CLA-2 CO:R:C:F 951276 EAB
District Director
U.S. Customs Service
P.O. Box 37260
Milwaukee, Wisconsin 53237-0260
Re: Application for Further Review of Protest No. 3701-91-
100045, dated October 10, 1990, concerning cycl-
isopropylidene methylmalonate; 2,2,5-trimethyl-1,3-dioxane-
4,6-dione; CAS 3709-18-0; polyhydric alcohols; Meldrum's
Acid; polybasic acids; polycarboxylic acids; cyclic esters;
Legal Note 7, Chapter 29; malonic acid; ethyl malonate; 2917
Dear Sir:
This is a decision on a protest filed July 30, 1991, against
your decision in the classification of merchandise liquidated on
May 10, 1991.
FACTS:
The protestant entered all goods in subheading 2932.29.5050,
Harmonized Tariff Schedule of the United States Annotated
(HTSUSA), a provision for heterocyclic compounds with oxygen
hetero-atoms(s) only; lactones; lactones other coumarin,
methylcoumarins and ethylcoumarins; other lactones other than
aromatic; other; other, such compounds being dutiable at the
column 1 general rate of 3.7 percent ad valorem.
Customs reclassified the merchandise under subheading
2917.19.5050, HTSUSA, a provision for polycarboxylic acids, their
anhydrides, peroxides and peroxyacids; acyclic polycarboxylic
acids, their anhydrides, peroxides, peroxyacids and their
derivatives; other; other; other; other, such compounds being
dutiable at the column 1 general rate of 4.0 percent ad valorem.
Protestant seeks reclassification of the goods to subheading
2932.29.5050.
The compound is of a cyclic structure and is also known as
methyl Meldrum's Acid, which itself is found in the chemical
literature as malonic acid cyclic isopropylidene ester, see,
e.g., 5696, The Merck Index, Eleventh Edition.
O
\\
H3C C6---O1 CH3
\ / \ /
C5 C2 METHYL MELDRUM'S ACID
/ \ / \ 2,2,5-TRIMETHYL-1,3-DIOXANE-4,6-DIONE
H C4---O3 CH3
//
O
ISSUE:
What is the proper classification under the HTSUSA of cycl-
isopropylidene methylmalonate, or 2,2,5-trimethyl-1,3-dioxane-
4,6-dione, having CAS Registry Number 3709-18-0?
LAW AND ANALYSIS:
Merchandise imported into the U.S. is classified under the
HTSUSA. Tariff classification is governed by the principles set
forth in the General Rules of Interpretation (GRIs) and, in the
absence of special language or context which otherwise requires,
by the Additional U.S. Rules of Interpretation. The GRIs and the
Additional U.S. Rules of Interpretation are part of the HTSUSA
and are to be considered statutory provisions of law for all
purposes.
GRI 1 requires that classification be determined first
according to the terms of the headings of the tariff schedule and
any relative section or chapter notes and, unless otherwise
required, according to the remaining GRI's taken in order.
Heading 2917 describes, inter alia, polycarboxylic acids,
their anhydrides, peroxides and peroxyacids. Thereunder, acyclic
polycarboxylic acids and their esters and derivatives are to be
classified. Subheading 2917.19, HTSUSA.
Heading 2932 describes heterocyclic compounds with oxygen
hetero-atom(s) only. In particular, lactones other than
coumarin, methylcoumarins and ethylcoumarins are classifiable
under subheading 2932.29, HTSUSA.
Note 7, Chapter 29 provides that "[neither] anhydrides of
polybasic carboxylic acids * * * [nor] cyclic esters of
polyhydric alcohols * * * with polybasic acids * * *" fall to be
classified under heading 2932. Such compounds are to be
classified in heading 2917, see Explanatory Note 29.32.
Malonic acid, having the structure HOOCCH2COOH, or
(COOH)2CH2, is identified in the chemical literature as
methanedicarboxylic acid, i.e., as a polycarboxylic acid.
An anhydride is a chemical compound derived from an organic
acid by elimination of a molecule of water. Generally,
anhydrides are called "anhydrides," e.g, the anhydride of maleic
acid is called maleic anhydride.
An ester is an organic compound derived from an acid by the
exchange of the replaceable hydrogen of the acid for an organic
radical. Generally, esters are denominated with the suffix
"-ate," e.g., the ester of malonic acid is ethyl malonate.
A lactone is the inner ester of a carboxylic and is derived
from the acid by the exchange of the replaceable hydrogen of the
acid for an organic radical. In other words, a lactone is a
cyclic ester.
Cyclization of a dicarboxylic acid by replacing both
hydroxyl (-OH) groups with identical radicals yields a double
ester ring known as a lactide. In fact, in The Merck Index,
Eighth Edition we find "lactide," 3,6-dimethyl-2,5-p-
dioxanedione, also written as 2,5-dioxo-3,6-dimethyl-1,4-dioxane
and 3,6-diketo-2,5-dimethyl-1,4-dioxane (at p. 605). Noticeably,
another name for Meldrum's Acid is 2,2-dimethyl-4,6-diketo-1,3-
dioxane.
The isopropylidene moiety of the subject compound is an
organic radical, recognizable as a derivative of 2,2-propane-
diol.
Whether methyl Meldrum's Acid is a derivative of a
polycarboxylic acid, namely malonic acid, or a derivative of a
polybasic alcohol, namely 2,2-propane-diol with a polybasic acid,
Note 7, Chapter 29 prohibits its classification under heading
2932.
The subheadings of heading 2917 separately describe three
categories of compounds together with their respective
derivatives: acyclic polycarboxylic acids and their derivatives;
cyclic polycarboxylic acids and their derivatives; and, aromatic
polycarboxylic acids and their derivatives.
Explanatory Note 29.17 (A)(7) indicates that malonic acid,
the most important esters of which include diethyl malonate,
falls to be classified under heading 2917, a provision for
acyclic polycarboxylic acids and their esters, salts and
derivatives. In this case, for tariff purposes, a cyclic
compound is acyclic due to its derivation.
HOLDING:
You are instructed to deny the protest.
Cycl-isopropylidene methylmalonate, or 2,2,5-trimethyl-1,3-
dioxane-4,6-dione, having CAS Registry Number 3709-18-0 and also
known as methyl Meldrum's Acid, is classifiable under subheading
2917.19.5050, a provision describing polycarboxylic acids;
acyclic polycarboxylic acids, their anhydrides and their
derivatives; other; other; other; other. Articles classified
under that subheading for the year 1991 were subject to a column
1 general rate of duty of 4.0 percent ad valorem.
A copy of this decision should be attached to the Customs
Form 19 and provided to the protestant as part of the notice of
action on the protest.
Sincerely,
John Durant, Director
Commercial Rulings Division