Hydroxy acids propylene oxide

Hydrogen Sulfide andMercaptans. Hydrogen sulfide and propylene oxide react to produce l-mercapto-2-propanol and bis(2-hydroxypropyl) sulfide (69,70). Reaction of the epoxide with mercaptans yields 1-aLkylthio- or l-arylthio-2-propanol when basic catalysis is used (71). Acid catalysts produce a mixture of primary and secondary hydroxy products, but ia low yield (72). Suitable catalysts iaclude sodium hydroxide, sodium salts of the mercaptan, tetraaLkylammonium hydroxide, acidic 2eohtes, and sodium salts of an alkoxylated alcohol or mercaptan (26,69,70,73,74). 

Jacobsen (1999) has carried out carbomethoxylation of asymmetric epoxides. Thus, the carbomethoxylation of (R)-propylene oxide with CO and methanol yields 92% of (3R)-hydroxybutanoic acid in greater than 99% ee. Similarly, the reaction of (/ )-epichlorohydrin gives 96% of 4-chloro-(3R)-hydroxybutanoic acid in greater than 99% ee. The catalyst consists of dicobalt octacarbonyl and 3-hydroxy pyridine. A continuous process for making enantiomeric 1-chloro-2-propanol has been suggested. With a suitable catalyst propylene reacts with O2, water, cupric and lithium chloride to give 78% of (S)-l-chloro-2-propanol in 94% ee. 

The pendant hydroxy groups of ethylene oxide-propylene oxide copolymers of dihydroxy and trihydroxy alcohols may be sulfurized to obtain a sulfurized alcohol additive. This is effective as a lubricant in combination with oils and fats [387,533]. The sulfurized alcohols may be obtained by the reaction of sulfur with an unsaturated alcohol. Furthermore, fatty alcohols and their mixtures with carboxylic acid esters as lubricant components [1286] have been proposed. 

The optically active glycols are a convenient starting material for the preparation of optically active carbinols, hydroxy-acids, etc. The biological method of asymmetric reduction is perhaps the only convenient method for the preparation of these glycols. The steps in the preparation of other optically active glycols arc identical with those of /-propylene glycol. In some cases it is found convenient to oxidize the chlorohydrin to the... 

Suitable starting compounds are polyesters from poly(ethylene oxide) and adipic acid, also poly(propylene oxide) or poly(oxytetramethylene) with molecular weights around 2,000, whose hydroxy end groups can be reacted with very... 

Hydroxy functional methacrylates are accessible by the reaction of melhacryltc acid and ethylene oxide or propylene oxide in the presence of chromium, iron, or ion-exchange catalysts. 

The polymerization is said to be fast with a low energy input, is not inhibited by air, uses no solvents, is nonpolluting, and uses inexpensive materials. The photopolymerization of various epoxidized oils and terpenes also does this. The propenyl ethers were made by isomerization of the corresponding allyl ethers with a ruthenium catalyst. The allyl ethers were made from the hydroxy compounds with allyl bromide and base, a process that produces waste salts. It is possible that the monomers could be made by reaction of the hydroxy compounds with propylene oxide followed by dehydration so that no waste salts would be formed. Isosorbide is made by the acid-catalyzed dehydration of sorbitol, in turn, obtained by the reduction of glucose. 

Several other methodologies have been employed for the synthesis of hydroxy-lated TSILs. 2-Hydroxypropyl-fiinctionalized imidazolium salts have been prepared in excellent yields by the reaction of protonated 1-methylimidazole with propylene oxide, the acid providing the anionic component of the resultant ionic liquid (Scheme 5.5-4) [22]. 

The MALDI spectrum of a pure polymer resembles a comb and the spacing between the comb s teeth equals the mass, Tr, of the repeat unit. This quantity is often diagnostic and it suggests an almost trivial use of MALDI, namely spectral identification of polymers. The reason is that if one computes LIr values for common polymers, most values are different, the number of superpositions being very low. For instance, the most common polyethers are poly (ethylene oxide), poly (propylene oxide), poly(tetrahydrofuran), and poly(2,5-dimethyl phenylene oxide), and some common aliphatic polyesters are poly(caprolactone),poly(lactic acid), poly (hydroxy-butyrate), and poly(hydroxyvalerate). No superposition occurs (Pr values are 44, 58, 72, 120, 114, 72, 86, and 100 Da, respectively). 

Examples of B chains for 0/W emulsions are polystyrene, poly(methyl methacrylate), poly(propylene oxide) and alkyl poly(propylene oxide). For the A chain(s), poly(ethylene oxide) (PEO) or poly(vinyl alcohol) are good examples. Eor W/O emulsions, PEO can form the B chain, whereas the A chain(s) could be poly(hydroxy stearic acid) (PHS), which is strongly solvated by most oils. 

Dimethylsiloxane/glycol copolymer. See Dimethicone copolyol Dimethylsiloxane, hydroxy-terminated. See Dimethiconol Dimethylsiloxane, polymer wKh oxirane and/or methyl oxirane, sulfuric acid ester, ammonium salts. See Ammonium dimethicone copolyol sulfate Dimethylsiloxane (propylene oxide-ethylene oxide) block copolymer. See Di-methylsiloxane/EO-PO copolymer... 

Fig. 9.59 Plot of temperature of maximum spherulite growth rate, Tmax, against equilibrium melting temperature. I m, for indicated polymers. (1) isotactic poly(styrene) (a) (2) poly(tetramethyl-p-silphenylene siloxane) (b) (3) poly(cis-isoprene) (c) (4) poly(caproamide) (d,e) (5) poly(L-lactic acid) (f) (6) poly(phenylene sulfide) (g,h) (7) poly(R-epichlorohydrin), poly(S-epichlorohydrin), poly(I-RS-epichlorohydrin) (i) (8) poly(ethylene terephthalate) (j,k,l) (9) poly(aryl ether ether ketone) (m,n) (10) poly(ethylene-2,6-naphthalene dicarboxylate) (n) (11) poly(3-hydroxybutyrate) (o) (12) isotactic poly(methyl methacrylate) (q) (13) poly(dioxolane) (r) (14) New TPI poly(imide) (s) (15) poly(methylene oxide) (t) (16) poly(cis-butadiene) (u) (17) poly(propylene oxide) (v,w) (18) poly(imide) BPDA - - 134 APB (x) (19) poly(imide) BPDA - -C12 (x) (20) syndiotactic poly(propylene) (y) (21) poly(3-hydroxy valerate) (z) (22) poly(ethylene succinate) (aa) (23) poly(aryl ether ketone ketone) (bb) (24) poly(phenylene ether ether sulfide) (cc) (25) poly(tetramethylene isophtha-late) (dd) (26) poly(hexamethylene adipamide) (e,ee) (27) poly(tetrachloro-bis-phenol-A adipate) (fQ nylon 6-10 (ee).

ID) By hydrogen peroxide. Oxidative ring cleavage of propylene euJfide with 30% hydrogen peroxide baa afforded 2-hydroxy I-pr paiK>-sulfonic acid and sulfuric add as the only identified products 11 ... 

This technology could also be applied for the oxidation of methane (70 °C, 5 Mpa) to formic acid (46% selectivity based on hydrogen peroxide). Another catalyst which can be applied for the direct oxidation of benzene with H202 is the TS-1 catalyst, as described above for propylene epoxidation [41]. Conversion is generally kept low, because introduction of a hydroxy group activates the aromatic nucleus to further oxidation to hydroquinone, catechol and eventually to tarry products [137]. 

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