IP Library Granted Patent US 7,795,169
Granted Patent B2
US 7,795,169 · App. 10/566,868 · Granted Sep 14, 2010

Process for preparing cyanopyridines and suitable catalysts therefor

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Quick Facts
Patent No.
US 7,795,169
App. No.
10/566,868
Granted
Sep 14, 2010
Kind
B2
Abstract

The invention relates to a method for the manufacture of cyanopyridines from methylpyridines by their conversion with ammonia and oxygen and catalysts suitable therefor which contain further transition metals in addition to vanadium and phosphorus.

Claims (39)

1. A VPO catalyst of the general formula:

[V 1 P a X b (Y) c O d ] e [Z] f , in which

a=0.1-2.5

b=0-3.0, in particular 0.001-3.0

c=0.1-10

d=depends on the valency of the other elements

e=5-100 (% by weight)

f=95-0 (% by weight), in particular 95-5 with the provision that b and f are not simultaneously 0

X=Cr, Mo, W, Fe, Ru, Co, Rh, Ir, Ni, Pd, Pt, Zn or Nb

Y=cyclic nitrogen compound,

Z=SiO 2 , Al 2 O 3 , ZrO 2 or TiO 2 or their mixtures,

manufactured in accordance with a method in which one carries out the following steps:

a) converting V 2 O 5 and concentrated phosphoric acid in an organic medium under reflux conditions,

b) separating off catalyst precursor that forms and optionally

c) drying at 80 to 140° C.,

d) impregnating the optionally dried catalyst precursor with an aqueous or alcoholic solution of the metal X, with X having the significance quoted above,

e) separating off excess solution,

f) drying and calcining the impregnated material, and

g) optionally forming the catalyst obtained.

2. The VPO catalyst in accordance with claim 1 , characterized in that the catalyst contains SiO 2 , Al 2 O 3 , ZrO 2 or TiO 2 or their mixtures as a support.

3. The VPO catalyst in accordance with claim 1 , characterized in that the catalyst contains 0.01 to 5% by weight of an organic cyclic nitrogen compound.

4. The VPO catalyst in accordance with claim 3 , characterized in that the catalyst contains as the nitrogen compound a compound selected from the group consisting of pyridine, quinoline, pyridazine, pyrimidine, and pyrazine.

5. The VPO catalyst in accordance with claim 3 , characterized in that the catalyst contains 3-methylpyridine as the nitrogen compound.

6. A method of manufacture of 3-cyanopyridine, the method comprising the steps of:

providing a VPO catalyst of the general formula:

[V 1 P a X b (Y) c O d ] e [Z] f , in which

a=0.1-2.5

b=0-3.0, in particular 0.001-3.0

c=0, 1-10

d=depends on the valency of the other elements

e=5-100 (% by weight)

f=95-0 (% by weight), in particular 95-5 with the provision that b and f are not simultaneously 0

X=Cr, Mo, W, Fe, Ru, Co, Rh, Ir, Ni, Pd, Pt, Zn or Nb

Y=cyclic nitrogen compound,

Z=SiO 2 , Al 2 O 3 , ZrO 2 or TiO 2 or their mixtures;

providing 3-methylpyridine;

providing ammonia;

providing oxygen; and

combining the VPO catalyst, 3-methylpyridine, ammonia, and oxygen at temperatures up to 440° C.

Assignments (26)
RELEASE OF SECURITY INTEREST IN PATENT COLLATERAL Recorded Dec 24, 2020
From: BANK OF AMERICA, N.A.
To: VERTELLUS HOLDINGS, LLC
Reel/Frame 054845/0894 →
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Dec 24, 2020
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: VERTELLUS HOLDINGS LLC
Reel/Frame 054845/0944 →
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Dec 24, 2020
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: VERTELLUS HOLDINGS LLC
Reel/Frame 054846/0001 →
PATENT SECURITY AGREEMENT Recorded Dec 22, 2020
From: VERTELLUS HOLDINGS LLC
To: ANTARES CAPITAL LP, AS COLLATERAL AGENT
Reel/Frame 054837/0217 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Feb 20, 2019
From: VERTELLUS HOLDINGS LLC
To: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
Reel/Frame 048390/0174 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ERRONEOUS LISTING OF PATENT NUMBER 6803456 PREVIOUSLY RECORDED ON REEL 040187 FRAME 0714. ASSIGNOR(S) HEREBY CONFIRMS THE FIRST LIEN SECURITY INTEREST. Recorded Feb 28, 2017
From: VERTELLUS HOLDINGS LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 041836/0985 →
CORRECTIVE ASSIGNMENT TO CORRECT THE PATENT NUMBER 6803456 PREVIOUSLY RECORDED AT REEL: 040187 FRAME: 0725. ASSIGNOR(S) HEREBY CONFIRMS THE SECURITY INTEREST . Recorded Feb 28, 2017
From: VERTELLUS HOLDINGS LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 041836/0973 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 9, 2016
From: VERTELLUS SPECIALTIES INC.
To: VERTELLUS HOLDINGS, LLC
Reel/Frame 040268/0600 →
SECURITY INTEREST Recorded Nov 1, 2016
From: VERTELLUS HOLDINGS LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 040187/0714 →
SECURITY INTEREST Recorded Nov 1, 2016
From: VERTELLUS HOLDINGS LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 040187/0725 →
RELEASE OF SECURITY INTEREST Recorded Oct 31, 2016
From: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
To: VERTELLUS SPECIALTIES INC.
Reel/Frame 040179/0529 →
RELEASE OF SECURITY INTEREST Recorded Oct 26, 2016
From: PNC BANK, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT AND COLLATERAL AGENT
To: VERTELLUS SPECIALTIES INC.; VERTELLUS AGRICULTURE & NUTRITION SPECIALTIES LLC; VERTELLUS HEALTH & SPECIALTY PRODUCTS LLC; VERTELLUS PERFORMANCE MATERIALS INC.; VERTELLUS SPECIALTIES PA LLC; VERTELLUS SPECIALTIES MI LLC; RUTHERFORD CHEMICALS LLC; VERTELLUS SPECIALTIES HOLDINGS CORP.
Reel/Frame 040497/0648 →
RELEASE OF SECURITY INTEREST Recorded Oct 26, 2016
From: PNC BANK, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT AND COLLATERAL AGENT
To: VERTELLUS SPECIALTIES INC.; VERTELLUS AGRICULTURE & NUTRITION SPECIALTIES LLC; VERTELLUS HEALTH & SPECIALTY PRODUCTS LLC; VERTELLUS PERFORMANCE MATERIALS INC.; VERTELLUS SPECIALTIES PA LLC; VERTELLUS SPECIALTIES MI LLC; RUTHERFORD CHEMICALS LLC; MRM TOLUIC COMPANY, INC.; TIBBS AVENUE COMPANY
Reel/Frame 040143/0263 →
PATENT SECURITY INTEREST ASSIGNMENT AGREEMENT Recorded Apr 7, 2016
From: JEFFERIES FINANCE LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 038387/0287 →
SECURITY INTEREST Recorded Nov 3, 2014
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To: JEFFRIES FINANCE LLC
Reel/Frame 034092/0975 →
SECURITY INTEREST Recorded Oct 31, 2014
From: VERTELLUS SPECIALTIES INC.; VERTELLUS AGRICULTURE & NUTRITION SPECIALTIES LLC; VERTELLUS HEALTH & SPECIALTY PRODUCTS LLC; VERTELLUS PERFORMANCE MATERIALS INC.; VERTELLUS SPECIALTIES PA LLC; VERTELLUS SPECIALTIES MI LLC; RUTHERFORD CHEMICALS LLC; VERTELLUS SPECIALTIES HOLDING CORP.
To: PNC BANK, NATIONAL ASSOCIATION, AS AGENT
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RELEASE OF SECURITY INTEREST Recorded Oct 31, 2014
From: U.S. BANK NATIONAL ASSOCIATION
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Reel/Frame 034082/0471 →
SECURITY AGREEMENT Recorded Oct 13, 2010
From: VERTELLUS SPECIALTIES INC.; VERTELLUS AGRICULTURE & NUTRITION SPECIALTIES LLC; VERTELLUS HEALTH & SPECIALITY PRODUCTS LLC; VERTELLUS PERFORMANCE MATERIALS INC.; VERTELLUS SPECIALTIES PA LLC; VERTELLUS SPECIALTIES MI LLC; RUTHERFORD CHEMICALS LLC; MRM TOLUIC COMPANY, INC.; TIBBS AVENUE COMPANY
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RELEASE OF COLLATERAL ASSIGNMENT OF PATENTS (REEL/FRAME 020317/0614) Recorded Oct 4, 2010
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COLLATERAL ASSIGNMENT Recorded Jan 4, 2008
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TERMINATION AND RELEASE OF SECURITY INTEREST Recorded Dec 12, 2007
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Reel/Frame 020227/0682 →
COLLATERAL ASSIGNMENT Recorded Dec 11, 2007
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GRANT OF SECURITY INTEREST IN PATENT RIGHTS - FIRST LIEN Recorded Oct 9, 2006
From: VERTELLUS SPECIALTIES INC. (F/K/A REILLY INDUSTRIES, INC.)
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
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GRANT OF SECURITY INTEREST IN PATENT RIGHTS - SECOND LIEN Recorded Oct 9, 2006
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CHANGE OF NAME Recorded Jul 13, 2006
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