DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claim Status
Claims 1, 9, and 14 are amended. Claim 13 is cancelled.
The amendments to claims 9 and 14 overcome the previous claim objections.
Claims 1-12 and 14 are pending for examination below.
Response to Arguments
Applicant's arguments filed 11 June 2026 have been fully considered but they are not persuasive.
Applicant argues on page 8 of the Remarks that the formula of Davis which is shown in the rejection of original claim 13 is a cycloalkene, not the claimed cycloalkane, and thus Davis in view of Harvey does not teach the cycloalkane formulas now amended into instant claim 1.
In response, the Examiner agrees that the formula in Davis is a cycloalkene. However, as previously explained in the Office Action, the rejection of claims 1 and 13 is a combination obviousness rejection over Davis in view of Harvey, where Harvey teaches the hydrogenation step. When the process of hydrogenation is performed on the cycloalkene shown in the formula of Davis, the resulting compound will be a cycloalkane having the claimed formula FX4a, as explained in detail in the rejection below. Thus, the rejection over Davis in view of Harvey is maintained.
Claim Rejections - 35 USC § 103
Claims 1-3, 6-12, and 14 are rejected under 35 U.S.C. 103 as being unpatentable over Davis et al. (US 2014/0364631) in view of Harvey (US 2015/0011809).
With regard to claims 1-3, 6, 7, and 10, Davis teaches a method for catalyzed Diels-Alder cycloaddition (instant claim 2) between a diene and a dienophile to produce a substituted cyclohexene (claimed cyclic olefin) (paragraph [0030]), where the diene and dienophile are derived from biomass (paragraph [0042]).
Davis further teaches the diene has the formula (A) (paragraph [0030]).
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In this formula, when Ra is an alkyl group having 1 carbon atom and Rb-, Rc, Ra’, Rb’, and Rc’ are each hydrogen (paragraph [0031]), the formula A is butadiene, as claimed in instant claims 1 and 7.
Davis also teaches the dienophile has the formula (C) (paragraph [0030]).
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In this formula, when Re is an alkyl group having two carbon atoms and Rf is hydrogen (paragraph [0031]), the formula C is butene, which is a dienophile comprising an olefin of formula FX2a of instant claims 1 and 10.
Davis additionally teaches that the substituted cyclohexene (claimed cyclic olefin) has formula (D) below (paragraph [0030]).
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As above, Ra is selected to be an alkyl group having 1 carbon atom, Rb-, Rc, Ra’, Rb’, Rc’, and Rf are each selected to be hydrogen, and Re is selected to be an alkyl group having two carbon atoms (paragraph [0031]).
Davis does not teach hydrogenation of the substituted cyclohexene (cyclic olefin) to produce a cyclic alkane.
Harvey teaches a process for forming high density fuels from biomass (paragraph [0003]). Harvey teaches producing compounds from biomass, Diels-Alder cycloaddition of the compounds to produce a cyclic olefin, and then catalytically hydrogenating (instant claims 1 and 3) the cyclic olefin to produce saturated cyclic hydrocarbons (paragraph [0013]). Harvey further teaches that fuels comprising cyclic alkanes with linear hydrocarbon side chains from renewable sources have a higher density and high enough cetane number to be used in a diesel engine, thus being applicable as turbine and diesel fuels while reducing net greenhouse gas emissions (sustainable aviation fuel instant claim 6) (paragraph [0009]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to hydrogenate the cyclohexenes (cyclic olefins) of Davis, because each of Davis and Harvey teaches producing cyclic olefins comprising linear alkyl side chains from cycloaddition of products from biomass, Davis is silent regarding further use of the cyclohexene (cyclic olefin), and Harvey teaches the hydrogenation of cyclic olefins comprising linear hydrocarbon side chains provides a high density fuel which is applicable for turbine and diesel fuels while reducing net greenhouse gas emissions (paragraph [0009]).
When the cyclohexene of formula (D) above is hydrogenated as taught by Davis in view of Harvey, the resulting hydrogenated compound is equivalent to a cyclic alkane of formula FX4a of instant claim 1 where R3 is a C1 alkane, R2 is a C2 alkane, and R1 is a H atom.
With regard to claim 8, Davis teaches formula (A) above. When Rc is an alkyl group having 1 carbon atom and Ra-, Rb, Ra’, Rb’, and Rc’ are each hydrogen (paragraph [0031]), the formula A is isoprene as claimed.
With regard to claim 9, Davis teaches that formula (A) can be more preferably Formula (1) (paragraph [0038]).
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When R1 and R2 are each an alkyl group having 1 carbon atom (paragraph [0039]), the formula (1) is equivalent to formula FX1f of instant claim 9.
With regard to claim 11, the dienophile has formula (C) above. When Re is an alkyl group having three carbon atoms and Rf is a hydroxycarbonyl group (paragraph [0031]), the formula (C) is equivalent to formula FX3a of instant claim 11.
With regard to claim 12, the dienophile has formula (C) above. When Re is an alkyl group having one carbon atoms and Rf is an alkoxycarbonyl group having one carbon atom in the alkyl group (paragraph [0031]), the formula (C) is equivalent to formula FX3d of instant claim 12.
With regard to claim 14, Davis teaches that the diene has formula (A) and the cyclohexene (claimed cyclic olefin) has formula (D) (paragraph [0030]) and that Ra, Rb-, Rc, Ra’, Rb’, Rc’, and Re can each be and Rf can be selected to be an alkyl group having two carbon atoms (paragraph [0031]). In this case, when the cyclohexene having these substituents is hydrogenated as in the process of Davis in view of Harvey described above, the resulting hydrogenated compound is equivalent to a compound of formula FX5a of instant claim 14.
Claims 4 and 5 are rejected under 35 U.S.C. 103 as being unpatentable over Davis et al. (US 2014/0364631) in view of Harvey (US 2015/0011809) as applied to claim 1 above, and further in view of Yan et al. (Mechanistic Insights into One-Step Catalytic Conversion of Ethanol to Butadiene over Bifunctional Zn-Y/Beta Zeolite) and Zhang et al. (Isolated Metal Sites in Cu-Zn-Y/Beta for Direct and Selective Butene-Rich C3+ Olefin Formation from Ethanol).
With regard to claim 4, Davis teaches the process above, where Formula (A) (diene) can be butadiene from biomass (paragraph [0042]).
Davis fails to specifically teach how the diene is produced from biomass.
Yan teaches a process for forming butadiene from bio-ethanol by reacting the bioethanol over a Zn-Y/Beta catalysts (Zn-Y catalyst as claimed) (Abstract and page 2760, Introduction, first paragraph). Yan further teaches that it is desired to provide an alternative route to butadiene from ethanol and that the Zn-Y/Beta catalyst provides the benefits of increased butadiene selectivity (page 2760, Introduction, first paragraph and page 2761, second full paragraph).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the process of Yan to produce the butadiene of Davis, because Davis teaches producing butadiene from biomass, Davis is silent regarding the specific reaction, and Yan teaches that conversion of bioethanol to butadiene over Zn-Y/Beta catalysts provides a desired alternative butadiene synthesis route and increased butadiene selectivity (page 2760, Introduction, first paragraph and page 2761, second full paragraph).
Yan does not specifically teach the bioethanol is from conversion of biomass. However, Zhang teaches that it is known to convert lignocellulosic biomass to bioethanol (page 9885, Introduction).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use biomass as taught by Davis to produce the bioethanol of Yan, which is then reacted to form the butadiene, because Yan is silent regarding the source of bioethanol, and Zhang teaches it is known to produce bioethanol from biomass (page 9885, Introduction).
With regard to claim 5, Davis teaches the process above, where Formula (B) (dienophile) can be butene from biomass (paragraph [0042]).
Davis fails to specifically teach how the dienophile is produced from biomass.
Zhang teaches a process for forming butenes from bioethanol by reacting the bioethanol over a Cu-Zn-Y/Beta catalysts (Zn-Y catalyst as claimed) (Abstract), where the bioethanol is produced from lignocellulosic biomass (page 9885, Introduction). Zhang further teaches that it is desired to provide a direct synthesis of C3+ olefins from bioethanol for production of renewable transportation fuels such as aviation biofuels and that the Cu-Zn-Y/Beta catalyst provides selective conversion to the desired olefins (Abstract).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the process of Zhang to produce the dienophile which is butene of Davis, because each of Davis and Zhang teaches producing butenes from biomass, Davis is silent regarding the specific reaction, and Zhang teaches that conversion of bioethanol from biomass to butenes over Cu-Zn-Y/Beta catalysts provides a desired direct synthesis of C3+ olefins from bioethanol for production of renewable transportation fuels such as aviation biofuels and that the Cu-Zn-Y/Beta catalyst provides selective conversion to the desired olefins (Abstract).
Conclusion
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 ALYSSA L CEPLUCH whose telephone number is (571)270-5752. The examiner can normally be reached M-F, 8:30 am-5 pm, EST.
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/Alyssa L Cepluch/Examiner, Art Unit 1772
/Renee Robinson/Primary Examiner, Art Unit 1772
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