Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
DETAILED ACTION
1. This application is a 371 of PCT/EP2022/057290 03/21/2022; FOREIGN APPLICATIONS: EP 21163929.9 03/22/2021.
Claims 1-10, 12, 14-18 are pending.
Response to Restriction Election
2. Applicant’s election of group I in the reply filed on March 23, 2026 is acknowledged. The election was made with traverse and the examiner finds the arguments unpersuasive. According to arguments, the Hammond reference was an “A” type reference in the ISR and did not anticipate the claims. While there are a number of A references cited on the ISR, Hammond was not cited on the ISR and was only provided by the applicant in the IDS. The findings of a foreign patent offices do not bind the USPTO. All written opinions of PCT applications are nonbinding and a patent does not issue; and the international preliminary examination report (IPER) is nonbinding on the Elected States. See M.P.E.P. § 1878.01, Item V. Findings of foreign patent offices do not obviate applicant’s burden to comply with the relevant patent statutes of the United States.
Crucially applicant provides nothing to dispute the examiners analysis with regard to Hammond anticipating the claims of September 20, 2023. Table 1 on page 3932 shows that MgO alone (entry 12) as well as MgO in the presence of Au (entries 10-11) catalyzes the reaction of claim 1, “a Reaction conditions: glycerol/urea molar ratio: 1 : 1.5, temperature: 150 ◦C, catalyst: 0.25 g, time: 4 h…..product (7) = 4-(hydroxymethyl) oxazolidin-2-one”. Applicant submits amended claims with the response of March 23, 2026 that specify ratios of reactants and catalysts and argues that these amended claims have unity of invention. Unity of invention is not perpetually reevaluated upon the submission of amendments. Claim 2 is not rejected and claim 16-17 can be rejoined based upon the change in dependency when the rest of the elected invention is in allowable form.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
3. Claim 7 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention. Claim 7 has the trademarks decalin and proglyde. Decalin is registered to MERCK KGAA (KOMMANDITGESELLSCHAFT AUF AKTIEN (KGAA); GERMANY). Proglyde is registered to DOW CHEMICAL COMPANY, THE (CORPORATION; DELAWARE). Where a trademark or trade name is used in a claim as a limitation to identify or describe a particular material or product, the claim does not comply with the requirements of 35 U.S.C. 112, second paragraph. See Ex parte Simpson, 218 USPQ 1020 (Bd. App. 1982). The claim scope is uncertain since the trademark or trade name cannot be used properly to identify any particular material or product. A trademark or trade name is used to identify a source of goods, and not the goods themselves. Thus, a trademark or trade name does not identify or describe the goods associated with the trademark or trade name. In the present case, the trademark/trade name is used to identify/describe the compounds and, accordingly, the identification/description is indefinite.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
4. Claim(s) 1, 3, 5, 9-10, 12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hammond, Ceri ”Synthesis of glycerol carbonate from glycerol and urea with gold-based catalysts.” Dalton Transactions, 2011, 40(15), 3927-3937 (cited on the IDS) and Dibenedetto “Catalytic Synthesis of Hydroxymethyl-2-oxazolidinones from Glycerol or Glycerol Carbonate and Urea ChemSusChem (2013), 6(2), 345-352 (cited on the IDS). The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
Determining the scope and contents of the prior art.
Hammond in Table 1 on page 3932 shows that MgO alone (entry 12) as well as MgO in the presence of Au (entries 10-11) catalyzes the reaction of claim 1,
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“a Reaction conditions: glycerol/urea molar ratio: 1 : 1.5, temperature: 150◦C, catalyst: 0.25 g, time: 4 h…..product (7) = 4-(hydroxymethyl) oxazolidin-2-one”. Product (7) is the compound of formula (II). This is a urea glycerol ratio of 1.5:1 falling within the claimed range. The catalyst was in an amount of 0.25g. According to page 3929 col. 1:
“The synthesis of glycerol carbonate was performed as follows. Glycerol (typically 13.8 g, 0.15 moles) was added to a round bottom flask (100 mL) and dried at the desired reaction temperature (150 ◦C) under a flow of dry nitrogen for 20 min. The desired amount of urea (typically 13.5 g, 0.225 moles (molar ratio glycerol : urea 1 : 1.5)) was then added, and once solubilised, the desired catalyst (250 mg) was added.” Since no unit of catalyst ratio is given on a molar basis catalyst to glycerol is 0.006 : 0.15 mols which is around 4%.
Dibenedetto teaches the same reaction as Hammond where the product is labeled 6.
Dibenedetto also shows mechanistically how the 2-oxazolidinone is formed in Scheme 4 on page 346 and Scheme 6 on page 347. Crucially Dibenedetto shows that the reaction is highly dependent on temperature.1 “The thermochemistry of the overall reaction, as well as of the assumed steps, has been examined computationally (for details, see the Experimental Section). The Gibbs free energies obtained under standard and experimental conditions are listed in Table 2. The data indicate that the formation of product isomers 6 and 6’ is highly exergonic and, of the three reaction steps (Scheme 4), the addition of urea to 1 is clearly thermodynamically disfavored.” [page 346 col. 2] “Figure 1 shows the 13C NMR spectra of the compounds formed in the reaction of 1 with urea. Starting from Figure 1 a (glycerol carbonate+urea), after heating at 398 K for 2 h, new signals appeared in addition to those of the starting compounds. Signals between d=157 and 158 ppm are attributed to 2 and 2’, whereas signals between d=158 and 159 ppm are due to 5 and 5’. By heating the same mixture at T>408 K, such signals disappear and the unique signal of 2-oxazolidinone appears at d=159.5 ppm (Figure 1 c). Indeed, we have shown that two isomers 6 and 6’ are formed with a molar ratio equal to 1:1….As an attempt to increase the reaction rate, the reaction temperature was increased to 453 K. The conversion of glycerol carbonate significantly increased, affording 2-oxazolidinones in 21% yield after 3 h of reaction,” As can be seen in Figure 3, the amounts of products can be controlled by altering temperature and time as shown in Figure 3:
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In addition, the use of additional catalyst increases the yield:
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“When the reaction was carried out by loading the catalyst at 20% w/w rate at the zero time point under the same reaction conditions reported in Figure 5, 25% oxazolidinone (isolated) was obtained at 408 K. At a catalyst loading of 25 %, the conversion was close to 40% with a selectivity of 100 %.”
Ascertaining the differences between the prior art and the claims at issue.
The process of the instant claims differs from that of Hammond by the amount of catalyst loaded into the reaction.2 Hammond uses 4 mol % of MgO. The instant claims are drawn to the use of 10% to 100%3 catalyst loading. The prior art differs from the type of catalyst from Dibenedetto. Dibenedetto uses g-ZrP, while the instant claims use MgO.
Resolving the level of ordinary skill in the pertinent art and Considering objective evidence present in the application indicating obviousness or nonobviousness.
One would be motivated to increase the catalyst loading in the process of Hammond and optimize the temperature since they lead to increased selectivity for the claimed product. According to Dibenedetto “When the reaction was carried out by loading the catalyst at 20% w/w rate at the zero time point under the same reaction conditions reported in Figure 5, 25% oxazolidinone (isolated) was obtained at 408 K. At a catalyst loading of 25 %, the conversion was close to 40% with a selectivity of 100 %.” The process claimed can also be viewed as simply swapping out the catalyst in the process of Dibenedetto for that of Hammond. Since the g-Zr phosphate catalyst is much more expensive than the MgO catalyst it would be obvious to substitute the MgO in the process since it was known to catalyze the same reaction.
With respect to claim 12, molar proportions are optimized since they are results effective. Increasing a concentration of urea two fold over that of Hammond should accelerate the reaction(s). Mere optimization of a prior art process is within the scope of what one skilled in the art would be capable of and is insufficient to establish patentable unobviousness; see In re Hoeschele (CCPA 1969) 406 F2d 1403, 160 USPQ 809; In re Cole (CCPA 1964) 326 F2d 769,140 US PQ 230 (molar proportions); Ex parte Khusid et at (POBA 1971) 174 USPQ 59 (molar proportions, temperature difference); In re Mostovych et al. (CCPA 1964) 339 F2d 455, 144 USPQ 38; In re Aller et al (CCPA 1955) 220 F2d 454, 105 USPQ 233 ( pH, time and temperature). All of this is especially true in light of the clear teaching that these parameters are results effective. The ordinary artisan is well aware that “discovery of an optimum value of a result effective variable . . . is ordinarily within the skill of the art.” In re Boesch, 617 F.2d 272, 276 (CCPA 1980).
5. Claim(s) 6-8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hammond and Dibenedetto as applied to claims 1, 3, 5, 9-10, 12 above, and further in view of OKUTSU JP 2007039347A. Claims 6-8 are drawn to the use of a high boiling solvent in the reaction. Typically in thermal reactions a solvent is added and the various glymes and ethers such as those in claim 7-8 are already known in this context. OKUTSU teaches the use of these same solvents in the same reactions with glycerol and urea as discussed on page 2 of the translation:
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Using such a solvent allows for effective heat transfer and higher temperatures.
Allowable Subject Matter
6. Claims 2, 4, 14-15, 18 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims. Claim 4 is drawn to the use of magnesium metal, and while magnesium oxide (MgO) is the most common surface impurity due to magnesium's high reactivity with air there is no suggestion to use magnesium metal for the reaction in the prior art. Mg is quite reactive and would be expected to react in different ways. The claim is limited to the metal itself not metal contaminated with metal oxide. The reaction of claim 2 is unremarkable, however it is apparently not a known reaction and in the context of the process of claim 1 is patentable. Debenneto remarks, “In the last step of the synthesis reported in Scheme 6, compounds 5 and 5’ lose ammonia to afford 2-oxazolidinones 6 and 6’. The reaction was carried out under vacuum. If ammonia was not removed, compound 5 reverted back to 4.” While reversible with ammonia no basic hydrolysis is contemplated and as best as can be determined the reaction has not been used for preparing serinol.
Conclusion
4. Any inquiry concerning this communication or earlier communications from the examiner should be directed to DAVID K O'DELL whose telephone number is (571)272-9071. The examiner can normally be reached on Monday - Friday 9:30 - 7:00 PM.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Clinton Brooks can be reached on 571-270-7682. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/DAVID K O'DELL/Primary Examiner, Art Unit 1621
1 Other workers substantiate this finding with various catalysts see, Indran “An accelerated route of glycerol carbonate formation from glycerol using waste boiler ash as catalyst” RSC Advances (2014), 4(48), 25257-25267. “It is evident that by prolonging the reaction time, decomposition of glycerol carbonate into (6) increases and at the same time formation of compound (5) originated from carbamate intermediate also increased.” Compound 5 is the oxazolidine-2-one, see also: Kim “Synthesis of glycerol carbonate from urea and glycerol using polymer-supported metal containing ionic liquid catalysts” Appl. Catal., A, 2014, 473,31–40. “The 13C NMR (Fig. 9) [22,23] and FT-IR (Fig. 10) [23,53] profiles show that the intensity of the peaks at 77.5 ppm in the NMR spectrum and at 1730 cm−1 in the FT-IR spectrum, corresponding to compound (5), increased above 140◦C and the selectivity of (5) increased to 16.7% at 160◦C” [page 37 col. 1]
2 The unit of the ratio is not given in the claims.
3 Loading of 100% is not a catalytic amount.
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