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 16-29 of T. Huber et al., US 18/286,582 (May 30, 2022) are pending. Claims 25-29, to non-elected inventions of Groups (II) and (III) are withdrawn from consideration pursuant to 37 CFR 1.142(b). Claims 16-24 are under examination on the merits and are rejected.
Election/Restrictions
Applicant elected Group (IV), with traverse in the Reply to Restriction Requirement filed on June 8, 2026.
Group (IV) Claims 16 and 30 drawn to the process of Group (I), for the coproduction of pyrrolidine and bis(pyrrolidino)butane, the process comprises reacting 1,4-butanediol with ammonia.
Claims 17-24 are added to the invention of elected Group (IV). Claims 25-29, to non-elected inventions of Groups (II) and (III) are withdrawn from consideration pursuant to 37 CFR 1.142(b). The restriction/election requirement is made FINAL.
Applicant’s Traversal
Applicant traverses on the ground that the claims are so linked by a special technical feature of continuous production of pyrrolidine and bis(prrolidino )butane by reacting 1,4-butanediol with ammonia in the presence of hydrogen and a heterogeneous hydrogenation catalyst at a temperature in the pressure separator of greater than 20°C.
This argument is not persuasive because the process of claim 16 is not a special technical feature because it does not make a contribution over the art in view of the § 102/103 rejections below.
Claim Interpretation
Examination requires claim terms first be construed in terms in the broadest reasonable manner during prosecution as is reasonably allowed in an effort to establish a clear record of what applicant intends to claim. See, MPEP § 2111. Under a broadest reasonable interpretation, words of the claim must be given their plain meaning, unless such meaning is inconsistent with the specification. See MPEP § 2111.01.
Interpretation of the Claim 16 Term “using a recycle gas mode”
Claim 16 recites “using a recycle gas mode” as follows
16. A process for the continuous production of pyrrolidine and bis(pyrrolidino)butane, the process comprising reacting 1,4-butanediol with ammonia in the presence of hydrogen and a heterogeneous hydrogenation catalyst in the gas phase using a recycle gas mode, wherein the temperature in the pressure separator is greater than 20°C.
With respect to its meaning, the specification teaches that:
The recycle gas mode is realized by feeding the reaction mixture obtained in the reactor into a pressure separator, where the reaction mixture is separated into a gaseous stream and a liquid reaction product stream (also referred to as "product stream") and recycling the gaseous stream to the reactor.
Such gaseous stream mainly consists of hydrogen and ammonia (no significant amount of the product amines can be found therein). Usually, a part of such gaseous stream is discharged. Otherwise, the amount of gas to be handled would constantly increase because fresh hydrogen and fresh ammonia being continuously fed to the reaction.
That part of the gaseous stream being recycled is also referred to as the "recycle gas" or "recycle gas stream".
Specification at page 2, lines 26-34. Accordingly, the term “using a recycle gas mode” is interpreted in accordance with the specification definition. MPEP § 2111. The specification teaches that “The pressure separator is usually operated at a pressure close to the reaction pressure”. Specification at page 3, lines 4-5. Thus, a pressure separator divides a continuous reactor's effluent into a gaseous NH3/H2 stream and liquid-product phase while maintaining the reactor’s internal pressure.
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)/(2) Rejection over M. Ernst et al., US 2011/0172430 (2011) (Ernst)
Claims 16, 17, and 22-24 are rejected under 35 U.S.C. 102(a)(1)/(2) as being anticipated by M. Ernst et al., US 2011/0172430 (2011) (Ernst).
Ernst teaches that the amination of 1,4-diols leads, depending on the reaction conditions chosen, to 1-amino-4-hydroxy compounds, 1,4-diamino compounds or five-membered rings having a nitrogen atom (pyrrolidines). Ernst at page 7, [0159]. Ernst teaches that cyclic amines such as pyrrolidines, piperidines, hexamethylenimines, piperazines and morpholines can be prepared in this way from polyhydric alcohols. Ernst at page 8, [0170].
In the working examples, Ernst teaches continuous conversion of diols to cyclic amines employing a copper catalyst of composition 55% by weight of CuO and 45% by weight of gamma-Al2O3, using a recycle gas mode by way of a pressure separator. Ernst at pages 8-9, [0176]-[0178]. The relevant portions of Ernst’s general procedure are reproduced below.
[0178] The feed streams fresh hydrogen, circulating gas, pressurized gases and starting materials were heated to the desired reactor temperature by means of a system comprising three coil heat exchangers. The third heat exchanger was regulated via a temperature sensor just before the reactor. The oil heating of the double-wall reactor was likewise set to the desired reactor temperature.
By means of two further coil heat exchangers, the reactor output was cooled firstly with river water and subsequently using a cryostat to 10° C. and fed to a pressure separator. The separation of liquid phase and gas phase occurred there. The liquid phase was depressurized in a low-pressure separator maintained at 30° C from where the released gases were discharged via the offgas and the liquid was conveyed into the output drum. The gas phase from the pressure separator was recirculated in a defined amount via a circulating gas compressor and once again served as carrier gas for the starting materials. A pressure regulator ensured that excess gas was conveyed to the muffle furnace for incineration. Conversion and selectivity of the output were determined by gas-chromatographic analysis.
Ernst at page 9, [0178] (emphasis added). Ernst teaches Example 2, where one of skill in the art would be apprised that the above general procedure was used.
Example 2
[0181] Shaped bodies having a size of 3x3 mm and 5x5mm were examined in the reaction of butanediol with ammonia to form pyrrolidine at 240° C., a plant pressure of 20 bar and a WHSV of butanediol of 0.29 kg/liter-h. An increase in selectivity to the reaction product by 8% to 89% was observed when using the 3x3 mm shaped bodies compared to the 5x5 mm shaped bodies.
Ernst at page 9, [0181] (emphasis added).
Ernst Example 2 clearly teaches, per claim 16:
16. A process for the continuous production of pyrrolidine and bis(pyrrolidino)butane, the process comprising reacting 1,4-butanediol with ammonia in the presence of hydrogen and a heterogeneous hydrogenation catalyst in the gas phase using a recycle gas mode . . . .
Further, Ernst Example 2 teaches a low-pressure separator temperature of 30 °C and thus meets the claim 16 limitation of “using a recycle gas mode, wherein the temperature in the pressure separator is greater than 20°C”. Ernst Example 2 therefore meets each and every limitation of claim 16.
The further limitations of claim 17 are clearly met.
The limitations of claim 22 are met because the reaction of Ernst Example 2 is conducted at a pressure of 20 bar.
The limitations of claim 23 are met because the reaction of Ernst Example 2 is conducted at a temperature of 240 °C.
The limitations of claim 24 are met because Ernst Example 2 teaches the following weight hourly space velocity (WHSV) of “WHSV of butanediol of 0.29 kg/liter-h”, which falls within the claim 24 range.
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.
Claims 16-24 are rejected under AIA 35 U.S.C. 103 as being unpatentable over W. Schroeder et al., US 4,739,051 (1988) (“Schroeder”) and J. Simon et al., US 6,353,118 (2002) (“Simon”) (primary references) in view of M. Ernst et al., US 2011/0172430 (2011) (Ernst); H. Schmidtke et al., US 2010/0084257 (2010) (“Schmidtke”); and D. Pham et al, US 2022/0356291 (2022) (“Pham”).
W. Schroeder et al., US 4,739,051 (1988) (“Schroeder”)
Schroeder teaches that cyclic imines can be prepared in high yield by reacting a diol with ammonia under hydrogenating conditions in the presence of a heterogenous mixed catalyst based on copper and nickel supported on alumina. Schroeder at col. 1, lines 50-53.
Schroeder teaches that the cyclic imines obtainable by the process according to the invention preferably have from 5 to 7 ring members, examples being pyrrollidine, piperidine, azepine and morpholine and examples of diols suitable for the reaction are propane-1,2-diol, butane-1,4-diol, pentane-1,5-diol, hexane 1,6-diol and diethylene glycol. Schroeder at col. 2, lines 26-33. Schroeder thus teaches one of ordinary skill that the process can be used to convert butanediol to pyrrolidine.
Schroeder teaches that such cyclic amines (pyrrolidine, piperidine, morpholine and azepine), are valuable intermediates for diverse purposes, for example for the preparation of crop protection agents and drugs. Schroeder at col. 1, lines 8-14.
In working Example 1, Schroeder teaches conversion of diglycol to morpholine using the disclosed NH3/H2 mediated reduction and heterogenous Cu/Ni/AlO3 catalyst. Schroeder at cols. 3-4. Here, Schroeder that the catalyst intermediate is first introduced into a tube reactor of 45 mm diameter, surrounded by a jacket through which a heat transfer medium flows. Schroeder at col. 3, lines 46-48. Schroeder teaches the following reaction apparatus.
Apparatus
Above the reactor there is a vaporizer, and also a temperature-balancing zone in which the gas mixture can be brought to the reaction temperature.
Below the reactor is a condenser in which the reaction mixture can be cooled to about 20 °C, and which, in turn, is followed by a separator.1 The uncondensed gas can be recycled, by means of a compressor, to the vaporizer, to which the other reactants are also fed.
Schroeder at col. 3, lines 50-59 (emphasis added). Schroeder teaches that before reaction, the catalyst is activated with hydrogen. Schroeder at col. 3, line 61- col. 4, line 2. Next Schroeder teaches that a 50:50 by volume mixture of hydrogen and ammonia is continuously circulated through the apparatus, then the temperature is set to 210 °C and diglycol is fed into the vaporizer. Schroeder at col. 4, lines 4-10. Schroeder teaches that after deducting ammonia and water, the product contains 93% by weight of morpholine, 3% by weight of methylglycol and 4% by weight of intermediates. Schroeder at col. 4, lines 14-16.
Per the above underlined portion of Schroeder working Example 1, Schroeder teaches the claim 16 limitation of “using a recycle gas mode”.
Note that Schroeder does not teach a working example where the process is used to convert butanediol to pyrrolidine.
J. Simon et al., US 6,353,118 (2002) (“Simon”)
Simon is cited here for the teaching that Schroeder’s above-discussed process respecting rection of butanediol with ammonia under catalytic hydrogenation is known in the art to provide a mixture of pyrrolidine and 1,4-bis(N-pyrrolidino)butane.2 Simon states that preparation of pyrrolidine by reaction of butanediol with ammonia using nickel copper catalyst, as taught by W. Schroeder et al., US 4,739,051 (1988) (“Schroeder”), is a commercially important process, where the crude pyrrolidine prepared by this process contains, in addition to traces of low-boiling impurities such as tetrahydrofuran (THF), high boilers such as N-butylpyrrolidine, N-(4-aminobutyl)pyrrolidine and 1,4-bis(N-pyrrolidino)butane and 40% of water. Simon at col. 1, lines 11-20.
The Examiner summarizes Simon’s explanation of the Schroeder reaction as follows.
PNG
media_image1.png
200
400
media_image1.png
Greyscale
Differences between Schroeder/Simon and Claim 16
One of ordinary skill is taught from the combined teachings of Schroeder and Simon that Schroeder’s disclosed catalyst/NH3/H2 reduction is suitable for (and was actually employed commercially) to convert 1,4-butanediol to a mixture comprising pyrrolidine and 1,4-bis(N-pyrrolidino)butane, per claim 16, “using a recycle gas mode”. Albeit the details of commercial implementation of Schroeder to prepare pyrrolidine, as taught by Simon, appear to be unpublished.
This being said, Schroeder/Simon only fail to teach the temperature at which the pressure separator is to be maintained in the conversion of 1,4-butanediol to a mixture comprising pyrrolidine and 1,4-bis(N-pyrrolidino)butane. Thus, Schroeder/Simon do not specifically teach the claim 16 limitation per the strikeout text below:
16. A process for the continuous production of pyrrolidine and bis(pyrrolidino)butane, the process comprising reacting 1,4-butanediol with ammonia in the presence of hydrogen and a heterogeneous hydrogenation catalyst in the gas phase using a recycle gas mode,
In working Example 1, directed to the different reaction of diglycol to morpholine, Schroeder teaches “the reactor is a condenser in which the reaction mixture can be cooled to about 20 °C, and which, in turn, is followed by a separator”, which implies that the pressure separation (at least for that system) is conducted at 20 °C rather than the instantly claimed “greater than 20 °C”.
M. Ernst et al., US 2011/0172430 (2011) (Ernst)
Ernst teaches a process for the continuous preparation of an amine by reaction of a primary or secondary alcohol, aldehyde and/or ketone with hydrogen and a nitrogen compound selected from the group consisting of ammonia, primary and secondary amines at a temperature in the range from 60 to 300° C. in the presence of a catalyst comprising copper oxide and aluminum oxide. Ernst at page 1, [0001].
Ernst teaches that the amination of 1,4-diols leads, depending on the reaction conditions chosen, to 1-amino-4-hydroxy compounds, 1,4-diamino compounds or five-membered rings having a nitrogen atom (pyrrolidines). Ernst at page 7, [0159]. Ernst teaches that cyclic amines such as pyrrolidines, piperidines, hexamethylenimines, piperazines and morpholines can be prepared in this way from polyhydric alcohols. Ernst at page 8, [0170].
Ernst teaches the claim 16 concept of “using a recycle gas mode” by way of a pressure separator.
[0090] Unreacted starting materials and any suitable by products obtained can be recirculated to the synthesis.
After condensation of the products in a separator, unreacted starting materials can once again be passed, in discontinuous or continuous operation, in the circulating gas stream over the catalyst bed.
Ernst at page 5, [0090] (emphasis added).
Ernst teaches that the catalyst before reduction with hydrogen comprises:
from 20 to 75% by weight of aluminum oxide (Al2O3),
from 20 to 75% by weight of oxygen-comprising compounds of copper, calculated as CuO,
from 0 to 2% by weight of oxygen-comprising compounds of sodium, calculated as NaO, and
less than 5% by weight of oxygen-comprising compounds of nickel, calculated as NiO,
Ernst at page 2, [0023].
Ernst teaches the following general procedure:
[0178] The feed streams fresh hydrogen, circulating gas, pressurized gases and starting materials were heated to the desired reactor temperature by means of a system comprising three coil heat exchangers. The third heat exchanger was regulated via a temperature sensor just before the reactor. The oil heating of the double-wall reactor was likewise set to the desired reactor temperature.
By means of two further coil heat exchangers, the reactor output was cooled firstly with river water and subsequently using a cryostat to 10° C. and fed to a pressure separator.3 The separation of liquid phase and gas phase occurred there. The liquid phase was depressurized in a low-pressure separator maintained at 30° C from where the released gases were discharged via the offgas and the liquid was conveyed into the output drum. The gas phase from the pressure separator was recirculated in a defined amount via a circulating gas compressor and once again served as carrier gas for the starting materials. A pressure regulator ensured that excess gas was conveyed to the muffle furnace for incineration. Conversion and selectivity of the output were determined by gas-chromatographic analysis.
Ernst at page 9, [0178] (emphasis added). Ernst teaches Example 2, where one of skill in the art would be apprised that the above general procedure was used.
Example 2
[0181] Shaped bodies having a size of 3x3 mm and 5x5mm were examined in the reaction of butanediol with ammonia to form pyrrolidine at 240° C., a plant pressure of 20 bar and a WHSV of butanediol of 0.29 kg/liter-h. An increase in selectivity to the reaction product by 8% to 89% was observed when using the 3x3 mm shaped bodies compared to the 5x5 mm shaped bodies.
Ernst at page 9, [0181] (emphasis added).
H. Schmidtke et al., US 2010/0084257 (2010) (“Schmidtke”).
In summary of the detailed discussion below, Schmidtke teaches a similar continuous NH3/H2 reductive amination of a diol (diethylene glycol) mediated by a supported metal catalyst to yield a cyclic amine (morpholine), where the reactor product stream (cooled to 45 °C) is received in a pressure separator. In the pressure separator, unreacted NH3/H2 stream is separated from the higher-boiling product(s) and then the separated NH3/H2 stream is recirculated back to the reactor (per claim16 “using a recycle gas mode”). Schmidtke thus teaches the claim 16 concept of “using a recycle gas mode, wherein the temperature in the pressure separator is greater than 20°C.”
Schmidtke teaches distillation-isolation of morpholine from a reactor as it is formed by reaction of diethylene glycol (DEG) with ammonia/hydrogen in the presence of a catalyst comprising Cu, Ni and Co on zirconium dioxide as support. Schmidtke at page 1, [0001]; Id. at page 4, [0082]; Id. at page 4, [0086].
Schmidtke teaches (per claim 16) “a recycle gas mode” as follows:
[0093] The reaction of diethylene glycol (DEG) with ammonia is preferably carried out in the gas phase in the presence of hydrogen. The gaseous output from the reactor is preferably fed to a heat exchanger in which a partial condensation is preferably carried out (condensation of crude morpholine). The gas phase comprising H2 and NH3 is preferably conveyed back to the DEG vaporizer and then into the reactor.
Schmidtke at page 4, [0093] (emphasis added).
Schmidtke teaches that FIG. 5 shows, interalia, the 7-column arrangement as used in the example, including recycle streams and synthesis part and heat integration (B1=high-pressure separator, B2=intermediate-pressure separator, C1 reactor, V1=compressor, W1,2, 3 and 4-heat exchangers). Schmidtke at page 5, [0109].
In working Example 1, Schmidtke teaches that the following components are fed to heat exchanger W1 then to heater W2 then to reactor C1:
(1) diethylene glycol (DEG) (along with column K70 bottom product and K60 and K70 overhead products);
(2) fresh liquid ammonia mixed with recirculated ammonia from column K10; and
(3) recycle gas consisting predominantly of hydrogen brought from the high pressure separator B1 located at the outlet from the synthesis by means of the compressor V 1.
Schmidtke at page 5, [0111]-[0113]. Schmidtke teaches that [in reactor C1], the reaction of the diglycol to form aminodiglycol and morpholine takes place over the fixed-bed catalyst at a pressure of 200 bar and temperatures up to 215°C. Schmidtke at page 5, [0113].
Next, Schmidtke teaches that:
The output from the reactor [C1] is then cooled to 45° C in the heat exchangers W1, W3 and the air cooler W4.
In the high-pressure separator B1; separation into a gas phase and, a liquid phase occurs.
The gas phase is, as described above, conveyed as recycle gas to the heat exchanger W1.
Schmidtke at page 5, [0113]. Schmidtke thus teaches the claim 16 concept of “using a recycle gas mode, wherein the temperature in the pressure separator is greater than 20°C”, where Schmidtke’s temperature is 45 °C.
D. Pham et al, US 2022/0356291 (2022) (“Pham”)
Pham teaches that 1,4-bis(N-pyrrolidino)butane (compound 3)
PNG
media_image2.png
200
400
media_image2.png
Greyscale
is useful as a catalyst in the production of flexible and rigid polyurethane foam and other polyurethane materials. Pham at page 3, [0030].
Obviousness Rationale
Claim 16 is obvious for the following reasons. One of ordinary skill seeking pyrrolidine and/or 1,4-bis(N-pyrrolidino)butane (in view of their art-known utilities) is motivated to practice the method of Schroeder/Simon for the continuous production of pyrrolidine and bis(pyrrolidino)butane, the process comprising reacting 1,4-butanediol with ammonia in the presence of hydrogen and a heterogeneous hydrogenation catalyst in the gas phase using a recycle gas mode.
One of ordinary skill is clearly motivated to use a recycle gas mode (where the unreacted NH3 and/or H2 is recirculated back to the reactor) as taught by each of Schroeder and Ernst for this reaction and also by Schmidtke for a similar reaction, in the interest of reaction efficiency. One of ordinary skill meets the following limitations of claim 16.
16. A process for the continuous production of pyrrolidine and bis(pyrrolidino)butane, the process comprising reacting 1,4-butanediol with ammonia in the presence of hydrogen and a heterogeneous hydrogenation catalyst in the gas phase using a recycle gas mode . . .
The claim 16 temperature limitation of “wherein the temperature in the pressure separator is greater than 20°C” does not distinguish over the cited art. Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. MPEP § 2144.04(II)(A) (citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). One of ordinary skill would understand that a pressure separator temperature range for hydrogen/ammonia recycle mode is workable. It is a well-settled tenet that one of ordinary skill in the art to develop workable or optimum ranges for result-effective parameters, where Applicant can rebut a prima facie case of obviousness by showing the criticality (unexpected result) of the range. MPEP § 2144.05; see also, In re Boesch, 617 F.2d 272,276 (CCPA 1980). Here,
Schroeder teaches a pressure separator temperature of “about 20 °C”. Schroeder at col. 3, lines 54-56. The claim 16 limitation of “greater than 20°C” is prima facie obvious in view of Schroeder’s teaching of “about 20 °C”. A prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. MPEP § 2144.05(I).
Furthermore, for a similar reaction, Schmidtke teaches the claim 16 concept of “using a recycle gas mode, wherein the temperature in the pressure separator is greater than 20°C”, where Schmidtke’s temperature is 45 °C. Schmidtke at page 5, [0113].
In view of the cited art, particularly the pressure temperature separator temperatures taught by Schroeder (about 20 °C) and Schmidtke (45 °C), one of ordinary skill is motivated to practice the method of Schroeder/Simon for the continuous production of pyrrolidine and bis(pyrrolidino)butane (per claim 16), as proposed above, “wherein the temperature in the pressure separator is greater than 20°C”. Claim 16 is therefore obvious over the cited art.
Claim 17 further recites “wherein the temperature in the pressure separator is greater than 21 °C”. Claim 17 is obvious for the same reasons discussed above.
Claims 18 and 19 are obvious for the following reasons. It is noted that the cited art does not teach the specific pressure of the pressure separator. Note that Schmidtke teaches a “high-pressure separator” as follows.
The reaction of the diglycol to form aminodiglycol and morpholine takes place over the fixed-bed catalyst there at a pressure of 200 bar and temperatures up to 215°C.
The output from the reactor [C1] is then cooled to 45° C in the heat exchangers W1, W3 and the air cooler W4.
In the high-pressure separator B1; separation into a gas phase and, a liquid phase occurs.
The gas phase is, as described above, conveyed as recycle gas to the heat exchanger W1.
Schmidtke at page 5, [0113] (emphasis added). Here, one of ordinary skill is motivated to practice (per claim 18) “wherein the pressure separator is operated at a pressure close to the reaction pressure” (and the similar recitation of claim 19) because, under the continuous reaction conditions, the hydrogen/ammonia recycle mode clearly requires a pressurized hydrogen/ammonia stream. One of ordinary skill is motivated to adjust the pressure separator pressure to as low as possible, to promote hydrogen/ammonia separation from the product stream, while at the same time maintaining the system pressure for the continuous reaction. By keeping the system at about a constant pressure, the system avoids the energy costs of pressure adjustments.
Claims 20 is obvious because Ernst teaches the specific parameters of claim 20. Claim 20 recites:
20. The process according to claim 16, wherein the recycle gas stream has a flow rate in the range from 40 to 1500 m3 at operating pressure/[ m3 of catalyst (bed volume) • h].
Ernst teaches the limitation as follows.
[0069] The circulating gas flow is preferably in the range from 40 to 1500 m3 (at operating pressure)/m of catalyst (bed volume) •h) . . .
Ernst at page 4, [0069]. Claim 20 is therefore obvious.
Claim 21 is obvious for the following reasons. Claim 21 recites:
21. The process according to claim 16, wherein fresh ammonia is added in a molar amount which is from 0.90 to 100 times that of the alcohol.
One of ordinary skill is motivated to supplement the recycle ammonia stream with fresh ammonia to maintain a high ammonia concentration, where ammonia is a required reactant. In this regard, Schmidtke teaches:
[0112] Liquid ammonia is mixed with recirculated ammonia from the column K10 and fed continuously to the heat exchanger W 1.
Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. MPEP § 2144.04(II)(A) (citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
Claims 22 and 23 are obvious because Ernst carries out the reaction at a pressure of 20 bar and 240 °C. Ernst at page 9, [0181].
Claims 24 is obvious because Ernst teaches the specific parameters of claim 20. Claim 24 recites:
24. The process according to claim 16, wherein the liquid hourly space velocity is in the range from 0.1 to 2.0 kg of alcohol per litre of catalyst bed volume an hour.
Ernst teaches the limitation as follows.
[0086] The space velocity over the catalyst is preferably in the range from 0.1 to 2.0 kg, preferably from 0.1 to 1.0 kg, particularly preferably from 0.2 to 0.6 kg, of alcohol, aldehyde and/or ketone per liter of catalyst (bed volume) and hour.
Ernst at page 4, [0086].
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALEXANDER R PAGANO whose telephone number is (571)270-3764. The examiner can normally be reached 8:00 AM through 5:00 PM.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
ALEXANDER R. PAGANO
Examiner
Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 With respect to this portion of Schroeder (which corresponds to German language document EP 0070397A1), the instant specification teaches that:
EP 70397A1 (BASF) relates to a process for the production of cyclic amines. According to the examples the reaction mixture is cooled to 20°C and fed into a pressure separator (page 6, lines 32 to 34).
Specification at page 1, lines 24-26 (emphasis added).
2 See also, A. Timofeev et al, 52 Russian Journal of Organic Chemistry, 1756-1771 (2016) (see Scheme 2 at page 1757). Timoffeev cited here merely as further evidencing Simon’s assertion that rection of butanediol with ammonia under catalytic hydrogenation is known in the art to provide a mixture of pyrrolidine and 1,4-bis(N-pyrrolidino)butane.
3 With respect to this portion of Ernst (which corresponds to German language document WO 2010/031719), the instant specification teaches that:
WO 2010/031719 A1 relates to a process for the preparation of amines in the gas phase. In the experimental section the production of various amines using a gas recycle mode is taught. According to the examples the reactor output is cooled to 10°C and fed into a pressure separator (page 22, line 29).
Specification at page 1, lines 15-20 (emphasis added).
Prosecution Insights