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, 5, 6, 9, 10, and 12-20 are amended. Claim 11 is cancelled.
Claims 1-10 and 12-20 are pending for examination below.
Response to Arguments
Applicant's arguments filed 04 May 2026 have been fully considered but they are not persuasive.
Applicant argues on pages 13-15 of the Remarks that Morschbacker, Sarin, Coupard, and Verhaak do not teach step h) of the process.
In response, the Examiner agrees. As noted by Applicant, Vivien is cited to teach step h), and thus any argument that Morschbacker, Sarin, Coupard, and Verhaak do not teach the step h) is moot.
Applicant argues on pages 14-15 of the Remarks that Vivien does not teach the pressure range of step h), which is recited in the specification as making the compressed stream useful in forming superheated steam.
In response, the Examiner agrees that Vivien does not teach exactly the claimed pressure range, but Vivien teaches that the pressure of the steam streams can be adjusted to ensure sufficient pressure and ensure maximum heat recovery (paragraph [0078]), thus the pressure is taught by Vivien as optimizable. While the instant specification recites that the claimed pressure is useful for forming superheated steam in paragraph [0034], the instant specification does not provide any evidence that the pressure is critical. Vivien also forms superheated steam after the compression (paragraph [0079]), thus the pressure of Vivien must also be suitable for forming superheated steam. As such, Vivien continues to render obvious the claimed compressed steam pressure.
Claim Objections
Claims 1 and 20 are objected to because of the following informalities:
With regard to claims 1 and 20, claim 1 recites in step (f) and claim 20 recites in step (e) “the stream generator” which is a typographical error of “the steam generator”.
Appropriate correction is required.
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.
Claims 1, 3-10, 12, 13, 15, and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Morschbacker (US 2010/0069691) in view of Sarin et al. (US 2017/0266635, cited on IDS of 03/17/2025) and Vivien et al. (US 2017/0341996).
With regard to claim 1, Morschbacker teaches a process for producing ethylene comprising the following steps:
a) mixing ethanol and steam to form a mixture;
b) supplying the mixture to a dehydration reactor; and
c) dehydrating the ethanol to form a product stream comprising ethylene (paragraph [0102]).
Morschbacker does not specifically teach i) that the steam is superheated or ii) process steps d-g for generating the superheated steam stream.
With regard to i), Sarin teaches a process for ethanol dehydration (paragraph [0002]) comprising mixing a hot inert gas with a fresh ethanol feed before dehydration (paragraph [0011]) where the inert gas is steam (pargraph [0028]). Sarin further teaches that adding separate superheated steam to the ethanol allows for the process to avoid superheating ethanol, which causes thermal degradation, and also allows optimum utilization of the inert gas (paragraph [0040]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use superheated steam in the process of Morschbacker, because each of Morschbacker and Sarin teach ethanol dehydration to ethylene using steam, and Sarin teaches that superheated steam provides the benefits of avoiding ethanol degradation and optimum utilization of the inert gas (paragraph [0040]).
With regard to ii), Vivien teaches a process for dehydration of alcohols (paragraph [0001]) comprising the following steps:
c) dehydration of an alcohol to an olefin (paragraph [0019]).
d)-g) cooling the dehydration effluent against water in heat exchangers to form a vapor (steam) stream (steam generator) (paragraph [0020]).
h) compressing the vapor stream (paragraph [0078]).
g) superheating the vapor stream and recycling the vapor to the preheated feedstock (paragraphs [0079]-[0081]).
Vivien does not specifically teach i) the temperature of the effluent entering the heat exchanger is about 125 to about 140°C, ii) the pressure of the effluent entering the heat exchanger, iii) cooling the ethylene product stream below the dew point, iv) the temperature of the steam stream produced by heat exchange, v) the pressure of the steam stream produced by heat exchanger, or vi) the pressure of the compressed steam stream.
With regard to i), Vivien teaches the cooling step comprises three heat exchangers, one for generating steam, one for preheating the feedstock, and one using a heat exchange fluid, where the temperature starts at 250°C and is cooled to less than 50°C at the end of the heat exchangers (paragraphs [0065]-[0067]). While Vivien does not explicitly teach arranging the heat exchangers such that the effluent entering the heat exchanger which generates steam has the claimed temperature of about 125 to about 140°C as claimed, changing the order of the heat exchangers such that the effluent stream is cooled to about 125 to about 140°C before entering the heat exchanger for forming steam is merely a rearrangement of parts. It is held that rearrangement of parts is prima facie obvious absent evidence that the order is critical or changes the operation of the device (MPEP 2144.04(VI)C). The heat exchangers function to cool the effluent and heat various streams, and the function of the heat exchangers would be maintained if the heat exchangers were placed in a different order. Thus, the rearrangement is obvious, absent any evidence of criticality.
With regard to ii), Vivien teaches that the reactor pressure is 0.2 to 1 MPa (paragraph [0036]). Thus, the product stream from the reactor is also expected to be a pressure of 0.2 to 1 MPa, which overlaps the range of about 0.2 to about 0.3 of instant claim 1, rendering the range prima facie obvious.
With regard to iii), Vivien does not explicitly teach that the effluent is cooled below the ethylene dew point, however, Vivien teaches that the effluent is fully condensed (paragraph [0067]), thus the temperature is expected to be below the dew point of the ethylene product stream, absent any evidence to the contrary.
With regard to iv), Vivien teaches that the temperature of the compressed steam stream does not exceed 300°C (paragraph [0078]) and one of ordinary skill in the art understands that compressing the stream will increase both the temperature and pressure (instant specification paragraph [0034]). Thus, the steam stream before compression also has a temperature which does not exceed 300°C, which overlaps the range of about 95 to about 120°C of instant claim 1, rendering the range prima facie obvious.
With regard to v) and vi), Vivien further teaches that the pressure of the steam streams can be adjusted to ensure sufficient pressure in the dehydration step and also to ensure maximum recovery of the heat from the dehydration effluent (paragraph [0078]). Thus, the pressure of the steam stream before and after compression is a result-effective variable, and can be optimized. Therefore, it would have been obvious to one having ordinary skill in the art to have determined the optimum value of a pressure of the steam stream before compression of about 0.125 to about 0.2 MPa and after compression of about 0.3 to about 0.45 MPa, as claimed, because it has been held that discovering an optimum value of a result effective variable involves only routine skill in the art. See MPEP 2144.05(II).
Vivien further teaches the heating of the steam in the claimed manner limits thermal degradation of the feedstock and provides an overall reduction in the quantity of hot and cold utilities required for the dehydration process (paragraph [0015]). Vivien does not specifically teach that the process includes ethanol dehydration. However, all dehydration processes are endothermic processes. Further, the integration of steam generation with cooling the product stream would be expected to be effective for any dehydration feed, including the claimed ethanol feed, as the steam generation is not tied to what is in the product, but merely the temperature of the product, which as explained above would be expected to be similar for all dehydration processes. Thus, the process of Vivien is understood to be relevant prior art to the process of Morschbacker, as each reference teaches dehydration of alcohols in the presence of steam.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the steam generation steps of Vivien in the process of Morschbacker, because Morschbacker and Vivien each teach alcohol dehydration to olefins, and Vivien teaches that the heating of the steam in the claimed manner limits thermal degradation of the feedstock and provides an overall reduction in the quantity of hot and cold utilities required for the dehydration process (paragraph [0015]).
With regard to claims 3 and 4, Morschbacker teaches the reactor is a single fixed packed bed (single-stage) adiabatic reactor comprising gamma-alumina catalyst (paragraph [0102]).
With regard to claims 5, 10, and 12, Morschbacker teaches the feed mixture has a temperature of 470°C (paragraph [0102]), which is within the range of about 425 to about 500°C of instant claim 5 and the range of below about 480°C of instant claim 12. Morschbacker does not explicitly teach the temperature of the product. However, Morschbacker teaches the same ethanol and steam feed at the same temperature in the same single stage packed bed reactor comprising gamma-alumina. Thus, one of ordinary skill in the art would reasonably expect the effluent to have a similar temperature within the range of about 325 to 425°C of instant claims 5 and 10, absent any evidence to the contrary.
With regard to claim 6, Morschbacker teaches 62.2 tons ethanol to 135 tons steam (paragraph [0102]), which is a weight ratio of about 1:2, which is within the range of 1:1 to 1:5 of instant claim 6.
With regard to claim 7, Morschbacker does not explicitly teach the amount of ethylene in the product. However, Morschbacker teaches the same ethanol and steam feed at the same temperature in the same single stage packed bed reactor comprising gamma-alumina. Thus, one of ordinary skill in the art would reasonably expect the process to produce the similar amount of about 95 to about 99.5 mol% ethylene of instant claims 7 and 11, absent any evidence to the contrary.
With regard to claim 8, Vivien teaches preheating the alcohol feedstock by heat exchange with the dehydration effluent stream (paragraph [0027]).
With regard to claim 9, Vivien teaches that the temperature of the compressed stream does not exceed 300°C (paragraph [0078]), which overlaps the range of about 225°C to about 275°C of instant claim 9, rendering the range prima facie obvious.
With regard to claim 13, Vivian teaches that a suitable pressure for a dehydration feed comprising alcohols is 2 to 10 bar (0.2 to 1 MPa), which overlaps the range of 0.15 to 0.4 MPa of instant claim 13, rendering the range prima facie obvious.
With regard to claim 15, Morschbacker teaches the ethanol is produced from fermentation of agricultural products (paragraph [0101]), and thus the ethanol is bio-ethanol, as claimed.
With regard to claim 20, Morschbacker teaches a process for producing ethylene comprising the following steps:
a) mixing ethanol and steam to form a mixture (paragraph [0102]). The mixture has a temperature of 470°C and comprises 62.2 tons ethanol to 135 tons steam (paragraph [0102]), which is a weight ratio of about 1:2. These are within the ranges of 1:1 to 1:5 and about 425 to about 500°C of instant claim 20.
b) supplying the mixture to a dehydration reactor which is a single fixed packed bed (single-stage) adiabatic reactor comprising gamma-alumina catalyst (paragraph [0102]).
c) dehydrating the ethanol to form a product stream comprising ethylene (paragraph [0102]).
Morschbacker does not specifically teach i) that the steam is superheated, ii) the temperature of the ethylene product stream, or iii) process steps d-h for generating a steam stream.
With regard to i), Sarin teaches a process for ethanol dehydration (paragraph [0002]) comprising mixing a hot inert gas with a fresh ethanol feed before dehydration (paragraph [0011]) where the inert gas is steam (pargraph [0028]). Sarin further teaches that adding separate superheated steam to the ethanol allows for the process to avoid superheating ethanol, which causes thermal degradation, and also allows optimum utilization of the inert gas (paragraph [0040]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use superheated steam in the process of Morschbacker, because each of Morschbacker and Sarin teach ethanol dehydration to ethylene using steam, and Sarin teaches that superheated steam provides the benefits of avoiding ethanol degradation and optimum utilization of the inert gas (paragraph [0040]).
With regard to ii), Morschbacker teaches the same ethanol and steam feed at the same temperature in the same single stage packed bed reactor comprising gamma-alumina. Thus, one of ordinary skill in the art would reasonably expect the effluent to have a similar temperature within the range of about 325 to 425°C of instant claims 5 and 10, absent any evidence to the contrary.
With regard to iii), Vivien teaches a process for dehydration of alcohols (paragraph [0001]) comprising the following steps:
c) dehydration of an alcohol to an olefin (paragraph [0019]).
d)-g) cooling the dehydration effluent against water in heat exchangers to form a vapor (steam) stream (steam generator) (paragraph [0020]).
h) compressing the vapor stream (paragraph [0078]).
g) superheating the vapor stream and recycling the vapor to the preheated feedstock (paragraphs [0079]-[0081]).
Vivien does not specifically teach i) the temperature of the effluent entering the heat exchanger is about 125 to about 140°C, ii) the pressure of the effluent entering the heat exchanger, iii) cooling the ethylene product stream below the dew point, iv) the temperature of the steam stream produced by heat exchange, v) the pressure of the steam stream produced by heat exchanger, or vi) the pressure of the compressed steam stream.
With regard to i), Vivien teaches the cooling step comprises three heat exchangers, one for generating steam, one for preheating the feedstock, and one using a heat exchange fluid, where the temperature starts at 250°C and is cooled to less than 50°C at the end of the heat exchangers (paragraphs [0065]-[0067]). While Vivien does not explicitly teach arranging the heat exchangers such that the effluent entering the heat exchanger which generates steam has the claimed temperature of about 125 to about 140°C as claimed, changing the order of the heat exchangers such that the effluent stream is cooled to about 125 to about 140°C before entering the heat exchanger for forming steam is merely a rearrangement of parts. It is held that rearrangement of parts is prima facie obvious absent evidence that the order is critical or changes the operation of the device (MPEP 2144.04(VI)C). The heat exchangers function to cool the effluent and heat various streams, and the function of the heat exchangers would be maintained if the heat exchangers were placed in a different order. Thus, the rearrangement is obvious, absent any evidence of criticality.
With regard to ii), Vivien teaches that the reactor pressure is 0.2 to 1 MPa (paragraph [0036]). Thus, the product stream from the reactor is also expected to be a pressure of 0.2 to 1 MPa, which overlaps the range of about 0.2 to about 0.3 of instant claim 20, rendering the range prima facie obvious.
With regard to iii), Vivien does not explicitly teach that the effluent is cooled below the ethylene dew point, however, Vivien teaches that the effluent is fully condensed (paragraph [0067]), thus the temperature is expected to be below the dew point of the ethylene product stream, absent any evidence to the contrary.
With regard to iv), Vivien teaches that the temperature of the compressed steam stream does not exceed 300°C (paragraph [0078]) and one of ordinary skill in the art understands that compressing the stream will increase both the temperature and pressure (instant specification paragraph [0034]). Thus, the steam stream before compression also has a temperature which does not exceed 300°C, which overlaps the range of about 95 to about 120°C of instant claim 20, rendering the range prima facie obvious.
With regard to v) and vi), Vivien further teaches that the pressure of the steam streams can be adjusted to ensure sufficient pressure in the dehydration step and also to ensure maximum recovery of the heat from the dehydration effluent (paragraph [0078]). Thus, the pressure of the steam stream before and after compression is a result-effective variable, and can be optimized. Therefore, it would have been obvious to one having ordinary skill in the art to have determined the optimum value of a pressure of the steam stream before compression of about 0.125 to about 0.2 MPa and after compression of about 0.3 to about 0.45 MPa, as claimed, because it has been held that discovering an optimum value of a result effective variable involves only routine skill in the art. See MPEP 2144.05(II).
Vivien further teaches the heating of the steam in the claimed manner limits thermal degradation of the feedstock and provides an overall reduction in the quantity of hot and cold utilities required for the dehydration process (paragraph [0015]). Vivien does not specifically teach that the process includes ethanol dehydration. However, all dehydration processes are endothermic processes. Further, the integration of steam generation with cooling the product stream would be expected to be effective for any dehydration feed, including the claimed ethanol feed, as the steam generation is not tied to what is in the product, but merely the temperature of the product, which as explained above would be expected to be similar for all dehydration processes. Thus, the process of Vivien is understood to be relevant prior art to the process of Morschbacker, as each reference teaches dehydration of alcohols in the presence of steam.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the steam generation steps of Vivien in the process of Morschbacker, because Morschbacker and Vivien each teach alcohol dehydration to olefins, and Vivien teaches that the heating of the steam in the claimed manner limits thermal degradation of the feedstock and provides an overall reduction in the quantity of hot and cold utilities required for the dehydration process (paragraph [0015]).
Claims 2 and 14 are rejected under 35 U.S.C. 103 as being unpatentable over Morschbacker (US 2010/0069691) in view of Sarin et al. (US 2017/0266635) and Vivien et al. (US 2017/0341996) as applied to claim 1 above, and further in view of Coupard et al. (US 2015/0368215, cited on IDS 03/17/2025).
With regard to claim 2, Morschbacker in view of Vivien teaches the dehydration and steam generation process above. Morschbacker further teaches purification and separation to obtain the ethylene product (paragraph [0102]).
Morschbacker in view of Vivien fails to specifically teach flash separation of the product after steam generation.
Coupard teaches a process for dehydration of ethanol (paragraph [0011]). Coupard further teaches the process comprises separation of the product in a gas liquid separation zone (flash separation zone) to produce a liquid (condensate) and gas (vapor) stream (paragraph [0102]). Coupard additionally teaches that the gas liquid separation is a useful preliminary step for purification to produce the desired ethylene product (paragraph [0103]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to add the step of gas liquid (flash) separation to the process of Morschbacker in view of Vivien, because Morschbacker in view of Vivien and Coupard each teach ethanol dehydration to produce a product comprising ethylene, followed by separation and purification of the product to obtain the ethylene, Morschbacker is silent regarding the specific separation steps, and Coupard teaches that gas liquid (flash) separation is a known and useful step to obtain the desired purified ethylene product (paragraph [0103]).
With regard to claim 14, Morschbacker in view of Vivien teaches the dehydration and steam generation process above. Morschbacker further teaches purification to obtain the ethylene product and a separate impurities stream (paragraph [0102]) and Vivian further teaches cooling and condensing to separate impurities after heat exchange (steam generation) (paragraph [0069]).
Morschbacker in view of Vivien fails to specifically teach a caustic wash as the purification step to remove impurities after steam generation.
Coupard teaches a process for dehydration of ethanol (paragraph [0011]). Coupard further teaches the process comprises purification of the ethylene containing effluent by washing with sodium hydroxide (caustic wash) (paragraph [0104]). Coupard additionally teaches that purification is used to produce the desired ethylene product (paragraph [0103]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention use a caustic wash during the purification of Morschbacker in view of Vivien, because Morschbacker in view of Vivien and Coupard each teach ethanol dehydration to produce a product comprising ethylene, followed by purification of the product to obtain the ethylene, Morschbacker is silent regarding the specific purification step, and Coupard teaches that washing with sodium hydroxide (caustic) is a known purification step which is used to produce the desired ethylene product (paragraph [0104]).
Claims 16-19 are rejected under 35 U.S.C. 103 as being unpatentable over Morschbacker (US 2010/0069691) in view of Sarin et al. (US 2017/0266635) and Vivien et al. (US 2017/0341996) as applied to claim 1 above, and further in view of Verhaak et al. (US 2014/0018556).
With regard to claims 16-19, Morschbacker in view of Sarin and Vivien teaches the process above, which produces a product stream comprising ethylene. Vivien further teaches condensing the product stream after heat exchange (claimed steam generation) followed by distillation to obtain the vapor ethylene product (paragraphs [0069] and [0082]-[0083]).
Morschbacker in view of Sarin and Vivien does not specifically teach further reaction of the vapor ethylene product to produce ethylene oxide.
Verhaak teaches a process for production of ethylene oxide (paragraph [0001]). Verhaak teaches the process comprises contacting ethylene and oxygen over a catalyst having a silver content of 17.5 wt% (paragraph [0091]) in a fixed bed tubular reactor (paragraph [0092]) at a work rate of 195 kg/m3/hr at a temperature of 244°C (paragraph [0093]). These amounts are within the ranges of about 15 to about 40 wt% silver, about 130 to about 300 kg/m3/hm, and about 240 to about 280°C of instant claims 17-19. Verhaak further teaches that it is desired to transport natural gas components as liquids, and that ethylene oxide is used to synthesize monoethylene glycol, which is a transportable liquid derivative of natural gas (paragraphs [0002]-[0003]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the ethylene of Morschbacker in view of Sarin and Vivien in the process of Verhaak to synthesize ethylene oxide, because Morschbacker, Vivien, and Verhaak each teach producing ethylene from oxygenates (Verhaak paragraph [0037]) and Verhaak teaches that ethylene oxide is a desirable product which can be used to convert components of natural gas to liquid form for easier transportation (paragraphs [0002]-[0003]).
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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