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4: NutraSweet: Chemical Commerce

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    Industrial chemistry is the phrase used frequently to describe the area of commerce that focuses primarily on the manufacture of chemicals or the use of chemicals to manufacture "chemical products."

    This is most evident in the production of ammonia, sulfuric acid, or sodium hydroxide, or in the use of petroleum feedstocks to produce organic materials such as ethylene, styrene, benzene, or caprolactam. In turn, these organics may be converted to the plastics, synthetic rubbers, or fibers that are commonplace in our everyday use. But focusing on such a narrow definition of chemical industry fails to recognize the magnitude of contributions chemists make in the marketplace.

    Reflection on just a portion of a daily routine can articulate the stretch of the chemical world. The perhaps reluctant escape from the synthetic or natural bedding materials followed by a trek across a synthetic or natural carpet into a warm shower to enjoy a sudsy shampoo and soap cleansing begins many a day. The chemist was there, every step of the way.

    textile.jpg (10001 bytes)
    Synthetic textile dyes were first developed in Germany in the 19th century. Virtually all of our textiles are dyed with these organic compounds. This industry is now centered in Asia.
    Chemists make many contributions to the textile and synthetic fabric industry, not the least of which would be the development of colorfast dyes used in all fabrics. The shower soap is more likely to be a synthetic detergent, as is the shampoo. The several other ingredients present in these cleaners would be developed and manufactured by chemists, as would the perfumes that grace most personal care products. The shower water was treated prior to entering the home with a variety of chemicals to purify and sanitize it in some manner. Similarly, the wastewater will likely receive some chemical and biological treatment prior to release into the greater environment.

    Comb your hair with plastics combs and brushes synthesized from chemical feedstocks. Use a synthetic nylon toothbrush and toothpaste formulated by chemists to whiten teeth and protect against decay. Breakfast will consist of foodstuffs made safer and more nutritious by years of research and development by food chemists. Perhaps that will include some Equal in the coffee (decaffeinated by processes developed by chemists) and calcium fortified orange juice. Maybe the long day requires an aspirin before heading out the door. Chemists will have played a role in providing the cement sidewalk and paved driveway that leads to the automobile with an abundance of synthetic plastic parts and a catalytic converter emission system developed by chemists and chemical engineers. The list goes on and on.

    Generally, you will notice only a few units of an end product—one car, a few shampoos, two boxes of cereal, etc. Only when such items are multiplied by millions does one sense the scope of chemical commerce. Dow, DuPont, Exxon, Hoechst Celanese, and Monsanto are five of the leading chemical companies in the world. Among them, sales of chemicals will exceed $60 billion per year. Exxon’s chemical sales, however, represent less than 10% of its revenues as its petroleum component is counted separately. DuPont also, until recently, had a large oil company component. In addition to basic chemicals, Monsanto has a large agricultural chemical segment and is the owner of the NutraSweet company. Agricultural chemistry includes fertilizers, herbicides, and pesticides and is immense in scope on a worldwide basis. The shower soap and shampoo brought to us by a Procter & Gamble, Colgate-Palmolive, Lever Brothers, or a smaller niche manufacturer represent an iceberg tip in the production of household/consumer goods that involve chemistry and chemists as a fundamental contributor. The aspirin comes by way of the pharmaceutical industry, another immense employer of chemistry and chemists. As we understand more and more about how the human body functions, how genes work, how diseases develop, how the body ages, and how the body interacts with foreign substances like drugs, medicinal chemists can better design and synthesize chemical substances that can prevent and control diseases that threaten our well-being.

    This essay is intended only to introduce some aspects of what chemistry is at the commercial level. It is not intended to capture an entire field of chemical industry. If interested, there are several sources available that would allow you to explore the diversity and complexity of the chemical industry. To close this section, it seems of value to emphasize that chemistry is a vibrant, ever-changing area. Billions of dollars go yearly into developing new materials, new processes, and better methods. The manufacture and use of cement may not have changed much in a generation or two, but that is surely not true of many of the chemical items we use. DuPont’s old slogan, "Better living through chemistry," remains valid.

    Societal Issues

    The focus of this case study is NutraSweet, Monsanto’s trade name for aspartame. The use of this synthetic sweetener has raised issues of concern by some and, though it’s not the purpose of this study to dwell on these issues of concern, it is valuable to spend a little time introducing the "dark side" of what is possible in the chemical industry.

    The controversy that surrounds aspartame relates to its safety as a food additive. As indicated elsewhere, a trip to the Internet allows access to many sites that contain information reflecting on the safety of this chemical, even though many short- and long-term studies convinced the FDA that the chemical was safe and the agency approved its use as a sweetener. No one seems to question aspartame’s efficacy—it is indeed a sweet-tasting chemical compound.

    It is difficult to pinpoint a time or an event that represents a turning point when the protection of the greater interests of society and the planet on which we all live became issues to be addressed whenever a product is marketed. In the early part of the century, conditions in slaughterhouses and tainted food brought serious changes to the way meat, fish, and poultry products are brought to the marketplace. We certainly have entrusted the government with the responsibility to protect our well being with regard to how food is processed, recent outbreaks of food poisoning notwithstanding.

    silentspring.jpg (34979 bytes) From Rachel Carson’s seminal work, Silent Spring, has risen an environmental movement that remains very strong today. In particular, the establishment of the Environmental Protection Agency in 1970 formalized the government’s concern with such issues. Clearly, the chemical industry manufactured materials that caused grave damage to the health and safety of many living organisms, as effective in accomplishing their intended tasks as they might have been. Especially damaging were long-lived chemicals such as DDT and PCBs. Air pollution from automotive, power plant, and home heating use of fuel has led to acid rain and concerns for lung damage. Especially bad is the pollution from coal-fired plants, though emission-cleaning techniques are available. All combustion of fossil fuels leads to carbon dioxide (CO2), a rather benign chemical but one whose accumulation in the atmosphere causes concern for its possible greenhouse effect. Use of freons, wonderful chemicals that are safe and do their job well as refrigeration and air-conditioning coolants, leaves us with a depleted ozone layer that, in turn, raises worry about excessive exposure to ultraviolet radiation. Responsible scientists have moved to counter this threat through development of alternative refrigerants that will prove much less harmful. Students enrolled in environmental studies courses will have heard of all these issues and many others. The chemical industry cooperates to sort through toxicological issues at the Chemical Industry Institute for Toxicology (CIIIT)

    Within the past few years, more serious attention has been paid to an area now dubbed "green chemistry." In general, it is an attempt to reduce the risk of environmental contamination and chemical waste. For example, if better catalysts (by definition, a reagent in small quantities that assists a chemical reaction and is itself not consumed) can be developed, then many chemical reactions can reduce the use of catalytic reagents that are less efficient. If byproducts of a reaction can be used in another reaction, then waste can be lessened. If less toxic materials can be used in a chemical process, then health and safety are better protected. If so-called atom efficiency can be maximized, then waste is reduced or eliminated. Atom efficiency relates to converting all the reactant atoms (molecules) into product molecules with no contaminants in the final reaction.

    As an illustration of all of these points, consider the work of Dr. Bill Drinkard at DuPont. Dr. Drinkard invented a direct process for the production of adiponitrile, an intermediate necessary for the production of nylon. Prior to Dr. Drinkard's inventions, the following sequence of reactions gave yielded adiponitrile:

    \[HCN + NaOH \rightarrow NaCN + H2O\]

    \[CH2=CHCH= CH2 + 2HCl \rightarrow ClCH2CH2CH2CH2Cl\]

    \[\ce{NaCN + ClCH2CH2CH2CH2Cl \rightarrow NCCH2CH2CH2CH2CN + NaCl}\]

    Here is a commercial process then that:

    • Requires sodium hydroxide (NaOH) and a process vessel to convert HCN to NaCN and produces waste water.
    • Requires hydrochloric acid (HCl) and a process vessel to react HCl with butadiene.
    • Produces a waste salt (brine).

    Dr. Drinkard invented a catalyst that lowered the activation energy for the reaction of hydrocyanic acid (HCN) with butadiene:


    No waste, a single reaction vessel and a cheaper, more efficient process that requires much less handling and disposal of waste.

    thalidomide.jpg (10545 bytes)
    Thalidomide. This ball and stick model is another way we represent molecular structures. Atoms are color coded and the representation gives us as ense of the three dimensional nature of thalidomide.

    There is only one chiral center in the molecule. Can you find it?

    It turns out that the teratogenic behavior of the thalidomide molecule was caused by ONE of the stereoisomers resulting from this chiral center. The other was perfectly safe..

    Thalidomide, a chemical quite effective as a sedative, was discovered to be a powerful teratogen, a substance that caused birth defects.. In Western Europe, where the drug was approved and widely used, deformed "thalidomide babies" were born in the 1960s. Because of concerns at the FDA, the drug was never approved for use in the United States. It was an incident, however, that made us ever more vigilant in the approval of pharmaceutical products. Consequently, for our protection, several years and millions of dollars are spent on testing new drugs and food additives prior to submitting their use to the FDA approval process. Interestingly, thalidomide, with severely restricted use, returned to the market in 1998 for treatment of HIV/AIDS.

    Most recently, the ability to genetically engineer and alter materials has led to issues of safety and ethics. What is society’s best interest in using recombinant DNA technology to produce a bovine growth hormone, an insect-resistant potato, or a new drug?

    Nothing that we do is without risk—to our own well being, to the well being of a large group, or to society. It is important that we balance risk and benefit. There are many more questions than answers and few of the answers are simple ones. Few chemistry courses address issues associated with the use of the chemicals we study. You might want to stimulate some conversation by introducing such issues into questions you might ask.

    Intellectual Property Rights

    The importance of intellectual property is recognized in Article 1 of the U.S. Constitution. Much of today’s commerce is based on the recognition that an idea developed into a product is protected for a period of time and that the purveyor of the idea or product can profit accordingly. The Department of Commerce, through its Patent and Technology Office, issues patent protection for inventions. Product trademarks are also registered with that office.

    NutraSweet is a registered trademark for Monsanto’s aspartame product and the processes by which the compound is manufactured are patented. When patents expire, as they have for NutraSweet, then other manufacturers are likely to legally produce the now "generic" chemical and the price will usually drop once competition arrives. The patent protection will usually allow a period of 20 years for the originator of the product to recoup its costs of research and development and marketing. Profits will also likely pay for research into other products that may never reach the marketplace and, naturally, return some gain to investors.

    All developed countries have patent offices and most countries will recognize patent protection to a product that originates elsewhere. A World Intellectual Property Organization assists the cooperative efforts of member countries. We read much about pirated music and videos as well as counterfeit apparel and consumer goods. Nike, Gucci, SONY, and Disney are just four of the thousands of companies that are vigilant for unauthorized manufacture and dissemination of fraudulent materials. Trademark names are valuable assets, as are the various products that are produced.

    4: NutraSweet: Chemical Commerce is shared under a not declared license and was authored, remixed, and/or curated by ChemCases.

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