Industrial Manufacturing Process Quality Ccntrcl
Evaluation Series • 01/79-06
Toxic Pollutant
Identification:
CATALOGUEOF ORGANIC CHEMICAL
INDUSTRIES-UNIT PROCESSES
-=—I *2_»M" r-^-Jl
U.S. ENVIRONMENTAL PROTECTION AGENCY
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01/79-06
January 1979
EPA - IMPQCE Series
TOXIC POLLUTANT IDENTIFICATION:
CATALOGUE OF ORGANIC CHEMICAL PRODUCTS
UNIT PROCESSES
by
ELBERT C. HERRICK
JOHN A. KING
The MITRE Corporation
METREK Division
McLean, Virginia 22101
Grant No. 805620
Technical Advisor: Paul E. desRosiers
Project Officer: David R. Watkins, IERL-CI
U.S. ENVIRONMENTAL PROTECTION AGENCY
INDUSTRIAL AND EXTRACTIVE PROCESSES DIVISION
OFFICE OF ENERGY, MINERALS AND INDUSTRY
OFFICE OF RESEARCH AND DEVELOPMENT
WASHINGTON, D.C. 20460
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TABLE OF CONTENTS
Page
1.0 INTRODUCTION/SUMMARY 1
2.0 CONCLUSIONS/RECOMMENDATIONS 3
2.1 Conclusions 3
2.2 Recommendations 3
3.0 NEED FOR THE UNIT PROCESS CATALOG 4
3.1 Regulatory Background 4
3.2 Unit Process Regulation 14
4.0 METHODS USED TO CREATE THE CATALOG 17
4.1 Overview 17
4.2 Identification of Principal Commercial 18
Chemicals
4.3 Identification of Unit Processes 19
4.4 Identification of Manufacturing Processes 20
5.0 STRUCTURE AND USES OF THE CATALOG 21
5.1 Major Unit Processes 21
5.2 Minor Unit Processes 23
5.3 Index of Chemicals Produced by Unit Processes 24
5.4 How to Use the Unit Processes Catalog 25
6.0 UNIT PROCESS CATALOG 27
6.1 Major Unit Processes . 27
6.2 Minor Unit Processes 27
6.3 Index of Chemicals Produced by Unit Processes 27
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TABLE OF CONTENTS (Continued)
Page
6.4 Definitions of Unit Processes 27
6.4.1 Major Unit Processes 27
6.4.2 Minor Unit Processes 72
6.5 Directory of Companies Owning/Licensing
. Manufacturing Processes 72
BIBLIOGRAPHY ' 103
APPENDIX A DEFINITIONS OF MAJOR UNIT PROCESSES A-l
APPENDIX B DEFINITIONS OF MINOR UNIT PROCESSES B-l
APPENDIX C DIRECTORY OF COMPANIES OWNING AND/OR
LICENSING DESCRIBED PROCESSES C-l
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LIST OF ILLUSTRATIONS
Figure
3-1 Environmental Regulation Scenario
LIST OF TABLES
Table
3.1 Federal Toxic Classification Systems 11
6.1 Major Unit Processes - Summary 28
6.2 Major Unit Processes 29
6.3 Minor Unit Processes - Summary 73
6.4 Minor Unit Processes 74
6.5 Index of Unit Processes and Feedstocks for 77
Manufacture of 263 Commercial Organic Chemicals
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1.0 INTRODUCTION/SUMMARY
More than 10,000 chemical manufacturing and processing firms
employ 1.1 million Americans, with sales of about 100 billion dollars.
Chemical industry products represent some 7.5 percent of the U.S.
Gross National Product. Over the past 10 years, the industry has
enjoyed an annual growth rate nearly twice that of the Gross National
Product. New chemicals represent about 10 percent of all patents
issued in the United States from 1836 to 1970. Today, there are over
30,000 chemical substances in commerce, and another 3 to 4 million in
research and development, and as many as 1500 new ones entering the
market every year.
By virtue of the Toxic Substances Control Act and several other
statutes enacted in recent times, both the toxic pollutants and chem-
ical products are now regulated, forcing the Environmental Protection
Agency to consider the intra-process sources of toxic chemical dis-
charges to the air, water and solid media as well as the intra-process
sources of toxic contaminants. There is an enormous multiplicity of
chemical manufacturing operations and the task associated with
environmental assessment of so many processes is awesome. Therefore,
the U.S. Environmental Protection Agency may consider assessment of
the 41 generic "unit process" reactions which comprise the building
blocks for chemical manufacturing operations.
This "Catalog of Unit Processes" identifies the 41 commercially
significant unit processes used in more than 5000 plants to manufacture
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the 263 principal chemicals in U.S. commerce. It provides the basis
to begin systematic environmental assessment of the 41 unit processes
as they are utilized in chemical industry today.
Forthcoming reports will evaluate the pollutant and product con-
tamination risks of the 41 unit processes to facilitate environmental
assessment for the 263 primary organic chemicals of commerce.
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2.0 CONCLUSIONS AND RECOMMENDATIONS
2.1 Conclusions
Most of the manufacturing processes widely used in chemical
industry today consist of "unit process" components that carry out the
fundamental chemical reactions in organic synthesis (e.g., nitration,
amination by ammonolysis, etc.). The unit processes are the basic
building blocks of chemical manufacturing operation. For most commer-
cial applications of a given unit process, the physical and organic
chemistry tends to be common or alike.
Through systematic examination of the process chemistry associated
with the unit processes, one can identify the air, water and solids
discharges as well as the potentials for product contamination for
commercial chemical manufacturing operations.
The first challenge in carrying out such an assessment is the
survey of the commercially used chemical manufacturing operations to
determine (1) which unit processes are in commercial use, and (2)
which unit processes are used for each commercial application. The
product of this effort is embodied in this "Catalog of Unit Processes".
The catalog verifies that (1) the 41 unit processes in commercial use
may be meaningfully defined and (2) for the 263 primary chemicals in
commerce, the unit processes used to manufacture them may be defined.
In the course of surveying the unit processes currently in commercial
use, it also became apparent that they fall into two major groups:
(1) major unit processes used in large-volume chemical production
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and (2) minor unit processes used in smaller-scale, yet significant
production. These two groups of unit processes are listed in
Tables 6.1 and 6.2 (pages 28 and 71) respectively.
2.2 Recommendations
Because of the commonality of physical and organic chemistry and
the discharges associated with use of the unit processes, they should
be the focal point for an assessment of potentials and risks for toxic
waste discharges and products contamination in the chemical industry.
Many manufacturing operations used throughout the process industries
(i.e., chemical, textile, paper, rubber, plastics, dyes, detergents)
may be environmentally assessed by virtue of unit process assessment.
The first unit processes to be evaluated should be those most likely
to release toxic chemicals (i.e., amination, nitration).
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3.0 NEED FOR THE UNIT PROCESS CATALOG
3.1 Regulatory Background
Today 12 Federal statutes are involved in control of pollution,
and human environmental exposure to "toxic chemicals":
(1) (TOSCA) Toxic Substances Control Act of 1976, PL 94-469.
(2) (FDCA) Food, Drug and Cosmetic Act as amended in 1976.
(3) (OSHA) Occupational Safety and Health Act of 1970, PL 91-596.
(4) (CPSA) Consumer Product Safety Act of 1970, PL 92-573.
(5) (Ocean Dumping) Marine Protection, Research and Sanctuaries
Act of 1972, PL 92-532.
(6) (FIFRA) Federal Insecticide, Fungicide and Rodenticide Act
as Amended in 1972, PL 92-516.
(7) (CAA) Clean Air Act as Amended in 1977, PL 95-95.
(8) (FWPCA) Federal Water Pollution Control Act Amended in 1977,
PL 92-500. Clean Water Act of 1977, PL 95-217.
(9) (SDWA) Safe Drinking Water Act of 1974, PL 93-523.
(10) (RCRA) Resource Conservation and Recovery Act of 1976,
PL 94-580.
(11) (HMTA) Hazardous Materials Transportation Act.
(12) (NEEPA) National Environmental Policy Act of 1969.
Regulatory action required by these focuses on toxic chemicals in
wastes and products, their identification, sources, control, safe
handling, discharge to the environment and ultimate disposal. The
regulatory scenario of the future, assuming regulations will be issued
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under all 12 statutes, can be summarized in the chart Figure 3-1 on
the page to follow.
There are two principal problems created by this scenario:
(1) the closed cycle for materials flow and the potential for toxic
chemical accumulation at various points in the chemical manufacture,
use and disposal cycle in concentrations or forms that may pose toxic
hazards to mankind, and (2) the potential for conflicting regulations.
The projected modes of regulation for toxic chemicals in the future
are as follows:
(1) Consumer uses of chemicals may be regulated under Consumer
Product Safety Act; Toxic Substances Control Act; Federal
Insecticide, Fungicide and Rodenticide Act; and Food Drug
and Cosmetic Act, depending on the type of product or mode
of use.
(2) Workplace conditions in power and manufacturing plants
are regulated by Occupational Safety and Health Act, water
discharges by Clean Water Act, solid discharges by Resources
Conservation and Recovery Act and air discharges by the
Clean Air Act.
(3) Air pollution control facilities emissions are regulated
under Clean Air Act, and produce solid wastes regulated
under Resources Conservation and Recovery Act and waste
waters (scrubber waters) regulated by Clean Water Act.
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AIR RELEASE TO AMBIENT
Power
Plants
(OSHA)
Plants
{OSHA
Solid
Wastes
Waste Water
Treatment
Landfill
or Ocean
Dumping
Surface
and
Ground
Waters
RCRA
FWPCA
SDWA
Ocean Dumping Act
Figure 3-1 Environmental Regulation Scenario
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(4) Water pollution control facilities, both industrial and
municipal, discharge treated waters to navigable waters
under Clean Water Act regulations and to drinking water
supplies under Safe Drinking Water Act. Water pollution
control facilities generally generate solid wastes regulated
under Resources Conservation and Recovery Act.
(5) Solid waste disposal procedures may be regulated by:
(a) the "Ocean Dumping Act",
(b) the Clean Air Act (air emissions from incineration),
(c) the Resources Conservation and Recovery Act and Safe
Drinking Water Act (due to ultimate potentials for
toxic chemical impacts on drinking water supplies).
In the case of a chemical manufacturing operation for which the
Toxic Substances Control Act may call for washing of a product to
remove a potentially toxic contaminant, wastewater containing the
contaminant will be thus generated. If the toxic material falls
within one of the 131 chemical species designated by the Clean Water
Act Section 307 (a), the wastewater must be treated to remove the
toxic material. Treatment of the wastewater to remove the toxic
material may lead to generation of a solid waste bearing the same
toxic material, and management of this solid material must then
comply with forthcoming regulations to be administered under the
Resources Conservation Recovery Act. If the only option for ultimate
disposal of the solid waste bearing toxic materials is incineration,
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then the emissions from the combustion will be regulated under Section
111 or 112 of the Clean Air Act.
One resolution to this potential dilemma is modification of the
process itself, or the feedstocks, to eliminate the generation of the
toxic materials. If this approach is adopted, end-of-pipe treatment
would not be necessary since toxic discharges have been eliminated.
One of the first of the three toxics regulation issues at hand
is definition of toxic chemicals. The first step, as viewed by several
Federal agencies, involves development of a unified working definition
for toxic risk and testing methods. The second step is collection of
extensive data to confirm toxic risks and for identification of the
toxic materials to be regulated. The Environmental Protection Agency
and other Federal agencies have announced intentions to focus regu-
latory activity on the few chemicals that are "the most harmful".
The four key Federal agencies principally involved are the Environ-
mental Protection Agency, the Consumer Product Safety Commision, the
Food and Drug Administration and the Occupational Safety and Health
Administration.
The Toxics Committee of the Council for Environmental Quality and
the Inter-Agency Research Liaison Group (with members from Environ-
mental Protection Agency, Food & Drug Administration, Consumer Product
Safety Commission and Occupational Safety & Health Administration)
are addressing definition of toxic and otherwise hazardous materials
or chemicals. Table 3.1 illustrates the diversity of toxic chemical
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TABLE 3.1 FEDERAL TOXIC CLASSIFICATION 'SYSTEMS
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Environmental Protection Agency
Office of Pesticides
Environmental Protection Agency
Ocean Dumping Act
National Institute for Occupational Safety
and Health - Toxic Substances List
Environmental Protection Agency
Drinking Water Program
Water Pollution Act Sec. 304 (a) (1)
Sec. 307 (a)
Sec. 311 (b) (2) (A)
Clean Air Act
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classification systems used by the several agencies.
3.2 Unit Process Regulation
By virtue of proposed regulations affecting the chemical consti-
tuency of feedstock, products, and waste discharges, the Environmental
Protection Agency could effectively regulate processes. In 1977, EPA
received guidance concerning process or equipment standards under the
amended Clean Air Act. Congressional intent concerning such standards
was expressed as follows:
"The Committee recognizes that in some instances (such as con-
trol of emissions from petroleum liquid storage vessels or of
organic compounds of carcinogenic potential) it may not be
possible for the Administrator to promulgate and enforce a
performance standard. While the Committee intends that a
performance standard be promulgated whenever practicable, the
Committee does not intend to prevent the Administrator from
dealing with problems where this would be impracticable . . .
Moreover, the Committee expects the Administrator to include
numerical performance standards whenever technological advances,
improved measurement methods or other changed circumstances
made numerical standards practicable."
Under the Clean Air Act, a performance standard is a "Standard
for emissions of air pollutants which reflects the degree of emission
limitations achievable through the application of the best system of
emission reduction". The intent of the Statute is that the
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Environmental Protection Agency should determine the achievable
limits and let the manufacturer select the process. In one instance,
the Environmental Protection Agency did issue a process standard;
the standard applies to storage vessels for petroleum liquids. The
Agency indicated that only an equipment or process standard can be
applied when the source does not lend itself to emissions testing.
The Toxic Substances Control Act (Section 6a) requires the
Environmental Protection Agency to protect the public against unreason-
able risk of injury to health or the environment posed by a chemical
substance or mixture in a product and could also lead to process
standards or guidelines. The criteria used to define unreasonable
risk will help determine how this section will be used in regulating
chemicals and processes. For example, if unreasonable risk means a
substantial increase in mortality in the general population, this law
will be less widely applicable than if unreasonable risk is defined
as impairment of health in a susceptible part of the population.
Section 6b of the Toxic Substances Control Act states that the
Agency may order revisions in "quality control procedures" if adul-
teration of the chemical substance is occuring due to inadequate
process control. Stipulated improvements in quality control may
involve in-process or equipment changes. However, regulatory actions
under this section may be taken only for particular manufacturers or
processes and not manufacturers in general. Moreover, this law may
be used only to prevent unreasonable risk associated with adulteration
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of products and not risk associated with pollutant discharges.
Therefore, any use of 6b to impose pollution control must be effected
with the expressed intent for product decontamination controls.
Under Section 307 (a) of the 1977 Clean Water Act, rulemaking
activities to specify pollution control for some 131 water polluants
could conceivably involve specification of in-process modifications.
But current stalemating of this activity would preclude such an
innovative regulatory approach.
While regulatory authority to stipulate use of a given manufac-
turing process may not directly exist under any of these laws, a
manufacturer may not have many processing options in a situation
where a "toxic" chemical exists in a feedstock, a waste or product.
Therefore, the Environmental Protection Agency faces many issues
associated with regulating toxic chemicals, and needs to identify
those toxic chemicals which may occur in feedstocks, products and
waste discharges as the result of the basic process configuration.
There are thousands of processes in thousands of manufacturing
operations used in industry involving many thousands of chemical
products and effluents. Evaluation of the many processes for each
of the many potentially toxic materials on an operation-by-operation
basis, poses practically an impossible task. However, for the
organic chemical industries, there are some 41 unit processes which
comprise the bulk of manufacturing operations. These are listed in
Section 6 of this report (Tables 6-1 and 6-3).
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If the Unit processes used in a given industry segment or plant
are identified, and if typical toxic discharges and product contam-
inants for these unit processes are indicated, then there would be
an opportunity to focus regulatory activities.
The primary objective of the present effort is to identify
which unit processes are in use and to indicate likely toxic pollu-
tant discharges and product contaminants for each of these unit
processes. The first step is identification of the unit processes
in commercial use. This "Catalog of Organic Chemical Industry Unit
Processes" presents the results of this initial effort.
The next step will involve evaluation of each unit process from
the standpoint of toxic chemical occurence in feedstocks, products
and waste discharges. The approach will involve selection of three
to five high-volume representative manufacturing operations for each
of the unit processes. Analysis of results for each unit process
will lead to confirmation of commonality of toxic discharges and
product contamination or the absence of such. Following this
evaluation for air, water and solid discharges and for product con-
tamination, plant site visits and neetings with industry could be
used to verify the results and will facilitate a survey of available
discharge-treatment techniques. The characterization of toxic
materials in discharges and wastes along with the survey of available
treatment techniques will then lead to definition of needs for devel-
opment of new treatment techniques and process modifications.
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The end products of Che total effort will be:
• Evaluation/identification of toxic discharges and product
contaminants for each of 41 unit processes.
• Indication of research and development needs for each unit
process.
The first of these two primary products can be used for guide-
lines development and for subsequent enforcement of these regulations
by the Environmental Protection Agency regions. The data will serve
as a baseline for process pollution control needs identification and
will enable the focused enforcement of the Amended Clean Water Act,
the Toxic Substances Control Act, Resources Conservation Recovery
Act, and Clean Air Act provisions directed at specific toxic mater-
ials.
For example, for each unit process we will identify likely chem-
icals which might occur in waste waters, solid discharges and air
emission; and in some cases, as contaminants in products. Once the
chemicals are identified, the toxic risk can be assessed for the
modes of human and environmental exposures that could occur. If
toxic risks are considered significant, methods of risk abatement
must be considered. These risk abatement methods will include:
• pollution control technologies
• product modification
• feedstock quality control or switching
• changes in process conditions
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For each of these methods, the R & D needs that are prerequisite
to their implementation may be identified. Furthermore, through
this assessment, the media for which significant toxic risks com-
monly occur may be pinpointed for consideration in implementation
of the air, water, solid waste and product regulations.
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4.0 METHOD USED TO CREATE THE CATALOG
4.1 Overview
There were three steps involved in the creation of the Unit
Processes Catalog: (1) identification of the 263 selected commer-
cial chemicals synthetically produced in the U.S., (2) identification
of the unit processes used in the manufacturing routes for each of
the 263 selected chemicals, (3) identification of the commercially
owned and used manufacturing processes.
Many manufacturing synthesis routes involve more than one unit
process. For example, the manufacture of toluene diisocyanate,
starting with toluene involves three unit processes:
• Nitration (of toluene to dinitrotoluene)
• Hydrogenation (of dinitrotoluene to diaminotoluene)
• Phosgenation (of diaminotoluene to toluene diiso-
cyanate)
There are two reported commercial toluene "dlnitration processes,
one owned by Meissner and the other owned by Sumitomo. The
dinitrotoluene "hydrogenation" and the diaminotoluene "phosgena-
tion" processes are owned by Allied, FMC, Nippon Soda-Nissan,
Sumitomo.
This example illustrates that, for a given manufacturing syn-
thesis route there may be multiple unit processes, and for each
unit process multiple commercially owned and used manufacturing
processes. Accordingly, there are three entities involved in the
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creation of this catalog:
(1) Manufacturing synthesis routes; a list of the unit pro-
cesses used in the synthesis route (i.e., nitration,
hydrogenation and phosgenation unit processes used in
the manufacturing synthesis route from toluene to toluene
diisocyanate).
(2) Unit Processes: discrete, identifiable, individual chemi-
cal reactions used commercially in organic synthesis (i.e.,
nitration, hydrogenation and phosgenation).
(3) Manufacturing Processes; a list of the commercially owned
and/or licensed manufacturing processes used to carry out
the application of a unit process (i.e., Biazzi and
Meissner for toluene nitration).
4.2 Identification of the Principal Commercial Chemicals
The list of the 263 commercially significant chemicals was
started using the following lists:
• list of 131 chemicals on the EPA Recommended List of
Priority Pollutants, Pursuant to the Consent Decree
of December 5, 1977 and the Clean Water Act of 1977
Section 307(a)
• list of 88 chemicals surveyed and ranked for 1982
Projected Total Annual Gross Emissions from the Hydro-
science, Inc. Progress Report No. 7 for September 1-
September 30, 1977 on "Emissions Control Options for
the Synthetic Organic Chemicals Manufacturing Industry"
under EPA Contract No. 68-02-2577
• list o-f 59 organic chemicals being studi.ed by Environ-
mental Science and Engineering, Inc. under an EPA
contract aimed at evaluating carbon adsorption pollu-
tion control
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• classification of 16 Nitration-Products/Processes, from
"Air Pollution from Nitration Processes", by Processes
Research, Inc., under EPA contract No. CPA 70-1, March
31, 1972
• classification of 25 Chlorination/Hydrochlorination
Processes, from Air Pollution from Chlorination Pro-
cesses, by Processes Research, Inc., under EPA contract
No. CPA 70-1, March 31, 1972
• Products and Byproducts of Chemical Process Technology
available for license or sale from "Sources and Produc-
tion Economics of Chemical Products", Chemical
Engineering, McGraw-Hill Publications Co., 1974
These lists were combined by entering each chemical on a file
card with all primary synonyms entered thereon. Those chemicals and
sources which were not included in the "1977 SRI-Directory of U.S.
Chemical Producers", were eliminated from the file as non-commercial-
scale chemicals.
4.3 Identification of Unit Processes
For each of 263 selected commercially produced chemicals, the
manufacturing synthesis routes was identified through telephone sur-
vey and consultation and exhaustive search in the following sources:
• Lowenheim> F.A., Moran, M.M., "Faith, Keyes and Clark,
Industrial Chemicals", 4th edition, John Wiley & Sons
(New York) 1975.
• Groggins, P.H., "Unit Processes in Organic Synthesis",
4th edition McGraw-Hill (New York) 1952.
• Shreve, R.N., "Chemical Process Industries", 3rd edi-
tion, McGraw-Hill (New York) 1967.
• 1977 Petrochemical Handbook, Hydrocarbon Processing
56(11) November 1977.
• 1973 Petrochemical Handbook, Hydrocarbon Processing
52(11) November 1973.
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• Sources and Production Economics of Chemical Products,
McGraw-Hill (New York) 1974.
The main chemical reactions (i.e., nitration, hydrogenation and
phosgenation) in each manufacturing synthesis route were identified
and entered on the file card for each chemical. As the file grew,
some 22 unit processes were identified as widely used for large-vol-
ume manufacturing operations and were designated consistently as
"major unit processes". Likewise, some 19 minor processes (used in
small volume manufacture) were identified and used to characterize
manufacturing synthesis routes. In some instances, rather rigouous
definition of unit processes proved necessary to avoid undesireable
increase in the number of unit processes and multiple entry under
ambiguously defined unit processes. Section 6.4 provides the defin-
itions used as the basis for identification and listing of the unit
processes utilized to characterize each "manufacturing synthesis
route".
4.4 Identification of Manufacturing Processes
Simultaneous to the foregoing step, the owners and/or licensors
of some 658 manufacturing processes used to commercialize the unit
processes were identified using telephone survey and the source
references listed in the forgoing Section 4.2. The 145 owner/licen-
sor companies and their addresses are listed in Section 6.5 of this
report. Many of the commercially used manufacturing processes are
owned by foreign companies.
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5.0 STRUCTURE AND USES OF THE CATALOG
5.1 Major Unit Processes
Table 6.1 lists the 22 "major unit processes", the number of
compounds (total 416) and entries to the table (total 447) for each
process. Table 6.2 follows with the listing of the chemicals under
each process used in their manufacture.
These processes, designated as major, are used in the manufacture
of a number of different chemicals, in large volumes and in many
plants. The only exception is Steam Reforming - Water Gas Reaction
which yields methanol as the only major product. However, methanol
is made in fouteeen U.S, plants in tremendous volumes by this process
so it was included among the major processes.
The processes are listed alphabetically within the table and
the major product is listed alphabetically within each process. There
are six columns in the table, reading from left to right: Other
Required Processes, Product, Feedstock, Owner of Process, No. of
Licensed Commercial Plants and Total No. of U.S. Commercial Plants.
These headings will be described using entries from the first page on
alkylation. The first entry for acetic acid shows that the oxidation
process is involved as well as alkylation. The feedstock is n-butanes,
and the owner of a process available for license is Bayer AG. No
licensed commercial plants are in operation as shown by "N" in the
fifth column. The last column shows that there are ten commercial
plants operating in the U.S. These numbers are independent of the
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columns on "Owner of Process" and "No. of Licensed Commercial Plants."
These refer to worldwide licenses so the numbers may be considerably
higher than for U.S. plants.
Linear alkyl benzenes are made from two different feedstocks,
so are listed accordingly. Phenol and acetone are products from the
feedstocks benzene and propylene. The process is indexed under phenol
since that is usually the primary product. Here four processes are
involved, alkylation, oxidation, hydrolysis and acid cleavage. The
product is cross-indexed under each of these processes. If only one
process is required, as in alkylation of benzene with ethylene to
ethylbenzene, the word "None" is entered in Column I, Other Required
Processes.
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5.2 Minor Unit Processes
Table 6.3 lists the 19 "minor unit processes", the number of
compounds (total 42) and entries to the table (total 42) for each
process. Table 6.4 follows with the chemicals listed alphabetically
under each process used in their manufacture.
Most of these "minor unit processes" are used in the manufacture
of only a few chemicals and generally in relatively low volumes. They
may be one step in a sequence, such as Acid Cleavage for phenol-
acetone manufacture. Some are very specific, such as Nitrosation and
the Beckmann Rearrangement which are used in the manufacture of
caprolactam from cyclohexanol/cyclohexanone, ammonia and oleum.
One change in the table format was required from Table 6.2. The
first column is entitled "Processes". The word "None" is not used
here since it is not applicable. The name of the Minor Unit Process
is repeated as required. For example, Carboxylation is used for
salicylic acid and again for sodium p-aminosalicylate, because that
is the only process envolved. Acid Cleavage is not repeated for
the second phenol-acetone entry, but it is involved as one of the
four processes.
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5.3 Index of the Chemicals Produced by Unit Processes
In Table 6.5 we present an alphabetical listing of all the
chemicals from Tables 6.2 "Major Unit Processes" and 6.4 "Minor
Unit Processes;'" There are 263 commercial organic chemicals tabulated
in this index.
The table comprises four columns as follows: Product, Other
Products, Processes and Feedstock. Entries are made for each feed-
stock, but the product is only counted once. For example, No. 1,
Acetaldehyde, is listed twice, No. 2, Acetic acid, is listed six
times and No. 3, Acetic anhydride, is listed twice.
There are 387 product entries by feedstock for the 263 chemicals
in the index. For instance, the three chemicals listed above are
listed ten times for the ten processes involving different feed-
stocks in each of the three cases. As shown by Tables 6.1 and 6.3,
there are 447 entries to the table of major processes and 42 entries
to the table for minor processes for a total of 489 entries. This
higher total results from an entry being made to the table for each
of the processes used in manufacture of a chemical. For example,
phenol/acetone requires four processes, so is listed in turn under
these four, namely alkylation, oxidation, hydrolysis and acid
cleavage. Great care was taken to cross index all of these processes
for each product in Tables 6.2, 6.4 and 6.5.
24
-------
5.4 How to Use the Unit Processes Catalog
The original intent of the Unit Processes Catalog was to identify
the unit processes used to produce the 263 primary synthetic organic
chemicals, so that assessment of the toxic chemical pollutant dis-
charge and product contamination risks for these organic chemical
manufacturing operations can be focused on their fundamental processes.
Assessment of toxic chemical pollution discharge or product con-
tamination risk for a given manufacturing operation may start with
identification of the unit processes, the feedstocks and the number
of plants in operation. This catalog provides the key to identifica-
tion of the unit processes. Once the unit processes are identified,
our environmental assessment of pollution discharge and product risks
for each unit process may be applied to the assessment of the overall
manufacturing operation's risks. These assessments of pollution and
product contamination risks for the 41 unit processes are just
beginning at this writing, and will be forthcoming over the next
three years.
Other uses of the catalog appear to be likely. Opportunities
for development of gaps in process technology can be identified by
examination of the 41 primary organic chemical synthesis routes.
Moreover, in cases where a manufacturing plant is being planned,
a process engineer may use the catalog to select a sequence of unit
processes which are both economically and environmentally optimal.
If a process engineer wishes to know the state-of-the-art for
25
-------
manufacture of a given chemical, he may find the chemical product in
Table 6.5, which lists the unit processes used for each of 263
chemicals. Then he may identify the owners or licensors of existing
processes, the feedstocks used and in some cases the number of plants
in the U.S and abroad using Tables 6.2 and 6.4.
26
-------
6.0 UNIT PROCESS CATALOG
6.1 Major Unit Processes
Our Unit Process Catalog consists of five parts. The first
part concerns the 21 Major Unit Processes and consists of Tables 6.1
and 6.2 which follow. The structure and use of these tables is
described in Sections 5.1 and 5.4 of this report.
6.2 Minor Unit Processes
The second part of our Unit Process Catalog concerns the 19 Minor
Unit Processes and consists of Tables 6.3 and 6.4 which follow. The
structure and use of these tables is described in Sections 5.2 and 5.4.
6.3 Index of Chemicals Produced by Unit Processes
The third part of our Unit Process Catalog consists of Table
6.5 which is an alphabetical listing of the 263 chemicals under
consideration. The structure and use of the table is further
described in Sections 5.3 and 5.4.
6.4 Definitions of Unit Processes
6.4.1 .Major Unit Processes
on
-------
Table 6.1 Major Unit Processes - Summary
Process Compounds Entries to Table
1. Alkylation 15 15
2. Amination by Ammonolysis 11 12
3. Ammoxidation 10 10
4. Carbonylation (0X0) 10 8
5. Condensation 51 52
6. Cracking (Catalytic) 7 17
7. Dehydration 18 19
8. Dehydrogenation 15 20
9. Dehydrohalogenation 6 7
10. Esterification 24 24
11. Halogenation 54 60
12. Hydrogenation 26 26
13. Hydrohalogenation 7 7
14. Hydrolysis (Hydration) 27 30
15. Nitration 12 12
16. Oxidation 47 45
y
17. Oxhalogenation 5 7
A
18. Phosgenation 3 3
19. Polymerization 34 38
20. Pyrolysis 22 20
21. Re forming (S t earn)-
Water Gas Reaction 1 6
22. Sulfonation 11 9
TOTAL 416 447
28
-------
tsi
VO
Ollllig
HEQUIHU>
PROCESSES
Oxidation
None
None
Table 6.2
PHODUCT
Acetic acid
Alkyl Benzenes (branched)
Alky) l)enzenei (Linear)
Uehydrogenalion Alkyl Ueiuenes (Linear)
None
None
None
None
Benzene. Xylenes
p-ferf-Buiylphenol
Cumene
tlhylbciueue
MAJOR UNIT PROCESStS-AUKYLATION
I ttOSTOCK
H-Bulcnet
Benzene
Piopyleue telrarnei
Benzene
Uncar olefini
Benzene
Unear paraffins
Toluene
Phenol
Isohulcne
il«nzene
Propyleno
Benzene
lilliylene
Dehydro-
ludogcnation
llydrogenalion
None
None
Acid cleavage
Hydrolysis
Oxidation
Oxidation
N-lsopropylV-p
Lead alkyls
p-Nonyl phenol
Phenol, Acetone
Pyrorncllilic dian
N-lsopropyl-N'-Dlienyl-p-phenylenediarnine> /j-Chloronilrobenzene
Aniline
Acetone
Blhyl chloride (alkyl chlorides)
Phenol, Propylene liimer
Benzene
Propylene
Je 1,2,4-TrirneUiylbenzenc
(Psuedocumcne)
OWNIIH OF PKOCKSS
Bayer AC
Chevron Research
Conoco Chemicals
Texaco Development Coip.
Phillips Petroleum Co.
UOP Process Div.
Conoco ChcinicaU
Phillips Petroleum Co.
UOP Process Div.
UOP Process Uiv.
Hills
UOP Process Div./Tofiiy Ind. Inc.
lluls
1 tub
Union Carbide
UOP Process Division
Instilul Hruncais du Petrole
lluls
Royal Dutch Shell
Union Caibide
UOP Process Oiv.
Suniilomo Chem. Co.
_
lluls
Allied Chemical
NO. 01
LICKNStll
COMUI-RCIAL
PLANTS'
N
6
2
2
4
>S
2
1
U
4
1
1
1
1
2
U
N
1
U
• 14
U
1
—
1
U
TOTAL
NO. Ol- U.S.
COMMI£KCIAL
PLANTS'
(10)
0)
-
-
-
(1)
-
—
(1)
-
(47)
(S)
(13)
-
(17)
-
—
-
(3)
(6)
(13)
(10)
(2)
1U - Al feiul unc pliinl cxUu, bui luiul U unkauwo.
N - Nu coinnufcUl plimli.
3 fateatttcse* uulfciiie fatal number of U.S. pruditciuf plaali tc$*tttica at' ptutxa.
^Hcduciivc aDtybliou
-------
MAJOK UNIT PROCESSCS-ALKYLATION (Cunlinued)
NO. Ol; TOTAL
OTHER LICENSED NO.OI-U.S
HEQUIUEU COMUKMC1AL OOUMIJKCIAI
PROCESSES ntouucr I:EI-:USTOCK OWNER OF PROCESS PLANTS' PLANTS*
Ikhydrogeaullim Slyrene Benzene Badger (Union Caibide-Coideu) >20 (13)
miiyleue Cdl-'-Chcinie-Tcchnip 7
Munsaiilo 10 -
Scientific Design 3
Sliell U
None 2.4-Xyleuul p-Cicsul - - (S)
Melhyl CliluriJe
1 U- Al tcaxl uoo |4iuil CMixU, bill foul Is uiikauwo.
N-No ctMnawitlai ylttutl.
i itulkdi: lalnl nauibci of U.S. piuducin| pUaU icginlkn of piaccu.
U)
O
-------
MAJOR UNIT PROCESS-AMISATION UY AMMONOLYSIS
OllltH
REQ.UIKED
PROCESSES
None
None
Condensation
llydrocldorlnallon
None
None
None
None
None
None
None
None
Dehydration
fRouucr
Aniline
Benzene sullonaniide
Clioline cliluridc
p-Chlorobenttiie sulfonamidc
Dunelliylibfinmnide
Elhanolmninei
Elhylamines
Eiliylcnedianiinc
Eiliylcncdiamine
I lexainelhyleiicdiaminc
Mcihylamines
Uiea
I ttl> STOCKS
Phenol
Ueiucne uilfonyl chloride
Elhylenc oxide
Trimeihyluminc
p-Chlorobcruenc sulfonyl chloride
Dimeihylamine
Mclhyll'orniale
OWNER 01 i
llalconlnl.
Diamond Shamrock Corp.
UCB
Diamond Slumrock Corp.
UCB
NO 01-
LICENSED
COUMIiRCIAL COMMERCIAL
1-LARfS' PLANTS*
TOTAL NO.
01 U.S.
I
u
I
PLANTS1
(7)
(2)
(3)
Ulliylene oxide
Bllunol
Elhylene dicliloiide
Monocllianolamine
Adipic Acid
Mellianol
Caibon dioxide
Iliili
Milsui Toaltu
Scientific Design
Shell Development Co.
CuirChemiohCo.
Leonard Process Co.
-
Leonard Process Co.
Ziinmer/lieaunil
Leonard Process Co.
C & 1 Girdlei
Milsui Toalso
Montedison S.p.A.
Slamicarbon
Marrovic/Teclmip
1
LI
2
4
N
4
3
N
1
19
U
U
45
103
1
(S)
_
(S)
-
(3)
-
(6)
(6)
(49)
-
—
-
1 U- Al Icul oilc plinl cibll. but lolal It unknown.
N No uiuliueicul pliull.
Pitivnllicwi liulkuie lulal nuutbci of U.S. producing pbnu i
is of process.
-------
MAJOH UNIT PROCESS-AMMOXIDATION
OJ
K)
OTIII;K
REQUIHtlD
FROCUSSKS
None
None
Iliilogenalian
llyuVogeiulion
None
llydrogenaiion
None
Nune
None
Condensation
None
fKODULT
Acrylonilfile
Adiponiirile
AdipouiliUe
liexamelhylene Jiiuuine
Ucnzanilrile
llexawelhylene diiimine
Hydrogen Cyanide
Isoplithaloniuile
PhlhaloniKile
fyridine. fte/n-Picoline
Tcrcnhlhalonilrili.'
1-ttU STOCKS
Hiopylene
Adipic Acid
Uuladiene
Toluene
Adipic acid
Anuuonia
Mellune
m-Xylene
o-Xylene
Acetaldeliyde
Fofiiiiildeliyde
Mcllunol
/>-Xylene
OWNKH 01- rROCIiSS
UP Chemicab lulernalional Lid.
Muutediioi) S.p.A./DOl'J'focca Uivbion
SNAM Piogelli
Slandaid Oil of Ohio/BjJgci Co.
Monletibre S.p.A.
Cut Cliemical/Uadgci Co.
Ziiniiicr/IU Puso-Ueaunil
U. F. Goodricli
Montedison S.p.A. '
Ziiner AC
Milaibiilii Gas Cbemial/Badgei Co.
Mitsubishi Gai Cheinical/Uadger Co.
UP Chemicals International Ltd.
Mitsubishi Gas Chemical/Uadger Co.
NO 0|.'
I.ICKNSEU
COMMERCIAL
PLANTS'
3
2
1
>4S
3
N
1
1
1
1
2
N
N
TOTAL NO.
Ol: U.S.
CGUMKKCIAL
PLANTS1
(5)
-
-
-
(7)
(1)
(6)
(ID
_
-
(0
(0)
(2)
(0)
*U-AI fciul uuc fital c»uu. but lolid u unknuwa.
N - No toaiun.'itiil pbiili.
fueiillu:>c> Uidtailc lubl auiubci ol U.S. |iia>luciii|i pUnu rc^iidlcu u( (iiottu.
-------
CO
LO
OTIII'H
KixniikUi
PKOi:i-SSI:S
None
None
llydrogenalion
None
llydrogenalion
Hydrolysis
Condensation
Hydrolysis
llydrogenaliou
PHOUUCT
Acetic Acid
Alcohol,^,,)
u-Bulanol
n-Bulyraldehyde
Klhyl acrylale
2 Ethyl hexanol
u-ttulyl alcohol
Isobulyl alcohol
Isobulyraldehyde
Formic acid
Sodium formate
Formic acid
Isobulyl alcohol
l-t-KUSTOTK
Mellunol
Carbon monoxide
Olefuis
Carbon monoxide
Propylene
Cai bon monoxide
Acetylene, Elhanol
Carbon monoxide
Propylene
Carbon monoxide
Carbon monoxide
Sodium hydroxide
Carbon monoxide
(Mclhauul recycled)
Propylene
Caibon monoxide
MAJOR UNITPROCESS-CARIIONYLATION (OXO)
OWNliK Ol' PKOCIiSS
BASF AC
GiilfOU Chemical* Co.
BASF AC
BASF AG
Kuhrchcmic/FWII Faibwerke llocchsl
Rulucliemie AG and
Ruhrchemie AG/Klione Progil SA
Monsaiilo
Siauffcr Chemical Co.
Leonard Process Co.. Inc.
NO. 01
LICENSI-U
COMMERCIAL
PLANTS'
I
7
IS
0
12
I
N
TOTAL NO.
OF U.S.
PLANTS
(10)
(7)
(S)
(5)
(2)
* U- At ka*l ooe plaal cxbu, but luful U uukouwa.
N- No cuiiuuufcLiI plants.
frrcalhcfct tiulicale loul number of U.S. pioduciug |4aDU rugaiUlcu of pruccu.
-------
MAJOR UNIT PROCESS-CONDENSATION
OTHER
REQUIRED
PROCESSES
Pyrolysii
Dehydrogenallon
None
Aininalion by ammonolycis.
Hydrohalogenalion
Dehydration
1 lydroge nation
Halogenalion
Halogenalion
Dehydrohalogenalion
None
None
None
Hydrogenaliou
I'hosgenalion
None
None
None
PRODUCT
Acetic anhydride
Benzene sulfonyl cldoride
Biphenyl (dipheuyl)
Bisphenol A
Cholinechloiide
Crotonaldehyde, n-Uulyl alcohol,
u-Bulyraldehyde
Dichlorodiphenylliichloro ethane
1 1 , 1 ,1 -lrkhloro-2.2-bis (jxliloio-
phenyl) ethane) (DDT)
2,4-Dichlorophenoxyacelic
acid (2.4 D)
2-(2.4-Dii;hiorophenoxy) propionic acid(2,4-DP)
4,4'-Dichlorophenyliiullone
Dipiiciiyiariiirie
Diphenylguanidine
N,N'-Di|)henylliydrazine(hydrazobenzene)
Dipheiiylmeihane-4.4'-diuiocyanaie
|(Mclhyl«ne bis(4-phenyl isouyanale)l(MDI)
Elhyl acetale
Elhylene carbonate
Elhylene glycol monoelhyl ether
KEEDSTOCK
Acetic acid
Benzene
Chlorosulfonic acid
Benzene
Acetone
Phenol
Elhylene oxide
Trimelhylamine
Acelaldehyde
Acelaldehyde
Monochloro benzene
Monochloroacelic acid
Phenol
a-Chloropropionic acid
2.4-Diculorophcnol
Monoculorobenzeue
Sulfur Irioxide
Aniline
Aniline
Cyanic acid
Nitrobenzene
Aniline
Formaldehyde
Phosgene
Acelaldehyde
Elhylene oxide
Carbon dioxide
Elhylene oxide
(•llunul
OWNER Of PROCESS
Wacker-Chemie
Diamond Shamrock Corp.
Nippon Sleel
Honshu
Hooker Chemical Corp.
Montanlo
Union Carbide
Rhone Progil
UCB
BP Chemicals International Lid.
Kyowa llakko
Diamond Shamrock Corp.
Diamond Shamrock Corp.
Milsui Chemical
Diamond Shamrock Corp.
Honshu
(Jniroyal
Sumitomo Chemical Co.
llodogaya Chemical Co.
Mills
Wacher-Chemie
Huts
lluls
Shell Development Co.
NO. 01 TOTAL NO.
LICENSED Ol- U.S.
COMMERCIAL COMMERCIAL
PLANTS! PLANTS'
12*
U
U
U
2
2
1
'
U
1
U
U
U
(1)
U
U
1
U
1
s
2
1
U
3
(8)
(6)
_
-
(6)
(2)
(D
(II)
„
(3)
(I)
(D
(4)
(M)
(I)
(7)
1 U - AI Itiml one pbnl exult, tml luul is unknuwu.
N - Nu commcfcUi PUuit.
*hicnibcM* indicate number uf U.S. iifoJuctiig |ilanlt r
of f
-------
MAJOR UNIT PROCESSES-CONDENSATION (Continual)
OTIIIiH
RI-XHIIKtO
NO. 01-' TOTAL NO.
LICENSED OK U.S.
COUUCRCIM. CUMUIikCIAL
PROCESSES
llydiogeualion
lluloge nation
Carbanylalioa
Hydrolysis
None
Dehydration
None
Nune
Jj{ Dehydration
Dehydration
1 tydrolialogeuallon
Pyrolysii
(.'(licking
Alkylalion
Dehydr oh aloge nation
llydrogenalion
I'yrulysis
Pyrolysis
Dehydration
PRODUCT
i Elliylhexanol
Clliyl paralliion(Paralliion)
Poimic acid
llcptenet
llexaniclhylene lelraiuiaet
Isuphoione
Itoptene (2 Melliyl 1 ,3-buUdicuc)
luiptenc (2 Mclliyl 1 ,3-buladiene)
liuprcnc (2-Mclhyl-l ,3-buladiene)
Isopieiw (2 Mclliyl 1 ,3-buladiene)
Isoprene (2 Melhyl-l ,3-buladicne)
N-lwipropyl-N'-phenyl-/>-pheiiylencdiinniiie
Mclamine
Melainine
Mciilylonide
I'EliUSTOCK
Acelaldehyde
Bulyialdehyde
O.O-Diinelliyl pliosphoro-
IliiouuclUoiidale
Sodium niliopticnoxide
Caibon Monoxide
(Mclluiiiil recycled)
Butylcnei
Pmpylene
Anunonu
PoiinalJchyde
Acetone
I'copyUuc
Acetone
Acetylene
Ftunuldeliyde
Isobulylcne
l:orituildeltyde
Hydrogen chloiiJc
liobulylcne
Isobulylcne
Mclhanol
Acetone
Aniline
^•Cldoionilrobenzene
Uicyandumide
HIM
Acetone
OWNER Ol- HROCtSS
Kyowa llakko
Rlione Progil
Mull
Kyowa lUkko
Kuhrcheiuie/Klione Piogil
Slauffei Chcin. Co.
Leonard Process Co., Inc.
tnilitul Fiancan du Petiole
UOP Process Urvuion
Hooker
Meuona
Veba-Cliemie AC
Scieiuific Design
SNAM Piogelli
Inslilul Fiancais du Pelrole
Uayci
Maialhon Oil
Inslitul Ficincais du Pelrole
Licensinlorg(USSK)
Suiniloino Cbeuiiciil Co.
Pioduils Azole
Montedison S.p.A.
Nissan Chemical Industries
111' Chemicals Inleriialional tld.
Texaco Development Corp.
PLANTS'
1
1
2 .
1
IS
2
N
N
12
U
U
U
2
1
1
N
N
1
2
1
U
3
1
3
U
PLANT
(5)
-
-
-
(2)
—
_
(2)
-
(«)
-
(2)
(6)
-
-
. _
-
-
(3)
(3)
-
(4)
_
*IJ A| fcjsi one |>btui cxisii, but luul U unknuwa.
N -No cuiiiiucfcUl Pfcinls.
1t*ufcollickCB jntlicJlo auiubci u| U.S. pfutliiciiig pliinli tc&udlci* ol piiurcu.
-------
MAJOR UNIT PROCESSES-CONDENSATION (Cunlinuetl)
OTHER
REQUIRED
PROCESSES
llydrugenalion
llydrogenalion
None
llalogenalion
Dehydrolialogenalion
Dehydration
Dehydration
llydrogenalion
llalogciialion
None
Pyrolysis
Cannizzaro Reaction
Dchydiogeualion
Polymerization
None
None
PRODUCT
DL-Melhioiiine
2-M«lhyl-2-bulanol
(r«if-Amyl alcohol)
2-Melhyl-3-bulyu-2-ol
2-MtflhyM-chloropheuoxy-
acelicacid(MCPA)
2 ( > Mclliyl-4-chloioulienoxy) propionic aciil/MCPP)
2-Melhyl-S-elhylpyridiiie (MCP) '
(S-elhyl-2-picoline)
Methyl isobulyl kelone
Methyl parathion (0,0-dimelhyl 0-/>-nilro-
phenyl phosphorolhioale)
4-Melhyl- 1 -penlene
Oxalic acid
Peniaeiylhrilol
/(-Phenylphenol
Polyethylene lerephlhalale
tou-Propiolaclone
Propylene carbonate
FEEDSTOCK
Acrolein
Cyanic acid
Melliyl mercaplan
Acetone
Acetylene
Acetone
Acetylene
o-Crcsol
Monochloroacelic acid
a-Chloropropionio acid
4-Chloro-o-crcsol
Acelaldehyde
Ammoniii
Acetone
Hydrogen
0,0-l)imelhyl phosphoro-
Ihionochloridale
Sodium p-nilrophenoxide
Propylene
Sodium rormale
Acelaldehyde
Formaldehyde
benzene
Cyclohexanone
Dimethyl lerephlhalale
Elhylene glycol
Formaldehyde
Kelene
Carbon dioxide
Propylene oxide
OWNER Ol- PROCESS
Suuiiloino Chemical Co.
SNAM Progelli
SNAM Progelli
Mitsui Chemical
laukro
Montedison S.p.A.
UP Chemicals International Ltd.
Texaco Development Corp.
Slauffcr Chemical Co.
UP Chemicals International Ud.
Slaufl'cr Chemical Co.
Monlediion S.p.A.
Meissiiet
Union Carbide
Imperial Chemical Industries
HoechM
liivenla-bm>
Zimmer AG
Ucaimil Corp.
U.F. (joodrich
Hills
nu. ui*
LICENSED
COMMERCIAL 1
PLANTS'
'
U
1
U
u
1
3
2
'
U
1
1
U
N
II
U
4
26
U
2
2
iui AI. n
Ol U.S.
L-OMMERCI
PLANTS
(2)
(2)
(1)
(2)
(4)
(2)
S
(4)
(1)
(7)
(4)
(1)
(21)
(0)
(1)
11* Ai ttiiial one plant cxiiU. but luul u unknown.
N Nu fommettul Ptinls.
3raiculhtiMk hidkalc nuntbci oi U.S. |»iLHltu;iiiu (tbuti t
-------
MAJOR UNIT PROCESSES-CONDENSATION (Continued)
NO. OP NO. OF
OTHhR LICENSED ' LICENSED
REQUIRED COMMERCIAL COMMERCIAL
PROCESSES MOUUCT FEEDSTOCK OWNER OF PROCESS PLANTS' PLANTS*
Ammoxidation Pyridinc, 6e/a-Piculino Acelaldcliy Je UP Chemicals international Ud. N (2)
Formaldehyde
Mellianol
Oxldallou TeliahyJioluiiin, 2.3,4.5-lelratiirbo)iylic Fuian GclsciibcigClieinieGmbll N (2)
. JuiJiydiide Maleic aiiliydiide
Oxidation Tcliaiiiclhyllhiurgin iliuilfide (Tliiram) Ammonia. Carbon diailfide UCB I (S)
(Bis (ilimelhyllhioaiibumoyl) disulfUlc) Dinielliykimine. Hydrogen peroxide
llalogenalion 2.4.S-T«iclilorophenoxy acclic acid (2.4.S-T) Acclicacid Diamond Shamrock Corp. U (8)
Triclilorophenot
Deliydration Zincb (Zinc elhyltne bisdilhiocarbaiiiale) Ainiuonia UCB I (4)
Caibon disulfide
lilhylene diaiuine
Oehydralion Zuain(Ziiic diinelliylJilliiocacbanulc) Ammonia UCB I (9)
, Carbon diiiilfido
Oimelliylaiiiine
CO
(U-- At kail aiw |)laul chiaU. bul loul U uukauwn.
N -No coiamefctil HaQli.
2 hiienthesci imliciile number uf U.S. pruduciag plauts leuai Jlcu ut vtucc**.
-------
MAJOR UNIT PROCESS-CRACKING. CATALYTIC
LU
00
OTHER
REQUIRED
PROCESSES
None
None
None
None
PRODUCT
Acetylene
Acetylene
Acetylene
Isobulylene (Uobuteiie)
It t OSTOC K
Melliane and by-product elhylcue
Methane
Natural gas
Isobulane
None
Nune
Condensation
Hal ogc nation
llaloge nation
Italoge nation
Oxylialogenalion
None
llaloge nation
Oxyhalogenalion
Isoprcne
Isopreue
Isoprene
Pcrchloroelhylene and
Tricliloioelhylene
Perchloroethylene and
Trichlofoelliylcne
Perchloroelhylene and
Tficliloioelhylene
Vinyl chloride monomer (VCM)
Hydrogen chloride
Vinyl chloride monomer (VCM)
Propytene
Amyleuet
Isobulylcne
Formaldehyde
Elhylene dichloride
Acetylene
AnyC] chlorocarbon mix lure
tlliylene dichloride
lilhylene
Dehydrohaloge nation
llalogenaliou
Oxyhalogenalion
Vinyl chloride monomer (VCM) Ethane
OWNER Ol PROCESS
Union Carbide
BASF AC
Suciele Uelge dc I'Azole
Coastal Slalet Petroleum Co.-Foilei Wheeler
lloudry Div. Air Prod, t Cliem.
Pl.illips Petroleum Co.
Total Compagnic Krancaise de Kaffinage
I (OP Process Div.
Scientific Design
Shell
Instilul Francais du Pelrole
Licenstarg(USSK)
Diamond Shamrock Corp.
Rhone Progil
Scientific Design
Wacker-Chcmie
PPG Ind.
Waclterlhemie
Farbweike lloeclul
Rhone Progil
Montedison S.p.A.
Monsanlo/Scienlific Design
Klione Progil
Staufler Chemical Co.
Union Carbide
Transcal/Luiiimus Co.
NO. Of
LICENSED
COMMERCIAL
PLANTS'
3
11
U
|
U
2
3
N
11
2
1
2
U
1
S
3
U
U
28
2
1
6
2
22
1
TOTAL NO.
or u.s.
COMMERCIAL
PLANTS'
(2)
(3)
(0
(0
-
-
_
-
-
-
-
-
(ID
—
-
-
-
(ID
-
-
_
_
-
-
-
1 U Al Icasi ooc pbnl enUls. tut luUl b uukimwp.
N- No cuiuiuer^LiI pliiiiii.
1 PjfcAllwics uulicatti ouutbci ul U.S. piutlucing pbnls f
t ul* prucc
-------
MAJOR UNIT PROCESS-CRACKING. CATALYTIC (Continued)
NO. 01-' TOTAL NO.
ucENStu or o.s.
REQUIIttU COMMERCIAL COMMERCIAL
PHOCIiSSES PRODUCT l-'KliUSrOCK . OWNKH Ol-CKOCtSS PLANTS! PLANT'S1
lUlogeiulion Vinyl chloride monomer (VCM) Acelylcne Monocliem. Inc. - (I)
Iblogenalion Vinyl diluiJo iiiononier (VCM) Eihylene - - <2)
Dehydrolmlogeruliun Vinyl dilotide monumer (VCM) Naplillia Kurelia-Cbiyoda 3 -
llulogciulion Nippon Zeon Co. LlJ. I -
Oxylutlogeiuilion
Iblogcnalion Vinyl clilotiJe nionoiuci (VCM) Elliyknc U. F. GooJiicli Chemkal Co.* 26
Oxyliakigeuation
1U- Al bail one (itial eniili. but lulal l> uukiiuwa.
N-Nu commeictil |>tiali.
Hiiicallwici iudicMle luliil auiubci ul' U.S. piotluclng pUnli icyiiiUcH uf |it4iccu.
Tliu piuccu luci Tbei mid
-------
MAJOR UNIT PROCESS-nEIIYIMATION
OTIII-R
PROCIiSSKS
None
Condensation
llydrogenalion
None
None
None
Condensation
Condensation
Condensation
Oxidation
Oxidation
Oxidation
Condensation
Condensation
Condensation
llydrogenation
None
None
PRODUCT
Atsauilio acid (p-aminobcuzenearsontc acid)
Criilonaldehyde, H-Bulyraldehyde
ii-Bulyl alcohol
lilhylcne
Elhylenc glycol ethers
Ethyl ether (dielhyl ether)
llcxanielhyleue lelramine
Isopren,
Isoprene
Maleic anhydride
Maleic anhydride
Muleic anhydride
Mesilyl oxide (isopropylidene acelone)
2-Melhyl-S-elhylpyridiiie (MEP)
(S-Elhyl-2-picoline)
Methyl isohulyl kelone
Morpholine
N riienyl 2-nanliihylainine
IblibSTOCK
Aniline
Arsenic acid
Acclaldchyde
lilhyl alcohol
Alkyl alcohols
Etliylcne glycol
Ethyl alcohol
Ammonia
Formaldehyde
Acelone
Acetylene
Formaldehyde
Isouulylene
Butadiene (* other
C4 hydrocarbons)
Benzene
Bulcne-l , Uutene-2,
Butadiene (if present)
Acelone
Acelaldehyde
Ammonia
Acelone
Dielhanolaniine
Aniline
2-Naphlhol
OWNER Ol- PROCESS
Sliciwin-Williams
BP Chemicals International, Ltd.
Kyowa llaldio
Air Reduction Co.
Shell Development Co.
-
Hooker
Meissner
SNAM Progelli
l.icensinlorg
BASF AG
Alsuisse • IJCB
Rhone Piugil
Scientific Design
Veba-Chcmie AG/Bayer
Bayer AG - Lurgi Corp.
BP Chemicals International. Ltd.
Texaco Development Corp.
Montedison S.p.A.
BP Chemicals International, Ltd.
Texaco Development Corp.
Mills
Sumitomo Chemical Co.
NO. OF
LICENSED
COMMERCIAL
PLANTS'
N
U
1
2
3
-
U
1
2
2
3
1
26
4
1
3
U
1
3
U
1
1
TOTAL NO.
01 U.S.
COMMERCIAL
PLANTS'
(3)
(2)
-
(6)
(8)
<6)
-
(10)
-
-
(5)
(2)
(5)
(1)
(1)
* U- Ai loui one exult, bul lot J U unttnuwa.
N~Nui cimuiicicbtl.
2f
-------
MAJOR UNIT PROCESS-DEHYDRATION (Continued)
OTIII-:K
REQUIKUD
PROCtSSL-S
Aininalion
fHOUUl.T FKI-USTOCK
Ammonia
Carbon dioxide
Condensation Ziiieb (Zinc elbylcne bls-dilliiocaibumate) Ammonia
Carbon disulluie
Elhylene duminc
Condeiuallon Ziram (Zinc dimethyl dilhiocarbamale) Ammonia
Carbon disulfide
Oimelhylamiiie
U
N-Nol
uao exblk. but lulal b unkuuwii.
OWN1-H OF rKOCt^S
C&TGirdlci
MaviovtcTcduiip
Mitsui Toalui Clicniicalj. Inc.
Montedison S.H.A.
SNAM Progetli
Slamicaibon
UCD
UCB
NO. OF
UCtiNSbU
COUMEKCIAL
PLANl^1
U
1
61
• 45
10
ISO
1
i TOTAL NO.
OF U.S.
COUMEkCIAI.
PLANTS'
(49)
-
_
—
-
(4)
.
2fticiilbeftes luilkale luiul uuiubci ul' U.S. pciMjucini pluils i
t of piu
-------
MAJOR UNIT FROCESS-DEIIYDROCENATION
OTHER
REQUIRED
PROCESSES
None
None
Alkylaliou
Condensation
None'
None1
None4
None
None
None
None
Hydrolysis
None
Oxidation
Condensation
None
None
Alkylalion
PRODUCT
AcclaUiehyde
Acetone
Alkyl benzenes, linear
Biphenyl (diphcnyl)
Butadiene
Butadiene
Butadiene
Cyclohexanone
a-lsoamylene (3-Melhyl-l-bulene)
Isoprene (2-Melhyl-l ,3-buladiene)
Isoprene (2-Melhyl-l,3-buladiene)
Methyl ethyl kelone
Methyl ethyl kelone
Phenol
fM'henylphenol(4-hydroxydiplienyi)
Piperylene (1,3-penladiene)
Propylene
Slyreue
FEEDSTOCK
Ethyl alcohol
Isopropyl alcohol
Benzene
Linear paraffins
Benzene
H-Bulaue
Butene-l
Buleuc-2
Bulene-l
Bulehe-2
Cyclohexanol
Cyclohcxane mixtures
Isopenlane
Isopenlane
Tertiary umylenes
Bulenc-l
Bulene-2
jtt'-Uulyl alcohol
Cycloliexane
Benzene
Cyclohexanone
M-Penlcne
Propane
Benzene
lilhylcne
OWNER OF PROCESS
BP Chemicals International Ltd.
Vcba-Chemic AC
BP Chemicals International Ud.
Deutsche Texaco AC
UOP Process Division
1 liiis
Nippon Si eel Chemical
lloudry Div. Air Products 4 Chem.
Phillips Petroleum Co.
lloudiy Div. Air Products & Chcm.
Phillips Petroleum Co.
BP Chemicals International Ltd.
Zinimer AC
Institute Francaisdu Pelrole
lloudry Div., Air Prod. & Chcm.
lloudry Div., Air Prod. & Chem.
Shell Development Co.
Texaco Development Corp.
BP Chemicals International Ltd.
Scientific Design Matimn Oil
Scientific Design
Institute Francais du Pelrole
Union Carbide
lloudry Div., Air Prod. & Chem.
lloudry Div., Air Prod. & Chem.
UOP Process Div.
Badger (Union Carbide and Cosdcn)
Cdl;-Cheniic/Technip
Monsanto
Shell Development Co.
Scientific Design
NO. OF
LICENSED
COMMERCIAL
PLANTS'
1 4
2
3
2
4
1
U
14
U
3
U
N
4
N
U
U
4
U
I
N
N
U
U
N
>20
7
10
U
3
TOTAL NO.
OF U.S.
COMMERCIAL
PLANTS'
(2)
(7)
(3)
(8)
(2,
(2)
-
(1)
-
(1)
(7)
4
(17)
(0
(2)
(61)
(13)
—
* U- Al tcasl one ptwil tixttli, but total U unknown.
N- No cuutmcicUl pliiuU.
2 Piutmltiestts iiidiciiie total ouiubci of U.S. piotiuciug planH legardJeu of pioccu.
i'jliily
4Oxiititivc
-------
MAJOR UNIT PROCESS-DEIIYDROCENATION (Cunlinuetl)
OTHER
PROCESSES
None
None
Slyrcuc
Xyleuci, mixed
1 U - Al Iciul uoo plant culila. but lulal b uuknown.
N— No couitucfcial u
Elliylbeiuene
NapliUia
OWNER 01- PHOCESS
Oadgcr (Union Carbide and Cosden)
Hub
Monsanto
Scientific Design
Shell Development Co.
HOP Process Div.
lloudry Div., Ail Products & Cheni.
NO. 01 TOTAL NO.
LICENSED Or U.S.
CaUMEKCIAL COMMERCIAL
PLANTS' FLANTS1
16
2
2 _
3
U
U
U (29)
nlltcaei inilkalo lulid uuuibcr uf U.S. pioducinc plants icguidlcu of proccu.
-------
MAJOK UNIT PROCESS-DEIIYDROIIALOCENATION
OTIIEK
RD)UIRI-D
PROCIiSSliS
Condensation
Alkylalioii
Condensation
llydrogenalion
Condensation
hio&g<: nation
Polymerization
Clacking (catalytic)
llalogciuliou
Oxyhulogenalion
Cracking (calalylic)
llalogcnation
Oxyhalogenalion
None
PKOUIILT FlitUSTOCK
2-(2.4 Dichlcwoplienoxy) piopionic acid (2.4-W)
N-lsuptupyl-N'-plicnyl-p-pheuyknediainiue
2^2-MclliylH-clil»(oplicuuity)pfU|iiuiiic acid (MCPP)
Culycarbouale resins
Vinyl chloride monomer (VCM)
Vinyl chloride monomer (VCM)
Vinylidene Chloride (1,1 -dichluroelhyleue) 1,2-Uichloroelhaue
OWNtH OH WOCESS
NO. 01- TOTAL NO.
UCEHSKD Ot- U.S.
COMMERCIAL COMMERCIAL
PLANTS' PLANTS1
o-Cliloropropionic acid
1 ,4-Dichloropheuol
Acetone
Aniline
/>-€lilaionilrobeiiuiie
a-Chloroptopioiiio acid
4-Clilorocresul
UUphenol A
Melhylcne chloride
I'hosgene
lilhane
Naphtha
Lankro
Sumitomo Chemical Co.
Lankro
Idemtsu Kosan
Transcal/Lummus Co.
Kureha-Chiyoda
Nippon Zeou Co. I.I J.
U
1
U
1
—
3
1
(2)
(3)
H)
(3)
(I)
-
'u~Al Iciut 0110 plMit cJkUu, bul lulul U unknown.
N-No tominciciid piiuli.
ii UidicuU (ulitl nuuibci u|' U.S. (iioiluciiig plunli i
(3)
of pi
-------
MAJOlt UNIT HROCESS-ESTERIFICATION
01
OTIItK
KKQUIkEU
PROCESSES
pttouucr
IttUSTOTK
Oxidation
None
None
None
None
None
None
None
None
Oxidation
None
None
None
Acrylic acid and Acrylale Kslers
H-Bulyl acetate
n-Uulyl benzyl phlhalale
Di-n-butyl phlhalale
Dielhyl phlhalale
Dihcplyl phlhalale
Diisodecyl phlhalale
Dimethyl phlhalale
Dimethyl lercphlhalate
Dimethyl Icrephlhalale
Di-n-oclyl phlhalale
Dioclyl phlhlale (2-clhylhcxyl phlhalale)
Ethyl acelale
Propylene
Alcohols
Acetic acid
ii-Uulyl alcohol
Ueruyl alcoliol
/i-Uulyl alculio)
Phllialic anhydride
M-Uulyl alcohol
Phlhalic Anhydride
lilhyl alcoliol
Phlhalic Anhydride
lleplyl alcohol
Phlhalic Anhydride
tsodecyl alcohol
Phlhalic Anhydride
Methyl alcohol
Phlhalic anhydride
Methyl alcohol
Teiephlhalicacid
Methyl alcohol
/>-Xylene
Phlhalic anhydride
M-Oclyl alcoliol
2-£lhylhcxyl alcohol
Phlhalic anhydride
Acetic acid
Ethyl alcohol
OWNKR OF PKOCKSS
UP Chemicals International, Ltd.
Mitsubishi Petrochemical, Ltd.
Nippon Shokubai Kagaku Kogyo Co., Ltd.
Toyo Soda Manufacturing Co.. Inc.
UP Chemicals International. Ud.
IIP Chemicals International, Ud.
Rhone Progil
UP Chemicals International. Ltd.
UP Chemical* International. Ltd.
Nihon Yuki
Eastman Kodak Co.-Tcimciscc Eastman Division
MiCsui Petrochemical Industries, Ltd.
Standard Oil of Indiana
Dynaiiiil Nobel AG
Kalzclimaiin/Simon Carres
C.W. WHICH
UP Chemicals International, Ltd.
Ijiukro
Niliou Yuki
Khonc Progil
UP(%emicals Inlcrnalional, Ltd.
Laukro
Pfaudler
KlioneProgil
UP Chemicals International, Ltd.
NO. Ol
LIOKNSKU
COMMERCIAL
PLANTS'
1
1
1
N
U
-
U
1 '
2
2
U
-
-
2
2
14
25
13
14
2
4
U
6
2
4
4
6
U
TOTAL NO.
or u.s.
COMIIKRCIAL
PLANT'S1
(")
-
-
-
(5)
(0
(10)
-
(4)
(1)
-
(8>
(5)
(7)
—
-
_
-
-
(0)
-
-
-
(10)
-
-
-
(II)
' U At Icwtl one pliial cukli. but tulul b uiikauwii.
N- Nu cumiuurcUl plunts.
t\i(cuUics«:s iitdkiile uuiiilici of U.S. |ir4jJudny |4jntt
of piucc
-------
MAJOK UNITPROCESS-ESTERIFICATION (Continued)
oritiiit
HEQUIKEU
PHOCIiSSUS
Pyrolycit
Oxidation
None
None
Pyr»ly*l*
llydfocyinalion
llyiifolyiii
Sullbaalion
Oxidation
*~ Carboxylalion
PulymcfUation
None
None
PRODUCT
Ethyl iiceluiicelale
Itlhyl aciylale
Isupiopyl acetate
Methyl acetate
Methyl acetoacclale
Methyl mclhacrylale
Methyl iiicllmciylale
f^Oxybeiuuic acid and
f>-Oxybenuiic bulyrali)
Polyethylene lerepblhalalc
Tiiacelale polyinei (Cellulose triacetate)
T(ibuiyrin(Glceryl Icibulyiale)
IttUSTOCK
Acetic acid
tilhyl alcoliul
lilliyl alculiol.
IVopyleiie
Acetic Acid
Iwpropyl alcohol
Acetic acid
Methyl alcohol
Acetic acid
Isoprupyl alculuil
Acetone
Hydrogen cyanide
Methyl alcohol
Isobulylene
Methyl alcohol
Butyl alculiol
Carbon dioxide
Hlienul
Ulhyleue glycol
Terephlhalic acid
Acetic acid
Cellulose
n-liulyric acid
Clyceiol
OWNtK Ol- WOCIiSS
Wiiclier-Ciieiiiie
-
UP Clieinicals International, Ltd.
UP Chemical* International. Ltd.
Waclcerdtemie
Montedison S.p.A.
Sumitomo Chemical Co.
Gulf Oil Chemicals Co.
Milsui Chemical
llcicclul
ICI
Invenla-Eim
Toiay Indusliies. Inc.
Zuiiiuci AG
Momefibre S.p.A.
Nilion Yuki
LICENSED
t'OMMCRClAL
PLANTS'
U
-
U
U
U
1
1
N
U
U
U
12
U
36
2
N
Ol; U.!
COMUt-Kf.
PLANT
2
(5)
(3)
(8)
(1)
(4)
-
-
-
(21)
-
—
-
-
-
-
1U - ill Icusl one exists, bul lulal is unknown.
N - uul tuiimicicUl.
f«iculUc»ei ittdtctlc lolal ou. ul U.S. piutlucing pteul* reiaidlcu of pioceu.
-------
MAJOR UNIT PROCESS-IIALOGENATION
OTHER
REQUIRED
PROCESSES
Ainmoxidalioi)
llydrogenalion
None
None
None
None
None
None
None
None
None
None
None
None
None
None
None
Pyiolysis
None
None
PRODUCT
Adiponilrile, llexamelliylcue diamiue
Ally) chloride (3-chloroprcne)
Uciuyl chloride (o-chlorolohicne)
Uromoform .
Carbon lelrachloride
Carbon lelrachloride. Perchlorueihylene
Carbon lelrachloride. Perchloroelhyleiie
••'liEOSTOCK
UuUdieue
C'hloruacclk ucid
Cliloiobenune. mono (MCU)
p-Clitoio-in-ci ant (2-chlo(ii-5-liydfO»y toluene,
4-clilofO-3-meiliylplicnol)
Cblununellianes/Caifaon Iclracliloride, Clilixofunii.
Methyl cliluiidc. Melliylene cliloiide
2 Clilun>iui|>hlliiileiic
Clioropiciin (Iricliloroniiio inelluine)
C'hloiopiene (2-clilorobuiiidiene-l ,3)
Cyanuric acid, Sodium dicldoiotsucyaiiuiale,
Tiichloioisucyauufii; acid
o-Uicliluiobenzcnc (1 ,2-dicliloiobeiuciu:)
/>-l>iclilo(obeiuenc ( 1 ,4-dicbloiobeiuciu:)
ni-DicldtHobeiuenc ( 1 ,3-dicliloiobeiucne)
OWNER OF PROCESS
NO. OF TOTAL NO.
LICENSED 01- U.S.
COMMERCIAL COMMERCIAL
PLANTS' PLANTS'
(7)
Propylenc
Tohicne
Chloroform
Hydrogen bromide
Carbon disulfide
Methane
Propane/propylenc
Acelaldchyde
Acetic acid
Ueiuene
,,,-C,«ol
Methane
frNaphlhol
Phenol
Picric acid
Uuladiene
Caustic soda.Chloiine. Urea
Ueiuene
Ueiuene
-
-
-
Diamond Shamrock Corp.
Suuffcr Chemical Co.
Rhone Progil
Scicnlific Design Co.
Slauffcr Chemical Co.
Rhone Progil
Scientific Design Co.
Slaufler Chemical Co.
Diamond Shamrock Corp.
-
-
-
Diamond Shamrock Corp.
Scientific Design Co.
Slauffcr Chemical Co.
-
-
Mitsui Chemical
UP Chemicals International, Ltd.
Shikoku Kasei
Miltui Chemical
_
-
-
-
U
4
3
5
S
u
s
1
1
-
-
-
u
1
-
-
u
3
3
1
_
(5)
(4)
(2)
(2)
(4)
(4)
(2)
(3)
(H)
(3)
(6)
(1)
(2)
(S)
(3)
-
(7)
(2)
*U- Al Icuil uaepLtnl «ni«ii. but laul U uukaawa.
N No cuiniucicUl HJDU.
Pafcnihcscx indicate number of U.S. pto
gai diets o( pi
-------
MAJGK UNIT PROCESS-IIALOGI-NATtON (ContiuueJ)
OTIIL'H
HIXtlllHl-l)
pRntiisst3 pHouuer
Condensation Dichlorodiplienyl Irichloroelhane 11,1,1 -Irichloro-
2.2-bb(>chloropheuyl) ethane| (DDT)
None 2,4-Dichlorophcnol
None 2,4-Dichlorophcnoxyacelic acid (2,4-D)
None 1,2-Dichloropropane
None I .J-Dichloropropane (1,3 D)
None E Ihylcne dibromide (1,2-dibromoelbane)
1-litUSIOfK
Ace (aldehyde
Monochlorobcnzene
Phenol, 4-chlorophenol
Monochloroacelic acid
Phenol
Piopylcnc
Allyl chloride
OWNliR Of PHOCESS
Diamond Sluiiiiiock Corp.
Diamond Shamrock Coip.
Niuau Chemical liidusliiei
NO. Or TOTAL NO.
1.ICENSI-O OV U.S.
COUMEMCIAL fOUUi:KClAL
PLANTS' PI.AN'I'S1
U
U
U
(I)
(3)
(ID
(5)
(I)
(4)
00
None IUhylcnedichloride(l,2--nilro- 0.0-Dimelhyl phosphorolhionochloridale Slaull'cr Chemical Co.
phcnyl phos|>horolhioali!) Sodium nilrophcnoxide
None Fluorocuiboni Carbon teliachloiide Daikin KogyoL'o., Ltd.
llydrolluoricacid KhoneProgil
None Fluorocai bons llydrolluoricacid Montedison S.p.A.
Methane
Propylcne-*allyl chloi ide-^epichlorohydi in —
Cbloiohydrinaliim Glycerine (Glycerol)
llydrolytii
None llcxachlorobeiuene (IICU)
(Perchlorobenzene)
Uciuene
Diamond Shamrock Corp.
Mitsui Chemical
Slauifer Chemical Co.
U
6
1
5
U
2
U
18
U
N
U
2
U
2
1
-
U
U
2
(17)
_
_
-
_
_
-
_
_
_
-
(2)
(16)
-
-
(2)
(2)
-
_
* U At tasi uitc pLiul ckisih, bul (uUl U unkuuwii.
N No cuiuiiicicial PUnl*.
'l^icuiliciicii iiitticuic uutulicf ui U.S. i
ul prm-c
-------
MAJOR UNIT PROCESS-IIALOGENATION (Continued)
-p-
vo
OTHER
REQUIRED
PROCESSES PROIIUCT
None llexachkuobuladiene
Pyrolysis llexaclilorocyclopenladiene
(Perchlorocyclopenladicne)
None llexachloroelhane
None Methyl cldoride (cldorumelhane)
(Melhylene cldoride, Cldoroform arc co-producli)
Condensation 2-Mclhyl-4-ch!orophenoxyacelic acid
(MCPA)
None Melhylene chloride (dichloromelhane)
(Chloroform co-product)
None Melhylene chloride (Methyl chloride.
Chloroform are co-producls)
None Melhylene cldoride (Methyl chloride.
Chloroform are co-products)
Condensation Methyl paralhiou (0,0 Dimethyl O/)-
nilrophenyl phospiiorulhioale) (MPT)
None Monochloroacelic acid
None Peiilachhiro|ihcnol
Cracking (catalytic) Pcrclduroelhylcne (lelracldoroelhylene)
(Trichloroelhylcne-co^iroducl)
Cracking (catalytic) Percldoroelhylene (lelrachloroelhyleiie)
(l'richloroelhylene-co-producl)
(.'racking (catalytic) ( Perchloroelhylciie (lelrachloroelhyleiie)
Oxyhalugenalion (Trichloroelhylcne-cu-producl)
IttUSKK'K
OWNtK Ol- fKOCtSS
Bulidkne
Penlane
Tclrachloroelhane
Meilunc
Monocltloroacelic acid Mitsui Chemical
Methyl chloride Diamond Shamrock Corp.
Milsui Chemical
Slauffer Chemical Co.
Methane
Mcllianc and Melhanol -
0,0-Diinelhyl phosphoroihionochloridaie Slauffer Chemical Co.
Sodium p-nilrophcnoxide
Acetic acid Milsui Chemical
Uniroyal
Phenol
Elhylene dichloride
Acetylene
Any C2 cldorocarbon mixture
Diamond Shamrock Corp.
Rhone Pragil
Scientific Design
Wacker-Chemie
PPG Industries
NO. 01 TOTAL NO.
LICENSKU Ol U.S.
COMMERCIAL COMMERCIAL
PLANTS' PLANTS'
(3)
(3)
(I)
(2)
(2)
(i)
(I)
U
U
U
2
—
1
U
U
-
U
1
5
3
(2)
H)
(3)
-
(5)
(ID
—
-
-
1 U* Al Icasl unc pUal exiiU, but luul U uniauwa.
N No cuuuittidul Plants.
iiilltiiie nuiubci ol U.S. ptuju^iag plants icgaidkn 4if piuccu.
-------
OTHER
REQUIRED
PROCESSES
MAJOR UNIT PROCESS-IIALOGENATION (Coulinued)
PRODUCT
FEEDSTOCK
OWNER OF PROCESS
NO. OF TOTAL NO.
LICENSED Of U.S.
COMMERCIAL COMMERCIAL
PLANTS' PLANTS'
None
Phosgene
Ui
O
Chlorohydrinulion Propyleno oxide
llydiolysil
Nune I.l.2.2-Tciiachloreihanc
None 1.2.4-Tficulorobeiucnc
None 1,1 ,1-Trichloroelhaiie (Methyl chloroform)
llydrohalogeiulion 1.1,1 -Tricldoroelhane (Methyl chloroform)
None 1.1.2-Trichloroelliane
Nune 2.4,6-Tiiclilorophenol
Condensation 2.4.5-Trichlorophcnoxyacelic acid (2.4.5-T)
Clacking (catalytic) Vinyl chloride nionuiuei ( VCM)
llalogcnalion
Cracking (Ilicrnial) Vinyl chloride monomer (VCM)
Oxyhalogenaliou
Cracking (catalytic) Vinyl chloride monomer (VCM)
Dehydiiihalogenaliou
Oxyhalogeiulion
Cracking (catalytic) Vinyl chloride monomer (VCM)
Cracking (catalytic) Vinyl chloride monomer (VCM)
Uehydiohalogenalion
Oxyhalogenaliou
f4onc Vinylidene chloride ( 1 ,1-dichloroelliylene)
Carhon monoxide
Propylene
/c/7 Butyl alcohol
(recycled)
Chlorine
lilhanc
1,2-Uichlorobeiuene
Hlhyleue
Vinyl chloride
Elhylene
Phenol
Acetic acid
Trichloroplienol
Blhylene
Ulhylene
lilhane
Acetylene
Naphtha
Blhylene
Crawford & Kusscll
Slauffer Chemical Co.
Zimmer AG
Liimmtis
Oelrcx/Scienliric Design
Diamond Shamrock Corp.
Montedison S.p.A.
Uomanlo/Scientific Design
Rhone Progil
Sluuffei Chemical Co.
Union Carbide
U.F. Goodrich Chemical Co.
Transcal/The loinunusCo.
Monocheni, Inc.
Kurclia Chiyoda
Nippon Zeon Co.. Ltd.
14
S
2
N
I
6
2
22
I
26
(19)
(0)
(I)
(4)
(3)
(3)
(I)
(I)
(II)
(I)
(3)
1 II • ai iatii HOC CKUU. bui lutiil U unknown.
N - aui cuiiimtiickit.
Pjtcnlbciicl iudivtf Ic Itilvl nuutbci ul U.S. pimlutiog ploau
i «tl' pi ucctt.
-------
MAJOR UNIT PROCESSI-S-IIYDROGENATION
OTHER
REQUIRED
PROCESSES
Ainmoxidallon
llulogenalion
llydrulyiiU
Suiroiialiun
Acid Rearrangement
None
None
Carbonylallon (two)
PRODUCT
Adiponilrile
/n-Ainiiiouhenul
f>-Aininophenol
AuUine
1,3-Bis(amuioineihyl)cyciahexane
n-Bulanol/n-Bulyraldehyde
FEEDSTOCK
Butadiene
Nitrobenzene
Nitrobenzene
Nitrobenzene
Isophthalonllrile
Piopylene
Carbon monoxide
OWNER OF PROCESS
Sumitomo Cliemlcal Co.
Lonza/ftrtl Chemical Corp.
MiUul Chemical
Sumitomo Chemical Co.
Mitiubiihi Gas Chemical Co./Badger
BASF AC
NO. OK TOTAL
LICENSED NO. OF U.S.
COMMERCIAL COMMERCIAL
PLANTS* PLANTS'
(7)
I 0
U
I
I
I
2
(4)
(7)
(0)
(7)
Acid Rearrangement
Oxidation
Condensation
Dehydration
None
None
None
Nmie
Benzldlne Rearrangement
Caibonyliillon (oxo)
Caprolaclam
Crotoiuldchyde,
fl-Bulyraliknyile,
M-Uulyl alcohol
Cycluliexaue
Cyclohexanone
Cycluhexylainlne
Cycliiliexylamiiie
3,3'-l>ichlorobenzidinediliydrocliloride
2-l:iliyUiexaiiol
n-Butanol
kobulyraldehyde
Toluene, Ammonia
Acelaldehyde
Uciucne
Hieuol
Aniline
NiliubeniCiic
I -Cliloro-2-nilroben/ene
Carbon monoxide
Propylene
SNIA Viscoa U
BP ChemicaU Inlerrulional U
Kyowa llakko I
Ailnutlc Richfield 2
lloudry Div. Air Prod. & Cliein. 2
liutilut Francaii du Pelrolo 12
Uinimui N
Hiillips Pelioleum Co. 4
Scientific Design I
Sinclair-Eiigclliard Ind. U
Slamicarbon S
Texaco Development Corp. U
Toray Ind. Inc., llyloray I
UOr>PruceuDiv.,iiydrar I
Slamicarbon 2
Abboll-EngMiard Ind. U
l-nglchard Ind. U
BASF AC 6
Ruhrcheinie AC
Ruhrcliemie AG/Rlione Poulenc SA 12
Moruanto N
(2)
(2)
(ID
2
(4)
(2)
(5)
1 U- Al leail 0110 pUul culm, but lulil Is unkauwa.
N-Na com me I dJ plunU.
PaicnlbcKci iatllcalo lul J aunib«( of U.S. pitxluuinji ptauli rcgiudlcu of pioccu.
-------
OTIIIiH
MEOUIKKD
Condensation
None
Ammoxidalion
Condensation
Carbonylallun (uxo)
Alkylaliiin
Condensation
Dehydrogenalion
Condensation
Condensation
Ln
ho
Condensation
Dehydration
None
Nilraliun
Phosgcnalinn
fiMoucr
2-Clhylhexanul
Itexamethylene dianiine
llexunelhylene dianiine
llydrazobcuicne (lyin-
N.N'-Diphcnylliydrazine)
Isubulyl alcohol
N lsopropyl-N'-|>heiiyl-/>-phenylcnediamine
DUMelbionine
2 Methyl 2 bulanol
Melhylisobulyl kelone
Sorbitul (1.2.3.4,5,6 llexanehexnl)
Toluene diisocyanalc (ll>l)
(80/20 2.4-2.6-TDI)
l-'EKUntlOC
Acetaldehyde
Adiponilrile
Adipic acid
Ammonia
Niliuben/ene
Propyleuc
Acetone
Aniline
u-Cldoronilrobenzj
Acrulein
Cyanic acid
Methyl mercaplan
Acetone
Acetylene
Acclune
Com sugar or
Corn syrup
Phosgene
Toluene
Nune
m-Xylcnediamine
MAJOR UNIT PUOCESSHS-HYDKOGENATION (Continued)
OWNI-R Cl PKOCtSS
Kyuwa llakko
Klione Progil
Mmilcfibrc S.p.A.
Ziimner/til Paio-Utauiiil
Suniilomo Chemical Co.
Sumitomo Chemical Co.
SNAM I'tugelli
UP Clieniicals Inlernalional Ud.
Texaco Develiipineul Co.
lingcllurd bid.
Allied Chemical
IMC
Nippon Soda-Nissan
Suniitumo Oiemical Co.
Miliubishi da Chemical/Badger
NO. Ol: TUTAL
i ICI:NSI:I> NO. or- us
COMUEMCIAL COMMIiKDAL
PLANTS I PLANTS >
Uopliilialonilrik!
1
1
1
1
-
-
1
1
U
3
U
U
U
N
U
1
1
(U)
-
(6)
-
1
(8)
(3)
(2)
(2)
(5)
-
(6)
(10)
-
_
-
1
U-Al least one plant e*UU. but loliil u uukuuwu.
N-No toinni
indknU lutal ouinbci of U.S. piuduLiiig pltuiu lugii
-------
MAJOR UNIT PROCESSES-IIYUKOIIALOGENATION
MEQ.UIKEU
FROCKSSKS
Aimniiittlioii by
Amminulyiiis.
Condensation
None
Condensation
Pyrolyiii
None
None
I lalogc nation
None
fHOIHILT
Choline chloiido
Hlliyl chloiiilc
Isopiene
Melhyl bromide (Bfoinomelhaiie)
Methyl chloride (Cldofoinelhane)
1.1,l-Trichloroclhane (Methyl chloroform)
Vinyl cliluiiile
Ui
OJ
1-MiUSTOCK
blliylcnc oxide
Tiiinclliyljiiiinc
ttliylene
HoiinaUckyde
liubulylcne
Melbanol
Mclliaiio!
Vinyl cliluiiile
Acetylene
OWNUK or f KOt'tSS
ucu
SuulTci
buyer
Muralhon Oil
-
Diamond Shamrock Coip.
Slaurfei Chemical Co.
-
Ulaw Knox
Ccawfoid & Kuuell
llulii
Miuui Chemical
Scientific Design
Wacker-Chemie
NO. Oh'
LIOINSKU
tXJMUtRCIAt
PLANTS'
1
1
N
N
-
1
2
-
1
2
2
V
2
4
TOTAL NO.
01 U.S.
COMUI-KCIAI.
PLANTS'
(6)
(7)
(6)
-
(3)
(10)
-
(3)
1
_
-
_
-'
.-
1U- Al Icul oiie phial cfcUu, but lulit is unkuuwa.
N-Nu cumincrtLiJ plwi*.
Fiuenlhetu iudimie lulal aumbei ul U.S. piuduciu| i>Unu icgutilvu of piacus.
-------
MAJOR UNIT l'KOCliSSKS-IIYI)HOLYSIS|HYI)KATION|
cn
OTtmtt
HCQIJIKCD
PROCESSES
None
None
Sulfonalion'
Sulfonalion
PKOUUCT
Acclic acid. Melhauul
Acrylamide
Alcohols, mixed lineal, sulfaled,
aiiiiuuniuin tall
-. nudiuni tall
-. Irielhanolaminc sail
-, unspecified
Alkylbenzene uilfonales
Oxidation
Elliylenc oxide, blhylene glycol
l-'L-tDSTOCK
Melliyl acetate
Acrylonilrile
Fatly alc4iliij|s, tull'ur trioxide
Alkyiben/enes, lulfui Irinxidc
llydrugeiialiou
Siilfonalion
Siiironalion
None
(lilorohydrinalion
None
None
None
,,,-Aminophcno,
tec-Butyl alcohol
tec-Butyl alcohol
Epichlorohydrin
Ethyl alcohol
Ethyl alcoliul. Ethyl ether
Elhylene glycul
Nitrobenzene
Uulylene
Bulene-l/Buiene-2
Ally! chloride
Itypochlorous acid
Elhylene
Elhylene
Elhylene oxide
Elliylcne
NO. 01 TOTAL
LI«-:NSI:» NOOI ui
(,'aibouylaliiui
Foiinic acid, Sodium fornialc
Caibon monoxide
Sodium hydioxide
OWNCK OF PftOCKSS
Wachei-Clicinie
Sumiloino Clieimca) Co.
Cticinilhon
MoDo Kcini All
Ctieinillion
lluls
MoDo Kend AU
Sinnilonio Chemical Co.
Scientific Desigii/Maiuzcn Oil Co.
Texaco Development Corp.
Union Caibide
National Dulillen
Shell
Veba Chemic AG
Union Carbide
Vulcan-Cincinnati
U.S. Industrial Chein. Co.
Iliils
Japan Catalytic Chemical liid. Co.
Scienlific Design
Shell
Hull
Ja|Uii Catalytic Cheni. Ind. Co.
Nippon Shokubai Kagako Kogyo Co. Ltd.
Scientific Design (k'lhylene oxide only)
Shell
SNAMProgetliS.p.A.
Union Carbide
SlautTer Chemical Co.
I-LANTS'
N
1
U
s
-
-
-
U
1
s
1
1
U
1
1
s
5
1
3
4
60
1
22
4
6
3
49
30
3
I VIB1MI I*V
PLANTS'
(10)
(4)
0>>
<2)
(-0
(2)
(0
(10)
-
-
(0)
(4)
-
(3)
(6)
--
-
-
(IS)
-
-.
-
-
-
_
-
-
(2)
one |il4Ul tfcisl*. but luiul is unknown.
N Nti cuiumci
l^a-iilllL'urk iiiJL'iili: luUl iiuntbct itl U.S. pitttluiiii
icgiif Jlwik ul iiiucuu
-------
oTiir.k
HEQUIMW
PKOCKSSES
Caibonylalioii
Ciindcnsalion
lipuxidalion
Chlorohydrlnaliua
llalogeualion
Hydrolysis
Sulfonalion
None1
None
Dchydiogcnation
Oi lisierilicalion
llydrocyanallon
SuU'onalion
Summation
None
None
Sulfoiuillon
Oxyhalogenallon
Acid cleavage
Alkylalion
Oxidation
None
Chlorohydriualion
llalogenalioii
puouucr
Formic acid
Glycerine, Acclic acid
Glycciiue (Glycerol)
liopiopyl alcolml
Isopropyl alcolml
Malcic acid (i/«-l.2 KlliyUaedicarboxylic
acid
Methyl ethyl kelone
Methyl mclhaciylale monomer
2-Naplulio!
Penlacliloropheuol
Phenol
Phenol
Phenol
Plieuol, Acetone
Propyleue glycul (1,2-Diliydroxypiopane)
Propylene oxide
MAJOR UNIT PROCESSES-HYDROLYSIS |IIYDRATION| (Conliiiucd)
I I:I:I>STOTI:
Carbiui monoxide
(Melhaiuil -recycled)
Ally! alcohol, paracelic acid
Propylene ->allylchloiidc-*epichlorohyd(in
Propyleae
Propylene
Maleic anhydiide
Uulciie-l/Uulenc-2
Acetone
Hydrogen Cyanide
Melhauol
Naphllialene
llexachlorobenzenc
Monochlorobeniene
Uenzene.uuTurtc acid
Iknzene, hydrogen chloride
Cliloroliydiinalion Piupylene oxide
U- At k;akl unc plaitl cxisu. but lulj U unknuu/u.
N -No cuiiliibrfciitl |)UnU.
3 PaicnllieiCft iu4kiilc lulul uuinbcf of U.S. pluduciaf pUuls itigardJcu ol' piuceu
J A diiccl taliilylic liydrulyib pitKXsa.
Piupyleue oxide
Piopylene
ltf/-llulyl alcohol (recycled)
Chlorine
Propyleue
Chlorine tolulion
OWNliK Ol f
The Leoiiaid P«>ccss Co. Inc.
Daicel. Lid.
UP Clieiiiicub Inlefnaliunal Lid.
M. W. Kellog
Texaco Development Corp.
Veba-Chemic AC
Deulscbe Texaco AC
Tokuyama Soda Co.. Lid.
Uowmaiu Chemical
Texaco Uevelopinenl Corp.
Montedison S.p.A.
Sumitomo Client. Co.
Milaul Chemical
Diamond Sliamiock Corp.
Hooker Chemical Co.
Milusi Chemical
I looker Chemical Co.
Union Caibide
Allied Chemical
Iluls/Uaycr
Mitsui niemical
Lunimui
BASF AG
Iluli/Uayer
Union Carbide
NO. CM-' TOTAL
LK'IJNSI U NO. (II U.S.
COMUIiKCIAL CXJUUI-RCIAI
PLANTS' PLANTS'
N
(»
(2)
4
N
U
5
1
1
U
1
1
U
U
3
U
3
1
U
2
U
N
1
2
(5)
-
-
-
-
-
(7)
(-1)
-
(1)
(5)
(17)
1
-
-
-
(6)
-
(0)
(6)
—
-------
MAJOR UNIT PROCESSLS-NITRATION
o>
OTHER
REQUIRED
PROCISSbS
Amiiulion by
Reduction
None
None
None
None
PRODUCT
0-Aminuphenol
4 ,6-Dinilf o-o-cf not
2.4-DiiiiUophenol
2.4-Diniliuloluene
2,4-(aiiii 2.6-)-l>iiiiliolulueiie
1'EEUSTOCK OWNER or PROCESS
Ilienul -
Cieiul
Ilienul
Toluene —
Toluene Mcissiiei
Suniiloino Chemical
NO. Ol-
LICENSED
COMMERCIAL
PLANTS'
-
-
-
-
U
1
TOTAL
NO.OI-U.S.
COMMERCIAL
PLANTS*
(2)
(0
(2)
(S)
(S)
-
Nuue
Nluubenuiie
Ueiizeue
Suiniloino Clicnilcal Co.
Uiiifoynl
None
None
None
None
None
llytlrogcnulion
Iliosgenaliun
o-Niltuplienol
p-Nilruphenul
»i-Nilrololuene
o-Nilrululueiie
yi-Nilrulutucae
Toluenediiaocyaiiale (1 1)1)
(80/202.4=(2.6-TI)I)
I'litnul
Hieno)
Toluene
Toluene
Toluene
fliosgene
Toluene
Uiazzl
Uiazzi
Mei&snec
Uiazzi
McUsnei
Allied C1i<
I-MC Cor|
Nippun Soda-Nissan
Siiiniiuinu Chemical Co.
U-A| Ictul uiie |tJuut ukisiM, bul luiul U uuknuwu.
N-No 4^tii
(«)
-
-
U
U
U
U
U
U
U
N
U
1
(2)
(4)
(1)
-
U)
-
(2)
-
(10)
_
-
_
kiilo lulul number of U.S. iinMtuciiig |4iiuu tc$uttte»x of ptuceu,
-------
MAJOR UNIT PROCESSES-OXIDATION
Ul
OTIIliK
UI-QIIIHI'U
PKOCESSliS
Nune
Alkylaiiou
Nune
None
None
None
Clacking
None
Hileriflcaltun
None
None
None
None
None
Beckmann Rearrangement
Nilrosalion
Acid Rearrangement
I lydiogenalion
None
Ksterificalion
Csleiilkalion
NO. OH TOTAL
IJCIiNSLK NO. OH U.S.
PRODUCT
Acelaldchyde
Acetic Acid
Acetic Acid
Acetic Acid. Peiacelic acid
Acetic Acid, Tereplilhalic acid
Acetone, Phenol
Acetylene. Elhylene
AcuJelii. Acrylic acid.
Acelaldchyde
Acrylic acid. Acrylic esleit
Adipic acid
Adipic acid
Anlhraqulnone
Beiuoic acid
/-Xylcne
Ethyl ak.Ui.J
Propylene
OWNllK OF PHOC^SS
Aldeliyd Ombll
Uayer AC
UP Clicmicak Inlcrnallonal Ud.
Wacker-QienUe
Gulf Oil Chemical* Co.
Allied Chemical
Union Carbide
Standard Oil of OMo
UP Chemicals International Ud.
Milsubulii Petrochemical* Ud.
Nippon Sliokubai Kagaku Kogyo Co. Ud.
Toyo Soda Manufacluilng Co., Inc.
GuirOilOiemicaliCo.
Veba-Chcmle
Zimmer/EI Paso
Nippon Steel Chemical
Toms River Chemical
SNIA Visciua
Slamicaibon
Invenla AC
SNIA Viscma
Inslilul h'rancais du Pelrole
Scieiilific Design
Slumicaibon
Zimmcr/KI I'aso
Dyiuniil Nobel
Kalzcluiuun/Siinon Caivei
C. W. Widen
PLANTS'
25
N
6
1
N
U
3
4
t
1
1
N
N
2
1
U
U
3
-
13
6
2
1
12
1
25
14
14
PLANTS1
(5)
(10)
-
-
-
(17)
(10)
(2)
(0
_
-
-
(6)
_
-
(1)
-
(5)
(2)
(3)
-
-
(6)
_
-
(7)
-
-
(5)
1 U- Al level uiu) ubnl cxixls, Inn lulul b uuknown.
N - No euninieruitl plunti.
PiiluulliCMrk indkalc lukil uuiitbcr uf U.S. pioducing planli
-------
MAJOR UNIT PROCESSES-OXIDATION (Continued)
OTIIKH
RKQUIHEU
PKOCI-SSliS
None
Hydrolysis
None'
None4
01
00
N»ne4
None
Isuinerizalion
Nune
None
Dehydration
Dehydration
PRODUCT
Clhyleue oxide
tilliylttne oxide/lilliylene glycol
Formaldehyde
Formaldehyde
Formaldehyde
Formic acid
Fiinuric acid (tnu»-l ,2-Clhylene
dlcarboxylic acid)
Glycerine
Isophlhalic acid
Maleic auhydiide
Maleic anhydride
' U - Al lean one plan! cxiill, bul lulal U unknown.
N- Nu uHitmeicU pUnlt.
1 Kiicnllieui indkilc lulal ounlbci ul U.S. piodudnt pUnli icfaidlcu of piuccu.
Sllvci caliitfll.
'Mclul ukide catalyst.
ittosroctc
liltiylcnc
Elhylcnc
Mcllianul
Meihanol
UUnelhyl elhei
Uglil liydrocailiuiu
Ueiucne
Hcopylcne
ui-Xylene
Duladicne (t oilier
C4 liydrncarb
-------
MAJOR UNIT PROCESSES-OXIDATION (Continued)
OTlll'H
PUOCLSSIS
Dehydration
EsleriTicalion
Oionolysis
O/onolyus
Acid cleavage
Acid cleavage
Alkylalion
Ln Dehydrogeiulion<
vo
None
Alkylalion
Alkylalion
pKOinxrr
Malelc aiiliydride
Mclliyl niclhacrylale
Pelarguiic acid
Caproic acid
Azeliac acid
Pdargouic acid
Uudecanoic acid
Tridecanolc acid
Phenol
Acetone
Phenol
Acetone
Phenol , Hydrogen
Phlhalic anhydride
Plilhalic anhydride
Pyruniellillc dianhydride ( 1.2.4.5-
l ti-usrock
Buicne-l. Uuleue-2,
Ouladiene (if present)
Isobulyleiie. Mellunol
OUi (tall, red. loyabean)
o-Olefhu
Cumene
Benzene, Piopylcne
Cyclohexane
Naphthalene
u-Xylene
IS,cni]»cuiiiciic
OWNI'H Ol< PKOCtSS
Uayer-Lurgi Corp.
Gulf Oil Chemical
Welsbacb Corp.
Wekbach Corp.
UP Chemicals International Uil. and
Hercules Inc.
Uhone-Pooleiic
UOP Process Division
Allied Chemical
Scientific Design
Inslilul Francaii du Pelrole
Nippon Steel Chemical
Scientific Design
Sherwin Williams/Badger
United Chemicals & Coke. Ltd.
Von lleydcu
Alusuisse
UASI- AG
Khone-Poulenc S.A.
Scientific Design
Von Hcyden/Wacker
Gelsenberg-Cheinie GmbH
tICEN!
/V\UUI>'t
\.\)mltat't
PI AN
1
N
U
N
22
5
3
U
1
N
U
8
14
U
U
3
20
7
4
65
N
Oionolysu
be nzenelclracarboxylic-l .2.4,5-
dianhydiide)
Suberic acid
Dodccanoic acid
Cyclic otelliu
Welsbach Corp.
Nit. 01- TOTAL
NO 01-US
PLANTS1
(4)
(H)
(ID
1 tl- Al foiul owe pkinl cxUli. but tula) U unknown.
N -Nu couiiacfdd ptuili.
3 PiiienUwscs in ilk He total ouiubci of U.S. (iioduting plants
-------
MAJOR UNIT PROCESSES-OXIDATION (Continued)
onii-ft
PHOCIiSSI3
None
Cundeusaliun
Cimdeiualion
Nwie
PKooucr
Tereplilhutic acid
Telialiydrufuraii, 2.3.4,5-
lclrac«itiotylic diaiiliydritle
Tcliamelliyllliiuram diiulflde (Thluram)
Triiucllilic anhydride ( 1 .2.4-Uciizenc-
Iricaiboxylic acid. 1 ,2-anliydiidc)
p-Xylciic
Kuiun
Maleic
Aniiuunta, Caibou duulflde,
Dinuiliylauilne, Hydrogen
pcioKidc
Rsuediiciunetie
NO Ol' TOTAL
IITKNSIO NO. OF U.S.
OOUMIiRCIAL COMMKKCIAL
PI AMTSl PI A MTV*
OWNIIK OF fKOCKSS PLANTS1 PLANTS1
Eastman Kodak Cu.-Tcnneisee Eastman Oiv. I (3)
liulilul l-'iaiicaU du PeliiJo N
I^JIUIIIUK U —
Siandaid Oil Cu. (Indiana) 26
Toray liid. Inc. 2 —
Uni-liab I
GelwiibcigCheiiiieGiiibll N (2)
UCU I (S)
Standard Oil Co. (Indiana) I (I)
*U-AI Icttkl uiic |4*ul uftlsls, but lolul U uukuown.
N - No coiuineKUl |ilanu.
ilicKto lulal uuiubcr uli U.S. piu«!ui:iiig |tluils i
-------
MAJOR UNIT PROCESS—OXYHALOOENAT1ON
OTIIEtt
REQUIRED
PROCESSES
None
llalogeiulion
Clacking (catalytic)
PRODUCT
tlhylene dichloiidc
Pcichloiaeluyleue
Tiichlorocllrylene
l-liliUSTOCK
lilhyleiie
Any C2 chluiuciiibun mixture
OWNliK OH PHOCI3S
BF Goodrich
Monsanlo
Kliune Ptogil
Scauffer Chemical Co.
PPG Industrie*
NO. OF TOTAL
iictNstu NO. or u.s.
tOUMI-RClAL COMMEUCJAL
PLANTS'
17
5
2
8
PLANTS'
Hydrolysis
, Clacking (catalytic)
' Ikilugeiulion
Crack ing (catalytic)
Dcliydrolialogenalion
Iblugetulion
Clacking (catalytic)
Dclrydrolialo|;enalian
Iblogcrulion
Clacking (thermal)
n.enol
Deiuene
Hydrogen cliloride
Vinyl cliloridc rnononui (VCM) tlhylcne
Vinyl cliloridc rnorrurnei (VCM) lUlraue
Vinyl cldoiide rnonomei (VCM) Naphtha
Vinyl cldoiide munumei (VCM) tlhylenc
Hooker
Union Carbide
B.F. Goodrich
Montedison S.p.A.
Monsanlo/Scienliflc Design
Rhone Progll
Slauffer ClieinicJ Co.
Union Caibide
Tiariicat/Lurnrnus Co.
Kureha-Cluyoda
Nippon Zcou Co. Lid.
BF Goodrich
6
2
22
I
3
I
26
(ID
(I)
1II-Al Icul one plant eiisU, but rolj u unkuowu.
N~No cuuuiierclitl pLuili.
PaieultliMM iulKHC nuulUl of U.S. rJloduciug planll ic^ldlcu of pruccu.
-------
to
MAJOR UNIT PKOCESSES-PIIOSGI-NAT10N
OTIIKH
KEQUIRED
PKOCESSES
Natie
Dcliydrohalogenaliuu
Polymerization
llydrogeruiiion
Nitration
PRODUCT
Di)ihenyhin:lliime~4,4'-diisocyaiuile
|Mclbylenebi!(4-phenyl isocyanale)| (Mill)
Paiycaibonale icsliu
Tulueiie dUutcyunutet
(HO/20 2.4-2.6-TUI)
IlilDbTOCK
Aniline
Formaldehyde
Uisplienol A
Me Ihylenc chloride
OWNI:K ot- PKUCESS
llodogaya Chemical Co.
IJcmiUii Kouu
1'uluene
I-MC Corp.
Nippon Soda-Nissan
Sumitomo Chemical Co.
NO. Oh'
IICtNSlo
COMUKWIAU
PLANTS'
U
TOTAL
NO OF IPS
COMUI-KCIAL
PLANTS'
(3)
U
N
U
I
(10)
U-AI Icut oac plum dim. but luial b unknown.
N-Na couimcit^il pluiili.
aP
-------
MAJOR UNIT PROCESSES-POLYMERIZATION
OTIIliH
None
None
None
None
None
None
None
None
None1
None4
None1
fHOUtlLT
Acrylic reihu
Acryluuilrilc-buladiene-slyreuc icsins
(AUS resiiu)
I'poxy resiui
L'lliylcuc-piopylenc copoiynicre (lil'M)
frhyleiw-prupylene lerpolyiner (lilT)
tlliylenc-vinyl acelalc copolyiner icsiiis
Potyainide realm (Nylon 6)
Polyamide lesins (Nylon 66)
cb-l ,4-Polybuladieue
i trusroci;
AcryloniliUe
Acrylonlliile
butadiene
Slyiene
Bii|ihenol A
Bpiclilorohydiin
tlliylenc
PcopyUue
l-lliylene
Piupylaue
ElhyUiw, Vinyl acclale
Capriiliwlain
Adipic acid
llexaiiielliylene dlainine
Huiailiene
Uuladieue
PolybituUieiii;
UWNI:K Ol- PKOCI-SS
Ziiunier A(i
U. F Goodrkh
lapiui Synlhelic Rubber Co.
Toray hid. Inc.
Toyo Koalsu
Uniioyal
Ciba Ceigy Corp.
Moiiledison S.p.A./B. F. Goodrich
Uniioyal '
Montedison S.p.A./B. P. Goodrich
&>ivay SL Cie
Slaiuicarbon
Wacker-QieniUi
Beaunll Corp.
luvenla AC
Luijji
Toiay hid.. Inc.
llbe Ind.
Ziniiner AG
Ucaunil Corp.
Hull
Japan Synlhelic Rubber
Phillips Petroleum Co.
Polyiar International
SNAM Progelli
SNPA
Uniroyal
Hiillips Ptitroleuin Co.
N001-
LICICNSUU
COMMl-KCIAI.
PLANTS'
3
1
U
2
U
U
U
2
U
2
U
2
1
U
20
8
U
U
TOTAL
NO. t)l U.S.
COUIII-:UCIAL
PLANTS*
(122)
(14)
_
-
—
-
(W)
(4)
-
(5)
_
-
(IS)
_
CO
-
—
_
I
U
8
U
N
I
U
(3)
(S)
U-Al ICMI one |>Uul cxbU. but lulJ U unknuwn.
N-No MimotcicLil pUulu.
'fmcalbcwi lndk»le lulid number of U.S.
Sululioa pulyiucrfctiiltua.
Cuiubiuu polymerization.
-------
MAJOR UNIT HHOCESSES-HOLYMEKI/ATION (Continued)
OTIII;K
HBKHKU)
WOCKSSI-S
None*
None4
Dchydiolulogenalion
Phosgcnalion
None
None
None
None
None
None
CKODIKT
fatybuladieiie-acryloniliUe (NUK)
I'olybuleneii
Polycarbonate resins
Polycliloroprenc (Neoprene)
Polyester resini. Saturated
Polyester resins, Unsaluraled
PulyeUier glycols
Polyellier glycols
Polyethylene (low density)
nxusnxx
Acrylonltrile
Butadiene
Uuleiie-l/Uulene-2
Uisphenol A
Mclliylene cliloride
tldoropiene
Glycols
Pojybasic acids
Slyrene
Ulycols
Slyrene
Uusaluraled dibasic acids
luhylene oxide
Piopylcne oxide
Alcoluils
hihylene oxide
I'ropylene oxide
Hlliyleue
OWNI-H Ol; PKOCliSS
Polysai International
Uniroyal
1 liils
Pelro-Tex Chemical Corp.
Ideinilsu Kosan
UP Chemicals Inlernalional Lid.
Deuki Kagaku
IIP Chemicals Inlernalional Ltd.
DP Chemicals International Lid.
Lankro
Lankro
Mitsui Chemical
Nippon Soda
Khonc Progil
ANIC
AKCO
ATO Chemie
Uail
Elhylenc Plaslique
Gulf Oil Chemicals Co.
Imperial Chemical hid.
Phillips Petroleum Co.
SNAM Progelli
Slamicaibon
Sumitomo Chemical Co. Ltd.
V/O Ucensinlorg
NO. 01-
1 ICrNSKU
COMUIKCIAI.
PLANTS'
U
U
1
N
1
3
1
11
U
4
4
U
1
U
3
3
14
U
7
4
60
17
2
10
2
3
TOTAL
NO 01 U.S.
COMMEKCIA
PLANTS4
(9)
-
(6)
-
(3)
(3)
-
(24)
(86)
(43)
-
-
-
-
(20)
-
-
-
-
-
-
-
-
-
-
-
' U- Al buttl uue pfciul cxUl*. but lulul U uuknuwu.
N - No cummciclul pUalt.
atlicsct iuJicalo lulul uuiubei of U.S. piuducin^ ptuiU icgai Jlew ol piitccu.
-------
MAJOR UNIT PROCESSES-POLYMERIZATION (Continued)
OTIItH
UIXJUIHLU
PKOCI-SSliS
NO. OF
I.ICUNSKD
TOTAL
NO. or n.s.
None
FHonucr
Pulyelliylene (high density)
I litl)i'IOC»C
Elliylene
COMMERCIAL COMUI-iHCIAI.
PLANTS' PLANTS*
lIDIIliGnibll
lloeclul
lluls-VebaCheniie
Imperial Chemical liiduililcs
Mitsubishi Chemical IndusUici
Muiileduon S.p.A.
Naplilliacheinie
Hiiltipi Pelrdcum Co.
SNAM Piogelli
Sulvay
SUinicaibua
Sundaid OU
Uniun Ciifbide
W*cker-Chcmie
Ui
Esten
Condensilion
None
Pyiolysis
I'ulyelliylcnc lere|iliilulaU!
Pulyelliylene lereplillulale
I'ulyisubulylenc
Pulyisucyanaie
Elhylcne glycul
Tereplilhalic acid
Dimethyl lerephlhalale
Elhylene glycol
Isobtilcne
Buleues
lloeclul
ICI
InvenlarEini
Toruy hid., Inc.
Zimmcr AC
Ikaunil Corp.
lloechsl
ICI
Inventa-Ems
Zimmer AC
Chevron Research
Cosden Oil & Chem.
Orguaic dicltturiJcs
Siiilinin cyiiiute
Uaralliun Oil Co.
U- Al Icukl one pUul cxbli. bul luM b unkuuwp.
N-No cuuiumfcul |4iiuls.
2 Pufcullickck Inilicale KMuJ iiuiubci ui U.S. piiMlutlng pUau icguidlcu of uro
U
U
4
U
I
I
I
17
I
S
3
3
6
2
U
U
12
U
36
U
U
II
4
26
II
S
(14)
(21)
(21)
(I)
-------
CTv
CTi
OTIIKR
HI-QUIRED
None*
None
None
None*
Nune
None
PRODUCT
rft-PuiyiiuprenedK)
Polypropylene
Polystyrene
Polystyrene (I ligh Impact -lubber
modified)
Polyvtnyl acetate
Pulyylnyl iilculuil resins
MAJOR UNIT PROCESSES-POLYMERIZATION (Continued)
OWNliK 01- PHOCI-:SS
B. F. Goodrich
SNAM Piogctli
I'rieiltichUIIUEambll
Hercules
Isopiene
Piopyleiie
Stymie
Potybuludienc
Stymie
Vinyl aceUle
Vinyl ulculuil
Iliili VebiiCtiemle AC
ICI
Mluu Petfucheniicul InJ.-Mimledison S.p.A.
Pliitlipi PeUulcuni Co.
Standard Oil Co. (Indiana)
ATO
Uakol Scientific Deiign
DP Clieinicab Inieiualionid Ud.
Cusden Oil & Clieniical Co.
Hull
Pdyui Inlccnalional
Klionc Pfogil
Standard Oil Co. (Indiana)
Toyu Koaisu
Union Ciiibide
Cusden Technology, Inc.
llocclisl
Burden
Wacker-Cluinie
Aiccllo
NO.OF
UCENSI-U
TOTAL
NO. OP U.S.
COMMERCIAL COMMERCIAL
PLANTS' PLANTS1
3
I)
3
U
2
U
IS
3
5
6
2
II
II
U
1
U
4
U
(2)
(12)
-
_
_
-
-
-
-
(36)
_
-
_
-
O)
-
(
-------
MAJOR UNIT PROCESSES-POLYMERIZATION (Continued)
OTIItU
HIXIUIHCU
t>Koo;ssi:s
None
PHOIIIKJT
I'ulyviiiyl cliluiiile resins
Vinyl chloride
None
None
Nune
None'
None'
None
Polyvinyl chloride-acetate copolymcr Vinyl iceUle
Vinyl chloride
Polyvinyl chloride-viriylidene chloride Vinyl clitoride
copolymer resins Vinylidene clilodde
Propylcne Telroincr (Dodcccne. non-linear) Propylene
SIIK (Polybuladienc-slyienc)
SUK (Polybuladicne-styrcnc)
Urea-formaldehyde resins
UiiUdiene
Styrcne
Butadiene
Slyrene
Uiurel
formaldehyde
Uren
OWNER 01- CMOCtSS
ATOChemie
U. F. Goodrich
Burden
Diamond Shamrock
lloeschl
lloudiy OH.. Air Prod. & Chciu.
lluhi
Kureha Chemiciil Co.
Mouleduou S.p.A.
Rhone Poulenc
Scicniilic Design
Sockete National des Petrolei D'Agullulne
Solvay-ICI
Suuffer Chemical Co.
Suiniloino Cliemical Co.
Union Carbide
llnlroyal
Wacker-Cheinie
Scientific Design
Sulvay
Chevron Research
Fhillipi Petroleum Co.
Texaco Development Corp.
UOP Process Division
American Synthetic Rubber Corp.
I). !•'. Goodrich
IlikU
Phillips Petroleum Co.
Polysur Inlenialional
Uniioyal
Hiillips Petroleum Co.
Uniroyul
Nipak
NO. Ol- TOI At
I.ICI-NSI-O NO. Or U.S.
COMUER(!IAL OOUMfUCIAL
U JtMTS' PI AMI'S1
fLANTS1
I
14
U
U
2
S
3
7
39
13
I
I
2
7
U
U
6
12
6
U
U
U
U
I
I
U
U
U
7
N
PLANTS'
(37)
(9)
(7)
(10)
(126)
*U-Al kail uoe plant cxbU, but luul la unknown.
N-Nu touiracrcU |>Uol».
2 PmcQlbeftci UiJicMle lulol autut>ci uf U.S. piuducing pUnu icgjfdku ul* pioccu.
3Soluiiun pulyi
-------
MAJOK UNIT PROCESSES-mtOLYSIS
oo
OTHER
MEQ.UIREO
PROCESSES ,
None
None'
None
None
llalogenalitin
Eslerifcalion
None4
llalogcnalinn
Condensation
llydiohalogenalion
None
Condensation
Condensation
lisieiificalion
PRODUCT
Acetic anhydride
Acetylene
u-Uuiyl acrylale
Cyanuitc acid(2,4.6-Trihydroxy-
1,3,5-lriazine)
Cyanuiic acid, Sodium dichloroisocyanurale.
Tiichloroisucyanuiic acid
Ethyl aceloacelale
Elhylene, Propylene. Hydrogen.
Pyrolysii gasoline
1 Icxachlorocyclopenladienc
Isoprenc
Kelene Juner (Uikclene)
Mulamiue
Melainine
Methyl aceloacelale
FEEDSTOCK
Acetic acid
Hydrocarbons (C,-C,)
Acetic acid
n-Uulyl alcoliol
Uiea
Caustic soda
Chlorine
Urea
Acetic acid
Elhanol
Uulauet, or Propane, or
Ethane, 01 Naphllu
orUasOil
Peulune
Formaldehyde
Hydrogen chloride
Isobuiylene
Aceiic acid
DicyandUmidc
Urea
Aceiic acid
Isopropaiiol
NO. Ol-
ItftNStU
COUUtRCIAL
OWNER 01- PLANT PLANTS'
-
Illili
Wacker-Cheniie
Gulf Oil Chemicals Co.
Shikoku Kasei
Wackcr-Chemie
C. F. Braun
Fluor Corp. (ethane A gas oil only)
Foster Wheeler
Inslilul Francais du Pelrole
M.W. KellogCo.
IJnde AC
Luimnus
Monsanto
Sclas
Stone & Webster
UOP Hioccu Div.
-
Uaycr
Marathon Oil
FMC Corp.
ProduiU Azule
Montedison S.p.A. •
Nissan Chemical lnduslfie«
Wackci-Cheuiie
-
1
N
N
3
U
22
II
U
U
40
100
85
U
U
90
U
-
N
N
2
U
3
1
U
TOTAL NO.
OV U.S.
OlMMEKCIAL
PLANTS*
-
(10)
(5)
(2)
-
(2)
(36)
-
-
-
-
-
-
-
-
-
-
(3)
(6)
-
(2)
(3)
-
-
(1)
U-Al bust one plaul cxuii. bul luul U unktmwit.
N - No CiimuiercLJ pUuU.
fticnlltctti latlkiilc loiul uuutbci ul' U.S. pioduciug ptiuu i
fyiulysU by electric aic.
ul |>ioccix.
-------
MAJOR UNIT HKOCESSES-PYROLYSIS (Continued)
OTHER
REQUIRED
PHOCESSES
None
Condensation
None
Polymerization
None4
None
None
0%
vo
PRODUCT
Naphthalene
Oxalic acid
Phenoihiazine
Polyisocyanale
Propylene (see elhylene)
2.4.6-Trichlorophenol
Vinyl cliloride rnonomei (VCM)
Hydrogen chloride
1 ttUSKX'K
Coal Tar
Petroleum
Sodium Formate
Diphenylamine
Sulfur
Organic dichloridei
Sodium cyanale
Propane, or Butane, or
Naphtha or Gal oils
Tclrachlorobeiuene
Melhanol
Elhylene dichloride
OWNER Ol- PLANT
-
Suuffcr Chemical Co.
Uniroyal
Marathon OU Co.
—
Diamond Shamrock Corp.
UP Goodrich/1 loechil
Kureha Chemical Co.
SolvaylCI
Snuffer Chemical Co.
NO. Ol-'
LICENSED
COMMERCIAL
PLANTS'
-
1
U
N
•-
U
20
1
U
12
TOTAL NO.
Ol U.S.
COMMERCIAL
PLANT'S1
(12)
(7)
(1)
(1)
(61)
(2)
(II)
I —
'U-Al ICMI one ptaiil cxiili, but louJ U unknown,
N - No coiuincf tUl pUiils.
PmcnlheiM indkaie lolul number of U.S. pfoduciiig pUuii icgaiillcu of pio
Pyrolyib by cleciilc arc.
Steam pyrolytis.
-------
TVPK
01-
HEIOHMINi;
MAJOR UNIT PROCESS-REFORMING (STEAM) WATER GAS REACTION
PRODUCT
IttOSIlMK
OWNfH Ol PROCESS
NO 01- TOTAL NO.
I.ICENSEI> OF U.S.
COMMERCIAL COMMERCIAL
PLANTS' PLANTS'
(High pressure)
Melhauol
(High pressure)
(Low pressure)
(Ixiw pressure)
(Low pressure)
(Low pressure)
Melhanol
Media nol
Melliiinol
Melluiuol
Naphtha
Natural gas
Naphtha
Natural Gas
Liquefied I'elroleuni Cias
Melhanol, Diiuelhyl elher Naphtha, Carbon dioxide Vulcan Ciiiciunali
Chemical Coiislruction Co. II
C&I.Girdler U
llaldor Tojiioe U
Imperial Chemical lud. U
M. W. KellogK U
Montedison S.p.A. U
UKW U
Uordeu Client. Co. U
Chemical Construction Corp. U
C & l/Cirdler U
llaldor Topsoc U
Imperial Cliem. Inc. U
M.W. Kclloga U
Lununus 2
Montedison S.p.A. U
Vulcan Cincinnati 13
Imperial Chemical Ind. 20
Lurgi 5
Imperial Chemical Ind. U
Imperial Chemical lud. U
13
(H)
II Al Icui oac plant eiub. but luial b unknuwa.
N-No cuinin«:it;ial ptauls.
rii InJiculo lulu! number of U.S. piojitcuig pbau i
HiMeu of proccu.
-------
MAJOR UNIT HUOCKSSliS SULI'ONATION
GTIIUU
KiJQiiiHi-:i>
pkoci-:ssES
Hydrolysis
Hydrolysis
llydiogciulion
llydiolysis
Hydrolysis
Nuuc
Hydrolysis
liilciificallon
llydiucyuiialiun
Hydrolysis
1 lydrulysis
Hydinlysis
PMGIUICT
Alcohols, lulled linear, sullaiud,
ammonium sail
— , ludiuni sail
-. IriellianoJamiue sail
— , unspecified
Alkylbeiuene sulfonales
MI-AlllillUpllLlllll
tt<---l)u!yl alcoluil
tilliuxyliulfales
Lupropyl alcuhul
Mclliyl niclliacrylale inonuiner
2-Nii|ililliiJ (tf/a-naphlluil)
llicn.il
lUiiDsroci;
Fally ulculiuls, sulfui liiuxldc
i* it
H It
It tt
II II
Alkylkeuzcuci. siilfui Iriuxide
Nitrubcnzcne
Uulylciie
Ulliuxylales, sulfui liitixldc
I'dipylcnc
Acclone
llydrugeucyaalilo
Meilianul
Na|ililliiileiio
Cauilic suda
Bcn/eue
C'auslic soda
Sul In lie acid
UWNI-H Ol- fKUC'tSS
Clieiuithuii
UuUo Kcini AB
Clieuiilhun
Hub
MoOu Kenii AU
Suiuilunio Chcni. Co.
Scientific Dosii-ii/Mara-un Oil Co.
(lieiuilhua
MiiDu Keiui
UP Chemicals, Int.. Lid.
Texacu Oevelupinenl Cuip.
Montedison S.p.A.
Sumitomo Cliein. Co.
Milsui Chcin. Co.
Miuui Qiem. Co.
NO. Ol'
LICI:NSI;I>
tXtMMKMCIAI.
PLANTS'
U
5
U
1
S
(1)
1
U
5
4
U
1
1
U
U
TOTAL
NO. or ii.s.
COMMERCIAL
PLANTS"
(9)
(2)
(4)
(2) '
(0
(10)
-
(0)
M)
—
(5)
(4)
(1)
(1)
U- Al Iciisl one |>kiul caUli. but tulol U unknown.
N No cuiunitiicLil |ifout».
3t*iiicittlii:u:i Jndkatc tuUl uuiitbci of U.S. ptoduciug |>liinU i^^aiJL-u of uiuccu.
-------
6.4.2 Minor Unit Processes
Appendix B presents the definitions for the Minor Unit Processes
Because some of these processes are less well known, a more detailed
description has been included than the descriptions for the Major
Unit Processes. Among these more detailed description are the follow-
ing: (1) the Ashai electrohydrodimerization process for continuous
production of adiponitrile by reductive dimerization of acrylonitrile;
(2) the Daicel process for epoxidation of propylene with peracetic
acid to produce propylene and acetic acid; (3) the Stamicarbon BW
process for production of caprolactam by nitrosation of cyclohexyl-
amine followed by a Beckmann rearrangement of the cyclohexanone oxime
to caprolactam, and (4) the U.S. Industrial Chemicals process for the
production of vinyl acetate by oxyacetylation from ethylene, acetic
acid and oxygen.
6.5 Directory of Companies Owning/Licensing Manufacturing Processes
There are 145 listings in Appendix C of companies, or major
divisions of large companies, who own and/or will license the processes
for the products tabulated in Tables 6.2 and 6.4. The name and
address of each company is given in Appendix C. No reference to
product processss under license is given in this table. This infor-
mation can be taken from Tables 6.2, 6.4 and 6.5 as required for a
specific product or process.
72
-------
Table 6.3 Minor Unit Processes - Summary
Process Compounds Entries to Table
1. Acid Cleavage 2 2
2. Acid Rearrangement 3 3
3. Amination by Reduction 2 2
4. Beckmann Rearrangement 1 2
5. Benzidine Rearrangement 1 1
6. Cannizzaro Reaction 1 1
7. Carboxylation 5 3
8. Chlorohydrination 3 4
9. Dealkylation, (Thermal) 1 1
10. Dealkylation, (Catalytic) 1 1
11. Electrohydrodimerization 1 1
12. Epoxidation 4 3
13. Hydroacetylation 1 1
14. Hydrocyanation 2 2
15. Hydrodealkylation 2 3
16. Isomerization 3 5
17. Nitrosation 1 2
18. Oxyacetylation 1 1
19. Ozonolysis 7 _3
TOTAL 42 42
73
-------
Table 6.4
MINOR UNIT PROCESSES
I-HUUUCT
Acid Cleavage
Oxidation
Alkylalion
Hydrolysis
Oxidation
Acid Rearrangement
llydrogeaalion
Oxidation
Acid Rearrangement
llydrogenalioii
Animation by Reduction
Nitration
Uenudine Rearrangement
Phenol.
Acetone
Phenol
Acetone
«i-Dichlo(obenzene
(1,3-dichlorobcnzene)
p-Aminophcnol
r>-Aminophcnol
3,3'-Dichlurobenzidine
dihydrochloiide
I-T:I:USTOCK
Cumene
Uenzcne
Prouylene
Toluene, Amuiouia
Dichlorobenzeuei
Nitrobenzene
Phenol
I -Chk>ro-2-iiilrobenzene
OWNI R or PROCESS
UP Chemicals Int. Ltd. & Hercules
Rhone Poulenc
UOP Process Division
Allied Chemical
SNIA Viicou
NO Ol TOTAL
IICINShU NO.OI-'U.S.
fOUMlHriAL coMtimriAL
piAMTvl PI ANTS'
PLANTS'
22
5
3
U
(17)
(2)
(2)
(2)
Becknuiun Rearrangement,
Nilrosalion
Oxidation
NilioMalion
Ucn/idiiic Rearraiigemeul,
Arniualiou by Reduction
Canuiizaro Reacliun
Condensation
Carbon ylalion
Bslerificalion
Carboxylalion
Carboxylalion
Chlurohydrinaliuu
Hydrolysis
llalogcnalion.
Hydrolysis
Caprolaclam
Caprolaclam
3,3'-Uiclilorobcn/idine
dibydiocbloiide
Pcnlaeryihrilol
3-llydroxy-2-napluhoic acid
p-Oxybenzoic acid and
f>-Oxybcnzoic bulyrale
Salicylic Acid
Sodium />-amiumjlicylale
bpichlorohydrin
('•lycerine (glycerol)
Cycluhexane
Ammonia, Oleum
Cycluhexanol/cyclohexanone
Ammonia, Oleum
1 -Chloro-2-nilrobcngene
Acclaldehyde
Formaldehyde
Ac/d-Naplilliol. Carbon dioxide
Uulyl alcoliol
Caibun dioxide, Phenol
Hienol, Carbon dioxide. Caustic soda
j/i-Aininophenol, Caustic soda
Ally! chloride
llypochlorousacid
Propylene->allylcldoride->epichloro-
hydiin
Slamicarbon
Inventa AC
Slamicarbon
Zinuiter AG
-
Montedison S.p.A.
Meissner
Sumitomo Chem. Co.
Mitsui Chemical
Mitsui Chemical
Sumitomo Chcm. Co.
Union Carbide
-
13
6
4
4
-
1
U
2
U
1
1
(3)
'
-
(2)
(4)
(4)
-
(1)
(3)
(2)
1U- Al Icjiit uiw plant cnult, bul total is unknown.
N No tuumucrfkil pljuls.
3Kiicnllu;sus inilicutc lolal uuiuUrf of U.S. producing ptinlk icgjiidicu of piu
-------
MINOR UNIT PROCESSES (Continued).
Ln
PHOCESSES
llalogenalion
Hydrolysis
Hydrolysis
Dealkylallon. (Thermal)
Dealkylalioii. (Catalytic)
Eleclrohydrodiinerualian
Epuxidiiliua
llydiolysis
Upoxidalion
llydroacelybtion
llydrocyanalion
tsieril'icalion
llydiolysis
Sulloitiilion
llydrodeafltybliun
HydrudealkyUliou
PKOUUCT
Propylene oxide
Propylcne oxide
Naphthalene
Naphthalene
Adi|>ouiliilc
Epoxidi/ed polybuladiene
(cuicd epoxy polybuladiene)
Glycerine (Glycciol )
Propylene oxide
Acetic iicid
Vinyl acetate
Aciyloniliilc
Methyl mclluciyhle monomei
Beiucne
Benune
I-'EEOSTOUC
Propylene
/fr/ Butyl alcoliol (recycled)
Chlorine
Piopylene
Chlorine solution
Miikoriiuw
Alkylna|4ilhalenes
Alkylnaphlhalenes
Aciylonitiile
Acetic acid,
llydiogen peroxide
Pidybuliidicnc
Ally) alcohol
Pcriicelic acid
Propylcne
JO* Peraceiic acid
10-15% Acetic acid
Acetylene
Acetic acid
Acetylene
1 lyiliugen cyanide
Acetone
llydiugcn cyanide
Mclhaiml
Coke oven light oil
Toluene
OWNER Ol- PKOCESS
Lummui
BASF AC
Hiils/ Bayer
Union Carbide
Miuisanlo
lloudry Div. Air Prod. A Chem.
UOP Pioccss Div.
Asahi (Item. Ind. Co. Ltd.
UCBS.A.
KMC Coip.
Daicel Ltd.
Oaicel Ltd.
Bordcn-Blaw Knox
Scieniilic Design
Wacker-Cheinie
BF Goodrich
Zimmci AG
Monlcdistui S.p.A.
Sumitomo Client. Co.
lloudry Div. Air Prod. & Chem.
British Gas Oil Co.
Gulf K&D Co.
lloudry Div. Air Prod. & Chem.
Moiuanlo
Phillips Petroleum Co.
UOP Process Div.
NO. OF
LICENSED
COMMERCIAL
PLANTS'
N
2
U
3
2
1
U
1)
U
N
4
N
U
8
U
1
2
TOTAL
NO. OF U.S.
COMMI'UCIA
PLANTS1
(0)
(6)
(12)
_
-
(II
(2)
(SI
(4)
-
-
U-At least uuc plant cxuis, bui folbl b uakouwu.
N-- Ma cuiiiincicial pliinii.
PiiienituKs indicate lulal DUiubci ol U.S. piodutdig pliioli legariilesi ul piu
-------
MINOR UNIT PROCESSES (Continued)
a\
CKOCESSES
llydrodcaUtytalkm
llydrodealkyUllon
koiuerizalion
Oxidation
(Catalytic)
(Catalytic with
Beruene
Uciixcuc
Ught llydrocaiboni
I'umaric Acid
Fumarlc Acid
u-Xylene
/>-Xylene
t»-Xylcne
j>-Xylenc
(Catalytic with u-Xylene
non-noble metal) p-Xylcne
Nilroulion Caprolaclam
Ueckinann Rearrangement
Oxidation
Nilrosalion Capiolaclam
Ueckinann Rearrangcmeiil
OxyacclyUlion
Vinyl acetate
OtoiiolytiU Pelaigonlc acid
Oxidation Caproic acid
Auliac acid
Oxidation Pelargnnic acid
Ltndecanoic acid
Tiidecanoic acid
Oxidation Suberic acid
Dodecanoic acid
U-At luul one plant exUu, bul lulal Is unkauwo.
Ft-tiUSTOCK
Xyleiiei (mixed)
Aiuiiialic inixiuia
llydiogcii
Malelc anhydride
Uenzene
Aromatic mix luiei
Xylenes, mixed
Xyleues. mixed
Cyclohexane
Ammonia
Oleum
Cycloliexauol/Cyclohexaiioite
Ammonia
Oleum
lilbylene
Acetic acid
Oxygen
Oils (tall, red, soya bean)
O/oue
O/oue
Cyclic Olefinj
O/one
OWNtK OF fltOCISS
Gulf K&D Co.
lloudiy Div. Ail Prod, t Clieui.
UOH Piuceu Div.
UASF/Veba Ctiemie AC
UiilUli Gas Corp.
Gulf Oil Corp.
lluiidry Div. Air Pruducu it Chem.
llydiucarbun Research Inc./AKCO
UOP Pruceu Uiv.
Alusuisse
ScienliHc Design
Scientific Design
AllanUc-Eii^lliaid Ind.
Turay Ind. Inc -Isoleiie
UOH Pruceu Div.-kumar
Milsubislu Gas Chem. Co.
ICI (Petrochemical Div.)
lavcn la AC
Slainicarbon
Slainicaibon
Zimmer AG
Uayer
National Distillers
Welsbach Corp.
Welibach Corp.
Welsbach Corp.
NO. ()!•
UCENSliD
COUUEROIAI.
PLANTS'
U
2
2
I
>20
U
18
12
>20
2
5
12
2
4
6
13
4
4
8
2
TOTAL
NO. OF U.S.
COMMEHCIAL
PLANTS'
(3)
(4)
S Indkiile luliil uuiubci uf U.S. producing plants icf aitllcu of piuccu.
-------
Table 6.5 INDEX OF
UNIT PROCESSES AND FEEDSTOCKS FOR
MANUFACTURE OF 263 COMMERCIAL ORGANIC CHEMICALS
1.
2.
3.
4.
5.
6.
PRODUCT
Acetaldehyde
Acetaldehyde
Acetic acid
Acetic acid
Acetic acid
Acetic acid
Acetic acid
Acetic acid
Acetic anhydride
Acetic anhydride
Acetone '
Acetone
Acetone
Acetylene
Acetylene
Acetylene
Acetylene
Acetylene
Acrolein
OTHER
PRODUCTS
Hone
None
None
None
Peracetic acid
Terphthallc acid
Methanol
None
None
None
None
Phenol
Phenol
None
None
None
Ethylene
None
Acetaldehyde
Acrylic acid
PROCESSES
Dehydrogenation
Oxidation
Alkylation
Oxidation
Oxidation
Oxidation
Oxidation
Hydrolysis
Carbonylatlon (Oxo)
Condensation
Pyrolysis
Dehydrogenation
Acid cleavage, Alkylation
Hydrolysis, Oxidation
Acid cleavage. Oxidation
Cracking (catalytic)
Cracking (catalytic)
Cracking (catalytic)
Oxidation
Cracking (catalytic)
Pyrolysis by electric
arc
Oxidation
FEEDSTOCK
Ethyl alcohol
Ethylene
n-Butenes
Light naphtha
Acetaldehyde
n-Butane, p-xylene
Methyl acetate
Methanol, carbon monoxide
Acetic acid
Acetic acid
Isopropyl alcohol
Benzene, propylene
Cumene
Methane and by-product
ethylene
Methane
Natural gas
Hydrocarbons (C, -
X
Hydrocarbons (C_ -
Propylene
V
o
cfi)
7. Acrylamide
None
Hydrolysis'
Acrylonitrile
8. Acrylic acid and
Acrylate esters
None
Esterificatlon
Oxidation
Propylene, alcohols
-------
CO
PRODUCT
9. Acrylic resins
10. Acrylonltrlle
Acrylonltrlle
11. Acrylonltrlle-butadlene
styrene resins (ABS resins)
12. Adlplc acid
Adlplc acid
13. Adiponltrlle
Adlponltrlle
Adiponltrlle
14. Alcohols (C7 - C13)
15. Alcohols, mixed, linear
aulfated, ammonium salt
-, sodium salt
-, trlethanolamlne salt
-, unspecified
16. Alkyl benzenes (Branched)
Alkyl benzenes (Linear)
Alkyl benzenes (Linear)
17. Alkylbenzene sulfonates
OTHER
PRODUCTS
None
None
None
None
None
None
None
Hexamethylene dlamlne
None
None
None
None
None
None
None
None
None
None
PROCESSES
Polymerization
Ammoxidatlon
Hydrocyanatlon
Polymerization
Oxidation
Oxidation
Ammoxlilatlon
Halogenatlon
llydrogenatlon
Electrohydrod liner Izatlon
Carbonylatlon(Oxo)
Sulfonatlon
Sulfonatlon
Sulfonatlon
Sulfonatlon
Alkylatlon
A Iky] at Jon
Alkylatlon
Deliydrogena t Ion
Hydrolysis
Sulfonatlon
FEEDSTOCK
Acrylonltrlle
Propylene
Acetylene
Hydrogen cyanide
Acrylonltrlle,
Butadiene, styrene
Cyclohexane
Cyclohexyl alcohol
Adlplc acid
Butadiene
Acrylonltrlle
Mellianol, carbon monoxide
Fatty alcohols, 803
Fatty alcohols, 803
Fatty alcohols, 803
Fatty alcohols, 803
Benzene,
PropyJene tetramer
Benzene, linear oleflns
Benzene, linear paraflns
Alkyl benzenes.
Sulfur Trloxlde
18. Allyl chloride
None
Halogenatlon
Propylene
-------
-J
vo
PRODUCT
19. m-Aminophenol
20. o-Aminophenol
21. p-Aminophenol
OTHER
PRODUCTS
None
None
None
PROCESSES
Hydrogenation
Hydrolysis
Sulfonation
Amlnation by Reduction
Nitration
Acid Rearrangement
llydrogenatlon
FEEDSTOCK
Nitrobenzene
Phenol
Nitrobenzene
22.
23.
24.
25.
26:
Aniline
Aniline
Anthraqulnone
Arsanlllc acid
Azeliac acid
Benzene
Benzene
Benzene
Benzene
Benzene
None
None
None
None
Caprolc acid
Pelargonlc acid
Xylenes
None
None
None
Light hydrocarbons
llydrogenatlon
Anunlnatlon by
Amnonolysls
Oxidation
• Dehydration
Ozonolysis
Oxidation
Alkylation
Hydrodealkylation
Hydrodealkylation
Hydrodealkylation
Hydrodealkylation
Nitrobenzene
Phenol
Anthracene
Aniline, arsenic
Oils (tall, red,
bean)
Toluene
Coke oven light
Toluene
Xylenes (mixed)
Aromatic mixtures
acid
soya
oil
27. Benzenesulfonamitle
None
Amlnation by Ammonolysis Benzenesulfonyl chloride
28. Benzenesulfonyl chloride ' None
29. Benzole acid None
30. Benzonltrile None
Condensation
Oxidation
Ammoxidation
Benzene, chlorosulfonic
acid
Toluene
Toluene
-------
00
o
PRODUCT
31. Benzyl chloride
32. Blphenyl
33. Blsphenol A
34. 1.3-Bls(amlnomethyl)cyclo-
hexane
35. Bromofora
36. Butadiene
Butadiene
Butadiene
37. n-Butyl acetate
38. n-Butyl aerylate
39. n-Butyl alcohol
n-Butyl alcohol
40. sec.-Butyl alcohol
sec.-Butyl alcohol
OTHER
PRODUCTS
None
None
None
None
None
None
None
None
None
None
n-Butyraldehyde
Crotonaldehyde
None
None
PROCESSES
Hulogenation
Condensation
Dehydrogenation
Condensation
•Hydrogenatlon
Halogenatlon
Dehyd rogena tIon
(catalytic)
Dehydrogenatlon
(catalytic)
Dehydrogenatlon
(oxidatlve)
EsterIfication
Pyrolysls
Carbonylatlon(Oxo)
Hydrogenatlon
Condensation
Dehydration
Hydrogenatlon
Hydrolysis
Sulfonatlon
Hydrolysis
FEEDSTOCK
Toluene
Benzene
Acetone, phenol
Isophthalonltrlle
Chloroform, hydrogen
bromide
n-Butane
Butene-1, butene-2
Butene-1, butene-2
Acetic acid, n-butyl
a.lcbhol
Acetic acid, n-butyl
alcohol
Propylene, carbon monoxide
Acetaldehyde
Butylene
Butene-1, butene-2
-------
1
CD
PRODUCT
41. tett.-Butyl alcohol
42. n-Butyl benzyl phthalate
43. p -tert.-Butyl phenol
44. n-Butyraldehyde
n-Butyraldehyde
45. Caprolc acid
46. Caprolactam
Caprolactam
Caprolactam
47. Carbon tctrechlorlde
Carbon tetrachloride
Carbon tetrachloride
OTHER
PRODUCTS
None
None
None
n-Butyl alcohol
Crotonaldehyde
n-Butyl alcohol
Azellac acid
Pelargonlc acid
None
None
None
None .
Perchloroethylene
Perchloroethylene
PROCESSES
Oxidation
Esterlflcatlon
AlkylatIon
Condensation
Dehydration
Hydrogenation
Carbonylatlon
Hydrogenatlon
Oxidation
Ozonolysls
Acid Rearrangement
Uydrogenatlon
Oxidation
Beckman Rearrangement
Nitrosation
Oxidation
Beckman Rearrangement
Nitrosation
Halogenatlon
Halogenation
Halogenation
FEEDSTOCK
leobutane
Benzyl alcohol, n-butyl •
alcohol, phthalic
anhydride
Isobutene, phenol
Acetaldehyde
Propylene, carbon monoxide
Oils (tall, red, soya bean)
Toluene. ammonia
Cyclohexane, ammonia
Ammonia,
Cyclohexanol, cyclohexanone
Carbon dlsulflde
Methane, propane
Propane/propylene
48- Chollne chloride
None
Aminatlon by Ammonolysls
Condensation
Hydrohalogenation
Ethylene oxide,
trlmethyl amine
-------
oo
Ni
PRODUCT
49. Chloral
50. Chloroacetic acid
51. Chlorobenzene, mono
52. p-Chlorobenzene sulfonamide None
53. p-Chloro-m-cresol
54. Chloroform
Chloroform
55. Chloronapthalene
56. o-Chlorophenol
57. Chloropicrin
58. Chloroprene
59. Crotonaldehyde
60. Curaene
61. Cyanuric acid
Cyanurlc acid
OTHER
PRODUCTS
None
None
None
None
None
Chlorome thanes
Methyl chloride
Methylene chloride
None
p -Chlorophenol
None
None
n -Butyl alcohol,
n -Butraldehyde
None
Sodium dichloroiso-
cyanurate, Trichlorolso-
cyanuric acid
None
PROCESSES
llalogenation
Halogenation
Halogenation
Ammination by
Ammonolysis
Halogenatlon
Halogenation
Halogenation
Halogenation
llalogenation
Halogenation
Halogenatlon
Halogenation
Condensation
Dehydration
Hydrogenatlon
Alky la t ion
Halogenation
Pyrolysis
Pyrolysls
FEEDSTOCK
Acetaldehyde
Acetic acid
Benzene
p-Chlorobenzene sulfonyl
chloride
m-Cresol
Methane
Methanol
beta-Uapthol
Phenol
' Picric acid
Butadiene
Acetaldehyde
Benzene
Propylena
Caustic Soda
Chlorine
Urea
Urea
-------
00
u>
PRODUCT
62. Cyclohexane
63. Cyclohexanone •
Cyclohexanone
Cyclohexanone
64. Cyclohexyl alcohol
65. Cyclohexylamlne
Cyclohtxylamina
66. Dl-n-butyl phthalate
67. m-Dlchlorobenzene
m-Dlchlorobenzene
68. o-Dichlorobenzene
69. 3.3'-Dichlorcbenzldine
dlhyUrochloride
70. Dichlorodlphenyl-
trichlo roe thane (DDT)
71. Dichlorophenol
72. 2,4-Dichlorophenoxy
acetic acid (2,4~D)
73. 2-(2,4-Dlchlorpphenoxy)
proplonlc acid (2,4-DP)
OTHER
PRODUCTS
None
None
Cyclohexyl alcohol
None
Cyclohexanone
None
None
None
None
None
p-Dlchlorobenzene
None
None
None
None
None
74. 4>4'-Dlchlorophenylsul£one None
PROCESSES
Hydrogenatlon
Dehydrogenatlon
Oxidation
Hydrogcnation
Oxidation
Hydrogenatlon
Hydrogenatlon
Esterification
Acid Rearrangement
Halogenation
Halogenatlon
Benzldine Rearrangement,
Amination by Reduction
Condensation
Halogenatlon
Halogenatlon
Condensation
Halogenatlon
Condensation
Dehydrohalogenation
Condensation
FEEDSTOCK
Benzene
Cyclohexane-Cylohexanol
mixtures
Cyclohexane
Phenol
Cyclohexane
Aniline
Nitrobenzene
n-Butyl alcohol, phthallc
anhydride
Dichlorobenzcnes
Benzene
Benzene
l-Chloro-2-nitrobenzene
Acetaldehyde
Monochlorobenzene
4-Chlorophenol, phenol
Monochloroacetic acid
Phenol
a-Chloroproplonlc acid
2,4-Dichlorophenol
Monochlorobenzete,
Sulfur trioxlde
-------
00
PRODUCT
75. 1.2-Dichloropropane
76. 1,3-Dichloropropane
77. Diechyl phthalate
78. Dlheptyl phthalate
79. Diisodecyl phthalate
80. Dlmethylforuamide
81. Dimethyl phthalate
82. Dimethyl terephthalate
Dimethyl terephthalate
83. 4,6-Dinitro-o-cresol
84. 2,4-Dinltrophenol
85. 2,4-Dlnitrotoluene
2,4-Dinltrotoluene
86. Dl-n-octyl phthalate
87. Dloctyl phthalate
(2-ethylhexyl phthalate)
OTHER
PRODUCTS
None
None
None
None
Hone
None
None
None
None
None
None
None
2,6-Dlnitrotoluene
None
None
PROCESSES
Halogenatlon
Halogenatlon
Esteriflcatlon
Esterlflcatlon
Esterlfication
Amination by Ammonolysis
Eeterification
Esteriflcatlon
Esterificatlon
Oxidation
Nitration
Nitration
Nitration
Nitration
Esterlficatlon
Esteriflcatlon
FEEDSTOCK
Propylene
Allyl chloride
Ethyl alcohol, phthallc
anhydride
Heptyl alcohol, phthallc
anhydride
laodecyl alcohol, phthallc
anhydride
Diraethylamlne, methyl
formate
Methyl alcohol,
phthalic anhydride
Methyl alcohol,
Terephthalic acid
Methyl alcohol,
pi-Xylene
Cresol
Phenol
Toluene
Toluene
alcohol,
Phthalic anhydride
2-Ethylhexyl alcohol,
Phthalic anhydride
-------
oo
Ln
OTHER
PRODUCT PRODUCTS
88. Dlphenylamlne None
89. Diphenylguanldlne None
90. N,N-Diphenylhydrazine None
(Hydrazobenzene)
91. Dlphenylmethane-4,41- None
dliaocyanate (MDI)
92. Dodecanolc acid Suberic acid
93. Dodecene, non-linear None
(Propylene tetramer)
94. Eplchlorohydrin None
95. Epoxy resins None
96. Ethanolamines None
97. Ethoxysulfates None
98. Ethyl acetate None
Ethyl acetate None
99. Ethyl acetoacetate None
PROCESSES
Condensation
Condensation
Condensation
llydrogenatlon
Phosgenatlon
Oxidation
Ozonolysls
Polymerization
FEEDSTOCK
Aniline
Aniline
Cyanic acid
Nitrobenzene
Aniline,
Formaldehyde,
Phosgene
Cylcic oleflns
•Propylene
Chlorohydrluation
Hydrolysis
Polymerization
Amlnation by Aminolysis
Sulfonation
Condensation
Esterlflcation
Esteriflcation
Pyrolysls
Allyl chloride,
Hypochlorous acid
Blsphenol A,
Eplchlorohydrin
Ethylene oxide
Ethoxylates, sulfur
trloxide
Acetaldehyde .
Acetic acid, ethyl alcohol
Acetic acid,
Ethyl alcohol
-------
CO
-------
OO
PRODUCT
112. Ethylene glycol
monomethyl ether
113. Ethylene oxide
Ethylene oxide
114. Ethylene-propylene
Copolyroers (EPM)
115. Ethylene-propylene
Terpolymer (EPT)
116. Ethylene-vlnyl acetate
copolymer resins
117. Ethyl ether
118. 2-Ethyl hexanol
2-Ethyl hexanol
119. Ethyl parathlon
120. Fluorocarbons
Fluorocarbons
OTHER
PRODUCTS
None
None
Ethylene glycol
None
None
None
None
None
n-Butyl alcohol
Isobutyraldehyde
Isobutyl alcohol
None
None
None
PROCESSES
Condensation
Oxidation
Hydrolysis
Oxidation
Polymerization
Polymerization
Polymerization
Dehydration
Condensation
Hydrogenatlon
Carbonylatlon (Oxp)
Hydrogenatlon
Condensation
Halogenatlon
Halogenatlon
Halogenatlon
FEEDSTOCK
Ethylene oxide, ethanol
Ethylene
Ethylene
Ethylene, propylene
Ethylene,
Propylene
Ethylene,
Vinyl acetate
Ethyl alcohol
Acetaldchyde
Butyraldehyde
Propylene
Carbon monoxide
0,0-Dimethyl
Phosphonothionochloridate,
Sodium nltrophenoxide
Carbon tetrachloride,
Hydrofluoric acid
Methane,
Hydrofluoric acid
-------
PRODUCT
121. Formic acid
Formic acid
122. Formaldehyde
Formaldehyde
Formaldehyde
123. Formic acid
124. Fumaric acid
Fumarlc acid
CO
00
125. Glycerine
Glycerine
Glycerine
126. Heptanes
OTHER
PRODUCTS
Sodium Formate
None
None
None
None
None
None
None
None •
None
None
None
PROCESSES
Carbonylatlon (Oxo)
Hydrolysis
Carbonylatlon (Oxo)
Condensation
Hydrolysis
Oxidation ^ ^
Oxidation^2'
Oxidation (2)
Oxidation
laomerizatlon
Isofflurization
Oxidation
ChlorohydrlnaClon
Halogenatlon
Hydrolysis
Epoxldatlon
Hydrolysis
Oxidation
Condensation
FEEDSTOCK
Carbon monoxide.
Sodium hydroxide
Carbon monoxide,
(Methanol recycled)
Methanol
Methanol
Dimethyl ether
Light hydrocarbons
Halelc anhydride
Benzene
Propylene+allyl- chloride-*-
epichlorohydrin
Allyl alcohol.
Peraeetic acid
Propylene
Butylenes
Propylene
(1) Silver catalyst
(2) Metal oxide catalyst
-------
CO
PRODUCT
127. Hexachlorobenzene
128. Hexachlorobutadlene
129. Hexachlorocyclopentadlene
130. Hexachloroethane
131. Hexamethylenedlaralne
llexame thy lened lamlne
Hexamethylenediamlne
132. llexaaethylenetetraalne
90. Hydrazobenzene
(N.N'-dlphenylhydrazlne)
133. Hydrogen cyanide
134. 3-llydroxy-2.-
naptholc acid
135. a-Isoamylene
136. Isobutyl alcohol
laobutyl alcohol
137. laobutylene
OTHER
PRODUCTS
None
None
None
None
None
None
None
None
None
None
None
None
n-Butyl alcohol
2-Ethyl hexanol
laobutyraldeliyde
None
PROCESSES
llalogenatlon
Halogenation
Pyrolyala
llalogenatlon
Amlnatlon by Ammonolyale
Anunoxldatlon
Hydrogenatlon
Condensation
Dehydration
Condenaatlon
Hydrogenatlon
Ammoxldatlon
Carboxylatlon
Dehydrogenatlon
Carbonylatlon (Oxo)
Hydrogenatlon
Carbonylatlon (Oxo)
Hydrogenatlon
FEEDSTOCK
Benzene
Butadiene
Pentane
Tetrachloroethane
Adlplc acid
Adlplc acid
Adlponltrlle
Ammonia
Formaldehyde
Nitrobenzene
Methane
beta-Napthol(
Carbon dioxide
Isopentane
Propylene
Carbon Monoxide
Propylene
Carbon monoxide
None
Cracking, catalytic
leobutane
(1)
Listed under N.N'-diphenylhydrazlne aa No. 90
-------
PRODUCT
138. Isobutyraldehyde
139. Isophthalic acid
140. Isophthalonttrlle
141. Isophorone
142. Isoprene
laoprene
Isoprene
Isoprene
Isoprene
Isoprene
Isoprene
Isoprene
Isoprene
Isoprene
143. Isopropyl acetate
Isopropyl alcohol
Isopropyl alcohol
OTHER
PRODUCTS
n-Butyl alcohol
Isobutyl alcohol
2-Ethyl hexanol
None
None
None
None
None
None
None
None
None
None
None
None
None
None
None
None
PROCESSES
Carbonylatlon (Oxo)
Kydrogenation
Oxidation
Ammoxidation
•Condensation
Condensation
Condensation
Dehydration
Condensation
Dehydration
Condensation
Hydrohalogenation
Pyrolysis
Condensation
Cracking, catalytic
Dehydrogenation
Cracking, catalytic
Cracking, catalytic
Cracking, catalytic
Dehydrogenation
Esterification
Hydrolysis
Sulfonatlon
Hydrolysis'1)
FEEDSTOCK
Propylene,
Carbon monoxide
m-Xylene
m-Xylene
Acetone
Propylene
Acetone,
Acetylene
Formaldehyde,
Isobutylene
Formaldehyde,
Isobutylene,
Hydrogen chloride
Isobutylene
Methanol
tert.-Amylenes
Isobutylene,'
Formaldehyde
Propylene
Ainylenes
Isopentane
Acetic acid,
Isopropyl alcohol
Propylene
Propylene
(1) Direct catalytic hydrolysis
-------
144.
145.
146.
147.
148.
149.
150.
151.
152.
153.
PRODUCT
N-I sopropy 1-N-phenyl-p-
pheny lened lamine
Ketene dimer
Lead alkyls
Maleic acid
Malelc anhydride
Maleic anhydride
Malelc anhydride
Melamine
Melamine
Mesltyl oxide
DL-Methionine
Methyl acetate
Methyl acetoacetate
OTHER
PRODUCTS
None
None
None
None
None
None
None •
None
None
None
None
None
None
PROCESSES
Alkylation*1*
Dehydrohalogenatlon
llydrogenatlon
Pyrolysls
Alkylation
Hydrolysis
Dehydration
Oxidation
Dehydration
Oxidation
Dehydration
Oxidation
Condensation
Pyrolysis
Condensation
Pyrolysls
Condensation
Dehydration
Condensation
Hydrogenation
Esterification
Esterificatlon
Pyrolysls
FEEDSTOCK
Acetone,
Aniline,
p-Chloro-nitrobenzene
Acetic acid
Ethyl chloride,
Alkyl chlorides
Maleic anhydride
Butadiene (plus other €4
hydrocarbons)
Benzene
Butene-1, Butene-2,
Butadiene (if present)
DicyandianJ.de
Urea .
Acetone
Acrolein,
Cyanic acid,
Methyl me reap tan
Acetic acid
Methyl alcohol
Acetic acid.
Isopropyl alcohol
(1) Reductive alkylation
-------
N>
PRODUCT
154. Methyl alcohol
Methyl alcohol
Methyl alcohol
Methyl alcohol
Methyl alcohol
Methyl alcohol
155. Methylamlnes
156. Methyl bromide
15 7. 2-Methyl-2-butanol
(tert-Amyl alcohol)
158. 2-Methyl-3-butyn-2-ol
159• Methyl chloride
Methyl chloride
Methyl chloride
160. 2-Methyl-4-chloro-
phenoxyacetic acid (MCPA)
161. 2-(2-Methyl-4-chlorophenoxy)
proplonlc acid (MCPP)
162. Methylene chloride
Methylene chloride
Methylene chloride
163. Methyl ether
(1) High pressure
(2) Lou pressure
OTHER
PRODUCTS
None
None
None
None
None
Methyl ether
None
None
None
None
None
None
None
None
None
Chloroform
Methyl chloride
Chloroform
Methyl chloride
Chloroform
Methyl chloride
Methyl alcohol
PROCESSES
Reforming (Steam)(!)
Reforming (Steam)t1'
Reforming (Steam)(2)
Reforming (Steam)'2'
Reforming (Steam)(2)
Reforming (Steam)(2)
Amlnation by Anmonolysis
Hydrohalogenation
Condensation
Hydrogenatlon
Condensation
Halogenation
Halogenation
Hydrohalogenation
Condensation
Halogenation
Condensation
Dehydrohalogenation
Halogenation
Halogenation
Halogenation
Reforming (Steam)
FEEDSTOCK
Naphtha
Natural gas
Naphtha
Natural gas
Liquefied
petroleum gas
Naphtha, carbon dioxide
Methanol, ammonia
Methanol
Acetone,
Acetylene
Acetone,
Acetylene
Methanol
Methane
Methanol
o-Cresol
Monochloroacetic acid
a-Chloropropionic
acid, 4-chloro-o-cresol
Methyl alcohol
Methane
Methane and methyl
alcohol
Naphtha
-------
vO
U)
PRODUCT
164. Methyl ethyl ketone
Methyl ethyl ketone
165. 2-Methyl-5-ethyl pyrldlne
(HEP)
166. Methyl Isobutyl ketone
167. Methyl methacrylate
Methyl methacrylate
monomer
163. Methyl parathlon
169. 4-Methyl-l-pentene
170. Monochloroacetic acid
171. Morphollne
172. Naphthalene
Naphthalene
Naphthalene
173. 2-Naphthol
OTHER
PRODUCTS
None
None
None
None
None
None
None
None
None
None
None
None
None
None
PROCESSES
Dehydrogenatlon
Hydrolysis
Dehydrogenation
Condensation
Dehydration
Condensation
Dehydration
Hy d rogena t Ion
Esteri£ication
Hydrocyanation-
Hydrolysis
Sulfonatlon
Esterificatlon
Oxidation
Condensation
llalogenatlon
Condensation
Halogenation
Dehydration
Pyrolysls
Dealkylation, thermal
Dealkylation, catalytic
Hydrolysis
Sulfonatlon
FEEDSTOCK
Butene-1,
Butene-2
eec. -Butyl alcohol
Acetaldehyde ,
Ammonia
Acetone,
Hydrogen
Acetone,
Hydrogen cyanide,
Methyl alcohol
Isobutylene,
Methyl alcohol
0,0-Dimethyl phosphoro-
thlonochlcridate, sodium
p -nl t rophenoxide
Propylene
Acetic Acid
Dlethanolamine
Coal tar, or petroleum
Alkyl naphthalenes
AlUyl naphthalenes
Naphthalene
174. Nitrobenzene
None
Nitration
Benzene
-------
PRODUCT
175. o-Nitrophenol
176. p-Nltrophenol
177. m-Nltro toluene
178. o-Nitrotoluene
179. P-Microtoluene
180. p-Nonyl phenol
181. Oxalic acid
182. p-Oxybenzoic
acid
183. Pelargonlc acid
Pelargonic acid
164. Pentachlorophanol
Pentachlorophenol'
185. Pentaerythritol
166. Perchloroethylene
Perchloroethylene
Perchloroethylene
OTHER
PRODUCTS
None
None
None
None
None
None
None
p -Oxybenzolc
butyrate
Azellac acid
Caproic acid
Undacanolc acid
Tridecanolc acid
None
None
None
PROCESSES
Nitration
Nitration
Nitration
Nitration
Nitration
Alkylatlon
Condensation
Pyrolysis
Carboxylation
Esteriflcatipn
Oxidation
Ozonolysls
Oxidation
Ozonolysis
Halogenatlon
Hydrolysis
Cannizzaro Reaction
Condensation
FEEDSTOCK
Phenol
Phenol
Toluene
Toluene
Toluene
Phenol
.Propylene trlmer
Sodium formate
Butyl alcohol,
Carbon dioxide.,
Phenol
Oils (Tall, red soya
bean).
alpha-Olefina
Phenol
Hexachlorobenzene
Acetaldehyde,
Formaldehyde
Trichloroethylene
Trlchloroethylene
Trichloroethylene
Cracking, catalytic
Halogenatlon
Cracking, catalytic
Halogenation
Cracking, catalytic
Halogenation
Oxyhalogena tIon
Ethylene dlchlorlde
Acetylene
Any C0 chlorocarbon
mixture
-------
PRODUCT
189. Phenol
Phenol
Phenol
Phenol
Phenol
Phenol
190. Phenothiazine
191. N-phenyl-2-naphthylanine
vo
in 192. p-Phenylphenol
193. Phosgene
19 A. Phthallc anhydride
Phthallc anhydride
195. Phthalonitrlle
196. beta-Plcollne
197. Plperylene
198. Polyarclde resins
OTHER
PRODUCTS
Acetone
Acetone
Hydrogen
None
None
None
None
None '
None
None
None
None
None
Pyrldlne
None
None
PROCESSES
Acid cleavage
Alkylation
Hydrolysis
Oxidation
A'cld cleavage
Oxidation
Dehydrogenation
Oxidation
.Hydrolysis
Hydrolysis
Sulfonation
Hydrolysis
Oxyhalogenatlon
Pyrolysis
Dehydration
Condensation
•Dehydrogenation
Halogenation
Oxidation
Oxidation
Ammoxidation
Ammoxidation
Condensation
Dehydrogenation
Polymerization
FEEDSTOCK
Benzene, propylene
Cumene
Cyclohexane
Monochlorobenzene
Benzene, sulfuric acid
Benzene,
Hydrogen chloride
Diphenylamine, sulfur
Aniline, 2-naphthol
Benzene, cyclohexanone
Carbon monoxide,
Chlorine
Naphthalene
o-Xylene
o-Xylene
Acetaldehyde,
Formaldehyde, methanol
n-Pentene
Caprolactara
(Nylon 6)
199. Polyamide resins
(Nylon 66)
None
Polymerization
Adipic acid,
hexauethylene diamlne
-------
PRODUCT
OTHER
PRODUCTS
(1)
V0
ON
198. cis-l,4-Polybutadlene
'199. Polybutadiene*2*
Polybutadlene^1)
200. Polybutadlene-acrv-
lonltrile (NBR)(2>
201. Polybutadlene, epoxidized
202. Polybutenes
203. Polycarbonate resins
204. Polychloroprene
205. Polyester resins,
Saturated
206. Polyester resins,
Unsaturated
20J. Polyether glycols
Polyether glycols
None
None
None
None
None
None
None
None
None
Hone
None
None
PROCESSES
Polymerization
Polymerization
Polymerization
Polymerization
Epoxldatlon
Polymerization
Dehydrohalogenation
Phosgenation
Polymerization
Polymerization
Polymerization
Polymerization
Polymerization
Polymerization
FEEDSTOCK
Butadiene
Butadiene
Butadiene
Acrylonitrile,
Butadiene
Acetic acid,
Hydrogen peroxide.
Polybutadiene
Butene-1, butene-2
Bisphenol-A, methylene
chloride, phosgene
Chloroprene
Glycols,
Polybaslc acids,
Styrene
Glycols, styrene,
unsaturated dibasic
acids
Ethylene oxide,
Propylene oxide
Alcohols,
Ethylene oxide,
Propylene oxide
(1) Solution polymerization
(2) Emulsion polymerization
-------
PRODUCT
208. Polyethylene
(low density)
209. Polyethylene
(high density)
210. Polyethylene terephthalate
Polyethylene terephthalate
211. Polylsobutylene
212. Polylsocyanate
213. cis-Polylsoprene (IR)(l>
214 . Polypropylene-
215. Polystyrene
216 . Polystrens (High impact-
rubber modified) (!)
217 . Polyylnyl acetate
218. Polyvinyl alcohol resins
219. Polyvinyl chloride resins
220. Polyvinyl chloride-
acetate copclymer
OTHER
PRODUCTS
None
None
PROCESSES
Polymerization
Polymerization
FEEDSTOCK.
Ethylene
Ethylene
None
None
None
None
None
None
None
None
None
None
None
None
Condensation
Polymerization
Esterification
Polymerization
Polymerization
Polymerization
Pyrolysls
Polymerization
Polymerization
Polymerization
Polymerization
Polymerization
Polymerization
Polymerization
Polymerization
Dimethyl terephthalate
ethylene glycol
Ethylene glycol,
Terephthallc acid
Isobutylene, bucenes
Organic dichlorides,
Sodium cyanate
Isoprene
Propylene
Styrene
Polybutadlene, sty rone
Vinyl acetate
Vinyl alcohol
Vinyl chloride
Vinyl acetate, vinyl
chloride
Suspension polymerization
-------
oo
PRODUCT
221. Polyvlnyl chlorlde-
vlnylidene chloride resina
222. beta-Proplolactone
22 3. Propylene
Propylene
224. Propylene carbonate
225. Propylene glycol
226. Propylene oxide
Propylene oxide
Propylene oxide
OTHER
PRODUCTS
(1)
(93.) Propylene tetramer
(Dodecene)
22 7. Pyrldlne
228. Pyromellitlc dianhydrlde
229. salicylic acid
None
None
None
None
None
None
None.
Acetic acid
None
None
beta-Picollne
None
None
PROCESSES
Polymerization
Polymerization
Dehydrogenation
Pyrolysis
Condensation
Hydrolysis
Chlorohydrination
Halogenation
Hydrolysis
Epoxidatlon
Chlorhydrinatlon
Hydrolysis
Polymerizaclon
Amiuoxldatlon
Condensation
Alkylatlon
Oxidation
Carboxylation
FEEDSTOCK
Vinyl chloride,
Vinylldene chloride
Formaldehyde, ketene
Propane
Butane, or gas
oils, or naphtha,
or propane
Carbon dioxide
Propylene oxide
Propylene oxide
Propylene,
Chlorine solution
tert. Butyl alcohol
(recycled)
Propylene,
30% Peracetic acid,
10-15% Acetic acid
Propylene,
Chlorine solution,
milk of lime
Propylene
Acetaldehyde,
Formaldehyde,
Methanol
1,2,4-TrimethyJbenzene
(Psuedocumene)
Phenol, carbon dioxide,
caustic soda
(1) Listed under Dodecene as No. 93
-------
VO
PRODUCT
230. SBR (Polybutadlene-
styrene)^'
SBR (Polybutadlene-
OTHER
PRODUCTS
231. Sodium p-amino-
ealicylate
232. Sodium formate
233. Sorbitol
234. Styrene
Styrene
235. Suberic acid
23'6. Terephthalic acid
23 7. Terephthalonitrlle
238. 1,1,2,2-Tetrachloroethane
239. Tetrahydrofuran, 2,3,4,5-
tetracarboxylic dianhydride
240. Tetramethylthiuram
dlsulflde (Thiram)
(L) Emulsion polymerization
(2) Solution polymerization
None
None
None
None
None
PROCESSES
Polymerization
Polymerization
Carboxylatlon
Carbonylation<°*°)
Hydrogenation
None
None
Dodecanolc acid
None
None
None
None
None
Alky la t ion
' Dehydrogenatlon
Dehydrogenation
Oxidation
Ozonolysls
Oxidation
Ammoxidation
Halogenation
Condensation
Oxidation
Condensation
Oxidation
FEEDSTOCK
Butadiene
Styrene
Butadiene
Styrene
nj-Aminophenol, carbon
dioxide, caustic soda
Carbon monoxide,
Sodium hydroxide
Corn sugar, or corn
syrup
Benzene, ethylene
Ethylbenzene
Cylcic oletins
p-Xylene
p-Xylene
Ethane
Furan, maleic anhydride
•Ammonia, carbon dlsulfide,
dimethylamlne, hydro-
gen peroxide
-------
o
o
PRODUCT
241. Toluene dtisocyanate
(TDI) (80/20-2,4-2,6-TDI)
242. Trlacetln polymer
243. Tributyrin (glyceryl
tributyrate)
244. 1,2,4-Trlchlorobenzene
245. 1,1,1-Trlchloroethane
1,1,1-Trlchloroethane
246. 1,1,2-Trichloroethane
247. Trichloroethylene
Trlchloroethylene
Trichloroethylene
248. 2,4,6-Trichlorophenol
-2,4,6-Trichlorophenol
249. 2,4,5-Trlchlorophenoxy-
acetlc acid (2,4,5-T)
250. Tridecanolc acid
OTHER
PRODUCTS
None
None
None
None
None
None
None
Perchloroethylene
Perchloroethylene
Perchloroethylene
None
None
None
Pelargonic acid
Undecanolc ar.1d
PROCESSES
Hydrogenatlon
Nitration
Phosgenatlon
Esterificatlon
Esterlficatlon
Halogenatlon
Halogenation
Halogenation
Hydrohalogenatlon
Halogenation
Cracking, catalytic
Halogenatlon
Cracking, catalytic
Halogenation
Cracking, catalytic
Halogenation
Oxyhalogenation
Halogenatlon
Pyrolysis
Condensation
Halogenation
Oxidation
Ozonolysis
FEEDSTOCK
Phosgene,
Toluene
Acetic acid, cellulose•
n-Butyric acid,
Clycerol
1,2-Dichlorobenzene
Ethylene, '
Vinyl chloride
Ethylene
Ethylene dlchloride
Acetylene
Any Cy chlorocarbon
mixture
Phenol
Tetrachlorobenzene,
Methanol
Acetic acid ,
Trichlorophenol
o-Olefina
-------
PRODUCT
251. Trlmellittc
anhydride
272.. Undecanolc acid
253. Urea
254. Urea-formaldehyde resins
255. Vinyl acetate
Vinyl acetate
256. Vinyl chloride
monomer (VCM)
Vinyl chloride
monomer (VCM)
Vinyl chloride
monomer (VCM)
Vinyl chloride
monomer (VCM)
Vinyl chloride
monomer (VCM)
Vinyl chloride
monomer ([VCM)
Vinyl chloride
OTHER
PRODUCTS
None
Pelargonic acid
Tridecanoic acid
None
None
None
None
Hydrogen chloride
None
None
None
None
No.ne
Hydrogen chloride
PROCESSES
Oxidation
Oxidation
Ozonolyala
Aminatlon by Ammonolyuls
Dehydration
Polymerization
Hydroacetylation
Oxyacetylation
Cracking, catalytic
Cracking, catalytic
Halogenatlon
Oxyhnlogenation
Cracking, catalytic
Dehydrohalogenation
Halogenation
Oxyhalogenation
Cracking, catalytic
Halogenatlon
Cracking, catalytic
Halogenation
Cracking, catalytic
Dehydrohalogenation
Halogenation
Oxyhalogenatlon
Pyrolysle
FEEDSTOCK
Pseudocumene
a-Oleflna
Carbon dioxide
Biuret, formaldehyde,
urea
Acetylene
Acetic acid
Ethylene, acetic
acid, oxygen
Ethylene dichlorlde
Ethylene
Ethane
Acetylene
Ethylene
Naphtha
Ethylene dichlorlde
-------
o
K>
PRODUCT
236. Vinyl chloride
monomer (VCM)
Vinyl chloride
ramomer (VCM)
257. Vinyltdcne chloride
Vinylidene chloride
258. o-Xylen.^1*
o-Xylene(2)
o-Xylene<3>
25'J. Xylenes,
mixed
.260. m-Xylenediamine
261. 2,4-Xylenol
262. Zlneb
263. Ziram
OTHER
PROnUCTS
None
None
None
None
p-Xylene
p-Xylene
p-Xylene
None
None
None
None
PROCESSES
Cracking, thermal
Halogenatlon
Ojcyhalogenation
liydrohalogenatlon
Dehydrohalogenatlon
Halogenatlon
Isomerization
Isomerization
Isomerization
Dehydrogenation
Hydrogenatlon
Alkylation
Condensation
Dehydration
Condensation
Dehydration
FEEDSTOCK
Ethylene
Acetylene
1,2-Mchloroethane
Ethylene
Aromatic mixtures
Xylenes, mixed .
Xylenes, mixed
Naphtha
Isophthalonitrlle
p-Cresol, methyl
chloride
Ammonia, carbon di-
sulflde, ethylene-
diamine
Ammonia, carbon di-
sulflde, dimethylamlne
(1) Catalytic Isomerization
(2) Catalytic Isomerization with HF-BF3
(3) Catalytic Isomerization with non-noble metal
-------
BIBLIOGRAPHY
Allinger, N.L., et al. Organic Chemistry, Worth Publishers, Inc.
New York, N.Y., 1971.
Chemical Engineering. Sources and Production Economics of Chemical
Products. McGraw Hill, Inc., New York, N.Y., 1974.
95th Congress, 1st Session. (95-30) Data Relating to H.R. 3199 (Clean
Water Act of 1977) U.S. Government Printing Office, Wash., D.C.,
November, 1977.
Consent Decree - Natural Resources Defense Council vs. Train. 8 ERC
2120-8 ERC 2136. U.S. District Court, District of Columbia.
Earhart, J.P., et al., Extraction of Chemical Pollutants from
Industrial Wastewaters with Volatile Solvents. Departinent of Chemical
Engineering, University of California, EPA-600/2-76-220 for Robert S.
Kerr Environmental Research Laboratory, Office of Research and
Development, U.S. Environmental Protection Agency. Berkley, CA.,
December, 1976.
Federal Register 42 (197), Part IV, October 12, 1977.
Fieser, L.F. and Fieser, Mary. Advanced Organic Chemistry. Reinhold
Publishing Corp., New York, N.Y., 1961.
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Production and Toxicity of Selected Organic Chemicals. Rev. 1,
Appendices I, II, III, IV, The MITRE Corp., Contract No. 68-02-1495
for the U.S. Environmental Protection Agency. September-October 1976.
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Gruse, W. F. and Stevens, D. R. Chemical Technology of Petroleum. .
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89-200, 1973.
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115-242, 1977.
103
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APPENDIX A
Definitions of
Major Unit Processes
-------
Apendix A Major Unit Processes
1. ALKILATION
Alkylation is the introduction of an alkyl radical by substitu-
tion or addition into an organic compound. There are six general types
of alkylation depending on the linkage which is attacked:
1. Substitution for hydrogen in carbon compound. When an aromatic
hydrogen is substituted this is considered nuclear alkylation.
Since the carbon of the alkyl is bound to carbon of either
aliphatic or aromatic compounds it is also termed carbon-to-
carbon alkylation.
Most of the examples in the table of alkylations are of this
type. Linear alkyl benzenes are made by using ct-olefins or
paraffin halides to alkylate benzene through a Friedel-Crafts
type of alkylation employing hydrofluoric acid, or aluminum
fluoride, as catalyst. The predominant route to the eight
billion pounds of styrene produced annually is via ethyl-
benzene, which is made by alkylation of benzene with ethylene.
Subsequent dehydration to styrene takes place over either
an aluminum chloride catalyst, solid phosphoric acid, or
silica alumina. Cumene is produced by the alkylation of
benzene with propylene over a phosphoric acid catalyst in
the vapor phase at 250°C and 100 psia.
2. Substitution for hydrogen attached to nitrogen. The alkyl
group is bound to a trivalent nitrogen. An example in the
A-l
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alkylation table is the reductive alkylation with acetone in the
presence of hydrogen and a catalyst to form N-isopropyl-N'-phenyl-
p-phenylenediamine.
3. Alkyl-metallic compounds. The alkyl group is bound to the
metal: An example in the alkylation table is lead alkyls,
representing such compounds as tetraethyl lead which is
prepared by the alkylation of a lead, sodium alloy with ethyl
chloride at 65-75°C and 50-65 p.s.i.
The other types of alkylation of less commercial interest are:
4. Substitution for hydrogen in the hydroxyl group of an al-
cohol, phenol or acid, thus bonding the alkyl group to oxygen.
An unusual example of the substitution in an acid is the
Bayer AG acetic acid process. n-Butenes are converted to
sec-butyl acetate with recycled acetic acid in a reactor
cascade in the liquid phase at 100-120°C and 225-375 psi.
The catalyst used is an ion-exchange resin and is suspended
in the reaction mixture. No commercial plants have been
built.
5. Addition of an alkyl halide or an alkyl ester to a tertiary
nitrogen compound. The alkyl bonds to the nitrogen atom,
which in the final product possesses four ordinary covalencies
and one electrostatic bond.
6. Miscellaneous alkylations. In mercaptans the alkyl group is
bound to sulfur and in alkyl silanes, it is bound to silicon.
A-2
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4. Multiple activity, in which nascent or recycled amines
compete with ammonia as a coreactant resulting in the forma-
mation of secondary and tertiary amines by aminolysis. This
occurs in the formation of both methyl amines and ethyl amines,
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2. AMINATION BY AMMONOLYSIS
Amination by ammonolysis is the process of forming amines by
the action of ammonia. The use of primary and secondary amines as
aminating agent (aminolysis) is also included. Consideration is also
given to hydroammonolysis with ammonia-hydrogen mixtures in the pre-
sence of a hydrogenation catalyst. This technique permits the direct
preparation of amines from carbonyl compounds, which with ammonia
alone would result in the preponderant formation of nitriles or
aldimines.
The ammonolytic reactions may involve the following:
1. Double decomposition, in which the NH3 molecule is split
into - NH2 and -H fragments, the former becoming part of the
newly formed amine while the latter unites with the radical
-Cl, -SO^H, or-N02. Examples in the amlnation table are:
aniline and hydrochloric acid from phenol, benzene sulfonamide
and hydrochloric acid from benzene sulfonyl chloride, and ethylene
diamine from ethylene.
2. Dehydration, in which ammonia serves as a dehydrant, and water
and amines result from the ammonolysis of alcohols and from
the hydroammonolysis of carbonyl compounds. Examples from
the amination table include ethyl-amines and methylamines.
3. Simple addition, in which both fragments of the ammonia
molecule enter into the new compound. An example in our
amination table is the formation of ethanolamines from
ethylene oxide and ammonia.
A-4
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3. AMMOXIDATION
Anmoxidation is a process for the formation of nitriles by the
action of ammonia in the presence of air, or oxygen, on olefins, or-
ganic acids or the alkyl group of alkylated aromatics: Amines may be
produced by hydrogenation of the nitriles.
The ammoxidation table shows the manufacture of acrylonitrile by
propylene ammoxidation in a fluidized bed reactor operating at 5-30
psig and 750-950 F. A very active catalyst such as solid antimony
uranium oxide is used. Another example is the ammoxidation of
adipic acid, or butadiene,to adiponitrile, which may be further
hydrogenated to hexamethylene diamine.
In a more unusual reaction methane is ammoxidated at 20-25 psi
and 1030-1090°C to form hydrogen cyanide.
A-5
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4. CARBONYLATION (0X0)
The Oxo process is also called carbonylation, oxyformylation
or hydrofonnylation. It is a method of converting cc-olefins to al-
dehydes and or alcohols containing one additional carbon atom. The
olefin in the liquid state is reacted with a mixture of hydrogen and
carbon monoxide in the presence of a soluble cobalt catalyst, such as
dicobalt octacarbonyl, to produce the aldehyde (and some alcohol);
all or part of the aldehyde is then hydrogenated over a nickel
catalyst to form alcohol. The reaction is exothermic, about 35 kilo-
calories of heat being liberated per gram mole of olefin reacted.
The principal olefins used are propylene and the C^-Cio copolymers
of propylene and isobutylene.
Methanol is carbonylated to acetic acid in the presence of cobalt
octacarbonyl catalyst, Co0(CO)Q at 210°C and 7500 psig in a
L 0
slightly different version of this process.
A-6
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5. CONDENSATION
Condensation is a chemical reaction in which two or more molecules
combine, with the separation of water or some other simple substance.
Condensation is used in the making of a great many different chemicals,
as shown by the fifty which are listed in the condensation table.
In a typical condensation, two moles of phenol react with acetone
to give bisphenol A and water. The reaction occurs with dry HC1 as a
catalyst at 50°C for 8-12 hours.
In a somewhat different condensation, the cyclic compound
isophorone, 3,5,5-trimethyl-2-cyclohexene-l-one is synthesized together
with two moles of water fay heating three moles of acetone at 350°C with
calcium oxide.
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6. CRACKING, CATALYTIC
Cracking is not generally regarded as one of the unit processes
of commercial organic synthesis, but is sufficiently important in
process pollutant generation to be covered under this study. Cracking
involves thermal breakdown of aromatic and long-chain aliphatic
•structures to produce lower-molecular weight intermediates, or products.
Catalytic cracking converts high-boiling virgin gas oils to lower-
boiling gasoline components by application of thermal energy in a
moving bed of catalyst. Hydrocracking converts refractive gas oils
from cracking and coking operations to fuel gas, gasolines and some
diesel fuels by means of combined catalytic cracking, hydrogenation
and isomerization. Straight thermal cracking without a catalyst is
now primarily used for breaking heavy catalytic cycle stocks down to
fuel oils.
In the table on cracking all of the examples use catalysts ex-
cept the last process for production of vinyl chloride monomer (VCM)
which is a straight thermal process. The table lists several pro-
cesses for the production of acetylene from methane and natural gas,
and for isoprene from olefins. VCM is made by catalytic cracking of
ethylene dichloride. The other listed feedstocks require prior
treatment, such as ethylene, which subjected to direct chlorination
and oxychlorination yields ethylene dichloride which is cracked to VCM
and hydrochloric acid. The acid is recycled to the oxychlorination
reactor.
A-8
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7. DEHYDRATION
Dehydration is the process in which a compound is formed by the
elimination of water. A simple example from the dehydration table is
the formation of ethyl ether by the dehydration of ethyl alcohol.
Ring closure with the formation of water is seen in the dehydration
of diethanolamine to morpholine. Butadiene is oxidized and the
product dehydrated to give maleic anhydride.
A-9
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8. DEHYDROGENATION
Dehydrogenation is the process by which a new chemical is formed
by the removal of hydrogen from the feedstock compound. Aldehydes
or ketones are prepared by the dehydrogenation of alcohols, such as
ethyl alcohol to acetaldehyde, or isopropyl alcohol to acetone.
Saturated hydrocarbons are dehydrogenated to olefins. n-Butane is
catalytically dehydrogenated to butadiene> while the butenes yield
butadiene by oxidative dehydrogenation. The alkylation of benzene
with ethylene followed by dehydrogenation of the ethylbenzene yields
styrene.
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9. DEHYDROHALOGENATION
In the process of dehydrohalogenation hydrogen and a halogen,
usually chlorine, are removed from one or more feedstocks to obtain a
new chemical. The hydrogen and chlorine may be removed internally as
in the Transcat/Lummus Process for vinyl chloride monomer (VCM) in
which ethane and chlorine are fed (in the simplest case) to the
chlorination/oxychlorination/dehydrochlorination reactor. ct-Chloro-
propionic acid and 4-chlorocresol are dehydrohalogenated and con-
densed to give the pesticide, 2-(2,4-dichlorophenoxy) propionic acid,
also called 2,4-DP or Dichoroprop.
In a more complicated synthesis, aniline and p-chloronitro-
benzene are dehydrohalogenated, condensed and the nitro group hydro-
genated to N-phenyl-p-phenylenediamine. This intermediate is re-
ductively alkylated with acetone in the presence of hydrogen and a
catalyst to give the rubber processing chemical, N-isopropyl-N'-phenyl-
p-phenylenediamine.
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10. ESTERIFICATION
An ester is usually defined as a compound formed by substituting
a group such as ethyl for the ionizable H of an acid. Therefore,
esterification is the process whereby an ester is formed.
In direct esterification, an alcohol reacts with an acid, either
organic or inorganic:
CH.COOH + HOC7H_ ^ N CH_COOC H +H 0
Acetic Acid Ethyl Alcohol J EEhyl Acetate
Ethyl Nitrate
C H OH + HO-SO -OH f==^ C2H O'SO 'OH +
Monoethyl Sulfate
Closely allied with direct esterification are alcoholysis, in
which an alcohol displaces another alcohol, and acidolysis, in which
an acid drives out another acid:
CH COOC H + HOCH ^ CH COOCH + HOC H
CH3COOC2H + C-H COOH s C^^OOC^ + CH3COOH
Esters are key components of polymers, detergents, soaps and
other products, and are widely used as plasticizers in their own
right.
A-12
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11. HALOGENATION
Halogenation is the process whereby one or more halogen atoms
are introduced into an organic compound.
The preparation of organic compounds containing fluorine, chlorine,
bromine, and iodine can be accomplished by a variety of methods. The
conditions and procedures differ, not only for each member of the
halogen family but also with the type and structure of the compound
undergoing treatment.
The chlorine derivatives, because of the greater economy in
effecting their preparation, are by far the most important of the
technical halogen compounds and for this reason are given primary con-
sideration in the halogenation table. The bromine derivative, how-
ever, sometimes has certain advantages because of the greater ease in
effecting the replacement of this halogen in subsequent reactions,
or because it possesses certain pharmaceutical or dyeing properties.
Fluorocarbons containing two or more fluorines on a carbon atom are
characterized by extreme chemical stability and inertness. Their
main uses were as aerosol propellants and refrigerants. The remaining
10% had over 100 different important applications, including plastics,
films, elastomers, lubricants, textile-treating agents, solvents and
fire extinguisher products. The fluorocarbons are now discredited
due to their possible deleterious effect on ozone in the upper
atmosphere.
A-13
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Halogenations involve reactions of (1) addition, (2) substitution,
i.e., of hydrogen, (3) replacement, i.e., of groups, e.g., the hydroxyl
or sulfonic acid group.
(1) HC = CH + 2C12 3> C12HC - CHC1
2
(2) CH COOH + Cl P(red)> CH.C1COOH + HC1
/•o\ r u nu 4. un ZnCl
(3) i>9tlqutl f m,l
A-14
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12. HYDROGENATION
Hydrogenation, or reduction, is the term usually applied to a
reaction in which oxygen is withdrawn from or hydrogen added to a
compound. In addition, other elements besides oxygen may be eli-
minated from a molecule by the action of hydrogen, the most common
being nitrogen, sulfur, carbon, and halogens. In thes.e cases, ammonia,
hydrogen sulfide, methane, and the hydrogen halides are usually formed.
Reduction may be performed in a variety of ways: (1) by metals in
acid or basic solutions, (2) by alkali metals in alcoholic solutions,
(3) by electrolysis, and (4) by molecular hydrogen and catalysts.
Catalytic reduction by hydrogen is one of the most common and important
methods from a commercial point of view, as shown by the entries in
the hydrogenation table.
For example, the production of caprolactam starts by the oxidation
of toluene to benzoic acid. The benzoic acid is hydrogenated under
pressure in the presence of palladium catalyst in a series of con-
tinous stirred tank reactors at 170 C and 225 psi to cyclohexane-
carboxylic acid. This intermediate is converted to caprolactam by
reaction with nitrosylsulfuric acid (NOHSO ). This is a Snia Viscosa
process.
A-15
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13 . HYDROHALOGENATION
In hydrohalogenation a halogen acid, generally hydrochloric acid,
serves as the halogenating agent. Three types of reactions can occur.
1. Addition reactions, direct action:
A1C1,
CH2=CH2 + HC1 _ ^ CH3 CH2 Cl
The reaction is carried out at 35-40 °C and is exothermic. This
is a type of Friedel-Crafts reaction.
2. Substitution reactions, indirect action:
2r H + 2HC1 + 0 Cu C12 on A12°3
2C6 H6 + 2HC1 + 02 - 2 - 2 - ^ 20^01 + 2H20
3. Replacement reactions:
2n
rn nn + wn
CH3 OH + HCl - >CH3C1 + H20
Some dimethyl ether is produced as a by product to the
methyl chloride. This is also a type of Friedel-Crafts
synthesis of alkyl halides.
A-16
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14. HYDROLYSIS (HYDRATION)
Hydrolysis means decomposition by water. The term is applied
to reactions of both organic and inorganic chemistry wherein water
effects a double decomposition with another compound, hydrogen going
to one component, hydroxyl to the other. Effective hydrolysis by
water alone is rare and requires high temperature and pressures. The
most important accelerating agents are alkalis, acids and enzymes
as shown in the following five types of hydrolysis of commercial
significance:
1. Pure hydrolysis where water alone is used.
2. Hydrolysis with aqueous acid, dilute or concentrated.
3. Hydrolysis with aqueous alkali, dilute or concentrated.
4. Alkali fusion, with little or no water but at high temperatures,
5. Hydrolysis with enzymes as catalysts.
Hydration reactions where the hydrogen and hydroxyl radials
attach to the same molecule are also included. These are represen-
ted by the hydration of ethylene oxide to ethylene glycol and ethylene
to ethyl alcohol. Ethylene and water are combined at high temperature
and pressure and passed over a heterogeneous catalyst in a fixed bed
reactor. Ethyl ether is the major byproduct and may be controlled
by recycling. In minor side reactions the direct hydration process
produces small quantities of aldehydes, hydrocarbons, higher alcohols,
and ketones.
A-17
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15 . NITRATION
Nitration is the unit process used to introduce -NO or -O'NO
groups into organic compounds by the use of nitric acid or its
equivalent. The nitro group may replace a hydrogen atom bonded to
carbon:
RCHL + HON02 - » RCH2N02 + H20
Alternately, the nitro group may replace a hydrogen atom bonded to
oxygen or a nitrogen atom:
ROH + HON02 - *> R0-N02 + HO
RNH2 + HON02 - * RN-N02 + H^O
Strong dehydrating agents such as sulfuric acid enable nitryl ion
(NO ) formation
Nitrating agents used commercially include:
• Mixed acids , i.e., nitric acid admixed with a dehydrating
acid such as oleum, sulfuric acid, acetic anhydride,
phosphorous pentoxide, in which the nitryl ion is readily
formed.
• Nitric acid, concentrated and dilute; liquid and vapor.
• Nitric acid anhydride (dinitrogen pentoxide).
• Organic nitrates, such as acetyl and benxoyl nitrates.
• Alkali nitrates in the presence of sulfuric acid.
• Metal nitrates or ammonium nitrate with acetic acid.
• Nitrogen tetraoxide
A- 18
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A major commercial chemical used in formation of polyurethanes
is toluenediisocyanate (TDI) which is prepared by the nitration of
toluene with mixed sulfuric and nitric acids to dinitrotoluenediamine
(IDA) which is phosgenated to TDI.
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16. OXIDATION
Oxidation may be considered controlled, or tempered, combustion
and is one of the very useful chemical reactions for the entire
organic chemical industry. The oxidation processes are many and
varied.
The principal types of oxidative reactions are:
1. Conversion of an alcohol to an aldehyde.
2. Conversion of an aldehyde to an acid.
3. Conversion of an aliphatic or aromatic hydrocarbon to
an aldehyde, acid or other higher ozidation state.
4. Peroxidation of aromatics and aliphates.
5. Conversion of amines to azo compounds, phenols, nitro
aromatics, quinones, etc.
In the petrochemical industry, for which oxidation is one of the
most valuable conversions, a scission of C-C and C-H bonds is generally
involved, resulting in C-0 bonds. Air is the cheapest reagent, but
oxygen has been shown to be often more economical due to enhanced
yields, reduced recycle intervals, higher reaction rates, reduced
equipment sizes, and reduced heat loss due to nitrogen. Reactions
are carried out in both the liquid and vapor phases, using a variety
of catalysts, such as vanadium pentoxide. Fairly high temperatures
(about 400°C) are employed and since the reactions are highly
exothermic, the problem of heat removal is difficult.
Partial oxidation is employed to raise the temperature and to
oxidize partially hydrocarbons, such as the CC range, to acetylene
A-20
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and ethylene. Cracking is a part of this process.
Acetic acid may be produced by liquid phase oxidation with air
of a light naphtha in the C_-C7 range. The oxidation, which is
strongly expothermic, takes place in a stainless steel reactor at a
temperature of 170-200 C and a pressure of about 50 Kg/cm . Co-pro-
ducts are formic acid, propionic acid and acetone.
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17. OXYHALOGENATION
In the oxyhalogenation technique, or specifically in oxychlorina-
tion, chlorination is carried out by oxidizing HC1 catalytically to C12
with air or oxygen. This process has also been termed oxyhydrochlorina-
tion by some writers. The catalyst may be cuprous chloride plus an
alkali metal halide supported on a bed of inert material such as
silica or alumina. This process has been of particular importance
in the manufacture of vinyl chloride monomer (VCM) from ethylene,
chlorine, and air or oxygen.
The Monsanto Company/Scientific Design Company process for
the manufacture of VCM follows:
This process represents a "balanced" vinyl chloride plant,
wherein all hydrogen chloride produced as a co-product of the crack-
ing of ethylene dichloride (EDC) to monovinyl chloride monomer (VCM) is
recycled to the oxychlorination reactor. The latter may also receive
externally produced hydrogen chloride as a feed.
The reactions taking place in the process are:
C2H^ + Cl- -*• C.H.Cl (Direct Chlorination)
C2H4 + 2HC1 + 1/2 02 -»• C2H4C12+ 2H20 (Oxychlorination)
C H Cl -* CH = CHC1 + HC1 (Cracking)
The oxychlorination process is a vapor-phase reaction carried out in
a carbon steel reactor operating at moderate pressures. In direct
chlorination, ethylene and chlorine gases are charged to a reactor
system containing liquid EDC as reaction medium and coolant. The
A-22
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EDC produced in the reaction system is then treated for removal of
chlorine and HC1.
The crude EDC is purified by distillation and fed to pyrolysis
furnaces where it is cracked to yield vinyl chloride and HC1. The
anhydrous hydrogen chloride is recycled to the oxychlorination
reactor. Vinyl chloride is refined to product meeting the highest
industrial specifications.
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18. PHOSGENATION
Phosgenation is the reaction of phosgene - COC1-- with an organic
amine or alcohol. Phosgene is manufactured by the reaction of carbon
monoxide and chloride. It undergoes the usual reactions of an acid
chloride. Phosgene reacts with toluenediamine (IDA) to form toluene
diisocyanate (TDI) which must be separated from the four moles of
HC1 which are evolved. The reaction is carried out in the presence
of a high-boiling solvent, or carrier, from which the TDI is separated
by distillation. Monoisocyanates and other polyisocyanates are made
by similar processes.
About 85% of phosgene production (750 million Ibs in 1973) is
used in isocyanate manufacture, which includes TDI and diphenylmethane-
4,4'-isocyanate (MDI). The remainder is split between the pesticides,
such as Sevin, and the polycarbonate resins. To prepare Sevin
(carbaryl), sodium 1-napthoxide is reacted with phosgene to form an
intermediate which reacts with methylamine to give the product 1-
napthyl-N-methyl carbamate. Polycarbonate resins are made by the
reaction of bisphenol A with phosgene.
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19. POLYMERIZATION
Polymerization is a chemical process usually carried out with a
catalyst, heat or light, and often under high pressure, in which a
large number of relatively simple molecules combine to form a. chain-like
macromolecule.
The polymerization reaction occurs spontaneously in nature;
industrially it is performed by subjecting unsaturated or otherwise
reactive substances to conditions that will bring about combination.
This may occur by addition, in which free radicals are the initiating
agents that react with the double bond of the monomer by adding to
it on one side, at the same time producing a new free electron on the
other:
R- + CH2 = CHX *-R—CH2—CHX •
By this mechanism the chain becomes self-propagating. Polymeriza-
tion may also occur by condensation, involving the splitting out of
water molecules by two reacting monomers, and by so-called oxidative
coupling. The degree of polymerization (D.P.) is the number of monomer
units in an average polymer unit of a given sample.
Polymerization techniques may be: (1) in the gas phase at high
pressures and temperatures (200 C); (2) in solution at normal pressure
and temperatures from -70 to +70 C; (3) bulk or batch polymeriza-
tion at normal pressure at 150 C; (4) in suspension at normal pressure
at 60° to 80°C; (5) in emulsion form at normal pressure at -20° to
+60°C (used for copolymers). Catalysts of the peroxide type are
necessary with some of these methods.
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20. PYROLYSIS
Pyrolysis is the transformation of a compound into one or more
other substances by heat alone, i.e., without oxidation. It is thus
similar to destructive distillation. Though the term implies decom-
position into smaller fragments, pyrolytic change may also involve
isomerization and formation of higher molecular weight compounds.
Hydrocarbons are subject to pyrolysis, e.g., formation of carbon black
and hydrogen from methane at 1300 C and decomposition of gaseous
alkanes at 500 to 600°C. The latter is the basis of thermal cracking
(pyrolysis gasoline).
One application of pyrolysis is conversion of acetone into
ketenes by decomposition at about 700°C; the reaction is CH-COCH, ».
H2C=C=0 4- CH^. Pyrolysis of natural gas or methane at about 2000°C
and 100 mm Hg pressure produces a unique form of graphite. Synthetic
crude oil can be made by pyrolysis of coal, followed by hydrogenation
of the resulting tar. Large-scale pyrolysis of solid wastes is being
conducted for production of synthetic fuel oils and other products;
the method is said to require only 30 seconds at about 1000 F (Flash
pyrolysis). A pyrolysis method for recovery of usable materials
from scrap tires is under development.
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21. REFORMING (STEAM)-WATER GAS REACTION
The reforming table considers only the synthesis of methanol by
steam reforming or the water gas reaction. In a typical case, the
Lurgi low pressure synthesis process, hydrocarbons from methane to
naphtha, are desulfurized, mixed with steam and reformed at 830-850°C
to synthesis gas containing hydrogen, CO, and CO-. The synthesis
gas is compressed to 750-900 psi,together with the recycle gas in a
centrifugal compressor, preheated, and charged to the reactor. In a
shell and tube reactor the tubes are filled with catalyst and the shell
side with boiling water. Reaction temperature of 230-250°C is con-
trolled by the boiling water steam pressure. The reactor gases
after the reactor feed/effluent exchanger are cooled and methanol
is condensed and removed in a separator while the gas is recycled
to the compressor. A small portion of the gas is purged and used
as hydrogenation gas for desulfurization or as fuel.
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22. SULFONATION
Sulfonation is the process used for union of the sulfonic acid
group to carbon or nitrogen atoms in a specified organic chemical.
Direct sulfonations can be effected with solutions of sulfur trioxide,
chlorosulfonic acid, and sulfuryl chloride. The sulfonic acid group
can be introduced by the replacement of halogen atoms by sulfurous
acid or alkali sulfites.
Reaction of olefinic compounds with sulfites or bisulfites
leads to saturated sulfonic acid formation. Substitution of sulfonic
acid groups for hydrogen atoms in aromatic compounds takes place
readily using concentrated sulfuric acid. But hydrogen atom sub-
stitution in saturated aliphatics proceeds slowly, if at all, and only
under severe conditions.
Sulfonates are Important ingredients of detergents, soaps,
emulsifying agents and related products.
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APPENDIX B
Definitions of
Minor Unit Processes
-------
Appendix B Minor Unit Processes
1. ACID CLEAVAGE
Acid cleavage is the separation of a chemical, by action of an
acid catalyst, into at least two compounds. The table lists the
cumeue peroxidation process for the manufacture of phenol by the
liquid-phase air oxidation of cumene to cumene hydroperoxide which
is cleaved to phenol and acetone by the action of an acid catalyst,
generally sulfuric acid.
2. ACID REARRANGEMENT
A rearrangement which takes place under the influence of acid
catalysis may be considered an acid rearrangement. This is obviously
closely related to acid cleavage.
In the example from the table, cyclohexane carboxy,lic acid is
blended with oleum and fed to a multistage reactor where it is con-
verted to caprolactam by reaction with nitrosylsulfuric acid. Also,
p-aminophenol is formed by the hydrogenation of nitrobenzene,
suspended in sulfuric acid,to a hydroxylamine. This .intermediate
immediately rearranges to the p-aminophenol in the presence of the
strong acid.
3. AMINATION BY REDUCTION
In amination by reduction, in contrast to amination by
ammonolysis, a bond between carbon and nitrogen already exists in
B-l
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the molecule. The hydrogenation table contains the processes
using catalytic reduction by hydrogen to form amines from nitro or
nitrile compounds.
A different type of amination by reduction is shown in the
table for the formation of o-aminophenol by mixing £-nitrophenol
with 25 percent aqueous sodium bisulfite, adding zinc dust and
boiling. The amino compound crystallizes out from the cooled
reaction mixture. Also the intermediate, 2,2'-dichlorohydrazo-
benzene, is prepared from l-chloro-2-nitrobenzene by reduction
with zinc and alkali.
4. BECKMANN REARRANGEMENT
The oximes of ketones (ketoximes) undergo a Beckmann 'rearrange-
ment to amides when heated with inorganic reagents such as sulfuric
acid, polyphosphoric acid,PCI or SOC1 .
A simple but important example of this reaction is the Beckmann
rearrangement of cyclohexanone oxime using a sulfuric acid catalyst
to give the seven-membered cyclic amide, caprolactam. This cyclic
amide can be polymerized to give the textile fiber, nylon 6, which
is produced in about one-fourth the quantity of nylon 6,6 in the
United States.
5. BENZIDINE REARRANGEMENT
The rearrangement of hydrazobenzenes in the presence of strong
acids to yield p,p'-diaminobiphenyls is termed the Benzidine
B-2
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rearrangement. The example in the table shows the rearrangement
of the intermediate, 2,2'-dichlorohydrazobenzene, using hydro-
chloric acid, to 3,3'-dichlorobenzidine dihydrochloride.
6. CANNIZZARO REACTION
In the Cannizzaro reaction aldehydes without alpha-hydrogen
atoms undergo self-oxidation-reduction in the presence of strong
alkali to yield an acid and an alcohol. Although this reaction
is chiefly applicable in aromatics, it is involved in a somewhat
elaborate manner in the standard method for making pentaerythritol.
This is an interesting polyhydric alcohol used as an intermediate
in the manufacture of the high explosive tetranitrate ester (PETN).
In the synthesis of pentaerythritol, acetaldehyde is treated
with four equivalents of formaldehyde in an aqueous solution of
calcium hydroxide at 15-45°C. The initial step is an aldol
condensation in which the activated alpha-hydrogen atoms of three
moles of formaldehyde react with the more reactive carbonyl group
of formaldehyde to give a trihydroxyaldehyde. The next step is a
Cannizzaro reaction between the initial intermediate trihydroxy-
aldehyde and another mole of formaldehyde which results in reduction
of the former to pentaerythritol and the oxidation of the formaldehyde
to formic acid.
B-3
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7. CARBOXYLATION
In the carboxylation reaction, the alkali salt of phenol or
naphthol is reacted with carbon dioxide to give a carboxylic acid
on acidification. The process is also known as the Kolbe-Schmidt
reaction.
In the technical process for preparation of salicylic acid,
a solution of phenol in aqueous alkali is evaporated to a dry
powder, and the sodium phenolate is saturated with carbon dioxide
at 60 to 85 psi at 125°C. Free salicylic acid is liberated on
acidification of an aqueous solution of the cooled melt and is
obtained in close to the theoretical amount.
8. CHLOROHYDRINATION
In the chlorohydrination process hypochlorous acid adds to
the double bond of an olefin to give a chlorohydrin in which a
hydroxyl group and a chlorine atom are attached to adjacent carbon
atoms. These are the common reactants although hypobromous acid
behaves similarly. Halohydrin formation occurs by electrophilic
attack at the ~rr bond to give an intermediate halonium ion. Because
this is a bridged halonium ion, additions of hypohalous acids to
alkenes, such as cyclohexene, occur with trans-stereospecificitv.
Propylene reacts with chlorine and water in a reactor tower
to form propylene chlorohydrin. The dilute propylene chlorohydrin
solution is mixed with a 10 percent slurry or slaked lime and pumped
B-4
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to the hydrolyzer. To prevent further hydrolysis to propylene
glycol, the oxide is rapidly flashed out of the reaction zone.
9. DEALKYLATION (THERMAL)
Dealkylation is the removal of alkyl groups at high temperature
and pressure in the presence of hydrogen, and in the case of thermal
dealkylation, without a catalyst. Naphthalene may be produced from
a typical fluid catalytic cracking cycle oil (230 - 285°C cut)
containing about 50 percent aromatics, most of which are mono-, di-,
and trimethyl naphthalenes. Before dealkylating, this stock must be
concentrated by extraction and desulfurized.
The concentrated aromatic feed is pumped along with a hydrogen-
rich gas to a demethylation reactor. Typical operating conditions
for a noncatalytic thermal demethylator are 150 to 1000 psi, 760°C,
a hydrogen to naphthalene ratio 3:1 to 25:1, and a residence time of
2 to 300 sec. Part of the hydrogen-rich gas is recycled. The
liquid product is distilled to separate naphthalene, gasoline and
fuel oil. The naphthalene is generally better than 99 percent
pure and low in sulfur content.
10. DEALKYLATION (CATALYTIC)
Catalytic dealkylation is similar to the thermal process except
that a catalyst is used in the dealkylator. Catalytic cracking
catalysts, such as silica-alumina types, are used in the dealkylation
of methyl naphthalenes to naphthalene. The process is in general
similar to that used in the thermal dealkylation described above.
B-5
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11. ELECTROHYDRODIMERIZATION
The electrohydrodimerization process is represented by the
reductive dimerization of acrylonitrile (AN) with continuous pro-
duction of adiponitrile (ADN) by direct electrolysis. The Ashai
process follows:
AN is fed to the catholyte tank, where it is emulsified
with supporting salt. The resultant emulsion is sent to the
electrolyzer and is constantly recirculated through the electrolyzer
and the catholyte tank. A portion of AN dissolved in the catholyte
is converted into ADN by an electrohydrodimerization reaction
on the cathode surface. This process utilizes cation exchange
membranes which migrate cations selectively, to prevent oxidation
of the reaction mixture in the anode compartment.
Cation exchange
membrane
[—
a
. ,x
Ho 2p- H* 1
T
iAO 4- 2H* H*
Anolyte
^ > °CH- — CHCN
1 > \C(CH-)4CN
J
Catholvte
ailiotle
H ions to be consumed in the dimerization reaction migrate
through the cation exchange membrane. The supporting salt is of
a simple formula such as tetraethylammonium sulfate and has a low
affinity to organic materials. Therefore the supporting salt can
easily be separated from the oily layer.
B-6
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A portion of the catholyte is sent to the AN stripper, where
unconverted AN and by-products, such as propionitrile (PN), are
removed with a small quantity of water from the top. The top
stream is separated into two layers in the decanter. Oily effluent
is sent to the PN stripper, where AN is recovered from the top and
then recycled to the catholyte tank. PN is removed from the bottom.
Aqueous effluent is sent to the water stripper where dissolved AN is
recovered together with the by-products from the top. Water is
removed from the bottom.
The bottom stream of the AN stripper is separated into two layers
in the coalescer. The aqueous effluent is recycled to the catholyte
tank through the catolyte purification unit. After removing dissolved
water in the flush chamber, the oily effluent is sent to the heavy
cut column, where high boiling components such as trimer of AN are
removed from the bottom. The top stream of the heavy cut column is
sent to the 1st light cut column, where low boiling components are
removed from the top and ADN is obtained from the lower part of the
column.
ADN is recovered from the bottom stream of the heavy cut
column and the top stream of the first light cut column for recycling
to the process.
12. EPOXIDATION
In the process of epoxidation, an olefin is allowed to react
with an organic peracid, the TT bond of the olefin is broken and a
B-7
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three-membered cyclic ether, called an epoxide or oxirane, results.
Typical of the peracids that are used are perbenzoic, monoperphthalic,
and peracetic acids.
The Daicel process produces propylene oxide and acetic acid by
expoxidizing propylene with peracetic acid as follows:
Propylene and a solution of 30 percent peracetic acid and 10 to
15 percent acetic acid in ethyl acetate-containing stabilizer is
continuously fed into a series of three specially designed reactors
for epoxidation at 50 to 80° C under 9 to 12 atm. In about 2 to
3 hours, 97 to 98 percent of the peracetic acid is reacted to give
propylene oxide in 90 to 82 percent yield. Then the reaction pro-
2
ducts are fed into a stripper and distilled at 1.3 to 5.0 kg/cm .
From the top of the stripper, (1) a mixture of propylene and
propylene oxide, and from its bottom, (2) a mixture of ethyl acetate
and acetic acid, are discharged.
The first mixture is liquefied by cooling and compression, and
then fed into a propylene stripping column operated at 12 to 15 atm.,
where propylene is recovered and recycled into the first reactor.
Crude propylene oxide is discharged from the bottom of the propylene
column into a light-end column and a propylene oxide column as well
for refining.
The second mixture and a high boiler which is obtained from the
bottom of the propylene oxide column are fed into recovery columns,
where ethyl acetate is recovered and recycled into the peracetic
B-8
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acid reactor. Acetic acid is also recovered and used as it is or
refined for many applications.
13. HYDROACETYLATION
The hydroacetylation process is esterification with acetylene.
When acetylene and acetic acid are brought together with a suitable
catalyst, union takes place to form a vinyl ester or an ester of
ethylidine glycol, as shown below:
HC 2 CH + CH_COOH -» CH3COOCH=CH2
or
HC s CH + 2 CH COOH -» CH CH(OCOCH )
The usual catalysts are strong acids, sulfuric, methane di- and
tri- sulfonic, and phosphoric, with or without mercury salts, boron
fluoride and salts of various metals.
The process may be illustrated by the vapor-phase reaction
between acetylene and acetic acid in the presence of a zinc acetate
catalyst to yield vinyl acetate.
Acetylene is specially purified to remove hydrogen sulfide and
phosphorus compounds. It is then mixed in slight excess with vaporized
acetic acid and fed to a multitubular fixed-bed reactor containing a
catalyst of zinc acetate deposited on activated carbon (10 percent
zinc). Reaction is exothermic so the reactor is cooled by circulating
oil around the tubes. Reactor temperature is maintained at 175 to
200°C. The reactor effluent is condensed and fed to a light ends
column, where acetylene, methyl acetylene, propadiene, and other
B-9
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light ends are removed from the top of the column. The acetylene
must be repurified before it may be recycled.
Vinyl acetate is distilled overhead in a vinyl acetate column.
Recycle acetic acid is separated from heavy ends in a recovery column.
14. HYDROCYANATION
The hydrocyanation process is the addition of hydrogen cyanide.
Addition to carbonyl compounds occurs by nucleophic attack of the
positively polarized carbon to give a cyanohydrin. Alkynes, such
as acetylene, are also susceptible to nucleophilic attack. Therefore,
hydrogen cyanide adds to acetylene in either the liquid or vapor
phase to produce acrylonitrile by hydrocyanation.
Hydrocyanation is the first step in the production of methyl
methacrylate of which over 700 million pounds were made in 1974.
It is polymerized to products such as Lucite and Plexiglas, latex
paints, lacquer resins and molding powders. The acetone cyanohydrin
process is the only method currently used in the U.S. for the
manufacture of methyl methacrylate. Acetone cyanohydrin is obtained
by the hydrocyanation of acetone with hydrogen cyanide. The
cyanohydrin is reacted with sulfuric acid to yield methacrylamide
sulfate which is further hydrolyzed and esterified in a continuous
process to methyl methacrylate.
15. HYDRODEALKYLATION
Hydrodealkylation is a type of hydrogenation used' in petroleum
refining in which heat and pressure in the presence of hydrogen are
B-10
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Used to remove methyl or larger alkyl groups from hydrocarbon
molecules, or to change the position of such groups. The process
is used to upgrade products of low value such as heavy reformate
fractions, naphthenic crudes, or recycle stocks from catalyst
cracking. Also toluene and pyrolysis gasoline are converted to
benzene, and methyl naphthalenes to naphthalene by this process.
Hydrodealkylation may be illustrated by the following descrip-
tion of the Detol process of the Houdry Division of Air Products and
Chemicals, Inc. to produce high purity benzene (primarily) and
heavier aromatics from toluene and/or xylenes and/or C. and
heavier aromatics.
Feed (toluene and/or xylenes and/or Cq + aromatics), together
with a hydrogen containing gaseous stream, is heated at a specified
pressure to the required reaction temperature and passed over a dealkyla-
tion catalyst. Reactor effluent is cooled by heat exchange. Benzene
and unconverted toluene and/or xylene and heavier aromatics are
condensed, then flow to a high pressure flash drum where the major
portion of materials which boil below benzene are separated as gases.
The condensed liquid consisting of benzene, toluene and/or xylene
and heavier aromatics is pumped to a stabilizer. Dissolved hydrogen,
hydrogen sulfide and light hydrocarbons not removed in the flash drum
are stripped out. When benzene product must meet acid wash color
specifications, the stabilizer bottoms are passed through a fixed
bed clay treater. The clay treated aromatic liquid is then distilled
B-ll
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in a benzene fractionator to produce the desired specification
benzene.
Unconverted toluene and/or xylenes and heavier aromatics are
recycled through the catalyst with the fresh feed.
Depending on the quantity and purity of available make-up
hydrogen, it may be desirable to include a hydrogen concentration
step to treat a portion of the vapors from the high pressure flash
drum. This maintains the desired hydrogen partial pressure in the
system while conserving hydrogen.
16. ISOMERIZATION
Isomerization is a. process for converting a hydrocarbon or
other organic compound into an isomer. In isomerization, the
arrangement of the atoms in a molecule is changed without changing
the number of atoms.
An example is the Isomar process of the UOP Process Division
which yields either para- or ortho-xylene, or both depending on
the separation procedures involved. The process follows:
The feedstock may be of any C aromatic mixture; e.g., from
o
catalytic reformates or from pyrolysis gasoline. The latter often
contains as high as 40 percent ethylbenzene, which is no detriment
to the operation. Feedstocks may be pure solvent extracts or frac-
tional heart-cuts containing as high as 25 percent saturates.
Hydrogen supply may be from catalytic reforming or any other
suitable source. Chemical hydrogen consumption is minor.
B-12
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C aromatic reactor feed, deficient in one or more components
o
relative to equilibrium composition, is processed over a fixed bed
of catalyst in the presence of hydrogen. The liquid portion of the
effluent is fractionated to remove both light and heavy aromatic by-
products , as well as the cracked materials resulting from inclusion
i,
of saturates in the feed. Para-xylene and/or ortho-xylene are
separated from the resulting fractionation heart-cut, thereby pre-
paring a recycle material to the Isomar reactor. Fresh feedstock
is introduced into the circuit in the most appropriate place.
17. NITROSATION
The reaction of amines with nitrous acid is termed nitrosation
and is of great theoretical and practical importance. Hitrosation
is a key reaction in the synthesis of caprolactam. Over 700 million
Ibs of caprolactam were produced in 1974 for use in making nylon 6,
its only outlet. Nylon 6 accounts for about 30 percent of nylon
capacity.
The low sulfate process for production of caprolactam, as
developed by Stamicarbon BV, follows:
The hydroxylamine is produced in a gas-liquid contactor
starting from nitrate ions and hydrogen gas in the presence of a
noble metal catalyst.
The basic reaction is the reduction of nitrate ions according
to NO" -t- 2H+ + 3H» -" NH OH+ + 2H 0 in the presence of a buffering
acid.
B-13
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The formed hydroxylamine reacts with pure cyclohexanone in the
presence of an organic solvent, at a relatively low pH. The con-
version of the cyclohexanone in this step is about 98 percent.
The remaining cyclohexanone is converted in a subsequent step, at
a higher pH, so a conversion of 100 percent is obtained.
The cyclohexanone oxime is separated from the solvent by
distillation and pumped to the rearrangement unit, where through
mixing with oleum the rearrangement of the cyclohexanone oxime con-
figuration into the caprolactam configuration takes place.
The rearrangement mixture is subsequently neutralized with
aqueous ammonia and, after settling,the crude caprolactam solution
is decanted from the ammonium sulfate solution, which later can be
processed to fertilizer grade crystals.
18. OXYACETYLATION
In oxyacetylation vinyl esters are prepared by esterification
of an acid with ethylene in the presence of oxygen and a suitable
catalyst. An important commercial process makes vinyl acetate
monomer from ethylene, acetic acid and oxygen.
The process to make vinyl acetate developed by the U.S.
Industrial Chemicals Division of National Distillers follows:
A fixed-bed tubular reactor with a noble metal catalyst is
supported on a special carrier inside the multitubular reactor.
Feed mixture of ethylene, acetic acid and oxygen circulates through
the catalyst-filled tubes.
B-14
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Effluent from the absorber is combined with condensed reactor
effluent and fed to the primary separator facilities. At the same
time, absorber off-gas is water-scrubbed to reclaim acetic acid and
prevent corrosion of the recycle gas compressor.
Scrubber bottoms are combined with absorber bottoms to feed
the purification process while unreacted ethylene and oxygen saturated
with water^ in the overhead section are sent to the carbon dioxide
removal section with a compressor that provides the pressure drive
in the total synthesis loop.
Carbon dioxide is the only component, in addition to minor
impurities which are purged, that is not totally recycled. C02
is removed with a potassium carbonate system compatible with the
vinyl acetate process. The absorber overhead, which is primarily
ethylene, is fed to the acid tower for eventual return to the
reactor.
The primary distillation system is made up of a primary tower
and two auxiliary strippers combined with a common condenser and
receiver. In the primary tower, the vinyl acetate, dissolved gases,
light and heavy impurities (lower boiling than acetic acid) and
water are taken overhead. Bottom stream, containing acetic acid
and minor amounts of heavy impurities, is returned to the absorber
and to the acid vaporizer.
Overhead condenses and separates into two layers, organic and
aqueous, in a decanter. Part of the vinyl acetate layer is returned
B-15
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to the column as reflux to entrain more water from the column. Water
layer is removed from the distillation system and net vinyl acetate
production is recovered from the system via the overhead system.
Water phase is removed from the decanter and fed to the top
of a tower which strips vinyl acetate out of the aqueous bottom to
a level of less than 10 ppm.
Vinyl acetate from the bottom of the drying tower is pumped
to the lights tower in which residual acetaldehyde and other light
ends are concentrated and removed in the overhead. In the product
tower, heavy impurities in the vinyl acetate are concentrated as a
bottoms fraction. The tower overhead is condensed, cooled and
pumped to storage. Less than 25 ppm of ethyl acetate is contained
in the product.
19. OZONOLYSIS
Ozonolysis is the reaction between alkenes and ozone which
occurs at low temperatures to cleave the double bond. Ozonization
first occurs by electrophilic addition of ozone to produce the
unstable cyclic molozonide in which the TT bond of the alkene has been
replaced by two carbon-oxygen bonds. The molozonide decomposes into
two fragments which recombine in an alternative way to form the
ozonide. Ozonides are explosive and are seldom isolated but are
decomposed with a reducing agent to yield aldehydes or ketones.
Zinc in hydrochloric acid is commonly employed. To produce an acid
the ozonide may be decomposed by adding more hydrogen peroxide and
acetic acid which oxidizes the aldehyde to an acid.
B-16
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APPENDIX C
Directory of Companies
Owning and/or Licensing
Described Processes
-------
Appendix C DIRECTORY OF COMPANIES, OWNING AND/OR
LICENSING DESCRIBED PROCESSES
Aicello Chemical Co., Ltd.
183 Minami-cho, Maeda
Toyohashi-shi Aichi-ken, 440
JAPAN
Airco, Inc.
575 Mountain Avenue
Murray Hill, NJ 07974
Akita Petrochemicals Co.
c/o Sumitomo Chemical Co.
Tokyo Office, 1-3-2 Marunouchi
Chiyoda-ku, Tokyo 100
JAPAN
Aldehyd GmbH
Licensor:
Hoechst-Uhde Corp.
560 Sylvan Avenue
Englewood Cliffs, NJ 07632
and
Udht GmbH
Deggingstrasse 10-12
4600 Dortmund 1
FEDERAL REPUBLIC OF GERMANY
Allied Chemical
Columbia Road & Park Avenue
Morristown, NJ 07960
Alusuisse
Licensor:
Krupp Chemiganlagenbau
Limbecker Platz 1
Essen,
FEDERAL REPUBLIC OF GERMANY
American Synthetic Rubber Co.
P.O. Box 360
Louisville, KY 40201
ANIC
Licensor:
SNAM Progetti S.P.A.
20097 San Donato
Milan
ITALY
Asahi Chemical Industries Co., Ltd.
Licensor:
Asahi/America
425 Riverside Avenue
Medford, MA 02155
Atlantic-Englehard
Atlantic Richfield Co.
ARCO Technology Inc., Division
1500 Market Street
Philadelphia, PA 19101
Atlantic Richfield Co.
ARCO Technology Inc. Division
1500 Market Street
Philadelphia, PA 19101
ATO
Tour Aquitaine
Cedex No. 4
92080 Paris-La Defense
FRANCE
The Badger Company, Inc.
One Broadway
Cambridge, MA 02142
Badische-Anilin & Soda Fabrik AG
Girokonto 545 07300
6700 Ludwigshaven
FEDERAL REPUBLIC OF GERMANY
Bakol-Scientific Design
Scientific Design Co., Inc.
Two Park Avenue
New York, NY 10016
Bayer AG
509 Leverkusen, Bayerwerk
FEDERAL REPUBLIC OF GERMANY
Beaunit Corp.
P. 0. Box 12234
Res. Triangle Park, NC 27709
C-l
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(CHEMICO)
Biazzi
Licensor:
Chemical Construction Co.
1 Perm Plaza
New York, NY 10001
Blaw-Knox Company
One Oliver Plaza
Pittsburgh, PA 15222
Borden Chemical Co.
680 Fifth Avenue
New York, NY 10019
Bowmans Chemical
Licensor :
Scientific Design Co., Inc.
Two Park Avenue
New York, NY 10016
BP Chemicals International Ltd.
Devonshire House
Mayfair Place
Piccadilly, London W1X6AY
ENGLAND
C. F. Braun & Co.
Alhambra, CA 91802
British Gas Corp.
326 High Holborn
London WC1V 7PT
ENGLAND
British Gas Corp.
North West Region
Manchester, M32 ONJ
UNITED KINGDOM
Chemical Construction Corp.
1 Penn Plaza
New York, NY 10001
The Chemithon Corp.
5430 W. Marginal Way, S.W.
Seattle, WA 98106
Chevron Research Company
200 Bush Street
San Francisco, CA 94104
C'd F Chimie-LFP-Societe
Chimique des Charbonnages
Licensor:
Institut Francais du Petrole
1 et 4, Avenue de Bois-Preau
92-Rueil-Malmaison
FRANCE
Chiyoda Chemical Engineering &
Construction Co.
1580 Tsurumi-cho Tsurumi-ku
Yokohama-shi, Kanagawa-ken 230
JAPAN
Ciba-Geigy Corp.
Saw Mill River Road
Ardsley, NY 10502
Conoco Chemical Company
Plaza E
Saddlebrook, NJ 07662
Cosden Oil & Chemical Co.
P. 0. Box 1311
Big Spring, TX 79720
Crawford & Russell Inc.
Stamford, CT 06904
Daicel, Ltd.
Toranomon, Mitsui Bldg.
8-1 Kasumigaseki 3-Chome
Chiyoda-ku
Tokyo 100
JAPAN
Daikin Kogyo Co., Ltd.
Shin-Hankyo Bldg.
8, Umeda, Kita-ku, Osaka
(CHEMICO)JAP AN
Dart Industries, Inc.
8480 Beverly Boulevard
Los Angeles, CA 90048
Denki Kagaku
Scientific Design Co., Inc.
Two Park Avenue
New York, NY 10010
C-2
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Deutsche Texaco AG
Licensor:
Texaco Development Corp.
135 East 42nd Street
New York, NY 10017
Diamond Shamrock Chemical Co.
1100 Superior Avenue
Cleveland, OH 44114
Dynamit Nobel AG
Troisdorf
FEDERAL REPUBLIC OF GERMANY
Eastman Kodak Co.
Tennessee Eastman
Kingsport, TN 37662
C & I/Girdler, Inc.
P. 0. Box 174
1721 South Seventh Street
Louisville, KY 40201
B. F. Goodrich Chemical Co.
61 Oak Tree Blvd.
Cleveland, OH 44131
Gulf Oil Chemicals Co.
New Business Development Div.
P. 0. Box 2100
Houston, TX 77001
Gulf Research & Development Co.
P. 0. Drawer 2038
Pittsburgh, PA 15230
Englehard Industries Div. Haldor Topsoe
Englehard Minerals & Chemicals Corp.Licensor:
430 Mountain Avenue Arthur G. McKee & Co.
Murray Hill, NJ 07974 Cleveland, OH 44131
Ethylene Plastique
Tour Aurore - Cedex No. 5
92080 Paris-La Defense
FRANCE
Fluor Engineers & Constructors,
2500 South Atlantic Boulevard
Los Angeles, CA 90040
FMC Corporation
Chemical Research & Development
Center
Box 8
Princeton, NJ 08540
Foster Wheeler Corp.
110 South Orange Avenue
Livingston, NJ 07039
Gelsenberg Chemie GmbH
Rosastrasse 2
43 Essen 1 Postfach 30
FEDERAL REPUBLIC OF GERMANY
Hercules Inc.
910 Market Street
Wilmington, DE 19899
HIAG
Inc.Licensor:
American Lurgi Corp.
5 East 42nd Street
New York, NY 10017
Hodogaya Chemical Co., Ltd
No. 2-1 Shiba Kotoshira-cho, Minato-ku
Tokyo
JAPAN
Hoechst AG
Licensor:
Hoechst Uhde Corp.
560 Sylvan Avenue
Englewood Cliffs, NJ 07632
Honshu Chemical Industry Co.
Maruzen Bldg., 2-3-10
Nihonbashi, Chuo-ku
Tokyo 103
JAPAN
C-3
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Hooker Chemical Corp.
P. 0. Box 189
Niagara Falls, NY 14302
Houdry Division
Air Products & Chemicals, Inc.
Box 538
Allentown, PA 18105
Hydrocarbon Research, Inc. .
115 Broadway
New York, NY 10006
Idemitsu Kosan Co.
3-1-1 Marunouchi, Chiyoda-ku
Tokyo 100
JAPAN
Institut Francais du Petrole
1 et 4 Avenue de Bois-Preau
92 Rueil Malmaison
FRANCE
Imperial Chemical Industries ,Ltd.
Agricultural Div.
P. 0. Box No. 1
Billingham, Teesside
UNITED KINGDOM
Inventa AG
Stampfenbachstrasse 38
Zurich 6
SWITZERLAND
Japan Catalytic Chemical Industry
Licensor:
Simon-Carves Ltd.
Sim-Chem Division
P. 0. Box 49
Stockport, SK3 ORZ
UNITED KINGDOM
Japan Synthetic Rubber Co., Ltd.
No. 1, 1-Chome, Kyobashi
Chuo-ku, Tokyo 104
JAPAN
Co.
The M. W. Kellogg Co.-
1300 Three Greenway Plaza East
Houston, TX 77046
Kureha Chemical Industry Co., Ltd.
8-1 Chome, Nihonbashi Horidome-cho
Chuo-ku Tokyo 103
JAPAN
Kyowa Hakko USA Inc.
521 Fifth Avenue
New York, NY 10017
Lankro Chemicals Ltd.
Bentcliffe Works
Salters Lane
Eccles, Manchester M300 BH
ENGLAND
The Leonard Process Co., Inc.
37 W. 37th Street
New York, NY 10018
Licensintorg (USSR)
Licensor:
Davy Powergas Ltd.
8 Baker Street
London, W1M IDA
ENGLAND
Linde AG
Carl von Linde Strasse 6
8023 Hoellriegelskreuth
FEDERAL REPUBLIC OF GERMANY
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Lonza/First Chemical Corp.
Licensor:
First Mississippi Corp.
700 North Street
Jackson, MS 39205
The Lummus Company
1515 Broad Street
Bloomfield, NJ 07003
American Lurgi Corp.
5 East 42nd Street
New York, NY 10017
C-4
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Marathon Oil Co.
539 South Main Street
Findlay, OH 45840
Joseph Meissner GmbH
Licensor:
C&I/Girdler Inc.
P. 0. Box 174
1721 South Seventh Street
Louisville, KY 40201
Mitsubishi Gas Chemical Co.
The Badger Company, Inc.
One Broadway
Cambridge, MA 02142
Mitsui Toatsu Chemicals, Inc.
Kasumigaseki Bldg.,
3-2-5 Kasumigaseki, Chiyoda-ku
Tokyo 100
JAPAN
MoDoKemi AB
S-444 01 Stenungsund 1
SWEDEN
Monochem Inc.
P. 0. Box 488
Geismar, LA 70734
Monsanto Enviro-Chem Systems Inc.
800 North Lindbergh Boulevard
St. Louis, MO 63166
Montedison S.p.A.
Brev/Lic
Lorgo Donegani 1/2
20121 Milano,
ITALY
Montefibre S.p.A.
Via Pola 14
20124 Milano
ITALY
Naphthachemie
203 rue du Faubourg
Saint-Honore
Paris 8e
FRANCE
Nihon Yuki Co., Ltd.
Gamo 3.030
Koshigaya, Saitama,
JAPAN
Nipak, Inc.
301 South Hardwood St.
Box 2820
Dallas, TX 75221
Nippon Shokubai Kagaku
Kogyo Co., Ltd.
(English name)
Japan Catalytic
Chemical Industry Co.
Licensor:
Simon-Carves Ltd.
Sim-Chem. Division
P. 0. Box 49
Stockport, SK3 ORZ
UNITED KINGDOM
Nippon Soda Co.
Shin-Ohtemachi Bldg.,
2-2-1 Ohtemachi, Chiyoda-ku
Tokyo 100
JAPAN
Nippon Steel Chemical Co.
6-17-2 Ginza, Chuo-ku
Tokyo 104
JAPAN
Nippon Zeon Co., Ltd.
Furukawa Sogo Bldg.
6-1 Marunouchi 2-Chome
Chiyoda-ku, Tokyo
JAPAN
Nissan Chemical Industries, Ltd.
Kowa Hitotsubashi Bldg.
3-7-1 Kanda-Nishiki-cho,
Chiyoda-ku, Tokyo 101
JAPAN
Petro-Tex Corp.
8600 Park Place
Houston, TX 77017
C-5
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Pfaudler Co., The Sybron Corp
1000 West Avenue
'Rochester, NY 14603
Phillips Petroleum Co.
Bartlesville, OK 74003
PPG Industries, Inc.
Chemical Division
One Gateway Center
Pittsburg, PA 15222
Polysar Ltd.
Sarnia, Ontario
CANADA
Products Axole
Licensor:
Foster Wheeler Corp.
110 South Orange Avenue
Livingston, NJ 07039
Reichold Chemicals, Inc.
RCI Building
While Plains, NY 10602
Rhone Progil
Service Licenses de Precedes
25, Quai Paul-Doumer
F 92408 Courbevoie
FRANCE
Ruhrchemie AG
Licensor:
Hoechst-Uhde Corp.
550 Sylvan Avenue
Englewood Cliffs, NJ 07632
Ruhrchemie/FWH Farbwerke
Licensor:
Hoechst Uhde Corp.
550 Sylvan Avenue
Englewood Cliffs, NJ 07632
Scientific Design Co.
Two Park Avenue
New York, NY 10016
Selas Corp. of America
Dresher, PA 19025
Shell Development Co.
One Shell Plaza
P.O. Box 2463
Houston, TX 77001
Sherwin Williams Chemicals
P. 0. Box 6520
Cleveland, OH 44101
Shikoku Kasei Co., Ltd.
147 Minato-machi Marugame-City
Kagawa-Pre.,
JAPAN
Simon-Carves Ltd.
Sin-Chem Division
P. 0. Box 49
Stockport, SK 3 ORZ
UNITED KINGDOM
SNAM Progetti S.p.A.
20097 San Donato Milanese
ITALY
SNIA Viscosa S.p.A.
via Montbello
18-20121 Milano
ITALY
SNPA
Societe Nationale des Petroles D'Aquitaine
Tour Aquitaine
Cedex No. 4
Paris-La Defense 92080
FRANCE
Solvay & Cie
Administration Centrale
33, Rue du Prince Albert
Brussels
BELGIUM
Inc.
C-6
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Stamicarbon bv
P.O. Box 10
Geleen
THE NETHERLANDS
The Standard Oil Co.
Midland Building
Cleveland, OH 44115
Standard Oil Co. (Indiana)
910 South Michigan Avenue
Chicago, IL 60605
Stauffer Chemical Co.
Westport, CT 06880
Stone & Webster Corp.
One Penn Plaza
250 West 34th Street
New York, NY 10001
Sumitomo Chemical Co., Ltd.
15 5-Chome Kitahama
Higashi-ku, Osaka 541
JAPAN
Technip
(Compagnie Francaise DfEtudes et
de Construction)
232 Ave. Napoleon Bonaparte
92500-Rueil-Malmaison
FRANCE
Texaco Development Corp.
135 East 42nd Street
New York, NY 10017
Tokuyama Soda Co., Ltd.
No. 4-5, 1-Chome
Nishi-Shimbashi, Minato-ku
Tokyo
JAPAN
Toms River Chemical Corp.
P. 0. Box 71
Toms River, NJ 08753
Toray Industries, Inc.
2, Nihonbashi-Muromachi
2-Chome
Chuo-ku, Tokyo 103
JAPAN
Total-Compagnie Francaise
de Raffinage
Owners(50-50):
Cie Francaise des Petroles
Cie Francaise de Raffinage
5 Rue Michel-Ange
75 Paris 16e
FRANCE
Toyo Toatsu Industries, Inc.
Licensor:
Mitsui Toatsu Chemicals, Inc.
Kasumigaseki Bldg.
3-2-5 Kasumigaseki, Chiyoda-ku
Tokyo 100
JAPAN
Toyo Soda Manufacturing Co., Ltd.
Toso Bldg., 7-7, 1-Chome, Akasaka
Minato-ku, Tokyo
JAPAN
Ube Industries Ltd.
Products Development Dept.
7-2, Kasumigaseki,
Chiyoda-ku, Tokyo
JAPAN
UCB, S.A.
Chaussee de Charleroi 4
B-1060 Brussels
BELGIUM
Friedrich Uhde GmbH,
Degginstrasse 10-12
4600 Dortmund
FEDERAL REPUBLIC OF GERMANY
C-7
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Union Carbide Corp.
Chemicals & Plastics Div.
270 Park Avenue
New York, NY 10017
Union Carbide Corp.
Linde Division
270 Park Avenue
New York, NY 10017
Uniroyal International
1230 Avenue of the Americas
New York, NY 10020
United Chemicals & Coke, Ltd.
Licensor:
Foster Wheeler Corp.
110 South Orange Avenue
Livingston, NJ 07039
Universal Oil Products Co. (UOP)
10 UOP Plaza
Algonquin & Mt. Prospect Roads
Des Plaines, IL 60016
U. S. Industrial Chemicals Co.
Div. of National Distillers and
Chemical Corp.
99 Park Avenue
New York, NY 10016
Veba-Chemie AG
Postfach 45
466 Gelsenkirchen-Buer
FEDERAL REPUBLIC OF GERMANY
von Heyden/Wacker
Licensor:
Wacker Chemie GmbH
8 Muenchen 22
Prinzregentenstrasse 22 Postfach
FEDERAL REPUBLIC OF GERMANY
Vulcan-Cincinnati, Inc.
1329 Arlington Street
Cincinnati, OH 45225
Wacker Chemie GmbH
8 Muenchen 22
Prinzregentenstrasse 22 Postfach
FEDERAL REPUBLIC OF GERMANY
Welsbach Corp.
56 Haddon Avenue
Haddonfield, NJ 08033
C. W. Witten
Now owned by:
Dynamit Nobel AG
Troisdorf
FEDERAL REPUBLIC OF GERMANY
Zimmer AG
60, Postfach 600 102
6 Frankfurt (M)
FEDERAL REPUBLIC OF GERMANY
C-8
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