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US4085143A
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Manufacture of α,β-unsaturated acids and anhydrides
Assignee: Eastman Chemical Co
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Filing: 1975-06-05
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Granted: 1978-04-18
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Expires: 1995-06-05
Abstract
Abstract The present invention relates to a new process for the manufacture of α,β-unsaturated acids and their anhydrides from formaldehyde, and a saturated acid anhydride containing 1 less carbon atom in the hydrocarbon moiety.
Inventors
- 👤 Jerry D. Holmes
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 09:02
CPC Classifications
C; C07; C07C; C07C51/00; C07C51/347; C07C51/353; C07C51/083; C07C51/54; C07C51/567
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
107 words
A process for producing an α,β-unsaturated acid anhydride of the type ##STR3## and an α,β-unsaturated acid of the type ##STR4## which comprises the steps of reacting an anhydride having the formula ##STR5## wherein R can be hydrogen or an alkyl, aralkyl, or aryl hydrocarbon moiety of from 1 to 10 carbon atoms with formaldehyde or a formaldehyde yielding material in the vapor phase at a temperature of from about 190° C. to about 400° C. in the presence of an oxide of a metal selected from the group consisting of Ag, U, Zn, Ti, Zr, Th, Ta, Nb, Mo, W, and Sn, supported on an inert support.
Claim 2
Dependent Claim
107 words
A process for producing an α,β-unsaturated acid anhydride of the type ##STR3## and an α,β-unsaturated acid of the type ##STR4## which comprises the steps of reacting an anhydride having the formula ##STR5## wherein R can be hydrogen or an alkyl, aralkyl, or aryl hydrocarbon moiety of from 1 to 10 carbon atoms with formaldehyde or a formaldehyde yielding material in the vapor phase at a temperature of from about 190° C. to about 400° C. in the presence of an oxide of a metal selected from the group consisting of Ag, U, Zn, Ti, Zr, Th, Ta, Nb, Mo, W, and Sn, supported on an inert support.
Claim 3
Dependent Claim
66 words
The process of claim 1 wherein the catalyst is formed by mixing an aqueous solution of a water-soluble salt of a metal selected from the group consisting of Ag, U, Zn, Ti, Zr, Th, Ta, Nb, Mo, W, and Sn, with an inert support, removing the water by evaporation, and subsequently calcining the material at a temperature of from about 400° C. to about 600° C.
Claim 4
Dependent Claim
22 words
The process of claim 2 wherein the calcining takes place at a temperature of from about 500° C. to about 550° C.
Claim 5
Dependent Claim
63 words
The process of claim 1, wherein the catalyst consists of the calcined residue of a mixture of silica gel and a salt or an oxide of a metal selected from the group consisting of tantalum, titanium, niobium and zirconium which residue has subsequently been heated at a temperature of from about 650° C. to about 1000° C. in the presence of water vapor.
Claim 6
Dependent Claim
63 words
The process of claim 4 wherein the catalyst is formed by mixing an aqueous solution of a water soluble salt of the selected heavy metal with silica gel, removing the water by evaporation, calcining the material at a temperature of from about 400° C. to about 600° C. and subsequently heating the calcined residue at elevated temperature in the presence of water vapor.
Claim 7
Dependent Claim
23 words
The process according to claim 5 wherein the calcining takes place at a temperature of from about 500° C. to about 550° C.
Claim 8
Dependent Claim
30 words
The process according to claim 4 wherein th calcined residue is heated in the presence of water vapor at a temperature of from about 730° C. to about 780° C.
Claim 9
Dependent Claim
28 words
The process of claim 7 wherein the calcined residue is heated in the presence of water vapor for a period of from about 3 to about 6 hours.
Claim 10
Dependent Claim
20 words
The process of claim 1 wherein R is a straight- or branched-chain alkyl group of 1 to 6 carbon atoms.
Claim 11
Dependent Claim
24 words
The process of claim 1 wherein the anhydride is selected from the group consisting of acetic, propionic, phenyl acetic, butyric, pentanoic, and hexanoic anhydrides.
Claim 12
Dependent Claim
36 words
The process of claim 1 wherein the support is a silica gel having a surface area of less than about 400 square meters per gram, and a pore volume greater than about 0.8 cc. per gram.
Claim 13
Dependent Claim
37 words
The process of claim 11 wherein the support is a silica gel having a surface area of about 340 to about 360 square meters per gram and a pore volume of from about 1.25 cc. per gram.
Claim 14
Dependent Claim
23 words
The process according to claim 1 wherein the reaction is conducted at a temperature of from about 200° C. to about 300° C.
Claim 15
Dependent Claim
14 words
The process according to claim 1 wherein the reaction is conducted at atmospheric pressure.
Claim 16
Dependent Claim
20 words
The process according to claim 1 wherein the ratio of anhydride to aldehyde is from about 1.1:1 to about 5:1.
References Cited (Backward Citations)
FR847370A
Cited
US3051747A
Cited
US3532740A
Cited
GB1242464A
Cited
US3840587A
Cited
US3933888A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-04-17 | 1981-10-17 | 1982-04-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-04-17 | 1985-10-17 | 1986-04-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-04-17 | 1989-10-17 | 1990-04-18 | $7700.00 | Window Closed / Lapsed |