CLA–2 OT:RR:CTF:TCM H195904 AMM
Mr. J. Michael Taylor
King & Spalding LLP
1700 Pennsylvania Ave, NW
Suite 200
Washington DC, 20006-4707
RE: Request for Reconsideration of New York Ruling Letter N178696; Classification of allyl bromide (CAS No. 106-95-6)
Dear Mr. Taylor,
This is in regard to your request, dated December 6, 2011, submitted on behalf of Albemarle Corporation, for reconsideration of New York Ruling Letter (NY) N178696, issued to you on September 27, 2011, regarding the classification under the Harmonized Tariff Schedule of the United States (HTSUS), of the chemical identified as “allyl bromide” (Chemical Abstract Service (CAS) No. 106-95-6). In NY N178696, U.S. Customs and Border Protection (CBP) classified this product under heading 2903, HTSUS, specifically under subheading 2903.39.20, HTSUS, which provides for: “Halogenated derivatives of hydrocarbons: Fluorinated, brominated or iodinated derivatives of acyclic hydrocarbons: Other: Other”. In reaching our decision, we have considered your request for reconsideration, an additional submission made on January 24, 2013, and comments made during a meeting with CBP officials on January 30, 2013.
FACTS:
The product at issue is identified as Allyl Bromide (CAS No. 106-95-6). You state that it is imported as a liquid, in its neat, undiluted form. It has the chemical formula C3H5Br, and contains two double-bonded carbon atoms. It is derived from the chemical Propene (CAS No. 115-07-1). The chemical structures of both Propene and Allyl Bromide are compared below:
Propene (CAS No. 115-07-1)
Allyl Bromide (CAS No. 106-95-6)
In NY N178696, dated September 27, 2011, CBP considered the classification of the instant product. In that ruling, CBP stated that: “Allyl bromide is a brominated derivative of an acyclic hydrocarbon. The product is indicated for use in the manufacture of an alkylated sugar additive used to produce clarifiers for plastics. You also state that the product can be used as a reagent to manufacture pharmaceutical intermediates.” CBP classified the instant product under heading 2903, HTSUS, specifically under subheading 2903.39.20, HTSUS, which provides for: “Halogenated derivatives of hydrocarbons: Fluorinated, brominated or iodinated derivatives of acyclic hydrocarbons: Other: Other”.
ISSUE:
Whether allyl bromide is properly classified under subheading 2903.39.15, HTSUS, which provides for “Halogenated derivatives of hydrocarbon: [B]rominated … derivatives of acyclic hydrocarbons: Other: [A]lkyl bromides …”, or under subheading 2903.39.20, HTSUS, which provides for “Halogenated derivatives of hydrocarbon: [B]rominated … derivatives of acyclic hydrocarbons: Other: Other”.
LAW AND ANALYSIS:
Classification of goods under the HTSUS is governed by the General Rules of Interpretation (GRI). GRI 1 provides that classification shall be determined according to the terms of the headings of the tariff schedule and any relative section or chapter notes. In the event that the goods cannot be classified solely on the basis of GRI 1, and if the headings and legal notes do not otherwise require, the remaining GRI may then be applied.
The 2013 HTSUS provisions at issue are as follows:
2903 Halogenated derivatives of hydrocarbons:
Fluorinated, brominated or iodinated derivatives of acyclic hydrocarbons:
2903.39 Other:
2903.39.15 Acetylene tetrabromide; Alkyl bromides; Methylene dibromide; and Vinyl bromide
2903.39.20 Other
Additional U.S. Note 2 to Section VI, HTSUS, states, in pertinent part:
For the purposes of the tariff schedule:
* * *
(c) For the purposes of headings 2902, 2907 and 3817, the term “alkyl” describes any saturated acyclic hydrocarbon group having six or more carbon atoms or, subject to note 1 to chapter 29, any mixtures of such groups averaging six or more carbon atoms.
Note 1 to Chapter 29, HTSUS, states, in pertinent part: “Except where the context otherwise requires, the headings of this chapter apply only to: (a) Separate chemically defined organic compounds, whether or not containing impurities; …”.
The Harmonized Commodity Description and Coding System Explanatory Notes (ENs), constitute the official interpretation of the Harmonized System at the international level. While neither legally binding nor dispositive, the ENs provide a commentary on the scope of each heading of the HTSUS and are generally indicative of the proper interpretation of the headings. It is CBP’s practice to consult, whenever possible, the terms of the ENs when interpreting the HTSUS. See T.D. 89–80, 54 Fed. Reg. 35127, 35128 (August 23, 1989).
EN 29.03 states, in pertinent part:
These are compounds obtained by the substitution in the structural formula of a hydrocarbon of one or more halogen atoms (fluorine, chlorine, bromine, iodine) for an equal number of hydrogen atoms.
* * *
(C) FLUORINATED, BROMINATED OR IODINATED DERIVATIVES OF ACYCLIC HYDROCARBONS
* * *
(4) Allyl bromide.
* * *
The instant product is an organic chemical, imported in a pure, liquid form. See Note 1(a) to Chapter 29, HTSUS. In NY N178696, CBP classified the instant product under heading 2903, HTSUS, specifically under subheading 2903.39.20, HTSUS, which provides for “Halogenated derivatives of hydrocarbons: Fluorinated, brominated or iodinated derivatives of acyclic hydrocarbons: Other: Other”. You object to CBP’s classification at the 8-digit level, and allege that the proper classification of the instant merchandise is under subheading 2903.39.15, which provides, in pertinent part, for: “Halogenated derivatives of hydrocarbons: Fluorinated, brominated or iodinated derivatives of acyclic hydrocarbons: Other: … alkyl bromides …”.
Heading 2903, HTSUS, provides for halogenated derivatives of hydrocarbons. EN 29.03 states that the heading includes “compounds obtained by the substitution in the structural formula of a hydrocarbon of one or more halogen atoms (… bromine …) for an equal number of hydrogen atoms.” With respect to the instant product, the starting hydrocarbon is propene, whose chemical structure is C3H6. Allyl bromide is obtained by removing one of the hydrogen atoms from the carbon atom without a double-bond, and replacing that hydrogen atom with a bromine atom. Therefore, allyl bromide is a halogenated derivative of a hydrocarbon, and is properly classified under heading 2903, HTSUS. See EN 29.03(C)(4).
The dispute in the case comes at the 8-digit subheading level. As a result, GRI 6 applies, which states:
For legal purposes, the classification of goods in the subheadings of a heading shall be determined according to the terms of those subheadings and any related subheading notes and, mutatis mutandis, to the above rules on the understanding that only subheadings at the same level are comparable. For the purposes of this rule, the relative section, chapter and subchapter notes also apply, unless the context otherwise requires.
At issue is whether or not the instant product is considered an “alkyl bromide” as provided by subheading 2903.39.15, HTSUS. The phrase “alkyl” is defined in Additional U.S. Note 2(c) to Section VI, HTSUS, but that definition only applies to headings 2902, 2907, and 3817, HTSUS. See, e.g., Blakley Corp. v. United States, 15 F. Supp. 2d 865, at 869-870. When a tariff term is not defined by the HTSUS or its legislative history, “the term’s correct meaning is its common meaning.” Mita Copystar Am. v. United States, 21 F.3d 1079, 1082 (Fed. Cir. 1994). The common meaning of a term used in commerce is presumed to be the same as its commercial meaning. Simod Am. Corp. v. United States, 872 F.2d 1572, 1576 (Fed. Cir. 1989). To ascertain the common meaning of a term, CBP may consult “dictionaries, scientific authorities, and other reliable information sources” and “lexicographic and other materials.” C.J. Tower & Sons v. United States, 673 F.2d 1268, 1271 (C.C.P.A. 1982); Simod, 872 F.2d at 1576.
The term “alkyl” is defined as “a parafinnic hydrocarbon group which may be derived from an alkane by dropping one hydrogen from the formula.” Hawley’s Condensed Chemical Dictionary, 15th Ed., p. 38 (Wiley, 2007). The phrase “alkyl groups” is defined as “univalent groups derived from alkanes by removal of a hydrogen atom from any carbon atom: CnH2n+1-.” Moss et. al., “Glossary of Class Names of Organic Compounds and Reactive Intermediates Based on Structure (IUPAC Recommendations 1995),” Pure and Applied Chemistry, vol. 67, No. 8/9, p. 1314 (IUPAC, 1995). According to Hawley, the term “alkane” is equivalent to “paraffin,” which is defined as “a class of aliphatic hydrocarbons characterized by a strait or branched carbon chain; generic formula CnHn+2.” Hawley, at pp. 39, 944. By contrast, Hawley defines the term “alkene” to be equivalent to “olefin,” which is defined as “A class of unsaturated aliphatic hydrocarbons having one or more double bonds[.]” Hawley, at pp. 38, 924. According to Moss et. al., “alkanes” are “Acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and therefore consisting entirely of hydrogen atoms and saturated carbon atoms.” Moss et. al., p. 1313.
Therefore, in order to be considered an alkyl bromide, the hydrocarbon from which the instant chemical is derived must be an alkane; in other words, it cannot contain a carbon-carbon double bond. An alkyl bromide of subheading 2903.39.15, HTSUS, must have the general formula CnH2n+1Br. The instant product is derived from the chemical propene, an alkene containing a carbon-carbon double bond. It’s chemical formula, C3H5Br, does not meet the required general formula. Therefore, it is not an “alkyl bromide,” and cannot be classified under subheading 2903.39.15, HTSUS. Instead, the instant product is classified under subheading 2903.39.20, HTSUS, which provides for “Halogenated derivatives of hydrocarbons: Fluorinated, brominated or iodinated derivatives of acyclic hydrocarbons: Other: Other”.
This is consistent with previous CBP rulings, in which certain alkane derived compounds were classified as “alkyl bromides.” In NY N024404, dated March 17, 2008, CBP considered the classification of n-hexyl bromide, a straight chain halogenated derivative of hexane. CBP found that it was classified under heading 2903, HTSUS, specifically under subheading 2903.39.15, HTSUS, as an “alkyl bromide.” In NY N017307, dated October 1, 2007, CBP considered the classification of 2-bromo-2-methyl propane, which is derived from isobutane. CBP found that it was classified under heading 2903, HTSUS, specifically under subheading 2903.39.15, HTSUS, as an “alkyl bromide.” In NY N189998, dated November 22, 2011, CBP considered the classification of “Techkleen BO,” a product composed of more than 98% N-Propyl Bromide, CAS No. 106-94-5. CBP found that it was classified under heading 2903, HTSUS, specifically under subheading 2903.39.15, HTSUS, as an “alkyl bromide.” Likewise, in NY N026779, dated August 1, 2008, CBP considered “n-propyl bromide C30,” a product comprised of n-propyl bromide with an added stabilizer, namely 1,2-epoxybutane (CAS No. 106-88-7), and found that it was classified under heading 2903, HTSUS, specifically under subheading 2903.39.15, HTSUS, as an “alkyl bromide.”
In NY M81098, dated March 16, 2006, CBP considered the classification of 3-bromo-1-propene, which is an alternate name for allyl bromide. CBP found that it was classified under heading 2903, HTSUS, specifically under subheading 2903.30.20, HTSUS (2001), which provides for “Halogenated derivatives of hydrocarbons: Fluorinated, brominated or iodinated derivatives of acyclic hydrocarbons: Other.” In NY G84036, dated January 29, 2001, CBP considered the classification of 4-bromo-1-butene, which has a structure similar to the instant product, except that it contains an additional carbon atom. CBP found that it was classified under heading 2903, HTSUS, specifically under subheading 2903.30.20, HTSUS (2001). In NY D85966, dated February 3, 1999, CBP considered the classification of 3-bromo-1-propyne, which has a structure similar to the instant product, except that it has a triple bond in place of the double bond. CBP found that it was classified under heading 2903, HTSUS, specifically under subheading 2903.30.20, HTSUS (1999). We note that subheading 2903.30.20, HTSUS, was superseded by 2903.39.20, HTSUS, on February 3, 2007. See Presidential Proclamation 8097, dated December 29, 2006; 72 Fed. Reg. 453-458; USITC Publication 3898, dated December 2006, Annex I, p. 18 (available at ).
allyl bromide (C3H5Br)
NY M81098 and NY N178696
n-hexyl bromide (C6H13Br)
NY N024404 (2903.39.15)
4-bromo-1-butene (C4H7Br)
NY G84036
2-bromo-2-methyl propane (C4H9Br)
NY N017307 (2903.39.15)
3-bromo-propyne (C3H3Br)
NY D85966
n-propyl bromide (C3H7Br)
NY N189998 and NY N026779
(2903.39.15)
The rulings identified above are consistent with the proposition that, in order for a product to be considered an alkyl bromide of subheading 2903.39.15, HTSUS, it cannot contain a carbon-carbon double bond. The products considered in NY N024404, NY N017307, NY N189998, and NY N026779 each have the general formula CnH2n+1Br. The products considered in NY M81098, NY N178696, NY G84036, and NY D85966 do not meet this general formula.
You assert that the phrase “alkyl” has a different meaning. According to page 5 of your December 6, 2011 submission, allyl bromide is an “alkyl bromide” simply because the bromine is attached to a saturated sp3 carbon atom. You also assert that a product may be classified as such regardless of whether the compound contains a carbon-carbon double or triple bond anywhere in its chemical structure, as long as the carbon to which the bromine is bonded only has single bonds.
In support of this assertion, you provide several definitions, specifically: “alkyl halide: a compound containing a halogen atom covalently bonded to an sp3 hybridized carbon atom.” See Wamser, Chapter 7 Lecture Notes for Organic Chemistry 334 (Portland State University, 1999); “an alkyl halide or haloalkane is a compound that has one or more halogen atoms bonded to a saturated carbon.” See OChemPal website (Utah Valley University, 2009); “an alkyl halide is another name for a halogen substituted alkane. The carbon atom, which is bonded to the halogen atom, has sp3 hybridized bonding orbitals and exhibits a tetrahedral shape.” See CliffsNotes.com, Introduction to Alkyl Halides (last checked on April 3, 2013); “In alkyl halides all four bonds to the carbon atom that bears the halogen are single bonds[.]” See www.britannica.com, entry for “organohalogen compound” (last checked on April 3, 2013). Your submissions also cite to wikipedia.org for definitions of the terms “alkyl halide” and “haloalkane,” and cite to various textbooks and reference books that refer to allyl bromide as a type of alkyl bromide.
While it is true that you cite to sources which provide an alternative definition for the term “alkyl,” it is CBP’s position that the definition of “alkyl groups” provided by Moss, et. al., is determinative of the common meaning. This definition was published under the auspice of the International Union of Pure and Applied Chemistry (IUPAC), an international organization which has “long been recognized as the world authority on chemical nomenclature, terminology, standardized methods for measurement, atomic weights and many other critically evaluated data.” See . Moss, et. al., defines “alkyl groups” in terms of the general formula “CnH2n+1-”, meaning that an alkyl halide must necessarily have the formula CnH2n+1X (where X is any halogen), and that alkyl bromide must necessarily have the formula CnH2n+1Br. As it is impossible to create a chemical which has a carbon-carbon double or triple bond and still meet this generic formula, an alkyl halide must be fully saturated. The rulings identified above, namely, NY N024404, NY N017307, NY N189998, NY N026779, NY M81098, NY N178696, NY G84036, and NY D85966, are consistent with this IUPAC definition.
HOLDING:
By application of GRI 1 and GRI 6, the chemical known as allyl bromide (CAS No. 106-95-6) is classified under heading 2903, HTSUS, specifically under subheading 2903.39.20, which provides for “Halogenated derivatives of hydrocarbons: Fluorinated, brominated or iodinated derivatives of acyclic hydrocarbons: Other: Other”. The general, column one rate of duty is 3.7% ad valorem.
Duty rates are provided for your convenience and are subject to change. The text of the most recent HTSUS and the accompanying duty rates are provided on the internet at www.usitc.gov/tata/hts/.
EFFECT ON OTHER RULINGS:
New York Ruling N178696, dated September 27, 2011, is AFFIRMED.
Sincerely,
Myles B. Harmon, Director
Commercial and Trade Facilitation Division