TABLE OF CONTENTS

SUMMARY

This document is one in a series that establishes ambient water quality guidelines for British Columbia. The Canadian Council of Ministers of the Environment (CCME) has recently developed new guidelines of 4 ug/L for mono and dihydric phenols to protect freshwater aquatic life. The Ministry has published guidelines for chlorophenols, but needed to evaluate the CCME guidelines to decide which phenols were to be included as total phenols. Another factor that raised the priority of this review was that the Ministry is undertaking a Stage 2 Contaminated Sites Regulation amendment.

Suitable data documenting the effects of phenols for most water uses is lacking, therefore, we have only derived guidelines to protect aquatic life. Due to time and data constraints, and since the Ministry has guidelines for chlorinated phenols, this document only recommends working water quality guidelines for non-halogenated phenols to protect freshwater aquatic life. These working guidelines will need to be converted to more scientifically defensible guidelines when time and data permit.

At extremely low phenol values, there are two effects apparent in phenol-contaminated waters:

1. toxicity to aquatic life, and
2. the generation of an unpleasant taste in fish and shellfish.

The data on which these working guidelines for phenols are based are summarized in tables in the appendices to this report.

The working water quality guidelines are summarized in Table 1.

TABLES

• Table 1. Summary of Water Quality Guidelines for Phenol
• Table 2. The Lowest Reliable Freshwater Toxicity Data for Various Phenols
• Table 3. Aquire Database Unverified Records of Phenol Acute Toxicity
• Table 4. Nominal LC₅₀ for 24 Hour Old Artemia salina
• Table 5. Nominal 24 Hour LC₅₀ for Artemia salina
• Table 6. Nominal LC₅₀ for 24 Hour Old Daphnia magna in Hardness 173 mg/L Water
• Table 7. Aquatic Organisms: LC₅₀ to Phenol
• Table 8. Fathead Minnow (Pimphales promelas) 96 Hour Phenol Assays
• Table 9. Aquatic Organisms: EC₅₀ and other Non-Lethal Effects of Phenol
• Table 10. Environment Canada Data for Phenol, Acute LC₅₀ Freshwater Data
• Table 11. Environment Canada Data for Phenol, Chronic Freshwater Data
• Table 12. Environment Canada Data for Phenol, Acute LC₅₀ Marine Data
• Table 13. Shrimp (Crangon septemspinosa) and Clam (Mya arenaria) Toxicity in mg/L
• Table 14. Phenol and Resorcinol 96 Hour LC₅₀ Data
• Table 15. Aquatic Organisms: 96 Hour LC₅₀ Phenol Data in mg/L
• Table 16. Amphibians: 96 Hour LC₅₀ Phenol Data in mg/L
• Table 17. Rainbow Trout (Oncorhynchus mykiss): 96 Hour LC₅₀ Phenol Data in mg/L
• Table 18. Fathead Minnow (Pimphales promelas): 96 Hour LC₅₀ Phenol Data in mg/L
• Table 19. Rainbow and Fathead 96 Hour LC₅₀ and Daphnia 48 Hour LC₅₀ Phenol Data in mg/L
• Table 20. 24 Hour Phenolics Bioassays with Daphnia magna in mg/L
• Table 21. 48 Hour Phenolics Bioassays with Daphnia magna in mg/L
• Table 22. 48 Hour Resorcinol Bioassay with Daphnia pulex in mg/L
• Table 23. Hydroquinone and Phenol Bioassays in mg/L
• Table 24. 48 Hour o-cresol Bioassays with Daphnia in mg/L
• Table 25. 24 Hour Phenolics Bioassays with Daphnia magna and Brachydanio rerio in mg/L

PREFACE

THE MINISTRY OF WATER, LAND AND AIR PROTECTION develops ambient water quality guidelines for British Columbia. This work has two goals:

1. to provide guidelines for the evaluation of data on water, sediment and biota
2. to provide a basis for setting site-specific ambient water quality objectives.

The guidelines represent safe conditions or safe levels of a substance in water. The term guideline is defined as:

Water Quality guidelines are applied province-wide, but they are use-specific, and are being developed for these water uses:

• Raw drinking, public water supply and food processing
• Aquatic life and wildlife
• Agriculture (livestock watering and irrigation)
• Recreation and aesthetics
• Industrial (water supplies)

The guidelines are established following a thorough review of the recent scientific literature, guidelines set by other jurisdictions and environmental conditions in British Columbia. The scientific literature provides information on environmental fate, persistence and effects of toxicants on various life forms. This information is not always conclusive because it is often based on laboratory testing that, at best, only approximates field conditions. To compensate for this uncertainty, and applying the precautionary principle, the guidelines have built-in safety factors that are conservative, while taking into account the natural background in the province. The guidelines are used to set ambient site-specific water quality objectives for specific waterbodies. In setting the objectives, considerations are given to present and future water uses, waste discharges, hydrology, limnology, oceanography and ambient water quality conditions at the site in question.

In most cases the objectives are the same as the guidelines. However, when natural background levels of substances exceed the guidelines, the site-specific objective could be less stringent than the guideline in order to take this high natural level into account. In rare instances for example if the resource is unusually valuable or of special provincial or ecological significance the safety factor could be increased enabling objectives to be more stringent than the guidelines. Another approach would be to develop site-specific objectives by conducting toxicity experiments in the field. However, because this approach is costly and time consuming, it is seldom used.

Neither the guidelines nor the objectives derived from them have any legal standing. However, objectives can be used to calculate waste discharge limits for contaminants. These limits are outlined in waste management permits, orders and approvals, all of which have legal standing. Objectives are not usually incorporated as conditions of a permit.

Water quality guidelines are subject to review and revision, as new information becomes available or as other circumstances dictate.

INTRODUCTION

PHENOLS

In chemical terminology, a phenol is a single aromatic ring organic compound with an -OH group. An alkyl, straight chain or ring, organic compound with an -OH group is an alcohol. A double aromatic ring organic compound with an -OH group is a naphthol.

Phenol, formerly called carbolic acid, is an aromatic organic compound, C₆H₅OH. It is weakly acidic and resembles an alcohol in structure. The colourless, needlelike crystals of purified phenol melt at 43°C (109°F) and boil at 182°C (360°F). Phenol is soluble in organic solvents and slightly soluble in water at room temperature, and completely soluble above 66°C (150.8°F). It is a constituent of coal tar.

Phenol was first used as a disinfectant in 1867 by the British surgeon Joseph Lister for sterilizing wounds, surgical dressings, and instruments. Dilute solutions are useful antiseptics, but strong solutions are corrosive and scarring to tissue. Less irritating and more efficient germicides have replaced phenol, but it is widely used in the manufacture of resins, plastics, insecticides, explosives, dyes, and detergents. It is also used as a raw material for the production of medicinal drugs such as aspirin.

The term phenol is also used for any of a group of related acidic compounds that are hydroxyl derivatives of aromatic hydrocarbons. These include such substances as cresol, catechol, quinol, xylenol, guaiacol and resorcinol. For consistency and clarity these are all named as substituted phenols in this document. See Appendix 1 for a partial list of some phenol compounds.

The latest CCME document combines all of the 1- and 2-hydric phenols together into one group for setting guidelines based on toxicity. We have followed the same procedure for establishing these working guidelines with the exception of setting separate guidelines for 4-hydroxyphenol (hydroquinone) and 3-hydroxyphenol (resorcinol). There are several reasons for this.

There can be large differences in the toxicity of the various distinct phenol compounds, particularly when the substituents are strong electron donors or sinks. This can lead to over-protection for some of these compounds because the guideline is established to accommodate the most toxic phenol.

There is a paucity of existing reliable data that can be used to set guidelines for individual compounds. The guidelines are set to account for the most toxic phenols. If circumstances warrant, it is recommended that dischargers carry out Water Effect Ratio trials with their specific effluent and their ambient water to determine an acceptable site-specific phenol concentration.

Toluene and the xylenes are not phenols in their un-substituted form. Toluene is 1-methyl benzene and the xylenes are: 1, 2-dimethyl benzene, 1, 3-dimethyl benzene or 1, 4-dimethyl benzene. However, if one of the other substitutions on the benzene ring is a hydroxy group, then they become a phenol, cresol or xylenol. Therefore, for example: 4-hydroxy toluene, 4-methyl phenol, 1-methyl-4-hydroxy benzene, and 1-hydroxy-4-methyl benzene are all the same compound, as are 3, 4-dimethyl phenol, 3, 4-dimethyl xylenol, 1-hydroxy-3, 4-dimethyl benzene and 2-methyl-4-hydroxy toluene.

One must be aware of all these alternate names when looking up data on phenol compounds. It is best to try to find one name in the Chemical Abstracts Service (CAS) registry that has a bewildering variety of alternate names listed. Using the substituted benzene or phenol nomenclature can reduce the ambiguity and confusion. In this document, we try to use only a few alternate names.

There are, in theory, an infinite number of phenols since up to 5 'R' groups (long-chain aliphatics) can be substituted and each of these can be very complex and substituted itself. In practice, there are far too many phenols to deal with individually but the toxic properties of many long-chain aliphatic substituted compounds will be quite similar. It is the toxicity of the phenols with simple substituents like methyl (-CH3), hydroxyl (-OH), amino (-NH2), nitro (-NO2), methoxy (-CH3O) and the halogens (-Cl, -Br, -I, -F) that are of most toxicological concern. Most phenols are used as bactericides, fungicides and herbicides; particularly the halogenated phenols, and especially the chlorinated halophenols.

The environmental half-lives of most phenols are short, rarely as long as a month. Some are photo-degraded, especially in air. The microbial half-life is short, typically measured in days under aerobic conditions. Once a discharge ceases, environmental levels will drop rapidly due to bacterial breakdown. The half-life of phenols in fish is less than one day and phenols do not accumulate. Hence the existence of high levels in fish tissues indicates chronic or current exposure.

Microorganisms will alter their metabolic processes to utilize phenols. If they have not previously been exposed there will be an initial adaptation period until a large microbial population has been established. Any subsequent additions of phenols will be quickly degraded.

RECOMMENDED GUIDELINES

The following guidelines are based on readily available existing information which is summarized in tables in Appendix 2. The Canadian Council of Ministers of the Environment (CCME) has set guidelines for all mono- and di-hydric phenols.

FRESHWATER AQUATIC LIFE

Aquatic Life is the only water use for which guidelines are being set in this document. They are working guidelines subject to revision when more complete data become available. The maximum concentration of 4-hydroxyphenol (quinol, hydroquinone, 1,4-benzenediol) should not exceed 2 micrograms/L. The maximum concentration of 3-hydroxyphenol (resorcinol, 1,3-benzenediol) should not exceed 12.5 micrograms/L, and the maximum concentration of the total of all other non-halogenated phenols should not exceed 50 micrograms/L.

RATIONALE

The lowest LC₅₀ data found for many phenols is presented in Table 2. The lowest effect for 4-hydroxyphenol (hydroquinone) was for Daphnia magna, at 0.04 mg/L. For 3-hydroxyphenol (resorcinol), the lowest effect level measured was at 0.25 mg/L, also forDaphnia magna. These were divided by a safety factor of 20:1 in order to estimate a safe minimal, or no effect, level for other freshwater species.

The next most toxic form of phenol was reported for fathead minnows, Pimphales promelas using 4-phenylazophenol at 1.17 mg/L. We have assumed that the sum of all other phenols present (non-chlorinated) should not exceed this level since there are many phenol compounds with similar toxicity (see Table 2).Therefore, for all other phenols, we divided this level by a factor of 20 to estimate the safe level.

APPLICATION OF GUIDELINES

Chlorophenols, hydroquinone and resorcinol should be measured separately and compared to their respective proposed guideline values. A measurement of total phenols minus the sum of total chlorophenols, hydroquinone, and resorcinol allows one to determine if the guideline for total phenols is met.

REFERENCES

• http://www.fwkc.com/encyclopedia/low/articles/p/p019001107f.html. Note: This link no longer works (Defines phenol)
• Barahona, M. V. and S. Sanchez-Fortun. 1996. Comparative Sensitivity of Three Age Classes of Artemia salina to Several Phenolic Compounds. Bull. Environm. Contam Toxicol. 56: 271-278.
• Black, J. A. et al. 1982. The Aquatic Toxicity of Organic Compounds to Embryo-Larval Stages of Fish and Amphibians. Research Report. University of Kentucky, Water Resources Research Institute, Lexington, Kentucky.
• Breton, Roger. 1998. Supporting Document for the Environmental Assessment of the Priority Substance Phenol. Canadian Environmental Protection Act. Environment Canada, Government of Canada.
• Brooke, L. T.. et al. 1984. Acute Toxicities of Organic Chemicals to Fathead Minnows (Pimephales promelas). Volume 1. Center for Lake Superior Environmental Studies. University of Wisconsin-Superior.
• Canton, J. H. et al. 1978. Reproducibility of short-term and reproduction toxicity experiments with Daphnia magna and comparison of the sensitivity of Daphnia magna with Daphnia pulex and Daphnia cucullata in short-term experiments. Hydrobiologia 59(2): 135-140.
• Crisinel, A. et al. 1994. Cyst-based ecotoxicological tests using Anostracans: Comparison of Two Species of Streptocephalus. Envir. Toxic. Water Quality. 9: 317-326.
• Degraeve, G. M. et al. 1980. Acute and Embryo-larval Toxicity of Phenolic Compounds. Arch. Environ. Contam Toxicol 9: 557-568.
• Devilliers et al. 1985. Intérêt de la relation dose-effet-temps en écotoxicologie pour la détermination des différentes classes chimiques de toxiques. Communication présentée au Congrès de l'AGHTM à Nancy, lors de la journée de la Commission d'Hydrologie Appliquée le 5 juin 1985.
• Environment Canada. 2000. Priority Substances List Assessment Report. Phenol. February 2000.
• Ewell, W. S. et al. 1986. Simultaneus Evaluation of the Acute Effects of Chemicals on Seven Aquatic Species. Environmental Toxicology and Chemistry (5): 831-840.
• Geiger, D. L. et al. 1988. Acute Toxicities of Organic Chemicals to Fathead Minnows (Pimephales promelas). Volume 4. Center for Lake Superior Environmental Studies. University of Wisconsin-Superior.
• Geiger, D. L. et al. 1986. Acute Toxicities of Organic Chemicals to Fathead Minnows (Pimephales promelas). Volume 3. Center for Lake Superior Environmental Studies. University of Wisconsin-Superior.
• Geiger, D. L. et al. 1985. Acute Toxicities of Organic Chemicals to Fathead Minnows (Pimephales promelas). Volume 2. Center for Lake Superior Environmental Studies. University of Wisconsin-Superior.
• LeBlanc, G. E. 1980. Acute Toxicity of Priority Pollutants to Water Flea (Daphnia magna). Bull. Environm. Contam Toxicol. 24: 684-691.
• McLeese, D. W. et al. 1979. Structure-Lethality Relationships for Phenols, Anilines and other Aromatic Compounds in Shrimp and Clams. Chemosphere (2): 53-57.
• Parkhurst, B. R. et al. 1979. An Evaluation of the Acute Toxicity to Aquatic Biota of a Coal Conversion Effluent and it Major Components. Bull. Environm Contam. Toxicol. 23: 349-356.
• Trabalka, J. R. et al. Investigation of the Effects of Halogenated Organic Compounds Produced in Cooling Systems and Process Effluents on Aquatic Organisms.
• Von Gottfried Bringmann et al. 1977. Befunde der Schadwirkung wassergefahrdender Stoffe gegen Daphnia magna. Z.f.Wasser-und-Abwasser-Forschung. 10 Jarhrgang. Nr.5/77.

Appendix 1. List of Phenols in commercial use.

This is a selected list of some of the phenols that are in commercial use and may be found in waste streams. There are many more phenols, some found only in natural products and not in commercial use. All will have their own distinct acute and chronic guideline levels.

Phenol (CAS #108-95-2)

The basic, simplest, parent compound is phenol, C₆H₆O. It is also called monohydroxy benzene, hydroxy benzene, benzenol, phenylic acid, phenyl hydroxide, benzophenol, phenyl hydrate, phenylic alcohol, monophenol, phenic acid, oxybenzene, hydroxy benzene or carbolic acid. Phenol can have a wide variety and number of substituents on the other five locations of the benzene ring.

Cresols

Cresols, C₆H₈O, are methyl phenols and have one methyl group in the ortho, meta or para (second, third or fourth, respectively) position on the parent phenol. The unsubstituted parent compounds are also called ortho: 1-hydroxy-2-methyl benzene, 2-methyl phenol, 2-hydroxy toluene, 1-methyl-2-hydroxy benzene; meta: 1-hydroxy-3-methyl benzene, 3-methyl phenol, 3-hydroxy toluene, 1-methyl-3-hydroxy benzene: para: 1-hydroxy-4-methyl benzene, 4-methyl phenol, 4-hydroxy toluene and 1-methyl-4-hydroxy benzene.

The CAS numbers of the parent compounds are: o-cresol (CAS #95-48-7), m-cresol (CAS #108-39-4) and p-cresol (CAS #106-44-5).

Guaiacol (CAS #90-05-1)

Guaiacols, C₇H₈O₂, have an ortho or 2-substituted methoxy on the parent phenol. They are o-methoxy hydroxybenzenes and the parent unsubstituted compound is also called 1-hydroxy-2-methoxy benzene, 2-methoxy phenol and guaiacol. These are natural wood digestion products and often have other substitutions on the other four sites.

Resorcinol (CAS #108-46-3)

Resorcinols, C₆H₆O₂, have a second meta or 3-substituted hydroxy on the parent phenol. They are m-dihydroxy benzenes and the parent unsubstituted compound is also called 1, 3-dihydroxy benzene, 3-hydroxy phenol, 1, 3-benzenediol and Resorcinol.

Catechol (CAS #120-80-9)

Catechols, C₆H₆O₂, have a second ortho or 2-substituted hydroxy on the parent phenol. They are o-dihydroxy benzenes and also called 1, 2-dihydroxy benzene, 2-hydroxy phenol, 1, 2-benzenediol, pyrocatechol and catechol.

Xylenols

Xylenols, C₈H₁₀O, are dimethyl phenols. They have two methyl groups and at least one hydroxy group. The methyls may be 1, 2-, 1, 3- or 1, 4- (ortho, meta and para respectively, relative to each other) and the hydroxyl can then be on any of the other four sites. This allows for 6 different possible isomers. Choosing one of the isomers at random, some of the names are 1-hydroxy-3, 4-dimethyl benzene, 1, 2-dimethyl-4-hydroxy benzene, 3, 4-dimethyl phenol, 3, 4-xylenol, 4-hydroxy-o xylene and 2-methyl-4-hydroxy-toluene.

The CAS numbers of the six parent compounds are: 2, 3-xylenol (CAS# 526-75-0), 2, 4-xylenol.(CAS# 105-67-9), 2, 5-xylenol (CAS #95-87-4), 2, 6-xylenol (CAS# 576-26-1), 3, 4-xylenol (CAS #95-65-8) and 3, 5-xylenol (CAS# 108-68-9).

Quinol or Hydroquinone (CAS #123-31-9)

Quinols or hydroquinones, C₆H₆O₂, have a second para or 4-substituted hydroxy on the parent phenol. They are p-dihydroxy benzenes and the parent unsubstituted compound is also called 1, 4-dihydroxy benzene, 4-hydroxy phenol, 1, 4-benzenediol, hydroquinone and quinol.

Naphthols

When there are two joined aromatic rings with a hydroxy group on at least one of them, the compound is called a naphthol and now there are seven more sites for substitution and the nomenclature gets a little more complex. However, we are only concerned with phenols in this document.

The CCME aquatic life guideline for mono-hydric phenols and di-hydric phenols, as a group, is 4 micrograms/L in fresh water; no guideline was set in marine water. Toxicity varies widely by organism, dissolved oxygen and temperature. The sequence of decreasing toxicities is generally phenol, p-cresol, o-cresol, m-cresol and catechol. A preliminary search of the internet did not turn up much aquatic toxicity data, primarily MSDS, Material Safety Data Sheet, and OSHA, Occupational Safety and Health, lab-rat data. Some reported acute and chronic toxicity values are listed in the tables in Appendix 2.

Phenol, o-cresol, m-cresol, p-cresol, 2, 3-xylenol, 2, 4-xylenol, 2, 5-xylenol, 2, 6-xylenol, 3, 4-xylenol, 3, 5 xylenol and all the derivatives of catechol, resorcinol and quinol have low vapour pressures, under one kPa and high water solubilities, in the grams per litre range. Oxidation and microbial degradation are the main fates of phenols in the environment. Sorption is low as are log Kow values; generally under 2.0, reaching only 2.5 as a maximum.

Some simple substituted phenols

• 2-nitrophenol CAS #88-75-5, o-nitrophenol
• 4-nitrophenol CAS #100-02-7, p-nitrophenol
• 3-nitrophenol CAS #554-84-7, m-nitrophenol
• dinitrophenols (mixture) CAS #25550-58-7
• nitrophenols (all isomers) CAS #25154-55-6
• 4-nitrophenol sodium salt CAS #824-78-2
• 4-methoxyphenol CAS #150-76-5
• 2, 4-dinitrophenol CAS #51-28-5
• 2, 5-dinitrophenol CAS #329-71-5
• 2, 6-dinitrophenol CAS #573-56-8
• 2-methoxy-5-nitrophenol CAS #67233-85-6
• 2-nitrophenol sodium salt CAS #824-39-5
• 4-amino-2-nitrophenol CAS #119-34-6
• 4-carboxyphenol CAS #99-96-7
• 2, 4-dimethylphenol CAS #105-67-9
• 2, 6-dimethylphenol CAS #576-26-1
• 2, 6-dinitro-4-methylphenol CAS #609-93-8
• dinitrobutylphenol CAS #88-85-7
• 2,6-dibromo-4-nitrophenol CAS #99-28-5
• p-methylaminophenol CAS #150-75-4
• 2, 4, 6-trinitrophenol CAS #88-89-1
• 3-phenylphenol CAS #580-51-8
• 2-phenylphenol CAS #90-43-7

• 4, 6-dinitro-o-cresol CAS #534-52-1, 2-methyl-4, 6-dinitro phenol
• p-chloro-m-cresol CAS #59-50-7, 4-chloro-3-methyl phenol, 4-chloro-m-cresol, 4-chloro-3-cresol
• 4-chloro-o-cresol CAS #1570-64-5, 4-choloro-2-cresol, 4-chloro-2-methyl phenol, p-chloro-o-cresol
• 4, 6-diamino-o-cresol CAS #15872-73-8, 4, 6-diamino-2-cresol
• 2, 6-dinitro-p-cresol CAS #609-93-8, 2, 6-dinitro-4-cresol
• 2-nitro-4-cresol CAS #119-33-5, 2-nitro-p-cresol, o-nitro-p-cresol, o-nitro-4-cresol
• hexahydro cresol CAS #25639-42-3
• 4-methyl-m-cresol CAS #95-87-4, 4-methyl-3-cresol
• 2-methyl-p-cresol CAS #104-93-8, 2-methyl-4-cresol

• tetrachloro guaiacol CAS #2539-17-5

• 4, 5-dichloro catechol CAS #3428-24-8
• tetra bromo catechol CAS #488-47-1
• tetra chloro catechol CAS #1198-55-6

• 4-chloro-m-xylenol CAS #88-04-0, 4-chloro-3, 5-xylenol, p-chloro-m-xylenol, p-chloro-3, 5-xylenol
• 4-amino-3, 5-xylenol CAS #3096-70-6

Some complex R group substituted phenols

• 2-cyclohexyl-4, 6-dinitro-phenol CAS #131-89-5
  Dinex-111
• 2-(1-methylethoxy)-phenol CAS #114-26-1
  Methylcarbamate
  Baygon
  Propoxur
• 2, 4-di-(m-xylenol) dimethyl phenol CAS #105-67-9
• 3, 5-dimethyl-4-(methylthio)-phenol CAS #2032-65-7
  methylcarbamate
  methyl-carbamic acid
  4-(methylthio)-3, 5-xylyl ester
  Mesurol
  Methiocarb
  Mercaptodimethur
• sodium o-phenylphenol CAS #132-27-4
  2-hydroxybiphenyl sodium salt
  Dowicide A, [1,1'-biphenyl]-2-ol sodium salt
• 4, 4'-(1-methylethylidene) bis-phenol CAS #80-05-7
  4, 4'-isopropylidene diphenol
  Bisphenol A
• 4, 4'-(1, 2-diethyl-1, 2-ethenediyl) bis, (E)-phenol CAS #56-53-1
  diethylstilbestrol
  stilbestrol
  DES
  alpha, alpha'-diethylstilbenediol
• 2-(1-methylpropyl)-4, 6-dinitro-phenol CAS #88-85-7
  Dinoseb
  2-sec-butyl-4, 6-dinitrophenol
  DNBP
• 2-(1, 3-dioxolan-2-yl)-phenol CAS #6988-21-2
  Methylcarbamate
  Elocron
  Famid
  Dioxacarb
  2-(1, 3-Dioxolan-2-yl)phenyl methylcarbamate
• 2, 4-diaminophenol di-hydrochloride CAS #137-09-7
• 3-(1-methylethyl)phenol methylcarbamate CAS #64-00-6
• 4, 4'-isopropylidenebis 2, 6-dichlorophenol CAS #79-95-8
• 4-(1, 1-dimethylpropyl)phenol sodium salt CAS #31366-95-7
• 4-chloro-2-(phenylmethyl)phenol potassium salt CAS #35471-49-9
• 4-chloro-2-(pheylmethyl)phenol sodium salt CAS #3184-65-4
• 4-nitro-3-(trifluoromethyl)phenol CAS #88-30-2
• heptenylated phenol CAS #72624-02-3
• isobutylated methylstyrenated phenol CAS #68457-74-9
• methyl phenol patassium salt CAS #12002-51-6
• thiobis (tetrapropylene) phenol (9ci) CAS #68815-67-8
• benziocarb phenol CAS #28987-17-9
• 2-benzyl-4, 6-dichlorophenol EDF #335
• 2, 4-bis (1,1-dimethylpropyl)phenol CAS #120-95-6
• 2, 4-bis (1-methyl-1-phenylethyl)-6-((2-nitrophenyl) azo) phenol CAS #70693-50-4
• 2, 4-bis (dimethylaminomethyl)phenol CAS #5424-54-4
• 2, 6-ditert-butylphenol CAS #128-39-2
• 2, 4-diamino-6-methylphenol hydrochloride CAS #65879-44-9
• 3-(diethylamino)phenol CAS #91-68-9
• 4-(3, 4-dihydro-2, 2, 4-trimethyl-2H-1-benzopyran-4-yl) phenol CAS #472-41-3
• 2, 4-dimethyl-3-(chloromethyl)-6-tertbutylphenol CAS #23500-79-0
• 2, 6-dimethyl-4-heptylphenol CAS #25154-52-3
• 2-(1, 1-dimethyl)-5-methyphenol CAS #88-60-8
• 2-(1, 1-dimethylethyl)phenol CAS #88-18-6
• 2, 4-dinitro-6-cyclohexylphenol CAS #131-89-5
• dinonylphenol CAS #1323-65-5
• dodecylphenol CAS #27193-86-8
• 4-dodecylphenol CAS #104-43-8
• 2-formylphenol CAS #90-02-8
• 2-(2H-benzotriazol-2-yl)-4, 6-bis(1-methyl-1-phenylethyl) phenol CAS #70321-86-7
• 2-(2H-benzotriazol-2-yl)-4, 6-ditertpentylphenol CAS #25973-55-1
• 4, 4'-isopropylidene-bis(2-tertbutylphenol CAS #79-96-9
• 4, 4'-isopropylidenediphenol CAS #80-0507
• 4, 4'-isopropylidinebisphenol disodium salt CAS #2444-90-8
• magnesium thiobis(tetrapropenylphenolate CAS #68974-78-7
• 2-methoxy-4-formylphenol CAS #121-33-5
• 4-(methoxycarbonyl)phenol CAS #99-76-3
• (1-methyl-1-phenylethyl)phenol CAS #27576-86-9
• 4-(methylanino)phenolsulphate CAS #55-55-0
• 2, 2'-methyenebis (4-methyl-6-nonylphenol) CAS #7786-17-6
• (1-methylethyl)phenol CAS #25168-06-3
• 3-methyloxyphenol CAS #150-19-6
• n-stearoyl-p-aminophenol CAS #103-99-1
• 6-((2-nitrophenyl)azo)-2, 4-ditertpentylphenol CAS #52184-19-7
• 4-nonylphenol CAS #104-40-5
• o-sec-butylphenol CAS #89072-5
• ortho-benzyl-p-chlorophenol CAS #120-32-1
• p-hexylphenol CAS #2446-69-7
• p-tertamylphenol CAS #80-46-6
• p-amylphenol potassium salt CAS #53404-18-5
• 2, 2', 6, 6'-tetra-tertbuty-4, 4'-methylenediphenol CAS #118-82-1
• 2, 2', 6, 6'-tetrabromo-4, 4'-isopropylidenephenol CAS #79-94-7
• 4-(1, 1, 3, 3-tetramethylbutyl)phenol CAS #140-66-9
• (1, 1, 3, 3-tetramethylbutyl)phenol CAS #27193-28-8
• 2, 2'-thiobis (4, 6-dichloro)phenol CAS #97-18-7
• 2, 4, 6-tri(dimethylaminomethyl)phenol CAS #90-72-2
• 2, 4, 6-tri (tertbutyl)phenol CAS #732-26-3
• zinc phenolsulphonate CAS #127-82-2

• 2-((o-nitrophenyl) azo)-p-cresol CAS #1435-71-8
• 2, 6-di-tertbutyl-p-cresol CAS #128-37-0
  2, 6-di-tertbutyl-4-cresol
• 4-chloro-alpha-phenyl-o-cresol CAS #120-32-1
• 3-amino-p-cresol methyl ether CAS #120-71-8
  m-amino-p-cresol methyl ether
• 2-(2H-benzotriazol-2yl)-p-cresol CAS #2440-22-4
• 3, 3', 3", 5, 5', 5"-hexa-tert-butyl-alpha, alpha', alpha"-(mesitylen-E2, 4, 6, -triyl) tri-p-cresol CAS #1709-70-2
• 6-isopropyl-m-cresol CAS #89-83-8
  6-isopropyl-3-cresol
• 6-tert-butyl-m-cresol CAS #88-60-8
  6-tert-butyl-3-cresol
• 4, 4'-thiobis (6-tert-buty-m-cresol CAS #96-69-5
  4, 4'-thiobis (6-tert-buty-3-cresol
• 4-(dimethylamino)-m-cresol methylcarbamate ester CAS #2032-59-9
  4-(dimethylamino)-3-cresol methylcarbamate ester
• 4-(methylthio)-m-cresol o, o-dimethyl phosphorothioate ester CAS #55-38-9
  4-(methylthio)-3-cresol o, o-dimethyl phosphorothioate ester
• 4-nitro-m-cresol o, o-dimethyl phosphorothioate ester CAS #55-38-9
  4-nitro-3-cresol o, o-dimethyl phosphorothioate ester
• 2, 2'-methylenebis (6-(1, 1-dimethylethyl)-p-cresol) CAS #119-47-1
  2, 2'-methylenebis (6-tert-butyl-p-cresol)
• 2, 2'-methylenebis (6-nonyl-p-cresol) CAS #7786-47-1
• o, o'-di-tert-butyl-p-cresol CAS #128-37-0
• o-cresol glycidyl ether CAS #2210-79-9
• p-cresol glycidyl ether CAS #26447-14-3
• 6, 6'-thiobis (4-chloro-o-cresol CAS #4418-66-0
• 2-((o-nitrophenyl) azo)-p-cresol CAS #1435-71-8
• o-tert-buty-p-cresol CAS #2409-55-4
  2-tert-buty-p-cresol
• alpha, alpha', alpha"-(2, 4, 6-trimethyl-s-phenyl) tris-2, 6-di-tert-butyl-p-cresol CAS #1709-70-2

• Allyl guaiacol CAS #97-53-0

• Resorcinol methyl ether CAS #150-19-6
• 4-benzoyl resorcinal CAS #131-56-6
  4-benzo resorcinol
• cresol-resorcinol di-isocyanate CAS #584-84-9
• 1, 3-bis (2, 3-epoxy) propyl resorcinol CAS #101-90-6
  resorcinol di-glycidyl ether
  resorcinol bis (2, 3-epoxy propyl) ether

• p-tert-butyl catechol CAS #98-29-3
  4-tert-butyl catechol
• 4-allyl catechol-2-methyl ether CAS #97-53-0
• allyl catechol methylene ether CAS #94-59-7
  4-allyl pyrocatecol formaldehyde acetyl
• 4-propenyl catechol methylene ether CAS #120-58-1

• 4-(dimethylamino)-3, 5-xylenol methyl carbamate ester CAS #315-18-4
• 6-tert-butyl-3-(chloromethyl)-2, 4-xylenol CAS #23500-79-0
• 4-(methylthio)-3, 5-xylenol methyl carbamate CAS #2032-65-7

Appendix 2. Aquire data-base phenol toxicity values.

The lowest AQUIRE data base values for the various phenol groups range from 0.044 to 25.9 mg/L, three orders of magnitude. Using a standard acute to chronic ratio of 20 leads to guideline values from 2.2 to 1300 micrograms/L or 0.0022 to 1.30 mg/L. The CCME 1999 Guideline to protect aquatic life from mono and dihydric phenols is 4 micrograms/L. Setting the guideline to protect the most sensitive species from the most toxic phenol leads to gross overprotection for some species and some phenols. This AQUIRE data is for the un-substituted parent phenols of each group. The toxic values will change as hydroxy, nitro, amino, methyl, methoxy and other 'R' groups are substituted, at various places and in various numbers and combinations, onto the parent phenol of each group.