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US3864178A Expired / Lapsed US ⏱️ 0.0 years remaining

Liquid polynuclear hydrocarbyl ferrocenes

Assignee: RTX Corp
•
Filing: 1968-03-29
•
Granted: 1975-02-04
•
Expires: 1988-03-29
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Abstract

Abstract Compositions of matter consisting essentially of mixtures of polynuclear hydrocarbyl substituted ferrocene compounds, each ferrocene nucleus being substituted with at least one hydrocarbyl group, the total number of carbon atoms in the hydrocarbyl substituents of each substituted ferrocene nucleus being in the range of from 1-6, said compositions being noncrystalline, noncrystallizable liquids having an average molecular weight no greater than about 950, said compositions being miscible in all proportions in carboxyterminated polybutadiene at ambient conditions and being combustion catalysts for composite solid propellants. These compositions can be produced by free radical coupling of alkylferrocenes or by the condensation, at low temperature and in the presence of an inert diluent, of lower hydrocarbyl substituted ferrocene derivatives, said hydrocarbyl substituents having m carbon atoms, with aliphatic aldehydes containing n carbon atoms wherein m is an integer from 1-6, n is an integer from 1-12 and value of the relationship 2m +n is from 3-14. Dimeric and trimeric species are the most desirable.

Inventors

  • 👤 Thomas P Rudy
  • 👤 Harry J Hyer

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 12:53
CPC Classifications
C; C07; C07F; C07F17/00; C07F17/02; C06; C06B; C06B23/00; C06B23/007; C06B43/00

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 14 words
The composition of claim 1 consisting essentially of the species where p equals 0.
Claim 2
Dependent Claim 17 words
The composition of claim 1 wherein R is a butyl group and R'' and R'''' are hydrogen.
Claim 3
Dependent Claim 16 words
The composition of claim 1, wherein R and R'' are methyl groups and R'''' is hydrogen.
Claim 4
Dependent Claim 98 words
A composition of matter consisting essentially of a mixture of polynuclear hydrocarbyl substituted ferrocene compounds, at least one of the hydrogen atoms of each ferrocene nucleus being replaced by a hydrocarbyl group, the total number of carbon atoms in the hydrocarbyl groups associated with an individual ferrocene nucleus being in the range of from 1-6, said composition being characterized by being a noncrystalline, noncrystallizable liquid having an average molecular weight no greater than about 950, being miscible in all proportions with carboxyterminated polybutadiene at 70* F and exhibiting activity as a combustion catalyst in a composite solid propellant.
Claim 5
Dependent Claim 14 words
The composition of claim 5 consisting essentially of dimeric polynuclear hydrocarbyl substituted ferrocene compounds.
Claim 6
Dependent Claim 16 words
The composition of claim 5 consisting essentially of trimeric and higher polynuclear hydrocarbyl substitiuted ferrocene compounds.
Claim 7
Dependent Claim 21 words
The compositions of claim 5 wherein said hydrocarbyl substituent groups are selected from the group consisting of methyl and butyl groups.
Claim 8
Dependent Claim 19 words
A noncrystalline, noncrystallizable composition of matter consisting essentially of a mixture of polynuclear ferrocene derivatives having the general formula:
Claim 9
Dependent Claim 11 words
The composition of claim 9 wherein p is equal to zero.
Claim 10
Dependent Claim 11 words
The composition of claim 10 wherein p is equal to one.
Claim 11
Dependent Claim 18 words
The composition of claim 9 wherein R is an n-butyl group and R'', R'''' and R'''''' are hydrogen.
Claim 12
Dependent Claim 16 words
The composition of claim 10 wherein R is an n-butyl group and R'', R'''' are hydrogen.
Claim 13
Independent Claim 88 words
A method for producing noncrystalline liquid polynuclear ferrocene derivatives comprising condensing a hydrocarbyl substituted ferrocene, said hydrocarbyl substituent having m carbon atoms, with a material selected from the group consisting of aliphatic aldehydes having n carbon atoms and acetals derived therefrom wherein m is an integer from 1-6, n is an integer from 1-12 and the value of the relationship 2m + n is from 3-14, in an inert diluent and in the presence of a catalytic amount of acid at temperatures of no greater than about 10*C.
Claim 14
Dependent Claim 21 words
The process of claim 14 further comprising the step of fractionating the condensation product and recovering the low molecular weight fraction.
Claim 15
Dependent Claim 19 words
The process of claim 14 wherein said substituted ferrocene is selected from the group consisting of n-butylferrocene and dimethylferrocene.
Claim 16
Dependent Claim 18 words
The process of claim 16 wherein said aldehyde is selected from the group consisting of formaldeyhde and acetaldehyde.
Claim 17
Dependent Claim 13 words
The process of claim 17 wherein the aldehyde is provided as the acetal.

References Cited (Backward Citations)

US3341495A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-02-03 1978-08-05 1979-02-04 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-02-03 1982-08-05 1983-02-04 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-02-03 1986-08-05 1987-02-04 $7700.00 Window Closed / Lapsed

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