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 .
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after allowance or after an Office action under Ex Parte Quayle, 25 USPQ 74, 453 O.G. 213 (Comm'r Pat. 1935). Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, prosecution in this application has been reopened pursuant to 37 CFR 1.114. Applicant's submission filed on 5/11/26 has been entered.
Non-Final Rejection
The Status of Claims:
Claims 14-15, 17-30 are pending.
Claims 14-15, 17-30 are rejected.
DETAILED ACTION
1. Claims 14-15, 17-30 are under consideration in this Office Action.
Priority
2. It is noted that this application is a 371 of PCT/EP2021/057238 03/22/2021, which has a foreign priority document EPO EP20164932.4 03/23/2020.
Drawings
3. None.
IDS
4. The IDS filed on 5/11/26 is reviewed by the examiner.
Claim Rejections - 35 USC § 103
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
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.
The factual inquiries set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
5. Claims 14-15, 17-25 are rejected under 35 U.S.C. 103 as being unpatentable over Teles et al (WO 2015/010991 A1) in view of Thiele et al (Journal of Molecular Catalysis A: Chemical 1 17 (1997) 351-356).
Applicant claims the followings:
14. (Currently amended) A process for the preparation of propylene oxide, comprising (i) providing a reaction mixture comprising propylene, water, organic solvent, and hydrogen peroxide;(ii) contacting the reaction mixture provided in (i) in an epoxidation zone with an epoxidation catalyst comprising a zeolitic material having a framework structure comprising Si, O, and Ti, and subjecting the reaction mixture to epoxidation reaction conditions in the epoxidation zone, obtaining, in the epoxidation zone, a mixture comprising propylene oxide, water, and organic solvent;(iii) removing an effluent stream from the epoxidation zone, the effluent stream comprising propylene oxide, water, and organic solvent;wherein the reaction mixture provided in (i) and subjected to (ii) containscomprises in an amount of at most 500 mg per kg hydrogen peroxide comprised in said reaction mixture at least one aliphatic oxygen containing compound having 8 to 10 carbon atoms;wherein the at least one aliphatic oxygen containing compound having 8 to 10 carbon atoms is selected from the group consisting of secondary mono alcohols C9H200, mono ketones C9Hi80, and mixtures of secondary mono alcohols C9H200 and mono ketones C9H18O and comprises at least diisobutyl carbinol.
15. (Previously Presented) The process of claim 14, wherein the reaction mixture provided in (i) and subjected to (ii) contains the at least one aliphatic oxygen containing compound having 8 to 10 carbon atoms in an amount in the range from 0 to 500 mg per kg hydrogen peroxide comprised in the reaction mixture.
17. (Previously Presented) The process of claim 14, wherein providing the reaction mixture in (i) comprises (i. 1) providing an aqueous hydrogen peroxide solution;(i.2) admixing the aqueous hydrogen peroxide solution provided in (i.1) with propylene and organic solvent, obtaining the reaction mixture;wherein the aqueous hydrogen peroxide solution provided in (i.1) and subjected to (i.2) contains the at least one aliphatic oxygen containing compound having 8 to 10 carbon atoms in an amount of at most 500 mg per kg hydrogen peroxide comprised in the reaction mixture.
18. (Previously Presented) The process of claim 17, wherein the aqueous hydrogen peroxide solution provided in (i.1) and subjected to (i.2) contains the at least one aliphatic oxygen containing compound having 8 to 10 carbon atoms in an amount in the range from 0 to 500 mg per kg hydrogen peroxide comprised in the aqueous hydrogen peroxide solution.
19. (Currently amended) The process of claim 17, wherein the aqueous hydrogen peroxide solution provided in (i.1) and subjected to (i.2) has a total organic carbon content (TOC) in the range from 100 to 800 mg per kg hydrogen peroxide comprised in the aqueous hydrogen peroxide solution, determined as described in Reference Example 5according to DIN EN 1484.
20. (Previously Presented) The process of claim 17, wherein the aqueous hydrogen peroxide solution provided in (i.1) and subjected to (i.2) is obtained from an anthraquinone process.
21. (Previously Presented) The process of claim 14, wherein the epoxidation reaction conditions according to (ii) comprise trickle-bed conditions or wherein the epoxidation reaction conditions according to (ii) comprise fixed-bed conditions.
22. (Previously Presented) The process of claim 14, wherein (ii) is carried out continuously.
23. (Currently amended) A reaction mixture for preparing propylene oxide, comprising propylene, water, organic solvent, and hydrogen peroxide, wherein the reaction mixture comprises at least one aliphatic oxygen containing compound having 8 to 10 carbon atoms in an amount of at most 500 mg per kg hydrogen peroxide comprised in the reaction mixture;wherein the at least one aliphatic oxygen containing compound having 8 to 10 carbon atoms is selected from the group consisting of secondary mono alcohols C9H200, mono ketones C9His0, and mixtures of secondary mono alcohols C9H200 and mono ketones C9HisOi and comprises at least one diisobutyl carbinol.
24. (Previously Presented) The reaction mixture of claim 23, being obtained by a process comprising providing a reaction mixture comprising propylene, water, organic solvent,and hydrogen peroxide.
25. (Previously Presented) A catalytic epoxidation system for preparing propylene oxide, the catalytic epoxidation system comprising an epoxidation catalyst comprising a zeolitic material having a framework structure comprising Si, O, and Ti, and further comprising the reaction mixture comprising propylene, water, and organic solvent according to claim 23.
26. (New) The process of claim 14, wherein the material having a framework structure comprising Si, 0, and Ti comprised in the epoxidation catalyst is a titanium zeolite having an MFl framework type, or an MWW framework type.
27. (New) The process of claim 14, wherein the material having a framework structure comprising Si, 0, and Ti is a titanium silicalite-1 (TS-1)).
28. (New) The process of claim 14, wherein the organic solvent comprises at least an alcohol.
29. (New) The process of claim 14, wherein the organic solvent comprises at least an alcohol which comprises C1 to C5 mono alcohol or a mixture of two or more C1 to C5 alcohols.
30. (New) The process of claim 14, wherein the organic solvent is an alcohol which comprises methanol.
Determination of the scope and content of the prior art
Teles et al discloses a continuous process for the preparation of propylene oxide, as in claim 22 comprising
(i) providing a liquid feed stream comprising propene, hydrogen peroxide, acetonitrile, water, optionally propane, and at least one dissolved potassium salt of a phosphorus oxyacid;
(ii) passing the liquid feed stream provided in (i) into an epoxidation reactor comprising a catalyst comprising a titanium zeolite of structure type MWW comprising zinc, and subjecting the liquid feed stream to epoxidation reaction conditions in the epoxidation reactor, obtaining a reaction mixture comprising propylene oxide, acetonitrile, water, the at least one dissolved potassium salt of a phosphorus oxyacid, optionally propene, and optionally propane;
(iii) removing an effluent stream from the epoxidation reactor, the effluent stream comprising propylene oxide, acetonitrile, water, as in claim 14 at least a portion of the at least dissolved potassium salt of a phosphorus oxyacid, optionally propene, and optioionally propane (see page 2, line 25 to page 3 ,line 2).
Moreover, it is preferred to employ a stream comprising hydrogen peroxide which is obtained as crude hydrogen peroxide solution by extraction of a mixture which results from a process known as anthraquinone process as in claim 20 (see page 12, lines 13-15).
Also, the effluent stream removed according to (iii) may contain at least one component B wherein the normal boiling point of the at least one component B is higher than the normal boiling point of acetonitrile and wherein the decadic logarithm of the octanol-water partition coefficient (log Kow) of the at least one component B is greater than zero. Regarding the determination of the octanol-water partition coefficient, reference is made to Reference Example 5 hereinbelow. Typically, the at least one component B contained in the effluent stream removed according to (iii) either is a by-product and/or a side-product obtained during the epoxidation reaction in (ii), and/or is a compound which is formed during at least one of the work-up stages being preferably carried out downstream of step (ii) and which accumulates if certain process streams of the preferred integrated process are recycled into (i), and/or is contained as an impurity in at least one of the starting materials employed in (i) such as an impurity in the acetonitrile or an impurity in the hydrogen peroxide. Preferably, the at least one component B is propionitrile, 1-nitropropane, 2-nitropropane, 3-methylbutanenitrile, n-pentanenitrile, 1-pentanol, 2-pentanol, 2-butanone, 2-pentanone, 2-hexanone, 4-methyl-2-heptanone, 2,6-dimethyl-4-heptanol, 4,6-dimethyl-2-heptanol, 2,6-dimethyl-4-heptanone, 4,6-dimethyl-2-heptanone, as in claim 14 , 2,6-dimethyl-4,6-heptandiol, 2,4-dimethyloxazoline, 2,5-dimethyloxazo-line, cis-2,4-dimethyl-1 ,3-dioxolane, trans-2,4-dimethyl-1 ,3-dioxolane, at least one impurity contained in the hydrogen peroxide stream; a combination of two or more of these compounds. Preferably, the at least one impurity contained in the hydrogen peroxide stream employed in (i) is an alkyl phosphate such as tris-(2-ethylhexyl) phosphate, a nonyl alcohol such as diisobutylcarbinol, an alkylcyclohexanol ester such as 2-methyl-cyclohexylacetate, an N ,N-dialkyl carbonamide (see page 40 ,lines 20-36).
Furthermore, the at least one component B in an amount of from 0.01 to 3 weight-%, preferably from 0.015 to 2 weight-%, as in claims 14-15 ,more preferably from 0.02 to 1 weight-% based on the total weight of the effluent stream(see page 41 , lines 22-24)
Generally, the titanium zeolite of framework structure type MWW comprising zinc may comprise at least one further element other than titanium, silicon, oxygen as in claim 14, 26 (see page 15 ,lines 6-7) present in the reactor as fixed bed catalyst as in claim 21 (see page 70 , claim 19) .
The zeolitic material having an MWW framework structure obtained from (c) has a Si content in the range of from 30 to 40 weight-%, calculated as elemental Si, a total organic carbon content (TOG) in the range of from 0 to 14 weight-%, as in claim 19 and a Ti content of from 2.1 to 2.8 weight-%, calculated as elemental titanium, in each case based on the total weight of the zeolitic material.(see page 30, lines 1-6).
The current invention, however, differs from the prior art in that the claimed amount of the at least one aliphatic oxygen containing compound having 8 to 10 carbon atoms at most 500 mg per kg hydrogen peroxide comprised in said reaction mixture and the use of titanium silicalite and methanol solvent are not exemplified in the prior art.
Thiele et al teaches that a continuous epoxidation reactions were run in a similar reactor, that was fitted with a line for withdrawing product, which had a filter mounted inside the reactor and submerged in the reaction mixture to retain the catalyst in the reaction mixture throughout the reaction. The reactor was charged with 5 g titanium silicalite catalyst as in claim 27and 295 g methanol, as in claims 28-30 heated to 40°C and pressurized with propene at 3 bar. Then, a mixture of 464 g 50% hydrogen peroxide, 2668 g methanol and 68 g methyl tert-butyl ether was added at a rate of 300 g/h. At the same time, propene was supplemented to maintain the pressure and the reaction mixture was withdrawn over the filter to keep the content of the reactor at a constant weight (see page 352, the left col. , the last paragraph to the right col. the first paragraph).
Ascertainment of the difference between the prior art and the claims
The difference between the current application and the applied Teles et al art is that the Teles et al does not expressly exemplify the claimed at least one aliphatic oxygen containing compound having 8 to 10 carbon atoms in an amount of at most 500 mg per kg hydrogen peroxide comprised in said reaction mixture and the use of titanium silicalite and methanol solvent. The deficiencies of Teles et al are cured partially by the Thiele et al.
The difference between the current application and the applied Thiele et al art is that the Thiele et al does not expressly exemplify the claimed the claimed at least one aliphatic oxygen containing compound having 8 to 10 carbon atoms in an amount of at most 500 mg per kg hydrogen peroxide comprised in said reaction mixture and a total organic carbon content (TOC) range in the aqueous hydrogen peroxide, the aqueous hydrogen peroxide solution s obtained from an anthraquinone process.
The deficiencies of Thiele et are cured partially by the Teles et al.
Resolving the level of ordinary skill in the pertinent art.
Regarding the Claims 14-15, 17-18, 23, with respect to the lack of exemplifying the claimed amount of at most 500 mg per kg hydrogen peroxide comprised in the reaction mixture at least one aliphatic oxygen containing compound having 8 to 10 carbon atoms, the prior art is unspecified about it. However, Teles et al
does teach indirectly that organic impurities such as the at least one component B which is 2,6-dimethyl-4-heptanol, 4,6-dimethyl-2-heptanol, 2,6-dimethyl-4-heptanone, 4,6-dimethyl-2-heptanone, at least one impurity contained in the hydrogen peroxide stream; a combination of two or more of these compounds. Preferably, the at least one impurity contained in the hydrogen peroxide stream employed in (i) is an alkyl phosphate such as tris-(2-ethylhexyl) phosphate, a nonyl alcohol such as diisobutylcarbinol (see page 40 ,lines 20-36) in an amount of from 0.01 to 3 weight-%, preferably from 0.015 to 2 weight-% based on the total weight of the effluent stream(see page 41 , lines 22-24). From these, it seems reasonable for the skilled artisan in the art to have estimated the claimed amount of at least one aliphatic oxygen containing compound having 8 to 10 carbon atoms in at most 500 mg per kg hydrogen peroxide by a routine experimentation.
Therefore, it would have been obvious to the skilled artisan in the art to be motivated to estimate the claimed content of a C8-C10-aliphatic oxygen containing compounds in term of mg per kg hydrogen peroxide egarding the claimed limit range. This is because the skilled artisan in the art would expect such an evaluation to be reasonable and logical within the purview of the skilled artisan in the art.
Considering objective evidence present in the application indicating obviousness or nonobviousness.
Teles et al expressly discloses the continuous process for the preparation of propylene oxide, comprising a liquid feed stream comprising propene, hydrogen peroxide, acetonitrile, water, passing the liquid feed stream provided in (i) into an epoxidation reactor comprising a catalyst comprising a titanium zeolite of structure type MWW containing Si, O and Ti and subjecting the liquid feed stream to epoxidation reaction conditions in the epoxidation reactor, obtaining a reaction mixture comprising propylene oxide, removing an effluent stream containing organic impurities such as a C8-C10-aliphatic oxygen containing compounds from the epoxidation reactor, the effluent stream comprising propylene oxide.
Although Teles et al does not teach the use of titanium silicalite and methanol solvent, Thiele et al does describe that the continuous epoxidation reactions can be conducted by reacting propene in a solution of hydrogen peroxide in the presence of titanium silicalite catalyst and methanol.
Both prior art are closely relate to each other with respect to the propylene epoxidation with hydrogen peroxide by using a titanium catalyst. Furthermore, Thiele et al does give a guidance that the use of methanol solvent in combination with titanium silicalite catalyst can enhance the catalytic activity during the epoxidation process (see page 353, Fig. 2).
So, if the skilled artisan in the art had desired to improve the catalytic activity during the epoxidation process, it would have been obvious to the skilled artisan in the art before the effective filing date of the claimed invention to be motivated to incorporate teachings of Thiele‘s et al methanol solvent and titanium silicalite catalyst as an alternative into Teles et al epoxidation process. This is because the skilled artisan in the art would expect such combined processes to be feasible and successful as shown in the prior art.
Conclusion
Claims 14-15, 17-30 are rejected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to TAYLOR V OH whose telephone number is (571)272-0689. The examiner can normally be reached 8:00-5:00.
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/TAYLOR V OH/Primary Examiner, Art Unit 1625 6/09/2026
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