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Outline of Industrial Organic Chemistry, 3rd Edition



 
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ISBN-13/EAN: 9780820601694
ISBN: 0820601691
Author: Alfred Rieche, K. Littlewood
Chemical Publishing
Book - Hardback
Pub Date: Nov 28, 1970
600 pages
Features

Contents -

Introduction -
General remarks on technology -
Economy -
Development of a technological process -
Schematic and equipment flow diagram -

A. The chemistry of coal and crude on and the production of chemical raw materials and intermediates -

I. Technology and upgrading of coal -
Formation, mining, and properties of coal -
Mining of bituminous coal -
Mining of brown coal -
Economic aspects -
Mechanical preparation of bituminous coal -
Stream classification, flotation -
Mechanical preparation of brown coal  -
Drying of coal -
Types of driers -
Multiple-tube driers -
Drum driers -
Pulverizing-drying mill
Briquetting -
Coal as a fuel -
Types of furnaces -
Steam boilers -

(1) Carbonization of coal -
Coal gas, town gas -
Retorts and ovens -
Purification of gas -
Scrubbing and purification of gases -
Electrical dust collection -
Coking, low temperature carbonization -
Chemical processing of bituminous coal -
Low temperature carbonization -
High temperature carbonization -
Constituents of bituminous coal tar and their extraction -
Processing of tar -
Carbonization of brown coal, low temperature carbonization -
Circulating gas low temperature carbonization -
Extraction of the low temperature carbonization products -
Purification of effluents -
Phenosolvan method, biological purification -
The countercurrent and concurrent principle -
Batch and continuous methods of operation -
Extraction of liquids (extraction in liquid systems) -
MineraI wax (ozocerite), montan wax, extraction of coal -

(2) Gasification of coal -
Gasification of coal and coke -
Water gas, mixed gas, synthesis gas -
Gasification with oxygen -
Pressure gasification -
Conversion of water gas -
Purification of the gases for hydrogenation -
Wet purification process -
Removal of the carbon monoxide -

II. Natural gas and petroleum -
Natural gas -
Composition -
Underground gas storage -
Petroleum -
Occurrence and properties -
Origin -
Reserves -
World production of petroleum -
Prospecting -
Drilling techniques -
Extraction -

(1) Composition, upgrading, purification -
Distillation and rectification -
Continuous and batch distillation -
Columns -
Steam traps (condensate run-off) -
Condensers -
Determination of the theoretical number of plates -
(a) Distillation of petroleum, conversion and refining methods -
General remarks -
Distillation of petroleum -
(b) Refining and upgrading, dewaxing -
Deasphalting -
Purification of oils by selective extraction -
Extraction of aromatics from petroleum -
Desulphurization -
(c) Technical properties of motor fuels -
Anti-knock properties -

(2) The cracking processes -
Thermal cracking -
Catalytic cracking ('catcracking') -
Principles of catalytic cracking -
Fluidized bed processes -
Fluidized operations -

(3) Reforming -  
formation of aromatics -  
polymerization and alkylation -

Ill. Hydrogenation of coal, tar, and crude oil -
Chemistry -
History -

(1) Hydrogenation in the semi-solid phase -
High pressure seals -
Measurement of temperature -
Measurement of quantities -
Measurement of pressure -
Automatic control of chemical processes -
Feed pumps -
Shut-off and flow regulating devices -
High pressure valves -
Circulation gas heating -

(2) Hydrogenation in the gas phase -
Processing of the hydrogenation gases -

(3) Variations of the hydrogenation processes -
(a) Low temperature hydrogenation (LTH process) -
Refining by hydrogenation -
(b) High temperature processes -
Aromatization -
Dehydrogenation -
Pressure -
Hâ‚‚-dehydrogenation method (DHD method) -

IV. Syntheses with carbon monoxide -

(1) Hydrogenation of carbon monoxide -
(a) Hydrocarbon synthesis by the Fischer-Tropsch process -
Chemistry of the CO hydrogenation -
Technology of the synthesis processes -
Catalysts -
Final purification of the gas -
Catalyst ovens for synthesis at atmospheric pressure -
Operation -
Medium pressure synthesis -
Recent variations of the Fischer-Tropsch synthesis -
Ruhrchemie-Lurgi-High pressure synthesis -
Kellog suspended particle process -  
liquid-phase synthesis -  
variations of the method -  
prospects -
(b) Methanol and isobutyl oil synthesis -
Catalyst -
Starting gas -
Method of operation -
Isobutyl oil synthesis -
Use of the products -
Formaldehyde -
Dehydrogenation, partial oxidation -

(2) Various syntheses with carbon monoxide -
Formic acid -
oxalic acid -  
higher carboxylic acids -

V. Production and processing of simple paraffins and olefins -
Sources and production -
Industrial processes for the concentration and production of hydrocarbons in pure form -
Fractionation of coke oven gas into its components -
Separation of natural, hydrogenation and cracking gases -
Separation of paraffins and olefins -

(1) Technical processing of methane -
(a) Synthesis gas from methane -
(b) Chlorination of methane -
General remarks on chlorination of aliphatics -
Chlorination of methane -
Chemical use of methyl chloride -
Carbon tetrachloride, carbon disulphide -
(c) Hydrocarbons containing fluorine -
(d) Hydrocyanic acid from methane (Andrussov process) -
(e) Carbon black from methane and other hydrocarbons -

(2) Technical processing of ethylene -
Production methods -
Production of ethylene by dehydrogenation, cracking and pyrolysis processes -
General remarks on dehydrogenation and cracking -
Dehydrogenation of ethane -
Ethylene produced by cracking of gases -
Pyrolysis of liquid hydrocarbons -
(a) Halogen derivatives of ethylene -
(b) Ethylene oxide -
Production by the chlorhydrin process -
The direct oxidation method -
(c) Syntheses with ethylene oxide -
Glycols -
glycol ether -  
acrylic nitrile -  
acrylic ester -  
polyethylene oxide derivatives -
ethanolamines -
(d) Hydration of olefins to alcohols -
Indirect hydration -
Direct hydration -

(3) Propane and propylene -
(a) Propanol and di-isopropyl ether -
(b) Production of phenol using cumene -
(c) Glycerine -

Epichlorhydrin, allyl chloride, allyl alcohol -
(d) Direct syntheses of allyl alcohol and glycerine from propene -
(4) Butane and butene -
Transformation into butadiene -
(5) Higher molecular weight olefins -
(6) Chlorination of higher paraffins -
(7) Oxidation of paraffins -
(8)  Nitroparaffins -
 
VI. Industrial processes for the production o/various aliphatic compounds -  
(1) Dimethyl ether -
(2) Diethyl ether and di-isopropyl ether -
(3) Glycerine -
(4) Synthetic substitutes for glycerine -
(5) Aliphatic amines -

Retrospect and prospect of the technology of aliphatic compounds -

VII. Acetylene production and syntheses based on acetylene -  
(I) Production of acetylene -
 (a) Carbide and acetylene from carbide -
Oxy-thermal carbide process -
Acetylene from carbide -
Properties of acetylene -
(b) Production of acetylene by the electric arc process  -
(c) Acetylene produced by incomplete combustion of hydrocarbons -
(d) Acetylene produced by pyrolysis -
Hoechster pyrolysis process -
Eastman process -
The principle of the regenerative furnace (Wulff process) -
Prospect -

(2) Syntheses with acetylene -
General rules for working with  acetylene -
(a) Additions to acetylene -
Acetaldehyde -
Acetic acid -
Acetic anhydride -
Ketenes -
Esters of acetic acid -  
azeotropic esterification -
Chloroacetic acid -
(b) Vinylations -
Vinyl acetate -
Vinyl chloride -
Vinyl ether -
Acrylic nitrile -
(c) Ethinylation -
Propargylalcohol-
Butindiole -
(d) The butadiene process -
Reppe process -
Lebedev process -
Nieuwland process -
Butadiene from butane and butene -
The two-stage process of butane dehydrogenation -
The Homlry single-stage process -
Isoprene -
Butadiene from acetaldehyde -  
'four-stage process' -
Aldol condensation -
1,3 butylene glycol -
n-butanol from aldol -
(e) Dimerization of acetylene -
Chlorobutadiene -
(f) Acetone -

VIII. Aromatic intermediates -

General remarks on aromatic intermediates -

(I) The main operations in the production of intermediates and the equipment used -
(a) Equipment used in intermediate chemistry, problems concerning materials -
Sealing materials -
Stirring vessel and stirrer -
Autoclaves -
Means of heat transfer and heat dissipation -
Heating baths and heating liquids -
Coolants -
Filtration -
Suction filter -
Filter presses -
Special filters -
Rotary filters -
Centrifuges -
Drying -
Roller driers -
(b) Basic operations of intermediates chemistry -
General remarks -
Halogenation -
Nitration -
Sulphonation -
Problems of waste water -
Reductions -
Alkali melts -  
phenols -
Carboxylation -
Sublimation -
Amidation -
Exchange of halogens -
Exchange of sulphonic acid groups -
Exchange of OH groups -  
Bucherer reaction -
Mechanism of the Bucherer reaction -

(2) Diagrams of the processes for the production of important aromatic intermediates -
(a) Benzene derivatives -
Chlorinated benzenes and their secondary products -
Nitration of chlorobenzene -
Nitration of benzene and its secondary products -
Sulphonation of benzene -
Phenols -
(b) Derivatives of toluene -
(c) Derivatives of naphthalene -
Nitration of naphthalene and its secondary products -
Monosulphonation of naphthalene and its secondary products -
Disulphonation of naphthalene -
Phthalic anhydride -
(d) Anthracene derivatives -
Anthraquinone -  
anthraquinone derivatives -

B. The chemical processing of raw materials produced in agriculture and forestry -

I. Wood as a chemical raw material -

Chemical composition of wood -
Lignin -

(1) Chemical processing of wood -
(a) Wood distillation, wood carbonization -
(b) Wood saccharification -
Bergius-Rheinau process (Bergius-Hiigglund) -
Method of operation of an extraction or diffusion battery working on the counterflow principle -
Scholler wood hydrolysis process -
(c) Mechanical wood pulp and paper -
(d) Cellulose and processes for the pulping of wood -
Bleeching of wood pulp -
Sulphate digestion -  
alkali pulp -
Sulphite digestion -
sulphite pulp -
Reduction in the digestor -
Nitric acid digestion -  
N-cellulose -
Straw pulp and other pulps -

(2) Biological processing of wood sugar solutions and sulphite waste liquor -
General remarks -
(a) Alcohol from wood sugar -
(b) Alcohol from sulphite waste liquor, sulphite alcohol -
(c) Biological protein and fat synthesis (yeastification) -
General remarks on biological protein production -
Yeastification of wood sugar wort -
Yeastification of cellulose waste liquor -
The Waldhof cellulose process -
Atomizing drier -
IG-Scholler process -
Yeastification of alcohol residual liquor -
The Biosyn process -
Biological fat synthesis -
(d) Butanol-acetone fermentation of sulphite waste liquor -

(3) Industrial use of lignin -
Vanillin from sulphite waste liquor -
Lignin used in the production of plastics -

(4) Native bark extracts used as tannins -

(5) Oil of turpentine and rosin -

II. Sugar, starch and glucose -

(1) Manufacture of cane and beet sugar -
Manufacture of beet sugar -
Extraction -
Concentration by evaporation -
General remarks on heat transfer -
Types of evaporators -
Second separation of the syrup -
Purification and refining of sugar -
Sugar from sugar cane -

(2) Manufacture of starch -
Manufacture of starch from potatoes -
Dehydrated potatoes -
Starch from wheat -
Starch from rice -
Starch from maize -
Hydrolytic decomposition of starch -

(3) Starch sugar -

(4) Pectic substances  -

III. The fermentation industry -
 
General remarks on fermentation -  
Chemical basis -

(1) The brewing of beer -
Malting -
Production of the wort -
Fermentation -

(2) The manufacture of alcohol -
General remarks -
Denaturing -
a) Potato distillation -
Malting -
Steaming of potatoes -
Mashing and yeast production -
Delbruck's method of preliminary augmentation of yeast to mash -
Large-scale start -
Fermentation -
Distillation -
(b) Distillation of molasses -

IV. Technology of fats, oils, fatty acids and sopas -

(1) General notes on fats -
(a) Formation of fat -
(b) Digestion of fat -
(c) Chemical composition and properties of fats -
(d) Lipoids -
Waxes -
Phosphatides -

(2) Production of fats -
World production -

(a) Production of vegetable oils -
Pressing -
Extraction -
(b) Production of animal fats -
Land animals -  
sea animals -  
bone fat -

(3) Hardening of fats, hydrogenation -

(4) Manufacture of margarine -

(5) Manufacture of synthetic fats -
Chemosynthesis -
Biosynthesis -

(6) Fat alcohol-

(7) Lipolysis, manufacture of fatty acids and glycerine -
(a) Autoclave decomposition -
(b) Fermentation lipolysis with Iipases -
(c) Acidification -
(d) Twitchell decomposition -
Purification of fatty acids by distillation -

(8) Saponification with alkali, soaps -
Various types of soap -

(9) Manufacture and purification of glycerine -

V. Tanning and the manufacture of leather, Tannins -

General remarks -
Animal skins as raw materials -
Stages in the manufacture of leather -

(1) Tannery wet-work in the beamhouse -

(2) Tanning -
(a) Polyaromatic tanning -
Tanning with vegetable and aromatic synthetic tannins -
Tannins -
Syntans -
(b) Mineral tanning -
(c) Other tanning methods -
(d) Chemistry of tanning -

(3) Dressing  of leather -

(4) Main development problems in tanning -

C. The manufacture of commodities by chemical processing of natural and synthetic raw materials -

I. Synthetic fibres  -

History of their development -
Their basic constitution -
Methods of formation, spinning methods -
Table of the most important synthetic fibres -
Physical properties -
Stretching -
Bonds, orientation, and fibre strength -
Characteristics of yarns -

(1) Manufacture of semi-synthetic fibres -
(a) Cellulose fibres -
Cuprammonium rayon -
Viscose rayon -
Acetate rayon -
Production of Cellit K -
Preparation of the spinning solution -
(b) Protein fibres -

(2) Fully synthetic fibres -
(a) Polymerizates as fibres -
PC fibre -
Polyacrylonitrile fibre -
(b) Polycondensates as fibres -
Polyamides -
Polyurethane -
Polyester, Terylene, Lanon -
Prospects -

II. Raw materials for lacquers, plastics, elastomers, exchange resins, silicones -

General remarks on the chemistry of macromolecular substances, their formation and
their properties -
Polymerization -
Radical and ion polymerization -
The effect of inhibitors -
Cross-linking -
Isotactic polymers -
Steric configuration -
High polymers produced by condensation -
Mixed polymerizates and mixed condensates -
Polymerization techniques -
Physical properties, mechanical behaviour, and testing of plastics -
Testing methods -
Solubility, swelling, plasticizing -
Solvents for plastics -
Plasticizers -
Phosphoric acid ester -
Phthalic acid ester -
Other plasticizers
The most important plastics (synthetic substances and lacquer raw materials) -

(1) Lacquer raw materials and synthetics from natural products -
(a) Natural lacquer resins -
(b) Drying oils -
Chemistry of oil drying -
Oil cloth, linoleum -
(c) Semi-synthetic lacquer raw materials -
Alkyd resins, albertoles, cellulose derivatives -
(d) Synthetic materials made from natural products -
Artificial hom, vulcanized fibre, celluloid -
Technical methods of processing synthetic materials -
Films and foils -
Processing of thermoplastics -
Hardenable resins -
Comminution, grinding, mixing -

(2) Fully synthetic plastics -
(a) Thermoplastics (vinyl polymerizates) -
Polyethylene -
Polystyrene -
Polyvinylchloride -
Polytrifiuorochloroethylene and polytetrafiuoroethylene -
Polyvinyl acetate, polyvinyl alcohol and polyvinyl acetals -
Polyacrylic esters -
Other polymerizates -
(b) Linear, not hardenable polycondensates -
Polyamides, polyesters -
(c) Hardenable polycondensates -
PhenoIformaldehyde resins -
Urea-formaldehyde condensate -
Polycondensates produced by polyaddition or polymerization -
Polyisocyanates, epoxy resins, polyester resins -

(3) Elastomers -
Synthetic rubber, Buna, silicone rubber -

(4) Ion-exchange resins -
Prospects -

(5) Silicones -

lII. Textile auxiliaries and washing raw materials -

Classification -
Classes of compounds -
(a) Capillary-active materials -
General remarks -
Orientation of capillary-active substances and detergent effect -
Principle of the washing process -
Properties of detergents and textile auxiliaries and their testing in practice -
Washing capacity -
Specific effects of textile auxiliaries -
Production of capillary-active materials -
Chart of detergent and textile auxiliaries -
Paraffin oxidation -
Various textile auxiliaries and detergents -
Fatty acid derivatives -
Fatty alcohol sulphates -
Sulphochlorination of saturated hydrocarbons, Mersol, Mersolate -
Sulphoxidation -
Aralkylsulphonates -
Hydroxyalkylation -
products of fatty acids, fatty alcohols, and alkyl phenols -
Cationactive textile auxiliaries -
(b) Capillary inactive compounds -

IV. Pharmaceutical products -

Introduction -
History, chemotherapy, economic aspects -
Classification of pharmaceutical products into groups -

(1) Agents for the prophylaxis and therapy of infectious diseases -
(a) Disinfectants -
(b) Products used in chemotherapy -
Sulphonamides -
Production of sulphathiazole -
Tuberculostatics -
Antibiotics -
Production of penicillin -
Streptomycin and other antibiotics -
Arsenic preparations -
Production of Salvarsan -
Antimony compounds -
Antimalaria agents -

(2) Biocatalysts -

(3) Pharmacotherapeutic compounds -
(a) Compounds acting on the central nervous system -
Narcotics -
Anaesthetics -
Hypnotics -
Antipyretics -
Analgesics -
Pyramidon -
(b) Compounds acting on the peripheral nervous system -
Local anaesthetics -
(c) Compounds acting on the autonomic nervous system  -
(d) Compounds acting on the heart and the blood vessels -
(e) Compounds acting on digestion and diuresis  -

V. Protection of plants and stores (pesticides) -
 
(1) Insecticides  -
(a) Inorganic and vegetable insecticides -
(b) Synthetic insecticides -
DDT group -
Hexachlorocyclohexane (Hexa) and its derivatives -
Organophosphorus compounds -
(c) Insecticides with specific uses -

(2) Ovicides and acaricides -

(3) Fungicides -

(4) Herbicides -

(5) Rodenticides -

VI. Synthetic organic dyestuffs -
Definition -
Colour and constitution -
History -
Development of the dyestuffs industry -
Main manufacturers -

(1) Diaryl- and triarylmethane dyes -
N-alkalized fuchsins -
Hydroxytriarylmethane dyes -
Acridine dyes -

(2) Azine dyes -
Oxazines and thiazines -
Organic pigments -

(3) Sulphur dyes -
General observations on fastness of textile dyes -

(4) Indigo and thioindigo -
Leuco vat dye esters -

(5) Anthraquinone dyes -
(a) Anthraquinone mordant dyes -
(b) Acid dyes of the anthraquinone series -
(c) Anthraquinone vat dyes -
Indanthrone -
Flavanthrone -
Acylaminoanthraquinone and anthrimide -
Anthraquinoneacridones -
pyranthrone and anthanthrone -
Dibenzpyrenequinone -

(6) Perylene dyes -
(a) Violanthrones and isoviolanthrones -
(b) Naphthalene tetracarboxylic acid dyes -

(7) Phthalocyanines -

(8) Azo dyes -
Diazotization -
Coupling -
Equipment for the manufacture of azo dyes -
(a) Azo dyes for wool -
Mono azo dyes -
Disazo dyes -
Chrome dyes -
Metachrome dyes -
(b) Azo dyestuffs for cellulose fibres -
Substantive or direct dyes -
Dyes reacting with cellulose fibre -
Diazotization dyestuffs -
Insoluble dyestuffs produced on the fibre (Naphthol AS dyes) -
(c) Azo dyes for synthetic fibres and leather-
(d) Dyes for foodstuffs, dyes soluble in alcohol, esters, and fat -
(e) Pigments -
Prospects and problems -

(9) The use of textile dyes for dyeing and printing -
(a) Acid dyes -
(b) Chrome and mordant dyes -
(c) Direct dyes -
(d) Vat dyes -
(e) Developing dyes -

VII. Explosives (gunpowder and blasting agents) -

General remarks -
Mode of action -
Manufacture -

(1) Liquid nitric ester (nitroglycerine) -
Manufacture of nitroglycerine -
Nitration of glycol and diglycol -

(2) Nitrocellulose, nitrostarch, nitrosugar, nitrated polyhydroxy compounds -

(3) Aromatic nitro substances -
Picric acid -
Trinitrotoluene -
Tetryl -

(4) Aliphatic nitro substances -
Nitroguanidine -
hexogen -

(5) Liquid air explosives (oxyliquites) -
Testing and evaluation of explosives -

(6) Rocket propellants -
Liquid propellants -
Solid propellants -

Subject -
index -

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