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 .
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
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Claim 1 provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 5-6 of copending Application No. 18/699,478 in view of Choi et al., U.S. Patent No. 6,201,159 in view of Rhee et al., U.S. Patent Publication No. 2011/0100917.
Instant claim 1 requires aldol condensation of aqueous formaldehyde and isobutyl aldehyde, HPA extraction, aldol purification, HPA hydrogenation and NPG purification, and further requires recovery of catalyst-containing wastewater from one or more of the aldol-purification, NPG-purification and extractant-recovery operations; supplying that wastewater to a volatile-organic-compound separation column; distilling the wastewater to obtain an upper catalyst-containing stream and a lower catalyst-depleted wastewater stream; and supplying the lower stream to a wastewater-treatment system.
Reference claim 1 of Application No. 18/699,478 claims the underlying NPG-production process, including aqueous formaldehyde/isobutyl-aldehyde aldol reaction, HPA extraction, catalyst recovery, aldol purification, HPA hydrogenation and NPG recovery. Reference claim 5 requires NPG purification with catalyst/extractant and HPNE recovery, and reference claim 6 requires recovery of catalyst and extractant and return of the catalyst to aldol purification and extractant to aldol extraction.
The principal difference is the collection and additional treatment of catalyst-containing aqueous waste streams.
Choi is directed to continuous NPG manufacture using the same chemistry. Choi teaches reacting isobutyraldehyde with aqueous formaldehyde in the presence of a tertiary alkylamine catalyst; extracting HPA with a water-immiscible organic solvent; using water to remove water-soluble byproducts including organic acids and triethylamine salts; distilling the HPA-containing organic phase to remove low-boiling isobutyraldehyde, triethylamine and water; combining the aqueous phase with the low-boiling fraction in an extractive-distillation operation; and recycling recovered material to the condensation step. Choi, col. 3, ll. 1–57. In its preferred process, Choi specifically feeds formaldehyde, isobutyraldehyde and triethylamine to the aldol reactor, performs octanol extraction, removes isobutyraldehyde/TEA/water by distillation, and recovers/recycles the low-boiling materials in extractive-distillation column 40. Choi, col. 5, ll. 7–41.
Choi is not relied upon for the raffinate-saponification limitation. Choi's separate saponification occurs downstream of hydrogenation and therefore does not establish the raffinate saponification claimed in the present applications. The raffinate-saponification feature, where relevant, is supplied by the claims of Application No. 18/699,478 themselves.
Rhee teaches recovery of amine from amine-containing wastewater. Rhee explains that residual chemicals in water may increase BOD and total nitrogen, ¶ [0005], and identifies recovery and recycling of high-concentration/high-purity amine from wastewater as an objective, ¶ [0006]. Rhee specifically teaches further separating amine by distilling the remaining amine-containing wastewater at no more than 150°C and 100 mmHg, ¶¶ [0007], [0034], and teaches an evaporation tower followed by cooling/condensation to further separate amine, ¶¶ [0008], [0037]. Rhee states that such recovery reduces the load on existing wastewater-treatment plants and permits recovery and reutilization of the amine, ¶ [0009]
Rhee is not NPG-specific; it concerns amine-containing wastewater from power plants. It nevertheless is reasonably pertinent to the problem faced by the claimed process because it addresses the same technical problem—removal and recovery of a volatile amine from an aqueous waste stream before downstream wastewater treatment.
It would have been obvious to a person of ordinary skill, after performing the NPG-production and catalyst/extractant-recovery operations claimed in Application No. 18/699,478, to collect the resulting amine-catalyst-containing aqueous streams and subject them to the amine-recovery distillation taught by Rhee. Choi confirms that water/TEA-containing and low-boiling TEA-containing streams were known consequences of the same NPG production chemistry, while Rhee provides an express reason for the additional treatment: reducing wastewater-treatment loading while recovering reusable amine.
Rhee ¶ [0037] teaches that only water and amine are evaporated from the wastewater during the additional separation and that the amine is thereby further separated from the wastewater. Thus, application of Rhee's distillation to the catalyst-containing wastewater of the reference NPG process would predictably provide an upper vapor/discharge containing volatile amine catalyst and a lower wastewater fraction depleted in that catalyst. Supplying the resulting catalyst-depleted wastewater to conventional wastewater treatment follows directly from Rhee's stated objective of reducing the loading imposed on downstream treatment facilities, ¶ [0009].
Claim 1 is therefore an obvious variation of the inventions defined by reference claims 1, 5 and 6 in view of Choi and Rhee and is not patentably distinct.
Claim 2 — Over Claim 6 of Application No. 18/699,478 in View of Choi and Rhee
Claim 2 additionally requires circulating the catalyst-containing upper discharge stream from the VOC separation column to the aldol purification process. Reference claim 6 expressly requires recovering catalyst and supplying the recovered catalyst to the aldol purification column.
Rhee teaches recovery and reutilization of amine separated from wastewater, ¶¶ [0006], [0009], [0048]–[0049]. Choi teaches recovery and recycle of TEA in the NPG-production process, col. 3, ll. 44–57; col. 5, ll. 33–41.
Once the amine catalyst has been recovered from the wastewater in accordance with the combination applied to claim 1, returning that recovered catalyst to the same aldol-purification operation to which reference claim 6 already sends recovered catalyst is the predictable reuse of the recovered material for its established function. Claim 2 is not patentably distinct.
Claim 3 — Over Claims 3 and 6 of Application No. 18/699,478 in View of Choi and Rhee
Claim 3 further requires circulating unreacted isobutyl aldehyde and catalyst separated during aldol purification to the aldol reaction process.
Reference claim 3 expressly requires circulating the upper discharge stream from the aldol-purification column to the aldol reactor.
Choi independently confirms the conventionality of this recycle in the same NPG chemistry: the low-boiling fraction containing isobutyraldehyde and triethylamine is recovered and recycled to the condensation step, col. 3, ll. 44–57, and the preferred embodiment returns low-boiling materials recovered in extractive-distillation column 40 for reuse, col. 5, ll. 33–41.
Rhee supplies the catalyst-containing wastewater treatment applied to claim 1. Thus, adding that treatment to the recycle process expressly claimed in reference claim 3 would produce the method of instant claim 3. Claim 3 is not patentably distinct.
Claim 4 — Over Claims 1 and 6 of Application No. 18/699,478 in View of Choi and Rhee
Claim 4 further requires saponifying the raffinate obtained in aldol extraction to reduce catalyst salt to catalyst.
Reference claim 1 expressly requires supplying the catalyst-salt-containing raffinate to a saponification reactor to reduce the catalyst salt to catalyst.
Accordingly, the additional subject matter of claim 4 is already expressly claimed in Application No. 18/699,478. Choi is not relied upon for this limitation. Choi's saponification occurs after hydrogenation, at col. 4, approximately ll. 10–18, and concerns hydrolysis of NPG ester precursors rather than the raffinate catalyst salts.
Rhee and Choi are relied upon only for the wastewater-recovery modification discussed for claim 1. Claim 4 therefore is not patentably distinct.
Claim 5 — Over Claims 2 and 6 of Application No. 18/699,478 in View of Choi and Rhee
Claim 5 requires distilling the catalyst regenerated during saponification to separate wastewater and catalyst and circulating the separated catalyst to aldol purification.
Reference claim 2 expressly requires supplying the saponification-reactor discharge to a catalyst recovery column, separating a catalyst-containing stream, and supplying that catalyst stream to the aldol purification column.
Reference claim 6 further establishes catalyst recovery and return to aldol purification in the downstream purification portion of the process.
Choi establishes that aqueous/TEA-containing streams are known in NPG manufacture, col. 3, ll. 33–57, while Rhee teaches subsequent recovery of amine from wastewater by distillation, ¶¶ [0007], [0034], [0037].
Accordingly, separately identifying the residual aqueous fraction from the catalyst-recovery operation as wastewater does not render claim 5 patentably distinct, and treating that stream as set forth in claim 1 would have been obvious for the reasons already stated.
Claim 6 — Over Claims 2 and 6 of Application No. 18/699,478 in View of Choi and Rhee
Claim 6 additionally requires supplying wastewater separated from the catalyst-recovery process to the VOC separation column.
Reference claim 2 establishes the post-saponification catalyst-recovery operation. Rhee expressly teaches transferring residual low-purity amine-containing wastewater to an evaporation tower and further separating the amine by evaporation/distillation, ¶¶ [0037], [0046].
It would have been obvious to route the aqueous residual stream from the catalyst-recovery process to the same amine-recovery distillation used for other catalyst-containing wastewater because it contains the same recoverable amine catalyst. Rhee expressly identifies both recovery of valuable amine and reduction of wastewater-treatment loading as benefits, ¶¶ [0009], [0049].
Claim 6 therefore is not patentably distinct.
Claim 7 — Over Claim 6 of Application No. 18/699,478 in View of Choi and Rhee
Claim 7 requires supplying catalyst and extractant separated during NPG purification to the recovery column, separating catalyst-containing wastewater, catalyst and extractant, returning catalyst to aldol purification, and returning extractant to aldol extraction.
Reference claim 6 expressly requires recovering catalyst from the extractant recovery column and supplying it to aldol purification and recovering extractant and supplying it to aldol extraction.
The destination and reuse of the recovered catalyst and extractant are therefore expressly present in the reference claim. Choi teaches water-soluble TEA salts and aqueous streams generated during NPG purification, col. 3, ll. 33–57, and Rhee teaches separating recoverable amine from residual wastewater, ¶¶ [0007]–[0009], [0037].
Separating the aqueous catalyst-bearing portion and subjecting it to the wastewater-treatment modification applied to claim 1 would have been the predictable handling of the aqueous fraction produced by the recovery operation. Claim 7 is therefore not patentably distinct.
Claim 8 — Over Claims 5 and 7 of Application No. 18/699,478 in View of Choi and Rhee
Claim 8 further requires separating HPNE from the second reaction product, distilling an HPNE-containing stream to obtain HPNE, and circulating a small amount of NPG to the NPG-purification process.
Reference claim 5 expressly requires separation of an HPNE-containing stream from the second reaction product and distillation of that stream in an HPNE purification column to obtain HPNE. Reference claim 7 further requires recovering NPG from the HPNE-purification column and refluxing NPG to the NPG-purification column.
The HPNE-purification and NPG-recycle features of instant claim 8 are therefore expressly claimed in Application No. 18/699,478. Rhee and Choi supply the catalyst-containing wastewater treatment applied to the underlying process. Claim 8 is not patentably distinct.
Claim 9 — Over Claims 6 and 8 of Application No. 18/699,478 in View of Choi and Rhee
Claim 9 requires the catalyst to include triethylamine.
Reference claim 8 expressly requires that the catalyst include TEA.
Choi independently teaches use of triethylamine as the tertiary amine catalyst in the NPG aldol reaction and recovery/recycle of TEA-containing low-boiling material. Choi, col. 5, ll. 7–14, 26–41.
Thus, the TEA species provides no patentable distinction. Rhee is relied upon only for treatment of the resulting amine-containing wastewater. Claim 9 is not patentably distinct.
Claim 10 — Over Claims 6 and 9 of Application No. 18/699,478 in View of Choi and Rhee
Claim 10 requires the extractant to include 2-ethylhexanol (2-EH).
Reference claim 9 expressly requires an extractant including 2-EH.
Claim 11 — Further in View of Martin and Michaels
Claim 11 is provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 6 and 8 of Application No. 18/699,478 in view of Choi and Rhee as applied above, and further in view of Martin and Michaels, U.S. Patent No. 4,326,082.
Claim 11 requires that the amount of catalyst in the lower discharge stream from the VOC separation column be 5.0 wt% or less.
Rhee teaches that the purpose of the additional wastewater treatment is to further separate amine from wastewater, reduce BOD/total-nitrogen loading, and permit amine recovery and reuse. Rhee ¶¶ [0005]–[0009], [0037], [0049]. Rhee therefore establishes that the amount of residual amine remaining in the wastewater is directly related to the desired separation result: greater removal produces a more amine-depleted wastewater stream.
Martin and Michaels does not teach that TEA has an aqueous solubility of about 5 wt.%, and no such statement is relied upon. Rather, Martin quantitatively demonstrates that TEA concentration was a routinely measurable and controllable separation parameter. In Example 2, Martin reports that six extraction stages reduced TEA from 1.7 wt% to 0.005 wt% and states that five ideal stages were adequate to reduce the amine level below 0.01 wt%. Martin, col. 9, ll. 8–17.
Martin is not relied upon as teaching the claimed VOC-column bottoms or the particular wastewater process. It is relied upon as corroborating evidence that residual TEA concentration was a known quantitative separation parameter and that concentrations substantially below the claimed 5.0 wt% upper limit were technically achievable using conventional separation operations.
In view of Rhee's express objective of further removing amine from wastewater, a person of ordinary skill would have had reason to operate the amine-separation step to reduce residual catalyst concentration to a suitably low level compatible with downstream wastewater treatment. Determining the extent of separation necessary to attain a residual concentration of 5.0 wt.% or less would have involved adjustment of the known separation operation according to its known result-effective parameter—the degree of amine removal. Martin confirms that TEA concentrations orders of magnitude below 5 wt.% were attainable in conventional separations.
Accordingly, on the present record, claim 11 would have been an obvious variation of the reference claimed invention in view of Choi, Rhee and Martin.
Claim 12 — Further in View of Lehmann
Claim 12 is provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 6 of Application No. 18/699,478 in view of Choi and Rhee as applied to claim 1, and further in view of Lehmann, U.S. Patent No. 5,183,577.
Claim 12 requires supplying the lower discharge stream from the VOC separation column to an evaporator, removing sludge, and supplying an upper fraction of the evaporator from which sludge has been removed to the wastewater-treatment system.
Rhee teaches transferring residual amine-containing wastewater to an evaporation tower and evaporating the wastewater. Rhee further teaches installing a gas/liquid and gas/solid separator between the evaporation tower and cooling tower specifically to prevent solid matter and non-vaporized organic substances from being carried over and entrained in the vapor. Rhee ¶ [0046]. Thus, Rhee supplies the teaching of removing solid/nonvolatile material from the evaporator vapor stream before further handling of the upper fraction.
Lehmann does not expressly use the term “sludge removal” for this operation and is not relied upon for that feature. Lehmann instead teaches the subsequent evaporative wastewater-treatment arrangement. Lehmann concentrates a wastewater liquid stream in a multiple-effect evaporator, withdraws and condenses the evaporated components, and transfers the resulting low-contaminant condensate directly to a biological treatment system while separately withdrawing the concentrated liquid remaining in the evaporator. Lehmann, col. 5, ll. 49–68; col. 6, ll. 1–8; Fig. 2.
It would have been obvious, after performing the amine/VOC recovery of claim 1, to subject the remaining aqueous discharge to the additional evaporative concentration taught by Lehmann because that operation reduces the contaminant burden and provides an evaporated/condensed fraction suitable for biological wastewater treatment. Rhee further teaches separating entrained solid or nonvolatile material from such evaporator vapor before condensation. Combining these conventional wastewater operations would predictably provide: (1) introduction of the catalyst-depleted wastewater to an evaporator; (2) removal of sludge/solid nonvolatile material from the evaporator upper stream; and (3) delivery of the resulting upper fraction to downstream wastewater treatment.
Claim 12 therefore is not patentably distinct.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
Claims 1, 3, 4, 9, and 10 is/are rejected under 35 U.S.C. §103 as being unpatentable over CN 103739170 (“CN’170) in view of Lee et al., US 2017/0349512.
Claim 1
As to claim 1, Lee teaches a method of producing neopentyl glycol comprising performing an aldol-condensation reaction between aqueous formaldehyde and isobutyraldehyde in the presence of an amine catalyst to obtain a reaction product containing hydroxypivaldehyde. Lee discloses that aqueous formaldehyde, isobutyraldehyde, and triethylamine are continuously supplied to an aldol reactor and reacted at approximately 70–95°C. Lee ¶¶41–43 and 56–57.
Lee further teaches contacting the aldol reaction product with an immiscible organic extractant, preferably 2-ethylhexanol, to obtain an organic extract containing hydroxypivaldehyde and an aqueous raffinate containing water-soluble organic-acid salts of the amine catalyst. Lee ¶¶25–26, 43–46, and 58–59.
Lee teaches supplying the organic extract to an HPA distillation column. Isobutyraldehyde, triethylamine, and water are discharged from the upper part of that column, while an HPA solution containing HPA and 2-EH is discharged from its lower part. Lee ¶¶47–51. Thus, Lee teaches an aldol-purification process in which the extract is distilled to separate unreacted isobutyraldehyde and catalyst from hydroxypivaldehyde.
Lee teaches supplying the HPA/2-EH solution to a fixed-bed hydrogenation reactor and hydrogenating HPA to obtain a reaction product containing NPG. Lee ¶¶32–37 and 52–55. Lee also teaches supplying the hydrogenation product to a divided-wall distillation column, discharging organic solvent and water from the upper portion, discharging high-boiling components from the lower portion, and withdrawing NPG from an intermediate portion at a purity of at least 99.5 wt%. Lee ¶¶38–40.
Lee does not expressly teach recovering catalyst-containing wastewater from one or more of the claimed aldol-purification, NPG-purification, and extractant-recovery processes and supplying that wastewater to a VOC separation column that produces a catalyst-containing overhead and catalyst-depleted wastewater bottoms for subsequent wastewater treatment.
CN ’170 teaches treating wastewater generated by the condensation-hydrogenation production of NPG. CN ’170 explains that this wastewater contains a high concentration of trimethylamine catalyst, which is toxic to microorganisms and interferes with biological wastewater treatment. CN ’170 ¶¶2–7.
CN ’170 teaches introducing the NPG wastewater into a stripping column, spraying the wastewater from the top, and introducing steam from the bottom while maintaining the discharged wastewater at approximately 95°C. Most volatile organic components, including trimethylamine, are evaporated from the wastewater, condensed, recovered, and returned to production. The resulting catalyst-depleted wastewater is then cooled and subjected to resin adsorption and biological wastewater treatment. CN ’170 ¶¶8–14, Example 1, and Fig. 1.
It would have been obvious to a person of ordinary skill in the art before the effective filing date to collect the catalyst-containing aqueous streams produced in Lee’s NPG-production and purification process and subject them to the stripping treatment taught by CN ’170. Both references concern wastewater and material recovery in amine-catalyzed NPG manufacturing. CN ’170 expressly identifies residual volatile amine catalyst as a cause of biological toxicity, catalyst loss, odor, and wastewater-treatment difficulty. The proposed combination would have predictably separated a catalyst-containing overhead for recovery and produced catalyst-depleted wastewater suitable for downstream treatment.
The motivation is not based merely on the knowledge of the present application. CN ’170 expressly supplies the reasons for the modification: recovering valuable amine catalyst, reducing the organic and amine concentration of the wastewater, preventing inhibition of biological treatment, and improving material utilization.
The combination therefore teaches or renders obvious every limitation of claim 1.
Claim 3
As to claim 3, Lee further teaches discharging isobutyraldehyde, triethylamine, water, and other low-boiling components from the upper portion of the HPA distillation column, recovering the isobutyraldehyde and triethylamine, and returning them to the aldol reactor. Lee ¶¶49–51.
Lee therefore teaches an aldol-purification process that circulates the separated unreacted isobutyraldehyde and catalyst to the aldol reaction process.
Claim 4
As to claim 4, Lee further teaches treating the aqueous raffinate discharged from the extractor with NaOH and transferring the resulting material to a TEA column to separate and recover TEA. Lee ¶¶44–46 and 49.
Lee more generally describes a reaction tank in which an inorganic base is added to the aqueous layer discharged from the extractor and a catalyst-recovery column that distills the resulting basic aqueous solution to recover aldol catalyst. Lee ¶¶27–28.
Although claim 4 uses the terms “saponifying” and “reduce,” the specification describes the claimed operation as reacting the catalyst salt with a strong inorganic base such as NaOH to liberate reusable catalyst. Lee teaches the same substantive operation.
Claim 9
As to claim 9, Lee teaches that the amine catalyst may be a trialkylamine and most preferably triethylamine. Lee ¶¶19–21 and 56.
Accordingly, the use of TEA is expressly disclosed.
Claim 10
As to claim 10, Lee teaches that the extraction solvent may be a polar organic solvent that is immiscible with water, preferably 2-ethylhexanol. Lee ¶¶23–26 and 58–59.
Accordingly, the use of 2-EH is expressly disclosed.
Rejection II—Claim 8
Claim 8 is rejected under 35 U.S.C. §103 as being unpatentable over CN 103739170 (“CN’170”) in view of Lee et al., US 2017/0349512, and further in view of Wittwer et al., JPH 09-110792, and Choi et al., US 6,201,159.
The teachings and rationale concerning claim 1 are incorporated here.
Lee teaches that crude NPG is supplied to a divided-wall distillation column, from which organic solvent and water are discharged overhead, NPG is withdrawn from an intermediate portion, and high-boiling materials, including hydroxypivalic acid-neopentyl glycol ester, are discharged from the lower portion. Lee ¶¶38–40. Lee therefore teaches separating an HPNE-containing stream from the second reaction product during NPG purification.
Lee does not expressly teach separately distilling that HPNE-containing stream to recover HPNE while recovering and returning residual NPG to the NPG-purification operation.
Wittwer teaches the production and purification of hydroxypivalic acid neopentyl glycol ester. Wittwer reacts an HPA-containing aqueous material in a reaction/distillation column at 20–200 mbar and an overhead temperature of 80–150°C. Low-boiling components are distilled overhead, while HPNE is recovered from the column bottom. Wittwer ¶¶10–15 and claim 1.
Wittwer further teaches that the overhead contains principally water, NPG, and unreacted HPA. Wittwer ¶16. The crude HPNE bottoms may contain HPA and NPG, which Wittwer states can readily be separated by further distillation when necessary. Wittwer ¶17. In the examples, the bottoms contained the desired HPNE together with a smaller quantity of NPG, confirming that NPG is a recoverable component of the HPNE-rich stream. Wittwer Examples 1–3.
Choi additionally teaches that an NPG-purification residue may contain residual NPG and that the residual NPG should be recovered and recycled within the NPG recovery process to increase overall yield. Choi, col. 5, ll. 15–32; col. 6, ll. 1–13; Example 5. Choi reports a residual-NPG recovery of 98.6% and recycles the recovered NPG-containing phase to the preceding NPG recovery operation. Choi, Example 5.
It would have been obvious to further distill Lee’s HPNE-containing bottoms stream according to Wittwer to remove the lower-boiling water, NPG, and HPA and recover HPNE as a useful product. It further would have been obvious to return the recovered NPG to Lee’s NPG-purification process in accordance with Choi because Choi expressly teaches recovering residual NPG from an impurity-containing purification stream to reduce NPG loss and improve overall yield.
A person of ordinary skill would have had a reasonable expectation of success because Wittwer demonstrates separation of NPG from HPNE by distillation based on their relative volatilities, and Choi demonstrates that recovered residual NPG can be returned to the NPG recovery process without impairing continuous operation.
The combination therefore renders claim 8 obvious.
Rejection III—Claim 11
Claim 11 is rejected under 35 U.S.C. §103 as being unpatentable over CN 103739170 (“CN”170”) in view of Lee et al., US 2017/0349512, and further in view of Mitarai et al., US 5,039,424.
The teachings and rationale concerning claim 1 are incorporated here.
CN ’170 teaches stripping NPG-production wastewater to evaporate “most” of the trimethylamine catalyst before supplying the wastewater to downstream adsorption and biological treatment. CN ’170 ¶¶8–14 and Example 1. Thus, CN ’170 teaches that residual amine concentration in the treated wastewater is a result-effective process variable because excessive residual amine inhibits microorganisms and prevents effective biological treatment. CN ’170 ¶¶2–7.
Mitarai teaches that amine-containing industrial wastewater ordinarily contains approximately 10–100,000 ppm amine. Mitarai, col. 3, ll. 17–34. Mitarai expressly identifies trimethylamine among the alkylamines present in treatable wastewater. Mitarai, col. 3, ll. 1–16. The disclosed range of 10–100,000 ppm corresponds to approximately 0.001–10 wt%, and therefore substantially overlaps the claimed range of no more than 5.0 wt%.
Mitarai further teaches adjusting operating conditions according to the amount and nature of amine in the wastewater and demonstrates treated concentrations far below 5.0 wt%. For example, Mitarai reports amine-treated water concentrations of 36–9,200 mg/L in Examples 1–3, depending on feed concentration, and 2–8 ppm in Examples 48–49. Mitarai, Table 1, and col. 11, ll. 29–56.
It would have been obvious to operate CN ’170’s stripping column so that the catalyst concentration in the bottoms was no more than 5.0 wt%. CN ’170 expressly teaches removing most of the amine before biological treatment, while Mitarai establishes that amine concentration is a recognized wastewater-treatment variable, that customary amine-wastewater concentrations overlap the claimed range, and that substantially lower residual concentrations were routinely achieved.
A person of ordinary skill would have adjusted stripping temperature, steam rate, column stages, and residence time to obtain a catalyst concentration compatible with downstream wastewater treatment. The optimization would have involved routine adjustment of a known result-effective variable for the expressly taught purpose of reducing microbial toxicity.
This rejection does not rely on inherency. It relies on the overlapping customary concentration range and routine optimization of an expressly recognized result-effective variable.
Rejection IV—Claim 12
Claim 12 is rejected under 35 U.S.C. §103 as being unpatentable over CN 103739170 in view of Lee et al., US 2017/0349512, and further in view of Elias et al., US 4,935,555.
The teachings and rationale concerning claim 1 are incorporated here.
CN ’170 teaches that the bottoms discharged from the amine-stripping column are subsequently subjected to adsorption and biological wastewater treatment. CN ’170 ¶¶10–14 and Fig. 1. CN ’170 does not expressly place an evaporator between the stripping column and the downstream wastewater-treatment system.
Elias teaches the use of a wiped-film evaporator in an NPG-production and purification process to separate a volatile NPG-containing overhead from a nonvolatile caustic-containing residue. Elias, col. 2, ll. 17–33. Elias explains that evaporation directly separates the volatile material from the caustic residue without prolonged exposure to elevated temperature. Elias, col. 2, ll. 34–52.
Elias further teaches that the residual bottoms contain caustic, salts, impurities, and a small amount of NPG and that the treatment produces a flowable waste stream that can be readily handled. Elias, col. 2, l. 53–col. 3, l. 10. In the illustrated process, the caustic-treated stream is supplied to evaporator 27, the volatile material is removed overhead through line 13, and the nonvolatile caustic residue is discharged through line 14. Elias, col. 3, ll. 17–44 and Fig. 1.
It would have been obvious to place the evaporator taught by Elias between CN ’170’s VOC/amine stripping column and downstream wastewater-treatment system. The stripping-column bottoms would predictably contain water together with nonvolatile salts, catalyst-derived material, and high-boiling process residues. Elias teaches that evaporation in an NPG process separates a volatile overhead from nonvolatile caustic and process residue and provides an easily handled residue stream.
A person of ordinary skill would have employed the evaporator to remove accumulated nonvolatile solids and sludge before sending the volatile, sludge-free aqueous fraction to the downstream wastewater-treatment system. The modification would have reduced solids loading, prevented fouling of the downstream treatment equipment, and provided separate handling of the concentrated sludge. Evaporation is a predictable physical separation, and Elias demonstrates its compatibility with alkaline NPG process streams.
The combination therefore renders obvious supplying the VOC-column bottoms to an evaporator, removing sludge in the evaporator bottoms, and supplying the sludge-free upper fraction to the wastewater-treatment system.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DEBORAH D CARR whose telephone number is (571)272-0637. The examiner can normally be reached Monday-Friday (10:30 am -6:30 pm).
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/DEBORAH D CARR/Primary Examiner, Art Unit 1691
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