Electrochemistry Encyclopedia --- Industrial organics

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INDUSTRIAL ORGANIC ELECTROSYNTHESIS

With Some Advice on Approaches to Scaleup
Norman L. Weinberg
Consultant
East Amherst NY, USA
E-mail: nweinberg@adelphia.net
(May, 2002)
Thousands of electrochemical reactions of organics have been catalogued to date. These comprise direct electron transfer reactions at
anodes for oxidation and at cathodes for reduction. Thousands of these also include indirect electron transfer reactions using redox
species. Of these, not more than a few hundred pilot and industrial scale organic electrosyntheses have been described (see Tables I-III
below for examples).
The essential difference between chemical and electrochemical processing is that the reactor is an electrolytic cell powered by a current
source. The electrolytic cell contains positively charged anodes and negatively charged cathodes; an electrolyte solution containing ions to
carry the current and in which the reactant and product are usually at least partially dissolved; maybe, separators (membranes or porous
diaphragms) to separate the processes at the anodes and cathodes; and, some means for stirring or agitating the cell contents. The
electrodes may be made of special catalytic material, that is these may be electrocatalytic coatings with special properties for optimizing
the yield, increasing product specificity, extending electrode life, and/or lowering cell voltage. The electrodes are preferably spaced as
close together as possible without touching to avoid shorting, so as to minimize the cell voltage (See Economics).The dc power supplies
or rectifiers electrify the cell, at relatively low cell voltages usually in the range of about 3 to 15 volts.
There are many other differences seen in organic electrosynthesis compared to conventional organic synthesis. Useful concentrations of
highly reactive cation or anion radicals, not easily or so far impossible to make chemically, can be easily and conveniently produced
electrochemically. The resulting electrosynthesis products can be unique (that is not before synthesized by chemical means, or so
difficultly made by chemical means that many steps would be required). Many other reactive species can be made conveniently, including
superoxide ion, hydroxyl radicals, peroxide, CO2 anion radicals, hydrogen atoms and metal hydrides, and halogens, including fluorine. On
the cathode side of the cell, at high negative potentials, solutions of solvated electrons can be readily made and on the anode side, at high
positive potentials, powerful oxidants like fluorine, persulfate salts, and ozone. Acid can be made at the anode and alkali at the cathode.

Advantages and disadvantages of electrosynthesis

There are advantages and disadvantages to organic electrochemical processing. Most important among the advantages is the very wide
range of oxidation and reduction reactions possible. Other advantages that may be realized are: significantly less energy requirement; less
hazardous process; elimination or minimization of polluting byproducts requiring disposal; process simplification so that an otherwise
multistep chemical route is simplified to one or two steps; use of cheaper more readily available starting materials; the possibility of

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reaching very high levels of product purity and selectivity; development of valuable intellectual property; and, in many instances,
considerably improved capital and operating costs over conventional methods.
Electrosynthesis certainly has disadvantages too. Electrosynthesis usually requires the use of a solvent to solubilize the reactants and
products. Water is the ideal solvent but too often organic solvents or co-solvents are required. In addition, supporting electrolytes to carry
the current are very often needed. The solvent/supporting electrolyte system can be too expensive or even the source of unacceptable
pollutants if not recovered and recycled. Electrolytic cells require stable electrode materials, separators and other components, which may
have limited lifetimes and can affect the economics adversely. Electricity is required in all electrochemical processing which may or may
not be a critical factor, depending on where the process is located. (Note, however, that the cost of electricity is not at all a deciding factor
where higher value added products such as pharmaceuticals are the products).
Considering the advantages, critics question why there are so few commercial scale organic electrosyntheses. Indeed, there are many
ongoing successful processes (See Tables I-III), but as in conventional processes, some have been discontinued or may never reach
commercial scale for various reasons, including:

The product became a pollutant (for example tetraalkyl lead from lead and alkyl halide);
The market for the product disappeared (for example 1,2-dihydrophthalic acid);
An established market for the products never existed (for example Philip's electrofluorination of hydrocarbons). A new process for
a new product is bound to have a tough upward battle to achieve market entry;
Toxic byproducts could not be eliminated (for example p-aminophenol produced from nitrobenzene is contaminated with
carcinogenic benzidine);
Improved methods of catalytic hydrogenation became more practical (for example sorbitol from glucose or aniline from
nitrobenzene);
Methods of catalytic oxidation became more practical (for example hydroquinone from benzene or phenol or propylene oxide from
propylene);
The capital cost is considered too high for the company in its present financial state.
Courage! For various reasons, the product or process has no upper level corporate "champion" willing to support it, despite the
promising opportunity and economics;
Politics! If the company manufactures this product, the company perceives it may lose an important customer or partner, who may
see this as competition.

It should not be surprising that the above list of reasons why electrochemical processes never reach commercialization or are discontinued
pertains to conventional processing as well.

Chemical industry's attraction to electrosynthesis

The advantages cited above are good reasons for companies to be aware of advances in electrochemical processing. There are also good
reasons for chemical companies to have on hand at least the basic laboratory tools and the necessary skills to evaluate potential
electrochemical routes alongside conventional methods. But, all too often the primary reason why companies investigate electrochemical
processing alternatives is because the company has tried every conceivable chemical method available without success. Then someone in
the company, perhaps an electrochemist, an external consultant, or a scientist reading the literature has asked if electrosynthesis might be
the long-sought answer. In reality, except for rare instances, there are usually no easy electrosynthesis answers, if no chemical route
works.

Attaining successful industrial organic electrochemical processes

The importance of adopting a strategic approach cannot be overemphasized, especially where a company does not have the necessary inhouse expertise. Reaching an informed decision on whether or not to pursue a proposed electrochemical route requires consideration of all
of the following:

The electrochemical literature, including patents on the electrosynthesis of the product and its nearest analogues.
For the most promising route, write the equations for the anode and cathode processes, including products and byproducts. Then
decide what needs to be demonstrated in the laboratory in a limited series of studies during small scale feasibility testing. Usually

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some electroanalytical method such as cyclic voltammetry is useful to follow the electrooxidation or electroreduction of the
reactants. Calculate the cell voltage (if not indicated in the literature) and estimate the cell requirements, the electrode area and the
number of cells. And, do at least a first pass economic evaluation of capital and operating costs.

If not already performed, compare the economics of the most promising chemical route. Based on the economics, decide on what
variables, if any, are likely to be critical in the electrochemical route. Nothing can be done about certain factors like the number of
electrons required, the molecular weight of the starting material or products, but the economics may be influenced positively, for
example, by increasing the product yield, current efficiency and selectivity, or by lowering the cell voltage, and by the choice of
solvent, operating temperature and cell components like electrode and separator materials.
A limited number of the feasibility experiments are performed in the laboratory using a simple cell. Glass cells and small flow cells
are commercially available. Is the desired product formed? What are the yields and current efficiencies of the products and
byproducts? If the answers are found acceptable, a series of well designed experiments will normally follow, preferably in a small
flow cell with good flow characteristics to begin to optimize some of the critical variables of the early experiments. All along the
way, "go/no go" decisions will be made. Further work may be discontinued in a "no go" decision upon discovery of unacceptable
byproducts or the requirement of a too expensive solvent.
Recalculate the economics, based on the results to this point.
If still promising, the engineering team may come in to produce a preliminary process flow diagram and assist with advice and
design of the scale facility.
In many instances, especially for high value added products, pilot
scale may be the plant scale. Designing your own
electrochemical cell may be unnecessary. Modern cells are
highly engineered reactors and are commercially available in a
variety of sizes and with a range of cell components (Figure 1).
The following are a few companies that offer cells:

ElectroCell http://www.chematur.se/
IneosChlor http://www.ineoschlor.com/
Progenica http://www.electrosynthesis.com/
C-Tech http://www.capenhurst.com/

Successful pilot scale evaluation of electrochemical processes

initially requires set up of the electrolytic cell, power supply,
pumps, flow meters, piping, and controls to adequately simulate
what is expected for the plant. The immediate objectives of
piloting are proving that the process is viable at larger scale and
for longer continuous running. A a rule of thumb, the initial scale
can be as little as say production of 1/4 to 1 kg/day of product or
Fig. 1. An example of electrosynthesis cells:
an order of magnitude higher. The minimum continuous running
Progenica Cell (Photo reproduced with
time for deeming a process technically promising is 1000 hours.
permission of Regenesys Technologies Limited).
During that period, investigators look for sustained high product
yields, purity, and current efficiencies. Any surprises in byproduct
formation, stability of cell components, especially electrodes and
membranes, increasing cell voltage, etc. may cause reassessment of the process. Experience shows that most problems begin to
show up within 1000 hours of operation. The next section delves into engineering considerations critical to the success of the
process.

Engineering considerations
After successful R&D/preliminary economics, the optimization of the commercial process requires attention to:

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Mass transfer
The rate of mass transfer of reactants and products across the boundary layer at the electrode can be improved by:
A.
B.
C.
D.
E.
F.
G.

Rotation of a cylindrical or disc electrode: capital investment high

External pumping of electrolyte between the electrodes, with or without turbulence promoters
Turbine or propeller agitators
Fluidized bed of electrode particles: capital investment high
Fluidized bed of non-conducting particles
Vibration of the working electrode: capital investment high
Gas sparging

The majority of commercial electrochemical cells are parallel plate designs with: (a) external electrolyte pumping, or (b) gas sparging

Heat transfer
Removal of heat generated within cells is usually required for maintaining the optimum electrolysis temperature. This is accomplished by:
A. Circulation of electrolyte through external heat exchangers: the most predominant method
B. Internal cooling of the cell via coils, jackets or tubes
C. Internal or external evaporative cooling
Factors in sizing the total heat removal load include calculation of:
A.
B.
C.
D.
E.

Electrolysis power input

Heats of reaction of main and side reactions
Heat input of electrolyte pumps
Heat removed from: humidification of off gasses, evaporation of solvent, reactant, products, or by products
Heat required to bring the electrolysis system feed stream to operating temperature

Power usage
The power usage is a function of cell voltage and current efficiency, but it will be also influenced by the current leakage in bipolar cells,
parasitic electrode reactions, pumping losses, and rectifier losses.

Electrode life
The corrosion, passivation, and fouling of both anodes and cathodes can only be evaluated after many months of testing. Electrode life
can be greatly affected by:
A.
B.
C.
D.

Electrochemically induced corrosion

Chemical reaction with solvent, products, or byproducts
Too high an operating current density
Mechanical breakage resulting from:
a. high stresses in a cell
b. internal gas pocketing, especially in porous electrode materials, such as carbons
c. handling, reuse and long term "wear and tear"
E. Fouling from corrosion products, electrolyte impurities, products, and byproducts

Separator life
The performance of separators, whether porous diaphragms or ion exchange membranes can only be evaluated after many months of
testing. Separator materials can be greatly affected by:
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A.
B.
C.
D.
E.

Chemical reaction with solvent, products, or byproducts

Dissolution in solvent, products, or byproducts
Too high an operating temperature
Too high an operating current density
Mechanical breakage resulting from:
a. unbalanced electrolyte pressures
b. unsupported membranes under turbulent flow conditions
c. internal gas pocketing
d. handling, reuse and long term "wear and tear"
F. Fouling from corrosion products, electrolyte impurities, products, and byproducts

Solvent/supporting electrolyte quality

The buildup of impurities from corrosion and reaction byproducts can only be evaluated after months of pilot testing. Such byproducts can
be severely detrimental to overall process performance and optimal performance of cell components. To rectify this situation, it may be
necessary to provide for a purge stream or solvent/ supporting electrolyte clean-up step to increase quality.

Economics of industrial electrosynthesis

The economics for the electrochemical portion of the process is governed by operating and capital costs as presented in more detail in the
Appendix. For the best economics, it can be seen that low cell voltage, high current density, high current efficiency, and high product
selectivity are needed.

Examples of commercial scale and piloted organic electrochemical processes

Tables I-III below list typical examples of on-going commercial scale processes, piloted processes which have not reached
commercialization, and processes which had been commercialized but discontinued for various reasons. More exhaustive compilations
can be found in the literature. In addition there are many more electrosynthesis processes, especially of fine chemicals, which are kept
proprietary and are not found in the open literature.
Two systems are selected as most interesting examples:
1. The production of adiponitrile (ADN) is important because this compound in used in the production of the well-known plastic:
nylon. The electrohydrodimerization of acrylonitrile (ACN) to adiponitrile is the largest scale commercial electroorganic process,
with an estimated total production worldwide of about 340,000 metric ton/year. Discovered by Manuel Baizer in the early 1960's,
the "Monsanto Process" was relatively quickly brought to commercialization by a team headed by Donald Danly. Their equipment,
cell designs and cell parts such as membranes and electrode materials were primitive by modern standards. Baizer's key innovation
was discovery that quaternary ammonium salts such as tetraethylammonium p-toluenesulfonate greatly increased the yield and
current efficiency of the conversion of acrylonitrile to adiponitrile (see chemical equation in the Appendix).
The modern-day process uses cadmium cathodes and steel anodes in a bipolar cell containing no membranes, with a two phase
recirculating aqueous emulsion of ACN, ADN, a bisquaternary salt (hexamethylene(bisethyltributyl)ammonium phosphate),
phosphate buffer, and the anode anticorrosion additives, borax and EDTA. The process is conducted at 55oC (131oF) and a current
density of 2 kA/m2. A fraction of the organic phase is continuously removed from the emulsion reservoir for separation of the
product. The aqueous phase also is treated continuously to prevent accumulation of organic byproducts and metallic salts from
electrode corrosion.
2. An excellent example of an innovative industrial organic electrosynthesis process is the following. This process was developed at
BASF and was described by Hermann Putter in 1999, at the 13th International Forum on Applied Electrochemistry. This paired
4000 metric ton/year process yields two valuable products simultaneously, phthalide and t-butylbenzaldehyde, by electrolysis in an
undivided bipolar capillary gap cell with graphite electrodes (see chemical equation in the Appendix). Other important features of
this process are:

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This is the first commercial example of a paired organic electrosynthesis (useful products are produced both on the anode
and on the cathode).
Methanol is both a reagent and a solvent: as much methanol is released from reduction of the diester as is consumed in
making t-butylbenzaldehyde.
Current density is 0.1 to 1 kA/m2 at a cell voltage of 4 to 7 volts.

Table I. Commercial processes

Product

Starting material

Company

Acetoin

Butanone

BASF

Acetylenedicarboxylic Acid

1,4-Butynediol

BASF

Adipoin Dimethyl Acetal

Cyclohexanone

BASF

Adiponitrile

Acrylonitrile

4-Aminomethylpyridine

4-Cyanopyridine

Reilly Tar

Anthraquinone

Anthracene

L. B. Holliday, ECRC

Azobenzene

Nitrobenzene

Bleached Montan Wax

Raw Montan Wax

Hoechst

Calcium Gluconate

Glucose

Sandoz, India

Calcium lactobionate

Lactose

Sandoz, India

S-Carbomethoxymethylcysteine

Cysteine + Chloroacetic Acid

Spain

L-Cysteine

L-Cystine

Several

Diacetone-2-ketogulonic Acid

Diacetone-L-sorbose

Hoffman-LaRoche

Dialdehyde Starch

Starch

India, Others

1,4-Dihydronaphthalene

Naphthalene

Hoechst

2,5-Dimethoxy-2,5-dihydrofuran

Furan

BASF

Furfuryl-1-ethanol

Otsuka

Dimethylsebacate

Monomethyladipate

Asahi Chemical

Gluconic Acid

Glucose

Sandoz, India

Hexafluoropropyleneoxide

Hexafluoropropylene

Hoechst

m-Hydroxybenzyl Alcohol

m-Hydroxybenzoic Acid

Otsuka

Mucic Acid

Galacturonic Acid

EDF

Perfluorinated hydrocarbons

Alkyl substrates

3M, Bayer, Hoechst

2,5-Dimethoxy-2,5-dihydrofuryl-1-ethanol

Phthalide + t-Butylbenzaldehyde Acetal

Dimethyl Phthalate + t-Butyltoluene

Monsanto (Solutia), BASF, Asahi Chemical

BASF

p-Methoxybenzaldehyde

p-Methoxytoluene

BASF

Polysilanes

Chlorosilanes

Osaka Gas

p-t-Butylbenzaldehyde

p-t-Butyltoluene

BASF, Givaudan

Salicylic Aldeyde

o-Hydroxybenzoic Acid

India

Succinic Acid

Maleic Acid

CERCI, India

3,4,5-Trimethoxybenzaldehyde

3,4,5-Trimethoxytoluene

Otsuka Chemical

3,4,5-Trimethoxytolyl Alcohol

3,4,5-Trimethoxytoluene

Otsuka Chemical

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Table II. Piloted processes/not yet commercialized

Product

Starting material

Company

1-Acetoxynaphthalene

Naphthalene

BASF

Acetylenedicarboxylic Acid

2-Butyne-1,4-diol

BASF

2-Aminobenzyl Alcohol

Anthranilic Acid

BASF

Anthraquinone

Naphthalene, Butadiene

Hydro Quebec

Arabinose

Gluconate

Electrosynthesis Co.

Dimethyl Maleate

Monsanto

1,2,3,4-Butanetetracarboxylic Acid
Ceftibuten

Electrosynthesis Co., Schering Plough

Cephalosporin C
3,4,5,6-tetrachloro-picolinic Acid

3,6-Dichloropicolinic Acid

Dow

Ditolyliodonium Salts

p-Iodotoluene, Toluene

Eastman Chemical, Electrosynthesis Co.

Ethylene Glycol

Formaldehyde

Electrosynthesis Co.

Glyoxylic Acid

Oxalic Acid

Rhone Poulenc, Steetley

Hydroxymethylbenzoic Acid

Dimethyl Terephthalate

Hoechst

Monochloroacetic Acid

Tri- and dichloroacetic Acid

Hoechst

Nitrobenzene

p-Aminophenol

India, Monsanto

5-Nitronaphthoquinone

1-Nitronaphthalene

Hydro Quebec

Partially Fluorinated Hydrocarbons

Alkanes and Alkenes

Phillips Petroleum

Pinacol

Acetone

BASF, Diamond Shamrock

Propiolic Acid

Propargyl Alcohol

BASF

Propylene Oxide

Propylene

Kellog, Shell

Substituted Benzaldehydes

Substituted Toluenes

Hydro Quebec, W.R. Grace

Future trends
Table III. Discontinued commercial processes
Product
1,2-Dihydrophthalic Acid

Starting material

Company

o-Phthalic Acid

BASF
L. B. Holliday, BASF

2-Methyldihydroindole

2-Methylindole

Hexahydrocarbazole

Tetrahydrocarbazole

L. B. Holliday, BASF

Piperidine

Pyridine

Robinson Bros.

Sorbitol

Glucose

Hercules

Tetraalkyl Lead

Alkyl Halide, Pb (anode)

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Nalco

Based on the past, one can comfortably predict

that the future of industrial organic
electrochemical processing is promising.
Certainly discovery and commercialization of
high value added products will continue and at a
much lesser pace some inroads will be made
towards electrochemical manufacture of
commodity chemicals so that adiponitrile does
not stand as the only example of large-scale
production. Perhaps the prize will be
electrosynthesis of ethylene glycol or an olefin
oxide like propylene oxide. With the advent of
less expensive cells and cell components and
discovery of new electrocatalytic materials new
opportunities could arise that would have been
impractical years before. For example, it has

Electrochemistry Encyclopedia --- Industrial organics

been speculated that one day commercialization of an electroenzymatic process will occur. This would be based on the application of
enzymes as catalysts, dissolved in the electrolyte solution or fixed to a support, such as an electrode or separator. The goal would be to
harness the extraordinary abilities of enzymes to produce highly valuable, unusual products, perhaps having high stereoselectivity.
Realization of an industrial scale electroenzymatic process may take many years to fulfill, but work is already underway in a number of
laboratories worldwide to one day achieve this goal.
There are at this writing no academic institutions where courses in applied electrochemistry are taught. In the USA, the closest disciplines
taught are electroanalytical chemistry and electrochemical engineering. Fortunately, there is a large literature of resource materials,
including excellent books (see Bibliography). Electrochemical Society meetings (http://www.electrochem.org) and other international
symposia, such as the Annual International Forum on Applied Electrochemistry (http://www.electrosynthesis.com) are excellent meetings
to explore ideas and find assistance from experts in the field.
What is available also to help those interested in applied organic electrosynthesis are many commercial cells of flexible design; stable cell
components, including catalytic electrodes, highly selective membranes and a number of novel electrode/membrane composites; a sound
theoretical and practical knowledge base in electrochemistry and electrochemical engineering; and, experienced groups that can advise on
R&D, engineering, plant design, construction, and start-up.

Appendix
Electric power consumption
K = ( 100 Ko n F V ) / ( Mp Ec )

Cell costs
A = ( 1.12 103 n P ) / ( Mp i Ec )
where:

K =
Ko =

power cost, (US)cents/kg

n =
F =

number of electrons taking part in the reaction

Faraday, 26.8 Ah/mole

V =
Mp =

cell voltage, V

Ec =

current efficiency, %

local power cost, (US)cents/ kWh

molecular weight of product, g/mole

electrode area (for electrode used in the conversion),

m2
P = production rate, kg/day
A =

To calculate an approximate cell cost, using the above determined

electrode area requirement, use $10,000/m2 for larger installations (say,
>10 m2) and $15,000/m2 for smaller installations (<10 m2). Theses
figures include electrodes (anodes and cathodes), membranes, frames,
spacers, gaskets or o-rings, end-plates and cell fittings for electrolyte,
and electrode connections. Contact the cell manufacturer to determine an
exact cell cost. For the best economics, it can be seen that low cell
voltage, high current density, high current efficiency, and high product
selectivity are needed.

Conversion of acrylonitrile to adiponitrile

2 CH2 = CHCN + 2 H + + 2 e - ==> NC-CH2CH2CH2CH2-CN

current density, A/m2

Simultaneous production of phthalide and t-butylbenzaldehyde

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Related articles
For other industrial electrolytic processes see:
Aluminum production
Brine electrolysis
Extracting metals from sulfide ores

Bibliography

Organic Electrochemistry (4th edition), H. Lund and O. Hammerich (editors), Marcel Dekker, New York, 2001.
Perspectives: The Last 15 Years and Beyond, N. L. Weinberg in "Proceedings of the 15th Annual Forum on Applied
Electrochemistry" Electrosynthesis Company, Lancaster NY, 2001.
Electrolytic ProcessesPresent and Future Prospects, Electrosynthesis Company and Dextra Associates, Report Number TR107022, EPRI, Palo Alto CA, 1997.
Principles of Electrochemical Engineering and Scaleup, D. E. Danly in "Proceedings of the 5th Annual Forum on Applied
Electrochemistry" Electrosynthesis Company, Lancaster NY, 1991.
Industrial Electrochemistry (2nd edition), D. Pletcher and F. C. Walsh, Chapman and Hall, London, 1990.
ElectrosynthesisFrom Laboratory to Pilot, to Production, J. D. Genders and D. Pletcher (editors), Electrosynthesis Company,
Lancaster NY, 1990.
Proceedings of the Annual Forum on Applied Electrochemistry (15 volumes), Electrosynthesis Company, Lancaster NY, since
1987.

Emerging Opportunities for Electroorganic Processes, D. E. Danly, Marcel Dekker, New York, 1984.

Techniques of Electroorganic Chemistry (Part III), N. L. Weinberg and B. V. Tilak (editors), Wiley Intersciene, New York, 1982.

Workshop on the Status of Industrial Organic Electrochemistry, SRI International, EPRI EM-2173, Project 1086-9, Research
Reports Center, Box 50490, Palo Alto CA, 1981.
A Survey of Organic Electrolytic Processes, T. R. Beck, R. Alkire, and N. L. Weinberg, DOE Contract Number 31-109-4209,
Report No. ANL/OEPM-79-5, Argonne National Laboratory, Argonne IL, 1979.

Listings of electrochemistry books, review chapters, and proceedings volumes are also available in the Electrochemistry Science and
Technology Information Resource (ESTIR). (http://electrochem.cwru.edu/estir/)

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The Encyclopedia is hosted by the Ernest B. Yeager Center for Electrochemical Sciences (YCES) and the Chemical
Engineering Department, Case Western Reserve University , Cleveland, Ohio.
Copyright Notice.
Edited by Zoltan Nagy (nagy@anl.gov) The Center for Electrochemical Science and Engineering and Department of Chemical
and Environmental Engineering, Illinois Institute of Technology, Chicago, Illinois.

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