Ethylene oxide adduct

Furfuryl alcohol is used alone or in combination with other solvents for various cleaning and paint removing operations. The ethylene oxide adduct of furfuryl alcohol is especially useful in this type of appHcation (80—83). 

Since double bonds are no longer present, these compounds are more stable than the corresponding furan derivatives. Tetrahydrofurfuryl alcohol—ethylene oxide adducts [31692-85-0] are also usehil solvents for paint stripping formulations (136,141,143). 2-Methylfuran is a good solvent, but... 

The product secondary alcohols from paraffin oxidation are converted to ethylene oxide adducts (alcohol ethoxylates) which are marketed by Japan Catalytic Chemical and BP Chemicals as SOFTANOL secondary alcohol ethoxylates. Union Carbide Chemical markets ethoxylated derivatives of the materials ia the United States under the TERGlTOL trademark (23). 

Another subclass of substituted amides that is of great commercial value is the ethoxylated amides. They can be synthesized from alkanolamides by chain extending with ethylene or propylene oxide or by ethoxylation directly from the primary amide (46—48). It was originally beheved that the stepwise addition of ethylene oxide (EO) would produce the monoethano1 amide and then the diethanolamide when sufficient ethylene oxide was added (49), but it has been discovered that only one hydrogen of the amide is substituted with ethylene oxide (50—53). As is typical of most ethylene oxide adducts, a wide distribution of polyethylene oxide chain length is seen as more EO is added. A catalyst is necessary to add ethylene oxide or propylene oxide to a primary or an ethoxylated amide or to ethoxylate a diethoxy alkanolamide synthesized from diethanolamine (54). 

Heating the adduct of ethylene oxide and sulfur dioxide with primary alcohols in the presence of alkaH hydhdes or a transition-metal haHde yields dialkyl sulfites (107). Another method for the preparation of methyl alkyl sulfites consists of the reaction of diazomethane with alcohoHc solutions of sulfur dioxide (108). 

Ethoxyl tion. Base-cataly2ed ethoxylation of aUphatic alcohols, alkylphenols, and fatty acids can be broken down into two stages formation of a monoethoxy adduct and addition of ethylene oxide to the monoadduct to form the polyoxyethylene chain. The sequence of reactions is shown in equations 20—22 ... 

Typical commercial ethoxylated sorbitan fatty acid esters are yellow Hquids, except tristearates and the 4- and 5-mol ethylene oxide adducts which are light tan soHds. These adducts, as well as the 20-mol adducts of the triesters, are insoluble but dispersible in water. The monoester 20-mol adducts are water soluble. Ethoxylated sorbitan esters are widely used as emulsifiers, antistatic agents, softeners, fiber lubricants, and solubilizers. In combination with the unethoxylated sorbitan esters or with mono- or diglycetides, these are often used as co-emulsrfiers. The ethoxylated sorbitan esters are produced by beating sorbitan esters with ethylene oxide at 130—170°C in the presence of alkaline catalysts. 

Surfactants and Dispersants. Castor od can be transformed from an od- to a water-soluble surfactant, depending on the moles of ethylene oxide added to its hydroxyl group. A 40 mole ethylene oxide adduct of castor od, known as PEG-40 castor od, is a surfactant that has cosolvent properties and is utilized as a fragrance solubilizer (118). Glycol hydroxystearate emulsifiers are formulated into shampoos to impart finer peadescence and give better stabdity than gylcol stearates (118) (see Hair preparation). 

DET-ethylene oxide adduct 20 16 min room temp. reduced 92 minimum irriation —... 

Clear, surface-active phosphate ester compositions were prepared by heating 1 mol P4O,0 with 2-4.5 mol of a linear or branched chain C6, 8 saturated alcohol, a C4 20 mono- or dialkylphenol, or a 2- to 14-mol ethylene oxide adduct of one of these alcohols or alkylphenols at 25-110°C, and hydrolyzing the reaction product at 60-110°C with 0.5-3.0% H20. The hydrolyzed mixture had a lower Klett color value than the phosphorylation reaction mixture [21]. 

Phosphoric acid esters based on alkylene oxide adducts are of great interest. Their properties can be altered by the length and structure of the hydrophobic alkyl chain. But they are also controlled by the kind and length of the hydrophilic alkyleneoxide chain. The latter can easily be tailored by selection between ethylene oxide and propylene oxide and by the degree of alkoxylation. 

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]. 

Whereas nonionic ethylene oxide adducts discolor badly on contact with sodium hydroxide, phosphate derivatives of these nonionics exhibit good color stability even under these conditions. But in the presence of strong acids poly-oxyethylated phosphate esters undergo hydrolysis to the base nonionic and phosphoric acid. However, the free surface-active acids by themselves show little tendency to hydrolyze. They have a pH value of 2 in aqueous solution. 

Phosphoric acid esters are strong acids similar to orthophosphoric acid. Potentiometric titration of a 0.1 N aqueous solution of an acid phosphoric acid ester clearly shows two potential jumps which lie at pH values of 6.5 and 11.5. The pH value of diluted aqueous solutions of acid esters lies in the range of 1-3. Phosphoric acid esters are stable against hydrolysis, but adducts of free phosphoric acid esters with ethylene oxide are generally less stable. 

Ethylene oxide adducts of alkanephosphonic acids exhibit a better solubility in water and partly an interesting depression of the surface tension in aqueous solutions (Table 9). Although foamability and wetting rate lie in a medium range, they possess no emulsifying ability. 

Reacting a high-molecular-weight polyalkylene glycol (PAG) with ethylene oxide (EO) to form a PAG/EO adduct... 

Griffin studied primarily ethylene oxide (EO) adducts and routinely substituted % EO for % hydrophile. Since that time, the HLB system has become very popular, especially to characterize emulsifying agents. (The reader is referred to sec. V.B. for a more detailed discussion of the use of the HLB system for the identification of adequate emulsifiers and combinations thereof.)... 

Although there are other types of nonionic surfactant, the great majority are adducts of ethylene oxide with hydrophobes derived from three sources ... 

Whereas the alcohol and phenol derivatives are characterised by ether linkages, adducts of ethylene oxide with fatty acids give rise to both monoesters (9.45) and diesters. These are... 

Adducts of ethylene oxide with fatty amines can yield mono- (9.46) or di-substituted (9.47) products, as can the adducts with fatty amides (9.48, 9.49). In practice the products formed are far from being as simple or as symmetrical as represented by these formulae since, amongst other things, the ethylene oxide addition takes place randomly. 

This is a very important group of products and most of them are adducts of long-chain alcohols or alkylphenols with a number of ethylene oxide (EO) units. Adducts with propylene oxide (PO) and copolymers of ethylene and PO are also used although they are less important in terms of usage volume than the pure ethoxylate derivatives. 

Scheme 8.13 and Eqs. 8.6-8.10 reveal that lithiated methoxyallene 42 is sufficiently reactive towards a variety of electrophiles such as alkyl halides [44, 45], ethylene oxide [12c], tosylated aziridine 45 [46], dimethyl disulfide [12b], trialkylstannyl and trialkylsilyl chlorides [47, 48] and iodine [49]. These substitution reactions proceed with excellent regioselectivity and the corresponding a-functionalized products are obtained in good to high yields. An exceptional case was found by treatment of 42 with a guanidinium salt, which led to a 60 40 mixture of a- and y-adducts 50 and 51 (Eq. 8.11) [50],... 

Nonionic surfactants contain (Fig. 23) no ionic functionalities, as their name implies, and include ethylene oxide adducts (EOA) of alkylphenols and fatty alcohols. Production of detergent chain-length fatty alcohols from both natural and petrochemical precursors has now increased with the usage of alkylphenol ethoxylates (APEO) for some applications. This is environmentally less acceptable because of the slower rate of biodegradation and concern regarding the toxicity of phenolic residues [342]. 

From a physical chemical viewpoint, oxyethylene groups located adjacent to the ionic sulfate group may be considered at the first glance as additional hydrophilic groups, in analogy to nonionic ethylene oxide (EO) adducts. 

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