[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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