Alkoxylation Ethylene oxide

Alkoxylation Ethylene and/or propylene oxides Alkoxylated castor oils... 

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. 

Alkoxylated polyethyleneimines are obtained by reacting polyethylene-imine with a molecular weight of 2500 to 35,000 with an excess of propylene oxide and ethylene oxide with respect to the ethyleneimine unit in the... 

In general, polyalkylene polyamides-amines are obtained by the condensation of polyalkylenepolyamines with dicarboxylic acids. The materials are alkoxylated with an excess of ethylene oxide or propylene oxide or 1,2-butylene oxide [149],... 

As a general rule, the addition of ethylene oxide to a resin backbone will tend to increase the water solubility of the compound. The addition of propylene oxide or butylene oxide to the resin will tend to increase the hydrocarbon solubility of the compound. Often, the dehazer or demulsifier can be made to perform selectively in oil-water systems by adding both ethylene oxide and propylene oxide to the same molecule. Performance and solubility of the alkoxylated compound can then be finely tuned by closely controlling the amount and order of epoxide addition. A random EO-PO based fuel demulsifier is shown in FIGURE 6-6. 

Linear ethoxylates are tine preferred raw materials for production of ether sulfates used in detergent formulations because of uniformity, high purity, and biodegradahility, The alkyl chain is usually in the C y. to Cy range having a molar ethylene oxide alcohol ratio of anywhere from 1 1 to 7 1. Propoxylates, ethoxylates, and mixed alkoxylates of aliphatic alcohols or alkyl phenols are sulfated for use in specialty applications. 

Alkoxylation. The reaction of alcohols with ethylene oxide gives polymeric products in which many units of the ethoxy group are incorporated (Reaction XXII). The reaction can be controlled... 

It can be seen that it is possible to vary the alcohol chain greatly and the alkoxylate chain can be varied in the same way as with nonylphenol to produce both water and oil soluble products. The major difference between nonylphenol and alcohol ethoxylates is the distribution of ethoxylate chains. The rate constants for the addition of ethylene oxide to primary alcohols are comparable and are essentially the same as for the 1-mol or the 2-mol adduct. These addition products, of course, are still primary alcohols. Thus, if one were making a 2-mol adduct of the alcohol, there would be a fair proportion of free alcohol still present - of the order of 10-20%. Chain growth starts well before all the starting alcohol has reacted and alcohol ethoxylates have therefore a much broader ethoxylate chain distribution than the comparable nonylphenol ethoxylate. It has been shown that ethylene oxide consumption becomes constant after 8 or 9 mol of ethylene oxide per mole of alcohol has been added [10,11]. 

A wide range of products, including every class and type of surfactant, has been found to exhibit demulsification properties. The most commonly used products in lubricant formulations contain anionic surfactants such as alkyl-naphthalene sulphonates. Nonionic alkoxylated alkyl-phenol resins and block copolymers of ethylene oxide and propylene oxide are also used. 

Aminic polyols are low molecular weight adducts of propylene oxide (PO) [and/or ethylene oxide (EO)] made from aliphatic or aromatic polyamines such as ethylenediamine (EDA), diethylene triamine (DETA) [1, 2], ortho-toluene diamine (o-TDA) [3, 4] or diphenylmethanediamine (MDA) [2, 5, 6]. Because these starters are liquid at room temperature (EDA, DETA) or low melting point solids (o-TDA, MDA), they are alkoxylated in the absence of solvents. 

Mannich polyols is a very important group of aromatic polyols obtained by the alkoxylation with propylene oxide (PO) [(and/or ethylene oxide (EO)] of the Mannich bases obtained by classical Mannich reaction between phenols (for example phenol, p-nonylphenol), formaldehyde and alkanolamines (diethanolamine, diisopropanolamine, monoethanolamine, monoisopropanolamine and so on). Synthesis of Mannich polyols is divided into two important steps ... 

The alkoxylation of lignin is possible in a solvent (dimethylformamide, N-methylpyrrolidone or in liquid PO [20]). A process using a lignin-glycerol mixture (3 1) in a polyether polyol based on lignin was developed [20]. The catalysts of this reaction are KOH, but a tertiary amine, such as dimethylaminoethanol is preferred. By alkoxylation with a PO-EO mixture (e.g., 18-25% ethylene oxide EO) a totally liquid dark-brown lignin-based polyether polyol with a viscosity in the range 4,700-8,000 mPa-s at 25 °C, with an hydroxyl number... 

Scientific Design Company, Inc. Alkoxylates Propylene oxide/ethylene oxide and various chain starters Unique reactor - catalyzed liquid phase is finely dispersed into a PO/EO vapor stream 80 2001... 

POE monoesters can be produced by direct interaction of carboxylic acid and ethylene oxide but they contain a large quantity of PEG as by-product [7, 8]. Principally, the carboxylic acid alkoxylation is applied for the monoester production such as glycol stearate and propylene glycol stearate (VI) that show good performance as oil-soluble emulsifiers, emollients and opacifiers in cosmetics. 

The initiation of the polymerization of alkylene oxides with iron has been known for some time. A recent patent extends this concept to the alkoxylation of many active hydrogen compounds. The catalyst for this process is a polycrystalline iron oxide (a-iron(lll)oxide). For example, in an autoclave, under nitrogen, n-decanol and 2 wt% of the iron catalyst are treated with ethylene oxide at a pressure of less than 6 bars for 4 hr. The resulting liquid had a degree of polymerization of 5 [42]. 

In surfactant manufacture, propylene oxide (PO) is employed both as a hydrophobe (see Section 2.3 above), and as a modifier for poly(ethylene oxide). Propylene oxide is similar to EO except that it contains an additional methyl group, which adds steric bulk, and is significantly more hydrophobic in nature. If PO is inserted in the middle of an poly(ethylene oxide) chain, different properties (e.g. greater liquidity) are obtained. Since this approach requires three separate alkoxylations, it is only used when modification of specific properties is required. More common is the use of PO to cap the end of the poly(ethylene oxide) chain. This significantly reduces foaming, which can be critical in certain applications (e.g. machine dishwashing). 

There are many other unitary operations which are used by organic chemistry plants to manufacture synthetic solvents. These include alkoxylation (ethylene glycol), halogenation (1,1,1-trichloethane), catalytic cracking (hexane), pyrolysis (acetone and xylene), hydrodealkylation (xylene), nitration (nitrobenzene), hydrogenation (n-butanol, 1,6-hexanediol), oxidation (1,6-hexanediol), esterification (1,6-hexanediol), and many more. 

Polymeric amido-amine alkoxylated trietylene tetramine Adducts of aliphatic amines with mono- and diepoxides and ketones (i.e. amine-epoxy adducts) Diethylenetriamine-ethylene oxide adduct Ethylene diamine adduct to solid epoxy Triethylenetetramine-propylene oxide adduct... 

Althongh the ethoxylate structure is shown, alcohol alkoxylates can contain nnits of ethylene oxide, propylene oxide, butylene oxide or mixtnres. Alkyl phenol ethoxylates technically are alcohol ethoxylates however, they are discnssed separately below. 

Rigid PUR foam wastes were simultaneously aminolyzed with NH, ethylene diamine, diethylene triamine, hexamethylenediamine, or ethanolamine and alkoxylated by ethylene oxide, propylene oxide, butylene oxide, phenyl glycidyl ether, or styrene oxide optionally in the presence of a hydroxyl containing tert-amine (dimethyl ethanol... 

The products are prepared by the alkoxylation of cetyl alcohol or stearyl alcohol using ethylene oxide or propylene oxide. In the second step, the intermediate is reacted with acryhc acid, meth-acrylic acid or a mixture from these acids. When the esterification is completed, the unreacted acid is distUled off from the product under high vacuum. An additional purification of the ester is not necessary (28). The reaction is shown in Figure 5.4. 

It was during the 1940s that the base-initiated polymerization of propylene oxide began to be used to produce products that are still in use today (14). In a series of patents by H. R. Rife and F. H. Roberts (15), poly (propylene oxide)s are described that are initiated in the presence of alcohols to produce ether propoxylates. These liquid polymers had methoxy or butoxy groups on one end of the poly ether chain and were used as lubricants and hydraulic fluids. This work was quickly followed by other derivatives, which included esters and mixed alkoxylates of propylene oxide and ethylene oxide (16). Uses included antifoams and emulsifiers, coating solvents, ceramic glazes and binders, and synthetic lubricants for internal combustion engines (17). 

Block copolymers of alkylene oxides were introduced as PLURONIC polyols by Wyandotte, now BASF Wyandotte Corporation, in 1951. The first products were made by alkoxylation of propylene glycol with propylene oxide to a molecular weight of about 900, followed by further reaction with ethylene oxide. These products can be generally characterized by the formula... 

Chitin was first swollen by treatment with alkali and then alkoxylated with ethylene oxide under homogeneous (50, 51) or heterogeneous (52) conditions to produce water-soluble polymers. 

Alkoxylated perfluoroalkane sulfonamides have been prepared by reacting aliphatic polyamines with less than the stoichiometric amount of a perfluoroalka-nesulfonyl fluoride and alkoxylating the reaction product with ethylene oxide or propylene oxide [233] ... 

Alkoxylation with ethylene oxide of the OH groups of c. leads to a group of nonionic - surfactants, used as - foamers and defoamers in detergents, lubricating oils and cutting fluids. Propoxy-lated c. serves in lubricants and as a polyurethane polyol. In the USA, 6500 mt of alkoxylated c. were produced in 1988. 

H. is produced by - alkoxylation of alkali-cellulose suspended in solvents, such as acetone, isopropanol or tcrt.butanol 0.8-1.5 moles of alkali per AGU are necessary. To decrease viscosity, the alkali-cellulose is degraded by aging (- cellulose) before reaction or by adding hydrogen peroxide to the alkaline reaction mixture. For better efficiency, the addition of ethylene oxide is carried out in two stages. After the first reaction step, only catalytic amounts of alkali are necessary. Reaction takes place in 1-4 h at 30-80 °C and is stopped by neutralization with hydrochloric or acetic acid. Salts are removed by washing with alcohol/water mixtures. If retarded dissolution in water is desired, the wet product is treated with glyoxal. 

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