US3852346A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Production of carboxylic acid anhydrides
Assignee: Monsanto Co
•
Filing: 1972-12-26
•
Granted: 1974-12-03
•
Expires: 1992-12-26
Abstract
Abstract The present invention relates to an improved process for the preparation of organic carboxylic acid anhydrides, specifically by the reaction of ethylenically unsaturated compounds having 2 to 30 carbon atoms with carbon monoxide and carboxylic acids or substances which yield carboxylic acids under the reaction conditions, at a temperature of 50*C to 300*C and a partial pressure of carbon monoxide of from 1 to 2,000 psia. in the presence of a catalyst composition essentially comprised of 1. A RHODIUM OR IRIDIUM COMPOUND, AND 2. AN IODIDE COMPONENT SUBJECT TO THE CONDITIONS THAT THE ATOMIC RATIO OF IODIDE TO RHODIUM OR IRIDIUM IS FROM 1:1 TO 300:1, 3. A CATALYST PRESERVER OR REGENERATOR COMPONENT SELECTED FROM THE GROUP CONSISTING OF HYDROGEN OR A COMPOUND CAPABLE OF FORMING HYDROGEN UNDER THE REACTION CONDITIONS. The process is particularly suited to the production of propionic anhydride.
Inventors
- 👤 D Forster
- 👤 A Hershman
- 👤 F Paulik
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 18:04
CPC Classifications
C; C07; C07C; C07C51/00; C07C51/10; C07C51/14; B; B01; B01J; B01J27/00; B01J27/06; B01J27/08; B01J37/00; B01J37/16; B01J37/18; B01J37/22; C07C51/54; C07C51/56
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
95 words
AN IMPROVED PROCESS FOR THE PRODUCTION OF CARBOXYLIC ACID ANHYDRIDES BY THE REACTION OF ETHYLENICALLY UNSATURATED FEEDSTOCK COMPOUNDS HAVING FROM 2 TO 30 CARBON ATOMS, WHICH COMPRISES CONTACTING THE SAID COMPOUND WITH CARBON MONOXIDE, AND AT LEAST ONE REACTANT SELECTED FROM THE GROUP CONSISTING OF CARBOXYLIC ACID HAVING FROM 2 TO 30 CARBON ATOMS AND WATER, AT A TEMPERATURE FROM 50*C TO 300*C AND A PARTIAL PRESSURE OF CARBON MONOXIDE OF 1 PSIA TO 2,000 PSIA, THE IMPROVEMENT COMPRISING THE PRODUCTION OF CARBOXYLIC ACID ANHYDRIDES IN THE PRESENCE OF A CATALYST SYSTEM CONSISTING ESSENTIALLY OF:
Claim 2
Dependent Claim
95 words
AN IMPROVED PROCESS FOR THE PRODUCTION OF CARBOXYLIC ACID ANHYDRIDES BY THE REACTION OF ETHYLENICALLY UNSATURATED FEEDSTOCK COMPOUNDS HAVING FROM 2 TO 30 CARBON ATOMS, WHICH COMPRISES CONTACTING THE SAID COMPOUND WITH CARBON MONOXIDE, AND AT LEAST ONE REACTANT SELECTED FROM THE GROUP CONSISTING OF CARBOXYLIC ACID HAVING FROM 2 TO 30 CARBON ATOMS AND WATER, AT A TEMPERATURE FROM 50*C TO 300*C AND A PARTIAL PRESSURE OF CARBON MONOXIDE OF 1 PSIA TO 2,000 PSIA, THE IMPROVEMENT COMPRISING THE PRODUCTION OF CARBOXYLIC ACID ANHYDRIDES IN THE PRESENCE OF A CATALYST SYSTEM CONSISTING ESSENTIALLY OF:
Claim 3
Dependent Claim
6 words
A RHODIUM OR IRIDIUM COMPOUND, AND
Claim 4
Dependent Claim
6 words
A RHODIUM OR IRIDIUM COMPOUND, AND
Claim 5
Dependent Claim
23 words
AN IODIDE COMPONENT SUBJECT TO THE CONDITIONS THAT THE ATOMIC RATIO OF IODIDE TO RHODIUM OR IRIDIUM IS FROM 1:1 TO 300:1, AND
Claim 6
Dependent Claim
23 words
AN IODIDE COMPONENT SUBJECT TO THE CONDITIONS THAT THE ATOMIC RATIO OF IODIDE TO RHODIUM OR IRIDIUM IS FROM 1:1 TO 300:1, AND
Claim 7
Dependent Claim
23 words
an iodide component subject to the conditions that the atomic ratio of iodide to rhodium or iridium is from 1:1 to 300:1, and
Claim 8
Dependent Claim
23 words
an iodide component subject to the conditions that the atomic ratio of iodide to rhodium or iridium is from 1:1 to 300:1, and
Claim 9
Dependent Claim
27 words
Process as in claim 1 in which the reactants of the group of carboxylic acids and water are carboxylic acids having from 2 to 30 carbon atoms.
Claim 10
Dependent Claim
23 words
an iodide component subject to the condition that the atomic ratio of iodide to rhodium or iridium is from 4:1 to 100:1, and
Claim 11
Dependent Claim
23 words
an iodide component subject to the condition that the atomic ratio of iodide to rhodium or iridium is from 4:1 to 100:1, and
Claim 12
Dependent Claim
107 words
hydrogen as a catalyst preserver or regenerator component in a molar ratio of 5:1 to 10,000:1 to the rhodium or iridium with the proviso that when the process is conducted in the presence of both carboxylic acids having from 2 to 30 carbon atoms and water as reactants, the ratio of moles of water fed to the reactor per mole of carbon monoxide consumed is less than 0.5, and that when the reactant of the group of carboxylic acids and water, is water, the ratio of moles of water fed to the reactor per mole of carbon monoxide consumed is at least 0.5 but less than 1.0.
Claim 13
Dependent Claim
107 words
hydrogen as a catalyst preserver or regenerator component in a molar ratio of 5:1 to 10,000:1 to the rhodium or iridium with the proviso that when the process is conducted in the presence of both carboxylic acids having from 2 to 30 carbon atoms and water as reactants, the ratio of moles of water fed to the reactor per mole of carbon monoxide consumed is less than 0.5, and that when the reactant of the group of carboxylic acids and water, is water, the ratio of moles of water fed to the reactor per mole of carbon monoxide consumed is at least 0.5 but less than 1.0.
Claim 14
Dependent Claim
94 words
An improved process for the production of carboxylic acid anhydrides by the reaction of ethylenically unsaturated compounds having from 2 to 30 carbon atoms, which comprises contacting the said compound with carbon monoxide and at least one reactant selected from the group consisting of carboxylic acids having from 2 to 30 carbon atoms, and water at a temperature from 50*C to 300*C and a partial pressure of carbon monoxide of 1 psia to 2,000 psia, the improvement comprising the production of carboxylic acid anhydrides in the presence of a catalyst system consisting essentially of:
Claim 15
Dependent Claim
94 words
An improved process for the production of carboxylic acid anhydrides by the reaction of ethylenically unsaturated compounds having from 2 to 30 carbon atoms, which comprises contacting the said compound with carbon monoxide and at least one reactant selected from the group consisting of carboxylic acids having from 2 to 30 carbon atoms, and water at a temperature from 50*C to 300*C and a partial pressure of carbon monoxide of 1 psia to 2,000 psia, the improvement comprising the production of carboxylic acid anhydrides in the presence of a catalyst system consisting essentially of:
Claim 16
Dependent Claim
107 words
hydrogen as a catalyst preserver or regenerator component in a molar ratio of 5:1 to 10,000:1 to the rhodium or iridium with the proviso that when the process is conducted in the presence of both carboxylic acids having from 2 to 30 carbon atoms and water as reactants, the ratio of moles of water fed to the reactor per mole of carbon monoxide consumed is less than 0.5, and that when the reactant of the group of carboxylic acids and water, is water, the ratio of moles of water fed to the reactor per mole of carbon monoxide consumed is at least 0.5 but less than 1.0.
Claim 17
Dependent Claim
107 words
hydrogen as a catalyst preserver or regenerator component in a molar ratio of 5:1 to 10,000:1 to the rhodium or iridium with the proviso that when the process is conducted in the presence of both carboxylic acids having from 2 to 30 carbon atoms and water as reactants, the ratio of moles of water fed to the reactor per mole of carbon monoxide consumed is less than 0.5, and that when the reactant of the group of carboxylic acids and water, is water, the ratio of moles of water fed to the reactor per mole of carbon monoxide consumed is at least 0.5 but less than 1.0.
Claim 18
Dependent Claim
107 words
HYDROGEN AS A CATALYST PRESERVER OR REGENERATOR COMPONENT IN A MOLAR RATIO OF 5:1 TO 10,000:1 TO THE RHODIUM OR IRIDIUM WITH THE PROVISO THAT WHEN THE PROCESS IS CONDUCTED IN THE PRESENCE OF BOTH CARBOXYLIC ACIDS HAVING FROM 2 TO 30 CARBON ATOMS AND WATER AS REACTANTS, THE RATIO OF MOLES OF WATER FED TO THE REACTOR PER MOLE OF CARBON MONOXIDE CONSUMED IS LESS THAN 0.5, AND THAT WHEN THE REACTANT OF THE GROUP OF CARBOXYLIC ACIDS AND WATER, IS WATER, THE RATIO OF MOLES OF WATER FED TO THE REACTOR PER MOLE OF CARBON MONOXIDE CONSUMED IS AT LEAST 0.5 BUT LESS THAN 1.0.
Claim 19
Dependent Claim
107 words
HYDROGEN AS A CATALYST PRESERVER OR REGENERATOR COMPONENT IN A MOLAR RATIO OF 5:1 TO 10,000:1 TO THE RHODIUM OR IRIDIUM WITH THE PROVISO THAT WHEN THE PROCESS IS CONDUCTED IN THE PRESENCE OF BOTH CARBOXYLIC ACIDS HAVING FROM 2 TO 30 CARBON ATOMS AND WATER AS REACTANTS, THE RATIO OF MOLES OF WATER FED TO THE REACTOR PER MOLE OF CARBON MONOXIDE CONSUMED IS LESS THAN 0.5, AND THAT WHEN THE REACTANT OF THE GROUP OF CARBOXYLIC ACIDS AND WATER, IS WATER, THE RATIO OF MOLES OF WATER FED TO THE REACTOR PER MOLE OF CARBON MONOXIDE CONSUMED IS AT LEAST 0.5 BUT LESS THAN 1.0.
Claim 20
Dependent Claim
15 words
Process as in claim 1 in which the said rhodium compound is a rhodium halide.
Claim 21
Dependent Claim
15 words
Process as in claim 1 in which the said iridium compound is an iridium halide.
Claim 22
Dependent Claim
22 words
Process as in claim 1 in which the said iodide component is an alkyl iodide having from 1 to 20 carbon atoms.
Claim 23
Dependent Claim
41 words
Process as in claim 1 in which the said ethylenically unsaturated compound is ethylene and the reactant of the group of carboxylic acids and water is acetic acid, and the products are comprised of propionic anhydride, acetic anhydride, and acetic-propionic anhydride.
Claim 24
Dependent Claim
36 words
Process as in claim 1 in which the said ethylenically unsaturated compound is ethylene and the reactant of the group of carboxylic acids and water is propionic acid, and the product is comprised of propionic anhydride.
Claim 25
Dependent Claim
66 words
Process as in claim 1 in which the rhodium or iridium component, and at least part of the iodide promoter are dispersed on a solid support, and the process is conduCted by passing the ethylenically unsaturated compounds, carbon monoxide, hydrogen, and at least one reactant selected from the group of carboxylic acids and water, all in the vapor phase, over the said solid phase catalyst system.
Claim 26
Dependent Claim
21 words
Process as in claim 12 in which at least a portion of the iodide promoter is also in the vapor phase.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1977-12-02 | 1978-06-03 | 1978-12-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1981-12-02 | 1982-06-03 | 1982-12-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1985-12-02 | 1986-06-03 | 1986-12-03 | $7700.00 | Window Closed / Lapsed |