[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) *   *   *

------------------------------------------------------------------------
         List of substances                      Limitations            
------------------------------------------------------------------------
                                 *******                                
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.              
                                 *******                                
------------------------------------------------------------------------

* * * * *
    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) *   *   * 

------------------------------------------------------------------------
         List of substances                      Limitations            
------------------------------------------------------------------------
                                 *******                                
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).                                                                  
                                 *******                                
------------------------------------------------------------------------

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) *   *   *

------------------------------------------------------------------------
         List of substances                      Limitations            
------------------------------------------------------------------------
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. 
                                 *******                                
------------------------------------------------------------------------

    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) *   *   *

------------------------------------------------------------------------
        List of substances                       Limitations            
------------------------------------------------------------------------
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.       
                                 *******                                
------------------------------------------------------------------------

* * * * *

    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