Wisconsin Administrative Code
Department of Natural Resources
NR 200-299 - Environmental Protection Wisconsin Pollutant Discharge Elimination System
Chapter NR 235 - Organic chemical manufacturing
Subchapter XI - Indirect Discharge Point Sources
Appendix A TO CHAPTER NR 235 - NONCOMPLEXED METAL-BEARING WASTE STREAMS AND CYANIDE-BEARING WASTE STREAMS

Product

Process

Methylhydroabietate

Esterification of hydroabietic acid (rosin) with methanol

Acrylic acid

Oxidation of propylene via acrolein

N-Butyl alcohol

Hydrogenation of n-butyraldehyde, Oxo process

Cyclohexanone

From phenol via cyclohexanol by hydrogenation-dehydro-genation

Fatty amines

Batch hydrogenation of fatty nitriles

Heliotropin

Oxidation of isosafrole, chromium catalyst

Isobutanol

Hydrogenation of isobutyraldehyde, Oxo process

Cyclohexyl mercaptan

Cyclohexanol + hydrogen sulfide

Ethyl mercaptan

Ethanol + hydrogen sulfide

Methanol

H.P. synthesis from natural gas via synthetic gas

Oxo alcohols, C7-C11

Carbonation and hydrogenation of C6-C10 olefins

Polyoxypropylene diamine

Polypropylene glycol + ammonia

n-Propyl alcohol

Hydrogenation of propionaldehyde, oxo process

SAN resin

Suspension polymerization

Styrene

Dehydrogenation of ethylbenzene

Styrene

Dehydration of methyl benzyl alcohol, coproduct of propylene oxide

1-Tetralol, 1-tetralone mix

Oxidation of tetralin (1,2,3,4- tetrahydronaphthalene)

3,3,3-Trifluoropropene

Catalyzed hydrogen fluoride exchange with chlorinated propane

Vinyl toluene

Thermal dehydrogenation of ethyltoluene

Product

Process

Methylhydroabietate

Esterfication of hydroabietic acid (rosin) with methanol

Acetaldehyde

Oxidation of ethylene with cupric chloride catalyst

Acetic acid

Catalytic oxidation of butane

Acetone

Dehydrogenation of isopropanol

Acrylamide

Catalytic hydration of acrylonitrile

Acrylic acid

Oxidation of propylene via acrolein

Acrylonitrile

Propylene ammoxidation

Adiptic Acid

Oxidation of cyclohexanol-cyclohexanone mixture

Adipic acid

Oxidation of cyclohexane via cyclohexanol-cyclohexanone mixture

Allynitrile

Allychloride + sodium cyanide

Aniline

Hydrogenation of nitrobenzene

Benzofurans, 2,3 dihydro-2,2-dimethyl-7-benzofuranol

From o-Nitrophenol + methallyl chloride

n-Butyl alcohol

Hydrogenation of n-butyraldehyde, oxo process

1,4 Butanediol

Hydrogenation of 1,4-butynediol

Butryolactone

Dehydrogenation of 1,4-butanediol

Caprolactam

From cyclohexane via cyclohexanone and its oxime

Lilian (hydroxydihydrocitronellal)

Hydration and oxidation of citronellol

1,2-Dichloroethane

Oxyhydrochlorination of ethylene

Dialkyldithiocarbamates, metal salts

Dialkylamines + carbon disulfide

2-Ethylhexanol

From n-butyraldehyde by aldo condensation and hydrogenation

Fatty amines

Batch hydrogenation of fatty nitriles

Geraniol

B-Myrcene + hydrogen chloride, esterfication of geranyl chloride hydrolysis of geranyl acetate

Furfuryl alcohol

Hydrogenation of furfural

Geraniol (citral)

Oxidation of geraniol, copper catalyst

Glyoxal

Oxidation of ethylene glycol

Isobutanol

Hydrogenation of isobutyraldehyde, Oxo process

Isopropanol

Catalytic hydrogenation of acetone

2-Mercaptobenzothiazoles, copper salt

2-Mercaptobenzothiazole + copper salt

Methanol

High pressure synthesis from natural gas via synthetic gas

Methanol

Low pressure synthesis from natural gas via synthetic gas

Methyl ethyl ketone

Dehydrogenation of sec-butanol

Product

Process

C7-C11 oxo alcohols

Carbonation and hydrogenation of C6-C10 olefins

Phenol

Liquid phase oxidation of benzoic acid

Polyoxyalkylene amines

Polyoxyalkylene glycol + ammonia

Polyphenylene oxide

Solution polymerization of 2-6-xylenol by oxidative coupling cuprous salt catalyst

Polyoxypropylene diamine

Polypropylene glycol + ammonia

Quinaldine dye intermediate

Skraup reaction of aniline crotonaldehye

Silicone fluids

Hydrolysis and condensation of chlorosilanes

Silicone rubbers

Hydrolysis and condensation of chlorosilanes

Silicone specialties, such as grease, dispersion agents, defoam-ers, and other products

Silicone resins

Hydrolysis and condensation of methyl, phenyl, and vinyl chlorosilanes

Silicone fluids

Hydrolysis of chlorosilanes to acyclic and cyclic organosilox-

anes

Styrene

Dehydration of a-methylbenzyl alcohol, coproduct of propy-lene oxide

Tetrachloroethylene (perchloroethylene)

Oxyhydrochlorination of tetrachloroethane

Tris(anilino)s-triazine

Cyanuric chloride + aniline + cogeners

Trichloroethylene

Oxyhydrochlorination of tetrachloroethane

Unsaturated polyester resin

Reaction of maleic anhydride + phthalic anhydride + propylene glycol polyester with styrene or methyl methacrylate

Cyanide Bearing Waste Streams

Product

Process

Acetone cyanohydrin

Acetone + hydrogen cyanide

Acetonitrile

By-product of acrylonitrile from propylene by ammoxidation

Acrylic resins

Solution polymerization

Acrylic fiber (85% acrylonitrile)

Suspension polymerization and wet spinning

Acrylic fiber (85% acrylonitrile)

Solution polymerization and wet spinning

Acrylonitrile

Ammoxidation of propylene

Adiponitrile

Butadiene + hydrogen cyanide (direct cyanation)

Allylnitrile

Allyl chloride + sodium cyanide

Dimethoxybenzaldehyde

Hydroquinone dimethyl ether + hydrogen cyanide, hydrolysis

Benzyl cyanide

Benzyl chloride + sodium cyanide

Coal tar products

Distillation of coal tar condensate

Cyanoacetic acid

Chloracetic acid + sodium cyanide

Cyanuric chloride

Catalyzed trimerization of cyanogen chloride

Vat dyes, indigo paste as vat blue 1

Sodamide + potassium N-phenylglycine, fused with caustic; or N-phenylglycine + aniline +formaldehyde + sodium bisulfite, sodium cyanide hydrolysis with potassium hydroxide

Disperse dyes, azo and vat

Ethylenediamine tetraacetic acid

Ethylene diamine + formaldehyde + sodium cyanide

Diethylenetriamine pentaacetic acid

Diethylenetriamine + formaldehyde + sodium cyanide

N,N'-Bis(o-acetamidophenol)ethylene- diamine, ferric com-

Salicylaldehyde + ethylene diamine + hydrogen cyanide,

plex

hydrolysis to amide

Diethylenetriamine pentaacetic acid, pentasodium salts

Diethylenetriamine pentaacetic acid + caustic

Hydroxyethyl ethylenediamine triacetic acid, trisodium salt

Ethylene diamine + ethylene oxide + formaldehyde + sodium cyanide, hydrolysis

5,5 Dimethyl hyantoin

Acetone + ammonia + carbon dioxide + hydrogen cyanide

Hydrogen cyanide

Byproduct of acrylonitrile by ammoxidation of propylene

Iminodiacetic acid

Hexamethylene tetraamine + hydrogen cyanide, hydrolysis of

iminoacetonitrile salt

Methionine

Acrolein + methyl mercaptan, with hydrogen cyanide and ammonium carbonate

Nitrilotriacetic acid

Hexamethylene tetraamine + hydrogen cyanide, hydrolysis of nitrilotriacetonitrile salt

Picolines, mixed

Condensation of acetaldehyde + formaldehyde + ammonia

Organic pigments, azo

Diazotization of aniline cogener, coupling to B-napthol

2-Isopropyl-4-methoxy-pyrimidines

Isobutyronitril + methanol, ammonia and methylacetoacetate,ring closure

Synthetic pyridine

Condensation of acetaldehyde + ammonia + formaldehyde

Cyanopyridine

Ammoxidation of picoline

Sarcosine (N-methyl glycine) sodium salt

Hexamethylene tetraamine + sodium cyanide, hydrolysis

Thiophene acetic acid

Chloromethylation (hydrogen chloride + formaldehyde) +

sodium cyanide, hydrolysis

Tris(anilino)S-triazine

Cyanuric chloride + aniline and its cogeners

Triethylorthoformate

Ethanol + hydrogen cyanide

Trimethylorthoformate

Methanol + hydrogen cyanide

Product

Process

Alkyd resin

Condensation polymerization

Alkyd resins

Condensation polymerization of phthalic anhydride + glycerin

+ vegetable oil esters

Dialkyldithiocarbamates, metal salts

Dialkylamines + carbon disulfide

Thiuram (dimethyldithiocarbamate) hexasulfide

Dimethyldithiocarbamate + sulfur

Triphenylmethane dyes (methyl violet)

Condensation of formaldehyde + N-methylaniline + N,N-dimethylaniline, oxidation of reaction product

4,4-Bis(N,N-dimethylaniline) carbinol, Michler's hydrol

Oxidation of 4,4-methanylene-bis(N,N-dimethylaniline) with lead oxide

Naphthenic acid salts

Stearic acid, metal salts

Neutralization with a metallic base

Product

Process

Acetates, 7,11-hexadecadien-1-ol (gossyplure)

Coupling reactions, low pressure hydrogenation, esterification

Acetates, 9-dodecen-1-ol pheromone

Coupling reactions, low pressure hydrogenation, esterification

Acrylic acid

Oxidation of propylene via acrolein

Acrylonitrile

Propylene ammoxidation

n-Alkanes

Hydrogenation of C6-C22 alpha olefins (ethylene oligomers)

Adiponitrile

Direct cyanation of butadiene

Alkyl amines

Amination of alcohols

4-Aminoacetanilide

Hydrogenation of 4-Nitroacetanilide

BTX

Hydrogenation of olefins (cyclohexenes)

Hydrogenated terphenyls

Nickel catalyst, hydrogenation of terphenyl

Bisphenol-A, hydrogenated (biscyclohexanol-A)

Hydrogenation of bisphenol-A

Butadiene (1,3)

Extractive distillation of C-4-pyrolyzates

n-Butanol

Hydrogenation of n-butyraldehyde, oxo process

1,3 Butylene glycol

Hydrogenation of acetaldol

1,4 Butanediol

Hydrogenation of 1,4 butynediol

Butylenes mixed

Distillation of C4 pyrolyzates

4-Chloro-2-aminophenol

Hydrogenation of 4-chloro-2-nitrophenol

Lilial (hydroxydihydrocitronellal)

Hydration and oxidation of citronellol

Cycloparaffins

Catalytic hydrogenation of aromatics in kerosene solvent

Cyclohexanol

Hydrogenation of phenol, distillation

Cyclohexanone

From phenol via cyclohexanol by hydrogenation-dehydrogenation

Dialkyldithiocarbamates, metal salts

Dialkylamines + carbon disulfide

Ethylamine

Reductive amination of ethanol

Ethylamines (mono, di, and tri)

Reductive amination (ammonia + hydrogen) of ethanol

Isoeugenol, high percent trans

Separation of mixed cis and trans isoeugenols

2-Ethylhexanol

From n-butyraldehyde by aldol condensation and hydrogenation

Hydrogenated fatty acids

Tallow and coco acids + hydrogen

Fatty amines

Batch hydrogenation of fatty nitriles

Fatty amines

Hydrogenation of tallow and coco nitriles

Glyoxal-urea formaldehyde textile resin

Condensation to N-bis(hydroxymethyl)ureas and N,N'-di(hydroxy-

ethyl) ureas

11-Hexadecenal

Coupling reactions, low pressure hydrogenation

Hexahydrophthalic anhydride

Condensation of butadiene and maleic anhydride (Diels-Alder reac-

tion) + hydrogenation

Isobutanol

Hydrogenation of isobutyraldehyde, oxo process

Diisobutyl amine

Ammonolysis of isobutanol

Isopropyl amines (mono, di)

Reductive amination (ammonia + hydrogen) of isopropanol

Linalool

Pyrolysis of 2-pinanol

Methanol

High pressure synthesis from natural gas via synthetic gas

Methanol

Low pressure synthesis from natural gas via synthetic gas

Methanol

Butane oxidation

Tris-(hydroxymethyl)methyl amine

Hydrogenation of tris(hydroxymethyl) nitromethane

N-Methyl morpholine

Morpholine + methanol

N-Ethyl morpholine

Morpholine + ethanol

2-Methyl-7,8-epoxy octadecane

Coupling reactions, low pressure hydrogenation, epoxidation

Alpha-olefins

Ethylene oligomer and Zeigler catalyst

Petroleum hydrocarbon resins, hydrogenated

Hydrogenation of petroleum hydrocarbon resin products

Pinane

Hydrogenation of A-pinene

2-Pinanol

Reduction of pinane hydroperoxide

Bis-(p-octylphenol)sulfide, nickel salt

p-Octylphenol + sulfur chloride (S2C12) neutralize with nickel base

Piperazine

Reductive amination of ethanol amine (ammonia and hydrogenation

metal catalyst)

N,N-Dimethylpiperazine

Condensation piperazine + formaldehyde hydrogenation

Polyoxyalkylene amines

Polyoxyalkylene glycol + ammonia

Polyoxypropylene diamine

Polypropylene glycol + ammonia

2-Amino-2-methyl-1-propanol

Hydrogenation of 2-nitro 2-methyl-1-propanol

3-Methoxypropyl amine

Reductive amination of acrylamide with methanol and hydrogen

N-Propylamine

Reductive amination (ammonia + hydrogen) of n-propanol

Sorbitol

Hydrogenation of sugars

Sulfolane

Condensation butadiene + sulfur dioxide, hydrogenation

Thionocarbamates, N-ethyl-o-isopropyl

Isopropyl xanthate + ethylamine

Toluene diamine (mixture)

Catalytic hydrogenation of dinitrotoluene

Methylated urea formaldehyde resins (textile)

Methylation of urea-formaldehyde adduct

Methylated urea-formaldehyde glyoxol (textile resins)

Reaction of methylated urea- formaldehyde + glyoxal

Product

Process

Methylhydroabietate, diels-alder adducts

Derivatives of abietic esters from rosin

Acrylic resins

Emulsion or solution polymerization to coatings

Acrylic resins (latex)

Emulsion polymerization of acrylonitrile with polybutadiene

Acrylic fibers (85% polyacrylonitrile)

By solution polymerization/wet spinning

Alkyd resins

Condensation polymerization of phthalic anhydride + glycerin +

vegetable oil esters

Benzene

By-product of styrene by ethyl- benzene dehydrogenation

Benzene

Byproduct of vinyl toluene from ethyl toluene

n-Butyl alcohol

Hydrogenation of n-butyraldehyde, oxo process

Coumarin (benz-a-pyrone)

Salicylaldehyde, Oxo process

Cycloparaffins

Catalytic hydrogenation of aromatics in kerosene solvent

Dithiocarbamates, zinc salt

Reaction of zinc oxide + sodium dithiocarbamates

Dialkyldithiocarbamates, metal salts

Dialkylamines + carbon disulfide

Dithiocarbamates, metal salts

Dithiocarbamic acid + metal oxide

Thiuram (dimethyldithiocarbamate) hexasulfide

Dimethyldithiocarbamate + sulfur

Fluorescent brighteners

Coumarin based

Ethyl acetate

Redox reaction (Tschenko) of acetaldehyde

Ethylbenzene

Benzene alkylation in liquid phase

Ethylbenzyl chloride

Chloromethylation (hydrogen chloride + formaldehyde, zinc chloride)

of ethylbenzene

2-Ethyl hexanol

Aldol condensation-hydrogenation of n-butyraldehyde

Glyoxal-urea formaldehyde textile resin

Condensation to N-bis (hydroxymethyl) ureas + N,N'-(dihydroxye-

thyl) ureas

Isobutanol

Hydrogenation of isobutyraldehyde, Oxo process

Isopropanol

Catalytic hydrogenation of acetone

Methallylidene diacetate

Condensation of 2-methypropenal + acetic anhydride

Methanol

Low pressure synthesis from natural gas via synthetic gas

Methyl chloride

Hydrochlorination of methanol

Methylethyl ketone

Dehydrogenation of sec-butanol

Naphthenic acid salts

Nylon

Nylon 6 and 66 copolymers

Polycondensation of nylon salt + caprolatam

Nylon 6 fiber

Extrusion melt spinning

C12-C15 oxo alcohols

Hydroformylation and hydrogenation of C11-C14 olefins

Phenolic urethan resins

Phenol + excess formaldehyde + methylene aniline diisocyanate

Polystyrene crystal modified

Polystyrene + sulfonation, Chloromethylation and/or amination

Rayon

Viscose process

SAN resin

Emulsion polymerization

Silicone rubbers

Hydrolysis and condensation of chlorosilanes

Silicone specialties, such as grease, dispersion agents,

defoamers, and other products

Silicone resins

Hydrolysis and condensation of methyl, phenyl, and vinyl chlorosi-

lanes

Silicone fluids

Hydrolysis of chlorosilanes to acyclic and cyclic organosiloxanes

Neutralization with a metallic base

Stearic acid, metal salts

Neutralization with a metallic base

Styrene

Dehydrogenation of ethylbenzene

Styrene-butadiene resin

Emulsion polymerization

Vinyl acetate

Reduction of acetylene + acetic acid

Vinyl toluene

Thermal dehydrogenation of ethyltoluene

Xylenes, mixed

By-product vinyl toluene from ethyltoluene

State Code

Code of Federal Regulations

s. NR 205.03

40 CFR 401.11

s. NR 205.04

40 CFR 401.11

ch. NR 211

40 CFR Part 403

s. NR 211.03

40 CFR 403.3

s. NR 211.13

40 CFR 403.7

s. NR 211.14

40 CFR 403.17

ch. NR 235

40 CFR Part 414