Acrylic acid manufacture

The technology of the acrylic acid manufacturing process developed in Japan has been disclosed.1354... 

Whey permeate may also be fermented anaerobically to fuel gas. Studies have also been reported on the production of ammonium lactate by continuous fermentation of deproteinized whey to lactic acid followed by neutralization with ammonia. Conversion of whey and whey permeate to oil and single-cell protein with strains of Candida curvata and Trichosporon cutaneum have been examined. Production of the solvents n-butanol and acetone by Clostridium acetobutylicum or C. butyricum is under investigation in New Zealand. Whey permeate also has potential for citric acid and acrylic acid manufacture. Extracellular microbial polysaccharide production from whey permeate has... 

Recent estimates of the atmospheric loading rate of acrolein from sources in the United States were not located. Anderson (1983) estimated the total loading rate of acrolein in 1978 to be 91,450 pounds from facilities involved in its production and use as a chemical intermediate. Loading rates from various industrial sources were as follows acrylic acid manufacturers, 15,175 pounds refined acrolein and glycerin manufacturers, 55,660 pounds methionine manufacturers, 18,150 pounds and miscellaneous intermediate uses, 2420 pounds. These loading rates were based on a total production volume of 350 million pounds for acrolein in 1978, with 87% of this volume consumed in the production of acrylic acid and its derivatives. 

Ans. All the factors listed in Section 1.4, especially catalyst separation. The relative cost and availability of ethylene and propylene also need to be considered. For a history of acrylic acid manufacturing routes, see the reference given in the answer to Problem 6. 

For more than decades, acrylic acid has served as an essential building block in the production of some of our most commonly used industrial and consumer products. Approximately two-thirds of the acrylic acid manufactured in the United States is used to produce acrylic esters - methyl acrylate, butyl acrylate, ethyl acrylate, and 2-ethylhexyl acrylate -which, when polymerized, are ingredients in paints, coatings, textiles, adhesives, plastics, and many other applications. The remaining one-third of the acrylic acid is used to produce polyacrylic acid, or cross-linked polyacrylic acid compounds, which have been successfully used in the manufacture of hygienic... 

In addition, the large number of Chinese players in several industry segments often results in sub-scale plants with inefficient operations. The average plant size of an acrylic acid manufacturer in China, for instance, is less than one-seventh of the average size of corresponding plants in advanced markets. 

The substitution of propylene by propane as the feedstock in the current industrial process for acrylic acid manufacture would lead to many advantages " i) propane is cheaper than propylene ii) only one step would be required in contrast to the current two-step process used in industry and iii) the CO2 emissions from the global process would be lower if propane were used. Thus, taking into account the former advantages of the process from alkane, it is indeed interesting to consider substituting the current acrylic acid process in the near future. 

Valuable products are produced from the oxidation of both ethylene and propylene (Figs. 1 and 2). Ethylene is epoxidized with oxygen in the vapor phase over a silver catalyst, and propylene is epoxidized with an alkyl hydroperoxide in the liquid phase using a molybdeniim catalyst system. Vinylic oxidation products or their stable isomers, including acetaldehyde, acetone, and vinyl acetate, have been manufactured by a series of related catalytic reactions. These reactions occur either in solutions of palladium complexes or on the surfaces of supported palladium catalysts. Bismuth molybdate is an effective catalyst for allylic oxidations of propylene, which are of paramount importance to the chemical industry. Propylene is oxidized in the vapor phase to give acrolein for acrylic acid manufacture or, in the presence of ammonia, to give acrylonitrile. Second- and third-generation catalysts,... 

CHi=CMeCOOH. Colourless prisms m.p. 15-16 C, b.p. 160-5 C. Manufactured by treating propanone cyanohydrin with dilute sulphuric acid. Polymerizes when distilled or when heated with hydrochloric acid under pressure, see acrylic acid polymers. Used in the preparation of synthetic acrylate resins the methyl and ethyl esters form important glass-like polymers. 

CHjlCH COOH. Colourless liquid having an odour resembling that of ethanoic acid m.p. 13 C, b.p. I4I°C. Prepared by oxidizing propenal with moist AgO or treating -hy-droxypropionitrile with sulphuric acid. Slowly converted to a resin at ordinary temperatures. Important glass-like resins are now manufactured from methyl acrylate, see acrylic resins. Propenoic acid itself can also be polymerized to important polymers - see acrylic acid polymers. 

The polymeric products can be made to vary widely in physical properties through controlled variation in the ratios of monomers employed in thek preparation, cross-linking, and control of molecular weight. They share common quaHties of high resistance to chemical and environmental attack, excellent clarity, and attractive strength properties (see Acrylic ester polymers). In addition to acryHc acid itself, methyl, ethyl, butyl, isobutyl, and 2-ethylhexyl acrylates are manufactured on a large scale and are available in better than 98—99% purity (4). They usually contain 10—200 ppm of hydroquinone monomethyl ether as polymerization inhibitor. 

If a waste sulfuric acid regeneration plant is not available, eg, as part of a joint acrylate—methacrylate manufacturing complex, the preferred catalyst for esterification is a sulfonic acid type ion-exchange resin. In this case the residue from the ester reactor bleed stripper can be disposed of by combustion to recover energy value as steam. 

Acrylic Acid. In Europe some acryHc acid [79-10-7] and ester is manufactured by the Reppe reaction from acetjdene, methanol, and carbon monoxide (eq. 10) (see Aacrylic acid and derivatives). 

The new propylene oxidation process uses less hazardous materials to manufacture acrylic acid, followed by esterification with the appropriate alcohol (Hochheiser, 1986) ... 

Manufacture of highly water-absorbent polymers with uniform particle size and good flowability can be carried out by reverse phase suspension polymerization of (meth)acrylic acid monomers in a hydrocarbon solvent containing crosslinker and radical initiator. Phosphoric acid monoester or diester of alka-nole or ethoxylated alkanole is used as surfactant. A polymer with water-absorbent capacity of 78 g/g polymer can be obtained [240]. 

Three major non-polymer propylene derivatives are isopropanol, acetone, and acrylic acid. Isopropanol (isopropyl alcohol) is used mainly as a solvent. It has been made from propylene by reaction with sulfuric acid and water for at least the last 75 years, making its manufacture the oldest, still-running commercial organic chemical process. It is used in household rubbing alcohol because, unlike ethanol, it is unfit for human consumption even in small amounts. About 25 % of the isopropanol produced is used for making acetone, in competition with a route based on isopropylbenzene. 

Applications As the basic process of electron transfer at an electrode is a fundamental electrochemical principle, polarography can widely be applied. Polarography can be used to determine electroreductible substances such as monomers, organic peroxides, accelerators and antioxidants in solvent extracts of polymers. Residual amounts of monomers remain in manufactured batches of (co)polymers. For food-packaging applications, it is necessary to ensure that the content of such monomers is below regulated level. Polarography has been used for a variety of monomers (styrene, a-methylstyrene, acrylic acid, acrylamide, acrylonitrile, methylmethacrylate) in... 

A depressant system developed for beneficiation of Ta/Nb-Zr ores involves oxalic acid-hydro fluoro silicic acid and depressant SHQ. SHQ is a mixture of a low-molecular-weight acrylic acid and condensation product of disulphonic acid (Suspendol PKK, manufactured by Cognis, Germany). After the development of the final reagent scheme, a series of locked-cycle tests were performed using the flowsheet shown in Figure 23.7. 

The propylene equivalent of polyethylene is polypropylene. About 50% of the chemical use of propylene is directed to that use. Other major applications are the manufacture of propylene oxide, isopropyl alcohol, cumene, 0X0 alcohols, acrylic acids, and acrylonitrile. The consumer products you are familiar with show up everywhere carpets, rope, clothing, plastics in automobiles, appliances, toys, rubbing alcohol, paints, and epoxy glue. 

Well, not quite. First, they sound similar because at one time, one of them, acrylonitrile, was based solely on manufacture from acrolein, a pungent liquid whose roots in Latin are aca- meaning sharp, and oiere, meaning smell. Acrylonitrile was made from acrolein, and acrylates were derivatives of acrylonitrile. But acrylates also are made from acrylic acid, which is also a derivative of acrylonitrile. So the name, acrylo, covers an extended farnily of relations. 

Uses. Intermediate in the manufacture of acrylic acid herbicide algicide in pharmaceuticals, perfumes, food supplements, and resins as a warning agent in methyl chloride refrigerating systems... 

Feng YS, Chen PC, Wen FS et al (2008) Nitrile hydratase from Mesorhizobium sp F28 and its potential for nitrile biotransformation. Process Biochem 43 1391-1397 Wang CC, Lee CM, Wu AS (2009) Acrylic acid removal from synthetic wastewater and industrial wastewater using Ralstonia solanacearum and Acidovorax avenae isolated from a wastewater treatment system manufactured with polyacrylonitrile fiber. Water Sci Technol 60 3011-3016... 

Hazards Associated with Organic Chemical Manufacturing Esterification Process for Acrylic Acid Esters Production, Mitre Corp., McLean, VA, Report No. MTR-79W00378-01, April 1980. 

The syntheses of carboxylic acids and esters are widely studied processes. Since the first examples of carboxylation in the presence of metal carbonyls were reported by Reppe, these reactions are sometimes referred to as the Reppe reactions. In his pioneering work125-127 stoichiometric or catalytic amounts of [Ni(CO)4] and ethylene or acetylene were reacted in the presence of water or alcohols to form saturated and unsaturated acids and esters. Commercial processes are practiced in the manufacture of propionic acid, acrylic acid and acrylates (see Section 7.2.4). 

Acrolein and Acrylic Acid. Acrolein and acrylic acid are manufactured by the direct catalytic air oxidation of propylene. In a related process called ammoxida-tion, heterogeneous oxidation of propylene by oxygen in the presence of ammonia yields acrylonitrile (see Section 9.5.3). Similar catalysts based mainly on metal oxides of Mo and Sb are used in all three transformations. A wide array of single-phase systems such as bismuth molybdate or uranyl antimonate and multicomponent catalysts, such as iron oxide-antimony oxide or bismuth oxide-molybdenum oxide with other metal ions (Ce, Co, Ni), may be employed.939 The first commercial process to produce acrolein through the oxidation of propylene, however, was developed by Shell applying cuprous oxide on Si-C catalyst in the presence of I2 promoter. 

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