Esters industrial uses

Helmut Orth first reported the use of laetones to accelerate phenolic resole cure in 1957 [161]. A year later, Orth discovered that this effect could be extended to aliphatic esters as well [162], Despite the dramatic nature of the acceleration seen, Orth s observations were not applied in industry for a decade. In 1967, Sumitomo and BASF applied esters to soil grouting and wood uses [133,163, 164]. Neither of these applications were commercially successful, however, and commercial success would not occur until 1980 when Borden introduced ester-cured sand binders for foundry [165]. This technology was highly successful in UK and spread to the US, where it was applied immediately to foundry in 1981 and eventually to wood products in 1990 [119,166-173]. Esters are capable of reducing the gel times of resoles from several weeks to less than 30 s at room temperature. Both gaseous and liquid esters are applicable [119,166]. 

Environmental Protection Agency (1999a) Methods for organic chemical analysis of municipal and industrial wastewater. Method 606 - Phthalate ester. US Code Fed. Regul., Title 40, Part 136, App. A, pp. 91-101... 

The general formula for boric acid esters is B(OR)3. The lower molecular weight esters such as methyl, ethyl, and phenyl are most commonly referred to as methyl borate [121 -43-7], ethyl borate [150-46-9], and phenyl borate [1095-03-0], respectively. Some of the most common boric acid esters used in industrial applications are Us ted in Table 1. The nomenclature in the boric acid ester series can be confusing. The IUPAC committee on boron chemistry has suggested using thalkoxy- and triaryloxyboranes (5) for compounds usually referred to as boric acid esters, trialkyl (or aryl) borates, trialkyl (or aryl) orthoborates, alkyl (or aryl) borates, alkyl (or aryl) orthoborates, and in the older literature as boron alkoxides and aryloxides. Cyclic boric acid esters, which are trimeric derivatives of metaboric acid (HB02), are known as boroxines (1). 

Benzyl alcohol is primarily used as a solvent and an antimicrobial preservative, but it has also found use as an antiseptic and local anesthetic. It is also used as a raw material of various esters, used in the soap, perfume, and flavor industries. Acceptable daily intakes were established at 5 mg kg for benzyl alcohol by the World Health Organization. In 1998, benzyl alcohol was reported by the US Food and Drug Administration as being used in 322 cosmetic formulations, belonging to 43 cosmetic categories. 

Epichlorohydrin or chloromethyloxirane is manufactured from allyl chloride, and, in 2006, had a merchant price of US 1.66 kg [4]. It is used as a building block in the manufacture of plastics, epoxy resins, phenoxy resins, and other polymers, and as a solvent for cellulose, resins, and paints, and has also found use as an insect fumigant. Epoxy resins (aryl glycidyl ethers) are manufactured successfully in large scale (1.2 x 10 metric tons in 2000) [26] and are widely used in a variety of industrial and commercial applications [27]. These are made by addition reactions of epichlorohydrins or by epoxidation of allyl ethers or esters (Table 1.1). Epichlorohydrin can be reacted with an alkali nitrate to produce glycidyl nitrate, an energetic binder used in explosive and propellant compositions. 

Harada, K., Matsushita, A., Sasaki, H., and Kawachi, Y, Improved preparation of optically active phosphinyl-containing oxyglutaric acid ester derivatives, Ube Industries, U.S. Patent Appl. US 5717124, 1998 Chem. Abstr, 128, 167563, 1998. 

The pioneering synthetic work quickly led to the synthesis of carotenoids on an industrial scale. The industrial production of p,p-carotene (3) began in 1954, only four years after its first synthesis on a laboratory scale. This extremely rapid development was made possible by the enthusiasm and perseverance of Isler and his colleagues at Roche in Basel. Since then, commercial synthesis of carotenoids has continuously advanced and today the two major industrial producers Roche and BASF produce six different carotenoids, namely p,p-carotene (3), canthaxanthin (380), optically inactive astaxanthin (403) and the apocarotenoids 8 -apo-p-caroten-8 -al (482), 8-apo-p-caroten-8 -oic acid (486) ethyl ester, and citranaxanthin (466). The total annual sale is now in the region of US 300 million, and the commercially produced carotenoids are used mainly as food and feed additives. 

Y. Fujita and O. Sawa, Ester compound, plasticizer for biodegradable aliphatic polyester resin, and biodegradable resin composition, US Patent 7166654, assigned to Daihachi Chemical Industry Co., Ltd. (Osaka, JP), January 23, 2007. 

The acid derivatives deserve our full attention. They are all around us in life. Esters are of utmost importance to the fragrance and flavoring industry. The sweet odors of fruits and perfumes are usually a result of volatile esters. Amides are found throughout biochemistry. It is the amide group that defines enzyme structure, which in turn defines us. We will cover more of the bio-organic chemistry of amides in Chapter 23. 

Figure 13.1 Acrylic acid and esters demand in USA in 1995 versus 2000 (From US Outlook Acrylic Acid and Derivatives with Forecasts to 2006 and 2011. Freedonia Industry...

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