MATTER OF APPLICATION OF MEYER

• Citation: 599 F.2d 1026
• Decision Date: 07 June 1979
• Docket Number: Appeal No. 79-505.
• Court: United States Court of Customs and Patent Appeals
• Parties: In the Matter of the Application of Horst MEYER.

599 F.2d 1026

In the Matter of the Application of Horst MEYER.

Appeal No. 79-505.

United States Court of Customs and Patent Appeals.

June 7, 1979.

Bruce M. Collins, New York City (Jacobs & Jacobs, P. C., New York City), attorneys of record, for appellant.

Joseph F. Nakamura, Washington D. C., for the Commissioner of Patents; Jack E. Armore, Washington D. C., of counsel.

Before MARKEY, Chief Judge, and RICH, BALDWIN, MILLER and NEWMAN,^* Judges.

NEWMAN, Judge.

This is an appeal from the decision of the Patent and Trademark Office (PTO) Board of Appeals (board) sustaining the examiner's rejection of claims 2-6, and 9-12, of application serial No. 557,296, filed 11 March 1975, for "Process for the Preparation of 2-Nitrobenzaldehyde and Intermediates Therefor." We reverse.

Background

The Invention

The compound, 2-nitrobenzaldehyde, has been known for more than 80 years. It can be used, inter alia, as an intermediate in the production of the pharmaceutically active 4-nitrophenyl-1, 4-dihydropyridine derivatives. Appellant's invention resides in an industrially satisfactory process for the production of 2-nitrobenzaldehyde. Specifically, an alkali metal salt of a 2-nitrophenylpyruvic acid is reacted with an aqueous solution of an alkali metal hypochlorite to yield 2-nitrobenzylidene chloride, which compound is then subjected to aqueous hydrolysis at a temperature of from about 20°C to about 150°C to produce 2-nitrobenzaldehyde. Using sodium as the alkali metal, the process can be diagrammatically depicted as follows:

Advantageously, the 2-nitrophenylpyruvic acid can be prepared by treating 2-nitrotoluene with a diester of oxalic acid¹ and then using it directly without isolation. Claim 11 is illustrative of the appealed claims:

11. The process for the preparation of 2-nitrobenzaldehyde which comprises treating an alkali metal salt of the corresponding 2-nitrophenylpyruvic acid with an alkali metal hypochlorite in an aqueous medium to yield the corresponding 2-nitrobenzylidene chloride and subjecting said 2-nitrobenzylidene chloride to aqueous hydrolysis at a temperature of from about 20° to about 150° C.

Among the advantages of appellant's invention is that the starting materials, the 2-nitrotoluenes and oxalic acid diesters, are readily accessible in adequate quantity, and the end product is obtained from the hydrolysis in high yield and high purity.

Prior Art

Reissert,² the most pertinent reference of record, discloses, inter alia, the oxidation of 2-nitrophenylpyruvic acid using various oxidizing agents. The oxidation is generally described as follows:

Upon the oxidation, which was studied very carefully and under a large number of different conditions in particular on the o-nitrophenyl pyruvic acid, the side chain is broken apart at one of the two places indicated by dashed lines in the following diagram

and either o-nitrophenyl acetic acid is produced or o-nitrobenzoic acid or o-nitrobenzaldehyde.³ Upon oxidation by alkaline chlorine or bromine solution, halogen-containing products are furthermore formed.

Subsequent to this general description, Reissert describes specific oxidation experiments. These include, inter alia, oxidation experiment (d) which uses an alkaline bromine solution, specifically sodium hypobromite, and oxidation experiment (e) which uses calcium hypochlorite.⁴ Use of sodium hypobromite resulted in the production of 2-nitrobenzylidene bromide, which compound was treated with sodium carbonate to remove the bromine, and then treated with phenylhydrazine acetate to yield 2-nitrobenzaldehyde phenyl hydrazone.⁵ Use of calcium hypochlorite resulted in an unexamined chlorine-containing oil together with a crystalline substance of the formula C16H12N2O6.

Cassebaum⁶ reviews various existing methods for the production of 2-nitrobenzaldehyde, none of which need be discussed here, and concludes that they are unsatisfactory. The author notes that even though the compound has been known for more than 80 years, the literature still fails to describe any advantageous method of producing it. Cassebaum then describes the method which he developed which comprises oxidizing 2-nitrophenylnitromethane with KMnO4 to produce 2-nitrobenzaldehyde.

Clarens⁷ discusses the conversion of hypochlorites and hypobromites to chlorates and bromates, respectively. No further discussion of this reference is deemed necessary since its relevance is tenuous, at best.

Feiser et al.,⁸ the last of the references relied upon by the examiner, describes various reactions using sodium hypobromite and sodium hypochlorite, none of which involve the production of 2-nitrobenzaldehyde. As with Clarens, we see no need to further discuss this reference.

Rebuttal Evidence

A declaration was submitted by the inventor, Meyer, comparing the yield obtained by Reissert with that of the claimed process. By reacting 2-nitrophenylpyruvic acid with sodium hypobromite, Reissert's yield of 2-nitrobenzylidene bromide, based upon the acid employed, was 35.4%. Assuming 100% conversion, the maximum yield of 2-nitrobenzaldehyde would only be 35.4%. Repeating Reissert's work, Meyer was unable to obtain a yield of more than about 18% of 2-nitrobenzylidene bromide.

In contradistinction to Reissert's use of sodium hypobromite, when sodium hypochlorite is used according to the claimed process, the yield of 2-nitrobenzylidene chloride, based upon the acid employed, is 64.3%.

Proceedings Below

In the examiner's answer, all the appealed claims were rejected under 35 U.S.C. § 103 over Reissert taken in view of Cassebaum, Clarens, and Feiser et al. According to the examiner, Reissert discloses the use of an alkali metal hypobromite and equates the hypobromite and hypochlorite.⁹ Accordingly, "the Reissert reference by itself is deemed to teach every aspect of the claimed process and therefore the claimed process . . . would have been, at the very least, . . . obvious over Reissert." Cassebaum, Clarens, and Feiser et al. were relied upon as further evidence that it would have been obvious to use an alkali metal hypochlorite in place of the alkali metal hypobromite of Reissert.

With respect to appellant's uncontested evidence of unexpectedly improved yields with the alkali metal hypochlorite over the alkali metal hypobromite, the examiner dismissed it as "not persuasive of patentability."

The board affirmed the examiner. According to the board, it is "fairly well agreed that the difference in yields produced by the hypochlorite solution is significant and not readily explainable from the reference disclosures." With this in mind, the board phrased the issue to be decided as follows:

As observed by the examiner, the Reissert reference, by itself, teaches every aspect of the claimed process. Consequently, if Reissert constitutes an anticipation, 35 U.S.C. § 102(b), of the claimed subject matter, such rejection cannot be avoided by a showing under 37 C.F.R. 1.132. On the other hand, if the cited art merely renders the claimed process prima facie obvious, the showing of record would adequately rebut the inference of obviousness raised by the cited art. Emphasis in original.

The board concluded that Reissert anticipated the claimed invention, within the meaning of 35 U.S.C. § 102(b), since Reissert's reference to "alkaline chlorine or bromine solution" must be construed to mean alkali solutions of chlorine or bromine.

While the board apparently recognized that the examiner never mentioned 35 U.S.C. § 102, it, nonetheless, anomalously concluded that a new ground of rejection was not being made since "anticipation is the epitome of obviousness."

In a request for reconsideration, appellant argued that the board denied it procedural due process inasmuch as the board, in effect, entered a new ground of rejection (under 35 U.S.C. § 102(b)) while not affording appellant the procedural options provided for in 37 CFR 1.196(b).¹⁰ In addition, appellant submitted an affidavit by Willaim Bertsche, the individual who prepared the translation of Reissert upon which the board relied. According to Bertsche, the German word actually used by Reissert, "alkalische," is an adjective and means alkaline or basic, referring to an alkaline condition capable of turning red litmus paper blue, and it cannot be translated to mean the noun, "alkali," as suggested by the board.¹¹

In its decision on reconsideration, the board considered the newly submitted Bertsche affidavit even though it repeated its assertion that it had not made a new ground of rejection. While not expressly disavowing its prior construction of Reissert, the board did not repeat its prior statement that Reissert's reference to "alkalische" must be construed to mean "alkali." Instead, the board advanced a new theory for construing Reissert. Since Reissert's oxidation experiment (d) using sodium hypobromite is entitled "d) With alkaline bromine solution," and since this language is identical to Reissert's prior reference to "alkaline chlorine or bromine solution," Reissert must have had in mind the specific alkaline bromine solution of oxidation experiment (d) when he equated "alkaline bromine or chlorine solution." Thus, in the light of this new theory, the board repeated its conclusion that Reissert anticipated the claimed subject matter.

OPINION

We will initially dispose of the examiner's rejection based on 35 U.S.C. § 103 since the board did not expressly reverse it. See In re Pritchard, 463 F.2d 1359, 59 CCPA 1284, 1292, 1365, 175 USPQ 17, 22 (1972). The Meyer declaration, which is undisputed, indicates that when Reissert's sodium hypobromite is used the yield of 2-nitrobenzylidene bromide was 35.4% (based on the acid employed). In contradistinction, when the claimed sodium hypochlorite is used the yield of 2-nitrobenzylidene chloride was 64.3%.¹² As the board correctly recognized, "if the cited art merely renders the claimed process prima facie obvious, the showing of record would adequately rebut the...