from the United States Court of International Trade in No.
1:12-cv-00079-LMG, Judge Leo M. Gordon.
Matthew R. Nicely, Hughes Hubbard & Reed LLP, Washington,
DC, argued for plaintiff-appellant. Also represented by
Daniel Martin Witkowski; Robert L. LaFrankie, Aaron Michael
Marx, Crowell & Moring, LLP, Washington, DC.
Laufgraben, Commercial Litigation Branch, Civil Division,
United States Department of Justice, Washington, DC, argued
for defendant-appellee. Also represented by Chad A. Readler,
Jeanne E. Davidson, Claudia Burke; Paula S. Smith, Office of
the Assistant Chief Counsel, United States Bureau of Customs
and Border Protection, United States Department of Homeland
Security, New York, NY.
Dyk, Bryson, and Reyna, Circuit Judges.
Bryson, Circuit Judge.
customs classification case requires us to define the term
"amide" as used in the Harmonized Tariff Schedule
of the United States ("HTSUS"). In particular, we
are called on to distinguish between "Amides" and
"Other" in a heading of the HTSUS that covers
amides, their derivatives, and salts thereof. Chemtall, Inc.
appeals from a decision of the Court of International Trade
holding that Chemtall's product, acrylamido tertiary
butyl sulfonic acid ("ATBS"), is not an amide, but
is a derivative of an amide. Chemtall, Inc. v. United
States, 179 F.Supp.3d 1200 (Ct. Int'l Trade 2016).
2924 of the HTSUS covers carboxyamide-function compounds and
amide-function compounds of carbonic acids. All amides of
this type contain an amide functional group consisting of a
carbon atom (C), an oxygen atom (O), and a nitrogen atom (N),
in which there is a double bond between the carbon and oxygen
atoms, and a single bond between the carbon and nitrogen
atoms. This amide functional group contains three
substituents, or radicals (designated as R1,
R2, and R3), one of which is bonded to
the carbon atom and two of which are bonded to the nitrogen
atom. Each of the radicals R2 and R3
can be a hydrogen atom (H) or a group of atoms beginning with
a carbon atom bonded to the nitrogen atom. The functional
group has the following general structure:
amide with the general structure depicted above can be a
primary, secondary, or tertiary amide. An amide in which the
nitrogen atom is bonded to two hydrogen atoms (at locations R
2 and R3) and a carbon atom is called a
primary amide; it has the general structure
R-CONH2 . An amide in which the nitrogen atom is
bonded to one hydrogen atom and two structures each beginning
with a carbon atom is called a secondary amide; it has the
general structure R-CONHR'. An amide in which the
nitrogen atom is bonded to three structures each beginning
with a carbon atom is called a tertiary amide; it has the
general structure R-CONR'2 . The structures of
these three categories of amides can be depicted as follows:
Wade, Jr., Organic Chemistry 984 (8th ed. 2013);
see also Marc Loudon & Jim Parise, Organic
Chemistry 1048 (6th ed. 2016).
parties agree that in order to be considered an amide under
the tariff schedule, a compound must contain an amide
functional group. The central issue in this case is what
elements may be included in the radical groups so that the
entire compound will be considered an amide and when, with
the addition of other elements, the compound ceases to be an
dispute in this case involves the proper classification of 38
entries of ATBS during 2010 and 2011. ATBS contains (1) an
amide functional group and has a hydro-carbyl group in the
R1 position; (2) a hydrogen atom in the
R2 position; and (3) a compound containing
hydrogen, carbon, oxygen, and sulfur (S) atoms in the R
3 position. The structure of ATBS can be depicted
question before the court is whether the addition of the SO
3H group as part of the R 3 radical
means that the compound is not an amide within the meaning of
the HTSUS, but instead is a derivative of an amide.
parties do not dispute that ATBS is properly categorized
under heading 2924 of the HTSUS. Heading 2924 is divided into
two categories. The first category, which is titled
"Acyclic amides (including acyclic carbamates) and their
derivatives; salts thereof, " encompasses subheadings
2924.11 through 2924.19. The second category, which is titled
"Cyclic amides (including cyclic carbamates) and their
derivatives; salts thereof, " encompasses subheadings
2924.21 through 2924.29. The distinction between acyclic and
cyclic amides turns on whether the compound includes a cyclic
structure of atoms. Because ATBS does not contain such a ring
structure, it is acyclic.
part of subheading 2924 that addresses acyclic amides reads
time of the entries, Chemtall classified its shipments of
ATBS under subheading 29184.108.40.206, as "Other: Amides:
Acrylamide, " subject to a 3.7% duty rate. U.S. Customs
and Border Protection ("Customs") disagreed. In
notices of action issued in early 2011, Customs notified
Chemtall that it had determined that ATBS was not an amide
under subheading 2924.19.11 ("Amides"), but should
be reclassified under subheading 2924.19.80.00
("Other"), which carries a 6.5% duty rate. Chemtall
protested the reclassification, and Customs denied the
protests. Customs ruled that ATBS was not an acyclic amide,
but a sulphonated derivative of an acyclic amide and
therefore did not qualify as an "Amide"
classifiable under subheading 2924.19.11.
filed a complaint in the Court of International Trade seeking
review of Customs' decision. In that action, Chemtall
argued that the definition of an amide requires that the
three radical groups attached to the amide functional group
must consist of either hydrogen, a hydrocarbyl group, or what
Chemtall referred to as a "substituted hydrocarbyl"
group. Chemtall contended that the radical in the R
3 position of ATBS, which contains sulfur and
oxygen, is a substituted hydrocarbyl group, and that ATBS is
therefore an amide.
government argued that the radicals attached to an amide
functional group may consist only of hydrogen, alkyl groups,
or aryl groups. Both alkyl and aryl groups are hydrocarbyls
and do not contain sulfur or oxygen, so ATBS is excluded from
the government's definition of "amide."
cross-motions for summary judgment, the Court of
International Trade adopted the government's definition
of the term amide and held that ATBS is properly categorized