[Federal Register Volume 59, Number 107 (Monday, June 6, 1994)]
[Unknown Section]
[Page 0]
From the Federal Register Online via the Government Publishing Office [www.gpo.gov]
[FR Doc No: 94-13677]
[[Page Unknown]]
[Federal Register: June 6, 1994]
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ENVIRONMENTAL PROTECTION AGENCY
40 CFR Part 372
[OPPTS-400085; FRL-4765-8]
Copper Monochlorophthalocyanine Pigment; Toxic Chemical Release
Reporting; Community Right-To-Know
AGENCY: Environmental Protection Agency (EPA).
ACTION: Proposed rule.
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SUMMARY: EPA is proposing to grant a petition to delete Color Index
(C.I.) Pigment Blue 15:1 from the ``copper compounds'' category of the
list of toxic chemicals subject to reporting under section 313 of the
Emergency Planning and Community Right-to-Know Act of 1986 (EPCRA).
C.I. Pigment Blue 15:1 is a mixture of C.I. Pigment Blue 15 (copper
phthalocyanine) and copper monochlorophthalocyanine. C.I. Pigment Blue
15 has already been deleted from the chemical category ``copper
compounds''; therefore, the Agency is treating this petition as a
request to remove copper monochlorophthalocyanine from the chemical
category ``copper compounds.'' This proposed rule is based on EPA's
belief that the copper ion from copper monochlorophthalocyanine will
not become available. In addition, EPA requests comment on the
alternative of exempting all copper phthalocyanine compounds that are
substituted with only hydrogen and/or bromine or chlorine from the
reporting requirements under the ``copper compounds'' category in EPCRA
section 313.
DATES: Written comments on this proposed rule should be received by EPA
on or before August 5, 1994.
ADDRESSES: Written comments should be submitted in triplicate to: OPPT
Docket Clerk, TSCA Document Receipt Office (7407), Office of Pollution
Prevention and Toxics, Environmental Protection Agency, Rm. NE-B607,
401 M St., SW., Washington, DC 20460. Comments should include the
document control number for this proposal, OPPTS-400085.
FOR FURTHER INFORMATION CONTACT: Maria J. Doa, Petitions Coordinator,
202-260-9592, for specific information on this proposed rule, or for
more information on EPCRA section 313, the Emergency Planning and
Community Right-to-Know Hotline, Environmental Protection Agency, Mail
Code 5101, 401 M St., SW., Washington, DC 20460, Toll free: 1-800-535-
0202, in Virginia and Alaska: 703-412-9877 or Toll free TDD: 1-800-553-
7672.
SUPPLEMENTARY INFORMATION:
I. Introduction
A. Statutory Authority
This proposed rule is issued under section 313(d) and (e)(1) of the
Emergency Planning and Community Right-to-Know Act of 1986 (EPCRA), 42
U.S.C. 11023. EPCRA is also referred to as Title III of the Superfund
Amendments and Reauthorization Act of 1986 (SARA) (Pub. L. 99-499).
B. Background
Section 313 of EPCRA requires certain facilities manufacturing,
processing, or otherwise using listed toxic chemicals to report their
environmental releases of such chemicals annually. Beginning with the
1991 reporting year, such facilities must also report pollution
prevention and recycling data for such chemicals, pursuant to section
6607 of the Pollution Prevention Act (42 U.S.C. 13106). When enacted,
section 313 established an initial list of toxic chemicals that was
comprised of more than 300 chemicals and 20 chemical categories.
Section 313(d) authorizes EPA to add chemicals to or delete chemicals
from the list, and sets forth criteria for these actions. Under section
313(e)(1), any person may petition EPA to add chemicals to or delete
chemicals from the list. EPA has added and deleted chemicals from the
original statutory list.
EPA issued a statement of petition policy and guidance in the
Federal Register of February 4, 1987 (52 FR 3479), to provide guidance
regarding the recommended content and format for petitions. On May 23,
1991 (56 FR 23703), EPA issued a statement of policy and guidance
regarding the recommended content of petitions to delete individual
members of the section 313 metal compound categories. Pursuant to EPCRA
section 313(e)(1), EPA must respond to petitions within 180 days either
by initiating a rulemaking or by publishing an explanation of why the
petition has been denied.
II. Description of Petition
On March 5, 1993, the Agency received a petition from the Color
Pigments Manufacturers Association (CPMA) to delete Color Index (C.I.)
Pigment Blue 15:1 from the chemical category ``copper compounds''
subject to EPCRA reporting requirements. C.I. Pigment Blue 15:1 is a
mixture of C.I. Pigment Blue 15 (copper phthalocyanine) and copper
monochlorophthalocyanine. C.I. Pigment Blue 15 has already been deleted
from the chemical category ``copper compounds'' (56 FR 23650);
therefore, the Agency is treating this petition as a request to remove
copper monochlorophthalocyanine from the chemical category ``copper
compounds.''
The copper monochlorophthalocyanine pigment, which is the subject
of this petition, exists as two isomers. One isomer is substituted with
a single chlorine atom at the 1-position. The second isomer is
substituted with a single chlorine atom at the 2-position. The copper
monochlorophthalocyanine pigment is described by three CAS numbers. CAS
number 15975-60-7 describes the copper 1-chlorophthalocyanine pigment.
CAS number 147-13-7 describes the copper 2-chlorophthalocyanine
pigment. CAS number 12239-87-1 describes the copper
monochlorophthalocyanine pigment with the position of a single chlorine
atom unspecified. EPA is proposing to delete both isomers and hence all
three CAS numbers from the copper compounds category.
In the statement of policy and guidance on the metal compound
categories of section 313 of EPCRA (56 FR 23703, May 23, 1991), EPA
articulated the view that the toxicity of a metal-containing compound
that dissociates or reacts to generate the metal ion can be expressed
as a function of the toxicity induced by the intact species and the
availability of the metal ion. Therefore, the degree of dissociation,
bioaccumulation, and the level at which toxicity is induced by the
metal ion will be considered in making any delisting decision under
EPCRA section 313. Thus, for petitions to exempt individual metal-
containing compounds from the reporting requirements under EPCRA
section 313, EPA has decided to base its decisions on the evaluation of
all chemical and biological processes that may lead to metal ion
availability as well as on the toxicity of the intact species. These
decisions will continue to be based on information provided by the
petitioner, Agency documents, and available literature. EPCRA section
313(d)(3) requires EPA to determine that none of the criteria in EPCRA
section 313(d)(2) are met before a chemical may be deleted from the
EPCRA section 313 list. Under the policy for metal compound categories,
this means that the effects induced by both a metal ion and the intact
species described by the metal compound category must be considered in
light of the EPCRA section 313(d)(2) criteria. The effects induced by
each metal ion described by the metal compound categories meet the
criteria under EPCRA section 313(d)(2). To delete a metal compound from
the EPCRA section 313 list, EPA must conclude that the metal ion will
not become available at a level that can be expected to induce toxicity
of a type described in EPCRA section 313(d)(2), and that the intact
species does not meet the criteria of EPCRA section 313(d)(2).
Accordingly, EPA will generally deny petitions to delete chemicals if:
(1) The intact species meets the EPCRA section 313(d)(2) criteria, (2)
the chemical will dissociate or react to generate the metal ion at
levels which can reasonably be anticipated to cause adverse effects as
described in EPCRA section 313(d)(2), or (3) EPA does not possess and
the petitioners failed to provide information to properly characterize
the metal ion availability.
III. Technical Review
The Agency has previously addressed the transformation processes
that may generate copper ion from copper phthalocyanine compounds in
its review of a petition to delete three copper phthalocyanine pigments
(Pigment Blue 15, copper phthalocyanine; Pigment Green 7, copper
poly(14)chlorophthalocyanine; and Pigment Green 36, copper
hexabromodecachlorophthalocyanine) from EPCRA section 313 reporting
requirements. These three copper phthalocyanine pigments were deleted
from EPCRA section 313 on May 23, 1991 (56 FR 23650), because copper
ion could not reasonably be expected to become available from these
pigments and because there was no indication from the available data
that the intact pigments could reasonably be anticipated to cause
acute, chronic, or environmental toxicity. No data on the specific
copper monochlorophthalocyanine compounds which are the subject of this
petition were found. However, in its analysis of the three previously
deleted compounds, the Agency used data on both brominated/chlorinated
copper phthalocyanine and copper phthalocyanine. This information was
selected because Pigment Blue 15, Pigment Green 7, and Pigment Green 36
ranged in degree of bromination/chlorination from zero (Pigment Blue
15) to 100 percent (Pigment Green 36). The transformation potential of
many organic compounds is dependent, in part, on the number of bromine
or chlorine atoms present in the molecule. Although there are
exceptions, generally, the more highly brominated or chlorinated an
organic compound is, the less likely it is to undergo biotic or abiotic
transformations. Once the transformation potential for copper
phthalocyanine pigments at the extremes of the range of possible
bromination/chlorination had been assessed, the transformation
potential for those copper phthalocyanine pigments with bromination/
chlorination greater than zero and less than 100 percent, including
copper monochlorophthalocyanine, could be inferred. The transformation
processes reviewed included, hydrolysis, photolysis, abiotic and biotic
aerobic degradation, abiotic and biotic anaerobic degradation,
bioavailability of the ion when the compounds are ingested or inhaled,
and bioaccumulation. The following discussion summarizes the
information reviewed.
1. Copper ion (Refs. 2 and 7). Copper is recognized as an essential
element. It is essential to a number of normal physiological processes
including erythropoiesis, connective tissue metabolism, bone
development, and nervous system function. The National Academy of
Sciences' recommended daily allowance (RDA) for adults is 2.0 to 3.0
milligrams (mg) copper/day. Copper is also used as a hematinic (to
stimulate red blood cell production) in adults at a dose of 3.8 to 7.6
mg/day.
a. Human health effects. Copper poisoning has been demonstrated in
animals and identified in humans. The liver is the main storage depot
for copper, and hepatic damage is associated with the accumulation of
high levels of copper. Hepatic toxicity is characterized by
hepatocellular necrosis, regenerative activity, and cirrhosis. Kidney
necrosis and elevated levels of serum copper occur only after the liver
begins to accumulate high levels of copper. These elevated serum copper
levels can progress to sudden hemolytic anemia and jaundice.
The types of neurological effects associated with copper poisoning
can include demyelination and cerebral degeneration. These effects are
thought to be related to defects in catecholamine metabolism.
Alterations in brain neurotransmitter systems have been observed in
rats following intraperitoneal injections of 2 milligrams/kilogram/day
(mg/kg/day) for 21 days. There are two groups that are at a
particularly increased risk from copper exposure. These include
individuals with Wilson's disease, which is an inborn error in copper
metabolism. The metabolic error in Wilson's disease allows copper to
accumulate in the liver, brain, kidney, and cornea, causing hemolytic
anemia, neurological abnormalities, and corneal opacity. In addition,
individuals with glucose-6-phosphate dehydrogenase deficiencies may
also be at greater risk of experiencing toxic effects from copper
exposure.
Copper is classified in EPA's Group D (insufficient data) for
carcinogenic potential. Copper is generally negative in mutagenicity
bioassays. Oral bioassays using copper were negative; subcutaneous
injection of copper compounds has been reported to induce tumor
formation in one sex and strain of mice.
The maximum contaminant level (MCL) established for copper under
the Safe Drinking Water Act is 1.3 milligrams/liter (mg/L) (3.6 mg/
day).
b. Ecological effects. Copper is very toxic to aquatic life. It is
sometimes used as a biocide to control undesirable aquatic plants. EPA
has issued Water Quality Criteria for copper to protect aquatic life.
The acute criterion in fresh water at a hardness of 50 mg/L is 9.2
micrograms/liter (ug/L). The chronic criterion in fresh water is 6.5
ug/L at a hardness of 50 mg/L. In salt water at a hardness of 50 mg/L,
the acute criterion is 2.9 ug/L. At a hardness of 100 mg/L, the
freshwater acute criterion is 18 ug/L, the freshwater chronic criterion
is 12 ug/L, and the salt water acute criterion is 2.9 ug/L.
2. Availability of copper ion. The copper monochlorophthalocyanine
pigments are expected to be extremely stable to chemically and
biologically induced transformations.
a. Thermal stability. Based on their structural analogy to other
copper phthalocyanine pigments, copper monochlorophthalocyanine
pigments are expected to be extremely stable thermally. Copper
phthalocyanine pigments only begin to show signs of decomposition at
temperatures above 500 deg.C (Ref. 6).
b. Hydrolysis. Copper phthalocyanine pigments have very low
solubilities in water and are not expected to dissociate or hydrolyze
in water under environmental conditions. Hydrolysis of copper
phthalocyanine pigments does not occur in basic and nonoxidizing acidic
media (Ref. 3). By structural analogy to copper phthalocyanine pigments
for which data are available, hydrolysis of the copper
monochlorophthalocyanine pigments is not expected to be a significant
environmental transformation process.
c. Photolysis. Based on studies carried out to determine the light
fastness of structurally similar copper phthalocyanine pigments, it
appears that photolysis of copper monochlorophthalocyanine pigments
with resultant release of copper ion will not occur (Ref. 4).
d. Abiotic oxidation. Data indicate that under ambient
environmental conditions, abiotic oxidation of copper phthalocyanine
pigments does not occur. More rigorous conditions are required to
effect the oxidation of copper phthalocyanine pigments and subsequent
release of copper ion. These pigments can be chemically oxidized to
yield phthalimides and copper nitrate by boiling in dilute nitric acid
(Ref. 3). Oxidation of the pigments can also occur by treatment with
ceric sulfate in dilute sulfuric acid at 25 deg.C, or by reaction with
potassium permanganate (Ref. 1). Because rigorous conditions are
required to oxidize copper phthalocyanine pigments, abiotic oxidation
of copper monochlorophthalocyanine pigments under ambient environmental
conditions is not likely to occur.
e. Microbial transformations. No data on the anaerobic or aerobic
biodegradability of the copper monochlorophthalocyanine pigments were
found. However, based on their extremely low solubility in water, their
large cross-sectional diameter, and, with the exception of the
chlorine, the lack of substituent groups associated with facile primary
degradation, copper monochlorophthalocyanine pigments are expected to
be very resistant to degradation processes (Ref. 5).
f. Bioavailability. On the basis of molecular weight, extremely low
solubility in water, and data from subchronic toxicity tests on other
copper phthalocyanine pigments (Ref. 7), copper
monochlorophthalocyanine is not expected to be appreciably absorbed by
any route of exposure or metabolized to yield copper ion.
g. Bioaccumulation. Because copper ion does not appear to be
available from the copper phthalocyanine pigments, bioaccumulation of
copper ion is not a concern for copper monochlorophthalocyanine
pigments.
h. Summary. By virtue of their structural analogy to other copper
phthalocyanine pigments, EPA believes that the availability of copper
ion from the copper monochlorophthalocyanine pigments by hydrolysis,
photolysis, and aerobic and anaerobic transformations is negligible.
Copper ion is not expected to be bioavailable from the copper
monochlorophthalocyanine pigments. The copper monochlorophthalocyanine
pigments are not expected to be appreciably absorbed by any route of
exposure or metabolized to yield the copper ion.
3. Manufacturing, use, and release. Phthalocyanine blue pigments,
such as copper monochlorophthalocyanine, are generally manufactured
using one of two methods. Copper monochlorophthalocyanine is
manufactured by a phthalonitrile baking process or a solvent process.
The phthalonitrile baking process yields a range of 70 to 85 percent of
product. The solvent process is more popular and yields a purer form
with a yield of 85 to 95 percent of product. Following the synthesis
the crude product is isolated. Finishing of the crude pigment can
involve any of a number of processes such as dissolution in acid
followed by controlled precipitation, intensive milling with urea and
sulfuric acid, milling with sodium chloride, or milling with sodium
chloride and solvent.
Copper monochlorophthlocyanine is often used in combination with
other colorants. The primary uses of copper monochlorophthalocyanine
mixtures are as colorants for coatings, paints, printing inks, and
plastics.
The EPCRA section 313 reported releases of copper from three
facilities which were identified as manufacturers of copper
monochlorophthalocyanine were 2,354 pounds in 1990 and 491 pounds for
1991. Facilities that process or use copper monochlorophthalocyanine
pigment could not be identified and therefore releases from these
facilities could not be estimated.
IV. Explanation for Proposed Action To Delete Copper
Monochlorophthalocyanine
EPA is granting the petition and proposing to delete copper
monochlorophthalocyanine from the copper compounds category of the
EPCRA section 313 list of toxic chemicals. As stated in Unit II. of
this preamble, petitions for delisting a member of a metal compound
category will be denied unless EPA can conclude that the intact species
does not meet the criteria of section 313(d)(2) and the metal ion will
not be available at a level that can reasonably be anticipated to
induce toxicity. This decision to propose to delist copper
monochlorophthalocyanine is based on EPA's belief that: (1) The intact
species does not meet the EPCRA section 313(d) criteria and (2) the
copper ion from copper monochlorophthalocyanine will not become
available.
After reviewing the petition and available information, EPA has
concluded that copper monochlorophthalocyanine is not known to cause or
cannot reasonably be anticipated to cause acute or chronic toxicity in
humans or adverse effects in the environment, and thus does not meet
the criteria of EPCRA section 313(d)(2).
V. Request for Public Comment
EPA requests public comment on this proposed rule to delete copper
monochlorophthalocyanine from the category ``copper compounds'' on the
EPCRA section 313 list of toxic chemicals. In addition, EPA requests
comment on the alternative of exempting all copper phthalocyanine
compounds that are substituted with only hydrogen and/or bromine or
chlorine from the reporting requirements under the ``copper compounds''
category on the EPCRA section 313 list. As stated in Unit III. of this
preamble, EPA has previously reviewed brominated/chlorinated copper
phthalocyanine compounds as well as the parent compound, copper
phthalocyanine, and believes that its conclusions regarding the
availability of soluble copper from these compounds apply to all copper
phthalocyanine compounds that are substituted with only hydrogen and/or
bromine or chlorine. Comments should be submitted to the address listed
under the ADDRESSES unit. All comments must be received by EPA on or
before August 5, 1994.
VI. Rulemaking Record
The record supporting this proposed rule is contained in docket
number OPPTS-400085. All documents, including an index of the docket,
are available in the TSCA Nonconfidential Information Center (NCIC),
also known as, TSCA Public Docket Office from noon to 4 p.m., Monday
through Friday, excluding legal holidays. TSCA NCIC is located at EPA
Headquarters, Rm. NE-B607, 401 M St., SW., Washington, DC 20460.
VII. References
(1) Dent, C.E., Linstead, R.P., and Lowe, A.R., Journal of the
Chemical Society 1033-1039 (1934).
(2) IRIS. 1992. Integrated Risk Information System. U.S.
Environmental Protection Agency, Washington, DC.
(3) Lever, A.B.P. ``The Phthalocyanines.'' In: Handbook of Pigments
J. Wiley and Sons, New York, NY (1975):27-114.
(4) USEPA, OPTS, EED. Memorandum from D. Lynch to J. Rovinski, ETD
entitled ``Exposure Report for Copper Phthalocyanine Petition,'' dated
October 7, 1988.
(5) USEPA, OPTS, EED. Memorandum from D. Lynch to M. Doa, ETD
entitled ``Anaerobic Biodegradation of Copper Phthalocyanine
Pigments,'' dated October 5, 1990.
(6) USEPA, OPTS, ETD. Memorandum from R. Raksphal to K. Moss, ETD
entitled ``Section 313(e) Petition on Three Phthalocyanine Pigments,''
dated June 28, 1988.
(7) USEPA, OPTS, HERD. Memorandum and attachments from L. Randecker
to R. Kent, HERD entitled ``Petition to Delist Three Copper
Phthalocyanine Pigments,'' dated October 3, 1988.
(8) USEPA, OPPT, EETD. Darling, D., ``Chemistry Report for the
Proposed Deletion of Monochlorophthalocyanine Blue (C.I. Pigment 15:2)
from the EPCRA Section 313 List of Toxic Chemicals,'' dated February 9,
1994.
(9) USEPA, OPPT, EETD. ``Economic Analysis of the Proposed Deletion
of Monochlorophthalocyanine Blue from the EPCRA Section 313 List of
Toxic Chemicals,'' dated January 19, 1994.
(10) USEPA, OPPT, EETD. Memorandum from J. Jon to D. Lynch, EETD
entitled ``Engineering Report for Monochlorophtalocyanine Blue,'' dated
February 2, 1994.
VIII. Regulatory Assessment Requirements
A. Executive Order 12866
Under Executive Order 12866 (58 FR 51735, October 4, 1993), the
Agency must determine whether the regulatory action is ``significant''
and therefore subject to review by the Office of Management and Budget
(OMB) and the requirements of the Executive Order. Section 3(f) of the
Order defines a ``significant regulatory action'' as an action likely
to lead to a rule (1) Having an annual effect on the economy of $100
million or more, or adversely and materially affecting a sector of the
economy, productivity, competition, jobs, the environment, public
health or safety, or State, local, or tribal governments or communities
(also referred to as ``economically significant''); (2) creating
serious inconsistency or otherwise interfering with an action taken or
planned by another agency; (3) materially altering the budgetary
impacts of entitlements, grants, user fees, or loan programs; or (4)
raising novel legal or policy issues arising out of legal mandates, the
President's priorities, or the principles set forth in this Executive
Order.
Pursuant to the terms of this Executive Order, it has been
determined that this proposed rule is not ``significant'' and therefore
not subject to OMB review.
B. Regulatory Flexibility Act
Under the Regulatory Flexibility Act of 1980, the Agency must
conduct a small business analysis to determine whether a substantial
number of small entities would be significantly affected by the
proposed rule. Because the proposed rule eliminates an existing
requirement, it would result in cost savings to facilities, including
small entities.
C. Paperwork Reduction Act
This proposed rule does not have any information collection
requirements subject to the provisions of the Paperwork Reduction Act
of 1980, 44 U.S.C. 3501 et seq.
List of Subjects in 40 CFR Part 372
Environmental protection, Chemicals, Community right-to-know,
Reporting and recordkeeping requirements, and Toxic chemicals.
Dated: May 23, 1994.
Lynn R. Goldman,
Assistant Administrator, Office of Prevention, Pesticides and Toxic
Substances.
Therefore, it is proposed that 40 CFR part 372 be amended as
follows:
1. The authority citation for part 372 would continue to read as
follows:
Authority: 42 U.S.C. 11023 and 11048.
Sec. 372.65 [Amended]
2. In Sec. 372.65(c) by adding the following language to the copper
compounds listing ``(except copper monochlorophthalocyanine known by
the following CAS numbers 15975-60-7, 147-13-7, and 12239-87-1).''
[FR Doc. 94-13677 Filed 6-3-94; 8:45 am]
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