Industrial Organic Chemicals (Wittcoff/Organic Chemicals) || How to Use Industrial Organic Chemicals, Second Edition

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CHAPTER 0

HOW TO USE INDUSTRIAL ORGANICCHEMICALS, SECOND EDITION

Industrial Organic Chemicals, published in 1996, was an updated, expanded, andcompletely rewritten version of volume I of a two-volume set, Industrial OrganicChemicals in Perspective, published in 1980. Volume I of the set described whereindustrial organic chemicals came from; volume II described how they were used.Two decades later, chemicals still come from the same sources, but there are manynew processes to be described. The application of chemicals has changed much less,and a revision of volume II is not planned. This second edition of the 1996 book iswarranted by the numerous changes the industry has undergone in a short time. Wediscuss many new processes and improvements in many older ones.

0.1 WHY THIS BOOK WAS WRITTEN AND HOW IT IS STRUCTURED

The petrochemical industry provides well over 95% by tonnage of all organic chem-icals. It grew rapidly in the 1950s and 1960s. Many new processes and products wereintroduced. Large economies of scale proved possible. The prices of chemicals andpolymers dropped so that they could compete with traditional materials. Cheerfullycolored plastic housewares, highly functional packaging, shampoos that toleratedhard water and easy care garments of synthetic fibers were no longer exciting newtechnology. Instead they had become an accepted and routine part of modern life.

Industrial Organic Chemicals, Second Edition, by Harold A. Wittcoff,Bryan G. Reuben, and Jeffrey S. PlotkinISBN 0-471-44385-9 Copyright © 2004 John Wiley & Sons, Inc.

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By the 1970s, growth was leveling off. The first and second oil shocks increased theprice of crude oil, and hence of its downstream products. Economies of scale suffered ahiatus to rise again in the late 1990s with the announcement of 2.2 billion lb of ethyleneper year steam crackers and a 3.5 billion lb per year methanol plant. In 2004, SABICannounced plans for a 2.9 billion lb/year cracker. The industry had matured. As its tech-nology became better known, developing countries started their own petrochemicalindustries, competing with the developed countries and thus depressing profitability.Furthermore, the impact of the industry on the environment became evident.

In the 1980s and early 1990s, new products were no longer the name of the game,in part because the 1960s and 1970s had provided an arsenal of them to attack newapplications. Also, the industry became subject to strict government monitoring.Expensive toxicity testing was required before a new compound could be introduced.(Section 1.3.7).

Rather than developing bigger, better plants to manufacture novel chemicals, theindustry became concerned with lessening pollution, improving processes, anddeveloping specialty chemical formulations and niche products that could be sold athigher profit margins. Research and development became highly process oriented, inpart to find less polluting processes, and in part to combat maturity and gain an edgeover competition with money-saving technology. Examples are given in the fore-word and throughout the book.

Chapter 1 shows how the chemical industry fits into the overall economy and thendefines the industry in terms of its characteristics.

Chapter 2 describes where organic chemicals come from and then shows how themajor sources, petroleum and natural gas, provide seven basic chemicals or chemicalgroups from which most petrochemicals are made. The basic building blocks com-prise olefins—ethylene, propylene, and the C4 olefins (butadiene, isobutene, 1- and 2-butenes); aromatics—benzene, toluene, and the xylenes (ortho, meta, para); andone alkane, methane. Chapter 2 explains how the olefins derive primarily from steamcracking and secondarily how C3 and C4 olefins come from catalytic cracking, andhow the aromatics derive primarily from catalytic reforming in the United States butfrom steam cracking in Europe. Methane occurs as such in natural gas. The chapteremphasizes the important interface between the refinery and the petrochemical indus-try and the relationship between feedstock flexibility and profitability.

Chapters 3 and 4 describe the chemistry of ethylene and propylene. They are themost important of the seven building blocks and are treated accordingly.

Chapters 5 and 6 deal with the C4 and C5 olefins. Chemical usage of C4 olefins(excluding methyl-tert-butyl ether for gasoline) is an order of magnitude less thanthat of ethylene and propylene, and the major C4 applications are in synthetic rub-bers. The C5 compounds and their derivatives are only used in much lower volumeand are not included in the seven basic building blocks. They are nonetheless animportant source of isoprene for a synthetic analogue of natural rubber (Section15.3.10) and for thermoplastic elastomers (Section 15.3.8).

Chapters 7–9 describe the chemistry of the aromatics—benzene, toluene, and thexylenes. Benzene has been overshadowed by ethylene and propylene since the 1960sbut is still the third most important of the building blocks.

2 HOW TO USE INDUSTRIAL ORGANIC CHEMICALS

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Chapter 10 describes the chemistry of methane, a relatively unreactive molecule,which nonetheless is the source of synthesis gas (CO � H2) for ammonia andmethanol manufacture. Acetylene is discussed here, since it may be made frommethane. Very important 50 years ago, its significance has been steadily diminishedby chemistry based on ethylene and propylene.

Chapter 11 is devoted to the growing industrial chemistry based on alkanes otherthan methane. The substitution of alkanes for olefins, which depends on sophisticatedcatalyst development, could change industrial chemistry profoundly in the future.

Chapters 12–14 deal with non-petroleum sources of chemicals—coal, fats andoils, and carbohydrates. The chemical industry in the nineteenth and early twentiethcenturies was based on chemicals derived from coal tar or coke oven distillate.Today, this is a specialty area, and our major interest in coal focuses on its conver-sion to synthesis gas. This would be the first stage in building a coal-based chemi-cal industry should petroleum and natural gas be depleted.

The chemistry of fats and oils (Chapter 13) is reflected in the surfactant areaand in numerous specialty performance products. Carbohydrate-based chemicals(Chapter 14) are also largely specialties.

Since over one-half of all organic chemicals manufactured end up in polymers,Chapter 15 is devoted to polymerization processes and polymer properties. Chapter16 deals with the all-important subject of catalysis without which there would hardlybe a chemical industry. Chapter 17 discusses the vital issue of sustainability, and theemergence of “green” chemistry, a topic that dominates the books published onindustrial chemistry since 1990.

It is these new processes and attitudes that provided the incentives for this newvolume, but we have also expanded its scope to include many apparently less impor-tant reactions, which are significant because they give rise to the more profitable spe-cialty chemicals. We hope it will be useful both to university students who havestudied organic chemistry and to graduates and industrial chemists who work in orare interested in one of the most remarkable industries of the twentieth century and,if we may anticipate a little, the twenty-first century.

We intend each chapter to be self-sufficient, hence there is inevitably a degree ofrepetition. We have tried to minimize this by extensive cross-referencing and hopethe reader will be tolerant of the repetition that remains.

0.2 NORTH AMERICAN INDUSTRY CLASSIFICATION

The US government provides statistics on all branches of industry, dividing themaccording to the North American Industry Classification System (NAICS). Eachmajor segment of the economy is classified under a number between 1 and 99(Table 1.1). Manufacturing industries are classified under numbers 31–33 and thechemical and allied products industry falls within this category at 325. Statistics forsubsegments of the industry are provided under four, five, or six digit numbers.Thus 3252 is Resins, synthetic rubbers & artificial & synthetic fibers and filaments,325211 is Plastics materials and resins, 325212 is Synthetic rubber, and 32522

NORTH AMERICAN INDUSTRY CLASSIFICATION 3

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Artificial & synthetic fibers and filaments. We have relied on these data, although itis never possible to obtain up-to-date figures. Thus the material published in 2002contains information for 2000. Statistics from other sources are often more up-to-date but are less authoritative (Section 0.4.5).

The industries that form the chemical and allied products industries are shown inTable 1.2. Although at times one might wish for even more detailed information, theNorth American Industry Classification provides a wealth of it. Other countries donot have comparable databases; many have Standard Industrial Classifications, butnone provides so much information. The classifications in other countries rarely cor-respond to those in the United States or to each other, and analysts wishing to tackleofficial statistics should be aware of the pitfalls.

0.3 UNITS AND NOMENCLATURE

The widespread adoption of the SI (Système International) system of units based onthe meter, the kilogram, and the second has worsened rather than improved theplethora of units used in the chemical industry. Three kinds of tons are in commonuse—the short ton (2000 lb), the metric ton or tonne (1000 kg or 2204.5 lb), and thelong ton (2240 lb). U.S. Statistics are usually given in millions of pounds, which areat least unambiguous, and we give all our figures either in these units or in tonnes.In addition, we try to quote figures in the units actually used by industry—petroleumis measured in barrels, benzene in gallons, mixed xylenes in gallons, and (incredi-bly) p-xylene in pounds—to give conversions in better known units. A table of con-version factors is given in Appendixes 2 and 3.

Similarly, in naming chemicals, we tend to use the names conventional in indus-try rather than the more academic nomenclature of the International Union of Pureand Applied Chemistry (IUPAC). Thus we write hydrogen not dihydrogen; ethylene,acetylene, and acetic acid; not ethene, ethyne, and ethanoic acid.

Industry makes no effort to use consistent nomenclature. Ethene and propene areuniversally known as ethylene and propylene and would scarcely be recognized by theirIUPAC names. The C4 olefins, however, are frequently referred to as butenes rather thanbutylenes and we have followed this style. We use trivial names wherever industry does.Thus we refer to C6H5CH(CH3)2 as cumene, the name by which it is bought and sold,rather than the more informative names of isopropylbenzene, 2-phenylpropane, or (1-methylethyl)benzene. The term ethanal would be likely to be misread or misheard inindustry as ethanol, and the compound is known as acetaldehyde. So important is triv-ial nomenclature that the pharmaceutical industry could not exist without it.

We regret the lack of consistency that the use of trivial nomenclature entails, butwe feel it best serves our aim of communicating with chemical industry personneland preparing students to enter the industry.

0.4 GENERAL BIBLIOGRAPHY

In many ways, the greatest service that a book like this can provide is to introducethe student to the industrial chemical literature. We follow each chapter with an


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annotated bibliography that lists some of the standard literature on the subject of thechapter, cites the sources of much of our own information, and adds occasional notesto matters discussed in the chapter. Two of the authors of this book received theirbasic education many years ago, and we have listed unashamedly the books thatinfluenced us, aged though they may be. We have omitted some of the truly obsoletematerial. References to early work, as well as more recent material, may be found inKirk–Othmer and other encyclopedias, and in B. G. Reuben and M. L. Burstall, TheChemical Economy, Longman, London, 1974. Relatively few books have beenwritten recently on the chemical industry and much can still be gained from the oldones.

0.4.1 Encyclopedias

The most important single reference work is R. E. Kirk and D. F. Othmer, Kirk–Othmer’s Encyclopedia of Chemical Technology, Volumes 1–25, 4th ed., J. I. Kroschwitzand M. Howe-Grant, Ed., Interscience, New York, 1991–1998. Kirk–Othmer providescomprehensive and well-referenced coverage of almost every aspect of industrial chem-istry. New articles appear on the web (www.mrw.interscience.wiley.com/uric or www.mrw.interscience.wiley.com/kirk) and these will eventually be included in a 5th edition.The earlier volumes of the first, second, and third editions are inevitably dated, but pro-vide information not readily available from other sources. If a subject is not treated inthe new edition, it is always worth consulting the older one.

The Encyclopedia of Polymer Science and Engineering, 2nd ed., J. I. Kroschwitz,Ed., (17 volumes plus supplement and an index volume) Interscience, New York,1985–1989, provides comprehensive coverage of polymer chemistry. It is well ref-erenced but weak on technology. The first edition (called The Encyclopedia ofPolymer Science and Technology) comprised 15 volumes and was published between1964 and 1971. As with The Encyclopedia of Chemical Technology, the earlier edi-tion still contains valuable material. Part 1: Volumes 1– 4 of the 3rd ed. (reverting tothe original title, H. F. Mark, Ed.) had been published by June 2003.

The Encyclopedia of Chemical Processing and Design, J. J. McKetta, Ed.,Dekker, New York, has a chemical engineering orientation. It had run to 68 vol-umes by 1999. As publication started in 1976, it is perhaps inevitable that theapproach is inconsistent. Individual articles are worthwhile but the content isunpredictable.

The only encyclopedia to rival Kirk–Othmer is Ullmann’s Encyclopedia of Indus-trial Chemistry, W. Gerhartz, Ed., Wiley-VCH, Weinheim. It was first published in1914 and this, the 6th ed., appeared as a 40-volume set in October 2002. A rapidinspection suggests rigorous editorial control, with well-indexed chapters followinga standard pattern. It has a more international approach than Kirk–Othmer.

An ambitious undertaking is the Dictionary of Scientific and Technical Terms,S. P. Parker, Ed. The 4th ed. was published by McGraw-Hill in 1989. Two newerventures are R. D. Ashford, Dictionary of Industrial Chemical Properties, Productionand Uses, 2nd ed., Wavelength, London, 2002, and A. Comyns, EncyclopedicDictionary of Named Processes in Chemical Technology, CRC Press, Cleveland OH,1999.

GENERAL BIBLIOGRAPHY 5

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Some consulting companies publish reports on a continuing basis that contain awealth of up-to-date information on chemistry, engineering, and markets of numer-ous industrial chemicals. These are, however, quite expensive and are usually foundonly in industrial libraries, the subscriber agreeing to keep the information confi-dential. One such program is entitled Process Evaluation and Research Planning(PERP Program) Nexant Inc./Chemsystems, 44 South Broadway, White Plains, NY10601-4425, which covers in depth the chemistry, engineering, and market data formany of the basic petrochemicals as well as important specialty chemicals. A less in-depth compendium but one that covers a greater breadth of subjects is the ChemicalEconomics Handbook, Stanford Research Institute, Menlo Park, CA.

0.4.2 Books

Before the spectacular growth of the chemical industry after World War II, three clas-sic books appeared that encompassed much of what was done up to 1950. Thesebooks have been repeatedly revised and updated and, although they seem old-fashioned in some ways, they are certainly worthy of mention. The oldest is Riegel’sHandbook of Industrial Chemistry, 9th ed., J. A. Kent, Ed., Van Nostrand–Reinhold,New York, 1992. Riegel first appeared in 1928 and is now a multiauthor survey of thechemical and allied products industry. R. N. Shreve and N. Basta, The ChemicalProcess Industries, 6th ed., McGraw-Hill, New York, 1994, was first published in1945 and covers many of the process industries such as cement and glass as well asthe mainstream chemical industry. Faith, Keyes and Clark’s Industrial Chemicals firstappeared in 1950. The fourth and most recent edition was revised by F. A. Lowenheimand M. K. Moran and was published by Wiley-Interscience in 1975. It is now out ofprint. It provides details of manufacture and markets for the 140 most importantchemicals in the United States and is significant because of its interdisciplinaryapproach, which has never been repeated.

Another volume of note is Chemistry and the Economy, M. Harris and M. Tischler,Eds., American Chemical Society, Washington DC, 1973. Although old, it provides anexcellent overview of the impact of chemical technology on the economy. It describeshow industrial chemistry interfaces with numerous industries, gives insight into themakeup of the chemical industry, and provides numerous historical facts that tend tohumanize the industry. The book is good reading for students as well as for practicingchemists and engineers.

In the 1970s, interest increased in the teaching of industrial chemistry in collegesand universities. There is still a long way to go to impress the academic communitywith the important role that industrial chemistry has played not only in the applicationof chemical technology but also in the development of new knowledge. Nonetheless,a number of important books were published.

One of the first books on industrial organic chemistry was J. K. Stille, IndustrialOrganic Chemistry, Prentice Hall, Englewood Cliffs, NJ, 1968. This small volume,now out of print, contains a wealth of material about the industry as it existed priorto 1970 and is written from the interesting perspective of an academic organicchemist.


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The Chemical Economy, B. G. Reuben and M. L. Burstall, Longman, London,1974 is a guide to the technology and economics of the chemical industry and pro-vides an overview of the industry emphasizing organic chemicals. It is biased some-what toward European practice and contains annotated bibliographies.

Basic Organic Chemistry V: Industrial Products, J. M. Tedder, A. Nechvatal, andA. H. Jubb, Eds., Wiley, Chichester, 1975, is the fifth volume of a series on organicchemistry, but the title is somewhat misleading as the book can stand by itself as atextbook on industrial organic chemistry. It comprises a multiauthor survey, orientedtoward chemistry rather than technology and toward British practice. Insufficientreferences are given. The book is a mine of information for the specialized readerand has been reprinted but not revised.

C. A. Clausen, III, and G. Mattson, Principles of Industrial Chemistry, Wiley-Interscience, New York, 1978, is aimed at chemists and is a collection of case stud-ies providing an enthusiastic introduction to chemical process principles, processdevelopment, and various commercial aspects of the chemical industry. A morerecent collection is E. Lister and C. Osborne Industrial Chemistry Case Studies,Royal Society of Chemical Education Division, London, 1998.

A. L. Waddams, Chemicals from Petroleum, 4th ed., John Murray, London, 1978,was a pioneering account of petrochemicals and provides an insight into the rela-tionship of the refinery to the chemical industry.

Among the important books dealing specifically with the organic chemicalsindustry is P. Wiseman, An Introduction to Industrial Organic Chemistry, 2nd ed.,Halsted Press, New York, 1979. It is well organized, well written, and is orientedtoward the pure chemistry that provides a base for technology. The same author pro-vided Petrochemicals, Ellis Horwood, Chichester, 1986.

J. Wei, T. W. F. Russell, and M. W. Swartzlander, The Structure of the ChemicalProcessing Industries, McGraw-Hill, New York, 1979, is similar in structure to TheChemical Economy (loc. cit.) but deals primarily with the economic structure of theindustry and much less with technology.

At the end of the 1970s appeared our two-volume work, H. A. Wittcoff and B. G. Reuben, Industrial Organic Chemicals in Perspective, Part I: Raw Materialsand Manufacture, and Part II: Technology, Formulation and Use, John Wiley & Sons,Inc., New York, 1980. Part I concentrated on the production of organic chemicalsfrom seven major building blocks, while Part II dealt with the downstream sectors ofthe chemical industry, detailing the chemistry that was involved in the use of chemi-cals for plastics, fibers, elastomers, surface coatings, adhesives, surface active agents,pharmaceuticals, solvents, lubricating oils, plasticizers, agrochemicals, food chemi-cals, and dyes and pigments. Both volumes were reprinted by Krieger, FL, in 1990.

The 1980s and early 1990s saw some new editions but relatively few new bookson industrial organic chemistry. W. S. Emerson, Guide to the Chemical Industry:R&D, Marketing and Employment, Wiley-Interscience, New York, 1983, reprintedby Krieger, FL, 1991, provides useful insights into how the industry functions, butthe technical part contains several unfortunate errors.

Chemicals are discussed from the point of view of the consumer in an interesting andoriginal book, B. Selinger, Chemistry in the Market-Place, 5th ed., Australian National


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University Press, Canberra, 1998. Selinger is a pioneer of the Australian consumermovement and chaired a committee on toxic waste disposal. He describes the formula-tion of many domestic products together with the reasons for the various additives andthe theory behind them. An explanation of everyday chemicals whose presence in prod-ucts may puzzle consumers is to be found in G. R. Lewis, 1001 Chemicals in EverydayProducts, 2nd ed., John Wiley & Sons, Inc., New York, 1999. It describes in dictionaryformat many chemical products, mixtures such as creosote and general terms such ashallucinogen, together with the answers to “consumers” chemical questions’.

An English translation of the 4th ed. of K. Weissermel and H. J. Arpe, IndustrialOrganic Chemistry, VCH, Frankfurt appeared in 2003. Like the 1976 first edition, itis beautifully laid out, easy to follow, highly accurate, and concentrates on theupstream large tonnage processes.

H. Szmant, Organic Building Blocks of the Chemical Industry, John Wiley & Sons,Inc., New York, 1989, contains a wealth of information even about small tonnagechemicals and emphasizes practice at the end of the 1980s. It lists the prices at the timeof publication of all the chemicals it mentions and illustrates vividly the adding ofvalue as chemicals further and further downstream of the oil refinery are produced.

P. J. Chenier, Survey of Industrial Chemistry, 3rd ed., Kluwer Academic-Plenum,New York, 2002, contains well-written thumbnail sketches of about a hundred industrialorganic chemicals plus a few inorganics. It describes some economic aspects of theindustry but is strongly United States oriented and lacks an international dimension.Handbook of Chemicals Production Processes, R. A. Meyers, Ed., McGraw-Hill, NewYork, 1986, describes lucidly 40 industrial processes, divided between organics, inor-ganics, and polymers.

S. Matar and L. F. Hatch, Chemistry of Petrochemical Processes, 2nd ed., GulfProfessional Publishing, Boston, 2001 is a competent exposition of petrochemicals,weak on social and economic implications but redeemed by excellent flow diagrams.Regrettably the 2nd ed. is changed only slightly from the first.

C. A. Heaton has edited two books of note: An introduction to IndustrialChemistry, 2nd ed., Blackie, London 1991, and The Chemical Industry, 2nd ed.,Blackie, London, 1993. The UK Society of Chemical Industry published TheChemical Industry, D. H. Sharp and T. F. West, Eds., Ellis Horwood, London, 1981,to celebrate their centenary. It contains “a glance back and a look ahead at prob-lems, opportunities and resources . . .” Industrial Chemistry, vol. 1, E. Stocchi, EllisHorwood, London, 1990, appeared to be the start of a series but was largely devotedto inorganic chemicals and no further volumes have yet appeared. The IndustrialChemistry Library is a somewhat off-beat series, publishing books on topics gener-ally neglected. For example, G. Agam, Industrial Chemicals, their Characteristicsand Development, Elsevier, Amsterdam, The Netherlands, 1994, deals entertaininglywith the things that academic chemists in general do not know about formulations,specifications, standards, assays, scale-up, safety, patents etc. In the same series isThe Roots of Organic Development, J.-S. Desmurs and S. Ratton, Eds., Elsevier,Amsterdam, The Netherlands, 1996.

An historical perspective of the chemical industry that is interesting for anyone whois engaged in it as well as to academics who want insight into how basic chemistry is


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translated into technology is P. H. Spitz, Petrochemicals: The Rise of an Industry,Wiley, New York, 1988. This book can be highly recommended. Other historiesinclude F. Attalion, The History of the International Chemical Industry, University ofPennsylvania Press, PA, 1991, and H. L. Roberts, Milestones in 150 years of theChemical Industry, P. J. T. Morris, Ed., Royal Society of Chemistry, London, 1991.Morris has also edited From Classical to Modern Chemistry: the Instrumental Revolu-tion, Royal Society of Chemistry, London, 2002, which deals with the impact thatadvances in instrumentation, especially in environmental analysis and process control,have had on what chemists and chemical engineers do and how they think about theirsubject. The UK Chemical Industries Association has produced Development of theUK Chemical Industry: a Historical Review, CIA, London, 2000.

In mid-2003 M. M. Green and H. A. Wittcoff, published Organic ChemicalPrinciples and Industrial Practice, Wiley-VCH, Weinheim, 2003. As its name indi-cates, it relates the theory of organic chemistry to the important industrial reactionsthat derive from that theory, and how these in turn impact on daily living.

0.4.3 Journals

A serious student of the chemical industry must follow the trade press. New prod-ucts and processes, changes in the structure and prospects of the industry, take-oversand trades, mergers and demergers, as well as economic trends, can all be followed.

A selection of news magazines for English-speaking readers includes Chemical andEngineering News (weekly, ACS, Washington, DC); Hydrocarbon Processing(monthly, Gulf Publishing, Houston, TX); Chemical Week (weekly, Chemical WeekAssociates, New York, there are European and US editions); European Chemical News(weekly, Reed Business Information, London); Modern Plastics (Chemical Week Asso-ciates, New York), Chemistry and Industry, (fortnightly, Society of Chemical Industry,London); Chemistry in Britain, (monthly, Royal Society of Chemistry, London)relaunched in January 2004 as Chemistry World; Manufacturing Chemist (weekly,Morgan Grampian, London); and Chemical Market Reporter (weekly, SchnellPublishing, New York). European Chemical News provides US and European prices ofthe major bulk chemicals. A sister publication, Asian Chemical News, was started in1994. Chemical Marketing Reporter carries a comprehensive tabulation of US listprices of almost all widely sold chemicals.

CHEMTECH (monthly, ACS, Washington, DC) replaced Industrial andEngineering Chemistry in 1971 and was founded by Ben Luberoff as an ideas mag-azine rather than a news magazine. It aimed to be conceptual and at the same timeto humanize chemistry. Luberoff retired and subsequently died in 2001. The journalwas renamed Chemical Innovation in 2000 but, without Luberoff’s dynamism, itceased publication by the end of 2001.

0.4.4 Patents

Patents are a device whereby the government grants inventors the sole right toexploit their inventions for 17 years in the United States (until recently), 20 years in


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the European Community and similar periods in other countries. In return, the inven-tors disclose details of their inventions in their patent specifications. Recent legisla-tion in the United States has extended the life of a pharmaceutical patent to 22 yearsunder certain circumstances and similar patent term restoration has been enacted inEurope. As a result of the GATT (General Agreement on Tariffs and Trade) negoti-ations, the United States has extended patent protection for 20 years; however, thetime clock starts from the date of application instead of issuance.

Patents lie at the heart of a developed society. It is difficult to see how innovationcould take place if innovators were not rewarded for their efforts. “I knew that a coun-try without a patent office . . . was just a crab,” said Mark Twain, “and couldn’t travelany way but sideways or backwards.” Meanwhile, the patent literature has grownexponentially. In the United States, it took about 200 years to amass four millionpatents, the four millionth having been issued in 1976. It took only 15 years to accu-mulate one million more patents and US Patent 5,000,000 was issued on 19 March1991 to L. O. Ingram et al. It described the use of modern biotechnology to produceone of the oldest synthetic organic chemicals—ethanol.

Patent specifications are a major source of technical information. They often dis-close information at a much earlier date than the scientific literature; sometimes theyare the only source of such information. Negative results often appear in patents butnot in scientific journals, and knowledge of what has been tried without success maysave the working scientist much time.

Academic scientists shun patents because the introductions and claims are writ-ten in legal jargon with long convoluted sentences. Librarians shun them becausethey are published as individual items and are difficult to collect and bind. Theyhave, however, one overwhelming advantage. They are classified by subject and canbe subscribed to in this way, a copy of a US patent costing $3.00. They may also beobtained free on the Internet.

Patent applications are numbered consecutively as they are received by the USPatent Office (US serial number) and, when the patent is granted, it is assignedanother number (US patent number). Other patent offices do the same.

Brief accounts of patents appear in the chemical trade literature. Chemical Abstractspublishes a numerical patent index that lists each patent number together with its cor-responding Chemical Abstracts abstract number, country of origin, and serial number.It also provides a worldwide list of major patent offices and their addresses. ChemischesZentralblatt (Akademie Verlag, Berlin) offers a similar service together with a guide toits use. (Chemisches Zentralblatt: das System). Derwent (Thomson/Derwent, 14 GreatQueen Street, London WC2 5DF, UK) publishes analyses and abridgements of patentsfrom every country classified by subject, and provides monthly bulletins, for example,Organic Patents Bulletin and Pharmaceutical Patents Bulletin. Derwent has contributedgreatly to making patent literature available.

The Official Gazette, copies of patents, coupon books (a convenient way to payfor copies), listings of patents by subject, copies of foreign patents, and much otherinformation may be obtained from the Commissioner of Patents and Trademarks,Washington, DC 20231. Although many official and commercial organizations existto help the student of the patent literature, a thorough search can be conducted onlyat the National Patent Library, Washington, DC.


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In the United Kingdom, the equivalent of the Official Gazette is the Patents andDesign Journal (PDJ), and it and other information are available from the PatentOffice, Concept House, Cardiff Road, Newport, NP10 8QQ. The departure of theOffice from London has been compensated for by a Central Inquiry Unit, telephone0845 9500505, web site www.patent.gov.uk. A thorough search can be carried out atthe British Library (Patents Section), 96 Euston Road, London NW1 2DB.

Information on subject codes and many other aids to patent searching may befound in Kirk–Othmer (cited in Section 0.4.1). Highly praised for its clarity andsound advice is The Business of Invention, P. Bissel and G. Barker, Wordbase,Halifax, West Yorkshire, UK.

Access to patents has been simplified greatly by computerized searching ofpatent databases of which Derwent, Chemical Abstracts, Inpadoc and esp@cenetare the most important (Section 0.4.6). The United States (www.uspto.gov),European (www.european-patent-office.org/inpadoc) and British Patent Offices(gb.espacenet. com) are all on line. Delphion Research, founded in 2000, hasestablished an intellectual property network that can be subscribed to at a varietyof levels ranging from full premier membership to a one-day pass. It enables oneto perform text searches of United States, European, and Japanese patents, plusother intellectual property resources. Searching can be done by patent number orsubject. WIPO, the World Intellectual Property organization, based in Geneva,produces many CD-ROM and online publications dealing with the state-of-play ofpatents throughout the world. This has become more important as more countrieshave come into line with the GATT (General Agreement of Trade and tariffs)regulations.

Although use of these databases requires skill, the user is rewarded by the accessthese bases provide to vast amounts of information. It is said that the Japanese havebeen able to accomplish a great deal in the chemical industry because of their skillin reading and interpreting patents. As the industry becomes more and more com-petitive, it is important to monitor trends, to know what other companies are doingand to avoid duplication. The patent literature can contribute more than any othersource to “knowing what your neighbor is doing,” an important concept in today’stechnical world where an inventor can bring a new frame of reference to someoneelse’s invention to create new and unanticipated goods and services.

0.4.5 Statistics

Students of the commercial side of the chemical industry will require access to sta-tistics of production and consumption. Comprehensive US statistics were formerlypublished annually by the US International Trade Commission as Synthetic OrganicChemicals: United States Production and Sales. Publication ceased after 1994 on thespurious grounds that the data were available from other sources. The NationalPetroleum Refiners Association (NPRA) took over some of the operation and makesthe information available to members.

Figures for the major chemicals plus much information about companies, employ-ment, and related topics are published more rapidly in Chemical and EngineeringNews at the end of June or the beginning of July of the subsequent year. Thus the data


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for 2001 were published in the June 24, 2002 edition. An important major source isthe annual Guide to the Business of Chemistry, American Chemistry Council., 1300Wilson Blvd., Arlington,VA 22209.

On a worldwide basis, The United Kingdom Chemical Industries Association(CIA has a quite different meaning in the US) (www.chemical-industry.org.uk);King’s Buildings, Smith Square, London SW1P 3IJ) publishes statistical reviews,notably Basic International Chemical Industry Statistics 1963–1996, London, 1997,and Main World Chemical Markets by Geographic Area, 1996–2010 (Published occa-sionally; formerly Chemical Industry Main Markets). The former provides charts andtables for Western Europe, the United States, and Japan.

The Chemical Industry in 2000: Annual review, production and trade statistics,1997–1999, United Nations, New York, 2001, is the latest of an annual compilationby the Economic Commission for Europe. Until 1988, it was published as the AnnualReview of the Chemical Industry. Chemical Industry Europe, United Business Mediainternational information services, Tonbridge, 2001, is a CD-ROM containing indus-try statistics.

Detailed statistics may be obtained rather belatedly from Government sourcesin most countries. In the United Kingdom, disaggregated figures appear relativelyquickly in the Business Monitor, HMSO, London, and are summarized in, for exam-ple, Business Monitor, Report on the Census of Production, summary volumes pub-lished occasionally, HMSO, London.

In Europe, too, many useful data and some comments are published by the industryassociation CEFIC (Centre Européen des Fédérations de l’Industrie Chimique) and bytheir subsidiary APPE, the Association of Petrochemicals Producers in Europe, whoproduce an annual Activity Review of exceptional interest. CEFIC often does not provide hard copy, but their material is easily available online at www.cefic.org andwww.petrochemistry.net. They have as members a range of associations dealing withlower olefins, aromatics, acetyls, acrylonitrile, amines, ethanol, acrylic monomers, plas-ticizers and intermediates, fuel oxygenates, ethylene oxide and derivatives, methanol,phenol, propylene oxide and glycols, oxygenated solvents, hydrocarbon solvents,styrene, and coal tar chemicals. Each contributes its own reports.

CEFIC has produced a splendid interactive flowsheet, tracing the steps that turncrude oil into petrochemicals and petrochemicals into everyday products. It is to befound at www.petrochemistry.net/flowchart//index.htm.

0.4.6 CD-ROM and On-Line Databases

When the authors of this book were starting in the chemical industry, informationabout the industry was sparse in the United States and practically nonexistent inEurope. Hoffman la Roche in 1967, at the time the world’s largest pharmaceuticalcompany, published no accounts, investment figures, or costs. They declared a profitof $9.3 million and stated “The result for the year 1966 again shows improvementover the year before. Sales and earnings have increased in approximately equalproportions . . . the volume of investment was again large and will hardly diminishin the foreseeable future.” Assiduous marketers would spend their time trying to pick


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up fragments of information and weave them into a coherent pattern. The difficultywas to obtain the information in the first place. Since then, legal requirements fordisclosure have forced companies to publish more about their activities, and theadvent of CD-ROM, on-line databases and the internet have meant that the problemtoday is not to obtain information but to sift what is reliable from what is dubious orjust plain wrong.

Available databases are listed in the Gale Directory of Databases, M. Faerber andM. E. Williams, Eds., Gale Research, Detroit MI, published annually in two vol-umes, the first dealing with on-line databases and the second with CD-ROM,diskette, magnetic tape, handheld, and batch access database products. The increas-ing popularity of the internet, its speed, and the improved search engines (we useGoogle, Yahoo, and Alta Vista) have meant that the CD-ROM disk (updated, say, atmonthly intervals) is being displaced by direct online linkage to sites where a sub-scription is necessary to gain access. Vendors maintain systems for dialing into them.Typical of scores of vendors is STN International, whose United States address is c/oChemical Abstracts Service, 2540 Olentangy River Road, PO Box 3012, Columbus,OH 43210–0012. In the United Kingdom, access to most scientific databases isthrough MIMAS, Manchester Computing, University of Manchester, Kilburn Build-ing, Oxford Road, Manchester M13 9PL. The most important databases are those ofthe Institute of Scientific Information (ISI), known as the ISI Web of Knowledge(www.isinet.com/isi). Starting with a science citation index, they now also operatesocial science, and arts and humanities indexes.

Chemical information is widely available. Sources of online patent informationare listed in Section 0.4.4. Online technical information may be obtained fromChemical Abstracts and the Science Citation Index via ISI. Information on marketsand technology is provided by Promt, a University of Pittsburgh database. Engi-neering information, once listed in the Engineering index, is now available from EiCompendex, Ei Compendex Plus, and Ei Chemdisc. As far as we know, these are stillCD-ROM-based and originate from Palo Alto, CA, Dialog Information Services. Forcommercial information, we rely heavily on Chemical News Intelligence (CNI) andInsite Pro. The former is an arm of Reed Business Information, which publishesnumerous magazines and journals, and abstracts only Reed’s information. Insite Prois available through Dialog and abstracts many magazines.

The Royal Society of Chemistry, Thomas Graham House, Science Park, MiltonRoad, Cambridge CB4 4WF, UK, produces a Chemical Business Newsbase dealingwith the commercial environment of the chemical industry, which is international butbiased toward Western Europe. There is a general business database ABI Inform Global/Wall Street Journal, which abstracts chemical industry journals such as Chemical andEngineering News, Chemical Market Reporter, Chemical Week, and Modern Plastics.The coverage is largely North American but there is an invaluable extension calledBusiness Periodicals Ondisc, which provides full text of many articles on the main data-base. Uncover (uncweb.carl.org) is a database of multidisciplinary journals, which pro-vides tables of contents. Articles can then be ordered directly or by fax.

BEST (Building Expertise in Science and Technology, Longman Cartermill,Technology Centre, St. Andrews, Fife, Scotland KY16 9EA) is produced by the


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British Council and is the official national database of current research and expert-ise in U.K. universities and colleges. It maintains records of scientists and engineersand what they are doing. It is widely used as a repository of technical information tosupplement what one might get out of a patent search.

Finally, and extremely useful, are the Chemical Company Annual Reports that arepublished online. Among the color photographs of Chief Executive Officers, nuggetsof valuable information are often to be found. They can all be accessed by a searchengine.

The Internet is a virtual world on its own, and surfing it is a skill that must belearned. Books on it are numerous, and appear so rapidly that it is not worthwhilelisting them. We mention S. M. Bachrach, The Internet: A Guide for Chemists, ACS,Washington, 1996, because it focuses on chemists’ needs, but in general we advisestudents to spend a couple of hours learning the intricacies of their search engines,so that they can reduce the length and increase the specificity of their searches.


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Industrial Organic Chemicals (Wittcoff/Organic Chemicals) || How to Use Industrial Organic Chemicals, Second Edition