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 .
DETAILED ACTION
Claims 1-8, 10-15, and 17-23 of V. Subramani et al., US 18/573,647 (Jun. 29, 2022) are pending. Claims 1-8, 10-12, and 17-23 are rejected. Claims 13-15 are objectionable.
Claim Objections
Claims 13-15 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Rejections 35 U.S.C. 112(b)
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.
Pursuant to 35 U.S.C. 112(b), the claim must apprise one of ordinary skill in the art of its scope so as to provide clear warning to others as to what constitutes infringement. MPEP 2173.02(II); Solomon v. Kimberly-Clark Corp., 216 F.3d 1372, 1379, 55 USPQ2d 1279, 1283 (Fed. Cir. 2000). A claim is indefinite when it contains words or phrases whose meaning is unclear. MPEP § 2173.05(e) (citing In re Packard, 751 F.3d 1307, 1314, 110 USPQ2d 1785, 1789 (Fed. Cir. 2014)).
Improper Preferences (Exemplary Claim Language)
Claim 6 is rejected under 35 U.S.C. 112(b) as being indefinite for recitation of exemplary claim language “such as”. MPEP § 2173.05(d).
6. The process of claim 1, wherein the chloride-containing organic compounds are selected from the group consisting of chlorine-substituted long-chain (C10+) paraffins, long-chain acid chlorides, chlorine-substituted long-chain aldehydes, chlorine-substituted long-chain ketones, cholesterol-like organic chlorides, and short-chain (C2-C9) diols such as 3-monochloropropane-1 ,2-diol or 2-monochloropropane-1,3-diol.
This claim 6 recitation of “such as”, in this context, improperly provide for preferences and thereby renders confusion over the intended scope of claim 6. See, MPEP § 2173.05(d).
Claim Rejections - 35 USC § 102 (AIA )
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
§ 102(a)(1) Rejection over F. Pudel et al., 113 Eur. J. Lipid Sci. Technol., 368-373 (2011) (“Pudel”)
Claims 1-8, 12 and 20-22 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by F. Pudel et al., 113 Eur. J. Lipid Sci. Technol., 368-373 (2011) (“Pudel”).
Pudel is directed to lowering the organic chlorides 3-chloropropane-1,2-diol (aka 3-MCPD) esters that occur during vegetable oil refining. Pudel at Abstract. Pudel’s organic chlorides 3-chloropropane-1,2-diol (aka 3-MCPD) and 3-chloropropane-1,2-diol-esters (aka 3-MCPD-E) are the same organic chlorides referenced in the instant specification. See, specification at page 6, [0020]-[0021]. For example, the specification teaches that, palm oil contains 3-monochloropropanediol (3-MPCD) as the primary chloride-containing organic compound. Specification at page 6, [0021]. The chloride impurities in vegetable oils arise from the environment. See, footnote 1 below.
In the portion relevant to the claims, Pudel teaches that crude palm oil was neutralized with potassium hydroxide and the soaps were separated, then the oil was washed with water until neutral pH reaction and afterwards subject to thermal treated. Pudel at page 371, col. 1.
Pudel teaches that if palm oil is neutralized with potassium hydroxide, the sample shows after thermal treatment a 45% lower content of 3-MCPD-E and related compounds than the not neutralized sample (Fig. 3). Pudel at page 371, col. 2; see also, Pudel Fig. 3. Pudel teaches:
Earlier investigations have shown that the content of FFA [free fatty acid] before deodorization does not influence the formation of 3- MCPD-E. Therefore it is assumed, that the washing steps during neutralization reduce the concentration of precursors of 3-MCPD-E/GE formation, e.g. chloride.
Pudel at page 371, col. 2.
Note that Pudel does not give the weight percent of potassium hydroxide employed or state the procedure detail, for example, whether or not the KOH was first dissolved before the treatment.
Pudel’s starting, raw palm oil contains, per claim 1, “a first chloride concentration by weight of chloride-containing organic compounds”. Raw vegetable oils, particularly palm oil, are known to contain organic chloride impurities (i.e., 3-chloropropane-1,2-diol aka 3-MCPD) that react during further processing to form the undesired chloroesters (i.e., 3-chloropropane-1,2-diol-esters aka 3-MCPD-E).1
Potassium hydroxide is a solid and meets meaning to the claim 1 term “solid treatment material”. With respect to the claim 1 term “solid treatment material”, the specification teaches:
[0033] The solid treatment material can be provided in a variety of forms, e.g., as a powder, or formed into extrudates or pellets. The person of ordinary skill in the art will appreciate that contacting the liquid feed with the solid treatment material can be performed in any desirable fashion, for example, using batch processing or continuous processing. For example, solid treatment material can be added directly to tt1e liquid feed in a reactor, or the liquid feed can be flowed through a bed of the solid treatment material, e.g., in one or more fixed bed reactors. The person of ordinary skill in the art can adapt conventional reactor processes and equipment to perform the processes described herein.
Specification at page 9, [0033].
Thus, Pudel meets the claim 1 limitation of:
Claim 1 . . . wherein the solid treatment material comprises potassium in ionic form in an amount of at least 2 wt%, based on the weight of the solid treatment material.
because Pudel employs KOH as a single component of the “solid treatment material” and so the amount of KOH is 100%, based on the weight of the solid treatment material.
In sum, Pudel contacts a “liquid feed that comprises one or more fatty acids and/or fatty acid esters, the liquid feed having a first chloride concentration by weight of chloride-containing organic compounds” (i.e., raw palm oil) with a solid treatment material (i.e., KOH), whereafter, the soaps were separated, then the oil was washed with water until neutral pH reaction, (Pudel at page 371, col. 1) so providing a treated palm oil feed corresponding to the claim 1 “treated liquid feed having a second chloride concentration”. Pudel then subjects each of the KOH-treated palm oil feed and the non-treated palm oil to separate thermal treatment, whereafter the treated feed had a 45% lower content of 3-MCPD-E and related compounds than the not neutralized sample. Pudel at page 371, col. 2; see also, Pudel Fig. 3. Pudel states that the washing steps during neutralization reduce the concentration of precursors of 3-MCPD-E/GE formation, e.g. chloride. Pudel at page 371, col. 2. Pudel thus meets each and every limitation of claim 1, which is therefore anticipated under 35 U.S.C. 102(a).
The further limitations of claim 2 are met by Pudel. Claim 2 requires “liquid feed includes at least 70 wt% renewable feedstock”. Pudel’s raw palm oil is clearly a renewable feedstock. See specification discussion of “renewable” at page 1. Furthermore, the term “renewable feedstock” is interpreted as product-by-process language because it defines the feedstock in terms of how it is obtained/prepared. MPEP § 2113(I). Even though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. MPEP § 2113(I); Biogen MA Inc. v. EMD Serono, Inc., 976 F.3d 1326, 1334 (Fed. Cir. 2020) (“[t]he nesting of the product-by-process limitation within a method . . . claim does not change the proper construction of the product-by-process limitation itself”); see also non-binding, non-precedential opinion in Ex parte Wohaibi, Appeal No. 2024-004112, 17/750,212 (PTAB 2025) discussing this Federal Circuit decision.
The further limitation of claim 3 and 4 are met because the palm oil employed by Pudel includes 94.6% mono-, di- and tri-glycerides (fatty acid esters) and 5% free fatty acids. Pudel at page 370, col. 2 (Table 1). This clearly meets the claim 3 recitation of “includes at least 70 wt% fatty acids and/or fatty acid esters”. Respecting claim 4, Pudel’s ratio of fatty acids to fatty acid esters (5:94.6) clearly falls within the claim 4 range of “wherein the ratio of fatty acids to fatty acid esters in the liquid feed is in the range of 0: to 1: 1”. Note that this is the typical composition of raw palm oil. See US 2014/0303389 (2014), page 4, [0014]-[0015] (Table A). Note also that the instant specification also employs palm oil in the working examples.
Per above, the further limitations of claim 5 are clearly met.
The limitations of claim 6 are met because the organic chlorides addressed and lowered by Pudel (i.e., 3-chloropropane-1,2-diol (aka 3-MCPD) and 3-chloropropane-1,2-diol-esters (aka 3-MCPD-E)) are, per claim 6, “short-chain (C2-C9) diols such as 3-monochloropropane-1 ,2-diol”.
Respecting claims 7 and 8, Pudel does not teach the chloride ppmw (part per million by weight) concentration in the untreated palm oil employed before either thermal-only or KOH treatment. The specification teaches that the palm oil employed in the working examples had an initial chloride concentration of 7.4 ppmw. Specification at page 14, Table A. However, the specification does not identify the palm oil’s source. It appears that Pudel’s palm oil is the same palm oil taught and used in the instant specification. As such, subject to Applicant’s rebuttal, Pudel’s raw palm oil employed before KOH treatment is asserted to meet the claim 7 and 8 ppmw chloride concentrations. Once a reference teaching product appearing to be substantially identical is made the basis of a rejection, and the examiner presents evidence or reasoning to show inherency, the burden of production shifts to the applicant. MPEP § 2112(V) (citing In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433-34 (CCPA 1977).
The limitations of claim 12 are clearly met.
The limitations of claim 20 are met because Pudel teaches that the concentration of 3-MCPD-E and related compounds after treatment with KOH is a bit over 3 ppm. Pudel at page 371, col. 2, Figure 3. This meets the claim 20 limitation of “wherein the process is performed for a time and under conditions such that the second chloride concentration is no more than 5 ppmw”.
Respecting claim 21 (as discussed above for claims 7 and 8) Pudel’s raw palm oil employed before KOH treatment is asserted, subject to Applicant’s rebuttal, to have the same chloride concentration of 7.4 ppmw as that of the specification working examples. Specification at page 14, Table A. Pudel teaches that the concentration of 3-MCPD-E and related compounds after treatment with KOH is a bit over 3 ppm (about 3.1 ppm). Pudel at page 371, col. 2, Figure 3. This meets the claim 21 limitation of “wherein the process is performed for a time and under conditions such that the second chloride concentration is no more than 50% of the first chloride concentration” because 3.1 ppm is no more than 50% of 7.4 ppmw.
The limitations of claim 22 are met because Pudel teaches that crude palm oil was neutralized with potassium hydroxide and the soaps were separated, then the oil was washed with water until neutral pH reaction. Pudel at page 371, col. 1.
§ 102(a)(1) Rejection over H. Hirai et al., EP3556833A1 (2019) (“Hirai”)
Claims 1-8, 10-12, and 17-21 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by H. Hirai et al., EP3556833A1 (2019) (“Hirai”).
Hirai teaches bringing a glyceride composition which has not undergone a deodorizing step into contact with a mixture containing clay and potassium carbonate suppresses the generation of 3-chloropropane-1,2-diol and fatty acid esters of 3-chloropropane-1,2-diol in a refined glyceride composition, reducing their content. Hirai at page 2, [0008].2
Hirai teaches that examples of the glyceride composition include vegetable oils the listing of which includes palm oil. Hirai at page 4, [0015]. Hirai teaches:
Here, the glyceride composition mentioned in the present invention includes glycerides formed by ester bonding glycerin with 1 to 3 fatty acids, and includes triglycerides (triacylglycerols) which are a major component of fat and/or oil as well as diglycerides (diacylglycerols) and monoglycerides (monoacylglycerols).
In addition, it may contain components other than glycerides derived from animal and plant fats and/or oils such as plant sterols, lecithin, antioxidant components, and pigment components.
However, it is appropriate that a content of 95% by mass or more is preferably of glyceride, and the glyceride is more preferably 97% by mass or more, further preferably 99% by mass or more, and particularly preferably 100% by mass. Note that it is appropriate that the triglyceride in the glyceride is preferably 90% by mass or more and more preferably 93% by mass to 100% by mass.
Hirai at page 4, [0015] (emphasis added).
With respect to the clay composition, Hirai teaches:
The alkaline clay used in the present invention is not particularly limited. However, for example, it is possible to use one having the following composition (unit: % by mass relative to the total amount of the alkaline clay).
SiO2 (50 to 60% by mass)
Al2O3 (10 to 20% by mass)
Fe2O3 (3 to 10% by mass)
MgO (2 to 9% by mass)
CaO (1 to 5% by mass)
Hirai at page 5, [0021] (emphasis added). With respect to the amount of potassium carbonate, Hirai teaches a clay treatment step using potassium carbonate together with the clay, where the content of potassium carbonate is, for example, 0.01% by mass or more, preferably 0.05% by mass or more, more preferably 0.1% by mass or more, further preferably 0.2% by mass or more, and particularly preferably 0.3% by mass or more and 10% by mass or less. Hirai at page 5, [0023].
Hirai teaches that contacting the glyceride composition with the clay/K2CO3 reduces the residual amount chlorine compounds in the following excerpt:
[0038] If the glyceride composition is brought into contact with the mixture containing clay and potassium carbonate in the first decolorizing step (the above clay treatment step) before the re-decolorizing step, the residual amount of the chlorine compounds considered to be the causative substances of 3-MCPD in the refined glyceride composition is sufficiently reduced. Therefore, regardless of the type of clay used in the re-decolorizing step, it is possible to significantly reduce the amount of 3-MCPD which may be generated in the re-deodorizing step after the re-decolorizing step.
Hirai at page 7, [0038]. In working Example 1, Hirai teaches that degummed palm crude oil was treated with a mixture of 200 mg alkaline clay and 10 mg of potassium carbonate (per claim 1 the K2CO3, which is solid, is at least 2wt percent based on the weight of the solid treatment material) followed by stirring at 90°C for 20 minutes and the resultant composition after contact was filtered through filter paper to obtain a refined glyceride composition (refined palm oil). Hirai at page 8, [0046]. Hirai teaches the amount of 3-chloropropane-1,2-diol (3-MCPD) in the filtered composition is 0.85 ppm. Hirai at page 9, Table 1 (see, Table 1, column labelled “3-MCPD Conversion Amount Before Heating at 250°C”).
Hirai’s Example 1 refined palm oil prepared by contacting degummed palm crude oil with clay/K2CO3 meets the claim 1 limitation of:
Claim 1 . . . providing a liquid feed that comprises one or more fatty acids and/or fatty acid esters, the liquid feed having a first chloride concentration by weight of chloride-containing organic compounds; and
contacting the liquid feed with a solid treatment material to remove at least a fraction of the chloride-containing organic compounds
to produce a treated liquid feed having a second chloride concentration that is less than the first chloride concentration,
wherein the solid treatment material comprises potassium in ionic form in an amount of at least 2 wt%, based on the weight of the solid treatment material.
because Hirai teaches the above claim 1 contacting steps and Hirai’s refined palm oil (the claim 1 “treated liquid feed”) has per claim 1, “a second chloride concentration that is less than the first chloride concentration” because this is what Hirai teaches per Hirai paragraph [0038] as cited above. Hira thus meets each and every limitation of claim 1, which is anticipated.
The further limitations of claim 2 are met by Hirai. Claim 2 requires “liquid feed includes at least 70 wt% renewable feedstock”. Hirai’s degummed palm oil is clearly a renewable feedstock. See specification discussion of “renewable” at page 1.
The further limitation of claim 3 and 4 are met because the degummed palm oil employed by Hirai would necessarily be a majority of mono-, di- and tri-glycerides (fatty acid esters) (about 99%) and a small amount of free fatty acids (1-5%). This is because raw palm oil is known to be composed of a majority mono-, di- and tri-glycerides (fatty acid esters) (about 99%) and a small amount of free fatty acids (1-5%). See, US 2014/0303389 (2014) at page 2, [0014]-[0015]. Degumming only removes gums (hydratable and nonhydratable phospholipids) and other phosphorus-containing compounds. See, S. Oey et al., Comprehensive reviews in Food Science Chemistry, 1-13 (2019) (at page 2, col. 2).
Per above, the further limitations of claim 5 are clearly met.
The limitations of claim 6 are met because the organic chlorides addressed and lowered by Hirai (i.e., 3-chloropropane-1,2-diol (aka 3-MCPD) and 3-chloropropane-1,2-diol-esters (aka 3-MCPD-E)) are, per claim 6, “short-chain (C2-C9) diols such as 3-monochloropropane-1 ,2-diol”.
Respecting claims 7 and 8, Hirai does not teach the chloride ppmw (part per million by weight) concentration in the untreated palm oil employed before either thermal-only or K2CO3/clay treatment. The specification teaches that the palm oil employed in the working examples had an initial chloride concentration of 7.4 ppmw. Specification at page 14, Table A. However, the specification does not identify the palm oil’s source. It appears that Hirai’s palm oil is the same palm oil taught and used in the instant specification. As such, subject to Applicant’s rebuttal, Hirai’s degummed palm oil employed before K2CO3/clay treatment is asserted to meet the claim 7 and 8 ppmw chloride concentrations. Once a reference teaching product appearing to be substantially identical is made the basis of a rejection, and the examiner presents evidence or reasoning to show inherency, the burden of production shifts to the applicant. MPEP § 2112(V) (citing In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433-34 (CCPA 1977).
The limitations of claim 10 are met for the following reasons. Claim 10 recites “wherein the solid treatment material comprises potassium in ionic form disposed on a support”. The specification does not define the term “disposed on a support”. See e.g., specification at page 7. [0027]. The specification teaches that “[t]he solid treatment material can be provided in a variety of forms, e.g., as a powder, or formed into extrudates or pellets”. Specification at page 9, [0033]. Thus, the broadest reasonable interpretation of “disposed on a support”, consistent with the plain meaning of “disposed on” and the specification, is that potassium, in ionic form, is in contact with the support. MPEP § 2111. In working Example 1, as cited above, Hirai teaches the following addition sequence:
[0046] . . . After the stirring, the resultant degummed glyceride composition (degummed palm crude oil) was added further with 200 mg (2% by mass relative to the entire degummed palm crude oil) of alkaline clay (manufactured by Natural Bleach SDN. BHD, NB 14000, pH = 8.6) and 10 mg (0.1% by mass relative to the entire degummed palm crude oil) of potassium carbonate, followed by stirring at 90°C for 20 minutes to bring the degummed glyceride composition (degummed palm crude oil) into contact with the mixture of clay and potassium carbonate.
Hirai at page 8, [0046] (emphasis added). It is not clear from [0046] whether Hirai adds the alkaline clay and potassium carbonate as an in-contact mixture or they are added as separate portions. However, even if a separate-portion addition is argued, still these two constituents will be in contact with each other in the stirred mixture and thereby meet the claim 10 limitation of “wherein the solid treatment material comprises potassium in ionic form disposed on a support”.
The limitations of claim 11 are met because the clay employed by Hirai comprises Al2O3 (alumina) and SiO2 (silica or silicate) and thus meets the plain meaning of “aluminosilicate”. Hirai at page 5, [0021]. The specification provides no discussion or guidance regarding the meaning of aluminosilicate. See e.g., specification at page 8, [0030]. See, O. Ombaka, 10 African Journal of Environmental Science and Technology, 415-431 (2016) (at page 415, col. 2 “[c]lay minerals are generally composed of aluminum silicates which are formed by tetrahedral and octahedral sheets that are linked together through sharing of apical oxygen atoms”).
The limitations of claim 12 are clearly met.
The limitations of claims 17-19 are met because in Example 1, Hirai teaches 200 mg of alkaline clay and 10 mg of potassium carbonate (total solid treatment material is 210 mg) to treat about 100g of degummed palm oil (so the solid treatment material is present in about 2.1% of the liquid feed) and heats the mixture to 90 °C for twenty minutes.
The limitations of claim 20 are met because Hirai teaches that the amount of 3-chloropropane-1,2-diol (3-MCPD) in the filtered composition is 0.85 ppm. Hirai at page 9, Table 1 (see, Table 1, column labelled “3-MCPD Conversion Amount Before Heating at 250°C”), which meets the claim 20 limitation of “wherein the process is performed for a time and under conditions such that the second chloride concentration is no more than 5 ppmw”.
Respecting claim 21 (as discussed above for claims 7 and 8) Hirai’s degummed palm oil employed before K2CO3/clay treatment is asserted, subject to Applicant’s rebuttal, to have about the same chloride concentration of 7.4 ppmw as that of the specification working examples. Specification at page 14, Table A. Hirai teaches that the concentration of 3-MCPD after K2CO3/clay treatment is 0.85 ppm. Hirai at page 9, Table 1 (see, Table 1, column labelled “3-MCPD Conversion Amount Before Heating at 250°C”). This meets the claim 21 limitation of “wherein the process is performed for a time and under conditions such that the second chloride concentration is no more than 50% of the first chloride concentration” because 0.85 ppm is no more than 50% of 7.4 ppmw.
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 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 AIA 35 U.S.C. 103(a) 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.
§ 103 REJECTION OF CLAIM 23
Claim 23 is rejected under AIA 35 U.S.C. 103 as being unpatentable over either of F. Pudel et al., 113 Eur. J. Lipid Sci. Technol., 368-373 (2011) (“Pudel”) or H. Hirai et al., EP3556833A1 (2019) (“Hirai”) in further view of L. Li et al., US 11,466,230 (2022) (“Li”).
F. Pudel et al., 113 Eur. J. Lipid Sci. Technol., 368-373 (2011) (“Pudel”)
Pudel was discussed in detail above in the § 102 rejection of claim 1. Pudel contacts a “liquid feed that comprises one or more fatty acids and/or fatty acid esters, the liquid feed having a first chloride concentration by weight of chloride-containing organic compounds” (i.e., raw palm oil) with a solid treatment material (i.e., KOH), whereafter, the soaps were separated, then the oil was washed with water until neutral pH reaction, (Pudel at page 371, col. 1) so providing a treated palm oil feed corresponding to the claim 1 “treated liquid feed having a second chloride concentration”. Pudel then subjects each of the KOH-treated palm oil feed and the non-treated palm oil to separate thermal treatment, whereafter the treated feed had a 45% lower content of 3-MCPD-E and related compounds than the not neutralized sample. Pudel at page 371, col. 2; see also, Pudel Fig. 3. Pudel states that the washing steps during neutralization reduce the concentration of precursors of 3-MCPD-E/GE formation, e.g. chloride. Pudel at page 371, col. 2. Pudel thus meets each and every limitation of claim 1.
H. Hirai et al., EP3556833A1 (2019) (“Hirai”)
Hirai was discussed in detail above in the § 102 rejection of claim 1. Hirai teaches bringing a glyceride composition which has not undergone a deodorizing step into contact with a mixture containing clay and potassium carbonate suppresses the generation of 3-chloropropane-1,2-diol and fatty acid esters of 3-chloropropane-1,2-diol in a refined glyceride composition, reducing their content. Hirai at page 2, [0008].
In working Example 1, Hirai teaches that degummed palm crude oil was treated with a mixture of 200 mg alkaline clay and 10 mg of potassium carbonate (per claim 1 the K2CO3, which is solid, is at least 2wt percent based on the weight of the solid treatment material) followed by stirring at 90°C for 20 minutes and the resultant composition after contact was filtered through filter paper to obtain a refined glyceride composition (refined palm oil). Hirai at page 8, [0046]. Hirai teaches the amount of 3-chloropropane-1,2-diol (3-MCPD) in the filtered composition is 0.85 ppm. Hirai at page 9, Table 1 (see, Table 1, column labelled “3-MCPD Conversion Amount Before Heating at 250°C”).
Differences between Pudel and Claim 23
Respecting claim 23, Both of Pudel and Hirai teach methods of preparing low-organic-chloride-content palm oil streams, which methods meet each and every limitation of claim 1. However, neither Pudel nor Hirai teach hydroprocessing the low-organic-chloride-content palm oil, as required by claim 23.
L. Li et al., US 11,466,230 (2022) (“Li”)
Li teaches that biofuels are typically manufactured from feedstock originating from renewable sources including oils and fats obtained from plants and animals, and these feedstocks, particularly the various waste streams and side streams, contain varying amounts of contaminants, such as organic chloride compounds which are, for example, deleterious to converting catalysts. Li at col. 1, lines 20-27.
Li teaches a process for removing organic chlorides from a glyceride oil to form a treated glyceride oil, wherein the treated glyceride oil has a reduced concentration of organic chlorides. Li at col. 1, lines 38-46.
Li teaches that suitable glyceride oils include palm oil. Li at col. 2, lines 39-46.
Li teaches that the treated glyceride oil, having low content of organic chloride compounds, is particularly suitable as feedstock for catalytic hydroprocessing, where equipment fouling and catalyst poisoning and inactivation can be avoided. Li at col. 5, lines 50-55.
Obviousness Rationale
Claim 23 is obvious because one of ordinary skill is motivated by Li to hydroprocess either of the low-organic-chloride-content palm oil streams of Pudel or Hirai to form a biofuel because Li teaches that such low-organic-chloride-content vegetable oil streams are particular suitable as feedstock for catalytic hydroprocessing, where equipment fouling and catalyst poisoning and inactivation can be avoided.
§ 103 REJECTION OF CLAIMS 10-12
Claims 10-12 are rejected under AIA 35 U.S.C. 103 as being unpatentable over H. Hirai et al., EP3556833A1 (2019) (“Hirai”) alone.
H. Hirai et al., EP3556833A1 (2019) (“Hirai”)
Hirai was discussed in detail above. In working Example 1, as cited above, Hirai teaches the following addition sequence:
[0046] . . . After the stirring, the resultant degummed glyceride composition (degummed palm crude oil) was added further with 200 mg (2% by mass relative to the entire degummed palm crude oil) of alkaline clay (manufactured by Natural Bleach SDN. BHD, NB 14000, pH = 8.6) and 10 mg (0.1% by mass relative to the entire degummed palm crude oil) of potassium carbonate, followed by stirring at 90°C for 20 minutes to bring the degummed glyceride composition (degummed palm crude oil) into contact with the mixture of clay and potassium carbonate.
Hirai at page 8, [0046] (emphasis added). Per above ¶ [0046], it is not clear whether Hirai adds the alkaline clay and potassium carbonate (K2CO3/clay) as an in-contact mixture (i.e., the K2CO3 is “disposed on” the clay support) or they are added as separate portions.
In the specification body, Hirai teaches the following respecting the K2CO3/clay mixture.
[0024] The mixture containing clay and potassium carbonate used in the present invention may be any mixture as long as it contains the clay and potassium carbonate described above and does not impair their activities. The mixture of the present invention can contain the clay and potassium carbonate as well as activated carbon, silica, and the like.
Hirai at page 6, [0024].
Differences between the Hirai and Claims 10-12
Base claim 10 differs from Hirai in that it is not clear from Hirai Example 1 (i.e., ¶ [0046] cited above) whether Hirai adds the alkaline clay and potassium carbonate (K2CO3/clay) as an in-contact mixture (i.e., the K2CO3 is “disposed on” the clay support) or they are added as separate portions. Thus, prior to the K2CO3/clay addition it is not clear whether Hirai’s K2CO3 is disposed on the clay, before the addition, and thus meets the claim 10 limitation of “wherein the solid treatment material comprises potassium in ionic form disposed on a support”.
Obviousness Rationale
The specification does not define the term “disposed on a support”. See e.g., specification at page 7. [0027]. The specification teaches that “[t]he solid treatment material can be provided in a variety of forms, e.g., as a powder, or formed into extrudates or pellets”. Specification at page 9, [0033]. Thus, the broadest reasonable interpretation of “disposed on a support”, consistent with the plain meaning of “disposed on” and the specification, is that potassium, in ionic form, is in contact with the support. MPEP § 2111.
Base claim 10 is obvious in view of Hirai Example 1 because one of ordinary skill is motivated to mix the K2CO3 with the claim before addition to the degummed palm crude oil, simply as a convenient method of addition or as a convention method of selling or transporting the mixture for future additions. In such circumstances, the K2CO3 is “disposed on” the clay and each and every limitation of base claim 10 is met. In this regard, Hirai alludes to the K2CO3/clay as a pre-addition mixture. Hirai at page 6, [0024] (“in the present invention may be any mixture as long as it contains the clay and potassium carbonate described above”).
The limitations of claim 11 are met because the clay employed by Hirai comprises Al2O3 (alumina) and SiO2 (silica or silicate) and thus meets the plain meaning of “aluminosilicate”. Hirai at page 5, [0021]. The specification provides no discussion or guidance regarding the meaning of aluminosilicate. See e.g., specification at page 8, [0030]. See, O. Ombaka, 10 African Journal of Environmental Science and Technology, 415-431 (2016) (at page 415, col. 2 “[c]lay minerals are generally composed of aluminum silicates which are formed by tetrahedral and octahedral sheets that are linked together through sharing of apical oxygen atoms”).
The limitations of claim 12 are clearly met.
Subject Matter Free of the Art of Record
Claims 13-15 are free of the art of record. These claims are directed to specific “solid treatment materials” to process the claim 1 “a liquid feed that comprises one or more fatty acids and/or fatty acid esters” so as “to produce a treated liquid feed having a second chloride concentration that is less than the first chloride concentration”.
13. The process of claim 1, wherein the solid treatment material is an potassium-doped alumina.
14. The process of claim 1, wherein the solid treatment material is a potassium-doped zeolite3.
15. The process of claim 1, wherein the solid treatment material comprises a potassium-containing mineral4.
The closest art of record to claims 13-15 is U. Strijowski et al., 113 Eur. J. Lipid Sci. Technol., 387-392 (2011) (“Strijowski”). Strijowski teaches that reduction of the amounts of organic chlorides, both 3-MCPD (3-chloropropane-1,2-diol) esters and related substances, in edible oils, especially palm oil, is desirable bure remains a challenge for the oil manufacturer. Strijowski at page 387, col. 2.
Strijowski teaches the following substance were tested to lower the organic chloride content of palm oil.
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Strijowski at page 388, col. 2. Neither Strijowski nor other art of record teaches or suggest any of (per claims 13-15) “potassium-doped alumina”, “potassium-doped zeolite” or “a potassium-containing mineral” as an adsorbent to lower the organic chloride content of edible oils (e.g., per claim 1 “a liquid feed that comprises one or more fatty acids and/or fatty acid esters”).
Conclusion
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ALEXANDER R. PAGANO
Examiner
Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 In this regard, B. Matthäus et al., 25 Lipid Technology, 151-155 (2013) (“Matthäus”) teaches the vegetable oil producing industry and the downstream food processing industry were worried by the announcement that fatty acid/glycidyl esters of 3-chloropropane-1,2-diol (3-MCPD) have been found in different types of vegetable oils after processing. Matthäus at Abstract. Matthäus teaches that avocado oil, extra virgin olive oil, rapeseed oil, soybean oil and palm kernel fat form only about 1 mg 3-MCPD and glycidyl esters per kg oil after heating at 240 °C for 2 h, while the levels in palm oil, corn oil and coconut oil are markedly higher at up to 14 mg/kg. Matthäus at page 151, col. 1. Matthäus teaches that the chlorine source enters the plants from the soil/environment. Matthäus at page 151, cols. 1-2.
2 These are the same organic chlorides referenced in the instant specification. See, specification at page 6, [0020]-[0021]. For example, the specification teaches that, palm oil contains 3-monochloropropanediol (3-MPCD) as the primary chloride-containing organic compound. Specification at page 6, [0021]. The chloride impurities in vegetable oils are known in the art to arise from the environment. See, footnote 2 above.
3 Respecting the claim 14 term “potassium-doped zeolite”, the following applies. The specification does not define “potassium-doped zeolite”. See e.g., specification at page 8, [0029]. Zeolites are inorganic crystalline aluminosilicates with a network of pores classified as microporous materials (pore size< 2 nm). G. Garcia et al., 489 Journal of Crystal Growth, 36-41 (2018). The general composition of the five zeolites can be approximated by the formula NaxAlxSiyO2(x+y) zH2O, where the SiO2/Al2O3 ratio is given by 2y/x. Garcia at page 36, col. 1. Zeolites may be naturally occurring or synthesized. N. Eroglu et al., 97 Journal of the Science of Food and Agriculture, 3487-3499 (2017). The plain meaning of “doped” in the claim’s context is adding potassium. In view of the foregoing, the term “potassium-doped zeolite” is broadly and reasonably interpreted as a synthesized zeolite comprising potassium or a naturally occurring zeolite (which may already comprise some amount of potassium) to which additional potassium is added/doped, for example, by potassium ion exchange.
4 The specification does not define “potassium-containing mineral” or provide and guidance or examples. See e.g., specification at page 8, [0031]. The broadest reasonable interpretation of “potassium-containing mineral”, based on its plain meaning, is an inorganically formed, naturally occurring homogeneous solid with a definite chemical composition and an ordered atomic arrangement, that naturally contains an amount of potassium. MPEP § 2111. Thus, a “potassium-containing mineral” does not include chemically or otherwise modified minerals, for example, further doped with potassium over the naturally occurring levels. Respecting the plain meaning of “mineral” see, M. Nanzyo, et al., Primary minerals, Ch.2, In, Inorganic Constituents in Soil: Basics and Visuals, 11-35 (2018) (at page 11, stating: “[a] mineral is defined as an inorganically formed, naturally occurring homogeneous solid with a definite chemical composition and an ordered atomic arrangement) (emphasis added).
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