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Chemicals from Olefin Hydrocarbons
Published in James G. Speight, Handbook of Petrochemical Processes, 2019
The main use of acrolein is to produce acrylic acid and its esters. Acrolein is also an intermediate in the synthesis of pharmaceuticals and herbicides. It may also be used to produce glycerol by reaction with isopropanol (discussed later in this chapter). 2-Hexanedial, which could be a precursor for adipic acid and hexamethylene-diamine, may be prepared from acrolein tail-to-tail dimerization of acrolein using ruthenium catalyst that produces trans-2-hexanedial. The trimer, trans-6-hydroxy-5-formyl-2,7-octadienal is coproduced. Acrolein, may also be a precursor for 1,3-propanediol. Hydrolysis of acrolein produces 3-hydroxypropionaldehyde which could be hydrogenated to 1,3-propanediol. The diol could also be produced from ethylene oxide (Chapter 7).
Organic Air Pollutants
Published in Stanley E. Manahan, Environmental Chemistry, 2022
Acetaldehyde is a widely produced organic chemical used in the manufacture of acetic acid, plastics, and raw materials. Acrolein is used as a raw material to make acrylic acid and as a biocide and is responsible for the odor produced by overheated cooking oil owing to the breakdown of glycerol in the oil. Approximately 1 billion kg of acetone are produced each year as a solvent and for applications in the rubber, leather, and plastics industries. Methylethyl ketone is employed as a low-boiling solvent for coatings and adhesives and for the synthesis of other chemicals.
Organic Air Pollutants
Published in Stanley Manahan, Environmental Chemistry, 2017
Acetaldehyde is a widely produced organic chemical used in the manufacture of acetic acid, plastics, and raw materials. Acrolein is used as a raw material to make acrylic acid and as a biocide and is responsible for the odor produced by overheated cooking oil owing to the breakdown of glycerol in the oil. Approximately 1 billion kg of acetone are produced each year as a solvent and for applications in the rubber, leather, and plastics industries. Methylethyl ketone is employed as a low-boiling solvent for coatings and adhesives and for the synthesis of other chemicals.
Different scenarios of glycerin conversion to combustible products and their effects on compression ignition engine as fuel additive: a review
Published in Engineering Applications of Computational Fluid Mechanics, 2021
Farid Haghighat Shoar, Bahman Najafi, Shahab S. Band, Kwok-Wing Chau, Amir Mosavi
Different studies on dehydrating glycerol to acrolein were performed (Table 5) (Dasari et al., 2005; Domínguez-Barroso et al., 2019; Freitas et al., 2018; Katryniok et al., 2009; Parveen et al., 2019; Simonetti et al., 2007; Wang et al., 2003). Acrolein is a chemical material and is used as an industrial and pesticide chemical. So dealing with it requires safety tips (Auerbach et al., 2008). The conversion process of glycerol dehydration to acrolein is accompanied by adverse reactions and leading to the establishment of byproducts. This causes the formation of coke on the catalyst and changes its color from white to black. Besides, the catalyst increases weight and becomes inactive, and its efficiency and selectivity for acrolein production are reduced. 90% of glycerol conversion, with 80% selectivity of acrolein, is achievable in supercritical conditions at 34.5 MPa, 673 K and in the vicinity of H2SO4 catalyst. In order to improve the efficiency of this process, the authors propose to increase the concentration of glycerol and H2SO4 and work at higher pressures (Watanabe et al., 2007). After the acrolein product, the product of 3-hydroxy propion aldehyde (3-HPA) is another glycerine-derived substance during the dehydration procedure. 3-HPA is an important industrial intermediate that can be converted into a number of large-scale conventional chemicals. Figure 11 is adapted and reproduced from (Zheng et al., 2008). These include acrolein, acrylic acid, 3-hydroxy propionic acid (3- HPA), malonic acid, acrylamide and 1, 3-propanediol.
An overview of selected emerging outdoor airborne pollutants and air quality issues: The need to reduce uncertainty about environmental and human impacts
Published in Journal of the Air & Waste Management Association, 2020
Acrolein is a reactive chemical that has many sources and toxic effects (Cahill 2014). Acrolein may also arise from the breakdown or oxidation of certain pollutants (such as 1,3 butadiene) or from the burning of organic matter as well as produced by vehicle combustion (Cahill 2014). It belongs to the family of aldehydes and is known to react with ozone and OH. The atmospheric lifetime is estimated to be 12–17 h and is a precursor of formaldehyde and PAN (peroxyacyl nitrate) (Seinfeld and Pandis 2006). Stroud et al. (2016) found no changes in average concentrations in Canada from the period 2004–2010. However, a net annual increase of 86 to 110 tons of acrolein has been noted from 2009 to 2013 in Canada with a total of 102 tons in 2017 (ECCC 2019). The largest use of acrolein is as an intermediate in the synthesis of acrylic acid and as a biocide mostly related to wood products and pulp and paper industries (ECCC 2019). It is recognized as carcinogenic in animals (information is insufficient for humans) but inhalation in humans may produce irritation and congestion in the upper respiratory tract (ATSDR 2007; US/EPA 2003). Galarneau et al. (2016) have shown that this compound exceeded one or more provincial guidelines in Canada at least at one or more sites during the period 2009–2013 using NAPS data. In California, Cahill (2014) found that the median natural summertime background is near 40 ng/m3 which is double than EPA’s reference concentration of 20 ng/m3. Moreover, the same author measured concentrations in an urban environment to be 3–8 fold that of that background. In Canada, Galarneau et al. (2016) found that acrolein measurements are often close to the detection limit in NAPS measurements (their Figure 2). Although the difficulty of measurements as described in Cahill (2014) exists, Galarneau et al. (2016) recommend increasing the monitoring of this compound in Canada.
Sustainability of biodiesel production in Malaysia by production of bio-oil from crude glycerol using microwave pyrolysis: a review
Published in Green Chemistry Letters and Reviews, 2018
Saifuddin Nomanbhay, Refal Hussein, Mei Yin Ong
Looking at the glycerol market worldwide, there has been a rapid increase in glycerol supply since 2003. The prices of both refined and crude glycerol have been on the decline due to a surplus of glycerol from biodiesel. The market surplus of glycerol from biodiesel is far from being tackled by new demand as platform chemical. Recent market analysis projects that demand glycerin by-product of oleochemicals and biodiesel production will expand at an annualized average rate of 7% during 2007–2021, with 6 million tons of overall production in 2025 (161). There are several studies on the techno-economic analysis of biomass fast pyrolysis for bio-oil production available in the literature. These studies have reported that bio-oil costs can range from US$0.62/gal to US$1.40/gal and the capital costs ranging from US$7.8 to US$143 million over a 240 MT/day to 1000 MT/day plant capacity (162). In terms of usage of glycerol for production of bio-based products, the versatile chemical acrolein is one of the most important. Acrolein is one of the very useful intermediates in the chemical industry due to its wide utilization of acrylic acid, superabsorbent polymer, 1,3-propanediol, and many more polymers or polyesters’ production (163). An analysis of the cost of production of acrolein from bio-glycerol (both pure and crude) will give a better understanding of the implication of utilization of waste glycerol for value-added products to the biodiesel industry. Table 12 shows the several major components in the cost that differ greatly between propylene-based and bio-based methods for a 10,000-ton acrolein production. The quantities for steam only refer to what is used in the reaction. In addition, the energy listed in the table only refers to the part of the energy required to heat up the reactant(s) and required for the reaction (assuming the energy consumption of all the other processes are the same for both production methods). The quantities of the feedstocks required for both processes are calculated based on the stoichiometric relation under the assumption of 80 mol% acrolein yield, and the quantity calculated for crude glycerol was based on the glycerol purity of 80%.