US4093815A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Method for the oxidation of a conjugated diolefin
Assignee: Phillips Petroleum Co
•
Filing: 1976-08-12
•
Granted: 1978-06-06
•
Expires: 1996-08-12
Abstract
Abstract A conjugated diolefin is reacted with at least one compound selected from the group consisting of a carboxylic acid and a carboxylic acid anhydride in the presence of oxygen and a catalyst comprising a rare earth metal compound, an alkali metal compound and a halide compound.
Inventors
- 👤 Paul R. Stapp
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 19:08
CPC Classifications
B; B01; B01J; B01J27/00; B01J27/06; B01J27/08; B01J23/00; B01J23/10; C; C07; C07C; C07C67/00; C07C67/04; C07C67/05
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
215 words
A method for producing diacyloxyalkenes comprising: reacting a conjugated diolefin with oxygen and at least one compound selected from the group consisting of a carboxylic acid and a carboxylic acid anhydride using a catalyst consisting essentially of three components, wherein said first component is a rare earth metal containing compound, wherein said second component is an alkali metal containing compound, wherein said third component is a halide containing compound, wherein the number of carbon atoms in the conjugated diolefin is within a range of from about 4 to about 12, the conjugated diolefin is selected from unsubstituted compounds and substituted compounds wherein the substituents are selected from the group consisting of halogen, cyano and carbalkoxy radicals, and the carboxylic acid and carboxylic acid anhydride are selected from the group consisting of mono and dicarboxylic aliphatic and aromatic acids and acid anhydrides having from about 2 to about 18 carbon atoms per molecule, wherein the first component is selected from the group consisting of rare earth metal oxides, carboxylates, nitrates, halides, sulfates and mixtures thereof, wherein the second component is selected from the group consisting of alkali metal oxides, carboxylates, halides and mixtures thereof, and wherein the third component is selected from the group consisting of rare earth halides, alkali metal halides, organohalides and mixtures thereof.
Claim 2
Independent Claim
215 words
A method for producing diacyloxyalkenes comprising: reacting a conjugated diolefin with oxygen and at least one compound selected from the group consisting of a carboxylic acid and a carboxylic acid anhydride using a catalyst consisting essentially of three components, wherein said first component is a rare earth metal containing compound, wherein said second component is an alkali metal containing compound, wherein said third component is a halide containing compound, wherein the number of carbon atoms in the conjugated diolefin is within a range of from about 4 to about 12, the conjugated diolefin is selected from unsubstituted compounds and substituted compounds wherein the substituents are selected from the group consisting of halogen, cyano and carbalkoxy radicals, and the carboxylic acid and carboxylic acid anhydride are selected from the group consisting of mono and dicarboxylic aliphatic and aromatic acids and acid anhydrides having from about 2 to about 18 carbon atoms per molecule, wherein the first component is selected from the group consisting of rare earth metal oxides, carboxylates, nitrates, halides, sulfates and mixtures thereof, wherein the second component is selected from the group consisting of alkali metal oxides, carboxylates, halides and mixtures thereof, and wherein the third component is selected from the group consisting of rare earth halides, alkali metal halides, organohalides and mixtures thereof.
Claim 3
Dependent Claim
28 words
The method of claim 1 wherein the reaction is carried out in the presence of a carboxylic acid and the carboxylic acid anhydride corresponding to the carboxylic acid.
Claim 4
Dependent Claim
83 words
The method of claim 1 wherein the conjugated diolefin is selected from the group consisting of 1,3-butadiene, 2-methyl-1,3-butadiene, 2-chloro-1,3-butadiene, 2-ethyl-1,3-butadiene, 2-chloro-3-methyl-1,3-butadiene, 1,3-hexadiene, 1,3-pentadiene, 1,3-octadiene, 1,3-cyclohexadiene, 1,3-cyclooctadiene, 1,3-cyclododecadiene; 2-cyano-1,3-butadiene, and 2-carbethoxy-1,3-butadiene; and the carboxylic acid and the carboxylic acid anhydride are selected from the group consisting of acetic acid, propanoic acid, butanoic acid, pentanoic acid, hexanoic acid, octanoic acid, dodecanoic acid, octadecanoic acid, cyclopentanecarboxylic acid, cyclohexanecarboxylic acid, benzoic acid, chloroacetic accid, cyanoacteic acid, trichloroacetic acid, 2-bromododecanoic acid, 2-ethylhexanoic acid and the acid anhydrides thereof.
Claim 5
Dependent Claim
243 words
The method of claim 1 wherein the first component is selected from the group consisting of CeO 2 , CeCl 3 , CeBr 3 , Ce(III) acetate, PrBr 3 , PrO 2 , PrCl 3 , Pr(III) acetate, Nd(III) acetate, NdBr 3 , Nd 2 O 3 , NdCl 3 , Sm(III) acetate, Ce(III) nitrate, Ce(III) sulfate, SmBr 3 SmCl 2 , Sm 2 O 3 , EuBr 3 , EuCl 3 , Eu 2 O 3 , Gd 2 O 3 , GdCl 3 , TbBr 3 , Tb 2 O 3 , Dy(III) acetate, Dy 2 O 3 , DyCl 3 , Dy 2 (CO 3 ) 3 , Er 2 O 3 , ErBr 3 , Er(III) acetate, HoBr 3 , HoCl 3 , Ho 2 O 3 , TmBr 3 , Tm 2 O 3 , YbBr 3 , YbCl 2 , Yb(III) oxalate, Yb 2 O 3 , LuBr 3 , LuCl 3 , Lu 2 O 3 , and didymium salts such as didymium acetate, didymium carbonate, didymium oxide, and didymium chloride; wherein the second component is selected from the group consisting of lithium chloride, lithium bromide, lithium iodide, lithium acetate, lithium benzoate, lithium oxide, lithium octadecanoate, sodium chloride, sodium bromide, sodium acetate, potassium chloride, potassium acetate, potassium benzoate, rubidium chloride, rubidium bromide, rubidium acetate, cesium chloride, cesium acetate, and cesium oxide; and wherein the third component provides a source of bromine, chloride, iodine or mixtures thereof.
Claim 6
Dependent Claim
23 words
The method of claim 4 wherein the third component is selected from the group consisting of organobromine, organochlorine, organoiodine compounds and mixtures thereof.
Claim 7
Dependent Claim
22 words
The method of claim 5 wherein the third component is selected from the group consisting of 1,4-dibromo-2-butene, 1,4-dichloro-2-butene, 1,4-diiodo-2-butene and mixtures thereof.
Claim 8
Dependent Claim
18 words
The method of claim 4 wherein the third component provides a source of bromine, chlorine or mixtures thereof.
Claim 9
Dependent Claim
61 words
The method of claim 1 wherein the ratio of the moles of the rare earth metal compound to the equivalents of the halide component expressed as halide ion ranges from about 1:1 to 1:20 and wherein the ratio of the moles of rare earth metal compound to the moles of the alkali metal compound ranges from about 0.05:1 to about 2:1.
Claim 10
Dependent Claim
60 words
The method of claim 1 wherein the ratio of the moles of the rare earth metal compound to the equivalents of the halide component expressed as halide ion ranges from about 1:3 to 1:10 and wherein the ratio of the moles of rare earth metal compound to the moles of the alkali metal compound ranges from about 0.1:1 to 0.5:1.
Claim 11
Dependent Claim
32 words
The method of claim 8 wherein the amount of catalyst employed ranges from about 0.1 to about 20 mole percent rare earth metal compound based on the amount of conjugated diolefin charged.
Claim 12
Dependent Claim
32 words
The method of claim 8 wherein the amount of catalyst employed ranges from about 1 to about 15 mole percent rare earth metal compound based on the amount of conjugated diolefin charged.
References Cited (Backward Citations)
GB1138366A
Cited
US3637515A
Cited
US3627821A
Cited
DE2012903A1
Cited
GB1277837A
Cited
US3715388A
Cited
JPS4731919U
Cited
JPS4730616U
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-05 | 1981-12-05 | 1982-06-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-05 | 1985-12-05 | 1986-06-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-05 | 1989-12-05 | 1990-06-06 | $7700.00 | Window Closed / Lapsed |