Organic chemical

There are a wide range of organic compounds synthesized by man for various uses in modern society. The total number synthesized exceeds 

000 with an estimated 60,000 in common use and approximately 1,000 added per year (Maugh, 1978) it has been estimated, that approximately 

Sediment concentration data of major groups of organic contaminants -aliphatic and aromatic hydrocarbons, chlorinated pesticides, phenols, polychlorinated biphenyls and -dibenzodioxins - are summarized in Table 2-5 (the book by Moore Ramamoorthy contains information on physicochemical properties, production, uses and discharges, and on toxicity). 

Because of their volatility most aliphatics - e.g. chloromethane, chloroform, carbon tetrachloride, trichloroethylene, tetrachloroethylene -occur at low or nondetectable levels in sediments. 

Benzene, toluene, and some of their derivates are both moderately volatile and soluble in water. Consequently, large-scale sorption to sediments does not occur. Substitution by Cl or N in compounds such as dichlorobenzene, hexachlorobenzene, and dinitrotoluene affects relative high concentrations in sediments near specific industries (see 2.4). 

Originally the chemical industry was inorganic in the 1960s organic chemicals (means they contain carbon) came into prominence with the compounds benzene, phenol, ethylene, and vinyl chloride. The organic chemicals benzene, phenol, toluene, and the xylenes compose the aromatic group. 

CydoheKin Cume/i B4nur ChioiobcnEeni Dlphtriyl. Eutyiben n Nhr ti n2 n  

The simplest organic chemicals are the saturated hydrocarbons methane (CH4), I3 

Acetylene and ethylene compete as a chemical raw material. Ethylene is generally more economical, resulting in declining use of acetylene as a raw material. Calcium carbide, a raw material for acetylene has other uses. Treated with nitrogen, it gives calcium cyanamide, valuable as a fertilizer and weed killer, and a raw material for the production of melamine, used ir ng some modern plastics. 

Propylene is produced in less volume than acetylene or ethylene. It is a raw material for 

Certain waste treatments reduce multiple hazards in one step. For example, incineration can destroy oxidizable organic chemicals and infectious agents, waste feed rates can be controlled to meet emission limits for volatile radionuclides, and radioactive ash can be disposed of as a dry radioactive waste. Likewise, some chemical treatment methods (e.g., those using bleach) both oxidize toxic chemicals and disinfect biological hazards. Such treatment could convert a chemical-radioactive-biological waste to a radioactive waste. 

Regional EPA offices and state and local hazardous waste authorities differ in their regulation of storage 

Nevertheless, there is often merit for such in-lahoratory treatment. Below are some procedures of genaal use at the laboratory scale. Additional procedures can be found in the earher edition of this hook (Prudent Practices for Disposal of Chemicals from Laboratories NRC, 1983) and other books listed in the bibliography. More specific procedures for laboratory treatment are increasingly being included in the experimental sections of chemical journals and in publications such as Organic Syntheses and Inorganic Syntheses. 

Neutralization of acids and bases (corrosives) is generally exempt from a RCRA treatment permit. However, because the products of the reaction are often disposed of in the sanitary sewer, it is important to ensure that hazardous waste such as toxic metal ions is not a part of the effluent. 

In most laboratories, both waste acids and waste bases are generated, and so it is most economical to collect them separately and then neutralize one with the other. If additional acid or base is required, sulfuric or hydrochloric acid and sodium or magnesium hydroxide, respectively, can be used. 

The major end uses of chlorine are described in Table 1.1. Chlorine is used either directly or indirectly in the manufacture of organic and inorganic chemicals. The primary market is in the production of organic chemicals, described in Section 1.3.1. Section 1.3.2 discusses the inorganic chemicals. 

Direct use of chlorine is in pulp and paper manufacturing and water treatment operations. Chlorine is used in the pulp and paper industiy to bleach the pulp to produce a high-quality whitened material, devoid of dark lignin and any other undesirable residuals. Chlorine has been the most common disinfectant and is still used by municipalities and others to treat potable, process, and waste water streams. Because of this specific use of chlorine, waterborne diseases such as typhoid and cholera have been eradicated in the industrialized world. Chlorine also removes hydrogen sulfide, iron compounds, and organic species that are responsible for objectionable tastes or odor associated with water. 

Propylene oxide, made by reacting propylene with chlorine to form propylene chloro-hydrin which is then dehydrochlorinated with caustic soda or lime (Eqs. 3-5), is used in the production of polyether polyols used for producing urethane foam. It also finds use in propylene glycol for making unsaturated polyester resins and in the pharmaceutical and food industries. Epichlorohydrin (EPI), formed by chlorination of propylene to allyl chloride and then dehydrochlorination (Eqs. 6 and 7), is used to make epoxy resins for producing laminates, fiber-reinforced composites, protective coatings, and adhesives. 

TABLE 1.1. End Uses of CMorine (with permission from SRI Consulting) 

WriouB borne net eauBdng Thnt rtieate pharmaeeutieals 

Esters and aliphatic hydrocarbons do not affect the polyurethane to a great degree. 

Aromatic hydrocarbons need to be used with careful consideration. At ambient temperatures, they can cause swelling, and at higher temperatures there is a slow breakdown. It has been found that in uses up to 40 or 50°C, polyurethane can be used in petroleum pump valve seats. 

Petrol (with alcohol) D Alcohol makes it more aggressive 

Natural oils and fats have little to no effect on polyurethanes. Use of food grades will often be required. 

Ethyl 1 alcohol J Polyethyler Ethyl 1 chloride J Butadier Neopren Paints Adhesives Eibers Polypropylei Solvents Resins Drugs 

Solvents Plastics Ethylene J] glycol J] Gasoline Synthetic Synthetic Plastics J Detergents 

Pharmaceuticals additive J rubber J rubber J Hydraulic fluids 

FIGURE 14.1 Hydrocarbons from petroleum and natural gas as raw materials. Catalytic cracking produces ethylene, butylene, acetylene, and propylene, which are converted Into other chemical raw materials and many kinds of consumer products. 

Heating coal at high temperatures in the absence of air produces a mixture of coke, coal tar, and coal gas. The process, called pyrolysis, is represented by 

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Ethyne is the starting point for the manufacture of a wide range of chemicals, amongst which the most important are acrylonitrile, vinyl chloride, vinyl acetate, ethanal, ethanoic acid, tri- and perchloro-ethylene, neoprene and polyvinyl alcohol. Processes such as vinylation, ethinylation, carbonylation, oligomerization and Reppe processes offer the possibility of producing various organic chemicals cheaply. Used in oxy-acetylene welding. 

Outside of carbon monoxide for which the toxicity is already well-known, five types of organic chemical compounds capable of being emitted by vehicles will be the focus of our particular attention these are benzene, 1-3 butadiene, formaldehyde, acetaldehyde and polynuclear aromatic hydrocarbons, PNA, taken as a whole. Among the latter, two, like benzo [a] pyrene, are viewed as carcinogens. Benzene is considered here not as a motor fuel component emitted by evaporation, but because of its presence in exhaust gas (see Figure 5.25). 

I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, New York, 1976. 

Figure 10.1-S. LCsq values for the fish species Pimephalas promelas versus log P of a highly diverse set of organic chemicals. Chemicals are marked by their mode of action.

For the production of this edition, we have made a thorough and critical revision of the whole contents of the book, based on our experience of its use in the laboratory and on the general advance in organic chemical practice. In addition to this general revision, however, we have extended the book in three main directions. 

After completing my studies and thesis, in June 1949 I was named to a faculty position as an assistant professor in Zemplen s organic chemical institute. The following month I married my boyhood love. 

The organic chemical structural types believed to be characteristic of coals include complex polycyclic aromatic ring systems with connecting bridges and varied oxygen-, sulfur-, and nitrogen-containing functionalities. 

Note that the stereochemistry comes out right. H s a and b are cis because they were cis in the starting quinone and the Diels-Alder reaction is stereospecific in this respect. H is also cis to and H " because the Diels-Alder reaction is stereoselectively endo. These points are described in more detail in Norman p.284-6 and explained in Ian Fleming Frontier Orbitals and Organic Chemical Reactions, Wiley 1976, p. 106-109. How would you make diene A ... 

PROPENE The major use of propene is in the produc tion of polypropylene Two other propene derived organic chemicals acrylonitrile and propylene oxide are also starting materials for polymer synthesis Acrylonitrile is used to make acrylic fibers (see Table 6 5) and propylene oxide is one component in the preparation of polyurethane polymers Cumene itself has no direct uses but rather serves as the starting material in a process that yields two valuable indus trial chemicals acetone and phenol... 

As the experimental tools for biochemical transformations have become more pow erful and procedures for carrying out these transformations m the laboratory more rou tine the application of biochemical processes to mainstream organic chemical tasks including the production of enantiomerically pure chiral molecules has grown... 

Toluene is also an important organic chemical Like benzene its early industrial production was from coal tar but most of it now comes from petroleum... 

Ziegler found that adding certain metals or their compounds to the reaction mixture led to the formation of ethylene oligomers with 6-18 carbons but others promoted the for matron of very long carbon chains giving polyethylene Both were major discoveries The 6-18 carbon ethylene oligomers constitute a class of industrial organic chemicals known as linear a olefins that are produced at a rate of 3 X 10 pounds/year m the... 

Section 14 15 Coordination polymerization of ethylene and propene has the biggest eco nomic impact of any organic chemical process Ziegler-Natta polymer ization IS carried out using catalysts derived from transition metals such as titanium and zirconium tt Bonded and ct bonded organometallic com pounds are intermediates m coordination polymerization... 

The chemistry of the carbonyl group is probably the single most important aspect of organic chemical reactivity Classes of compounds that contain the carbonyl group include many derived from carboxylic acids (acyl chlorides acid anhydrides esters and amides) as well as the two related classes discussed m this chapter aldehydes and ketones... 

Essential is also used as the adjective form of the noun essence The mixtures of substances that make up the fragrant material of plants are called essential oils because they contain the essence that is the odor of the plant The study of the composition of essential oils ranks as one of the oldest areas of organic chemical research Very often the principal volatile component of an essential oil belongs to a class of chemical sub stances called the terpenes... 

Ether (Section 16 1) Molecule that contains a C—O—C unit such as ROR ROAr orArOAr Ethylene (Section 5 1) H2C=CH2 the simplest alkene and the most important industnal organic chemical Ethyl group (Section 2 13) The group CH3CH2—... 

Ethylene and Propene The Most Important Industrial Organic Chemicals... 

Biemann, K., Mass Spectrometry Organic Chemical Applications, McGraw-Hill, New York, 1962. 

Metal organic chemical vapor deposition pOCVD)... 

L. Y. Young and C. E. CemigUa, eds.. Microbial Transformation and Degradation of Toxic Organic Chemicals, WUey-Liss, New York, 1995. 

Formaldehyde, HCHO, is a primary and necessary constituent of the first five synthetic adhesives in the listing. It is a simple organic chemical first identified during the latter half of the 1800s. Its irritating and toxic odor and preservative properties were known from the time of its early development. It is a ubiquitous chemical, formed naturally in small quantities by every process of incomplete combustion as well as in normal biologic processes. The human body has a natural formaldehyde level of about 3 lg/g, ie, 3 parts per million (ppm) in the blood at all times. 

Although acetyl chloride is a convenient reagent for deterrnination of hydroxyl groups, spectroscopic methods have largely replaced this appHcation in organic chemical analysis. Acetyl chloride does form derivatives of phenols, uncompHcated by the presence of strong acid catalysts, however, and it finds some use in acetylating primary and secondary amines. 

Synthetic Organic Chemicals, U.S. Production and Sales, 1970—1986, U.S. International Trade Commission, Washington, D.C. 

Synthetic Organic Chemicals, United States Production and Sales, USITC PubHcation, 1989. 

Adipic acid is a very large volume organic chemical. Worldwide production in 1986 reached 1.6 x 10 t (3.5 x 10 lb) (158) and in 1989 was estimated at more than 1.9 x 10 t (Table 7). It is one of the top fifty (159) chemicals produced in the United States in terms of volume, with 1989 production estimated at 745,000 t (160). Growth rate in demand in the United States for the period 1988—1993 is estimated at 2.5% per year based on 1987—1989 (160). Table 7 provides individual capacities for U.S. manufacturers. Western European capacity is essentially equivalent to that in the United States at 800,000 t/yr. Demand is highly cycHc (161), reflecting the automotive and housing markets especially. Prices usually foUow the variabiUty in cmde oil prices. Adipic acid for nylon takes about 60% of U.S. cyclohexane production the remainder goes to caprolactam for nylon-6, export, and miscellaneous uses (162). In 1989 about 88% of U.S. adipic acid production was used in nylon-6,6 (77% fiber and 11% resin), 3% in polyurethanes, 2.5% in plasticizers, 2.7% miscellaneous, and 4.5% exported (160). 

Metal organic decomposition (MOD) is a synthesis technique in which metal-containing organic chemicals react with water in a nonaqueous solvent to produce a metal hydroxide or hydrous oxide, or in special cases, an anhydrous metal oxide (7). MOD techniques can also be used to prepare nonoxide powders (8,9). Powders may require calcination to obtain the desired phase. A major advantage of the MOD method is the control over purity and stoichiometry that can be achieved. Two limitations are atmosphere control (if required) and expense of the chemicals. However, the cost of metal organic chemicals is decreasing with greater use of MOD techniques. 

Synthetic Organic Chemicals Pubhcation 776, U.S. International Trade Commission. 

Methanol (qv) is one of the 10 largest volume organic chemicals produced in the wodd, with over 18 x 10 t of production in 1990. The reactions for the synthesis of methanol from CO, CO2, and H2 are shown below. The water gas shift reaction also is important in methanol synthesis. 

Calcium carbide has been used in steel production to lower sulfur emissions when coke with high sulfur content is used. The principal use of carbide remains hydrolysis for acetylene (C2H2) production. Acetylene is widely used as a welding gas, and is also a versatile intermediate for the synthesis of many organic chemicals. Approximately 450,000 t of acetylene were used aimuaHy in the early 1960s for the production of such chemicals as acrylonitrile, acrylates, chlorinated solvents, chloroprene, vinyl acetate, and vinyl chloride. Since then, petroleum-derived olefins have replaced acetylene in these uses. 

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