DETAILED ACTION
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 .
The examiner has considered the amendment and response filed by applicants on December 29, 2025. In light of the amendment, the examiner has withdrawn the rejections made in the previous Office Action; however, the following new rejection is being made.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
Claim(s) 12, 13, and 15-19, and 21-24 is/are rejected under 35 U.S.C. 103 as being unpatentable over Eremenko et al. (Chem. Bull., 26, 1977) in view of Kesling, Jr. et al. (US 5,308,365).
The instant claims are drawn to a process for producing nitrates of ethers of glycerol and ethanol by conducting an etherification reaction between glycerol and the alcohol; separating the resulting ethers; nitration of the ethers, wherein substitution of the two available hydroxyl groups forms dinitrated ethers, and wherein the glycerol (glycerin) is from a biodiesel production process.
Eremenko et al. teach a process for preparing dinitrates of glycerol alkyl ethers by contacting sodium and an n-alcohol having from 1 to 10 carbon atoms with glycerol-alpha-monochlorohydrin at a temperature from 50 to 70°C to make the corresponding glycerol alkyl ethers. The separated glycerol alkyl ethers are nitrated using a mixture of nitric acid and acetic acid at a temperature from 0 to -10°C to produce the corresponding dinitrates (page 400).
The difference between the present invention and the process taught by Eremenko et al. is that the glycerol (glycerin) is from a biodiesel production process in the present invention, and the reference teaches glycerol monochlorohydrin as the source of glycerol. Also, Eremenko et al. conduct their etherification process using sodium metal, while the instant claims, as amended, conduct the etherification reaction using an acidic catalyst.
The examiner does not find that these are patentable distinctions. Unless applicants can show unexpected results afforded by sourcing the glycerol from a biodiesel production process, the examiner contends it would have been obvious to a person having ordinary skill in the art that the etherification and nitration processes taught by Eremenko et al. would have proceeded regardless of the source of glycerol.
Moreover, Kesling, Jr. et al. teach that glycerol that is derived from soybean oil, i.e., bio-derived glycerol, may be etherified by reaction with a t-alkyl alcohol, in the presence of a highly cross-linked sulfonic acid resin catalyst (col. 3, line 22 to col.4, line 60). Therefore, in view of the combined reference teaching, a person having ordinary skill in the art would recognize that glycerol used in an etherification reaction may be derived from a bio-derived source, e.g., a source of biodiesel, such as soybean oil. Such as person is also taught that the etherification reaction may be conducted using a solid acid catalyst, such as the ion exchange resin taught by Kesling, Jr. et al. As such, the claims are obvious in view of the combined reference teaching.
Claim(s) 20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Eremenko et al. and Kesling, Jr. et al. as applied to claims 12, 13, 15-19, and 21-24 above, and further in view of Reed, Jr. (US 3,968,139).
The instant claim conducts the nitration step of the present invention using a mixture of sulfuric acid and nitric acid, while Eremenko et al. use nitric acid and acetic acid in their process; however, Reed, Jr. teaches that nitration may be conducted using a mixture of nitric acid and sulfuric acid. Accordingly, the instant claims are rendered obvious, as Reed, Jr. teaches that nitration reactions may be conducted using a nitric acid and sulfuric acid mixture; such reagents can be used in the process taught by Eremenko et al. for the nitration step.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SIKARL A WITHERSPOON whose telephone number is (571)272-0649. The examiner can normally be reached M-F 9am-9pm IFP.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/SIKARL A WITHERSPOON/Primary Examiner, Art Unit 1692