Ex Parte Krafft et alDownload PDFPatent Trial and Appeal BoardJan 13, 201712502342 (P.T.A.B. Jan. 13, 2017) Copy Citation United States Patent and Trademark Office UNITED STATES DEPARTMENT OF COMMERCE United States Patent and Trademark Office Address: COMMISSIONER FOR PATENTS P.O.Box 1450 Alexandria, Virginia 22313-1450 www.uspto.gov APPLICATION NO. FILING DATE FIRST NAMED INVENTOR ATTORNEY DOCKET NO. CONFIRMATION NO. 12/502,342 07/14/2009 Philippe KRAFFT 345445US0DIV 6056 22850 7590 01/18/2017 OBLON, MCCLELLAND, MAIER & NEUSTADT, L.L.P. 1940 DUKE STREET ALEXANDRIA, VA 22314 EXAMINER KEYS, ROSALYND ANN ART UNIT PAPER NUMBER 1671 NOTIFICATION DATE DELIVERY MODE 01/18/2017 ELECTRONIC Please find below and/or attached an Office communication concerning this application or proceeding. The time period for reply, if any, is set in the attached communication. Notice of the Office communication was sent electronically on above-indicated "Notification Date" to the following e-mail address(es): patentdocket @ oblon. com oblonpat @ oblon. com ahudgens@oblon.com PTOL-90A (Rev. 04/07) UNITED STATES PATENT AND TRADEMARK OFFICE BEFORE THE PATENT TRIAL AND APPEAL BOARD Ex parte PHILIPPE KRAFFT, PATRICK GILBEAU, BENOIT GOSSELIN, and SARA CLAESSENS1 Appeal 2014-008426 Application 12/502,342 Technology Center 1600 Before ULRIKE W. JENKS, KIMBERLY McGRAW, and KRISTI L. R. SAWERT, Administrative Patent Judges. JENKS, Administrative Patent Judge. DECISION ON APPEAL This is an appeal under 35 U.S.C. § 134(a) involving claims directed to a method of producing dichloropropanol. The Examiner rejects the claims as obvious. We have jurisdiction under 35 U.S.C. § 6(b). We AFFIRM. 1 According to Appellants, the Real Party in Interest is SOLVAY (SOCIETE ANONYME). (App. Br. 1.) Appeal 2014-008426 Application 12/502,342 STATEMENT OF THE CASE Claims 1 and 8—20 are on appeal and can be found in the Claims Appendix of the Appeal Brief. Claim 1 is representative of the claims on appeal, and reads as follows: 1. A process for producing dichloropropanol, wherein glycerol is reacted with at least one chlorinating agent in a reactor made of or coated with enameled steel, the chlorinating agent comprises substantially anhydrous hydrogen chloride or is an aqueous solution of hydrogen chloride with a hydrogen chloride content higher than or equal to 4 % by weight, and a carboxylic acid, a carboxylic acid anhydride, a carboxylic acid chloride, a carboxylic acid salt or a carboxylic acid ester is present in the reaction as a catalyst. (App. Br. Claims Appendix) Appellants seek review of the Examiner’s rejection of claims 1 and 8— 20 under 35 U.S.C. § 103(a) as unpatentable over Britton2 in view of Steen3 and Smidt,4 and further in view of C. F. Boehringer,5 Griesheim-Elektron,6 Solvay,7 Jakobson,8 and Wang.9 The issue is: Does the preponderance of evidence of record support the Examiner’s conclusion that the combination of references renders 2 Britton et al., US 2,144,612, issued Sept. 10, 1936 (“Britton”). 3 Van den Steen et al., US 3,406,007, issued Oct. 15, 1968 (“Steen”). 4 Smidt et al., US 3,131,226, issued Apr. 24, 1964 (“Smidt”). 5 Boehringer et al., DE197308, published Apr. 16, 1908 (“Boehringer”). 6 Griesheim-Elektron, DE238341, published Sep. 19, 1911 (“Griesheim- Elektron”). 7 Solvay & Cie, GB 799,567, published Apr. 30, 1956 (“Solvay”). 8 Jakobson & Siemanowski, US 4,960,953 issued Oct. 2, 1990 (“Jakobson”). 9 Wang et al. US 4,499,255, issued Feb. 12, 1985 (“Wang”). 2 Appeal 2014-008426 Application 12/502,342 obvious the use of “a reactor made of or coated with enameled steel” in the production of dichloropropanol as claimed? Findings of Fact We adopt the Examiner’s findings of fact and reasoning regarding the scope and content of the prior art as set out in the Answer mailed July 17, 2014 and Final Action mailed Jan. 14, 2014. For emphasis only we highlight the following: FF1. Britton teaches that it was known to react glycerol with hydrogen chloride in the presence of a suitable catalyst such as acetic acid to form glycerol dichlorohydrin and two molecules of water, the known processes either allow the water of reaction to accumulate, favoring equilibrium conditions long before complete reaction can be obtained, or drive the water out of the reaction mixture by conducting the reaction at elevated temperatures, i. e., approximately 120° C. or higher. (Britton col. 1,11. 4—13.) FF2. Glycerol dichlorohydrin is also known as dichloropropanol (see Final Act. 5). FF3. Britton teaches including “an inert, water immiscible organic solvent in which the dichlorohydrin product is soluble” in the organic solvent mixture. (Britton col. 1,11. 30—35.) FF4. Britton teaches that “[i]n carrying out the reaction, glycerol and the solvent are mixed together in a suitable reaction vessel, together with a catalyst such as formic or acetic acid, and hydrogen chloride reacted therewith at temperatures varying with the particular solvent employed, to produce glycerol dichlorohydrin and water.” (Britton col. 1,11. 48-54.) 3 Appeal 2014-008426 Application 12/502,342 FF5. Britton teaches continuous distillation of the reaction mixture. This distillate, hence forth termed the “acid fraction”, on standing forms two layers, one comprising the organic solvent and the other the aqueous hydrochloric acid. The organic solvent layer may be separated therefrom in any convenient manner and returned to the reaction zone, and serves as an extractant to, remove the greater portion of the dichlorohydrin product from the aqueous hydrochloric acid solution, which tends to dissolve the same. (Britton col. 2,11. 15—24.) FF6. The Examiner finds that Britton “do[es] not disclose any details of the vessel used to carry out their reaction.” (Final Act. 6.) FF7. Steen discloses a process for producing molybdenum trioxide in a reactor vessel using a hydrochloric gas reaction. The process “comprises the steps of contacting a solid bed of material containing molybdenum in an hexavalent oxidized form with a recycling gaseous stream consisting essentially of hydrogen chloride at a temperature between about 150° C. and 500° C.” (Steen col. 9,11. 1—5.) FF8. Steen discloses that many different types of reactors can be employed to carry out the reaction (see Steen col. 4,11. 2—14). The reactor can be made of any materials resistant to gaseous hydrochloric acid and oxidation at the above stated temperatures; for example, nickel and nickel alloys, special steels, or various ceramic materials (bricks or quartz for example), ordinary enamelled steel may be used, or glasses which have a high softening point such as Vycor and Pyrex (trademarks). (Steen col. 4,11. 15-21). FF9. Smidt discloses a process for the production of carbonyl compounds. Smidt explains that the process 4 Appeal 2014-008426 Application 12/502,342 can be carried out in all apparatus suited for the conversion of gases with solid catalysts such as for example, tube system or fluidized bed reactor. Of course care must be taken that the parts of the apparatus which come into contact with the catalyst are corrosion resistant. Suitable corrosion resistant materials, for example, are enamel, glass, porcelain, stone ware, synthetic resins, rubber, titanium, tantalum, Hastelloy and the like. (Smidt col. 4,1. 73 to col. 5,1. 6.) Principle of Law “If the claim extends to what is obvious, it is invalid under § 103.” KSRInt’l Co. v. Teleflex Inc., 550 U.S. 398, 419 (2007). “Where a skilled artisan merely pursues ‘known options’ from ‘a finite number of identified, predictable solutions,’ the resulting invention is obvious under Section 103.” In re Cyclobenzaprine Hydrochloride Extended-Release Capsule Patent Litig., 676 F.3d 1063, 1070 (Fed. Cir. 2012) (quoting KSR, 550 U.S. at 421). Analysis The Examiner finds that Britton discloses “a process for preparing glycerol dichlorohydrin (dichloropropanol) comprising reacting glycerol with hydrogen chloride (chlorinating agent)” (Final Act. 5; Ans. 2; FF1— FF4.) The Examiner recognizes that “Britton et al. differ from the claimed invention in that Britton et al. do[es] not disclose any details of the vessel used to carry out their reaction. However, since Britton et al. use hydrogen chloride/hydrochloric acid in their reaction the skilled artisan would be motivated to use a vessel that is resistant to corrosive materials” (Final Act. 6; FF1—FF4). The Examiner concludes that because “hydrogen chloride/hydrochloric acid is known to be corrosive[, t]he skilled artisan 5 Appeal 2014-008426 Application 12/502,342 would have been motivated to use corrosive resistant materials in order to avoid contamination of the desired product” (Final Act. 6). “[A] person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense. In that instance the fact that a combination was obvious to try might show that it was obvious under § 103.” KSR, 550 U.S. at 421. Britton discloses the production of glycerol dichlorohydrin (a.k.a. dichloropropanol) using a suitable reaction vessel (FF1—FF4). Because Britton is silent with respect to the reaction vessel itself the Examiner reasonably turned to other references that also use hydrogen chloride gas in the reaction process (FF7—FF9). Steen and Smidt each teach several suitable reaction vessels that can be used in chemical reactions utilizing hydrogen chloride gas in the process (FF8 & FF9). A skilled artisan would have reasonably expected success in carrying out Britton’s process in an enameled steel reaction vessel, a corrosion-resistant material, as disclosed in Steen or Smidt would. The Examiner further articulated that because hydrochloric acid is a known corrosive “[t]he skilled artisan would have been motivated to use corrosive resistant materials in order to avoid contamination of the desired product” (Ans. 4). Steen discloses that each of the disclosed reactors are made of materials resistant to gaseous hydrochloric acid (FF7 & FF8). In other words, Steen discloses multiple materials that are suitable in carrying out reactions using hydrogen chloride gas, and any one of the reactors made with the materials disclosed in Steen would have been obvious to use in 6 Appeal 2014-008426 Application 12/502,342 Britton’s reaction. Accordingly, we agree with the Examiner’s position that the combination of references renders claim 1 obvious. Selecting a suitable reaction vessel from the list of materials disclosed in Steen and Smidt would have been obvious because each of the materials is suitable to carry out a reaction requiring hydrogen chloride gas (FF8 & FF9). The selection of a known material based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327 (1945). Because any one of the materials disclosed in Steen and Smidt is taught as suitable for hydrochloric gas processing this renders each of the vessels equally obvious for use in the Britton’s process and thereby sufficiently supports a finding of obviousness. Furthermore, as the list in Steen and Smidt is small, the ordinary artisan would have readily recognized enameled steel as one of the suitable materials for use in a reaction vessel that is exposed to hydrogen chloride gas in the reaction process. We have reviewed Appellants’ contention that the Examiner erred in rejecting the claims as obvious. We are not persuaded and adopt the Examiner’s findings of fact and reasoning regarding the scope and content of the prior art as set out in the Answer and Final Office Action, and agree that claim 1 would have been obvious over the combination of Britton, Steen, and Smidt in addition to the other listed references. We address Appellants’ arguments below. Appellants contend that “under the conditions in Britton et ah such corrosion would not be expected to be a problem.” (Reply Br. 2; see App. Br. 8 (“HC1 gas is not corrosive at the temperatures used in [Britton et al]” 7 Appeal 2014-008426 Application 12/502,342 citing the Gilbeau Declaration10 in support).) “[I]t is not disputed that the solvent used in Britton et al is in contact with water which forms by reaction of glycerol with HC1, which is included in aqueous HC1 or which is distilled off. . . . Such disclosure by no means suggests that a water-HCl mixture exists in the vessel, given Britton et al’s disclosure that the water of reaction is removed substantially as formed.” (App. Br. 11.) In other words, Appellants contend that because the reaction temperatures in Britton are such that corrosiveness of HC1 gas is not an issue and water is removed from the reaction chamber, one would not look to other references for finding vessels that resist corrosion (see App. Br. 9). We are not persuaded. As recognized by both Appellants and the Examiner, Britton does not disclose any particularities with respect to the reaction vessel, stating simply that any suitable reaction vessel would suffice (FF4 & FF6; see App. Br. 4 (“Britton et al discloses using ‘a suitable reaction vessel’”)). Because there are no details with respect to the reaction vessel, it would have been reasonable for an ordinary artisan to consult other references that similarly disclose reaction procedures using hydrogen chloride gas, as the Examiner has done here (FF7 & FF8). The Examiner further reasoned that one of ordinary skill in the art would have been motivated to look to reactor vessels that are corrosion resistant because one of the byproducts of Britton’s reaction is the production of hydrochloric acid (see Ans. 4). 10 Declaration under 35 U.S.C. § 1.1.32 by Patrick Gilbeau, signed Nov. 7, 2013. 8 Appeal 2014-008426 Application 12/502,342 We are also not persuaded by Appellants’ contention that there is no suggestion that water-HCl mixture exists in the reaction vessel (see App. Br. 11). As explained by the Examiner, if water is not present in the reaction mixture of Britton then why does Britton teach employing solvents that are able to withstand hydrolysis during the reaction and distilling steps. . . . This disclosure implies that water is expected to be present during the reaction and distillation steps. In fact, Britton teaches that water forms in the reaction mixture. . . . The presence of this water along with hydrogen chloride [gas] forms hydrochloric acid, which is present in the reaction vessel prior to being distilled out portionally. . . . Thus, the vessel walls of Britton are subject to hydrochloric acid exposure. (Ans. 8.) Britton explains that the distillate, in other words the product that is removed from the reaction chamber, contains both aqueous hydrochloric acid and organic solvent (FF5). This disclosure in Britton provides sufficient evidence to support the Examiner’s position that hydrochloric acid is present in the reaction chamber at least for some period of time even if it is periodically or continuously removed because it would be expected that some water is always present as more dichloropropanol is formed during the reaction process. Appellants point to the Gilbeau Declaration as evidencing that not all the reaction vessels disclosed in Steen would be considered resistant to aqueous hydrogen chloride. Appellants assert that this undermines the Office’s position that any one of the reaction vessels in Steen would be suitable reaction vessel in Britton (App. Br. 9; see Gilbeau Dec. 1 8 (some metals “surprisingly do not in fact resist a reaction medium made of organic compounds and chlorinating agent contradict the statement that ‘all of the known corrosion resistant materials would be expected to be suitable for the 9 Appeal 2014-008426 Application 12/502,342 reaction of Britton’ and show that unique and surprising properties are provided by enameled steel”)). Specifically, the “results of resistance tests showing that several alloys and metals which show low corrosion rates in boiling - 1-1.5 % HC1 aqueous solution (Monel 400, a Ni-Cu alloy; Hastelloy C 276, a Ni-Cr-Mo alloy; Alloy 33, a Fe-Cr-Ni-Mo alloy; Titanium grade 2, unalloyed titanium; Titanium grade 26, a Ti-Ru alloy and Duplex SAF 2507, a Fe-Cr-Ni-Mo alloy).” (Gilbeau Dec. 1 8.) We recognize, but are not persuaded by, the resistance testing as shown in the Gilbeau Declaration. The Examiner explains that “the materials used in the comparisons of Gilbeau are not known to be materials which are as resistant to hydrochloric acid as those disclosed by Steen and Smidt.” (Ans. 12). The Examiner notes that based on what is known about hydrochloric acid “the results shown by Gilbeau are not unexpected” {id. at 15). We agree with the Examiner’s position that “aqueous hydrochloric acid attacks most metals and that the rate of reaction depends on acid concentration” (Ans. 12; see Kirth-Othermer-2, 18 (“[m]ost metals react with aqueous HC1. . . . Tantalum and zirconium exhibit the highest corrosion resistance to HC1”)). The art also recognizes that ceramic and glass materials as being resistant to hydrochloric acid as evidenced by Kirk- Othemer-2. “Glass and ceramic-coated equipment is widely used for handling hydrochloric acid. The glass lining is normally 0.5-1.0mm (20-40 mil) thick and can be applied to various base metals” (Kirth-Othermer-2, 19). Even if some of the suggested reactor materials disclosed in Steen and Smidt are not resistant to hydrochloric acid under the conditions tested in the Gilbeau Declaration or under the conditions used in Britton’s reaction, some of materials disclosed in Steen are in fact resistant, such as the enameled 10 Appeal 2014-008426 Application 12/502,342 steel vessel, as well as the glass and ceramic vessels taught by Steen and Smidt (FF8 & FF9). O ’Farrell states that “[ojbviousness does not require absolute predictability of success. ... all that is required is a reasonable expectation of success.” In re O’Farrell, 853 F.2d 894, 903 (Fed. Cir. 1988). Here, the Examiner has sufficiently articulated a reason why in the absence of any disclosure about the reaction vessel in Britton, one of ordinary skill in the art would have looked to other references such as Steen and Smidt to find materials that are suitable for carrying out reactions with hydrogen chloride gas and a skilled artisan would have reasonably expected that selecting enameled steel, a corrosion-resistant material, for use in Britton would have been successful (see Ans. 2-4). Whether or not some of the materials disclosed in Steen and Smidt are indeed upon further testing found not to be as resistant to degradation by hydrogen chloride as initially thought and disclosed in the references, such observation does not detract from the reasonableness of the Examiner’s obviousness rejection as articulated in the rejection. On balance, the totality of the evidence presented favors a finding of obviousness. Furthermore, just because some of the materials tested in the Gilbeau Declaration are somewhat reactive with hydrochloric acid does not mean that reactors made of those materials are not suitable for carrying out Britton’s reaction with a reasonable expectation of producing dichloropropanol. It is important to note that the claims do not recite any limitation with respect to reactivity to the reactor material. There is insufficient evidence on this record to establish that the use of an enameled steel reactor in producing dichloropropanol provides some unexpected 11 Appeal 2014-008426 Application 12/502,342 benefit other than resistance to hydrochloric acid which was already known and recognized in the references. Accordingly, for the reasons discussed, we are not persuaded that the Examiner failed to make out a prima facie case of obviousness. We are also not persuaded that the evidence advanced by Appellants shows any unexpected results that outweighs the evidence of prima facie obviousness. We affirm the rejection of claim 1 under 35 U.S.C. § 103(a) as being obvious. As claims 8, 10—14, and 18—20 have not been argued separately, they fall together with claim 1. 37 C.F.R. § 41.37(c)(l)(iv). Claim 9 Appellants contend because Britton’s “process continuously removes water from the reaction zone would lead one of ordinary skill in the art to avoid adding the extra water of associated with aqueous HC1” into the reaction chamber (App. Br. 12). We are not persuaded. As explained by the Examiner, “Britton places not [sic] limits on the water content. . . and 4% or higher reads upon the amounts disclosed in the examples of Britton” (Ans. 15.) Additionally, we note that as long as the hydrogen chloride gas, glycerol and catalyst are present, more water would accumulate as the reaction proceeds. Claim 15 & 16 Appellants contend that Britton “neither discloses or suggests relating a residence time to a ratio of the volume of liquid medium in the reactor to the flow rate by volume of reactants” (App. Br. 13). Appellants contend that Britton “neither discloses or suggests relating a residence time to a ratio of the volume of liquid medium in the reactor to the flow rate by volume of glycerol, let alone the residence time of this claim” (App. Br. 13). 12 Appeal 2014-008426 Application 12/502,342 We are not persuaded. As explained by the Examiner, “in example 1 Britton discloses the hydrogen chloride (a reactant) is continuously added for approximately 35 hours (flow rate) at the end of which time no more water (a liquid medium) is distilled from the reaction mixture” (Ans. 16). Claim 17 Appellants contend that Britton “neither disclosure nor suggestion of a particular reaction time associated with a batch process, let alone the presently-recited reaction time of from 1 h to 10 h” (App. Br. 13). We are not persuaded. As explained by the Examiner, “Example 4 [of Britton] conducts a digestion for 3 hours, so there is a suggestion that the batch reaction took at least 3 hours” (Ans. 16). SUMMARY We affirm the rejection of claims 1 and 8—20 under 35 U.S.C. § 103(a) over Britton in view of Steen and Smidt, and further in view of C. F. Boehringer, Griesheim-Elektron, Solvay, Jakobson, and Wang. TIME PERIOD FOR RESPONSE No time period for taking any subsequent action in connection with this appeal may be extended under 37 C.F.R. § 1.136(a). AFFIRMED 13 Copy with citationCopy as parenthetical citation