In re Angstadt

537 F.2d 498, 190 U.S.P.Q. (BNA) 214, 1976 CCPA LEXIS 152
CourtCourt of Customs and Patent Appeals
DecidedJune 24, 1976
DocketPatent Appeal No. 75-560
StatusPublished
Cited by34 cases

This text of 537 F.2d 498 (In re Angstadt) is published on Counsel Stack Legal Research, covering Court of Customs and Patent Appeals primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

Bluebook
In re Angstadt, 537 F.2d 498, 190 U.S.P.Q. (BNA) 214, 1976 CCPA LEXIS 152 (ccpa 1976).

Opinions

BALDWIN, Judge.

This appeal is from the decision of the Patent and Trademark Office Board of Appeals affirming the rejection of claims 3-5, 12-22, and 27 in application serial No. 772,-421, filed October 31, 1968, for “Organometallic Complexes As Alkylaromatic Oxidation Catalysts.” We reverse.

The Invention

The claimed invention involves a method of catalytically oxidizing secondary or tertiary alkylaromatic hydrocarbons to form a reaction mixture comprising the corresponding hydroperoxides. The method employs as the catalyst an organometallic complex formed between hexaalkylphosphoramides and metal salts, the complex having the formula MX„(HAPA)m, wherein HAPA is a hexaalkylphosphoramide, MX is a metal salt, m is an integer of from 1 to 8, and n is an integer of from 1 to 4.

In summarizing their invention, appellants state in their specification:

[500]*500It has now been found, in accordance with the present invention, that organometallic complexes formed between metal salts, preferably those derived from transition metals, (including metals of the lanthanide and actinide series), and hexaalkylphosphoramides are effective catalysts in the oxidation of secondary and tertiary alkylaromatic hydrocarbons. Certain of these catalysts, and particularly those derived from metal salts of the lanthanide series, are especially effective in forming the hydroperoxides of the alkylaromtic[sic] hydrocarbons to the exclusion of other hydrocarbon oxidation products, thus providing the hydroperoxides in high yields at increased conversion rates.

The products produced by this process are described in appellants’ specification as follows:

[T]he oxidation products of the instant process are generally, alcohols, aldehydes, ketones, hydroperoxides, or mixtures thereof. Of these various products, maximization of the formation of the hydro-peroxides is generally preferred * * *. Accordingly, as a preferred embodiment of this invention, it has been discovered that certain of the various metals * * are particularly effective as catalysts in the preparation of hydroperoxides from secondary and tertiary alkylaromatic compounds * * *. These metals preferentially give yields of over 90 percent hydroperoxides to the exclusion of other oxidation products at conversion rates of at least about 4 percent per hour, and in many cases as high as 20 to 25 percent per hour. In the case of those remaining metals which yield lesser amounts or no hydroperoxides in the final product, while applicants do not wish to be bound by any particular theory, it is believed that they too yield hydroperoxides which are then rapidly decomposed by the catalyst complex to form aldehydes, ketones and the like. [Emphasis added.]

Claims 22 and 27 are illustrative and read as follows:

22. The process according to Claim 27 wherein the oxidation is carried out in the added presence of a hydroperoxide.
27. In the process for the catalytic oxidation of secondary or tertiary alkylaromatic hydrocarbons of the formula
wherein R is lower alkyl; Rj is lower alkyl or hydrogen; and Ar is an aromatic nucleus selected from the group consisting of phenyl and naphthyl, in the presence of air or oxygen at a temperature of from about 80 to 150 °C to form a reaction mixture comprising the corresponding hydroperoxides, the improvement wherein the catalyst is of the formula
MXn(HAPA)m
wherein HAPA is a hexaalkylphosphoramide, the alkyl moiety of which has from one to thirty carbon atoms; MX is metal salt wherein M is a transition metal cation of Group IB, IIB, IIIB, IVB, VB, VIB, VIIB, VIIIB or IIA of the Periodic Table and X is an inorganic anion of said metal salt; m is an integer of from 1 to 8; and n is an integer of from 1 to 4, wherein the ratio of said catalyst to said alkylaromatic hydrocarbon is from about 0.1 to 5.0 parts by weight of catalyst per 100 parts by weight of alkylaromatic hydrocarbon.

The Rejection

The examiner rejected all of the claims under 35 U.S.C. § 112, first and second paragraphs. However, the board’s rationale for affirming the rejection was directed primarily to the enablement requirement of the first paragraph of section 112. The board considered the question of “whether the claims on appeal read on subject matter as to which the specification is not enabling.” The claims and the specification were compared and it was found:

[501]*501[T]he claims call for the preparation of a reaction mixture comprising the hydro-peroxides, using the metal salt complexes as the catalyst. However, the specification states that not all of the complexes will produce hydroperoxides and neither discloses which of the complexes will not work nor gives any information as to how the operative catalysts might be determined, without undue experimentation. We believe that the specification leaves too much to conjecture, speculation and experimentation and is insufficient in law to support the present claims containing the disputed language. [Emphasis in original.]

In addition, the board specifically pointed to claim 22 as being “inconsistent with claim 27 in light of present Example 6, which indicates that the presence of added hydroperoxide results in a product devoid of the recited ‘corresponding hydroperoxides.’ ” The board went on to state that “insofar as this is a further ground of rejection under 35 USC 112, it is sustained.”

OPINION

Since all of the claims have been rejected under the first and second paragraphs of 35 U.S.C. § 112, we begin with the analysis set forth in In re Moore, 439 F.2d 1232, 1235, 58 CCPA 1042, 1046-47, 169 USPQ 236, 238 (1971):

Any analysis in this regard should begin with the determination of whether the claims satisfy the requirements of the second paragraph.

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537 F.2d 498, 190 U.S.P.Q. (BNA) 214, 1976 CCPA LEXIS 152, Counsel Stack Legal Research, https://law.counselstack.com/opinion/in-re-angstadt-ccpa-1976.