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US4059644A Expired / Lapsed US ⏱️ 0.0 years remaining

High density fuels

Assignee: Shell USA Inc
•
Filing: 1976-02-12
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Granted: 1977-11-22
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Expires: 1996-02-12
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Abstract

Abstract A process for making high density fuels by heating a mixture of cyclopentadiene dimer and methylcyclopentadiene dimer at a temperature sufficient to promote substantial formation of the Diels-Alder trimer of the monomeric cyclopentadienes, followed by hydrogen saturation of the olefinically unsaturated trimerization product.

Inventors

  • 👤 Lawrence G. Cannell

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 09:52
CPC Classifications
C; C10; C10G; C10G69/00; C07; C07C; C07C13/00; C07C13/28; C07C13/32; C07C13/62; C07C13/64; C10G45/00; C10L; C10L1/00; C10L1/04; Y; Y10; Y10S; Y10S149/00; Y10S149/12

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 90 words
A process for making high density fuel which comprises a. heating a mixture of cyclopentadiene dimer and methylcyclopentadiene dimer at a temperature of 150°-250° C for from 10 minutes to 3 hours provided that any oxygen present will not exceed 0.1%wt of the mixture, then b. hydrogenating the product of step (a) by reaction with sufficient hydrogen to completely saturate the olfinically unsaturated bonds of said product and in the presence of a hydrogenation catalyst at a temperature of from 25°-160° C and a hydrogen pressure of from 150-800 psig.
Claim 2
Dependent Claim 90 words
A process for making high density fuel which comprises a. heating a mixture of cyclopentadiene dimer and methylcyclopentadiene dimer at a temperature of 150°-250° C for from 10 minutes to 3 hours provided that any oxygen present will not exceed 0.1%wt of the mixture, then b. hydrogenating the product of step (a) by reaction with sufficient hydrogen to completely saturate the olfinically unsaturated bonds of said product and in the presence of a hydrogenation catalyst at a temperature of from 25°-160° C and a hydrogen pressure of from 150-800 psig.
Claim 3
Dependent Claim 31 words
The process of claim 1 wherein the heating temperature employed in step (a) is between 190° C and 230° C and the heating time is from 15 minutes to 1 hour.
Claim 4
Dependent Claim 23 words
The process of claim 1 wherein the mixture contains cyclopentadiene dimer and methylcyclopentadiene dimer in a molar ratio of from 3:1 to 1:3.
Claim 5
Dependent Claim 36 words
The process of claim 1 wherein the hydrogenation is conducted at a temperature of from 80°-120° C at a hydrogen pressure of from 200 to 500 psig, in the presence of a Group VIII metal catalyst.
Claim 6
Dependent Claim 107 words
A process for making high density fuel which comprises a. heating a mixture of cyclopentadiene dimer and methyl cyclopentadiene dimer at a temperature of 150°-250° C for from 10 minutes to 3 hours provided that any oxygen present will not exceed 0.1%wt of the mixture, to form a co-trimer from said dimers, then b. separating said co-trimer from the unreacted dimers and higher order oligomers in the bulk reaction product, c. adding sufficient hydrogen to completely saturate the olefinically unsaturated bonds of the separated co-trimer in the presence of a hydrogenation catalyst at a temperature of from 25°-160° C and a hydrogen pressure of from 150-800 psig.
Claim 7
Dependent Claim 107 words
A process for making high density fuel which comprises a. heating a mixture of cyclopentadiene dimer and methyl cyclopentadiene dimer at a temperature of 150°-250° C for from 10 minutes to 3 hours provided that any oxygen present will not exceed 0.1%wt of the mixture, to form a co-trimer from said dimers, then b. separating said co-trimer from the unreacted dimers and higher order oligomers in the bulk reaction product, c. adding sufficient hydrogen to completely saturate the olefinically unsaturated bonds of the separated co-trimer in the presence of a hydrogenation catalyst at a temperature of from 25°-160° C and a hydrogen pressure of from 150-800 psig.
Claim 8
Dependent Claim 29 words
The process of claim 5 wherein said co-trimer is separated by a separation method selected from the class consisting of fractional distillation, vacuum distillation, fractional crystallization or solvent extraction.
Claim 9
Dependent Claim 109 words
A hydrogenated reaction product of the process which comprises a. heating a mixture of cyclopentadiene dimer and methylcyclopentadiene dimer at a temperature of 150°-250° C for from 10 minutes to 3 hours provided that any oxygen present will not exceed 0.1%w of the mixture, then b. hydrogenating the product of step (a) by reaction with sufficient hydrogen to completely saturate the olefinically unsaturated bonds of said product and in the presence of a hydrogenation catalyst at a temperature of from 25°-160° C and a hydrogen pressure of from 150-800 psig, which hydrogenated reaction product has a liquid density of about 1.029 gm/ml and melting point of about -30° C.
Claim 10
Dependent Claim 109 words
A hydrogenated reaction product of the process which comprises a. heating a mixture of cyclopentadiene dimer and methylcyclopentadiene dimer at a temperature of 150°-250° C for from 10 minutes to 3 hours provided that any oxygen present will not exceed 0.1%w of the mixture, then b. hydrogenating the product of step (a) by reaction with sufficient hydrogen to completely saturate the olefinically unsaturated bonds of said product and in the presence of a hydrogenation catalyst at a temperature of from 25°-160° C and a hydrogen pressure of from 150-800 psig, which hydrogenated reaction product has a liquid density of about 1.029 gm/ml and melting point of about -30° C.

References Cited (Backward Citations)

US3002829A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-11-21 1981-05-23 1981-11-22 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-11-21 1985-05-23 1985-11-22 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-11-21 1989-05-23 1989-11-22 $7700.00 Window Closed / Lapsed

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