Chemistry of hydrocarbon compounds – Alicyclic compound synthesis – Adamantane or derivative
Reexamination Certificate
2001-12-12
2004-12-07
Wood, Elizabeth D. (Department: 1755)
Chemistry of hydrocarbon compounds
Alicyclic compound synthesis
Adamantane or derivative
C585S016000, C585S021000, C585S800000, C585S802000, C585S803000, C117S068000, C117S069000, C117S070000
Reexamination Certificate
active
06828469
ABSTRACT:
BACKGROUND OF THE INVENTION
Field of the Invention
This invention is directed to novel compositions comprising one or more heptamantanes. This invention is also directed to novel processes for the separation and isolation of heptamantane components into recoverable fractions from a feedstock containing at least one or more heptamantane components.
References
The following publications and patents are cited in this application as superscript numbers:
1
Lin, et al.,
Natural Occurrence of Tetramantane
(C
22
H
28
),
Pentamantane
(C
26
H
32
)
and Hexamantane
(C
30
H
36
)
in a Deep Petroleum Reservoir
, Fuel, 74(10):1512-1521 (1995)
2
Alexander, et al.,
Purification of Hydrocarbonaceous Fractions
, U.S. Pat. No. 4,952,748, issued Aug. 28, 1990
3
McKervey, Synthetic
Approaches to Large Diamondoid Hydrocarbons
, Tetrahedron, 36:971-992 (1980).
4
Wu, et al.,
High Viscosity Index Lubricant Fluid
, U.S. Pat. No. 5,306,851, issued Apr. 26, 1994.
5
Chung et al.,
Recent Development in High
-
Energy Density Liquid Fuels
, Energy and Fuels, 13, 641-649 (1999).
6
Sandia National Laboratories (2000),
World's First Diamond Micromachines Created at Sandia
, Press Release, (Feb. 22, 2000) www.Sandia.gov.
7
Balaban et al.,
Systematic Classification and Nomenclature of Diamondoid Hydrocarbons
—I, Tetrahedron. 34, 3599-3606 (1978).
8
Chen, et al.,
Isolation of High Purity Diamondoid Fractions and Components
, U.S. Pat. No. 5,414,189 issued May 9, 1995.
All of the above publications and patents are herein incorporated by reference in their entirety to the same extent as if each individual publication or patent was specifically and individually indicated to be incorporated by reference in its entirety.
State of the Art
Heptamantanes are bridged-ring cycloalkanes. They are the face-fused heptamers of adamantane (tricyclo[3.3.1.1
3,7
]decane). The compounds have a “diamondoid” topology, which means their carbon atom arrangement is superimposable on a fragment of the diamond lattice (FIG.
1
). Heptamantanes possess seven of the “diamond crystal units” and therefore, it is postulated that there are one hundred sixty possible heptamantane structures. Among them, 85 of the one hundred sixty have the molecular formula C
34
H
40
(molecular weight 448) and of these, 7 are symmetrical, having no enantiomers. Six have the molecular formula C
32
H
36
(molecular weight 420) and 67 have the molecular formula C
33
H
38
(molecular weight 434). There are two fully condensed heptamantanes having the molecular formula C
30
H
34
(molecular weight 394).
Little or no published work is available for heptamantanes and higher molecular weight diamondoids. Heptamantane compounds have not been artificially synthesized or isolated and these compounds have been recently thought only to have a theoretical existence.
7
Academic chemists have primarily focused research on the interplay between physical and chemical properties in lower diamondoids such as adamantane, diamantane and triamantane. Adamantane and diamantane, for instance, have been studied to elucidate structure-activity relationships in carbocations and radicals.
3
Process engineers have directed efforts toward removing lower diamondoids from hydrocarbon gas streams.
2
These compounds cause problems during the production of natural gas by solidifying in pipes and other pieces of equipment.
The literature contains little information regarding practical applications of higher diamondoids and even less, if any information regarding heptamantanes. This fact is probably due to extreme difficulties encountered in their isolation and due to failed synthesis attempts. Lin and Wilk, for example, discuss the possible presence of pentamantanes in a gas condensate and further postulate that hexamantane may also be present.
1
The researchers postulate the existence of the compounds solely based on a mass spectrometric fragmentation pattern. They did not, however, report the isolation of a single pentamantane, hexamantane nor mention heptamantane. Nor were they able to separate non-ionized components during their spectral analysis. McKervey et al. discuss an extremely low-yielding synthesis of anti-tetramantane.
3
The procedure involves complex starting materials and employs drastic reaction conditions (e.g., gas phase on platinum at 360° C.). Although one isomer of tetramantane, i.e. anti-, has been synthesized through a double homologation route, these syntheses are quite complex reactions with large organic molecules in the gas phase and have not led to the successful synthesis of other tetramantanes. Similar attempts using preferred ring starting materials in accordance with the homologation route, have likewise failed in the synthesis of pentamantanes. Likewise, attempts using carbocation rearrangement routes employing Lewis acid catalysts, useful in synthesizing triamantane and lower diamondoids have been unsuccessful to synthesize other tetramantanes or pentamantanes. No attempt to synthesize or isolate heptamantanes has been reported.
Among other properties, diamondoids have by far the most thermodynamically stable structures of all possible hydrocarbons that possess their molecular formulas due to the fact that diamondoids have the same internal “crystalline lattice” structure as diamonds. It is well established that diamonds exhibit extremely high tensile strength, extremely low chemical reactivity, electrical resistivity greater than aluminum trioxide (Al
2
O
3
), excellent thermal conductivity, and superb optical properties.
In addition, based on theoretical considerations, the heptamantanes have sizes in the nanometer range and, in view of the properties noted above, the inventors contemplate that such compounds would have utility in micro- and molecular-electronics and nanotechnology applications. In particular, the rigidity, strength, stability, variety of structural forms and multiple attachment sites shown by these molecules makes possible accurate construction of robust, durable, precision devices with nanometer dimensions. The various heptamantanes are three-dimensional nanometer sized units showing different diamond lattice arrangements. This translates into a variety of rigid shapes and sizes for the one hundred sixty heptamantanes. For example, [121212] heptamantane is rod shaped, [12(3,4)12] heptamantane has a cross-shaped structure while [121234] is “L” shaped and [12132] is disc-shaped with one lobe. The two enantiomers of [121312] have left and right handed screw like structures. A variety of other shapes exist among the heptamantanes which may serve in applications which depend upon specific geometries. It has been estimated that MicroElectroMechanical Systems (MEMs) constructed out of diamond should last 10,000 times longer then current polysilicon MEMs, and diamond is chemically benign and would not promote allergic reactions in biomedical applications.
6
Again, the inventors contemplate that the various heptamantanes would have similar attractive properties. Furthermore, most of the heptamantanes (molecular weight 448 as well as the partially condensed 420 and 434) possess chirality, offering opportunities for making nanotechnology objects of great structural specificity and ones which have useful optical properties. Applications of these heptamantanes include molecular electronics, photonic devices, nanomechanical devices, and nanostructured polymers and other materials.
Notwithstanding these advantages of heptamantanes, the art, as noted above, fails to provide for compositions comprising heptamantanes or for processes that would lead to these compositions. In view of the above, there is an ongoing need in the art to provide for compositions comprising one or more heptamantanes.
SUMMARY OF THE INVENTION
This invention is directed to novel compositions comprising one or more heptamantane components.
Accordingly, in one of its composition aspects, this invention is directed to a composition comprising one or more heptamantane components wherein said composit
Carlson Robert M.
Dahl Jeremy E.
Burns Doane , Swecker, Mathis LLP
Chevron U.S.A. Inc.
Wood Elizabeth D.
LandOfFree
Compositions comprising heptamantane and processes for their... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Compositions comprising heptamantane and processes for their..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Compositions comprising heptamantane and processes for their... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3295036