[Federal Register Volume 59, Number 14 (Friday, January 21, 1994)]
[Unknown Section]
[Page 0]
From the Federal Register Online via the Government Publishing Office [www.gpo.gov]
[FR Doc No: 94-1423]
[[Page Unknown]]
[Federal Register: January 21, 1994]
VOL. 59, NO. 14
Friday, January 21, 1994
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DEPARTMENT OF HEALTH AND HUMAN SERVICES
Food and Drug Administration
21 CFR Parts 176 and 178
[Docket No. 93N-0420]
Indirect Food Additives: Paper and Paperboard Components;
Adjuvants, Production Aids, and Sanitizers; Technical Amendment
AGENCY: Food and Drug Administration, HHS.
ACTION: Proposed rule.
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SUMMARY: The Food and Drug Administration (FDA) is proposing to amend
its regulations to correct an error in nomenclature. The amendment
would add alkyl mono- and disulfonic acids, sodium salts (produced from
n-alkanes in the range C10-C18 with not less than 50 percent
C14-C16) as a component of paper and paperboard in contact
with food, as an antistatic agent, and as an emulsifier and/or surface
active agent. Additionally, because certain sections contain multiple
entries for the additive, the agency is proposing to amend its
regulations so that all uses of the additive are combined under single
entries within those sections.
DATES: Submit written comments by March 22, 1994.
ADDRESSES: Written comments to the Dockets Management Branch (HFA-305),
Food and Drug Administration, rm. 1-23, 12420 Parklawn Dr., Rockville,
MD 20857.
FOR FURTHER INFORMATION CONTACT: Andrew Zajac, Center for Food Safety
and Applied Nutrition (HFS-216), Food and Drug Administration, 200 C
St. SW., Washington, DC 20204, 202-254-9500.
SUPPLEMENTARY INFORMATION: In the Federal Register of May 8, 1963 (28
FR 4615), FDA published a final rule in response to a food additive
petition (FAP 1B0492), listing petroleum sulfonates in Sec. 121.2571
Components of paper and paperboard in contact with dry food (21 CFR
121.2571) (currently Sec. 176.180 (21 CFR 176.180)). In response to the
same petition, the agency issued a notice of proposed rulemaking in the
Federal Register of June 16, 1964 (29 FR 7687), which proposed to amend
Sec. 121.2526 Components of paper and paperboard in contact with
aqueous and fatty foods (21 CFR 121.2526) (currently Sec. 176.170 (21
CFR 176.170)) to provide for the use of petroleum sulfonates produced
by sulfonating straight-chain aliphatic hydrocarbons of the C12-
C18 range. On the basis of comments received, the agency published
an amendment to the regulations in the Federal Register of February 25,
1965 (30 FR 2430), and omitted the above proposed rule pending
clarification of the chemical identity. The agency subsequently issued
a regulation in the Federal Register of July 2, 1966 (31 FR 9106),
providing for the use of n-alkylsulfonates (alkyl groups are even
numbered in the range C12-C18 and are not less than 50
percent C14 and C16) as components of paper and paperboard in
contact with aqueous and fatty foods (Sec. 176.170) for use as
emulsifiers for vinylidene chloride copolymer coatings at levels not to
exceed 2 percent by weight of the coating solids. The petitioner
subsequently submitted comments advising that they had incorrectly
identified the additive as containing only even-numbered alkyl groups
in the range C12 through C18 with not less than 50 percent
C14 and C16, whereas further study showed that the substance
deemed safe as a result of feeding studies contains all of the odd- and
even-numbered alkyl groups in the range C10-C18 with not less
than 50 percent C14 through C16. Therefore, the agency issued
a regulation in the Federal Register of March 2, 1967 (32 FR 3442), and
corrected the error of the listing of the substance to read as follows:
n-alkylsulfonate (alkyl group is in the range C10-C18 with
not less than 50 percent C14-C16).
In response to a food additive petition (FAP 9B2376), FDA published
a regulation in the Federal Register of July 17, 1970 (35 FR 11469),
listing n-alkylsulfonate (alkyl group is in the range C10 through
C18 with not less than 50 percent C14-C16) in
Sec. 121.2541 Emulsifiers and/or surface-active agents (21 CFR
121.2541) (currently Sec. 178.3400 (21 CFR 178.3400)) for use at levels
not to exceed 2 percent by weight of polyvinyl chloride and/or vinyl
chloride copolymers complying with Sec. 121.2521 (21 CFR 121.2521)
(currently Sec. 177.1980 (21 CFR 177. 1980)).
In response to a food additive petition (FAP 7B3274), FDA published
a regulation in the Federal Register on July 20, 1979 (44 FR 42678),
providing for the additional use of n-alkylsulfonate (alkyl group is in
the range C10-C18 with not less than 50 percent C14-
C16) by amending Secs. 176.170 and 178.3400 to include the use of
the substance as an emulsifier in vinylidene chloride copolymer or
homopolymer coatings at levels not to exceed a total of 2.6 percent by
weight of coating solids. The finished polymer contacts food only of
the Types I, II, III, IV, V, VIA, VIB, VII, VIII, and IX as identified
in Table 1 of Sec. 176.170(c) and limited to conditions of use E, F,
and G described in Table 2 of Sec. 176.170.
In response to a food additive petition (FAP 9B3476), FDA published
a final rule in the Federal Register on December 30, 1980 (45 FR
85726), listing sodium n-alkylsulfonate (alkyl group in the range of
C10-C18 with not less than 50 percent C14-C16) in
Sec. 178.3130 Antistatic and/or antifogging agents in food-packaging
materials (21 CFR 178.3130) for use only as an antistatic agent at
levels not to exceed 0.1 percent by weight of polyolefin films that
comply with Sec. 177.1520 (21 CFR 177.1520): provided, that the
finished olefin polymers contact foods only of Types I, II, III, IV, V,
VIA, VIB, VII, VIII, and IX described in Table 1 of Sec. 176.170(c),
and under conditions of use E, F, and G described in Table 2 of
Sec. 176.170(c).
Lastly, in a final rule published in the Federal Register on August
21, 1991 (56 FR 41456), in response to FAP 8B4097, FDA issued a
regulation listing sodium sec-alkyl mono- and disulfonates (alkyl group
in the range of C10-C18 with not less than 50 percent
C14-C16 in Sec. 178.3130 (21 CFR 178.3130) for use as
antistatic agents at levels not to exceed 3.0 percent by weight of
polystyrene or rubber-modified polystyrene complying with
Sec. 177.1640(c) (21 CFR 177.1640) under conditions of use B through H
described in Table 2 of Sec. 176.170(c) and in Sec. 178.3400 for use as
emulsifiers and/or surface-active agents at levels not to exceed 3.0
percent by weight of polystyrene or rubber-modified polystyrene
complying with Sec. 177.1640(c) (21 CFR 177.1640(c)) under conditions
of use B through H described in Table 2 of Sec. 176.170(c).
These previously regulated petitions were reviewed by FDA, and the
agency determined that:
(1) The substance, n-alkylsulfonate, which is the subject of FAP's
1B0492 and 9B2376, is manufactured by sulfochlorination of straight-
chain (normal) aliphatic hydrocarbons of the C12 to C18
range. The resultant alkylsulfonate contains alkyl groups of C10-
C18 in length with greater than 50 percent C14-C16. In
FAP 7B3274, the petitioner stated that n-alkylsulfonate, also called
sodium alkylsulfonate, was manufactured by sulfochlorination of a
``base paraffin,'' followed by treatment with sodium hydroxide to
saponify the alkyl sulfochlorides to their respective sodium salts.
Information on the distribution of the alkyl groups in the final
product was provided, and was found to conform with the distributions
set forth in FAP's 1B0492 and 9B2376. The petitioner also provided a
structural formula of the substance, depicting it as a straight-chain
alkylsulfonate.
(2) Sodium n-alkylsulfonate, which is the subject of FAP 9B3476,
was stated to conform with the composition of the substance described
in FAP's 7B3274 and 9B2376. Additionally, the petitioner provided a
specification of approximately 8.5 percent di- and polysulfonate
content for their product; none of the previous petitions proposed such
a specification.
(3) Finally, FAP 8B4097 describes sodium sec-alkyl mono- and
disulfonates as being manufactured by sulfoxidation of normal
(unbranched) alkanes followed by saponification. The petitioner stated
that this substance is the same substance that is the subject of FAP
9B3476, and is identical to the substances referred to as ``n-
alkylsulfonates'' in the aforementioned petitions. The petitioner
stated that the resultant sodium sec-alkyl sulfonate is a mixture of
approximately 87 percent monosulfonate and 13 percent disulfonate
forms.
FDA believes that the substances that are the subject of FAP's
1B0492, 9B2376, 7B3274, 9B3476, and 8B4097 are one and the same.
``Sodium alkylsulfonate'' was prepared either by the sulfochlorination
or sulfoxidation of straight-chain (normal) alkanes, followed by
saponification with sodium hydroxide to yield the sodium salt. The
sulfochlorination and sulfoxidation reactions occur by similar
mechanisms which involve the reaction of an alkyl radical with sulfur
dioxide. Both of these reactions result in random sulfonylation and in
significant levels of di- and poly- sulfonylation of the alkane.
However, based upon the molecular mechanism involved in either process,
namely free-radical substitution, it would be expected that secondary
carbons of normal alkanes would be sulfonylated in preference to
primary (terminal) carbons. Therefore, the agency concludes that
``sodium alkylsulfonates'' are prepared exclusively by the reaction of
normal alkanes that are sulfonylated by free-radical substitution, and
that the expected product from using either sulfochlorination or
sulfoxidation is sodium sec-alkyl mono- and disulfonates. Minor amounts
of product that is mono- or disulfonylated at the terminal carbons of
the alkyl moieties are also formed.
FDA believes that the names ``n-alkylsulfonate'' and ``sodium n-
alkylsulfonate'' are inappropriate, because this nomenclature implies
derivatization only on terminal or primary carbons of the n-alkyl
chain. The ``n-alkyl'' term appears to have arisen from the normal
alkanes used in the manufacture of the final product, rather than from
the structure of the alkyl moiety in the sulfonated product itself.
Furthermore, ``n-alkylsulfonate'' does not specify the sodium salt.
Additionally, neither ``n-alkylsulfonate'' and ``sodium n-alkyl
sulfonate'' indicate the additive is a mixture of mono- and disulfonate
sodium salts. The name ``sodium sec-alkyl mono- and disulfonates'' is
too limiting in that it only includes sodium sec-alkyl mono- and
disulfonates and excludes the minor products sodium n-alkyl mono- and
disulfonates. The agency concludes that the name ``alkyl mono- and
disulfonic acids, sodium salts (produced from n-alkanes in the range
C10-C18 with not less than 50 percent C14-C16)''
would best identify the substance that is the subject of these
petitions.
The nomenclature ``alkyl mono- and disulfonic acids, sodium salts
(produced from n-alkanes in the range C10-C18 with not less
than 50 percent C14-C16)'' adequately addresses: (1) The
structure of the alkyl moiety, in that sulfonylation of n-alkanes will
result only in sec-alkylsulfonates (substitution at an internal carbon,
the principal product) or linear alkylsulfonates (substitution at
terminal carbons, the minor product); (2) the sodium salt form; and (3)
the degree of sulfonylation. FDA consequently is proposing to replace
the existing nomenclature in Secs. 176.170, 176.180, 178.3130, and
178.3400 with the nomenclature ``alkyl mono- and disulfonic acids,
sodium salts (produced from n-alkanes in the range C10-C18
with not less than 50 percent C14-C16)''.
With regard to an appropriate Chemical Abstracts Service Registry
Number (CAS Reg. No.) for the subject substance, CAS Reg. No. 68037-49-
0 (sulfonic acids, C10-C18 alkane, sodium salts) is the only
one currently available. This term is too general, as it does not
specify ``n-alkyl groups in the range C10-C18 with not less
than 50 percent C14-C16'' nor ``mono- and disulfonic acids''.
Therefore, an appropriate CAS Reg. No. for this additive does not
currently exist.
The agency has determined under 21 CFR 25.24(a)(9) that this action
is of a type that does not individually or cumulatively have a
significant effect on the human environment. Therefore, neither an
environmental assessment nor an environmental impact statement is
required.
In accordance with the Regulatory Flexibility Act, FDA has
considered the effect that this proposal would have on small entities
including small businesses and has determined that the substitution of
the correct name for the regulated additive will have no effect on
small entities. Therefore, FDA certifies that the publication of this
proposal will not have a significant economic impact on a substantial
number of small entities.
Interested persons may, on or before March 22, 1994, submit to the
Dockets Management Branch (address above) written comments regarding
this proposal. Two copies of any comments are to be submitted, except
that individuals may submit one copy. Comments are to be identified
with the docket number found in brackets in the heading of this
document. Received comments may be seen in the office above between 9
a.m. and 4 p.m., Monday through Friday.
List of Subjects in 21 CFR Parts 176 and 178
Food additives, Food packaging.
Therefore, under the Federal Food, Drug, and Cosmetic Act and under
authority delegated to the Commissioner of Food and Drugs and
redelegated to the Director, Center for Food Safety and Applied
Nutrition, it is proposed that 21 CFR parts 176 and 178 be amended as
follows:
PART 176--INDIRECT FOOD ADDITIVES: PAPER AND PAPERBOARD COMPONENTS
1. The authority citation for 21 CFR part 176 continues to read as
follows:
Authority: Secs. 201, 402, 406, 409, 721 of the Federal Food,
Drug, and Cosmetic Act (21 U.S.C. 321, 342, 346, 348, 379e).
2. Section 176.170 is amended in the table in paragraph (b)(2) by
removing the entry for ``n-Alkylsulfonate (alkyl group is in the range
C10-C18 with not less than 50 percent C14-C16)''
and by alphabetically adding a new entry under the headings ``List of
substances'' and ``Limitations'' to read as follows:
Sec. 176.170 Components of paper and paperboard in contact with
aqueous and fatty foods.
* * * * *
(b) * * *
(2) * * *
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List of substances Limitations
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Alkyl mono- and disulfonic acids, For use only:
sodium salts (produced from n-
alkanes in the range of C10-C18
with not less than 50 percent C14-
C16).
1. As emulsifiers for vinylidene
chloride copolymer coatings and
limited to use at levels not to
exceed 2 percent by weight of the
coating solids.
2. As emulsifiers for vinylidene
chloride copolymer or homopolymer
coatings at levels not to exceed a
total of 2.6 percent by weight of
coating solids. The finished
polymer contacts food only of
types identified in paragraph (c)
of this section, Table 1, under
Types I, II, III, IV, V, VIA, VIB,
VII, VIII, and IX and under
conditions of use E, F, and G
described in Table 2 of paragraph
(c) of this section.
*******
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* * * * *
3. Section 176.180 is amended in the table in paragraph (b)(2) by
removing the entry for ``Petroleum sulfonates'' and by alphabetically
adding a new entry under the heading ``List of substances'' to read as
follows:
Sec. 176.180 Components of paper and paperboard in contact with dry
food.
* * * * *
(b) * * *
(2) * * *
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List of substances Limitations
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Alkyl mono- and disulfonic acids,
sodium salts (produced from n-
alkanes in the range of C10-C18
with not less than 50 percent C14-
C16).
*******
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PART 178--INDIRECT FOOD ADDITIVES: ADJUVANTS, PRODUCTION AIDS, AND
SANITIZERS
4. The authority citation for 21 CFR part 178 continues to read as
follows:
Authority: Secs. 201, 402, 409, 721 of the Federal Food, Drug,
and Cosmetic Act (21 U.S.C. 321, 342, 348, 379e).
5. Section 178.3130 is amended in the table in paragraph (b) by
removing the entries for ``Sodium n-alkylsulfonate (alkyl group in the
range of C10-C18 with not less than 50 percent C14-
C16)'' and ``Sodium sec-alkyl mono- and disulfonates (alkyl group
in the range of C10-C18 with not less than 50 percent
C14-C16)'' and by alphabetically adding a new entry under the
headings ``List of substances'' and ``Limitations'' to read as follows:
Sec. 178.3130 Antistatic and/or antifogging agents in food-packaging
materials.
* * * * *
(b) * * *
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List of substances Limitations
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Alkyl mono- and disulfonic acids, For use only:
sodium salts (produced from n-
alkanes in the range of C10-C18
with not less than 50 percent C14-
C16)..
1. As antistatic agents at levels
not to exceed 0.1 percent by
weight of polyolefin films that
comply with Sec. 177.1520 of this
chapter: Provided, That the
finished olefin polymers contact
foods of Types I, II, III, IV, V,
VIA, VIB, VII, VIII, and IX
described in Table 1 of Sec.
176.170(c) of this chapter, and
under conditions of use E, F, and
G described in Table 2 of Sec.
176.170(c) of this chapter.
2. As antistatic agents at levels
not to exceed 3.0 percent by
weight of polystyrene or rubber-
modified polystyrene complying
with Sec. 177.1640(c) of this
chapter under conditions of use B
through H described in Table 2 of
Sec. 176.170(c) of this chapter.
*******
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6. Section 178.3400 is amended in the table in paragraph (c) by
removing the entries for ``n-Alkylsulfonate (alkyl group is in the
range C10-C18 with not less than 50 percent C14-
C16)'' and ``Sodium sec-alkyl mono- and disulfonates (alkyl group
in the range of C10-C18 with not less than 50 percent
C14-C16)'' and by alphabetically adding a new entry under the
headings ``List of substances'' and ``Limitations'' to read as follows:
Sec. 178.3400 Emulsifiers and/or surface active agents.
* * * * *
(c) * * *
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List of substances Limitations
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Alkyl mono- and disulfonic acids, For use only:
sodium salts (produced from n-
alkanes in the range of C10-C18
with not less than 50 percent C14-
C16).
1. As provided in Sec. 176.170 of
this chapter.
2. At levels not to exceed 2
percent by weight of polyvinyl
chloride and/or vinyl chloride
copolymers complying with Sec.
177.1980 of this chapter.
3. As emulsifiers in vinylidene
chloride copolymer or homopolymer
coatings at levels not to exceed a
total of 2.6 percent by weight of
coating solids. The finished
polymer contacts food only of the
Types I, II, III, IV, V, VIA, VIB,
VII, VIII, and IX as identified in
Table 1 of Sec. 176.170(c) of this
chapter, and limited to conditions
of use E, F, and G described in
Table 2 of Sec. 176.170 of this
chapter.
4. As emulsifiers and/or surface-
active agents at levels not to
exceed 3.0 percent by weight of
polystyrene or rubber-modified
polystyrene complying with Sec.
177.1640(c) of this chapter under
conditions of use B through H
described in Table 2 of Sec.
176.170(c) of this chapter.
*******
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* * * * *
Dated: January 11, 1994.
Fred R. Shank,
Director, Center for Food Safety and Applied Nutrition.
[FR Doc. 94-1423 Filed 1-19-94; 4:15 pm]
BILLING CODE 4160-01-F
