Ex Parte Roederer et al

Patent Trial and Appeal Board

Jan 19, 2017

12822770 (P.T.A.B. Jan. 19, 2017)

United States Patent and Trademark Office
UNITED STATES DEPARTMENT OF COMMERCE
United States Patent and Trademark Office
Address: COMMISSIONER FOR PATENTS
P.O.Box 1450
Alexandria, Virginia 22313-1450
www.uspto.gov
APPLICATION NO. FILING DATE FIRST NAMED INVENTOR ATTORNEY DOCKET NO. CONFIRMATION NO.
12/822,770 06/24/2010 Detlef Roederer 1686-164 RCE 6465
23869 7590 01/19/2017
Hoffmann & Rarnn T T P EXAMINER
6900 Jericho Turnpike
Syosset, NY 11791
O DELL, DAVID K
ART UNIT PAPER NUMBER
1625
MAIL DATE DELIVERY MODE
01/19/2017 PAPER
Please find below and/or attached an Office communication concerning this application or proceeding.
The time period for reply, if any, is set in the attached communication.
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte DETLEF ROEDERER, DANIEL ZOLLINGER,
and JEAN-YVES DE RIEDMATTEN1
Appeal 2014-009493
Application 12/822,770
Technology Center 1600
Before DEMETRA J. MILLS, ERIC B. GRIMES, and FRANCISCO C.
PRATS, Administrative Patent Judges.
GRIMES, Administrative Patent Judge.
DECISION ON APPEAL
This is an appeal under 35U.S.C. § 134 involving claims to a method
of making 3-methyl-pyridine, which have been rejected as obvious. We
have jurisdiction under 35 U.S.C. § 6(b).
We reverse.
STATEMENT OF THE CASE
“The present invention concerns a process for the production of 3-
methyl-pyridine (3-picoline). . . which is used as a solvent, for the
1 Appellants identify the Real Party in Interest as Lonza, Limited. (Appeal
Br. 2.)
Appeal 2014-009493
Application 12/822,770
production of medicaments and insecticides as well as for the synthesis of
nicotinic acid and nicotine amide.” (Spec. 1:3—8.)
Claims 1,2, 5—7, and 9 are on appeal. Claim 1 is the only
independent claim and reads as follows (emphasis added):
1. A continuous process for the synthesis of 3-methyl-pyridine
from formaldehyde, paraldehyde, ammonia and acetic acid, comprising
continuously subjecting said compounds in a jet loop reactor to reaction
conditions comprising the following parameters:
h) a reaction temperature of 260-300°C;
i) a molar ratio of formaldehyde and paraldehyde
(calculated as acetaldehyde) of 0.7-1.4 mol/mol;
j) an ammonia concentration of 10-20 weight-%
k) an acetic acid concentration of 4-20 weight-%
l) a paraldehyde (calculated as acetaldehyde) concentration
of 0.4-1.6 Mol/kg
m) a retention time of 10-30 minutes; and
n) a reaction pressure of 30-130 bar; whereby the
space/time yield of 3-methylpyridine is more than 50
kg/m3*h, and the 3-methylpyridine yield is at least 64%
(based on formaldehyde) and the 3-ethylpyridine yield is
at most 4% (based on paraldehyde).
DISCUSSION
The Examiner has rejected all of the claims on appeal under 35 U.S.C.
§ 103(a) as obvious based on Dinkel,2 Grayson,3 and Swee Sin.4 (Ans. 2.)
2 US 4,337,342, June 29, 1982
3 Grayson et al., An Improved Liquid-Phase Synthesis of Simple
Alkylpyridines, 67 Helvetica Chimica Acta 2100—2110 (1984).
4 Tea Swee Sin, A Comparative Study on the Jet Loop Reactor and
Continuos [sic] Stirred Tank Reactor in the Selective Hydrogenation of Palm
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Appeal 2014-009493
Application 12/822,770
The Examiner finds that “Dinkel teaches the synthesis of 3-methyl-pyridine
by the process of the instant claims” {id. at 3), although Dinkel does not
teach all of the ranges recited in claim 1 and does not use a jet loop reactor
{id.).
The Examiner finds that Grayson teaches that “the ratios of
formaldehyde and paracetaldehyde [i.e., paraldehyde] were well known to
affect the yield” and that “[tjemperature is known in the chemical arts to be
a results effective parameter.” {Id.) The Examiner concludes that it would
have been obvious to optimize the ranges of temperature, pressure, and
ratios of reagents. {Id. at 3—4.)
The Examiner finds that “Swee Sin discusses the use of jet loop
reactors as alternatives to continuously stirred tank reactors.” {Id. at 4.) The
Examiner quotes Swee Sin’s disclosure that “many researchers . . . study the
feasibility of alternative Jet Loop Reactor (JLR) to replace the present
conventional Continuous Stirred-Tank Reactor (CSTR) in their systems.”
{Id.) The Examiner also quotes Swee Sin’s statement that “a Jet Loop
Reactor (JLR) is claimed to retrofit well the CSTR and represent a very
attractive alternative technology for hydrogenation process.” {Id.) The
Examiner concludes that “[b]ased on [Swee Sin], the use of a ‘jet loop
reactor’ is an obvious choice.” {Id. at 5.)
Appellants argue, among other things, that
[a] jet loop reactor is known for its efficiency in gas-liquid mass
transfer, and is shown to be used in Swee Sin in a three phase
reaction system. The presently claimed invention however, is a
Olein (I.V.64), Master of Engineering Thesis, Universiti Teknologi Malaysia
(May 2005).
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Appeal 2014-009493
Application 12/822,770
single phase liquid system. The showing of the use (and alleged
interchangeability of JLR and CSTR) of JLR in a multi-phase
system is not relevant to the presently claimed single phase
reaction process, nor that of Dinkel.
(Appeal Br. 8.)
Appellants argue that “there would be no motivation to attempt to use
a jet loop reactor of Swee Sin in the presently claimed process because of
the difference in the reaction types.” (Reply Br. 1.) Thus, Appellants urge
that “a sufficient motivation for a person of ordinary skill to use a jet loop
reactor in the single phase system has not been established.” {Id. at 3.)
We agree with Appellants that the Examiner has not established that it
would have been obvious, based on the cited references, to use a jet loop
reactor in Dinkel’s process. Dinkel discloses a process of making 3-picoline
by reacting acetaldehyde (which can be in the form of paraldehyde) with
formaldehyde, in the presence of an ammonium salt (such as ammonium
acetate), at a temperature between 180-280°C in a closed vessel. (Dinkel
1:51—60, 2:22—23.) The reaction is carried out “in the liquid phase.” {Id. at
1:54.) Dinkel states that its process can be carried out as a continuous
process and “[t]he continuous process can be carried out in any reaction [sic,
reactor] which permits intimate mixing of the reactants, with vigorous
stirring, for example, in a continuously-stirred tank reactor.” {Id. at 3:7—9,
3:15-18.)
Swee Sin discloses a “study [of] the feasibility of retrofitting the
conventional Jet Loop Reactor (JLR) with Continuous Stirred-Tank Reactor
(CSTR) system by performing a comparative study on Jet Loop Reactor
(JLR) and Continuous Stirred-Tank Reactor (CSTR) in the selective
hydrogenation of palm olein [palm oil].” (Swee Sin 2—3.) The
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Appeal 2014-009493
Application 12/822,770
hydrogenation reaction involves hydrogen (gas), liquid palm oil, and a solid
catalyst. (Id. at 12—13, 48 49.)
Swee Sin states that “[i]n the field of chemical and biochemical[]
reaction engineering there has been an increasing interest in Jet Loop
Reactor (JLR) during the last decade, because of their high efficiency in gas
dispersion resulting in high mass transfer rates.” (Id. at 33.) “The principle
in this reactor type is the utilization of the kinetic energy of a high velocity
liquid jet to entrain the gas phase and to create a fine dispersion of the two
phases.” (Id. at 33—34.) “The benefit of this reactor is its efficiency in gas-
liquid mass transfer.” (Id. at 2.)
Thus, Swee Sin discloses that a jet loop reactor provides high
efficiency in reactions involving a gas and a liquid because it creates a
dispersion of the two phases, resulting in high mass transfer rates. Dinkel,
however, expressly states that its reaction takes place in the liquid phase.
The Examiner has not pointed to any gas-phase reactant in DinkeTs process,
nor has the Examiner provided evidence or sound technical reasoning to
show that a skilled worker would have had a reason to use a jet loop reactor,
specifically, in DinkeTs process. We therefore conclude that the Examiner
has not shown that the process of claim 1 on appeal would have been
obvious based on Dinkel, Grayson, and Swee Sin.
SUMMARY
We reverse the rejection of 1, 2, 5—7, and 9 under 35 U.S.C. § 103(a)
based on Dinkel, Grayson, and Swee Sin.
REVERSED
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