Proposed Risk Management Approach for Phenol, 2,4,6-tris(1,1-dimethylethyl) (2,4,6-tri-tert–butylphenol) Chemical Abstracts Service Registry Number (CAS RN) 732-26-3
Environment Canada
Health Canada
January 2009
- Issue
- Background
- Why we need action
- Current used and industrial sectors
- Presence in the canadian environment and exposure sources
- Overview of existing actions
- Considerations
- Proposed objectives
- Proposed risk management
- Consultation approach
- Next steps / Proposed timeline
- References
This proposed risk management approach document builds on the previously released risk management scope document for 2,4,6-tri-tert–butylphenol, and outlines the proposed control actions for this substance. Stakeholders are invited to submit comments on the content of this proposed risk management approach or provide other information that would help to inform decision making. Following this consultation period, the Government of Canada will initiate the development of the specific risk management instrument(s) where necessary. Comments received on the proposed risk management approach will be taken into consideration in developing the instrument(s). Consultation will also take place as instrument(s) are developed.
The Canadian Environmental Protection Act, 1999(CEPA 1999) (Canada 1999) requires the Minister of the Environment and the Minister of Health (the Ministers) to categorize substances on theDomestic Substances List (DSL). Categorization involves identifying those substances on the DSL that are a) considered to be persistent (P) and/or bioaccumulative (B), based on the criteria set out in the Persistence and Bioaccumulation Regulations, and “inherently toxic” (iT) to humans or other organisms; or b) present, to individuals in Canada, the greatest potential for exposure (GPE). In addition, the Act requires the Ministers to conduct screening assessments of substances that meet the categorization criteria. The assessment further determines whether the substance meets the definition of “toxic” set out in section 64 of CEPA 1999.
In December 2006, the Challenge identified 193 chemical substances through Categorization which became high priorities for assessment due to their hazardous properties and their potential to pose risks to human health and the environment. In February 2007, the Ministers began publishing, for industry and stakeholder comment, profiles of batches containing 15 to 30 high-priority substances.
In addition, the information-gathering provisions under section 71 of CEPA 1999 are being used under the Challenge to gather specific information where it is required. The information that is collected through the Challenge will be used to make informed decisions and appropriately manage any risks that may be associated with these substances.
The substance Phenol, 2,4,6-tris(1,1-dimethylethyl), Chemical Abstracts Service Registry Number (CAS RN)1 732-26-3, referred to throughout this document by “2,4,6-tri-tert–butylphenol,” was included in Batch 2 of the Challenge under the Chemicals Management Plan.
A notice summarizing the scientific considerations of a final screening assessment report was published by Environment Canada and Health Canada in the Canada Gazette, Part I, for 2,4,6-tri-tert–butylphenol on January 31, 2009, under subsection 77(6) of CEPA 1999. The final screening assessment report concluded that 2,4,6-tri-tert–butylphenol is entering or may be entering the environment in a quantity or a concentration or under conditions that have or may have an immediate or long-term harmful effect on the environment or its biological diversity.
The final screening assessment report also concluded that 2,4,6-tri-tert–butylphenol meets the criteria for persistence and meets the criteria for bioaccumulation, as defined by the Persistence and Bioaccumulation Regulations made under CEPA 1999. The presence of 2,4,6-tri-tert–butylphenol in the environment results primarily from human activity.
For further information on the final screening assessment report conclusion for 2,4,6-tri-tert–butylphenol, refer to the final screening assessment report, available at www.chemicalsubstanceschimiques.gc.ca/challenge-defi/batch-lot_2_e.html.
Following a screening assessment of a substance under section 74 of CEPA 1999, a substance may be found to meet the criteria under section 64 ofCEPA 1999. The Ministers can propose to take no further action with respect to the substance, add the substance to the Priority Substances List (PSL) for further assessment, or recommend the addition of the substance to the List of Toxic Substances in Schedule 1 of CEPA 1999. Under certain circumstances, the Ministers must make a specific proposal either to recommend addition to the List of Toxic Substances or to recommend the implementation of virtual elimination (or both). In this case, the Minister proposed to recommend the addition of 2,4,6-tri-tert–butylphenol to the List of Toxic Substances in Schedule 1 of CEPA 1999. As a result, the Ministers will develop a regulation or instrument respecting preventive or control actions to protect the health of Canadians and the environment from the potential effects of exposure to this substance.
The final screening assessment report concluded that 2,4,6-tri-tert–butylphenol meets the virtual elimination criteria set out in subsection 77(4) of CEPA 1999 because
- 2,4,6-tri-tert–butylphenol meets the criteria under section 64 of CEPA 1999; and
- 2,4,6-tri-tert–butylphenol meets the criteria for persistence and bioaccumulation as defined by the Persistence and Bioaccumulation Regulations made under CEPA 1999; and
- the presence of 2,4,6-tri-tert–butylphenol in the environment results primarily from human activity; and
- 2,4,6-tri-tert–butylphenol is not a naturally occurring radionuclide or a naturally occurring inorganic substance.
As a result, the Government of Canada will follow the process specified in CEPA 1999 for substances that meet the criteria for virtual elimination.
2,4,6-tri-tert–butylphenol is part of the chemical grouping discrete organics and the chemical sub grouping alkylphenols.
Table 1 presents other names, trade names, chemical groupings, the chemical formula, the chemical structure, and the molecular mass for 2,4,6-tri-tert–butylphenol.
| Chemical Abstracts Service Registry Number (CASRN) | 732-26-3 |
|---|---|
| Name on Domestic Substances List (DSL) | Phenol, 2,4,6-tris(1,1-dimethylethyl)- |
| National Chemical Inventories (NCI) names2 | Phenol, 2,4,6-tris(1,1-dimethylethyl)-(TSCA, ENCS,AICS,PICCS,ASIA-PAC) 2,4,6-Tri-tert-butylphenol (DSL, EINECS,PICCS) 2,4,6-Tris(1,1-dimethylethyl)phenol (ECL) 2,4,6-TRI-TERT-BUTYL PHENOL (PICCS) |
| Other names | 2,4,6-Tri-t-butylphenol; 2,4,6-Tri-tert-butyl-1-hydroxybenzene; 2,4,6-Tris(tert-butyl)phenol; Alkofen B; NSC 14459; P 23; P 23 (phenol); Phenol, 2,4,6-tri(1,1-dimethylethyl)-; Phenol, 2,4,6-tri-tert-butyl-; TM 02; Tri-tert-butylphenol; Voidox |
| Chemical group (DSLStream) |
Discrete organics |
| Major chemical class or use | Phenols |
| Major chemical sub-class | Alkylphenols |
| Chemical formula | C18H30O |
| Chemical structure |  |
| SMILES | Oc(c(cc(c1)C(C)(C)C)C(C)(C)C)c1C(C)(C)C |
| Molecular mass | 262.44 g/mol |
Evidence that a substance is highly persistent and bioaccumulative as defined in the Persistence and Bioaccumulation Regulations of CEPA 1999 (Canada 2000), when taken together with the potential for environmental release or formation and the potential for toxicity to organisms, provides a significant indication that it may be entering the environment under conditions that may have harmful long-term ecological effects (Environment Canada 2006). Substances that are persistent remain in the environment for a long time after being released, increasing the potential magnitude and duration of exposure. Substances that have long half-lives in mobile media (air and water) and partition into these media in significant proportions have the potential to cause widespread contamination. Releases of small amounts of bioaccumulative substances may lead to high internal concentrations in exposed organisms. Highly bioaccumulative and persistent substances are of special concern, since they may biomagnify in food webs, resulting in very high internal exposures, especially for top predators.
The importation volumes of 2,4,6-tri-tert-butylphenol into Canada along with its broad use indicate the potential for releases into the Canadian environment. Information gathered to date indicates that the only use of the substance is as a fuel additive. However, 2,4,6-tri-tert-butylphenol has been used in the past in Canada as a lubricant additive, and this is a recognized use for the substance elsewhere. As a result, the calculations used to make assumptions for releases include a minor use of the substance as a lubricant additive. Results from the Mass Flow Tool suggest that up to 2% of the total mass of the substance in commerce is released into the environment, with the vast majority being transformed (i.e., destroyed during combustion). Both empirical and modeled data indicate that once this substance is released into the environment it will remain in water, sediment and soil for a long time because of its stability in the environment. Due to its lipophilic character and persistence, the empirical and modelled data suggest that it will likely bioaccumulate and may biomagnify in trophic food chains. Both empirical and modelled data have also demonstrated the potential for relatively high toxicity to aquatic organisms. This information suggests that 2,4,6-tri-tert-butylphenol has the potential to be released into the environment and cause ecological harm in Canada (Environment Canada and Health Canada 2008b).
The primary end-use application of 2,4,6-tri-tert-butylphenol is as an antioxidant in hydrocarbon fuels such as gasoline, jet fuel, diesel and biodiesel. Antioxidants are added to stabilize fuels and prevent polymerization that leads to the formation of engine-fouling residues. A technical study completed by Cheminfo Services Inc. (Environment Canada 2008) estimated that the concentration of 2,4,6-tri-tert-butylphenol in fuel additives varied from 11% to 15%. In general, petroleum fuel additives are primarily used at concentrations well below 1% volume in the fuel. The resulting concentration of 2,4,6-tri-tert-butylphenol found in fuels would therefore be extremely low.
Based on the information collected by Environment Canada between 1986 and 2007, there appears to be a decreasing trend in the quantity of this substance either manufactured, imported or in commerce during this time.
The quantity reported to be manufactured, imported or in commerce in Canada during the calendar year 1986 was between 1 000 000 and 10 000 000 kg (Environment Canada 1988). There were fewer than four notifiers for the calendar years 1984 to 1986.
As a result of a survey conducted under section 71 ofCEPA 1999 for the year 2000, it was determined that the substance 2,4,6-tri-tert-butylphenol was not manufactured in Canada in the year 2000 in a quantity exceeding the 100-kg reporting threshold. Fewer than ten companies reported importing a combined total of between 10 000 and 100 000 kg of 2,4,6-tri-tert-butylphenol into Canada in 2000. The survey did not require companies to report whether low concentration products (at a concentration of less than 1% w/w) were manufactured or imported into Canada (Environment Canada 2001). Information on the use of 2,4,6-tri-tert-butylphenol that was received from the section 71 survey notice (Environment Canada 2001) indicates that all of this substance was reported for use in Canada as a fuel and oil/lubricant additive in the year 2000. However, it was confirmed that the only current use of this substance in Canada is as a fuel additive, and there is no use as a lubricant additive in Canada.
Information was voluntarily submitted for this substance as part of the Challenge for the calendar year 2006 (Environment Canada and Health Canada 2007). This information indicated that fewer than ten companies imported a combined total of between 1000 and 10 000kg of this substance into Canada in the year 2006, whether alone, in a product, in a mixture or in a manufactured item. In addition, fewer than ten companies reported using 2,4,6-tri-tert-butylphenol (whether alone, in a product, in a mixture or in a manufactured item) in a quantity below the prescribed threshold (that is, in a quantity less than 1000 kg at a concentration greater than 50%, or in a quantity less than 10 000 kg at any concentration). There were no reports voluntarily received on the manufacture of 2,4,6-tri-tert-butylphenol in Canada. Fewer than ten companies indicated stakeholder interest in this substance. Companies responding to the Challenge indicated that the substance is used as a fuel additive.
According to an Environment Canada study (Environment Canada 2008), there is no manufacture of 2,4,6-tri-tert–butylphenol in Canada nor is there any blending or re-packaging of the antioxidants containing 2,4,6-tri-tert–butylphenol. In 2006, fewer than 10 U.S. companies were identified as manufacturers/blenders of antioxidants containing 2,4,6-tri-tert-butylphenol. Some of these companies exported products containing 10 000 to 100 000kg of 2,4,6-tri-tert-butylphenol into Canada in 2006.
Based on the information received, the petroleum sector is the primary industrial sector involved with the substance (Environment Canada and Health Canada 2008b).
The substance 2,4,6-tri-tert-butylphenol is not reported to be naturally produced in the environment. In response to a section 71 notice (Environment Canada 2001), fewer than ten companies importing 2,4,6-tri-tert-butylphenol reported a release of the substance in the year 2000, corresponding to 20kg of the substance released to air (based on estimates of vapour losses). The section 71 survey did not gather release information from users of the substance and because of the use of the chemical as a fuel additive, it is possible that environmental releases (as reported in the survey) do not represent the total possible releases. None of the companies responding to the 2007 Challenge (Environment Canada 2007b) indicated releases of the substance to the environment.
When combusted with fuel, 99.6% of the substance in the fuel is assumed to be destroyed. This corresponds to 98% of the total amount of 2,4,6-tri-tert-butylphenol used in Canada.
Emissions of the substance to air could occur during transport and storage of the additives and fuel at refineries, bulk fuel facilities and service stations due to volatilization of liquids. A small portion of the substance would also be released to air as uncombusted tailpipe emissions. Total air emissions are estimated to account for <1% of all releases. Releases of the substance to industrial wastewater are estimated to account for <1% of the total amount of the substance in commerce. These estimated releases are due to capture, collection and disposal of potential spills or discharges associated with blending and handling activities at petroleum refineries.
The transport, storage and handling of gasoline and other fuels containing 2,4,6-tri-tert-butylphenol may also result in accidental release of this substance into the Canadian environment. This is believed to be the most likely potential source of release of this substance.
To estimate potential releases of the substance to the environment at different stages of its life cycle, a Mass Flow Tool was developed (Environment Canada 2007a). Empirical data concerning releases of specific substances to the environment are seldom available. Therefore, for each identified type of use of the substance, the proportion and quantity of release to the different environmental media are estimated, as is the proportion of the substance chemically transformed or sent for waste disposal.
Assumptions and input parameters used in making the release estimates are based on information obtained from a variety of sources, including responses to regulatory surveys, Statistics Canada, manufacturers’ websites and technical databases and documents. Of particular relevance are emission factors, which are generally expressed as the fraction of a substance released to the environment, particularly during its manufacture, processing, and use associated with industrial processes. Sources of such information include emission scenario documents, often developed under the auspices of the Organisation for Economic Co-operation and Development (OECD), and default assumptions used by different international chemical regulatory agencies. It is noted that the level of uncertainty in the mass of substance and quantity released to the environment generally increases toward the end of its life-cycle (Environment Canada and Health Canada 2008b).
When using this tool, the assumption is made that this substance behaves similarly to gasoline when used as a fuel additive. Based on the use of the substance only as a fuel additive, existing regulations and a worst-case scenario, it is assumed that loss by transformation during combustion is 99.6%. Losses to air are estimated to be <1% of the total amount in Canadian commerce. Based on environmental fate information in the assessment report, emissions to air are assumed to either rapidly oxidize in air or strongly partition to soil (Environment Canada and Health Canada 2008b). The remaining releases to wastewater are related to storage, handling and blending activities at petroleum refineries and account for <1% of the total substance in Canadian commerce.
The results of the Mass Flow Tool analysis and other collected information suggest that the most significant potential source of release of 2,4,6-tri-tert-butylphenol to the environment is associated with accidental releases of the fuels that contain the substance.
Currently, there are no risk management measures specifically related to 2,4,6-tri–tert–butylphenol in Canada. However, alkylphenol substances are required to be labeled as “Class 9 – Environmentally Hazardous Substances, Liquid,NOS (Not Otherwise Specified)” pursuant to the Transportation of Dangerous Goods Regulations.
When used as a fuel additive, potential environmental releases of 2,4,6-tri–tert–butylphenol as the substance, in an additive product and in the final fuel product are managed through many existing regulations, codes of practice, guidelines and best industry practices that are in place in Canada, both federally and provincially to prevent the release of fuel and its components in residential, commercial and industrial settings. These include, but are not limited to:
- Environmental Emergencies Regulations for gasoline(CEPA 1999)
- Onshore Pipeline Regulations (National Energy Board)
- Gasoline Dispensing Flow Rate Regulations(CEPA 1999)
- The Fisheries Act
- Storage tank requirements for fuel products (e.g. CCME Environmental Code of Practice for Underground and Above Ground Storage Tank Systems, Ontario Fire Code, Ontario Liquid Fuels Regulation (O.Reg. 217/01), New Brunswick “Petroleum Product Handling and Storage Regulation”, Alberta Fire Code)
- Transportation requirements for fuel products (e.g.Transportation of Dangerous Goods Act)
- Spill reporting and cleanup requirements for fuel products (e.g. Ontario Environmental Protection Act (s.92 and s.15), Alberta Environmental Protection and Enhancement Act)
- Effluent Monitoring (e.g. Ontario Effluent Monitoring and Effluent Limits – Petroleum Sector (O.Reg. 537/93)
- Contaminated site cleanup requirements (e.g. Ontario Environmental Protection Act)
- Handling and disposal of liquid and solid waste (e.g.Ontario Waste Management (Hazardous Waste) Regulation (O.Reg 347).
Importation, manufacture and use of substance 2,4,6-tri-tert-butylphenol is banned in Japan.
The substance 2,4,6-tri-tert-butylphenol has been identified as a high production volume (HPV) chemical under the United States Environmental Protection Agency’s HPV Challenge Program (US EPA 2007a,b) and is included on the OECD’s list of HPVchemicals (OECD2004). This substance is included on the Oslo-Paris (OSPAR) Commission’s list of chemicals for priority action (OSPAR 2007, ICES2007), but is considered a low production volume chemical (OSPAR 2006). Information provided by OSPAR Contracting Parties indicated possible uses at 33 tonnes in Denmark and 1 tonne in Norway (OSPAR 2006). The Swedish Product Register included 19 registrations of products containing 2,4,6-tri-tert-butylphenol, which corresponded to a use of 1 tonne in 2001 (OSPAR 2006).
Several substitutes for 2,4,6,-tri-tert-butylphenol are available. However, their technical and economic feasibility has yet to be confirmed.
It is important to note that most of the potential substitutes appear on later Challenge batches, or the medium priority list. As such, they will be assessed to determine whether they meet the section 64 criteria under CEPA 1999 under different timelines.
No information is available on alternative technologies and/or techniques.
Socio-economic factors have been considered in the development of the risk management objective and approach for 2,4,6-tri-tert-butylphenol. Socio-economic factors will also be considered in the development of regulations, instrument(s) and/or tool(s) as identified in the Cabinet Directive on Streamlining Regulation (Treasury Board of Canada Secretariat 2007) and the guidance provided in the Treasury Board documentAssessing, Selecting, and Implementing Instruments for Government Action.
2,4,6-tri-tert-butylphenol is a fuel additive used as an antioxidant in hydrocarbon fuels such as gasoline, jet fuel, diesel and biodiesel. As indicated in section 4, between 10,000 and 100,000 kg of 2,4,6-tri-tert-butylphenol was imported into Canada in 2006. While alternatives for 2,4,6-tri-tert-butylphenol are available, the cost of alternatives is thought to be two to three times more expensive.
2,4,6-tri-tert-butylphenol is imported into Canada for use primarily by the petroleum refining sector. 2,4,6-tri-tert-butylphenol is imported into Canada as part of the fuel additive package. There are less than 10 companies that reported to be using 2,4,6-tri-tert-butylphenol, purchased from U.S. manufacturers. Fuel additives containing 2,4,6-tri-tert-butylphenol, whether imported or manufactured in Canada, are added to fuels at petroleum refineries. As described in sections 5.1 and 5.2, the most significant potential source of release of this substance, and therefore the potential risk, is from accidental spills during transport, storage and handling of fuels containing 2,4,6-tri-tert-butylphenol.
The Government of Canada considered, where available, risk assessment information relevant to children’s exposure to this substance. As part of the Challenge, the Government asked industry and interested stakeholders to submit any information on the substance that may be used to inform risk assessment, risk management and product stewardship. In particular, stakeholders were asked through a questionnaire if any of the products containing the substance were intended for use by children. Given the information received, it is proposed that no risk management actions to specifically protect children are required for this substance at this time.
An environmental objective is a quantitative or qualitative statement of what should be achieved to address environmental or human health concerns identified during a risk assessment.
The ultimate environmental objective for 2,4,6-tri–tert–butylphenol is virtual elimination (VE) of releases to the environment as specified under subsections 65 and 77(4) of CEPA 1999.CEPA 1999 requires that substances targeted for VE be added to the Virtual Elimination List along with their Level of Quantification (LoQ). The LoQ is the lowest concentration that can be accurately measured using sensitive but routine sampling and analytical methods.
According to CEPA 1999, virtual elimination means, in respect of a toxic substance released into the environment as a result of human activity, the ultimate reduction of the quantity or concentration of the substance in the release below the LoQ specified in the Virtual Elimination List.
A risk management objective is a target expected to be achieved for a given substance by the implementation of risk management regulations, instrument(s) and/or tool(s).
The proposed risk management objective for 2,4,6-tri–tert–butylphenol is to prevent accidental releases of the substance to the environment.
In order to achieve the risk management objective and to work towards achieving the environmental objective, the current regulatory regime will be reviewed, including federal controls that contribute to preventing spills of 2,4,6-tri-tert–butylphenol as it is contained in fuels, the Fisheries Act that prohibits the release of deleterious substances in water frequented by fish and provincial/territorial controls to prevent accidental releases during storage and handling and to minimize any other accidental releases. Gaps to be filled will be identified and federal controls will be amended accordingly.
It is important to note that there are a number of fuel additives included in the Challenge under the Chemicals Management Plan. As these substances are found in different batches, they will be assessed and potentially managed under different timelines. As well, there are a number of fuels being addressed under the Chemicals Management Plan by the Petroleum Sector Stream Approach, which also has different timelines than the Challenge. As a result, 2,4,6-tri-tert-butylphenol will be considered as part of the Petroleum Sector Stream Approach with the objective to manage it in an efficient and integrated way with the other fuel additives and the fuels on the CMP.
The risk management scope for 2,4,6-tri–tert–butylphenol, which summarized the proposed risk management under consideration at that time, was published on May 17, 2008, and is available at www.ec.gc.ca/TOXICS/EN/detail.cfm?par_substanceID=
236&par_actn=s1. Industry and other interested stakeholders were invited to submit comments on the risk management scope during a 60-day comment period. Comments received on the risk management scope document were taken into consideration in the development of this proposed risk management approach document.
Consultation for the risk management approach will involve publication on January 31, 2009, and a 60-day public comment period.
The primary stakeholders include:
- users of 2,4,6-tri-tert-butylphenol
- handlers of 2,4,6-tri-tert-butylphenol
- non-governmental organizations
- provincial governments
- manufacturers and suppliers of fuel additives
- importers of fuel additives
| Actions | Date |
|---|---|
| Electronic consultation on proposed risk management approach | January 31, 2009 to April 1, 2009 |
| Response to comments on proposed risk management approach | At time of publication of proposed instrument |
| Consultation | To be determined |
Industry and other interested stakeholders are invited to submit comments on the content of this proposed risk management approach or to provide other information that would help to inform decision making. Please submit comments prior to April 1, 2009, since the Government of Canada will be moving forward with the risk management of 2,4,6-tri–tert–butylphenol after this date. Pursuant to section 313 of CEPA 1999, any person who provides information to the Minister underCEPA 1999 may submit with the information a request that it be treated as confidential. During the development of regulations, instrument(s) and/or tool(s), there will be opportunity for consultation. Comments and information submissions on the proposed risk management approach should be submitted to the address provided below:
Existing Substances Division
Gatineau QC K1A 0H3
Tel.: 1-888-228-0530 / 819-956-9313
Fax: 1-800-410-4314 / 819-953-4936
Email: Existing.Substances.Existantes@ec.gc.ca
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Footnotes
2National Chemical Inventories (NCI). 2006:AICS (Australian Inventory of Chemical Substances); ASIA-PAC (Asia-Pacific Substances Lists); ECL (Korean Existing Chemicals List); EINECS (European Inventory of Existing Commercial Chemical Substances);ENCS (Japanese Existing and New Chemical Substances); PICCS (Philippine Inventory of Chemicals and Chemical Substances);TSCA(Toxic Substances Control Act Chemical Substance Inventory); and DSL (Domestic Substances List).
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