74 Cust. Ct. 138 | Cust. Ct. | 1975
The question involved in these 14 consolidated actions is the dutiable tariff status of certain merchandise invoiced as “Cresylic Compounds Grade 2490,” which was manufactured in West Germany, shipped from the Netherlands and entered at the port of Los Angeles at various times between January 1968 and February 1970.
The merchandise was classified and assessed for duty under item 403.46, Tariff Schedules of the United States (TSUS), as other coal tar distillates which on being subjected to distillation yield in the portion distilling below 215° C. a quantity of tar acids equal to or more than 75% by weight of the original distillate.
Plaintiff does not dispute that the merchandise is a coal tar distillate within the meaning of the tariff schedules, but contends that the importations are dutiable under a more specific provision, item 403.42, TSUS, as cresylic acid which on being subjected to distillation yields in the portion distilling below 215° C. a quantity of tar acids equal to or more than 75% by weight of the original distillate.
Defendant contends, alternatively, in its amended answer that if the court should find that the imported merchandise is not a distillate of coal tar it is properly dutiable under the basket provision of item 403.60, TSUS, as other cyclic organic chemical products in any physical form having a benzenoid, quinoid, or modified benzenoid structure, not provided for in subpart A or C of part 1 of schedule 4.
Schedule 4. - Chemicals and Related Peoducts * * * * * *
Schedule 4 headnotes:
* * * * sf: sfc *
2. (a) The term “compounds”, as used in this schedule, means substances occurring naturally or produced artificially by the reaction of two or more ingredients, each compound—
(i) consisting of two or more elements,
(ii) having its own characteristic properties different from those of its elements and from those of other compounds, and
(iii) always consisting of the same elements united in the same proportions by weight with the same internal arrangement.
The presence of impurities which occur naturally or as an incident to production does not in itself affect the classification of a product as a compound.
(b) The term “compounds”, as used in this schedule, includes a solution of a single compound in Avater, and, in determining the amount of duty on any such compound subject to duty in this schedule at a specific rate, an alloAvance in Aveight or volume, as the case may be, shall be made for the water in excess of any AA^ater of crystallization which may have been in the compound.
3. (a) The term “'mixtures”, as used in this schedule, means substances consisting of íavo or more ingredients (i.e., elements or compounds), Avhether occurring as such in nature, or whether artificially produced (i.e., brought about by mechanical, physical, or chemical means), Avhich do not bear a fixed ratio to one another and Avhich, however thoroughly commingled, retain their individual chemical properties and are not chemically united. The fact that the ingredients of a product are incapable of separation or have been commingled in definite proportions does not in itself affect the classification of such product as a mixture.
(b) The term “mixtures”, as used in this schedule, includes solutions, except solutions defined as compounds in headnote 2(b) of this schedule.
PART 1. - Benzenoid Chemicals and Peoducts
$ ‡ ‡ $ if: ‡
*140 Subpart A. - Organic Chemical Crudes
Coal tar, crude (including crude blast-furnance tar, crude oil-gas tar, and crude water-gas tar), and organic chemical products found naturally in coal tar, whether produced or obtained from coal tar or other source:
*******
401.24 Cresylic acid which on being subjected to distillation yields in the portion distilling below 190°C. a quantity of tar acids less than 5% by weight of the original distillate, and which on being subjected to distillation yields in the portion distilling below 215°C. a quantity of tar acids less than 75% by weight of the original dis-tillate_ Free
*******
401.76 Xylenols which on being subjected to distillation yield in the portion distilling below 190°C. a quantity of tar acids less than 5% by weight of the original distillate, and which on being subjected to distillation yield in the portion distilling below 215°C. a quantity of tar acids less than 75% by weight of the original distillate_ Free
*******
Subpart B. - Industrial Organic Chemicals
Subpart B headnote:
1. The provisions of items 403.02 to 403.60, inclusive, in this subpart shall apply not only to the products described therein when obtained, derived, or manufactured in whole or in part from products described in subpart A of this part, but shall also apply to products of like chemical composition having a benzenoid, quinoid, or modified benzenoid structure artificially produced by synthesis, whether or not obtained, derived, or manufactured in whole or in part from products described in said subpart A.
*141 Cyclic organic chemical products in any physical form having a benzenoid, quinoid, or modified benzenoid structure, not provided for in subpart A or C of this part:
* * * * * * *
All distillates of coal tar, blast-furnace tar, oil-gas tar, and water-gas tar, which on being subjected to distillation yield in the portion distilling below 190°C. a quantity of tar acids equal to or more than 5% by weight of the original distillate or which on being subjected to distillation yield in the portion distilling below 215°C. a quantity of tar acids equal to or more than 75% by weight of the original distillate:
Phenol (carbolic acid) which on being subjected to distillation yields in the portion distilling below 190°C. a quantity of tar acids equal to or more than 5% by weight of the original distillate_ 403.40 [Dutiable]
Cresylic acid which on being subjected to distillation yields in the portion distilling below 215°C. a quantity of tar acids equal to or more than 75% by weight of the original distillate_ [Claimed] 403.42 [Dutiable]
Metacresol, orthocresol, para-cresol, and metaparacresol, all the foregoing having a purity of 75% or more by 403.44 [Dutiable]
Other_ [Classified] 4013.46 * * * * * [Dutiable]
[Defendant’s alternative claim] 403.60 Other_ [Dutiable]
Plaintiff’s position is that the designation in item 403.42 for cresylic acid is an eo nomine one which includes all forms of the article; that the term “cresylic acid” embraces a broad range of related chemical products in varying combinations and concentrations; and that it encompasses a product such as the merchandise in question even though it contains a very high concentration of a single isomer, in this case 2,4 xylenol.
Defendant contends, on the other hand, that the term cresylic acid is more limited in scope and that it does not include a product containing such high percentages of a single chemical compound as the present importations. It further argues that the imported merchandise is essentially a pure compound known and recognized as 2,4 xylenol, not as cresylic acid, and that the arrangement of the tariff schedules in subparts A and B of part 1 of schedule 4 clearly shows a Congressional intent to distinguish between “cresylic acid” and “xylenol” as products of trade and commerce.
Thus the primary question presented to the court is whether the merchandise in question comes within the common understanding of the term cresylic acid. Unless a differing commercial designation is claimed, the common meaning of the term, which presumptively is the same as its commercial meaning, will control. Marshall Field & Co. v. United States, 45 CCPA 72, C.A.D. 676 (1958).
Since the common meaning of a tariff term is a question of law, the court may, in addition to receiving testimony of witnesses, which is advisory only, consult extrinsic sources such as dictionaries, textbooks, scientific treatises and government publications as an aid in determining that meaning. United States v. Victoria Gin Co., Inc., et al., 48 CCPA 33, C.A.D. 759 (1960); Sandoz Chemical Works, Inc. v. United States, 43 CCPA 152, C.A.D. 623 (1956); B. Axelrod & Co. v. United States, 70 Cust. Ct. 117, C.D. 4417 (1973).
As a point of reference, the court is guided at the outset by the statements in the Tariff Classification Study - Explanatory and Background Materials, Schedule 4 (Nov. 15, 1960) (hereinafter Study) that wherever possible, the products named in schedule 4
In order to understand the “new terminology” adopted in part 1 of schedule 4 it is helpful to consider the chemical nature of coal tar and the products obtained therefrom by distillation insofar as they are relevant to the importations in question.
Coal tar is a viscous oily liquid obtained as a coke-oven by-product in the distillation of bituminous coal. It is a raw material which serves as a source of many organic chemical compounds which are obtained from fractional distillates of the coal tar.
A typical primary distillation of coal tar will yield approximate!y the following fractions at the following boiling ranges: In the boiling range up to 200° C., light oil; in the boiling range, 200°-250° C., middle oil which is also known as creosote or tar acid oil; in the boiling range 250°-300° C., heavy oil; in the boiling range 300°-350° C., anthracene oil. The residue from the distillation is coal tar pitch.
The middle oil or tar acid oil fraction contains napthalone and the tar acids. The tar acids, which comprise the phenols or phenolic compounds present in coal tar, consist almost entirely of a mixture of: Phenol; cresols (also known as methyl phenols); xylenols (also known as dimethyl phenols); and other high-boiling tar acids consisting of ethyl phenols and trimethyl phenols. Phenolic compounds are 6-membered hydrocarbon rings which have a hydroxyl (OH) group attached to a ring carbon atom in place of the hydrogen atom. Thus, “phenol” or carbolic acid (C6H5OII) the simplest of the phenols, has a hydroxyl or OH group in the first position of the 6-membered hydrocarbon ring as depicted in the following diagram:
orthocresol (ortho methyl phenol)
metacresol (meta methyl phenol)
paracresol (para methyl phenol)
Xylenols — which as previously noted are also known as dimethyl phenols ((CH3)206H30H) — have two methyl groups substituting for two hydrogen atoms and may be processed to yield six xylenol isomers as shown in the following diagram:
*145 
2,3xylenol (2,3 dimethyl phenol)
2,4xylenol (2,4 dimethyl phenol)
2,5xylenol (2,5 dimethyl phenol)
2,6xylenol (2,6 dimethyl phenol)
3,4 xylenol (3,4 dimethyl phenol)
3,5 xylenol (3,5 dimethyl phenol)
Against this background, plaintiff contends that the term “cresylic acid” applies to a mixture of phenols or phenolic compounds derived from coal tar or petroleum distillates, and that it can include any combination of such compounds in varying concentrations including up to 90%, or even higher, of an individual isomer. Thus, according to Mr. Ernest E. Chipman, a chemical engineer and president of the plaintiff-importing company, a special grade of cresylic acid may be present as a single isomer in a product containing up to 90% of that isomer and still be considered cresylic acid. For example, he testified that cresylic acid could contain from 0% to 90% of 2,4 xylenol. He agreed, however, that since the term “cresylic acid” is a family name that covers a broad range of compounds and does not describe a specific product, an order for cresylic acid would have to specify the grade designation.
Plaintiff also claims that its position reflects the trade practice of describing any combination of phenols, cresols and xylenols as cresylic acid or cresylics, and has offered evidence, discussed below, of what it considers to be the trade practice of treating products with a high xylenol content as cresylic acid.
Defendant, on the other hand, argues that phenolic products containing a high concentration of an individual isomer are not known as cresylic acid but by the name of the concentrated individual isomer. In other words, in defendant’s view, while a mixture of cresols or xylenols might be termed cresylic acid, a product containing' a high concentration of a single isomer such as 2,4 xylenol would be known and sold as 2,4 xylenol.
It is apparent from the record (both parties offered evidence of trade practice in support of their respective positions), the legislative history and the technical literature that the term “cresylic acid”
It is also used to describe a mixture of phenols, including cresols and xylenols. Thus, both definitions are found in Webster’s Third New International Dictionary (1963), as follows:
cresylic acid n 1: cresol: esp: a crude mixture of the three cresols 2: a mixture of phenols (as cresols and xylenols) obtained from coal tar or cracked petroleum oils.11
4 Kirk and Othmer, Encyclopedia of Chemical Technology (1949) contains the following comment (p. 601):
* * * Another ambiguity in cresol terminology is the use of the name “cresylic acid” for cresols. At times the term cresylic acid has designated a wide-boiling mixture of phenolics containing the three cresols, occasionally including phenol but at other times referring to all phenolics except phenol itself. The same name has also been applied specifically to cresols. With the current industrial trend toward separation and utilization of the individual isomers, the cresols are generally designated as such and cresylic acid more frequently refers, in a collective sense, to phenolic mixtures boiling above the cresol range.
In a discussion of the provisions for coal tar products in the Tariff Act of 1930, 1 Summaries oj Tariff Information pt. 2 (1948) states at p. 71 that—
* * * In commercial terminology the term cresols is also applied loosely to mixtures of the three isomers, which also*148 include a small proportion of phenol and high-boiling tar acids, and the term cresylic acid is applied to a mixture of cresols containing a large proportion of high-boiling tar acids. * * *
The lack of a precise meaning for cresylic acid was noted (and criticized) over 35 years ago by the Tariff Commission in its report, ¡synthetic Resins and their Raw Materials, Report No. 131 (2d ser. 1938). The Commission stated (p. 119):
Cresylic acid. — Cresylic acid is a generic term now applied to mixtures of tar acids in widely varying proportions. As defined in the literature and as formerly used in commerce the term identified a mixture of ortho, meta, and para cresols in the proportions in which they occur in coal tar. This proportion is approximately 40 percent metacresol, 35 percent orthocresol, and 25 percent para-cresol. But in recent years the designation cresylic acid has been applied to all sorts of mixtures of tar acids boiling above 190°C. Practically every maker of synthetic resins, antiseptics, and disinfectants has his own specifications for cresylic acid; it may be any mixture in almost any proportions of the three cresols, the six isomeric xylenols, and the higher boiling tar acids. Imports of crude cresylic acid are understood to be largely xylenol mixtures containing low percentages of the cresols. This loose application of cresylic acid in recent years is due to the increased commercial application of the high-boiling tar acids, especially the xylenols.
* * * The provision in paragraph 27 reads, "cresylic acid which on being subjected to distillation yields in the portion distilling below two hundred and fifteen degrees centigrade, a quantity of tar acids equal to or more than 75 per centum of the original distillate.” Under this provision cresylic acid may include an endless number of combinations of tar acids and may or may not contain any of the isomeric cresols. Of the 17 or more tar acids known to exist in coal tar (see table 56), only 8 have boiling points above 215°C. It would seem to be more accurate and more in line with present day usage to have the tariff drop the designation cresylic acid in favor of more definite terms based on composition, such as cresols and cresol mixes, xylenol and xylenol mixes, etc.
It is evident from the foregoing statements that, despite the vagaries of its application, the term cresylic acid has always been used to denote a mixture of phenolic compounds, whether it be a mixture of cresols or of the various high-boiling tar acids. However, the term is not used to describe products consisting predominantly of a highly concentrated phenolic isomer, such as orthocresol or 2,4 xylenol. To the contrary, the record establishes that such products are described and offered for sale under the name of that isomer and not as cresylic acid.
Thus, examination of various catalogues and brochures issued by domestic manufacturers of coal tar products (most of which were placed in evidence by plaintiff) reveals that, of the various tar acid products listed, those which are designated and offered for sale as “cresylic acid” are unvaryingly mixtures of two or more isomers,
One example is an undated publication issued some time after 1949 (see plaintiff’s exhibit 3, defendant’s exhibit B, and court exhibit 1) listing the products offered by the Merichem Division of Jefferson Lake Sulphur Company, the largest producer of cresylic acids in the United States. This publication states on its cover page that cresylic acid is the “common name for phenol, cresols, and xylenols.” However, in the operative parts of the publication, Merichem offers its phenolic compounds under the following designations: Products containing from 52% to 91% phenol are offered under the designation “phenol”; products containing from 51% to 98% orthocresol are offered under the designation “Ortho cresol,” and not cresylic acid, while products containing from 68% to 80% “meta-para cresols” are offered under the designation “meta-para cresols.” Also offered in this publication is “cresylic acid” of different types, all of which contain various mixtures of xylenols, phenols and cresols. Yet only one of these products (cresylic acid No. 86) contains even as much as 51% of a single isomer, orthocresol, while two other cresylic acids (Nos. 41 and 45) contain only 45% and 42% metacresol, respectively.
Another example is a 1971 chemicals price list (plaintiff’s exhibit 10) issued by Continental Oil Company, owner of Pitt-Consol Chemical Company. This price list offers under the heading “Cresylies . . . From Pitt-Consol * * * Cresols and Cresylic Acids” products designated as “Ortho-Cresol,” “Metapara Cresol,” “Xylenols” and “Cresylic Acids.” The constituents of the cresylic acids are not given, hut the two “xylenols” listed (2,6 xylenol and 2,4/2,5 xylenol) are stated to have a “typical purity” of 90.0% and 85.0% respectively.
It is to be observed that an earlier catalogue of Pitt-Consol entitled “High Purity Cresylies” (plaintiff’s exhibit 9) which was issued some time after 1949 also lists various grades of that company’s products, which are designated as “phenol,” “ortho cresol,” “meta para cresol,” “cresol” and “cresylic acid.” The specifications for the cresylic acids thus listed show varying specified combinations of cresols, xylenols and phenols. Significantly, only one of these, “cresylic acid No. 7,” contains as much as 45% of an individual isomer, i.e., metacresol.
In addition, the January 15, 1968 and May 6, 1968 editions of the Oil, Paint and Drug Reporter
m-Cresol, 95-98%;
m-p-Cresol, 95% and 97%;
o-Cresol, four grades, depending on melting point;
p-Cresol, 98%;
Cresylic acid, metapara content above 25%;
Cresylic acid, metapara content 25% or less;
Cresylic acid, importer, ADF [American Duty Free];
Xylenol, three grades, depending on melting point;
Xylenol fraction, dry above 227 degrees C.; and
Xylenol fraction, dry at or below 227 degrees C.
It also bears mention that the Custom House Guide (1959) in its alphabetical import commodity index lists “cresylic acid” and “xylenol” as separate dutiable commodities. Thus “cresylic acid” with 75% or more tar acids is listed at page 716 under the U.S. Department of Commerce commodity code number 8020.100, while “xylenol” is listed at page 968 under another commodity code number, 8040.985.
Beyond these considerations, it is not without significance that defendant’s witness Mr. Benjamin W. Jones, former vice president of sales at Pitt-Consol Chemical Company and, prior to that, chief chemist for Pittsburgh Coal Carbonization Company, testified that Pitt-Consol sold phenol of 82% and 90% purity as “82% phenol” and “90% phenol,” and that it was a general practice in the trade to describe products which were 80% to 90% in purity of a particular phenolic isomer by the name of that isomer and not as cresylic acid. (R. 351-52.) To similar effect, plaintiff's witness, Mr. Phinney, testified that “most often” if 2,4 xylenol had the characteristics in which a customer was interested, a product containing “88.1% of
I am persuaded from the foregoing that a clear distinction is drawn in the trade between “cresylic acid” and “xylenol” as articles of commerce; that a product containing a concentration of 88% or more of 2,4 xylenol is known and offered as “2,4 xylenol,” not as “cresylic acid”; and that this distinction is reflected in the tariff schedules in both subparts A and B of part 1 of schedule 4.
Thus, subpart A, which covers “Organic Chemical Crudes” and specifically names “all known coal-tar crudes and distillates containing 6-membered rings * * *,”
In subpart A, Congress obviously ascribed different meanings to the terms “cresylic acid” and “xylenols.” It is equally patent that when used in another related provision of the same schedule and part neither term undergoes a change in meaning. In other words, where the same word or phrase is used in different parts of the same statute, it will be presumed, in the absence of any clear indication of a contrary intent, to be used in the same sense throughout the statute. Schooler v. United States, 231 F.2d 560 (8th Cir. 1956); Acme Venetian Blind & Window Shade Corp. v. United States, 56 Cust. Ct. 563, C.D. 2704 (1966).
Therefore, the distinction made between cresylic acid and xylenol in the crude state in subpart A (by virtue of their separate provisions) carries over to those same articles when provided for as intermediates in subpart B. This holds true even though xylenol is not eo nomine provided for.
Furthermore, plaintiff’s claim that cresylic acid embraces highly concentrated phenolic isomers is vitiated by the classification system in subpart B, which provides separately for the high-boiling tar acids: phenol (item 403.40) and the cresols (item 403.44).
Accordingly, I find that the importations in issue, containing concentrations of 2,4 xylenol ranging from 88% to 90% are xylenol and not cresylic acid, as claimed. In the absence of an eo nomine provision for xylenols, their classification under item 403.46 as “Other” coal tar distillates must be sustained unless precluded therefrom because they are not distillates of coal tar.
On this latter aspect, it is uncontroverted that a product containing 2,4 xylenol of 88% to 90% purity cannot be isolated from coal tar by
Examination of subpart B and the governing headnote and subheading compels rejection of such a narrow view. The record establishes that metacresol of 75% purity cannot be obtained from coal tar by distillation alone but requires synthetic steps in its preparation. Thus, adoption of the construction tentatively raised by defendant would make a nullity of the provisions in item 403.44 for metacresol and paracresol.
I am also cognizant of the fact that headnote 1 of subpart B
* * * on the “benzenoid” concept and prevailing practice. Within this framework, it continues the existing relationships*153 with the crudes in subpart A, and extends the concept now extant in paragraph 27(a)(1) of providing for “benzenoid” products from whatever source obtained. * * *
[Emphasis added.]
For the foregoing reasons, it is concluded that the importations in issue were correctly classified by the government under item 403.46. Plaintiff’s claim must therefore be overruled and judgment will be entered accordingly.
The claimed duty rate under item 403.42 ranges, depending upon the entry date, Irom 1.550 per lb. + 9% ad val. to 1.2(5 per lb. + 7% ad val.
The assessed duty rate under item 403.46 ranges, depending upon the date of entry, from 30 per lb. +18% ad val. to 2.40 per lb. +14% ad val.
Defendant’s alternate claimed duty rate under item 403.60 ranges, depending upon the entry date, from 30 per lb. +22.5% ad val. to 20 per lb. +17.5% ad val. Since the rate of duty under defendant’s alternate claim is higher than that assessed in liquidation under item 403.46, defendant does not request reliquidation Under Rem 4O3.60-
Study, p. 2.
Ibid., p. 17.
The information contained in tins and the succeeding two paragraphs is obtained from the following authorities, in addition to the record: II Chemistry of Coal Utilization (1945); Faith, Keyes and Clark, Industrial Chemicals (2d ed. 1957); Snell and Snell, Chemicals of Commerce (2d ed. 1952); 4 Kirk and Othmor, Encyclopedia of Chemical Technology (1949); 1 Summaries of Tariff Information pt. 2 (1948).
It is to be added that distillation is a “process of evaporation and re-condensation used for separating liquids into various fractions according to their boiling points or boiling ranges.” Chambers’ Technical Dictionary 254 (rev. ed. 1949). Fractional distillation is the process of “collecting separately the distillates evaporating at certain temperatures.” Ilachh’s Chemical Dictionary 279 (4th ed. 1969).
An isomer is a compound composed of the same elements, the same chemical formula, and the same molecular weight as another compound or compounds, with the difference in the compounds being solely in the arrangement of the atoms in the molecule. Because of this difference in structural arrangement, the compounds will differ in one or more properties.
In this connection, Dr. Philip L. St otter, a chemist and assistant professor of chemistry, who was called as a government witness, testified without contradiction that he did not know of any distillation of coaltar which would give a 2,4 xylonol of 90% purity. (R. 526, 531--32.)
Plaintiff’s witness, Mr. Donald C. Phinnoy, a chemical engineer and vice president of the plaintiff company, testified (R. 188-89):
Prom the point of view, in my mind, cresylic acid is the name that describes a family or a chi>$ of compounds and therefore, any of the compounds that arc in that class retain the name, cresylic acid, whei lu r they aro ten per cont or one hundred per cent. Just like fruit. An orange is fruit whether you call it an orange or fruit. Xylonol is cresylic acid whether you call it either.
See, for example:
Bennett, Concise Chemical and Technical Dictionary 21)3 (3d ed. 1974):
cresylic acid. Mixture of o-, m-, and p-cresols (cresyl, paracresylol); * * •.
Industrial Chemicals, supra note 6, at p. 297:
Cresol (cresylic acid) is an isomeric mixture (o-, ra-, and p-cresol) obtained by refining the so-called tar acids. * * *
Ilackh’s Chemical Dictionary, supra note 6, at p. 183:
Cresylic acid. Mixed o-, ra-, and p-cresols.
3 McGraw Iiill Encyclopedia of Science and Technology 542 (1960):
Cresol. * * * Mixtures of the cresols (cresylic acid) are used in the manufacture of resins, plastics ** *,
Chemicals of Commerce, supra note 6, at p. 240:
* * * Mixed cresols, obtained in dark impure form from coal tar, are known as cresylic acid. * * *
See also, for example:
Rose and Rose, The Condensed Chemical Dictionary 319 (5th ed. 1956):
cresylic acid. (Sec also cresol.) The trade designation lor commercial mixtures of phenolic materials boiling above the cresol range. Cresylic acid consists of phenols, cresols, and xylenols in various proportions.
Concise Chemical and Technical Dictionary, supra note 10, at pp. 293-94:
cresylic acid, crudo. Crude mixture of monohydric phenols, essentially cresols and their higher homo-logs, of lower phenol content than crudo carbolic acid,
cresylic acid, refined. Refined mixture of monohydric phenols, consisting essentially of cresols and/or xylenols with or without a peicentage of phenol.
7 Encyclopedia Americana 159 (1953)*
* * * The crude tar acids are referred to as cresylic acids; they aie used in disinfectants, resins, metal cleaning compounds, or flotation agents, and oxidation inhibitors. The crude cresylic acids can be fractionated (usually under vacuum) into the individual tar acids, phenol, cresols, and xylenols. * * *
The terms “cresylic acid,” “cresylies,” and “tar acids” are also employed in a very broad general sense as a heading or lead caption on company brochures and price lists and in news articles to refer generally to phenolic compounds. However, in no wise are these terms identified with the specific products offered or referred to in such publications.
This publication is now known as the Chemical Marketing Reporter.
It is to be noted that plaintiff's witness, Mr. Phinney, testified that plaintiff has produced 3,5 xylenol o£ a purity as high as the merchandise at bar. However, while the three documents (defendant’s collective exhibit F) offered as evidence of a sale of such merchandise to the Ottawa Chemical Company in 1967 include the public weighmaster’s certificate which lists the commodity as “¿resylic acid,” the transmittal note accompanying the certificate prepared by plaintiff’s own plant personnel, notes the subject as: “Ottawa Chem - 3,5 xyl -12/8/67.” Further, while the bill of lading describes the article as “Cresylic acid (3/5 xyenol [sic]),” under the heading “Billing Information,” the “Product” is slated to be “3,5 xylenol.” In short, even plaintiff refers to a commodity having a 3,5 xylenol content of 88% or higher as “3,5 xylenol."
Study, p. 19.
The subheading covers—
All distillates of coal tar, blast-furnace tar, oil-gas tar, and water-gas tar, which on being subjected to distillation yield in the portion distilling below J90°C. a quantity of tar acids equal to or more than 5% by weight of the original distillate or which on being subjected to distillation yield in the portion distilling below 215°C. a quantity of tar acids equal to or more than 75% by weight of the original distillate.
The boiling points of metacresol and paracresol are so close together (202.8°C. and 201.8°C., respectively) it appears that paracresol of 75% purity could not be obtained by distillation either. See 4 Encyclopedia of Chemical Technology, supra note 6, which states, p. 602:
* * * Of the three cresols the ortho isomer is the only one directly recoverable from the still as a pure compound. The boiling points of m-cresol and p-cresol are too nearly alike to permit separation of these isomers by fractional distillation. Consequently, these two compounds are either used as mixtures or subjected to further treatment.
See also II Chemistry of Coal Utilization, supra noto 6, which states, pp. 1345-46:
o-Cvesol, as previously noted, is prepared by fractional distillation of crude tar acids to obtain a concentrate which is then refractionated to yield a product of the desired purity. Because of this comparative ease of preparation, o-crcsol was obtained from crude tar acids considerably sooner than the m- and p-cresols, which distill within a boiling range of about V/f. This necessitated the discovery of some other means of separation than distillation. Subsequent research has evolved a number of chemical separation schemes for m~ and p-cresol, but even at the present time these two compounds are still marketed almost entirely as a mixture.
And see Industrial Chemicals, supra note 6, at p. 298.
Headnote 1 provides that—
1. The provisions of items 403.02 to 403.60, inclusive, in this subpart shall apply not only to the products described therein when obtained, derived, or manufactured in whole or in part from products described in subpart A of this part, but shall also apply to products of like chemical composition having a benzenoid, quinoid, or modified benzenoid structure artificially produced by synthesis, whether or not obtained, derived, or manufactured in whole or in part from products described in said subpart A.
Study, p. 20.