Derived from Propylene

Acrylonitrile is obtained by reacting propylene with ammonia  

Another important monomer, methylmethacrylate (acrylic), is obtained by reacting propylene with carbon monoxide, oxygen and methanol  

Propylene also serves as the source of the epoxy polymer, via epichlorohydrin  

Incidentally, by a series of oxidation reactions on propylene, a very useful polyol (glycerol) can be derived. The latter serves mainly in polyfunctional thermosets such as alkyds that imdergo cross-linking. 

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Polyether Polyols. Polyether polyols are addition products derived from cyclic ethers (Table 4). The alkylene oxide polymerisation is usually initiated by alkah hydroxides, especially potassium hydroxide. In the base-catalysed polymerisation of propylene oxide, some rearrangement occurs to give aHyl alcohol. Further reaction of aHyl alcohol with propylene oxide produces a monofunctional alcohol. Therefore, polyether polyols derived from propylene oxide are not truly diftmctional. By using sine hexacyano cobaltate as catalyst, a more diftmctional polyol is obtained (20). Olin has introduced the diftmctional polyether polyols under the trade name POLY-L. Trichlorobutylene oxide-derived polyether polyols are useful as reactive fire retardants. Poly(tetramethylene glycol) (PTMG) is produced in the acid-catalysed homopolymerisation of tetrahydrofuran. Copolymers derived from tetrahydrofuran and ethylene oxide are also produced. 

Epichlorohydrin, the more expensive compound is derived from propylene by the sequence of reactions shown in Figure 26.2. 

Propene is used as a starting material for numerous other compounds. Chief among these are isopropyl alcohol, acrylonitrile, and propylene oxide. Isopropyl alcohol results from the hydration of propylene during cracking and is the primary chemical derived from propylene. Isopropyl alcohol is used as a solvent, antifreeze, and as rubbing alcohol, but its major use is for the production of acetone. Acrylonitrile is used primarily as a monomer in the production of acrylic fibers. Polymerized acrylonitrile fibers are produced under the trade names such as Orion (DuPont) and Acrilan (Monsanto). Acrylonitrile is also a reactant in the synthesis of dyes, pharmaceuticals, synthetic rubber, and resins. Acrylonitrile production occurs primarily through ammoxidation of propylene CH3- CH = CH2 + NH3 + 1.5 02—> CH2 = CH - C = N + 3 H20. 

Polyalkylene Oxide Block Copolymers. The higher alkylene oxides derived from propylene, butylene, styrene (qv), and cydohexene react with active oxygens in a manner analogous to the reaction of ethylene oxide. Because the hydrophilic oxygen constitutes a smaller proportion of these molecules, the net effect is that the oxides, unlike ethylene oxide, are hydrophobic. The higher oxides are not used commercially as surfactant raw materials except for minor quantities that are employed as chain terminators in polyoxyethylene surfactants to lower the foaming tendency. The hydrophobic nature of propylene oxide units, —CH(CH3)CH20—, has been utilized in several ways in the manufacture of surfactants. Manufacture, properties, and uses of poly(oxyetbylene-fro-oxypropylene) have been reviewed (98). 

Glycerol. Another synthetic product that is derived from propylene for the production of resins is glycerol. Synthetic production of this material, which started in 1948 at the Houston, Tex., plant of Shell Development Co., culminated a long research program by E. C. Williams and coworkers (45) in which the process was developed through a complex series of reactions starting with the chlorination of propylene (7). The Houston plant has a reported capacity of 36,000,000 pounds per year, which is equivalent to 20% of the prewar production of glycerol (8). 

Acetic Anhydride. Other products recovered from the oxidation of light hydrocarbons (6) are acetic acid and acetic anhydride as well as acetaldehyde, acetone, and isopropyl alcohol, all of which may be converted to acetic acid or the anhydride. The direct oxidation process supplements the production of acetic anhydride from acetone derived from propylene, which has been the principal commercial source of the anhydride. The increasing production of cellulose acetate within recent years has been attributed to the low cost of acetic anhydride from the latter process (44). 

Substances related to the glycerides are the propylene glycol esters, chemically derived from propylene glycol and fatty acids. Important examples are propylene glycol monocaprylate... 

CAS 9009-54-5. A thermoplastic polymer (which can be made thermosetting) produced by the condensation reaction of apolyisocyanate and a hydroxyl-containing material, e.g., a polyol derived from propylene oxide or trichlorobutylene oxide. The basic polymer unit is formed as follows I NCO + R2OH RjNHCOOR,. 

As an example, a group of polyether diols (block PO-EO copolymers with terminal poly[EO] block) are the polyethers derived from propylene glycol (or DPG), PO and EO of MW of 2000 daltons and around 15-20% EO as a terminal block (Figure 4.29). 

An alternative route to generate 1,4-butanediol is via the hydroformylation of allyl alcohol. This method was commercialized by LyondellBasell Industries and Dairen Chemical Corporation. Allyl alcohol is produced to isomerize propylene oxide derived from propylene over a lithium phosphate catalyst. Hydroformylation is performed to form 4-hydroxybutyraldehyde (Eq. (10.6)) followed by hydrogenation using Raney Ni catalyst to form 1,4-butanediol (Eq. (10.7)). The patent of Dairen Chemical showed 93% allyl alcohol conversion and 67% 1,4-butanediol selectivity and 31% 2-methyl-propanediol selectivity [7aj. 

Phenol and its O-alkyl derivatives (from propylene dimers, trimers, or tetra-mers) are oxyalkylated usually at atmospheric pressure or under moderate pressure conditions using basic catalysts at approximately 50°-200°C in the absence of solvents. Glass reaction flasks are the typical labware, thus the... 

Isoprene l-s3-ipren [prob. fr. is- - - propyl -f -ene] (1860) (3-methyl-1,3-butadiene, 2-methyl-1,3-butadiene) n. CH2=C-(CH3) CH=CH2- a colorless, volatile liquid derived from propylene or from coal gases or tars, chemically similar to the mer unit of natural rubber. Its polymer of the cis-1, 4-type of polyisoprene is chemistry s nearest approach to synthesizing the natural product and it has sometimes been called synthetic natural rubber . It has a molecular weight of 68.06, a mp of—120°C, and a bp of 34°C. Ash M, Ash I (1982-1983) Encyclopedia of plastics polymers, and resins, vols 1-3. Chemical Publishing Co., New York. 

Polyoxypropylene glycol n. Any low-molecular-weight polymer with the structure H[-0CH(CH3)CH2-] 0H, derived from propylene oxide and used in the production of polyurethane foams. 

As seen in Table 15.1, the most important EO/PO block nonionic surfactants are those derived from propylene glycol and ethylenediamine as initiators, commercially known as Pluronics and Tetronics. Their general formulae can be written as follows ... 

The group had constructed a molecular still and chose the polyester derived from propylene glycol and hexadecamethylene dicarboxylic acid for the first experiment. A waxy polyester was prepared and heated in the molecular still for an extended period. Tbe product was now tough with a chain length of about forty repeating units. Filaments of the ester could easily be drawn "taffy-like" from the melted product. When stress was applied to the solidified filaments, the thin opaque cylinder of filament separated into two sections joined by a thinner section of transparent fiber. As pulling continued, the transparent section grew till the opaque sections disappeared. 

The Polypropylene (PP) is one of the most versatile polymers available with a wide variety of packaging apphcations. The PP can be produced either as a homopolymer or as a copolymer. A homopolymer molecule is derived from a single monomer, which in the case of PP is derived from propylene. Alternatively, a copolymer molecule is derived from two or more monomers, which in the case of PP is derived from a combination of propylene and ethylene. Homopolymers are more crystalline than copolymers and have the highest strength and rigidity. Copolymers are classified into block and random variants. The properties and applications of PP are given in Table 1. 

Polypropylene Is derived from propylene, which was just discussed. The phenolic resin curative (methylol terminated, para-alkyl substituted, phenol-formaldehyde... 

Figure 9.6 2-Ethylhexanol derived from propylene (Process 1) or acetaldehyde (Process 2)...

As previously discussed, 2-Ethylhexanol is derived from propylene, acetaldehyde, or butyraldehyde see Figure 9.11. 

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