Wis. Admin. Code Department of Natural Resources, NR 200-299, ch. NR 235, subch. XI, app A to CHAPTER NR 235
Chromium 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 |
Copper Bearing Waste Streams
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 |
WISCONSIN ADMINISTRATIVE CODE
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 |
Lead Bearing Waste Streams
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 |
Nickel Bearing Waste Streams
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 |
Zinc Bearing Waste Streams
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 |
Note: The Wisconsin administrative code corresponds to the code of federal regulations according to the following table
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 |
Wis. Admin. Code Department of Natural Resources, NR 200-299, ch. NR 235, subch. XI, app A to CHAPTER NR 235