DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claim Objections
Claim 13 is objected to because of the following informalities.
Claim 13: Applicant is suggested to amend “fatty acid esters of sorbitol or xylitol or erythritol” to state “fatty acid esters of sorbitol, [[or]] xylitol, or erythritol.” Applicant is also suggested to amend “organochlorine concentration” and “free fatty acid concentration” to state “an organochlorine concentration” and “a free fatty acid concentration,” respectively.
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 1-12 and 18-20 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.
Claims 1 and 18 each recite “mixing the FOG feedstock and a polyol in an esterification reactor to provide an esterification product.” The term “esterification” is a broad term encompassing various reactions that form an ester. For example, the most common esterification involves a reaction between a carboxylic acid (RCOOH) and an alcohol to produce an ester and water, but the esterification can also be performed with acid anhydride (RCOOCOR’) or acid chloride (RCOCl). It is further noted that the term esterification may also include transesterification, i.e. conversion of one ester into another via exchange of -OR group of an alcohol, and interesterification, i.e., rearrangement of the fatty acids of a fat product, such as a triglyceride. The recited limitation at issue is considered indefinite because the mere recitation of “to provide an esterification product” without specifying reactants and products of the reaction makes it unclear as to what is actually being reacted and produced in the esterification reactor.
The instant specification discloses:
The polyol reactant is used to convert the free fatty acids to fatty acid esters including polyesters. Examples of the fatty acid polyesters include mono-, di-, and tri-ester products of the reaction between the polyol and free fatty acids. The esterification reactions also include inter-esterifications whereby the bound fatty acids of the FOG form new esters with the polyol reactant. Without being bound to any particular theory, it is believed that the fatty acids that are part of the FOG feedstock in the form of fatty acid esters of MCPD migrate to form new esters with the polyol, thus releasing the MCPD for removal via water wash phase separation. Contacting the FOG with water at esterification temperatures accelerates the desired transformation by promoting hydrolysis of the MCPD esters. The esterification occurs in the absence of a catalyst.
Page 8, lines 9-19 (emphasis added).
The water vapor removal promotes the desired esterification reaction between the polyols and the FFAs, while the additional residence time promotes the interesterification reactions that allow for redistribution of fatty acids among the MCPD, native glycerol (e.g. from FOG glycerides), and added polyols, thus releasing the MCPD from the water insoluble ester forms to the free MCPD form which is soluble in water. A schematic of potential inter-esterification reactions is shown in FIG. 2. Referring to FIG. 2, the palmitic acid ester of 3-MCPD (Structure I) and glycerol (Structure II) undergo inter-esterification according to Eq. 1 to form water-soluble 3-MCPD (Structure III) and a palmitic acid monoglyceride (Structure IV). Similarly, a 3-MCPD di-ester of oleic acid and palmitic acid (Structure V) may undergo inter-esterification with xylitol (Structure VI) according to Eq 2 to from the same water-soluble 3-MCPD and a fatty acid di-ester of xylitol (Structure VII).
Page 12, lines 12-23 (emphasis added); see also Fig. 2.
As shown above, the specification explains that organochlorines, such as 3-monochloropropane-1,2,-diol (3-MCPD), are removed from the FOG feedstock by migrating the fatty acid chains from the FOG to polyol to form new esters, thereby releasing the chlorine-containing backbone portion which can be washed away with water. Furthermore, it is noted that what the specification describes as “inter-esterification” in in the description on page 12, lines 12-23 and in Fig. 2 is more commonly known as, or is also referred to as, transesterification, i.e., exchange of -OR group between an ester and an alcohol. For the purpose of examination, claims 1 and 18 are interpreted such that the claimed step of “mixing the FOG feedstock and a polyol in an esterification reactor to provide an esterification product” is conducted under reaction conditions effective for transesterifying organochlorine-containing FOG compounds with the polyol to produce unbound organochlorines, released from said FOG compounds, and fatty acid esters of the polyol, formed by reaction between fatty acids of said FOG compounds and the polyol.
Claims 2-12 and 19-20 are also rejected under 35 U.S.C. 112(b) by virtue of their dependency upon claims 1 and 18, respectively.
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.
The factual inquiries 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.
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.
Claims 1 and 5-8 are rejected under 35 U.S.C. 103 as being unpatentable over Hed et al. (US 2015/0166930 A1; cited in IDS dated 02/22/2024), as evidenced by Goodrich et al. (US 2018/0148665 A1).
Regarding claim 1, Hed discloses a process for lowering the amounts of esters of 2- and 3-MCPD in refined triglyceride oil, the process comprising
(a) mixing a refined triglyceride oil (a FOG feedstock) with glycerol (a polyol) and subjecting to a heat treatment in the presence of an aqueous base where interesterification may take place to degree of below 60% ([0005]-[0012]; [0048]);
(b) subjecting the reaction medium to steam stripping ([009]-[0012]; [0070]), which corresponds to water washing; and
(c) obtaining a treated stream containing a reduced content of organochlorines.
Hed does not teach that the triglyceride oil comprises an organochlorine content between 10 wppm and 50 wppm.
However, Hed discloses that its process is useful for processing refined triglyceride oils, where the concentration of 2- and 3-MCPD esters can be reduced by at least 50, e.g., at least 80%, relative to the initial concentration ([0041], [0062]; see also see Example 5 where the content of organochlorines (3-MCPD and 2-MCPD) is reduced by the heat treatment from 4.9 ppm to 0.9 ppm, a reduction of about 81.6%). It is known in the art that refined triglycerides oils may contain monochloropropanol and fatty acid esters thereof in an amount ranging from 0.01 ppm to 30 ppm, such as 1.5 ppm to 20 ppm, as evidenced by Goodrich ([0005], [0029]). Therefore, Hed is interpreted to be useful for triglycerides oils having an organochlorine content ranging from 0.01 ppm to 30 ppm, which overlaps and renders obvious the claimed initial organochlorine content range of “between 10 wppm and 50 wppm.” In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. MPEP 2144.05. I. The claimed final organochlorine content range of “less than 5 wppm” is also considered prima facie obvious, since Hed teaches that the concentration of MCPD compounds in the feedstock oils may be reduced by at least 80% relative to the initial concentration ([0062]).
With regard to the transesterification conditions, Hed teaches that the heat treatment is performed at a temperature between 120°C and 240°C and a reduced pressure between 1 and 100 mbar ([0021], [0025]). The temperature and pressure conditions taught by Hed overlap those of the instant disclosure (Spec., pg. 12, lines 6-11, “about 150 to about 280°C” and “0.1 psia and 7 psia”). Therefore, Hed is considered to teach that the heat treatment is conducted under conditions that overlap with those that are effective for transesterification of the FOG feedstock with a polyol (glycerol).
Regarding claim 5, Hed teaches that the heat treatment is performed at a temperature between 120°C and 240°C ([0021]). The claimed range of “between 150°C and 280°C” overlaps the temperature taught by Hed and is considered prima facie obvious.
Regarding claim 6, Hed teaches that the heat treatment is performed at a reduced pressure between 1 and 100 mbar ([0025]), which is equivalent to between 0.0145 and 1.450 psi. The clamed range of between “0.1 psia and 7 psia” overlaps the pressure range taught by Hed and is considered prima facie obvious.
Regarding claim 7, Hed teaches adding glycerol to the reaction mixture comprising triglyceride oil and aqueous base ([0048]), which suggests that the triglyceride oil (FOG feedstock) is contacted with water before mixing with the polyol (glycerol).
Regarding claim 8, Hed teaches adding glycerol to the feedstock prior to the heat treatment ([0048]).
Claims 10-12 and 18-20 are rejected under 35 U.S.C. 103 as being unpatentable over Hed et al. (US 2015/0166930 A1; cited in IDS dated 02/22/2024), as applied to claim 1, and further in view of Perego et al. (US 2009/0300970 A1).
Regarding claim 10, Hed teaches the method of claim 1, as discussed above.
Hed does not teach subjecting the treated FOG light phase to a hydrodeoxygenation process by contacting the treated FOG light phase with a hydrogen-rich treat gas to produce mixed hydrocarbons.
However, Brandvold teaches a process for producing a hydrocarbon fraction which can be used as diesel fuel or as a component of diesel fuel, the process comprising hydrodeoxygenating a mixture of a biological origin containing esters of fatty acids in the presence of hydrogen and a catalyst ([0011]-[0012], [0014]). Brandvold discloses that the esters of fatty acids are typically triglycerides of fatty acids, wherein the hydrocarbon chain of the fatty acid can contain from 12 to 24 carbon atoms ([0012]). It is noted that the triglyceride oil processed in the Hed process also has a carbon chain length mainly of C12-C24 ([0051]).
Therefore, before the effective filing date of the instant invention, it would have been obvious to one of ordinary skill in the art to modify Hed by subjecting the treated triglyceride oil (corresponding to the claimed treated FOG light phase) to hydrodeoxygenation by contacting said oil with hydrogen to produce mixed hydrocarbons, as taught by Perego, because (i) Hed teaches a process for producing a refined triglyceride oil having reduced amounts of organochlorines, (ii) Perego teaches a process for converting a triglyceride oil to hydrocarbons that can be used as fuel, and (iii) this involves application of a product from a known process as a feedstock to another known process to yield predictable results. Particularly, one would have been motivated to use MCPD-depleted triglyceride oils from Hed into a deoxygenation process, since chlorines are known to cause corrosion of the equipment, e.g., engine.
Regarding claim 11, Perego discloses that the hydrodeoxygenation produces normal paraffins with a range of carbon atoms, including C11- ([0078]). It is noted Perego further discloses subjecting a hydrodeoxygenation product to hydroisomerization, followed by fractionation into various fractions including a C4- fraction, a gasoline fraction, and a gas oil fraction ([0011], [0063]; see also Figs. 1 and 3). Perego notes the hydroisomerization product includes paraffins with carbon atoms ranging from 5 to 22 ([0080]). Since hydroisomerization does not change the carbon chain length, the hydrodeoxygenation product is considered to contain at least some hydrocarbons that have a boiling point corresponding to gasoline, including C5 and C6 paraffins.
Regarding claim 12, Perego discloses that the hydrodeoxygenation produces normal paraffins with a range of carbon atoms, including C11- ([0078]). It is noted Perego further discloses subjecting a hydrodeoxygenation product to hydroisomerization, followed by fractionation into various fractions including a C4- fraction, a gasoline fraction, and a gas oil fraction ([0011], [0063]; see also Figs. 1 and 3). Perego notes the hydroisomerization product includes paraffins with carbon atoms ranging from 5 to 22 ([0080]). Since hydroisomerization does not change the carbon chain length, the hydrodeoxygenation product is considered to contain at least some normal paraffins that have a boiling point corresponding to gasoline, including n-hexane.
Regarding claim 18, Hed discloses a process for lowering the amounts of esters of 2- and 3-MCPD in refined triglyceride oil, the process comprising
(a) mixing a refined triglyceride oil (a FOG feedstock) with glycerol (a polyol) and subjecting to a heat treatment in the presence of an aqueous base where interesterification may take place to degree of below 60% ([0005]-[0012]; [0048]);
(b) subjecting the reaction medium to steam stripping ([009]-[0012]; [0070]), which corresponds to water washing; and
(c) obtaining a treated stream containing a reduced content of organochlorines.
Hed does not teach that the triglyceride oil comprises an organochlorine content between 10 wppm and 50 wppm.
However, Hed discloses that its process is useful for processing refined triglyceride oils, where the concentration of 2- and 3-MCPD esters can be reduced by at least 50, e.g., at least 80%, relative to the initial concentration ([0041], [0062]; see also see Example 5 where the content of organochlorines (3-MCPD and 2-MCPD) is reduced by the heat treatment from 4.9 ppm to 0.9 ppm, a reduction of about 81.6%). It is known in the art that refined triglycerides oils may contain monochloropropanol and fatty acid esters thereof in an amount ranging from 0.01 ppm to 30 ppm, such as 1.5 ppm to 20 ppm, as evidenced by Goodrich ([0005], [0029]). Therefore, Hed is interpreted to be useful for triglycerides oils having an organochlorine content ranging from 0.01 ppm to 30 ppm, which overlaps and renders obvious the claimed initial organochlorine content range of “between 10 wppm and 50 wppm.” In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. MPEP 2144.05. I. The claimed final organochlorine content range of “less than 5 wppm” is also considered prima facie obvious, since Hed teaches that the concentration of MCPD compounds in the feedstock oils may be reduced by at least 80% relative to the initial concentration ([0062]).
With regard to the transesterification conditions, Hed teaches that the heat treatment is performed at a temperature between 120°C and 240°C and a reduced pressure between 1 and 100 mbar ([0021], [0025]). The temperature and pressure conditions taught by Hed overlap those of the instant disclosure (Spec., pg. 12, lines 6-11, “about 150 to about 280°C” and “0.1 psia and 7 psia”). Therefore, Hed is considered to teach that the heat treatment is conducted under conditions that overlap with those that are effective for transesterification of the FOG feedstock with a polyol (glycerol).
Hed does not teach subjecting the treated FOG light phase to a hydrodeoxygenation process by contacting the treated FOG light phase with a hydrogen-rich treat gas to produce mixed hydrocarbons.
However, Brandvold teaches a process for producing a hydrocarbon fraction which can be used as diesel fuel or as a component of diesel fuel, the process comprising hydrodeoxygenating a mixture of a biological origin containing esters of fatty acids in the presence of hydrogen and a catalyst ([0011]-[0012], [0014]). Brandvold discloses that the esters of fatty acids are typically triglycerides of fatty acids, wherein the hydrocarbon chain of the fatty acid can contain from 12 to 24 carbon atoms ([0012]). It is noted that the triglyceride oil processed in the Hed process also has a carbon chain length mainly of C12-C24 ([0051]).
Therefore, before the effective filing date of the instant invention, it would have been obvious to one of ordinary skill in the art to modify Hed by subjecting the treated triglyceride oil (corresponding to the claimed treated FOG light phase) to hydrodeoxygenation by contacting said oil with hydrogen to produce mixed hydrocarbons, as taught by Perego, because (i) Hed teaches a process for producing a refined triglyceride oil having reduced amounts of organochlorines, (ii) Perego teaches a process for converting a triglyceride oil to hydrocarbons that can be used as fuel, and (iii) this involves application of a product from a known process as a feedstock to another known process to yield predictable results. Particularly, one would have been motivated to use MCPD-depleted triglyceride oils from Hed into a deoxygenation process, since chlorines are known to cause corrosion of the equipment, e.g., engine.
Regarding claim 19, Perego further discloses subjecting a hydrodeoxygenation product to hydroisomerization, followed by fractionation into various fractions including a C4- fraction (including propane), a gasoline fraction, and a gas oil (diesel) fraction ([0011], [0063]; see also Figs. 1 and 3). The gasoline fraction and gas oil fraction correspond to C5-C11 hydrocarbons and C12+ hydrocarbons, respectively. Therefore, the gasoline fraction is considered to contain a C5/C6 fraction.
Regarding claim 20, Perego discloses that the hydrodeoxygenation produces paraffins with a range of carbon atoms, including a C11- fraction, a C12-20 fraction, and C20+ fraction ([0078]). Therefore, the hydrodeoxygenation is considered to produce hydrocarbons having a boiling point corresponding to gasoline or diesel.
Allowable Subject Matter
Claims 13-17 are allowable over prior art.
Claims 2-4 and 9 would be allowable if rewritten or amended 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.
The following is a statement of reasons for the indication of allowable subject matter. No prior art of record, individually or in combination, teaches or suggests a process for treating a FOG feedstock having an organochlorine content between 10 wppm and 50 wppm, the process comprising subjecting the FOG and a polyol to esterification to provide an esterification product comprising unbound organochlorine compounds and fatty acid esters of the polyol, water-washing the esterification product, and separating a treated FOG light phase from the water-washed product, wherein the FOG feedstock contains an FFA content greater than 5 wt% (claims 2-4), or the polyol is xylitol and/or sorbitol (claim 9). Hed et al. (US 2015/0166930 A1), applied in the above rejection, teaches adding free fatty acid in an amount of 0.1-3% ([0047]), but does not provide a reason to add free fatty acid in an amount greater than the suggested range. Furthermore, Hed only suggests adding glycerol to the reaction in order to control the degree of interesterification ([0048]), and fails to teach or suggest the use of xylitol and/or sorbitol as polyol reactant in the esterification to convert the organochlorine components to water-soluble species which can be subsequently removed by water-washing. Furthermore, no prior art of record teaches or reasonably suggests a composition comprising (a) fatty acid esters of sorbitol, xylitol, or erythritol, (b) fatty acid esters of glycerol, and (c) organochlorine concentration between 1 wppm and 5 wppm, as recited in claim 13.
Conclusion
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/JASON Y CHONG/Examiner, Art Unit 1772