Glycols, Epoxides

T0144 Cams Chemical Company, CAIROX Potassium Permanganate 

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Propylene Glycol Monoethyl Ether Acetate (PGMEA) Glycols, Epoxides Gold... 

SOURCE K. Emoto, J. M. Harris, and M. Van Alstine, Grafting Polyfethylene glycol) Epoxide to Amino-Derivatized Quartz Effect of Temperature and pH on Grafting Density," AnaLChem. 1996.68, 375E... 

Oleic acid, 1,2-propylene glycol epoxidized ester. 

EINECS 271-842-6 9-Octadecenoic acid (Z)-, epoxidized, ester with propylene glycol Oleic acid, 1,2-propylene glycol epoxidized ester Vikoflex49M. 

Dowanol PM Monoethyl Ether Propylene Glycol Epoxidized Oils Epoxidized Vegetable Oils... 

K. Emoto, J.M. Harris, J.M. Van Alstine, Grafting poly(ethylene glycol) epoxide to amino-derivatized quartz effect of temperature and pH on grafting density. Anal. Chem., 68 (21) ... 

The epoxides may be converted into 1 2-glycols by hydrolysis. In some cases the 1 2-glycol may be produced directly by carrying out the epoxidation in the presence of water. If the 1 2-glycol is desired, it is usually better to employ performic acid or peracetic acid, the latter best in the presence of a trace of sulphuric acid. An epoxide is first formed, followed by the hydroxy-formate or hydroxy-acetate, and ultimately the 1 2-glycol ... 

Regioselectivity of C—C double bond formation can also be achieved in the reductiv or oxidative elimination of two functional groups from adjacent carbon atoms. Well estab llshed methods in synthesis include the reductive cleavage of cyclic thionocarbonates derivec from glycols (E.J. Corey, 1968 C W. Hartmann, 1972), the reduction of epoxides with Zn/Nal or of dihalides with metals, organometallic compounds, or Nal/acetone (seep.lS6f), and the oxidative decarboxylation of 1,2-dicarboxylic acids (C.A. Grob, 1958 S. Masamune, 1966 R.A. Sheldon, 1972) or their r-butyl peresters (E.N. Cain, 1969). 

Ethylene glycol and propy lene glycol are prepared industrially from the corre spending alkenes by way of their epoxides Someapplica tions were given in the box in Section 6 21... 

Esters. The monoisobutyrate ester of 2,2,4-trimethyl-1,3-pentanediol is prepared from isobutyraldehyde ia a Tishchenko reaction (58,59). Diesters, such as trimethylpentane dipelargonate (2,2,4-trimethylpentane 1,3-dinonanoate), are prepared by the reaction of 2 mol of the monocarboxyhc acid with 1 mol of the glycol at 150—200°C (60,61). The lower aUphatic carboxyHc acid diesters of trimethylpentanediol undergo pyrolysis to the corresponding ester of 2,2,4-trimethyl-3-penten-l-ol (62). These unsaturated esters reportedly can be epoxidized by peroxyacetic acid (63). 

Glycols and epoxides react with maleic anhydride to give linear unsaturated polyesters (61,62). Ethylene glycol and maleic anhydride combine to form the following repeating unit. This reaction is the first step in industrially important polyester resin production (see Polyesters, unsaturated). 

Homopolymers of PO and other epoxides are named a number of ways after the monomer, eg, poly(propylene oxide) (PPO) or polymethjioxirane from a stmctural point of view, polyoxypropylene or poly(propylene glycol) or from the Chemicaly hstracts (CA) name, poly[oxy(methyl-l,2-ethanediyl)], a-hydro- CO-hydroxy-. Common names are used extensively in the Hterature and in this article. 

Specialty Epoxy Resins. In addition to bisphenol, other polyols such as aUphatic glycols and novolaks are used to produce specialty resins. Epoxy resins may also include compounds based on aUphatic, cycloaUphatic, aromatic, and heterocycHc backbones. Glycidylation of active hydrogen-containing stmctures with epichlorohydrin and epoxidation of olefins with peracetic acid remain the important commercial procedures for introducing the oxirane group into various precursors of epoxy resins. 

Ethylene oxide (qv), propylene oxide (qv), butylene oxide, and other epoxides react with ethanol to give a variety of Uquid, viscous, semiwax, and soUd products. These products are used ia the coatings iadustry as solvents, and as paints, antioxidants, corrosion inhibitors, and special-purpose polymers. Recent concerns about the health effects of ethanol containing glycol ethers have led to the decline in the production of these compounds. 

Thallium-Catalyzed Epoxidation Process. The use of Tl(III) for olefin oxidation to yield glycols, carbonyls, or epoxides is weU known... 

TiPSON - COHEN Oleflnatlon Conversion o( sugar glycols via epoxides into sugar olefins. 

Epoxidation of the olefin, 36, affords 40. Solvolysis of the latter in dry formic acid gives a mixture of the desired product, 42 (both a and 3 hydroxyl at 15), as well as a mixture of the glycols (41). Solvolytic recycling of the mixture in the same medium affords eventually about a 45% yield of the product. 

Replacement of the carbamate function by an amide seems to be compatible with meprobamate-like activity in a compound formally derived from a 1,2-glycol. Oxidation of the commercially available aldehyde, 22, under controlled conditions affords the corresponding acid (23). This is then converted to its amide (24) via the acid chloride. Epoxidation by means of perphthalic acid affords oxanamide (25). ... 

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