Synthetic alcohol manufacture

Survey and natural alcohols manufacture, Synthetic processes,... 

Absolute methyl alcohol. The synthetic methanol now available is suitable for most purposes without purification indeed, some manufacturers claim a purity of 99 85 per cent, with not more than 0 1 per cent, by weight of water and not more than 0 02 per cent, by weight of acetone. Frequently, however, the acetone content may be as high as 0 1 per cent, and the water content 0-5-1 per cent. 

The normal paraffins produced are raw materials for the manufacture of biodegradable detergents, plasticizers, alcohols, and synthetic proteins. Removal of the / -paraffins upgrades gasoline by improving the octane rating. 

Primary alcohols are produced either by the catalytic hydrogenation of methyl esters or by fatty acids derived from oils and fats, e.g., coconut oil (C12-C14) or tallow (Cl6-C18), or from synthetic sources. Alcohols manufactured from natural oils and fats and from the Ziegler-type processes produce even-numbered chain length primary alcohols. 

ALCOHOLS,HIGHERALIPHATIC - SYNTHETIC PROCESSES] (Vol 1) -m malonate manufacture [MALONIC ACID AND DERIVATIVES] (Vol 15)... 

Coconut oil and tallow were the principal raw material sources for early fatty alcohol manufacture. Coconut oil is a lauryl-range oil and affords primarily C 12 and C 1 < alcohols. Tallow is a stearyl-range oil and yields primarily C1 and C is alcohols. Both of these natural products form only even carbon-numbered alcohols. Some synthetic alcohols contain both even and odd carbon-numbered alcohols while other synthetic alcohols are like the natural products and contain only even carbon-numbered homologs. 

Synthetic fatty alcohols fall into three broad categories and are manufactured from two basic raw materials—ethylene and n-paraffins. One group is secondary alcohols which are prepared by oxidation of n-paraffins in the presence of boric acid. A second group consists of oxo alcohols manufactured by hydroformylation of linear olefins which are derived from either n-paraffins or ethylene. Both of these alcohol types are discussed in separate chapters. The last group is Ziegler alcohols which are prepared from ethylene and are the primary subject of this chapter. 

Use Manufacture of isopropyl alcohol, polypropylene, synthetic glycerol, acrylonitrile, propylene oxide, heptene, cumene, polymer gasoline, acrylic acid, vinyl resins, oxo chemicals. 

Synthetic Acetic Acid.—During the war large quantities of acetic acid have been manufactured synthetically the process being the same as that described under synthetic alcohol in this x>lume, as far as the production of acetalde-hyde. This substance is converted into acetic acid by ox>-gen obtained by the fractional distillation of hquid air in the presence of a catalyst. According to the Drefus patents [e.g. French Patent, No. 479656/1916, and British Patent, No. 105064/1917), which have been operated in the production of acetaldehyde and acetic acid from acetylene, the gas is passed with water a) into solvents in wliicli mercury is soluble, e.g. sulphuric, phosphoric, and acetic acids or (i) into solvents in which acetylene is soluble, e.g. acetone. In the former case, one or more of the following conditions are observed —... 

CCRIS 1356 EINECS 204-062-1 HSDB 175 Methylethene Methylethylene NCI-C50077 Propane 1-Propene Propylene 1-Propylene R1270 UN1077. Chemical intermediate for manufacture of isopropyl alcohol, polypropylene, synthetic glycerol, acrylonitrile, propylene oxide, heptane, cumene, polymer gasoline, acrylic xid, vinyl resins, 0x0 chemicals. Gas mp = -186.2° bp = -47.5° d = 0.505 very soluble in H2O (23 g/100 ml), EtOH, AcOH. Air Prods Chems Amoco Lubricants BP Chem. Chevron Exxon Fina Chemicals Mobil OxyChem Phillips 66 Shell Texaco. 

NIR is used in both process control and quality assurance of synthetic alcohol manufacture. A calibration was developed on a precision scanning analyzer using a temperature-controlled liquid cell at 45°C. Samples ranged from 130-290 OH. The r was 0.9998, with an SEE of 0.8 OH and an F value of 14,000. 

The CPI industry manufactures alcohols, detergents, synthetic rubber, glycerin, fertilizers, sulfur, solvents, and feedstock for the manufacture of drugs, nylon, plastics, paints, polyesters, food additives and supplements, explosives, dyes, and insulating materials. The petrochemical industry uses about 5% of the total supply of oil and gas in the US. 

The other firm, which had their methanol on the market before Du Pont, was Commercial Solvents Corporation, with plants in Terre Haute, Indiana, and Peoria, Illinois. They manufactured synthetic methyl alcohol in 1927 in a high-pressure works originally designed to produce ammonia. Haynes, American Chemical Industry, 4 169-77, 6 86-87. With the French developers of an ammonia process, Du Pont... 

Uses. Furfural is primarily a chemical feedstock for a number of monomeric compounds and resins. One route produces furan by decarbonylation. Tetrahydrofuran is derived from furan by hydrogenation. Polytetramethylene ether glycol [25190-06-1] is manufactured from tetrahydrofuran by a ring opening polymeri2ation reaction. Another route (hydrogenation) produces furfuryl alcohol, tetrahydrofurfuryl alcohol, 2-methylfuran, and 2-methyltetrahydrofuran. A variety of proprietary synthetic resins are manufactured from furfural and/or furfuryl alcohol. Other... 

Uses. Furfuryl alcohol is widely used as a monomer in manufacturing furfuryl alcohol resins, and as a reactive solvent in a variety of synthetic resins and appHcations. Resins derived from furfuryl alcohol are the most important appHcation for furfuryl alcohol in both utihty and volume. The final cross-linked products display outstanding chemical, thermal, and mechanical properties. They are also heat-stable and remarkably resistant to acids, alkaUes, and solvents. Many commercial resins of various compositions and properties have been prepared by polymerization of furfuryl alcohol and other co-reactants such as furfural, formaldehyde, glyoxal, resorcinol, phenoHc compounds and urea. In 1992, domestic furfuryl alcohol consumption was estimated at 47 million pounds (38). 

Most higher alcohols of commercial importance are primary alcohols secondary alcohols have more limited specialty uses. Detergent range alcohols are apt to be straight chain materials and are made either from natural fats and oils or by petrochemical processes. The plasticizer range alcohols are more likely to be branched chain materials and are made primarily by petrochemical processes. Whereas alcohols made from natural fats and oils are always linear, some petrochemical processes produce linear alcohols and others do not. Industrial manufacturing processes are discussed in Synthetic processes. 

Methylene iodide [75-11-6], CH2I2, also known as diio dome thane, mol wt 267.87, 94.76% I, mp 6.0°C, and bp 181°C, is a very heavy colorless Hquid. It has a density of 3.325 g/mL at 20°C and a refractive index of 1.7538 at 4°C. It darkens in contact with air, moisture, and light. Its solubiHty in water is 1.42 g/100 g H2O at 20°C it is soluble in alcohol, chloroform, ben2ene, and ether. Methylene iodide is prepared by reaction of sodium arsenite and iodoform with sodium hydroxide reaction of iodine, sodium ethoxide, and hydroiodic acid on iodoform the oxidation of iodoacetic acid with potassium persulfate and by reaction of potassium iodide and methylene chloride (124,125). Diiodoform is used for determining the density and refractive index of minerals. It is also used as a starting material in the manufacture of x-ray contrast media and other synthetic pharmaceuticals (qv). 

Commodity Phthalate Esters. The family of phthalate esters are by far the most abundandy produced woddwide. Both orthophthaUc and terephthahc acid and anhydrides are manufactured. The plasticizer esters are produced from these materials by reaction with an appropriate alcohol (eq. 1) terephthalate esterification for plasticizers is performed more abundandy in the United States. Phthalate esters are manufactured from methanol (C ) up to Qyj alcohols, although phthalate use as PVC plasticizers is generally in the range to The lower molecular weight phthalates find use in nitrocellulose the higher phthalates as synthetic lubricants for the automotive industries. 

Pyrrohdinone (2-pyrrohdone, butyrolactam or 2-Pyrol) (27) was first reported in 1889 as a product of the dehydration of 4-aminobutanoic acid (49). The synthesis used for commercial manufacture, ie, condensation of butyrolactone with ammonia at high temperatures, was first described in 1936 (50). Other synthetic routes include carbon monoxide insertion into allylamine (51,52), hydrolytic hydrogenation of succinonitnle (53,54), and hydrogenation of ammoniacal solutions of maleic or succinic acids (55—57). Properties of 2-pyrrohdinone are Hsted in Table 2. 2-Pyrrohdinone is completely miscible with water, lower alcohols, lower ketones, ether, ethyl acetate, chloroform, and benzene. It is soluble to ca 1 wt % in aUphatic hydrocarbons. 

Synthesis and Manufacture of Amines. The chemical and busiaess segments of amines (qv) and quaternaries are so closely linked that it is difficult to consider these separately. The majority of commercially produced amines origiaate from three amine raw materials natural fats and oils, a-olefins, and fatty alcohols. Most large commercial manufacturers of quaternary ammonium compounds are fully back-iategrated to at least one of these three sources of amines. The amines are then used to produce a wide array of commercially available quaternary ammonium compounds. Some iadividual quaternary ammonium compounds can be produced by more than one synthetic route. 

---