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, 3, 12 are amended. Claims 19-20 are new.
The amendments to claims 1 and 12 overcome the claim objections and some of the 112(b) rejections, while the amendment to claim 3 creates new 112(b) issues, as recited in the rejection below.
The Examiner contacted Applicant’s representative on 28 April 2026 to propose an amendment to incorporate the specific Ru and ZrO2 containing catalyst of new claims 19 and 20 into the independent claims 1 and 12, with some other minor changes to dependent claims, in order to place the application in condition for allowance. However, Applicant’s representative respectfully declined the proposed amendment and requested an Office Action, which is provided herein.
Claims 1-20 are pending for examination below.
Terminal Disclaimer
The terminal disclaimer filed on 30 December 2025 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of any patent granted on Application 18/500,162 has been reviewed and is accepted. The terminal disclaimer has been recorded.
Response to Arguments
Applicant's arguments filed 30 December 2025 have been fully considered but they are not persuasive.
Applicant argues in the last paragraph on page 8 of the Remarks that Fichtl does not teach or suggest linear selective hydrocracking because Fichtl teaches producing fuels, not linear alkyl benzenes, and fuels do not require linear selective cracking.
In response, the Examiner respectfully disagrees. While Fichtl does teach forming fuels in an embodiment including isomerization and cracking (paragraph [0027]), Fichtl also states “In another embodiment…cracking can be conducted to crack normal paraffins that have higher chain lengths into paraffins that have lower carbon chain lengths, such as C9 to C15 normal paraffins.” (paragraph [0026]). Fichtl also explicitly teaches using normal paraffins from the deoxygenation for making linear alkyl benzenes (paragraph [0029]). Thus, because Fichtl explicitly desires making normal paraffins from the cracking in a distinct embodiment from the embodiment for making fuels, and also teaches using normal paraffins to make linear alkyl benzenes, one of ordinary skill in the art would reasonably conclude that the cracking of Fichtl is linear selective cracking, as claimed.
Applicant also argues in the last paragraph on page 8 of the Remarks that the cracking catalyst of Fichtl can contain acid functionality because the catalyst is not necessarily linear selective, whereas linear selective cracking catalysts contain minimal acid functionality.
In response, the claims do not require any limitations on the acid functionality of the claims, and Applicant has not provided any evidence that the acid functionality is critical to the linear selectivity of the catalyst. The instant specification has a few preferred catalysts which include metals on alumina supports (paragraph [0014]). The catalyst options of Fichtl include metals on alumina supports (paragraph [0027]). Thus, because Fichtl teaches cracking of heavy normal paraffins to produce lighter normal paraffins (paragraph [0026]) over similar catalysts (paragraph [0027]), the catalyst used in the cracking of Fichtl is understood to be a linear selective catalyst, as claimed, absent any evidence to the contrary.
Applicant argues in the first paragraph on page 9 of the Remarks that Fichtl does not specifically teach separating isoparaffins from normal paraffins in the cracking product because the product is used for fuels, which do not require separation.
In response, as noted above, Fichtl teaches fuels as a different embodiment from cracking to produce normal paraffins (paragraph [0026]), and also teaches using normal paraffins to make linear alkyl benzenes (paragraph [0029]). Thus, one of ordinary skill in the art would continue to find it obvious to separate the normal paraffins from the isoparaffins in the cracking product in order to use the normal paraffins to make linear alkyl benzenes, as taught by Fichtl and as claimed.
Applicant argues on page 9 of the Remarks that Fichtl does not teach the linear selective cracking be in a separate unit, as claimed.
In response, Fichtl states that a portion or all of the deoxygenation product can be sent to the cracking step (paragraph [0026]). The claims merely require that the unit for selective cracking be separate, which is understood as being separate from the deoxygenation step and/or the separating step, as these are the only steps required to come before the cracking step in claim 1. As Sohn teaches separation of the C14+ stream and Fichtl teaches that all or a portion of the deoxygenation effluent can be sent to the cracking, the cracking of Fichtl is understood as taking place in a separate reactor from the deoxygenation and separation, as claimed.
Applicant notes on page 9 of the Remarks that Frey does not remedy the deficiencies of Sohn and Fichtl.
In response, the Examiner agrees that Frey does not address the linear selective cracking, because Frey is used for the conditions of the deoxygenation step only. Thus, the argument is moot.
Claim Objections
Claims 1 and 12 are objected to because of the following informalities:
With regard to claim 1, the claim recites in line 9 “the presence”. This should be “a presence” for antecedent basis purposes.
Also with regard to claim 1, the claim recites in the last two lines “the alkylbenzene product”. This should be “the linear alkylbenzene product” for proper antecedent basis.
With regard to claim 12, the claim recites in line 9 “the presence”. This should be “a presence” for antecedent basis purposes.
Appropriate correction is required.
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.
Claims 3 and 12-20 are 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.
With regard to claim 3, the claim recites “wherein the linear selective cracking catalyst comprises ruthenium, platinum, nickel supported catalyst or mixtures thereof”. It is unclear which metals are supported and which parts are included in the recitation of “mixtures thereof” and the claim is indefinite.
For purposes of examination, the instant specification discloses multiple catalysts comprising a single metal and single support, including Ru/ZrO2, Pt-Al2O3, Ni-alumina, and NiOx/clay. Thus, it appears that the claim is trying to recite that the catalyst can comprise any one of the metals on a support, or a mixture of catalysts, each comprising a metal on a support. The Examiner suggests “wherein the linear selective cracking catalyst comprises a ruthenium-, platinum-, or nickel-supported catalyst, or mixtures thereof.”
With regard to claim 12, the claim recites the linear selective cracking catalyst "comprises ruthenium, platinum, and nickel supported catalyst or mixtures thereof." The claim as worded requires all three of ruthenium, platinum, and nickel, and so the phrasing of "or mixtures thereof" is indefinite as it is unclear how there can be any other mixtures.
For purposes of examination, the instant specification clearly contemplates catalysts which only have a single metal, such as ruthenium, and does not provide any examples of catalysts having all three metals (paragraph [0014]). The Examiner suggests similar wording as in the suggestion for claim 3 above, “wherein the linear selective cracking catalyst comprises a ruthenium-, platinum-, or nickel-supported catalyst, or mixtures thereof”.
With regard to claims 19 and 20, the claims recite that the linear selective catalyst comprises “Ru/ZrO2”. The use of the “/” causes a lack of clarity, because “/” is typically used to mean “and/or”, but it is clear from the instant specification that the catalyst is intended to comprise both Ru and ZrO2 (paragraph [0014]). Thus, claims 19 and 20 are indefinite.
For purposes of examination, as noted above, it is clear from the instant specification that the catalyst comprises both Ru and ZrO2 (paragraph [0014]). The Examiner suggests the wording “Ru-ZrO2” would fix the issue and match the options of Pt-Al2O3 and Ni-alumina also in paragraph [0014] of the instant specification.
With regard to claims 13-18, the claims are rejected as being dependent on a rejected base claim.
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 1-18 are rejected under 35 U.S.C. 103 as being unpatentable over Sohn et al. (US 2015/0361012, cited on IDS of 6/18/2024) in view of Frey et al. (US 2015/0148561) and Fichtl et al. (US 2014/0163278).
With regard to claims 1, 2, and 9, Sohn teaches a method for linear alkylbenzenes (paragraph [0001]) comprising the following steps (Figures 1, 2, and 4 and corresponding paragraphs [0017]-[0039]):
a) deoxygenating a natural oil feedstream to produce paraffin stream 115b (paragraph [0039], Figure 4) where the natural oil comprises triglycerides (paragraph [0020]).
b) combining the paraffin stream 115b with a paraffin stream from kerosene separator 118 to form a stream 116c which is passed to separator 122, which separates the stream as in Figure 1 (paragraph [0039]) and produces a heavy paraffin fraction 124 comprising C14+ paraffins and a light paraffin fraction 126 comprising “desired paraffins” (paragraph [0022]). It is expected that the C14+ stream 124 comprises C16 and C18 (instant claim 9), because Sohn teaches the stream 124 is produced by combining the deoxygenation stream with a stream from the kerosene separator and hydrotreater comprising paraffins, where the paraffin stream from the kerosene separator can comprise C9-C19 or even C20+ paraffins (paragraph [0018]). Sohn further teaches that the heavy paraffins are removed from the system in stream 124a (paragraph [0039]).
c) removing contaminants from the light paraffin fraction 126 in a purification stage (not shown in Figures), where the contaminants include oxygenates, nitrogen, and sulfur (paragraph [0024]).
d) dehydrogenating the purified paraffin stream 126 to produce a stream 32 comprising mono-olefins, di-olefins, and aromatics (paragraphs [0025]-[0026], Figure 2).
e) selectively hydrogenating the stream 32 to remove diolefins and produce a stream 40 comprising additional mono-olefins, where stream 40 is then separated into an aromatic stream and a mono-olefins stream 52 (paragraph [0028], Figure 2).
f) alkylating benzene with the mono-olefins stream 52 to produce a product comprising alkylbenzenes and benzene (paragraphs [0029]-[0030], Figure 2).
g) recovering the alkylbenzenes in stream 12 (paragraph [0033], Figure 2).
Sohn fails to teach i) that the deoxygenation produces 60 wt% or more normal paraffins having less than 16 carbon atoms; ii) that the light paraffin fraction 126 comprises specifically C9-C14 paraffins; iii) linear selective cracking of the C14+ heavy paraffins stream 124; or iv) removing contaminants from the product of the linear selective cracking (instant claim 1) by combining the C9 to C14 products of the cracking with the C9 to C14 products of the deoxygenation (instant claim 2).
With regard to the 60 wt% or more normal paraffins i), Sohn teaches that the natural oil feed can be coconut oil, babassu oil, Canola® oil, mustard oil, palm oil, palm kernel oil, soybean oil, or sunflower oil (paragraph [0019]), but is silent regarding the conditions of the deoxygenation. Thus, one of ordinary skill in the art would look to related deoxygenation processes to determine suitable conditions. Frey teaches a process for deoxygenation natural oils including coconut oil, babassu oil, palm kernel oil, and other vegetable, nut or seed oils (paragraph [0021] to produce C9 to C15 normal paraffins (paragraph [0018]). Frey further teaches that the deoxygenation conditions include a temperature of about 274 to about 371°C, a pressure of about 1724 kPa to about 5516 kPa, a space velocity of about 0.2 to 3 hr-1, a hydrogen to hydrocarbon molar ratio of 1500 to 8000 scf/b and a catalyst comprising nickel or nickel/molybdenum on an alumina, silica, titania, zirconia, or mixtures thereof support (paragraph [0025]). The instant specification recites deoxygenation of natural oils including coconut oil, babassu oil, canola oil, mustard oil, palm oil, palm kernel oil, soybean oil, or sunflower oil (paragraph [0010]) at conditions of about 1724 to about 5516 kPa, about 274 to about 371°C, 0.2 to 3 hr-1 space velocity, a hydrogen to hydrocarbon molar ratio of 1500 to 10,000 scfb, and a catalyst comprising Ni or Ni Mo on alumina, silica, titania, zirconia, or mixtures thereof (paragraph [0023]). The conditions of Frey are the same as or overlap the conditions in the instant specification, and Sohn in view of Frey teaches the same feeds and the same catalyst. Thus, one of ordinary skill in the art following the similar process of Sohn in view of Frey would reasonably expect the similar results of a product including 60 wt% or more C15- normal paraffins, as claimed, absent any evidence to the contrary.
With regard to the light paraffin fraction 126 contents ii), Sohn teaches above the light paraffin stream comprises “desired paraffins” and also that the paraffin stream is dehydrogenated to produce mono-olefins (paragraphs [0025]-[0026]). Sohn further teaches that a desirable olefin fraction for linear alkylbenzenes is selected to have a chain length of CL to CU, where L is an integer from 4 to 31 and U is an integer from 5 to 32 (paragraph [0035]). It is well understood by one of ordinary skill in the art that the paraffins are primarily dehydrogenated to olefins having the same carbon chain length. Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to select a desirable chain length of the olefins of C9 to C14, such that the paraffins would also have a desired chain length of C9 to C14, as claimed, because Sohn teaches dehydrogenating paraffins to olefins having a desired chain length, Sohn teaches the desired olefin chain length is in the range of C4 to C32, and one of ordinary skill in the art is able to select any integer within the range of Sohn without undue experimentation and with a reasonable expectation of success because Sohn teaches that any length within the range is suitable (paragraph [0035]).
With regard to the linear selective cracking iii), Fichtl teaches a method for producing normal paraffins having a desired chain length of C9 to C15 (paragraphs [0001] and [0004]). Fichtl teaches the process comprises functionalization of triglycerides by adding an OH group (paragraph [0005]), deoxygenation of the functionalized triglycerides to produce normal paraffins having the desired C9 to C15 chain length as well as some higher chain lengths (paragraph [0022]), and cracking the paraffins to convert the higher chain lengths into C9 to C15 normal paraffins (selective linear cracking) (paragraph [0026]). Fichtl also teaches that the process of cracking produces some isoparaffins (paragraph [0026]), and that the desired C9-C15 normal paraffins are used to produce linear alkylbenzenes (paragraph [0029]). Fichtl does not specifically teach separating the isoparaffins from the cracked products to form a stream comprising the normal paraffins and a stream comprising the isoparaffins. However, because Fichtl teaches using the normal paraffins stream in linear alkylbenzene synthesis (paragraph [0029]), one of ordinary skill in the art would find it obvious to separate the non-linear isoparaffins from the normal paraffins, in order to produce the desired linear alkylbenzenes from only the normal paraffins. Fichtl additionally teaches that the cracking can be done with less severe conditions which avoid the severe cracking conditions previously used to produce C9 to C15 paraffins (paragraph [0026]) where the severe conditions degrade the yield by cracking the desirable C9 to C15 paraffins (paragraph [0003]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to crack the C14+ paraffin stream of Sohn to produce additional C9 to C14 normal paraffins, as claimed, because Sohn and Fichtl each teach deoxygenation of triglyceride based feeds to produce normal paraffins having 9 to 14 carbon atoms along with some higher chain length paraffins, Sohn teaches separating and removing the C14+ heavy paraffin stream from the system, and Fichtl teaches that linear selective cracking of normal paraffins having longer chain lengths produces additional desirable C9 to C15 normal paraffins which are used in linear alkylbenzene synthesis, and avoids severe cracking conditions which decrease the yield of the desired normal paraffins in the C9 to C15 range (paragraph [0026]).
With regard to the removing contaminants from the first stream from the cracking iv), Sohn in view of Fichtl teaches producing the C9 to C14 normal paraffin stream from cracking the C14+ heavy paraffin stream, and Sohn teaches that the paraffin stream should be purified before dehydrogenation to produce olefins (paragraph [0024]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to combine the C9 to C14 paraffin stream from deoxygenation and the C9 to C15 paraffin stream from cracking and perform the purification (instant claim 2), because Fichtl teaches producing additional C9 to C14 paraffins which are useful in the process of Sohn, and Sohn teaches that such paraffins should be purified before dehydrogenation (paragraph [0024]).
With regard to claim 3, Fichtl teaches that the cracking catalyst is platinum on a support (paragraph [0027]).
With regard to claim 4, Fichtl teaches that the cracking conditions include a temperature of 150-360°C and a pressure of 1034 kPa to 4726 kPa (1.03 MPa to 4.73 MPa) (paragraph [0028]). These overlap the ranges of 290-455°C and 2.8 to 17.5 MPa of instant claim 4, rendering the ranges prima facie obvious.
With regard to claim 5, Sohn in view of Fichtl does not specifically teach that the amount of alkylbenzene is greater than if the process did not include the linear cracking step. However, the process of Sohn in view of Fichtl produces additional C9 to C14 paraffins which are used to make the alkylbenzene. Thus, one of ordinary skill in the art would expect that the additional C9 to C14 paraffin produced by the cracking would lead to additional alkylbenzene, as claimed.
With regard to claims 6-7, Sohn in view of Fichtl teaches that the olefins produced and used in the alkylation process can include C9 to C14 olefins (see ii) above). Thus, one of ordinary skill in the art would expect that the alkylbenzenes produced include C9 to C14 and C10 to C13 chains, respectively, as claimed.
With regard to claims 8, 10, and 11, as stated above, the conditions of Frey are the same as or overlap the conditions in the instant specification, and Sohn in view of Frey teaches the same feeds and the same catalyst. Thus, one of ordinary skill in the art following the similar process of Sohn in view of Frey would reasonably expect the similar results of a product including 0.1 to 20 wt% C16 normal paraffins (instant claim 8), at least 15 wt% C12 or C14 normal paraffins (instant claim 10), and at least 10 wt% C12 normal paraffins (instant claim 11), as claimed, absent any evidence to the contrary.
With regard to claims 12 and 13, Sohn teaches a method for linear alkylbenzenes (paragraph [0001]) comprising the following steps (Figures, 1, 2, and 4 and corresponding paragraphs [0017]-[0039]):
a) deoxygenating a natural oil feedstream to produce paraffin stream 115b (paragraph [0039], Figure 4) where the natural oil comprises triglycerides (paragraph [0020]).
b) combining the paraffin stream 115b with a paraffin stream from kerosene separator 118 to form a stream 116c which is passed to separator 122, which separates the stream as in Figure 1 (paragraph [0039]) and produces a heavy paraffin fraction 124 comprising C14+ paraffins and a light paraffin fraction 126 comprising “desired paraffins” (paragraph [0022]). Sohn further teaches that the heavy paraffins are removed from the system in stream 124a (paragraph [0039]).
c) removing contaminants from the stream 126 in a purification stage (not shown in Figures), where the contaminants include oxygenates, nitrogen, and sulfur (paragraph [0024]).
d) dehydrogenating the purified paraffin stream 126 to produce a stream 32 comprising mono-olefins, di-olefins, and aromatics (paragraphs [0025]-[0026], Figure 2).
e) selectively hydrogenating the stream 32 to remove diolefins and produce a stream 40 comprising additional mono-olefins, where stream 40 is then separated into an aromatic stream and a mono-olefins stream 52 (paragraph [0028], Figure 2).
f) alkylating benzene with the mono-olefins stream 52 to produce a product comprising alkylbenzenes and benzene (paragraphs [0029]-[0030], Figure 2).
g) recovering the alkylbenzenes in stream 12 (paragraph [0033], Figure 2). Sohn teaches that the olefins produced and used in the alkylation process can include C9 to C14 olefins (paragraph [0035]). Thus, one of ordinary skill in the art would expect that the alkylbenzenes produced include C9 to C14 chains as claimed.
Sohn fails to teach i) that the deoxygenation produces 60 wt% or more C15- normal paraffins (instant claim 12); ii) that the light paraffin fraction 126 comprises C9-C14 paraffins; iii) linear selective cracking of the C14+ heavy paraffins stream with a catalyst comprising platinum; or iv) removing contaminants from the product of the linear selective cracking by combining the C9 to C14 products of the cracking with the C9 to C14 products of the deoxygenation (instant claim 13).
With regard to the 60 wt% or more normal paraffins i), Sohn teaches that the natural oil feed can be coconut oil, babassu oil, Canola® oil, mustard oil, palm oil, palm kernel oil, soybean oil, or sunflower oil (paragraph [0019]), but is silent regarding the conditions of the deoxygenation. Thus, one of ordinary skill in the art would look to related deoxygenation processes to determine suitable conditions. Frey teaches a process for deoxygenation natural oils including coconut oil, babassu oil, palm kernel oil, and other vegetable, nut or seed oils (paragraph [0021] to produce C9 to C15 normal paraffins (paragraph [0018]). Frey further teaches that the deoxygenation conditions include a temperature of about 274 to about 371°C, a pressure of about 1724 kPa to about 5516 kPa, a space velocity of about 0.2 to 3 hr-1, a hydrogen to hydrocarbon molar ratio of 1500 to 8000 scf/b and a catalyst comprising nickel or nickel/molybdenum on an alumina, silica, titania, zirconia, or mixtures thereof support (paragraph [0025]). The instant specification recites deoxygenation of natural oils including coconut oil, babassu oil, canola oil, mustard oil, palm oil, palm kernel oil, soybean oil, or sunflower oil (paragraph [0010]) at conditions of about 1724 to about 5516 kPa, about 274 to about 371°C, 0.2 to 3 hr-1 space velocity, a hydrogen to hydrocarbon molar ratio of 1500 to 10,000 scfb, and a catalyst comprising Ni or Ni Mo on alumina, silica, titania, zirconia, or mixtures thereof (paragraph [0023]). The conditions of Frey are the same as or overlap the conditions in the instant specification, and Sohn in view of Frey teaches the same feeds and the same catalyst. Thus, one of ordinary skill in the art following the similar process of Sohn in view of Frey would reasonably expect the similar results of a product including 60 wt% or more C15- normal paraffins, as claimed, absent any evidence to the contrary.
With regard to the light paraffin fraction 126 contents ii), Sohn teaches above the light paraffin stream comprises “desired paraffins” and also that the paraffin stream is dehydrogenated to produce mono-olefins (paragraphs [0025]-[0026]). Sohn further teaches that a desirable olefin fraction for linear alkylbenzenes is selected to have a chain length of CL to CU, where L is an integer from 4 to 31 and U is an integer from 5 to 32 (paragraph [0035]). It is well understood by one of ordinary skill in the art that the paraffins are primarily dehydrogenated to olefins having the same carbon chain length. Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to select a desirable chain length of the olefins of C9 to C14, such that the paraffins would also have a desired chain length of C9 to C14, as claimed, because Sohn teaches dehydrogenating paraffins to olefins having a desired chain length, Sohn teaches the desired olefin chain length is in the range of C4 to C32, and one of ordinary skill in the art is able to select any integer within the range of Sohn without undue experimentation and with a reasonable expectation of success because Sohn teaches that any length within the range is suitable (paragraph [0035]).
With regard to the linear selective cracking iii), Fichtl teaches a method for producing normal paraffins having a desired chain length of C9 to C15 (paragraphs [0001] and [0004]). Fichtl teaches the process comprises functionalization of triglycerides by adding an OH group (paragraph [0005]), deoxygenation of the functionalized triglycerides to produce normal paraffins having the desired C9 to C15 chain length as well as some higher chain lengths (paragraph [0022]), and cracking the paraffins to convert the higher chain lengths into C9 to C15 normal paraffins (selective linear cracking) (paragraph [0026]). Fichtl also teaches that the process of cracking produces some isoparaffins (paragraph [0026]), and that the desired C9-C15 normal paraffins are used to produce linear alkylbenzenes (paragraph [0029]). Fichtl does not specifically teach separating the isoparaffins from the cracked products to form a stream comprising the normal paraffins and a stream comprising the isoparaffins. However, because Fichtl teaches using the normal paraffins stream in linear alkylbenzene synthesis (paragraph [0029]), one of ordinary skill in the art would find it obvious to separate the non-linear isoparaffins from the normal paraffins, in order to produce the desired linear alkylbenzenes from only the normal paraffins. Fichtl additionally teaches that the cracking can be done with less severe conditions which avoid the severe cracking conditions previously used to produce C9 to C15 paraffins (paragraph [0026]) where the severe conditions degrade the yield by cracking the desirable C9 to C15 paraffins (paragraph [0003]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to crack the C14+ paraffin stream of Sohn to produce additional C9 to C14 normal paraffins, as claimed, because Sohn and Fichtl each teach deoxygenation of triglyceride based feeds to produce normal paraffins having 9 to 14 carbon atoms along with some higher chain length paraffins, Sohn teaches separating and removing the C14+ heavy paraffin stream from the system, and Fichtl teaches that linear selective cracking of normal paraffins having longer chain lengths produces additional desirable C9 to C15 normal paraffins which are used in linear alkylbenzene synthesis, and avoids severe cracking conditions which decrease the yield of the desired normal paraffins in the C9 to C15 range (paragraph [0026]).
With regard to removal of contaminants by combining the streams iv), Sohn in view of Fichtl teaches producing the C9 to C14 normal paraffin stream from cracking the C14+ heavy paraffin stream, and Sohn teaches that the paraffin stream should be purified before dehydrogenation to produce olefins (paragraph [0024]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to combine the C9 to C14 paraffin stream from deoxygenation and the C9 to C15 paraffin stream from cracking and then perform the purification (instant claims 12 and 13), because Fichtl teaches producing additional C9 to C14 paraffins which are useful in the process of Sohn, and Sohn teaches that such paraffins should be purified before dehydrogenation (paragraph [0024]).
With regard to claim 14, Fichtl teaches that the cracking conditions include a temperature of 150-360°C and a pressure of 1034 kPa to 4726 kPa (1.03 MPa to 4.73 MPa) (paragraph [0028]). These overlap the ranges of 290-455°C and 2.8 to 17.5 MPa of instant claim 4, rendering the ranges prima facie obvious.
With regard to claim 15, Sohn in view of Fichtl does not specifically teach that the amount of alkylbenzene is greater than if the process did not include the linear cracking step. However, the process of Sohn in view of Fichtl produces additional C9 to C14 paraffins which are used to make the alkylbenzene. Thus, one of ordinary skill in the art would expect that the additional C9 to C14 paraffin produced by the cracking would lead to additional alkylbenzene, as claimed.
With regard to claims 16-18, as stated above, the conditions of Frey are the same as or overlap the conditions in the instant specification, and Sohn in view of Frey teaches the same feeds and the same catalyst. Thus, one of ordinary skill in the art following the similar process of Sohn in view of Frey would reasonably expect the similar results of a product including 0.1 to 20 wt% C16 normal paraffins (instant claim 16), at least 15 wt% C12 or C14 normal paraffins (instant claim 17), and at least 10 wt% C12 normal paraffins (instant claim 18), as claimed, absent any evidence to the contrary.
Allowable Subject Matter
Claims 19 and 20 would be allowable if rewritten to overcome the rejection(s) under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), 2nd paragraph, set forth in this Office action and to include all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter: The prior art of record does not teach or suggest using a catalyst comprising Ru-ZrO2 as the linear selective cracking catalyst.
The closest prior art is Fichtl et al. (US 2014/0163278) and Myers (US 3,046,317).
Fichtl teaches the linear selective cracking step described above, where the catalyst can be a metal of Group VIII on a support (paragraph [0027]), where Group VIII of the periodic table includes Ru. Fichtl further lists generally amorphous or crystalline supports, but only lists specific aluminum-containing supports (paragraph [0027]).
Fichtl does not contemplate a support comprising zirconia.
Myers teaches hydrocracking normal alkanes to preferentially produce normal hydrocarbons over a catalyst comprising a platinum group metal on a support, where the improvement comprises replacing the alumina in an alumina-boria support with zirconia (column 1, lines 11-19) where the platinum group metal is specified as being selected from the group consisting of Pt, Pd, Ir, and Rh (column 1, lines 33-34). Myers further teaches that the catalyst must comprise a support consisting essentially of zirconia and boria to provide the improvement (column 1, lines 61-66).
Therefore, while Myers teaches replacing alumina with zirconia in a support material for the similar cracking of normal alkanes to produce preferentially normal compounds, Myers only provides the motivation for replacing alumina in the specific support which consists essentially of alumina and boria (column 1, lines 61-66). Fichtl does not mention boria as a component of any of the aluminum containing supports, and Myers does not teach that Ru is a suitable metal for the catalyst. Thus, there is no teaching or suggestion that using zirconia in the support of Fichtl would be obvious or would produce the desired result of an increase in linear hydrocarbon compounds produced from the cracking, due to a lack of predictability in the catalyst art, and the claims would be allowable if the 112(b) rejection is overcome.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Girgis et al. (US 2023/0141033) teaches selective cracking of C12+ normal paraffins to C4-C13 normal paraffins over a catalyst comprising a Group VIIIA metal on zeolite (paragraphs [0025], [0028], and [0064]).
THIS ACTION IS MADE FINAL. 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.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, In Suk Bullock can be reached at 571-272-5954. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/Alyssa L Cepluch/Examiner, Art Unit 1772
/IN SUK C BULLOCK/Supervisory Patent Examiner, Art Unit 1772
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