In re Mercier

515 F.2d 1161, 185 U.S.P.Q. (BNA) 774, 1975 CCPA LEXIS 156
CourtCourt of Customs and Patent Appeals
DecidedMay 15, 1975
DocketPatent Appeal No. 74-528
StatusPublished
Cited by14 cases

This text of 515 F.2d 1161 (In re Mercier) 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 Mercier, 515 F.2d 1161, 185 U.S.P.Q. (BNA) 774, 1975 CCPA LEXIS 156 (ccpa 1975).

Opinions

BALDWIN, Judge.

This appeal is from the decision of the Patent and Trademark Office Board of Appeals affirming the examiner’s rejection of all claims remaining in application serial No. 708,775, filed February 28, 1968, entitled “Process for Splitting Ace-tals and Hemi-Acetals.” We reverse.

The Invention

Appellant’s invention relates to a process for “splitting” acetals and hemi-ace-[1163]*1163tais by - either hydrolysis or alcoholysis reactions. The alcoholysis of acetals or hemi-acetals by means of alcohols results in the formation of acetals having alcohol radicals different from those on the original material. The hydrolysis reaction of acetals or hemi-acetals with water results in the formation of the corresponding aldehydes.

Appellant’s specification describes the reactions of the invention as follows:

These reactions can be illustrated by the following equations in which R, R' and R" can be organic radicals which are the same or different hydrocarbon radicals which may be straight or branched-chain alkyl radicals having from 1 to 12 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, isoamyl, hexyl, 2-ethyl butyl, heptyl, octyl, isooctyl, 2-ethyl hexyl, nonyl, isononyl, decyl and dode-cyl; alkenyl radicals having from 3 to 12 atoms, such as propenyl, butenyl, hexenyl and allyl, the olefinic linkage of the alkenyl radicals being not in a, |3; alicyclic radicals, such as cyclohexyl and methyl cyclohexyl; and aralkyl radicals, such as benzyl. R can also be hydrogen or an aromatic radical, such as phenyl, tolyl and xylyl, the aromatic radical having only one nucleus, the nucleus bearing no more than two al-kyl substitutents, and the total amount of carbon atoms of the alkyl substitu-ents, if any, being from 1 to 5.
Hydrolysis:
R-CH(0R')2 + H20-►R-CHO + 2 R'OH
Alcoholysis:
R-CH(0R')2 + 2 R"0H-►R — CH(0R")2 + 2 R'OH

The prior art processes for accomplishing the above-referred to reactions are apparently subject to some difficulties. For example, the removal of one or both of the OR' groups on the acetal may have a tendency to cause polymerization into what the specification refers to as “complex compounds of varying and not accurately defined polymerization degree.” The removal of an OR' group apparently can also lead to the formation of undesired highly volatile and explosive ethers. Additionally, use in many of the prior art processes of a strong inorganic acid such as sulfuric acid to catalyze the splitting reaction causes corrosion problems and provides a product which is difficult to separate from the catalyst.

Appellant’s process for “splitting” ace-tals and hemi-acetals is accomplished by passing a homogeneous liquid phase containing the reactant upwardly through a bed of suspended catalyst particles in the form of a sulfonic ion-exchange resin in the acid form.

The specification sets forth the processing details by which the process may be carried out as follows:

Continuous operation may, for example, be performed by passing the liquid reactants heated to reaction temperature through a reaction zone containing a catalyst and maintained under the pressure required for maintaining the reaction medium or mixture in a liquid state at the operating temperature. One may advantageously employ, inter alia, an inverted cone-shaped reactor through which the reaction medium or mixture flows in an upward direction thereby to maintain the finely divided catalyst in a dispersed or suspended state or in a fluidized state through the liquid phase. [Emphasis added.]

The language of the claims defines the invention in much the same manner as the specification, except that the sulfonic ion exchange catalyst is referred to as a “fluidized catalyst” instead of a catalyst in a “dispersed or suspended state or in a fluidized state through the liquid phase.” Claim 16 is representative:

16. A process for splitting acetals and hemi-acetals which comprises passing a homogeneous liquid reaction mixture comprising a compound selected from the group consisting of an acetal having the formula:
R-CH(OR')2
[1164]*1164and a hemiacetal having the formula:
R-CH(OH) (OR')
wherein R is selected from the group consisting of hydrogen and a hydrocarbon group containing 1 — 12 carbon atoms and R' is a hydrocarbon group containing 1-12 carbon atoms and a material selected from the group consisting of water and a mixture of alka-nol and water, wherein the water constitutes between 5-30% by weight of the reaction mixture, upwardly through a fluidized catalyst, said catalyst being a sulfonic ion exchange resin in acid form, at a temperature of 60° to 140° C. and a pressure sufficient to maintain the reaction mixture in the liquid phase.

The Prior Art Rejection

The following references were relied on:

Enk et al. (Enk) 3,317,593 May 2,, 1967 Alheritiere et al.
(Alheritiere) 2,980,731 April 18, 1961

The board cited the following as “[gjeneral references of which we take judicial notice”:

Webster’s Third New International Dictionary, Unabridged, p. 877 (1963).
Kirk-Othmer, Encyclopedia of Chemical Technology, Second Edition, Vol. 9, pp. 398, 399 (1966).
The Condensed Chemical Dictionary, 7th Ed., p. 423 (1966).
Hackh’s Chemical Dictionary, 4th Ed., p. 273 (1969).
Perry’s Chemical Engineers’ Handbook, 4th Ed., § 20, pp. 42-52, particularly, p. 50 (1963).

The appealed claims were rejected by the examiner over Enk in view of Alher-itiere under the provisions of 35 U.S.C. § 103. Enk teaches a process for the hydrolysis of alkanol derivatives, such as acetals, by means of water in the presence of a static acid exchange catalyst. His specification states:

It is known to crack hydrolyzable organic oxygen compounds such as, for example, esters, acetals or ketals, in the presence of acid catalysts, like mineral acids or cation exchangers, with water, into alcohol and the appropriate organic residue. In all cases the reaction can be carried out only up to the hydrolysis equilibrium. The hy-drolysate in equilibrium, consisting of the starting substance, water, alcohol and a second cracking product which, depending upon the starting substance, is an acid, an aldehyde or a ketone, is then separated into its components.

Alheritiere discloses a process in which a solid catalyst is suspended in an upwardly flowing liquid reaction mixture. The catalyst is thus suspended in a turbulent state in the liquid permitting more efficient mass and heat transfer rates and facilitating reactions involving heterogeneous liquid mixtures. Alheriti-ere teaches generally that hydrolysis reactions using'an ion exchange resin catalyst may be advantageously accomplished by means of his process, but he nowhere specifically discloses the hydrolysis of either acetals or hemi-acetals.

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515 F.2d 1161, 185 U.S.P.Q. (BNA) 774, 1975 CCPA LEXIS 156, Counsel Stack Legal Research, https://law.counselstack.com/opinion/in-re-mercier-ccpa-1975.