABS—Alkylbenzene sulfonate AE—alcohol ethoxylate AES—alkyl ether sulfonate AOS—alpha olefin sulfonate APE—alkyl phenol ethoxylate APG—alkyl polyglycoside AS—alkyl sulfate... 

Surfactants Ionic, anionic (e.g., sodium dodecyl sulphate, Cj2H250S03 Na ), cationic (e.g., cetyl trimethyl ammonium chloride, Ci,H33-N+(CH3)3C1-), zwitterionic [e.g., 3-dimethyldodecylamine propane sulphonate (betaine CJ2H25-N" (CH3)2-CH2-CH2-CH2-S03)], nonionic, alcohol ethoxylates C H2 +i-0-(CH2-CH2-0) -H, alkyl phenol ethoxylates C H2 +i-CgH4-0-(CH2-CH2-0) -H, amine oxides (e.g., decyl dimethyl amine oxide, C10H21-N ( 113)2 0), and amine ethoxylates. 

Alkyl phenol ethoxylates have been over many years the workhorses as nonionic emulsifiers for emulsion polymerization. Depending on availability and price of buten and propen, nonyl (tripropylene)phenol ethoxylates or octyl (dibutylene) phenol ethoxylates have been very broadly used, whereas dodecyl (tetrapropylene or tributylene)phenol and tri tert-butylphenol ethoxylates were merely regarded as specialties. These aUcyl phenol ethoxylates can also be used as intermediates for the synthesis of anionic alkyl phenol ether sulphates. Sulphation by chlorosul-phonic acid or sulphur trioxide besides formation of the ether sulphate end group inevitably leads to certain amounts of ring sulphonation in the phenyl group, whereas amidosulphonic acid gives sulphonate-free aUcyl phenol ether sulphate ammonium salts. 

Alkyl phenol ethoxylates can also react with P4O10 yielding alkyl phenol etherphosphates as a mixture of mono-/diesters or with maleic anhydride to yield maleic acid monoesters, which then react with NaHS03 to yield sulphosuccinate monoesters. Alkylphenolpolyglycolether sulphates, phosphates or sulphosuccinates are mainly used as primary anionic emulsifiers for the manufacturing of acrylic, styrene/acrylic or vinyl acetate co-polymer dispersions. Another type of non-ionic emulsifier is block copolymers of ethylene oxide with propylene oxide. 

Alkyl Phenol Ethoxylates (APE) Degradable [65], [66], [67] Partially degradable [68] ... 

In contrast to alkyl phenol ethoxylates the class of fatty alcohol ethoxylates is biodegradable and eco-friendly. Efficient technical surfactants found in this class are Lutensol XL 700, Lutensol T08, Lutensol A07, Lutensol AO8 and Eusapon OD. The phase behaviour was characterised in systems of type H20/NaCl-suet-technical non-ionic surfactant. The salt mass fraction was kept constant at = 0.10 and the oil volume fraction at = 0.50. In view of the degreasing process, which is conducted at 30°C, the X-point of the optimal system should be located around 30°C and the formation of the highly viscous La-phase should be suppressed. Figure 10.5 presents the T-y cuts for the respective systems. 

Emulsifier 632/90%. [Ethox] Modified alkyl phenol ethoxylate low-foam surfactant dispersant... 

Solvent Scour. [Hart Chem. Ltd.] Alka-nolamides and alkyl phenol ethoxylate scouring agent... 

Surfactants (nonionics) Ethoxylated alkyl-phenols Ethoxylated fatty alcohols... 

Hyonic . [Henkel/Emery Henkel Canada] Alkyl phenol ethoxylates detergent, wetting agent, ermilsifier, penetrant for household and industrial cleaners, agric. chemicals, corrosion inhibitors, textiles, food applies. intermediate. 

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