TWI244477B - Compositions comprising higher diamondoids and processes for their separation - Google Patents

Abstract

Higher diamondoids ranging from tetramantanes through undecamantanes are disclosed in isolated and enriched forms. Methods for obtaining these higher diamondoids are disclosed, as well.

Description

1244477 A7 I 丨 .. B7 V. Description of the Invention (1) Relevant (refer to this document) Claims based on 35 USC 1.1 19 (e) claim the following U.S. patent applications ~ 1k preemptive rights. I, i9, 2000 applications Serial Numbers 60 / 262,842; 6,2 1,2001 requested 60 / 300,148; 7,20,2001 requested 60 / 307,063; 8,15,2001 applications 60/10 / 3,563; 9, 5,2001 applications 60/3 17,546; 9,20,2001_ applications 60 / 323,883; 12,4,2001 applications 60 / 334,929; 12,1,2001 applications 60 / 334,938; and 12,12,2001 application 10 / 012,336, all of which are hereby incorporated by reference. BACKGROUND OF THE INVENTION FIELD OF THE INVENTION The present invention is directed to compositions that are isolated or contain high-grade diamond-like ingredients, and are directed to a composition that includes a variety of diamond-like ingredients. The present invention is also directed to a novel method for separating raw materials containing two grades of diamond-like components, and separating high-grade diamond-like components into recoverable fractions. References The following notices and patent superscript numbers are listed in this application:

Fort, Jr ', et al., Adamantane: The Inference of Diamond-Like Structures, chem Rev.,: 277-300 (1964) ^ Sandla Natlonal Laboratones (2000), World's First Diamond Micromachinery by Sandia, Press Release, (2/22 / 2OO) www gov. Eight Lln, Teren., Naturally occurring in deep oil storage tank fuel (C22H28), metal adamantane (c26H32) and hexaamantane (C3gH36), (10): 151 to 152 1 (1995) 1

Chen, et al., Isolation of high-purity diamond-like fractions and components, us 1244477 A7 B7 V. Description of the invention (2)

Patent No. 5,414,189, issued May 9, 1995) Alexander, et al., Removal of Diamond-Like Compounds from Hydrocarbon Distillates, US Patent No. 4,952,747, August 28, 1990 Assignment 6 Alexander, et al., Hydrocarbon Distillation 7 Purification, U.S. Patent No. 4,952,748, August 28, 1990 7 Alexander, et al., Diamond-like compounds removed from hydrocarbon fractions, us Patent No. 4,952,749, August 28, 1990

Alexander, et al., Tobacco House Purification, US Patent No. 4,982,049, January 1, 1991 Assignment 9 Swanson, Method for Extracting Diamond Samples Using a Solvent System, uS Patent No. 5,461,184, October 24 , 1995 Assigned 1G Partndge, et al., Shape Selection Method for Concentrated Diamond-Like Hydrocarbon Solvents, US Patent No. 5,019,665, May 28, 1991 Assigned " Dahl, et al., As an indicator of natural oil cracking Diamond-Like Hydrocarbons, Nature, 54-57 (1999). 12 McKervey, Synthesis of Large Diamond-Like Hydrocarbons, Tetrahedrón, 97, 992 (1980).

Wu, et al., Southern Viscosity Index Lubricant Fluid, Assigned No. 5,306,85 1, April 26, 1994. 14 Chung et al., Recent Development of Energy Density Liquid Fuels, Energy and Fuels, 64 1 -649 ( 1 999). 15 Balaban et al., Systematic Classification and Naming of Diamond Hydrocarbons,

Tetrahedron, 34, 3599-3609. All of the above announcements and patents are hereby incorporated by reference, and each is separately announced. -5- This paper size applies to the Chinese National Standard (CMS) A4 specification (21〇x 297 public directors) 1244477

The special and individual designators of patents are also all hereby incorporated by reference. The stone sample is a very hard structure with a carbon atom skeleton superimposed on the crystal lattice of the diamond (see Figure 1). Adamantane (ten carbon molecules) is the most J-shaped group of diamond-like series, which contains a cage-shaped diamond crystal subunit. King Kong is commercially available and widely used as a chemical intermediate. It can be synthesized from petroleum and recovered. Diadamantane contains iron side subunits with 5 melting sides, and Sanadam firing contains 3 sides. These three substances can be synthesized from petroleum and isolated, and have attracted research attention. Adamantane, diamantane and triamantane are classified as &quot; lower diamond-like &quot;. Tetra adamantane, metal adamantane, etc. have different characteristics from lower adamantane (including polyisomers, palmarity and more than tetramantane, multiple molecular weight forms), and are classified as "advanced diamond-like". Although only Synthesize one of the advanced diamond samples, but its concepts related to the structure and hypothetical properties have been listed. ° Although King Kong understands that it should be a higher number of units in the diamond crystal lattice, such heterogeneous species, tetramantane and diamond. Common examples, that is, the reduced diamond-like family rigid appearance to eleven lower diamond alkane, diamantane and triamantane show non-isomers, but need: four isomers of different isomers; can be stacked in different ways: The four types of Chinese I contain four different diamond cage-shaped subunits. (Two are stereoisomers (mirror images of each other). Because each has ten faces that can be fused to the next diamond cage unit, the four meshes increase by more than four. Tetra adamantane. The number of possible isomers increases rapidly with the diamond-like series of f. Moreover, the single face in the high-grade diamond sample of the phonogram, so the degree of chlorination also shows an increasing changeDifferent molecular weights (Figure υ. Figure 2 shows the calculation of different series of molecules θ ^ for advanced diamond samples in the range of diadamantane. In fact, every petroleum (oil and gas concentration: substances)-6-1244477 V. Description of the invention (4 and oil source rock extracts. Η Medium &gt; said r Β ^ and diamond-like natural concentrate with π 八. For example, the concentration of methyl glutamate in crude oil of relatively low maturity in the Central Valley of California is several. Ah (per 10,000 parts). The United States ... Smackover Formation, Gulf Coasts ^ person, w, L〇aSt <low heat degree oil source of methyl 2 to Gang degree of 20_30ppm. Because a diamond connection, one, U and U are stone samples with stability higher than petroleum k, and the wood burning oil is cracked at high temperature, high temperature, high temperature, high temperature, high temperature, high temperature, and high temperature. Thousands of ppm. Extension; ^ I got jealous-one &quot; PP Renya can't form how to form a South-level diamond sample in the natural system, but may include a process that takes millions of years. Equipment: including four diamonds, metal hardware High-grade diamond-like objects are relatively slightly blinded. In fact, the present invention The author Dahl and Carhon have been embodied in U.S. Patent Application No. 60 / 262,842 and many subsequent documents that have been requested in U9,200 丨 before the research. These compounds are assumed to synthesize only one compound and several other Temporarily consistent (but not isolated) compounds. In particular, McKervey et al. Proposed the use of an artificial multi-stage process to synthesize trans-tetramantane at low yields. 12 Advanced diamond samples cannot be synthesized by the carbon isomerization method used for lower diamond samples. .Lln et al. Suggested that the presence of tetramantane, metal adamantane and hexamantane in deep oil storage tanks by mass spectrometry alone, without the need for any single-ionized substances. Diamond-like raw materials that may be present in the 3 tanks were recovered after distillation Tetragonam and metal adamantane have been discussed by Chen et al.4. Moreover, it is not directed to the isolated material in the tank material. As for the additional background, the presenter has separated the single-advanced diamond-like cyclohexamantane's most concentrated hexamantane series for the present inventors, and has patented the present invention. The total s foot ’has not been confirmed or provided with single diamonds or other advanced diamond samples. -7- This paper size applies to China National Standard (CNS) A4 (210 X 297 mm) 1244477

Dissent: Yi Si King Kong Yan Ba 2 was discovered by the inventor. Formation-and unsubstituted cyclohexamantane-respectively, ^ ρ Summary of the invention The present invention provides-a kind of containing the invention also provides-a kind of winter diamond: or a high-grade diamond-like compound. This product (&amp; 彡 Α ,, Nida s or single-ion compound knife read advanced diamond-like isomerization, sacrifice bafen into y knife,). In addition, the present invention provides a method for making .4, ^ ^ and diamond-like and high-grade diamond-like ingredients. According to the present invention, the various unused high-grade diamond samples previously connected to and separated from the crystal column by the star system include four diamond diamonds x human gates, wj heart, metal adamane, six adamantane, seven adamantane, and octamantine , Jiuhegu "^ yuan" or even ten diamonds. The higher molecular weight of the south, and the stone-like single tortoise by the woman &gt; ^ The viewing festival is not particularly promising because the iron stones are narrow (four to five etc.)厶 景 铒 、 人 丄 ^, &quot; Set for each crystalline subunit added to the structure is the yak under the Q. Think about the solitary ten adamantane in the raw material is generally about any kind-four kinds The adamantane is, for example, about 10 to 6 times, and includes species synthesized in the prior art. Brief description of the drawings Figure 1 Moon-like diamond-like structure and the interrelationship of diamonds. Special descriptions are diamond-like structures and diamonds. The relationship between the lattice subunits. Figure 2 is a table describing the different molecular weights displayed in each diamond-like diamond series. Figure j illustrates the four diamond structure provided by the present invention. Figure 4 Explains that the diamond lattice has a carbon skeleton. Of the four tetramantane, and its 100 lattice plane can be seen ( 4A), n0 lattice plane (Figure 4) 8) and 111 diamond lattice plane (Figure 4C). -8- This paper size applies to China National Standard (CNS) A4 (210 X 297 mm) 1244477 A7 B7 5. Description of the invention (6 Figure 5 illustrates the structure of the metal adamantane provided by the present invention. Figures 6A, 6B, 6C and 6D illustrate the structure of the hexamantane provided by the present invention. Figures 7A, 7B and 7C illustrate the heptamantane provided by the present invention Structure. However, only one of the stereoisomers is shown. Figure 8 illustrates the octamantine structure provided by the present invention. Only examples of molecular weight states of 500, 486, 472, and 432 are shown. Fig. 9 illustrates the nine diamanta provided by the present invention.垸 structure. Only examples of each molecular weight family are shown. Figure 10 illustrates the decamantane structure provided by the present invention, and only examples of each molecular weight family are shown. Figure 11 illustrates the ^ adamantane structure provided by the present invention, and only each Examples of molecular weight families. Figure 12 provides a flow chart representing the steps used in a single ion containing a high-grade diamond-like fraction and a single high-grade diamond-like component. It is important to understand that each step can be used in a different order in some examples and may be used in Discussed in the examples. Figures 13A and 13B A summary of the properties of various advanced diamond-like gc / ms and HPLC included in the application. Figure 14 shows the strategy for single-column c-column separation of tetramantane and metal adamantane. Figure 15 illustrates the development of molecular electronic devices. Relative to c, 8, 9, and 10 (BuckminSterfuUerene) and representative carbon sub-micron tubes used in the selection of high-level performance 0 stone size and shape. The selected diamond ^ skeleton structure, see, Betu ⑽mingqi 'concentrate Gas chromatography of raw materials; original -9-

Mouth 44477 A7 -----B7 彡, description of the invention ~) — raw material is enough (raw material A); shows the recorded concentration of high-grade diamond (this specification cannot be detected). Fig. 17 outline of high temperature mold steaming crane with atmospheric distillation 650 卞 + tower bottom as raw material B. The figure also illustrates the target site (1-10) for high-grade diamond-like separation. Figures 18A and 18B illustrate raw material B65 (rF + distillate fraction from bottom of distillation column # 6 foot gas chromatography). (^ 1〇) (Table 38, Figure 18), and the final product of the thermal cracking process. These figures show that the non-diamond component has been destroyed by the thermal cracking method, and the rhenium diamond-like sample is concentrated, especially hexamantane, and Single dissociation can be performed. Figures 19 and 20 illustrate the dissociation sequence of various individual high-grade diamond samples (hexamantane) on two different HPLC chromatography tubes: as discussed in Examples 1 and 7 on the DS &amp; Hypercarb. Figure 2 1 Explain the siphon gas chromatography data for the preparation of tetramantane single ionization performed in Examples 3 and 5. Fig. 2 1A shows the fraction obtained from the distillate fraction # 33, the raw material A. The black face number refers to The peak of tetramantane. Figure 21B shows the peak that is isolated and sent to the carrier. The circled peaks (2, 4 and 6) are tetramantanes. It is necessary to understand that the two stereoisomers of photoactivated tetramantane are contained in One of these +. Figures 22A, 22B, and 22C illustrate the fourth gas separation from raw material A so that the spare gas chromatogram (Figure 21) The light crystal shadow of the body crystal is engraved on the surname. Figure 2 a is the self-supporting device Hefen # 2 single-separation 'Figure 2 2 is the self-supporting device remaining part # 4 is single-separating, and Figure 2 C is the self-supporting device # 6Single. Because one stereoisomer tetraammonite has the same GC dwell time in Fig. 21, one of the crystals contains distereoisomers. -10- This paper size applies to China National Standard (CNS) A4 Specifications (210 X 297 mm) 1244477 A7 B7 V. Description of the invention (8) Figure 23 A illustrates the gas chromatography of the gaseous distillation interception fraction of the raw material B listed in Example 1, which is used as the raw material in the pyrolysis process The intercepted fraction is the material recovered from the distillation column after distillation of raw material B at about 65 ° F. Tetramantane # 1 to # 3 are shown. Figure 23B illustrates the gas chromatography of the pyrolysis product of the starting material in Figure 23A, That is, raw material B gas distillation at 650 ° F + column bottom interception fraction shows cracking of non-diamond-like components. Figures 24A and 24B compare the completion of the tetramantane-containing and tetra-rich steel fractions injected into the Vydac DS HPLC column. Gas Chromatography of HPLC Fraction # 6. Figure 25 illustrates the preparation of the gaseous distillation of starting material B at 650 ° F + the bottoms of the intercept fractions. It shows the dissolution order of the distillate taken out at various points and the finish of Sijin Steel, and the configuration time of the fraction # 12 used in the sequential separation step. The gas chromatography of the raw material is shown in Figure 23 above. Figure 26 illustrates HPLC chromatography (Figure 25) of Gu Fen 12 operated on a Hyper ere arb static term and acetone move up to obtain tetramantane # 2. Figures 27A and 27B illustrate the use of two separate HPLC columns to isolate them. GC / MS full ion column (TIC) and mass spectrometry for tetramantane # 1. Figures 28A and 28B illustrate GC / MS total ion chromatography (TIC) and mass spectrometry of tetramantane # 2 isolated using two different HPLC columns. Figures 29A and 29B illustrate GC / MS total ion chromatography (TIC) and mass spectrometry of tetramantane # 3 isolated using two different HPLC columns. Figures 3A and 3B illustrate GC / MS total ion chromatography (TIC) and mass spectrometry of methyltetramantane isolated using Hypercarb HPLC. Figure 3 1 A and 3 1 B illustrate the siphon gas phase layer for the preparation of metal adamantane single release -11- This paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) 1244477 A7 B7 V. Invention Note (9) analyze the data. Fig. 3 1A shows the first type of column assembly containing one of the metal adamantane from the heat-treated raw material B. The contents of the library are separated on the second column. Figure 31B shows the second column peak sent to the carrier. Hardware adamane # 1 (the first hardware adamantane that dissolves in GC / MS analysis) is isolated in the carrier 6. Figures 32A and 32B show GC / MS total ion chromatography and mass spectrometry of the metal adamantane # 1, which was isolated by a spare siphon gas chromatography. Fig. 33A is a photolithographic etch of the metal adamantane # 1 crystallized separately from the raw material B by preparative gas chromatography (Figs. 31 and 32). Figure 33B illustrates the co-crystallization of metal adamantane. Fig. 34 illustrates the production of a pyrolysis product of the raw material B distillate fraction pyrolysis product showing the saturated hydrocarbon fraction of the HPLC fraction obtained with an octadecane column and an acetone mobile phase. The standby HPLC refraction system traces (with negative polarity). Hardware adamantane is based on its dissociation number for GC / MS analysis. Figure 35 illustrates the chromatogram of the isolated DSDS HPLC fraction Π of hardware adamantane # 1 when operated on a static phase of 1 ^ 0 € 1 ^ &amp; 1 * 13 with a mobile phase of acetone (Figure 34). Figures 36A and 36B illustrate GC / MS total ion chromatography (TIC) and mass spectrometry of metal adamantane # 1 isolated from two different HPLC columns. Figures 37A and 37B illustrate GC / MS total ion chromatography (TIC) and mass spectrometry of metal adamantane # 2 isolated from two different HPLC columns. Figures 3A and 38B illustrate GC / MS total ion chromatography (TIC) and mass spectrometry of metal adamantane # 3 isolated from two different HPLC columns. Figures 39A and 39B illustrate GC / MS total ion chromatography (TIC) and mass spectrometry of metal adamantane # 4 isolated from two different HPLC columns. -12- This paper size is in accordance with Chinese National Standard (CNS) A4 specification (210X 297 mm) 1244477 A7 B7 V. Description of the invention (10) Figures 40A and 40B illustrate the use of two separate HPLC columns with separate metal justane # 5 GC / MS total ion chromatography (TIC) and mass spectrometry. Figures 41 A and 41B illustrate GC / MS total ion chromatography (TIC) and mass spectrometry of metal adamantane # 6 isolated from two different HPLC columns. Figures 42A and 42B illustrate siphon gas phase chromatography data for the preparation of hexadamantane for single ionization. Fig. 42A shows a first column fraction containing six adamantan bis from feedstock B. Figure 42B shows a second column peak that is isolated and sent to the carrier. Alcohol hexamantine (Figures 43 and 44) can be isolated by this procedure, hexamantine # 2, the second type is hexamantane dissolving in GC / MS analysis, and hexamantane # 8 is the eighth type of dissociation. Thing. Figures 43A and 43B illustrate GC / MS total ion chromatography and mass spectrometry for the preparation of hexamantane # 2 isolated by siphon gas chromatography. Figures 44A and 44B illustrate GC / MS total ion chromatography and mass spectrometry for the preparation of six adamantane # 8 highly concentrated by siphon gas chromatography. This sample contained traces of methyl heptamantane (408 molecular weight). Fig. 45 illustrates photolithographic etching of hexadamantane # 2 crystallized separately from raw material B by preparative gas chromatography (Figs. 42 and 44). Fig. 46 illustrates photolithographic etching of six adamantane # 8 crystals isolated from raw material B by preparative gas chromatography (Figs. 145 and 147). 47A and 47B illustrate GC / MS total ion chromatography (TIC) and mass spectrum of hexamantane # 8 in ODS HPLC fraction # 39. Figures 48A and 48B illustrate GC / MS total ion chromatography (TIC) and mass spectrometry of hexamantane # 10 in ODS HPLC fraction # 48. Figures 49A and 49B illustrate 〇DS HPLC fraction # 63 中 六 Adamantane # 6-13-This paper size applies Chinese National Standard (CNS) A4 specifications (210X 297 mm) 1244477 A7 B7 V. Description of the invention (11) GC / MS total ion chromatography (TIC) and mass spectrometry. Figures 50A and 50B illustrate GC / MS total ion chromatography (TIC) and mass spectra of a large amount of Six King Kong Burn # 2 in Hypercarb HPLC Fraction # 53. Figures 1A and 51B illustrate GC / MS total ion chromatography (TIC) and mass spectrometry of hexamantane # 13 isolated using two different HPLC columns. Figures 52A and 52B illustrate GC / MS total ion chromatography (TIC) and mass spectrometry of hexamantane # 7 isolated using two different HPLC columns. Figures 53 A and 53B illustrate GC / MS reconstructed ion chromatography of condensation "irregular" hexamantanes (mole wt. 382) in the saturated hydrocarbon fraction of the pyrolysis process product of distillation fraction # 6 of feedstock B. / z 3 82 and mass spectrum. Figure 5 4A and 54B illustrate GC / MS reconstructed ion chromatography m / z 3 82 and mass spectrum of irregular hexamantane (Mole wt. 382) in ODS HPLC fraction # 36. Figure 5 55 A and 55B illustrate the GC / MS total ion chromatography (TIC) and mass spectrum of methylhexamantane (Mole wt. 410) isolated in ODS HPLC fraction # 55. Figure 56 illustrates cyclohexamantane and GC / MS Total Ion Chromatography (TIC) of Methylcyclohexamantane 〇DS HPLC with Fractions # 23-26. Figures 57A and 57B illustrate the use of multi-column static phase HPLC (ODS followed by Hypercarb) to isolate the methylated formaldehyde. GC / MS Total Ion Chromatography (TIC) and Mass Spectroscopy of Cycloadamantane # 1 (Mole wt. 356). Figures 58A and 58B illustrate the use of multi-column static phase HPLC (ODS followed by Hypercarb) for high-purity monoisolation. GC / MS Total Ion Chromatography (TIC) and Mass Spectrometry of Methylcyclohexamantane # 2 (Mole wt. 356). Figures 59 and 60 show methylcyclohexamantane # isolated using two different HPLC columns. 1 and methylcyclohexamantane # 2 crystal light _ -14- This paper size is in accordance with Chinese National Standards (CNs) A4 specifications (210X297 mm) 1244477 A7 B7 V. Description of the invention (12) Figure 6 1A and 61 B illustrate the preparation of hexamantanes for single release Siphoning gas chromatographic data. Figure 61A shows the first column fraction containing heptamantane bis from feedstock B. Figure 6 1B shows the second column peak that is isolated and sent to the carrier. From this The program can separate the pure seven gold steel completes (Figures 8 and 9), seven gold gang | Jane # 1, the first heptamantane dissolving in the GC / MS analysis, and the second dissolution of heptamantane. # 2. Figures 62A and 62B illustrate GC / MS Total Ion Chromatography and Mass Spectrometry of Sepamantane # 1 isolated for preparative siphon gas chromatography. Figures 63A and 63B illustrate for preparative siphon gas chromatography. GC / MS Total Ion Chromatography and Mass Spectrometry of Highly Concentrated Heptamantane # 2. Figure 64 illustrates the light of crystallization of Heptamantane # 1 isolated from raw material B by preparative gas chromatography (Figs. 61 and 62). Lithographic etching. Figure 65 illustrates light lithographic etching of hepylgangane # 2 crystallized from raw material B by preparative gas chromatography (Figures 61 and 63). Figures 66A and 66B illustrate DS HPLC GC / MS Total Ion Chromatography (TIC) and Mass Spectrum of Heptamantane Component # 1 in Part # 45. Figures 67A and 67B illustrate GC / MS totals of Heptamantane Component # 2 in ODS HPLC Fraction # 41. Ion chromatography (TIC) and mass spectrometry. Figures 68A and 68B illustrate GC / MS total ion chromatography (TIC) and mass spectrum of heptamantane component # 9 in ODS HPLC fraction # 61. Figures 69A and 69B illustrate GC / MS total ion chromatography (TIC) and mass spectrometry of the heptamantane component # 10 in ODS HPLC fraction # 87. Figures 70A and 70B illustrate GC / MS total ion chromatography (TIC) and mass spectrometry of heptamantane # 1, which is abundant in Hypercarb HPLC fraction # 55. -15- This paper size is in accordance with Chinese National Standard (CNS) A4 (210 X 297 mm) 1244477 A7 B7 V. Description of the invention (13) Figure 7 1A and 71B illustrate the use of two different HPLC columns for adamantane. # 2 GC / MS Total Ion Chromatography (TIC) and Mass Spectrometry. Heptamantane # 2 was isolated from the ODS HPLC fraction # 41 (Figure 67) using a Hypercarb HPLC system. Figure 72 illustrates GC / MS reconstructed ion chromatography m / z 420 showing partially condensed seven gold steel fractions (mole wt. 420) in ODS HPLC fraction # 61. Figure 73 illustrates the mass spectrum of heptamantane with a molecular weight of 420 in Figure 72. Figures 74A and 74B illustrate GC / MS total ion chromatography (TIC) and mass spectrometry of methyl heptamantane (Mole wt. 408) isolated in ODS HPLC fraction # 51. Figures 75A and 75B illustrate GC / MS total ion chromatography (TIC) and mass spectrometry of octamantane # 1 highly concentrated by high performance liquid chromatography. FIG. 76 illustrates light lithography of octamantane # 1 crystallized from raw material B by high performance liquid chromatography. Figures 77A and 77B illustrate GC / MS total ion chromatography (TIC) and mass spectra of co-crystals octamantane # 3 and octamantane # 5 (Figure 77C) grown from ODS HPLC fraction # 63. Figures 78A and 78B illustrate photolithographic etching of cocrystals octamantane # 3 and # 5. Crystal B was dissolved in cyclohexane and analyzed by GC / MS (Figure 77). Figures 79A and 79B illustrate GC / MS total ion chromatography (TIC) and mass spectrum of octamantane # 1 and octamantane # 1 0DS HPLC fraction # 80. Figures 80A and 80B illustrate GC / MS total ion chromatography (TIC) and mass spectrometry of ODS HPLC library # 92 containing octamantane (molecular weight 500). Figures 81A and 81B illustrate GC / MS total ion chromatography (TIC) and mass spectrum with methyl octamantane (QDS HPLC fraction # 94 with a molecular weight of 46C0) and mass spectra. Figures 82A and 82B illustrate nine diamonds concentrated by high performance liquid chromatography -16- __ This paper size is in accordance with Chinese National Standard (CNS) A4 (210X297 mm) 1244477 A7 B7 V. Description of the invention (14) GC / MS total ion chromatography and mass spectrometry. Figures 83A and 83B illustrate the use of two different GC / MS Total Ion Chromatography (TIC) and Mass Spectrometry of Condensed Nonamantane on HPLC Columns. Figures 84A and 84B illustrate mass spectra of photolithographic etching and dissolved crystals of nonamantane crystals. Figures 85A and 85B illustrate methyl groups. GC / MS total ion chromatography (TIC) and mass spectrum of nonamantane (Mole wt. 512). Figures 86A and 86B illustrate [123 1241 (2) 3], with a molecular weight of 456. GC / MS Total Ion Chromatography and Mass Spectrometry of Adamantane. Figures 87A and 87B illustrate [123 1241 (2) 3], molecular weight 456, GC / MS total ion chromatography of ten adamantane isolated using two different HPLC columns. (TIC) and mass spectrum. Figures 88A and 88B illustrate [123 1241 (2) 3], photolithographic etching of decamantane crystals, and mass spectra of dissolved crystals. Figures 8A and 8B illustrate GC / MS selected ion chromatography (TIC) and mass spectrometry of decamantane (Mole wt. 496). Figures 90A and 90B illustrate two methyl decamantane (Mole wt. 470) of 0 (: / "5 total ion chromatography (Ding 1 (:), and 0 (: / 1 ^ 5 mass spectrum dissociated at 18.84 minutes in the analysis. Figures 91A and 91B illustrate the atmospheric distillation fraction # 7 of raw material B (Table 3) GC / MS selective ion chromatography (m / z 508) and mass spectrum of concentrated undecamantane pyrolysate. Figures 92A, 92B, and 92C illustrate the undecamantane component (Mole) that dissolves at 21.07 minutes. wt · 5 08) GC / MS selected ion chromatography (m / z 5 08) and mass spectrometry, that is, methyl undecamantane component (Mole wt. -17- This paper size applies to China National Standard (CNS) A4 specification (210X297 mm)

Pretend

A7

1244477 V. Mass spectrum of invention description (15 522).丨 Claw π hits W lamp 0, distillates the residue of atmospheric pressure), showing dioxin power, and 4 V is considered to be the most favorable distillate containing special grades. Figure 94 shows [1234 1 ] Liuling brush f ,, 仏 ^ to the spiral structure of rightane (right and left). Detailed description of the invention The detailed description contains the following sub-paragraphs: Definition Raw material Isolation method Utilization Example Definition The meaning of the terms used in this text is as follows. • The term 'diamond-like' refers to the inclusion of adamantane, diamantane, triamantane, tetraamantane, hardware adamantane, hexaamantane, heptamantane, octamantane, nonamantane, decamantane, ten Monoamantane and the like, and also all substituted and unsubstituted compound compounds of the adamantane series which also include all isomers and stereoisomers thereof. The substituted &lt; diamond-like preferably includes 1 to 0, more preferably ^ To 4 alkyl substituents. Lower diamond-like composition or "Vanadium appearance, two diamonds;): End and three diamonds &quot; refers to any and / or all of the diamonds, two diamonds and three diamonds Unsubstituted and substituted derivatives. The term ‘’ high-grade diamond-like composition ’means equivalent to tetramantane and above. -18- This paper size applies Chinese National Standard (CNS) A4 (210X297 mm)

Η

1244477 16 V. Description of the invention (Substituted and unsubstituted diamond-like samples, including tetramantane, adamantine, hexamantane, heptamantane, octamantane, nonamantane, decamantane, eleven adamantine, etc. , And contains all isomers and stereoisomers. Better, the southern diamond samples include substituted and unsubstituted tetramantane, adamantine, hexamantane, heptamantane, octamantane, and nine adamantine , Decamantane, and undecamantane. Figure 2 is a graph showing representative high-grade diamond samples and their molecular weights. The words "diamond-like family" and "tetra-adamantane family" are used to define diamond crystals with the same number. The term "diamond-like composition" of a grid-cage unit &quot; tetramantane component &quot; means any and / or all substituted or unsubstituted diamond-like components equivalent to the tetramantidine component. Hardware adamantane component " The term refers to any and / or all substituted or unsubstituted diamond-like components equivalent to freshly burned components of hardware. The term "non-ionized diamond-like components" refers to the generation of < High diamond The composition, the term "advanced diamond-like composition" in langzhong is as defined in this article. ': Non-isolated ... King Kong firing residue &quot; refers to the electric charge generated during mass spectrometry analysis without any positive charge. Gold grind components. One ': non-ionized metal freshly burned components and diamond-like components higher than freshly burned metal &quot;-cap without the charge generated during the mass spectrometry analysis, such as positively charged pentadecantane components and greater than Advanced diamond-like ingredients of metal adamantane. The "selected advanced diamond-like ingredients" by King "means that it needs to be isolated or" contains this "in the product: Γ species or / substituted or unsubstituted advanced Results :: 2 = stone-like composition "etc. refers to non-selected advanced 19- x 297¾)-This paper size applies to Chinese national standard 1244477 A7 B7

V. Description of the invention (17 fields. Ichioka is used to describe one or more ancient &amp; μ properties that can be obtained as a pure diamond-like ingredient of the same grade-Α 鈒 镫 石 蛘 4 V and is rich in 〃 &quot; Separately ~ ask,., And 1 stone rice ingredients, the original shake 5 々 々, Wang Jian / Chen 钿 at least 25 times, and 0 times the original concentration of the main y. Better &quot; 古 &quot; 古 鍈z: followed by diamonds of the same grade or 丨 丨 containing at least 25% of 冋,., and 1 stone 4κ composition, ^ ιηη〇 /,. r is especially 50% less (that is, 50-100%) 'better at least 75%, and preferably ^, 仏 女 仏 π soil y /. 'Or even at least 99% -1 /, the SA package presents at least 25%, 50%, 7)%, 95% or 99 ° 〆. The purity of the substance. The term "raw material" or "hydrocarbon raw material" refers to the sentence, μ from the source, and the recyclable amount of high-grade diamond-like fe shells. Better, 4 people, the original family contains oil and gas Concentrate, culvert,

The oil derived from oil storage rocks, oil Baishan up M / ;, L Health <oil shale, tar sands and crude oil rocks. This component stone = vs is not necessary)-one or more low-stone stone-like components and non-iron stone = knife ° the latter-generally characterized by including silk at atmospheric pressure is lower and south at about 35 Gt The material of the lowest Buddha's point may also contain impurities such as sediments, metals including nickel, zinc and other seeding materials. 叾 may also contain heteromolecules containing sulfur, nitrogen, etc. All these non-ballast-like materials are included herein As defined in "Non-stone-like ingredients". Non-selective substances, the term refers to the sum of the raw material ingredients that are not "selected high-grade diamond-like" and include ", non-diamond-like ingredients ,, low-grade diamond-like," and "non-selective high-grade diamonds" as defined herein Diamond-like, ...… Exclusion means the method of removing non-diamond-like and / or low-grade diamond-like ingredients and / or non-selection of high-grade diamond-like ingredients from raw materials. This method includes (to name only) size separation techniques, Distillation, steaming at atmospheric pressure or low pressure _______- 20- This paper applies the Chinese National Standard (CNS) A4 specification (210 X 297 public love) 18 1244477 V. Description of the invention (Ionization, adsorption, chromatography, chemistry Extraction, crystallization, etc. For example, eight: Reveal the distillation method for the removal of Jingang &quot; finished and substituted adamantane, di-, amanantane and triamantane from hydrocarbon raw materials. Size separation by membrane separation, molecular sieve, gel layer Analysis, dimensional chromatography, etc. Mind: The word refers to the separation of materials based on the difference in vapor, and it is carried out on the teeth that are obtained in the elevation. In this article, the most: is performed in a vacuum, but it can also be performed at atmospheric pressure. Or progress under high pressure, VI :: means that the materials in the mixture are dissolved by different methods such as: ° Plasma pressure, different chromatographic affinity, etc., which are separated from each other, such as "pyrolysis" and "heat treatment" &quot; heating raw materials or ingredients The atmospheric dust, low pressure or high pressure thermal degradation of temples. &Quot; 科 "'Making-Shao Fen raw materials-one or more ingredients in raw materials are not diamond-like ingredients,-words ^ ^ ^ ^ ^ ^ ^ It ’s not enough to say that you are diamond-like. The composition of Distillation 6, where diamond-like, is the wording of this article: One: It refers to the comparison of the diamond-like quantity found in the original raw materials. Γ At least-part of the high-grade iron stone-like ingredients are found in the raw materials. In the specific example of Che Fujia, beifeng style knife-like ingredients; better, at least about 10 wt% of high-grade diamond ingredients are recycled. At least 50wt0 / 0 high-grade diamond-like ridge knife, and take the repellent material to score, each of which is based on the wt% m diamond sample before processing ~ the total amount of the diamond sample found in the original section. -21-X 297 ^ 5) Paper scale i-mark 1244477 A7

Description of the invention `` B7 chromatography '' refers to any of many conventional chromatography techniques, including (for example only) column or gravimetric chromatography (general or reverse phase), gas chromatography, high performance liquid chromatography, etc. . The term "alkyl" refers to a straight or branched chain saturated aliphatic group generally having 1 to 20 carbon atoms, more preferably 1 to 6 k atoms (lower alkyl group), and generally 3 to 20 carbon atoms. Carbon atoms, and preferably 3 to 6 carbon atoms (,, lower alkyl &quot;) are cyclic saturated aliphatic groups. The terms "alkyl" and "lower alkyl" list foot groups such as methyl , Ethyl, propyl, butyl, isopropyl, isobutyl, first-butyl, second-butyl, n-heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, Cyclohexyl, etc. Interrogated diamond samples are not shown in Figure 1. 'Grade-diamond diamond samples are bridged cyclonaphthenes that have a superb atomic skeleton superimposed on the diamond lattice (Figures 1 and 4), which is adamantane (three Tetramer, pentamer, hexamer, heptamer, octamer, ninemer, decamer, etc. of the ring [乂 j.1.1] or CiqHm, in which all the adamantane units are 3,7 face fusion. Advanced diamond-like samples can contain many alkyl substituents. The structure of these compounds is extremely hard and has the highest stability of any compound of its formula. Tetramanganite has four structures (Figures 2 and 3): two stereoisomers of iso-tetramantane upp], trans-tetramantine pit [12 1], and helix_tetramantine [1 2 3], generally this The more commonly named diamonds are named by Baiaban et al. There are ten kinds of metal rigid tigers (Figure 5), and the molecular formula of nine kinds is C26h32 (molecular weight 344). Three of these nine pairs are stereoisomers represented by the following [12 (1) 3], [123 4] '[1213], and the non-stereomeric adamantane is [12 (3) 4], [1 (2,3) 4]' [12 12 ]. There is also a tighter metal adamane [1231], -22- This paper size applies to China National Standard (CNS) A4 (210 X 297 mm) 1244477

It is based on the molecular formula (: 2 out of 30 (molecular view ,, n, Shi Yi 卞 I JJ〇)). See Figure 4. Hexamantane has 9 different structures (Figure 6), and 28 of its molecular formulas Is C3qH36 (molecular weight J96), and among them, six kinds of ru, ^ are non-drought; ten kinds are f 蘩 &gt;, entry,, s 炅 &lt; τ, &lt; π-adamantane, because of its highly condensed soil-like structure, is also known as Lijin, Ran &lt; 3 kappa-adamantane. Heptamantane basically exists in 160 possible structures and is passed on. The 8d species have molecular formula c34h4G (molecular weight 8) (Figure 7). Seven of these are non-palladium and have no stereoisomers. . In FIG. 7, only one of the two stereoisomer structures of the π-paired palmitrantamidine is shown. "In Qi Zhigang, the molecular formula of 67 species is molecular weight 434), and the molecular formula of" foot species "is C32H36 (molecular weight 420). These ptamantanes have a structure with significantly greater built-in tension, and their stability is rather low, which is not shown in Figure 7. It is in two kinds of molecular formula 4C3qH34 (molecular weight 394) (Figure 7). Octamantane carries eight "diamond crystalline diamond-shaped units" and exists in five molecular weight core structures (Figure 2). Eighteen kinds of octamantane have a molecular formula of C34H38 (molecular weight 446). Figure 8 shows various octamantane isomers of 446 molecular weight. The molecular formula of other octamantane is C38h44 (molecular weight 500). Other octamantane groups C37H42 (molecular weight 486), C36H4O (molecular weight 472) and C33H36 (molecular weight 432) show larger bond tension and relatively low stability. Nonamantane contains six different molecular weights with the following molecular formulas: C42H48 (molecular weight 552), C41H46 (molecular weight 53 8), C4GH44 (molecular weight 524), C38H42 (molecular weight 498), C37H4Q (molecular weight 484), and C34H36 (molecular weight 444) . In addition, decamantane contains seven different molecular weights. Among the ten diamond pits, 'only one is structurally tighter than other ten diamond pits and has a lower internal bond tension' and has a molecular formula of (: 35 out of 6 (molecular weight 456)). Standard (CNS) A4 size (210 X 297 mm)

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k 1244477 A7 B7 V. Description of the invention (21 to Gang, Fan Nang &lt;-Knife formula is CwHy molecular weight 604), c ^ H ^ (molecular weight) 90) C44H48 (knife inside) 76), molecular weight 55)), C4iH44 (molecular weight 536) and molecular weight 496). Undecamantane (Figure n) with molecular formula C) 0H) 6 (knife I 656), C49H54 (molecular weight 642), C48H52 (molecular weight 628), C46H5G (molecular weight 602), hay molecular weight 588), c42h44 (molecular weight) 548), C4iH42 (molecular weight 534), and CmHw molecular weight) have better and worse high-grade diamond-like samples (Figure 2) is based on its internal bond tension and the corresponding stability Λ Huai, Gan Ji = ten &gt; is τ, It reflects the relative concentration of various raw materials. Raw materials The high-grade diamond samples provided by the present invention are easily present in petroleum raw materials only at dilute concentrations. According to the method of the present invention, the material is selected so that the material includes a recoverable amount of one or more selected advanced diamond-like ingredients. Preferably, the material comprises one or more hafnium-grade diamond-like ingredients of at least about, more preferably at least about 25 PPb, and most preferably at least about 100 ppb. Of course, _ is needed. Raw materials with higher concentrations of high-grade diamond-like ingredients can assist in the recovery of these ingredients. Preferred feedstocks include, for example, natural gas condensates with higher concentrations of diamond-like substances and rectification streams. For the latter, the rectification stream includes hydrocarbon streams that can be recovered from cracking processes, state distillation, and coking temples. The best raw materials include Norphlet Fomation from Gdf inch Mex! ⑶ and gas concentrates recovered from Formation in Canada. In its specific example, the raw materials used in the process of the present invention generally include non-diamonds with a boiling point lower than or lower than the selected low-boiling high-grade diamond-like ingredients. -24-

Pei ·· This paper size applies to Chinese National Standard (CNS) A4 ^ (2l0X297 公 221244477) V. Description of the invention (a mixture of stone-like ingredients and one or more high-grade diamond-like ingredients. According to ::::: It can contain the lag point of high-grade diamond samples, etc. ::: Ji stone samples, the lowest beach point for some i recovery is high 睪: Cheng and diamond-like lag points. Tong 3 said.-Normal raw materials, low;. Shi Guangcheng … 'Fu points are about 250: 1 or higher than normal. Second, the concentration is higher than that of high-grade diamonds. One X: then λ, \ Dan, as shown in Figure 18, one jealous 6 h, one stone "/ knife Raw materials also include non-refined stone-like ingredients. Α includes high-grade iron β raw materials 'usual recovery of selected high-grade diamond-like ingredients' because its concentration is lower than non-selected ingredients ^ The raw materials are effective. The method may need to be In turn, ^ hair mouth to select the high-chertite-like ingredients of the dyeing process, the high-level diamond-like general separation method is shown in Figure 12. According to the eye example, the removal of 3 dyes includes distillation raw materials, Remove non-stone-like components, low-grade diamond-like components and others in some cases : The best specific example of non-selected advanced diamonds with the highest diamond-like composition selected from the lowest Buddha point is the distillation of raw materials to obtain about 335t. The gas lift is equivalent to the stagnation point, and it is better to be at 345tjl and the pressure is equivalent. Fractions. In one example, the lower fractions rich in lower diamond-like and low-stagnation non-diamond-like components were overhead and discarded, leaving high-boiling distillates rich in high-grade stones. Of course, you need to understand The temperature of the fractionation point during the distillation process is a function of the pressure sufficient, and the above temperature is preferred for atmospheric pressure. Low pressure makes the bad distillation temperature reach the same fractionation point at a lower temperature, but high pressure will cause the steam to be drilled in the stone. Linear Sample Distillation-25- This paper size is applicable to Chinese National Standard (CNS) A4 (210 X 297 mm) 1244477 A7 B7 V. Description of the invention (23) The temperature is higher to reach the same fractionation point. From atmospheric pressure to low pressure or The pressure / temperature relationship of high pressure is well known to those skilled in the art. Distillation can be operated to fractionate the raw materials and obtain many fractions in the desired temperature range to provide a choice of high-grade diamond-like or high choices at first. Diamond-like clusters. Leaving fractions rich in one or more selected diamond-like or desired special diamond-like ingredients, and may require further purification. The table below illustrates the types of high-end diamond-like distillates that can be used to enrich the top distillate. Representative fractionation point. In practice, it is advantageous to produce a wide range of temperature often containing high-grade diamond 1 stone samples that can be separated together in subsequent separation steps. The fractionation point is best, better, lower, and higher. Lower distillate and higher grade South drill * Stone sample temperature (° c) Temperature (° C) Temperature (° C) Temperature (° C) Four diamonds firing 349 382 330 400 metal rigids 385 427 360 450 ring six King Kong Yam 393 466 365 500 Six King Yam 393 466 365 500 Heptamantane 432 504 395 540 Octamantane 454 527 420 560 Nine Adamantane 463 549 425 590 Ten Kingam 472 571 435 610 Eleven King Kong 499 588 455 625- 26- This paper size is in accordance with Chinese National Standard (CNS) A4 (210 X 297 mm) 1244477 A7 B7 V. Description of the invention (24) Use Southern diamond-like sample lower distillate temperature (° c) higher distillate temperature (° C) Four King Kong Fired 300 430 Five Adamantane 330 490 cyclohexamantane 330 550 hexamantane 330 550 heptamantane 350 600 octamantine 375 610 nonamantane 380 650 decamantane 390 660 eleven adamantane 400 675 It should be understood that due to the addition of substituents, Substituted high-grade diamond samples can accordingly transfer these preferred fractional temperatures to higher temperatures. Other temperature distillations will be used for the desired diamond-like high-purity fractions. Figure 93 provides a further illustration of the pride of interest that can be obtained with single or multiple high-grade diamond-like ingredients. It is also important to understand that the fractionation can be terminated after the top distillate has been removed from the selected high-grade diamond sample. In this case, the iron and stone samples can be separated from the bottom of the tower. Other methods for removing low-grade diamond samples, non-selected high-grade diamond samples (if present), and / or hydrocarbon-based non-diamond-like components include (for illustration only) size separation techniques, atmospheric or low pressure evaporation, crystallization, chromatography, columns Top separation, decompression and so on. The removal method can take advantage of large-sized high-grade diamond samples to separate low-grade diamond samples from them. For example, the use of film size separation technology will make the raw material flow in the film, so that the low-level diamond-like can selectively pass through the film shielding layer, the condition is to select -27- This paper size applies to China National Standard (CNS) A4 specification (210 X 297 mm) 1244477 V. Description of the invention (25 Select the size of the film cover to make it between the low-grade stone-like component and the compound of the South-level diamond-like component. The size of the ruler can be cut to size. The division "wait for Porosity :: specific example t 'removal method provides low-grade diamond-like composition = ΓΓ ratio is not greater than 9: 1; better not greater than π and preferably this ratio = processed raw materials greater than ㈧. Better, remove and drill from raw materials : After 'compared with the amount in the raw material before removal, at least about 10%, more: to: 1520 and preferably at least 90% of the high-grade diamond-like ingredients are left in the raw material order ~ when hexamantanes need to be recovered And high-grade diamond-like ingredients, and when the raw material contains diamond-like ingredients, the raw materials are generally pyrolyzed to remove from the raw materials; a $ hydrocarbon non-diamond-like ingredients. Pyrolysis can effectively concentrate the pyrolysis treatment of raw materials High-quality diamonds, so they are recycled into Possibly (Figure M). Pyrolysis is carried out by subjecting the raw material under vacuum or in an inert gas to a temperature of about 39 (rC, and preferably about 400 to 55 (TC, more preferably about 400) 450 C, and preferably about 410 to 43 (TC for at least a portion of the non-diamond-like ingredients of the effective pyrolysis raw material. The special conditions used are selected such that the recoverable amount is selected by the high-grade diamond sample The ingredients remain in the raw materials. The selection of conditions is familiar to those skilled in the art. It is better to treat the non-diamonds that are at least about 10% of the raw materials to degrade the pyrolysis materials at a sufficiently high temperature period and at a sufficiently high temperature. Sample composition (better at least about 50%, and preferably at least about 90%) (based on the total weight of the final non-diamond-like ingredients of the raw materials before pyrolysis). Compared with the amount in the raw material before pyrolysis treatment, it is at least about 10%. 'Better at least about 50%, and preferably at least -28- This paper size applies to China National Standard (CNS) A4 specification (210X 297 mm) ) 1244477 A7 B7

V. Description of the invention (2S, 90 /. ~ Intermediate reading stone-like components are left in the raw materials after pyrolysis treatment. &Quot; &quot;, &quot; In the removal of low-grade diamond-like and low-buddose hydrocarbons from raw materials Diamonds are cut into knives and pyrolyzed. However, it is important to understand that the order of these procedures can be changed to remove lower diamond samples from the raw material. Fortunately, the pyrolysis procedure for good examples is not necessary. This is due to the high-grade diamond sample. The raw material is high enough so that the processed raw material (after removing the low grade and 'shell water knife') can be directly used in purification technology such as chromatography, crystallization, etc., and later pays for diamond-like components of high grade. However, when the raw material is medium and high grade Diamond-like components have a core concentration or purity that does not reach the level of recovery, then a pyrolysis step should be used. = When using pyrolysis, it is better to use one or more purification techniques for further crystallization, size separation, etc. According to the optimal process expansion ：： Surgery and regional fine hall ^ m take 丨 Wang Huishui 'first put the recovered raw materials into the gravity tube with nitrocellulose and then use a HPLC single-selection diamond with different column selection Sample and crystallized, qualified: grade iron stone. When Grade iron stone concentration is not high enough-i concentration :: may need to be prepared by, for example, gas chromatography with red-sucking gas chromatography: stereoselective (opposite) static phase-step separation. The same performance is also used Liquid chromatography makes it possible to resolve stereoisomers. It is possible to use dry solvents or additives to achieve a high level: if its content is high, it is a stereo-isomer in the form of a stereo-isomer. ： Automatic crystallization of 'he' night and mechanical separation. The standing agent, palm solvent or various seed crystals can be grown and / or added by use. Another clear choice is at the paper scale S?: Fresh (c ¥ s) -29 · 1244477 A7 B7 V. Description of the invention (27) Chemical separation under dynamic or thermal control. Other applicable methods for the analysis of stereoisomers include palm separation, which can be performed using gas chromatography ( GC) (see "Palamic Chromatography", TE Beesley et al., Wlley, Johnsson Sons, January 1998, hereby incorporated by reference), by high performance liquid chromatography (HPLC) and by Superfluid Chromatography (SFC) Technology (see, Ultrasound in Chromatography and Extraction '' RM Smith, Elsevier Scie (nce, December 1997, hereby incorporated by reference). Uses The method of the present invention provides a composition that enhances advanced diamond patterns. These advanced diamond patterns are used in micro- and molecular-electronic and nanotechnology applications. In particular, ' The hardness, strength, stability, and thermal conductivity shown by these molecules, various structural states and multiple attachment positions make possible the precise construction of a rugged, durable, precise device with nanometer dimensions. Figure 15 shows the relative The molecular components (Buckminsterfullerene and carbon nano tube) in the device are sufficient to select the size and shape of the diamond. Southern diamond samples are three-dimensional nanometer-sized units with different diamond lattice arrangements. This can be converted into these extremely hard nanostructures of various shapes and sizes, such as [12 1 (3) 4] hexamantane is ,, T ,, shape, [12 134] is &quot; L ,, shape, [1 (2) 3 (1) 2] is a flat plate having four leaves. [12 (3,4) 12] Heptamantane has a cross-shaped structure while [121234] has an L-shape, and [12312] hexaadamantane has a disc-like structure. [12 13 2 1] Heptamanthin is a disk having a coplanar blade, and [1213 (1) 21] octamantane is a disk having two opposite coplanar blades. [1232 (1) 3] Octamantane is wedge-shaped. [121 (2) 32 (1) 3] Nonamantane has a triangular plate structure. [123 1241 (2) 3] Decamantane is the perfect octahedron -30- This paper size applies Chinese National Standard (CNS) A4 (210 X 297 mm) 1244477

^ And [丨 2123 1212] Octamantan has a rectangular plate-like structure. U ^ U, 2) 42 143] Elundantane has a long and narrow pyramid shape. In the application of nano technology and nano structural materials, various other shapes can be used according to its special shape. J 1 &gt; II, A, diamond grade. The carbon skeleton structures of tetramantane to undecamantane are shown in Figs. 3 to 1 丨. Diamonds of the same grade also contain a series of rod-shaped structures of different lengths. Order &quot; 1? 1 &quot;,-Ashikata is the first group of this rod-shaped structure series' [1212] Hardware just burned as the next group, followed by [12121] Six adamantane, etc., the additional diamond Will increase the length of the rod by about 0.3 mm, and the length of [1212] metal adamantane is about 1.1 nm. [1 (2) 3] tetramantane is a smaller series, with a flat pyramid structure above (Figure 3) ° [1 (2,3) 4] Hardware adamane (Figure 5) is a perfect tetrahedron pyramid in this form. Southern diamond samples also include spiral structures of various lengths. The first palm-like diamond pattern was tetramantane of order 123. The stereoisomer of 123 tetramantane is sufficient as A &amp; B. Its structure can also be modified in the order of Balaban nomenclature.] And 124 ° These two diamonds have left (counterclockwise) and four diamonds 垸 A, and right (clockwise) (tetradamantane B) directions of rotation or spiral. Like structures, both of which represent partially rotating spirals. Unfortunately, Balaban's nomenclature and helmet method is only a method for distinguishing left and right spirochaetes, which only proves to contain two forms. This sequence is continued in the order 1234 and 1243 (that is, eight and ⑴) for metal adamantane (Figure 5), and 12341 and 1243 1 (that is, A and B) for hexamantane (Figure 6) and so on. Six diamonds The alkane component contains left and right spirals of these helical nanostructures that are fully rotated (Figure 94).

1244477

A7 B7 V. Description of the invention (29) These special structural features constitute high-level diamond samples separated from acrylic acid molecules, cyclic systems, and even bridged cyclic equivalents. The large stability, nanometer size, and different hardness shapes fully define the 5 large distances of the attached non-planar bridge head placement, forming its unique characteristics. Due to the hardness of advanced diamond-like components, the three-dimensional shape and nanometer size of the special couple shape, it is hoped that constructable molecules can be aggregated and formed into an array of blocks that can be constructed and synthesized unprecedentedly, and can be seen in molecules Electronic computing device, small-sized machinery such as molecular automatic control and self-replicating manufacturing system. In contrast, the South-level diamond samples can be used as coatings, thin film layers, and other new materials with special chemical photoelectricity and thermal conductivity for applications that require diamond-like quality. This article reveals the novel uses of advanced diamond-like substances in microdomains. Specific examples include (but not limited to) thermally conductive films in integrated circuit packages, low-k dielectric layers in multilayer connections of integrated circuits, thermally conductive adhesive films, conductive 4k films in thermoelectric cooling devices, and integrated circuit devices ( 1C) passive film and electric field emission cathode (In addition, these advanced diamond samples can also be used for South-South viscosity coefficient and extremely low flow point 1 'South-quality lubricating fluid. When used, these fluids include lubricating viscosity and From about 0.1 to 10 wt% of diamond-like fluid. 0 In addition, these high-grade diamond * stone samples can be used as a South Density fuel in the manner described by Chung et al. 14 and are hereby incorporated by reference. The following examples are provided to illustrate the present. This invention is not intended to limit the scope of the invention in any way. Unless otherwise stated, all temperatures are in ° C. Examples As used herein and in the drawings, the following abbreviations are as follows. Any abbreviations not defined below are General Voice -32- This paper size applies to China National Standard (CNS) A4 Grid (210 X 297 mm) 1244477 A7 B7 V. Description of the invention (30) API II: American Petroleum Institute atm eqv =: atmospheric equivalent btms II: bottom EOR Traps II: operating end point fid II: flame oxidation Detector g =: gram GC II: gas chromatography GC / MS II: gas chromatography / mass spectrometry h =: hour HPLC-: south performance liquid chromatography HYD RDG:: hydrometer reading L II: liter min =: Minutes mL = milliliters mmol = = millimoles N II: nominal p A:: pico amps ppb = = ppm per billion parts: = RI per million parts = refractive index SIM DIS = simulated steaming hall ST = = Initial TIC: = Total Ion Current TLC: = Thin Layer Chromatography-33- This paper is sized for China National Standard (CNS) A4 (210 x 297 mm)

1244477 A7

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1244477 A7 B7 V. Description of the Invention (32) Example 10 describes the enrichment and isolation of the nonamantane component. Example 11 1 describes the enrichment and isolation of the decamantane component. Example 12 describes the enrichment and isolation of the undecamantane component. It should be understood that the order of the various distillation, chromatography, and pyrolysis steps can be changed, but the order listed in Example 1 is the final result. Example 1 This example has seven steps (see the flowchart in Figure 12). Step 1. Select raw materials. Step 2. GCMC analysis and development. Step 3. Atmospheric vaporization of raw materials. Step 4. Vacuum distillation of residues in the Daqi steaming hall. I. Step 5. Pyrolysis step of single fractions. 6. Aromatic and Steps for removing polar non-diamond-like constituents. 7. Multi-column HPLC separation of high-grade diamond samples. A) First selective first column to provide fractions rich in specific high-grade diamond samples. B) Different options. The second example is the high-grade diamond sample that provides a single ion. This example is for a single ion of multiple hexamantanes. As shown in Example 5-12, it can be easily used to isolate other high-grade diamond samples. Step 1-Selection of raw materials Obtain appropriate starting materials. These materials include gaseous concentrates, raw material A (Fig. 16) and petroleum-containing gas concentrates, and raw material B. Although the layer uses other concentrates, petroleum, or refined fractions and products, these two materials are selected because of the high diamond-like concentration determined by GC and GC / MS (approximately 0.3 -35- This paper scale applies to Chinese national standards (CNS ) Α4 size (210 X 297 mm) 1244477

wt% high-grade diamond-like) ^ The two raw materials are light-colored and the Aρι specific gravity is 19 to 20 API. Step 2-Development of GC / MS Analysis Use gas chromatography / mass spectrometer to analyze raw material A to determine the target advanced diamond sample and provide the GC residence time of these target substances. Use this information to track individual target advanced diamond patterns through subsequent single-off procedures. Figure 13-8 is a table listing the GC / MS analysis information of general hexamantane (GC residence time, molecular ion (from +) and basic peak). The table (Figure 13A) also contains similar GC / MS analysis information for other advanced diamond samples. Although the Gc dwell time is about constant, it is not used for reference (the dwell time will change with time. It is recommended that when the GC dwell time is detected to change, the Gc / Ms * analysis value should be corrected for a certain time. Step 3 -Distillation of raw material atmospheric distillation Distills the sample of raw material B into many boiling-point-based fractions to separate low-boiling components (non-diamond-like and low-grade diamond-like), and further concentrates in each fraction and covers special high-grade Diamond sample. 2. Raw materials of different samples. B: The yields of atmospheric distillation fractions are listed in the table below, and compared with the simulated distillation yields. 3. As can be seen from Table 1, the simulated distillation data is consistent with the actual distillation data. The simulated distillation data is used to plan the subsequent distillation process. -36- 1244477 A7 B7 V. Description of the invention (34) Table 1: Yield distillation (° F) simulation of the atmospheric distillation fraction of raw material B in two different operations Estimated Distillation Yield (Wt%) Raw Material B (Operation 2) Yield (Wt%) Difference to 349 8.0 7.6 0.4 349 to 491 57.0 57.7 -0.7 491 to 643 31.0 30.6 0.4 643 and higher 4.0 4.1 -οι Fraction (° F) Estimated Yield (Wt%) B (Operation 1) Yield (Wt%) Difference to 477 63.2 59.3 3.9 477 to 515 4.8 7.3 -2.5 515 to 649 28.5 31.2 -2.7 649 and higher 3.5 2.1 1.4 Step 骡 4-Vacuum distillation residual atmospheric distillation distillation The atmospheric distillation residue of the raw material B obtained in step 3 (including the original raw materials of 2-4% by weight) is distilled into fractions containing high-grade diamonds (as shown in Figures 17 and 93). The input is atmospheric pressure 650 ° F + tower bottom. The complete distillation data of Raw Material B is listed in Tables 2A and 2B. Tables 3A and 3B show the raw material B 650 ° F + steam tower data of the steam tower bottom.- 37- This paper size applies to China National Standard (CNS) A4 (210 X 297 mm)

1244477 A7 B7 V. Description of the invention (35) Table 2A. Distillation data of raw material B

Raw Material B: Column used: clean 9 "X 1.4 &quot; bump filled with steamed copper 1 hexadecimal nominal fraction steam temperature weight volume API density WT volume WT volume start-end G ml @ 60 ° F 60/60 @ 60Τ PCT PCT PCT PCT 1 226-349 67.0 80 38.0 0.8348 7.61 .8.54 7.39 8.26 2 349-491 507.7 554 22.8 0.9170 57.65 59.12 55.98 57.23 3 491-643 269.6 268 9.1 1_ ⑻64 30.62 28.60 29.73 27.69 Column retention 0.2 0 6.6 1.0246 0.02 0.00 0.02 0.00 BTMS! I 643 + 36.1 35 6.6 1.0246 4.09 3.74 3.98 3.62 EOR carrier 0.0 0 0.00 0.00 0.00 1 Total 880.6 937 100.00 100.00 97.09 96.80 Loss 26.4 31 2.91 3.20 Feed 907.0 968 19.5 0.9371 100.00 100Ό0 Loop back API and density 19.1 0.9396 Table 2B: Distillation data of raw material B

Raw material B: used column: clean 9 ”X 1.4 &quot; pressure reflow fraction volume mi_T weight G specific gravity steam POT torture ratio no observation 60T VLT atmospheric equivalent hydrogen reading temperature 93 225.8 262 50.000 3: 1 Starting column top 198 349.1 277 50.000 3: 1 1 80 67.0 39.6 80.0 38.0 321 490.8 376 50.000 3: 1 2 554 507.7 24.1 80.0 22.8 Fraction in the downflow tube 2 Milky, white crystalline, anti-drop Apply heating lamp cooling in the tube and move to the bottom to the smaller bottle 208 437.7 323 10.000 3: 1 Starting column top 378 643.3 550 10.000 3: 1 3 268 269.6 | 9.9 75.0 9.1 Switch off the operation carrier end due to drying 0 0.0 Distillation volume 902 Column retention 0 0.2 0.0 0.0 6.6 Column bottom 1 35 36.1 7.2 72.0 6.6 Recovery 937 880.6 Feed 968 907.0 20.7 80.0 19.5 Loss 1 31 26.4 -38- This paper size applies to China National Standard (CNS) A4 specifications (210X 297 mm) 1244477 A7 B7 V. Description of the invention (36) Table 3A: Vacuum distillation data of raw material B Raw material B-atmospheric distillation residue 650 Ten-column column used: Sarnia Hi Vac temperature. F pressure reflux volume volume ml weight G API specific gravity VAPOR POT butORJR ratio no observation 60T steam atmospheric equivalent 60 ° F hydrogen reading temperature T 315 601.4 350 5.000 start Differential pressure 344 636.8 382 5.000 300 Read 342 644.9 389 4.000 500 Read 344 656.3 395 3.300 1 639 666.4 7.S 138.0 4.1 353 680.1 411 2.500 400 Read 364 701.6 430 2.100 2 646 666.9 9.4 138.0 5.6 333 736.0 419 0.400 200 Read 1 336 751.9 432 0.300 3 330 334.3 12.4 139.0 8.3 391 799.9 468 0.500 4 173 167.7 19.0 139.0 14.5 411 851.6 5⑻ 0.270 5 181 167.3 26.8 139.0 21.7 460 899.8 538 0.360 6 181 167.1 27.1 139.0 21.9 484 950.3 569 0.222 7 257 238.4 26.2 139.0 21.2 Turn off the distillation to check the temperature of the cylinder (5.3 g of the carrier material discharged) 1 472 935.7 576 0.222 Initial pressure difference 521 976.3 595 0.340 8 91 85.4 23.7 139.0 18.9 527 999.9 610 0.235 9 85 80.8 23.0 139.0 18.2 527 1025.6 624 0.130 10 98 93.8 21.6 139.0 16 .9 16.5 grams of emissions left half K ~ 4 grams of water) 1 1 1 ME) AND operation carrier end 20 17.8 (mathematical combination) volume distillation 2701 column stay 4 4.0 0.0 0.0 3.4 column bottom 593 621.8 11.0 214.0 3.4 recovery 3298 3311.7 Feed infusion 3298 3326.3 18.0 234.0 8.6 Loss 1 -5 14.6 -39- This paper size applies to Chinese National Standard (CNS) A4 (210 X 297 mm) 1244477 A7 B7 V. Description of the invention (37) Table 3B : Vacuum distillation data of raw material B Raw material B-atmospheric distillation residue 650 ° F + column bottom: Sarnia HiVac fraction vapor temperature weight volume API density WT VOL WT VOL start-end G ml @ 6〇 60 60 60 ° F PCT PCT PCT PCT 1 601-656 666.4 639 4.1 1.0435 20.12 19.38 20.03 19.40 2 656-702 666.9 646 5.6 1.0321 20.14 19.59 20.05 19.62 3 702-752 334.3 330 8.3 1.0122 10.09 10.01 10.05 10.02 4 752-800 167.7 173 14.5 0.9692 5.06 5.25 5.04 5.25 5 800-852 167.3 181 21.7 0.9236 5.05 5.49 5.03 5.50 6 852-900 167.1 181 21.9 0.9224 5.05 5.49 5.02 5.50 7 900-950 238.4 257 21.2 0.9267 7.25 7.79 7.17 7.80 8 950-976 85.4 91 18.9 0.9408 2.58 2.76 2.57 2.76 9 976-1000 80.8 85 18.2 0.9452 2.44 2.58 2.43 2.58 10 1000-1026 93.8 98 16.9 0.9535 2.83 2.97 2.82 2.98 Tube Column retention 4.0 4 3.4 1.0489 0.12 0.12 0.12 0.12 BTMS 1026 + 621.8 593 3.4 1.0489 18.78 17.98 18.69 18.01 Carrier 17.8 20 0.54 0.61 0.54 0.61 1 Total 3311.7 3298 100.00 100.00 99.56 100.15 Loss 14.6 -5 0.44 -0.15 Feed 3326.3 3293 8.6 1.0100 100.00 moo Calculated API and density 9.4 1.0039 Table 4. Analysis of the elemental composition of raw material B based on raw material B65 (TF residue based on the measured value of nitrogen 0.991 wt% sulfur 0.863 wt% nickel 8.61 ppm vanadium &lt; 0.2 ppm table 4 Explain that part of the elemental composition of the gas distillation (650 ° F) residue of raw material B contains some of the same impurities. Table 4 shows the weight percent of nitrogen, sulfur, nickel and vanadium in the atmospheric distillation residue of raw material B. The subsequent steps are to remove these substances. Step 5-Pyrolysis of single-departures -40- This paper size applies to China National Standard (CNS) A4 (210 X 297 mm) 1244477

The Nanwen reactor was used to heat the non-diamond-like stone samples in the 1 "," distillate. The pyrolysis process is shown in Figure 18A. Analysis. Comparing these chromatography shows heat "Removal" The concentration of high-grade diamond-like samples increased significantly; a 500-ml PARR® PAR reactor from Mo Line, Illinois was used in this step. Step 6-Removal of systemic and polar non-adamantine components Pass the pyrolysis product of step 5 through a silica gel chromatography tube (using cyclohexane as a dissolution solvent) to remove neutral compounds and asphaltenes (step 6, Figure 12) . Silica gel soaked with silver nitrate (10 wt% AgNO3) was used to remove the free aromatic and polar components to obtain a cleaner diamond-like fraction. However, it is not necessary to use this chromatographic aromatic separation method to assist subsequent steps. Step 7-Multi-column hplc for advanced diamond-like separations. An excellent method for single ion-purity diamond-like purity is the use of continuous different selectivity two or more HPLC columns. The first HPLC system contained a Whatman M20 10/50 ODS column operating in series at 5.0 ml / min using acetone as a mobile phase. Take a series of HPLC fractions (see Figure 19). Fractions 36 and 37 were combined and further purified on a second HPLC system. The combined fractions (36 and 37) contain hexamantane # 7, # 11 and # 13 (Figure 19, see also Figure 13B). The further purification of the combined ODS HPLC fractions was performed using a paper size different from the above-mentioned ODS column and having different selectivity in various hexamantane. The Chinese paper standard (CNS) A4 (210 X 297 mm) was applied. 1244477 A7 B7 V. Description of the invention (39)

Hyp ere arb static phase HP LC column was achieved. Figure 20 shows the dissolution time of each six diamond, j: completion on a Hypercarb HPLC column with acetone as the mobile phase. The differences in dissolution time and dissolution order of hexamantane on ODS and Hypercarb HPLC columns can be seen in Figures 19 and 20. For example, hexamantane # 11 and # 13 dissolve together in the ODS HPLC system (see Figure 19), but in different libraries on the Hypercarb system (Figure 20) (Gufen 32 and 27, respectively). The different dissolution order and time of the advanced diamond samples selected on these two systems can be used to separate co-dissolved advanced diamond samples. It can also be used to remove impurities. Using this method on the combined ODS HPLC fractions 36 and 37, the appropriate Hypercarb HPLC fraction can be taken out, thus obtaining high-purity hexamantane # 13 (Figures 51A and 51B). Other ODS HPLC fractionation and Hypercarb HPLC fractionation points can be used to isolate the remaining hexamantane. This single ion strategy objection is used for other advanced diamond * stone samples, but can change the dissolution solvent composition. ODS and Hypercarb columns can also be used in the reverse order of these single isolations. By using the above method, and using Hypercarb or other applicable column, the branch library contains six diamonds, and the collection at a comparable dissolution time will result in a single isolation of the remaining six diamonds with high purity. This is also true for other high-grade diamond samples ranging from four diamond gauges to eleven adamantane, including substitution forms. Example 2 Steps 1, 2, 3, 4, 5, and 6 (Figure 12) of Example 1 were repeated, followed by different steps 7 below. Step 7: Siphon gas chromatography for the preparation of two-column columns. Example 1-Product of Step 6-42- This paper is sized for China National Standard (CNS) A4 (210 X 297 mm) 1244477 A7 B7 5. Description of the invention (40) Hexamantane is isolated. The fractionation time of hexamantane was determined using the residence time and pattern of Gc / ms analysis (Example 1, Step 2), and was set to D B -1 equivalent for the first preparation siphon G C g column 'methyl crush g. The results are shown in Table 4 2A, and the results are shown in Figure 42A. Two of the six ingredients containing the raw material B were taken out and confirmed as &quot; gu share and sent to the second column of the column 2 &quot;. The spare siphon gas chromatography used was manufactured by Gerstel, Inc., Baltimore, Maryland, USA. Use the first column to concentrate the higher diamond sample, such as hexamantane, by taking out the fractions that are sent to the second column (see Figure 42B for hexamantane # 2 and # 8). The second column (phenyl-methyl silicone, DB-17 equivalent) was used to further separate and purify the hexamantane, which was then used for the single isolated peak of the target, and it was left on the unique support 1-6). The remaining part of the GC carrier 1 contains the crystals of Six King Kong Yuan # 2. GC carrier fraction 3 contains crystals of hexamantane # 8. Subsequent GC / MS analysis of the carrier gas # 1 substance (Figures 43A and B) showed that the GC / MS analysis of step 骡 2 prevailed as 鬲 purity hexamantane 42. Similarly, GC analysis of the substance in carrier # 3 (Figures 44A and B) showed that it was the major hexamantane # 8. Photographs of the π-adamantane # 2 and # 8 crystals (analysis in Figures 43 and 44) are shown in Figures 45 and 46. This procedure can be repeated to separate other hexamantanes. This also applies to other fine diamond patterns. Example 3 Steps 2, 3, and 4 of Example 1 were repeated using raw material A (Figure 12). Step 4 The non-diamond-like content of raw material A in the recovered atmospheric residual fraction is particularly low. The pyrolysis step of Example 14 can be omitted, especially when the high-grade diamond samples sought are tetramantane, metal adamantane and cyclohexamantane. In this example, the content recovered in step \ is directly used in steps 6 and 7 in example i, and &amp; is directly sent to -43-1244477 A7 B7 41 in Example 2 5. Description of the invention (v step 7 (Figure 1 2 ). The change of this process can be used for the raw material B. The remaining portion of Vajrayon's burnt '. However, when it contains obvious non-grade stone-like ingredients = required; pyrolysis. (Figure 17) was obtained from this raw material. This fraction was prepared by a process similar to that shown in step 7 of Example 2 to prepare a part of the distillation by siphon gas chromatography (see Figure 12). For column preparation, siphon gas chromatography was used. Tube I chromatography was used to clean the distillate fraction from the target tetramantane (step 6, figure! Y. Residence time and pattern used (example! Step 2). The siphon g-pillar methyl silicone DB_1 is set to the remaining time of the target diamond sample (such as tetramantane). The result is shown in the upper part of Fig. 21, and is the same as that in the museum. 2: 用 用 第-管Column 'by taking out and then sending it to a second column (phenyl-methyl: the same, DB] Jing, etc.) to concentrate the target diamond-like sample (such as four diamond-like firing diagram one Xia Wan) The second king further separated and purified the target stone sample, then: into the sole M carrier (carrier "6). The GC carriers 2, 4 and 6 contained the remotely selected tetramantane (Figure 21). Then, the South Concentration Si King Kong was examined as ancient solution, and it was crystallized or dissolved in the solution carrier Γ7Λ.

Carriers 2 '4 and 6; See ... Under large microscope, the preparation GC is not high enough to cause crystallization (see Figure 22). When the concentration is • and the day is produced, it needs to be further concentrated by the preparation GC. … Can be used to separate other advanced diamond samples from raw material A.

Example 4 · GC for the preparation of HPLC fractions. Ten to seven to adamantane, eight gold steel salts, and high-grade diamond samples, etc., may need to be -44- mm) — 1244477 V. Description of the invention (42 # 分 余 例 I 2. The HPLC product obtained in step m% 7. This can be prepared by using :: = chromatography, as in Example 2, step ™. Use the prepared ingredients to enter 4κ into a knife and crystallize ... from raw materials A and B-to And all four adamantane, Jiuzhe 3441 6 factory, Luke β early leave <all metal adamane (Moore J44), separated from the raw material B-two (旲 ear wt original two β separated + into. — / 、 Crystallization (mole wt 396); and from crystallization of adamantane (mole wt 394), isolated from raw materials

The crystals of octamantane (Morphelanaceae B alkane grade day and Nine gold from raw material 8 :: "Wuxi 98" and ten adamantane crystals (Mole) '. And scale-like components are also ^ Using these actual shots, the list of single-off rewards Example 5A: The single-off of tetramantane: The general process of Examples 1 and 2 is rich in and single-off of tetramantane. In the ancient example, it is not used Pyrolysis step 5 (Figure 12), and step 4 = f column chromatography (step 1 of Example 1 followed by the following = column chromatography product: again ig points: jin step 6 column chromatography column eluate, To determine the approximate dwell time of the tetrakimanta chimera structure. The tetramantine alone is numbered according to its dissociation order in C ^ C / MS analysis. Use this reference number to confirm the individual tetramantine burning in the subsequent step. It is important to understand that the stereoisomer pairs were not separated in this analysis, so the purpose of these stereoisomers (racemic mixtures) needles is numbered. The GC residence time varies with the column, and 0. Below In Example 5D. Tetra Adamantane Reference # 1 2—GC / MS Dwell Time (min) 11.28 nil Cleaning -45- column chromatography paper waves this scale applicable Chinese National Standard (CNS) A4 size (210 X 297 mm) I244477

A7 B7 Description of the invention (The distillation fraction of 43 is isolated from tetramantane. The results are shown in Figure 21 and confirmed as Gus 1, 2 and 3. Using the first column, take it out and send it to the second tube. The fraction in the column was concentrated in the tetramantine pit (see Figure 2 1). The second column (phenyl-methylsilicone, DB-1? Equivalent) was further separated and purified, and then sent to the separate In the vial (carriers 1-6). Collect GC carriers 2, 4 and 6 and further process. Then crystallize the tetramantane concentration of tritium from the solution. Under a microscope magnified at 30 times, prepare a GC carrier for distillation. Crystals can be seen in parts 2, 4 and 6 (see Figure 22). When the aging time is not enough to crystallize, it needs to be further concentrated with preparation. Figures 22A, B and C illustrate the carrier # 2, # Tetramantane (equivalent to tetramantane # 1, # 2, and # 3, respectively, isolated from raw material A in 4 and # 6 (respectively crystallized photos. After obtaining crystals of appropriate size, the structure of the substance is determined using X-rays. The stereoisomeric tetramantane can be further separated and its two components can be removed as described previously. Κ Example 5B · Using pyrolysis to contain tetramantane is less Pyrolysis can be used for tetramantane single ionization (step 5, example 1. Figure 12). The following distillate, its composition and before pyrolysis, contain tetraamantane distillate (steam leftover pyrolysis makes non-diamond-like components Solid. As shown in Figure 23B, fraction 1 is similar, Figure 17) contains non-diamond-like. The gas removed from the solution and non-diamond-like peaks after pyrolysis of coke-like disappeared. Under vacuum at 45 ° C The pyrolysis rich in tetramantane is heated in the reactor, and the distillation fraction is performed for 20.4 hours -46-

1244477 A7 B7 V. Description of the invention (44) Example 5C: Single HPLC system using a single diamantane diamond sample Single HPLC using HPLC In addition to the above gas chromatography and pyrolysis methods, HPLC can also be used to obtain a sufficiently enriched Adamantane to crystallize. Appropriate tubing used is known to those skilled in the art. In some cases, this purification can be performed by reverse phase HPLC using acetone as the mobile phase. The preparation of the raw material A, the gas concentrate, and the distillation fraction equivalent to the fractional point of the fraction # 1 was performed by HPLC (FIG. 17), and the color chromatogram was recorded. Nine distillates were taken out during the operation. The HPLC column used was 25 cm x 10 mm I.D. Vydac octadecylsilane ODS columns are operated in series (Vydac columns are manufactured by CA. Separations Group, Inc., USA). A 20 ml sample of a solution containing tetramantane fraction at a concentration of 55 mg / ml was injected into the column. The column was run using 2.00 ml / min of acetone as a mobile phase carrier. Figure 24 (A, B) compares the gas chromatography of the starting material (Figure 24A) with HPLC fraction # 6. Compared to the starting material, HPLC fraction # 6 is obviously rich in tetramantane. Figure 24B (Figure 24B compared to the starting material (Figure 24A)). The concentration of the four adamantine # 2 in HPLC fraction # 6 was just enough to crystallize it. Example 5D: Tetramantane isomers isolated by HPLC alone. Using multiple columns with different selectivity. As described in Example 5C, tetramantane can be isolated by HPLC. In this example, HPLC columns with different selectivities were used to isolate the tetramantane isomers alone. Figure 25 shows the preparation and separation of tetragamantane using an octadecylsilane (ODS) HPLC column with acetone as the mobile phase. The distillation product used as a starting material in Example 5B was used as a starting material. In particular, it is carried out at about 650 ° F -47- This paper size applies to China National Standard (CNS) A4 (210 X 297 mm)

Pretend

1244477 A7 B7 V. Description of the invention (45) Raw material B The fraction left by atmospheric distillation is prepared by HPLC fractionation. The first column contains Whatman M2 0 10/5 0 (x2) ODS tube (@ 590 psi) in tandem using 5.00 ml / min of acetone as a mobile phase. 56 mg / ml containing 0.500 ml of injection The lower fraction was acetone. The resulting chromatogram is shown in Figure 25. In the HPLC system (Fig. 25), tetramantane # 1 was first dissolved, then tetramangan # 3 was dissolved, and finally, tetramangan # 2. The detector used is a differential refractometer. From this operation, Gufen 12 (Figure 25) was removed for further purification. Further purification of fraction 12 was achieved using a different Hypercarb-S HPLC column from the ODS column described above to isolate tetramantane # 2 (Figure 26). Two Hypercarb-S columns (manufactured by Penn. Thermo Hypersil, USA), 4.6 mm ID X 250 mm, using 1.00 ml / min acetone as mobile phase in series operation (@ 180 psi), 50 ml 4 mg / ml acetone injection The liquid also uses a differential refractometer. On the Hypercarb HPLC system (Figure 14), tetramantane # 3 was first dissolved, then tetramantane # 1, and finally tetramantane # 2. Tetramantane # 2 was fractionated from this HPLC operation (Figure 26), and its purity is illustrated in Figures 28A and B. Hypercarb HPLC was performed on six portions of ODS HPLC to isolate all tetramantane (stereoisomers were separated by the para-HPLC method). Figure 27A shows GC / MS total ion chromatography (TIC) of an HPLC fraction containing tetramantane # 1; and Figure 27B below shows its mass spectrum. Figure 29A shows the GC / MS total ion chromatography (TIC) of the HPLC fraction of Handan from tetramantane # 3; Figure 29B below shows the mass spectrum. Example 5E: Monoalkylated tetramantane of substituted tetramantane. Non-alkylated tetragold can be obtained from Examples 5A to 5D.-48- This paper is applicable to China National Standard (CNS) A4 (210 X 297). Centimeter) 1244477

Description of the invention (46 The method described in the just-fired method is used for separation. Figure 30 shows a molecular weight of 306, and the molecular ion of the mass spectrum is m / z ^ 06. The methyl mass spectrum of the ion (where the tetramantane is shown) is lost. The k-based compound is isolated with Hypercarb HpLc, and the π-pillar time in the gc / ms system is u 46 minutes (Figure 3). It may require the use of extra-maxillary 4 HPLC for separation or preparation of Gc (as in Example 3 and sentences, with a single-isolated part of fluorene-based tetrahydropyrrolidone. Example 6A to prepare a gas-chromatographic single-isolated hard-metal die-fired powder, repeat the steps of Example 1. Step K4 (Figure 12). According to step 5, under a vacuum of 450 Torr ... 5.2 grams of raw material B 65〇ρ + bottom distillation fraction 5 (Table 3, Figure 18) took 16.7 hours. Then an example 1 step 6 Process the product. GC / MS analysis of the eluate from column chromatography (step 6) to determine the GC dwell time of isomers of isomers of amantadine. The components of adamantane with a molecular weight of 344 are analyzed by GC / MS. The dissociation sequence number in the following. Then use a two-column preparation with siphon gas chromatography to produce from step 6 above: early leaving metal adamane. Column The results show that the metal alkane # in the ketone 31 # 卜 = 1 沉 ^ Shen Xue, which contains the metal gang gauge # 1, is called in Figure 31, and the peak fraction is sent to column 2 &quot; The first-tube 纟 'is taken out and then sent to the second column of Gu Fennong = Jingang m. The second column (phenyl · fluorenyl second ketone, db_i7 equivalent) into the binocular: it is also the material separation And the purified metal was just burned # 1. The material sent to the carrier 1: 1: Λ ”was sent to the GC carrier remainder 6, where it was collected = 冈, the crystal (see Figure 31B). The carrier # 6 substance The Secret Separation (see Figure 32) shows (Refer to 49- 1244477 A7 B7 for the hardware burned according to the Gc program for preparation. V. Description of the invention (47) GC / MS dwell time system) The dwell time shown by # 1 is 16.233 minutes. Figures 32A and B show the high-purity metal adamane # 1 recovered from the GC carrier 6. The procedure can be repeated. Pairs, which can be separated using palladium HPLC or other analytical techniques. Highly concentrated metal adamantane crystals can be added directly to the carrier or added from solution. Under the microscope, the crystals of metal adamantane # 1 can be seen in the preparation GC carrier 6 (see FIG. 33A). These crystals are preferably transparent and show a high refractive index. It does not exist. When the concentration is not high enough to crystallize, it needs to be further concentrated by GC for preparation. Figure 33B is a photo of two kinds of metal adamantane co-crystallized in the GC carrier for re-preparation. After obtaining the crystals of appropriate size, The structure of non-stereoisomer metal adamantane was determined using X-ray winding. Stereoisomerized metal adamantane can be further separated into two components. Example 6B: Repeat steps 1-6 of Example 6A with HPLC single ion hardware adamantane. The GC / MS analysis reference number and residence time of 344 molecular hardware amantane are as follows. Hardware adamane reference # 1 2 4 5 6 GC / MS residence time (Minutes) 13.68 15.26 15.31 15.72 15.85 16.06 * (HPoMS, 0.25 micron film, 0.25 mm ID X 30 m, helium carrier gas) Use 1 ^ 96 &quot; ^ &amp; to make 1 ^ 1 ^ (Figure 35) for further purification Figure 34 Contains five to 50-This paper size applies to Chinese National Standard (CNS) A4 specifications (210 X 297 mm)

Binding

1244477 A7 B7 V. Description of the invention (48) Adamantane # 1〇DS HPLC fraction, isolated from metal adamantane # 1 alone. Figure 14 shows how the combination of ODS HPLC and Hypercarb HPLC can be used to separate the remaining hardware. ODS and Hypercarb columns are also used in the reverse order for this single isolation. FIG. 36 shows GC / MS total ion chromatography (TIC) of singly isolated metal adamantane # 1. The lower half of Figure 36 illustrates the mass spectrum of the metal adamantane # 1 GC / MS peak. As illustrated in Figures 14 and 34, the various remaining ODS HPLC fractions contain other hardware. By using a similar method as described above, that is, using Hypercarb (as shown in Figure 14) or using another suitable column to fractionate the fraction containing hardware adamantane ODS, and collect it at an equivalent dissolution time, the remaining hardware adamantane is obtained The high-purity dissolution is shown in Figure 37-41. In particular, Figure 37 illustrates GC / MS Total Ion Chromatography (TIC) and mass spectrometry using two different HPLC columns for single ionization. Figure 38 illustrates metal pentane single ionization using two different HPLC columns. GC / MS Total Ion Chromatography (TIC) and Mass Spectrometry of # 3; Figure 39 illustrates GC / MS Total Ion Chromatography (TIC) and Mass Spectrometry of Jane # 4 using two separate HPLC columns. 40 illustrates GC / MS total ion chromatography (TIC) and mass spectrometry of metal gangane # 5 using two separate HPLC columns; and FIG. 41 illustrates metal gang 'Jane # 6 using two different HPLC columns. GC / MS total ion chromatography (TIC) and mass spectrometry. GC / MS does not separate the stereometallic adamantanes, and therefore a single number represents these stereoisomeric pairs. These stereoisomeric pairs can be separated by the palm separation method. In addition, as described earlier, the metal adamantane condensed isomers having a molecular weight of 330 are more steric and exhibit a significantly lower concentration. This pentamantane component was found by GC / MS analysis of the pyrolysis product of distilled fraction 5 which was removed using step 6 of Example 1 (Fig. 12). In the analysis of Example 1 and Step 4, the metal adamantane component dissolves at 14.4 minutes, and this example can be used. -51- This paper size applies to China National Standard (CNS) A4 (210 X 297 mm) 1244477 A7 B7 5. The procedure in the description of the invention (49) is separated. Example 6C. Purification of Substituted Metal Gangane Substituted metal gangue is present in raw materials A and B. Substituted pentamantane can be enriched with these starting materials and purified using the method described in the non-alkylated hardware adamantane in Examples 1-4. The molecular weight of the monomethylated metal adamantane rich in this example is 358 (the obtained molecular ion of the mass spectrum is! N / z 358, and it shows the loss of the methyl mass spectrum of the ion index of the m / z 343 spectrum of the metal adamantane step. ). The alkylated compound is enriched in ODS HPLC Fraction # 31 and can be separated by additional HPLC or further purified by preparative GC procedures to form crystals (as in Example 3). Example 7 A: Isolation of Six Amantadine Components The purpose of this example is to demonstrate that the procedure can be used to enrich and isolate 39 types of hexaamantanes. The process of Example 1 was repeated with the following changes. In step 骡 5, 34.4 g of raw material B 650 was pyrolyzed at 45 ° C under vacuum at bottom distillation fraction # 6 (Table 3, Fig. 18) for 17.3 hours. The eluate of column chromatography (step · step 6) was analyzed by GC / MS, and the residence time of hexamantane was measured. Individual hexaadamantane components with a molecular weight of 396 are numbered according to the order in which they fall off in this G C / M S analysis. These six diamonds are the most popular and convenient choice. Similar analyses can be used for other molecular weights. GC / MS analysis of No. 6 Diamond Kong Yuan; Gu Li time was 17.8 8 minutes (Six King Kong # 1) and 19.5 1 minute (Six King Kong Hang # 7). The dwell time varies with the GC column and the time required to remeasure the dwell time. Figure 13A lists the results of another gc / MS analysis of the ingredients of Six King Kong. Use _ column preparation for siphon gas chromatography to remove __ '52-

This paper size applies to Chinese National Standard (CNS) A4 specifications (210 X 1244477 A7 B7) 5. Description of the invention (SO) Steamed fractions are separated by six diamonds. For the first-preparation worm-suction GC column (methyl stone eve)嗣 DB-i equivalent), set the fractionation time of hexamantane using the dwell time pole pattern of GC / MS analysis. The results are shown in Figure 42 and confirmed as two of the hexamantane-containing fractions. And send it to column 2 &quot; ~~, using the first column 'to condense the hexamantanes from the fractions taken out and then sent to the second column (see description of hexamantanes # 2 and # 8 of Figure 〇). The second column (phenyl-methyl lithoxone, DB-II equivalent) was further purified from other substances, and then used to isolate the target _, leaving it at independent t Carrying benefits (carriers 1-6). Collect GC carrier fractions and proceed to a separation process that does not target hexamantane # 2. Collect gC carrier fraction 3 and further process for separation of hexamantane # 8 Subsequent GOMS analysis of the material of carrier # 1 (Figure 43) shows that it is mainly based on the earlier operation of gc / ms * analysis ~ /, to just: k # 2. Similarly, the carrier Analysis of the substance # 3 (Figure 44) shows that it is the main six-adamantane # 8. This procedure can be repeated to isolate the other six-adamantane. The highly concentrated hexa-adamantane can be added directly to the carrier or added from the solution. Crystallize the foot. Under a 30x magnification microscope, the crystals can be seen in the preparation of gC carrier fraction 1 (see Figure 45). These crystals are preferably transparent and show a high refractive index. The crystal of alkane # 2 does not exist. When the concentration is not high enough to crystallize, it needs to be further concentrated by GC for preparation. Figure 46 is a photo of hexamantane # 8 crystallized in preparation gc: carrier 3. Single There is no crystal containing hexamantane # 8 before leaving. After obtaining a crystal of an appropriate size, the structure of the non-stereostructured substance &lt; hexamantane can be determined using ray winding. Stereoisomerized metal adamantane can be entered- 53-1244477 A7 _ B7 V. Description of the invention (51) One step separation and separation of two components. Example 7B: Single HPLC system using single HPLC system. Two HPLC columns with 50 cm x 20 mm ID5. Whatman 18 gauge Cornerstone Xishuang (ODS) tubing (Whatman tubing is (Manufactured by Whatman Inc.) in series operation. 500 ml of Fraction 6 pyrolysis product solution sample was taken with a hydrocarbon fraction (54 mg), and the product of Example 1, Step 6 was injected into the column. 5.0 ml / A minute of acetone was used as the mobile phase to start the column. Part of the HPLC fraction reached the purity required for crystallization of hexamantane alone, such as ODS HPLC fraction # 39, hexamantane # 8 (Figure 47). ODS HPLC fraction Hexamantane # 10 in # 48 (Fig. 48) and Hexamantane # 6 in ODS HPLC Fraction # 63 (Fig. 49) are shown. Alternatively, Hypercarb columns (manufactured by Thermo Hypersil, Penn, USA) or other applicable columns can be used to purify hexamantane to the concentration required for crystallization. Preparation of the pyrolysis product of the hydrocarbon-saturated starting material B distillate fraction 6 was performed using Hypercarb HPLC, and HPLC chromatography was recorded using a differential phase refractometer. Fractions were removed during the operation (for example, Figure 50) and showed that most of the hexamantane exhibited different dissolution times from each other on the Hypercarb HPLC system (as evidenced by GC / MS analysis) (Figure 20). Example 7C: Isolation of hexamantane using multiple HPLC columns with different selectivity Figure 51 demonstrates that performing a Hypercarb HPLC fraction to obtain high purity hexamantane # 13. Other ODS HPLC fractions and Hypercarb HPLC fractionation points can be used to isolate the remaining six diamonds. 〇DS and Hypercarb columns can also be used in reverse. Figure 52 shows GC / MS total ion chromatography (TIO) of a Hypercarb HPLC column containing hexamantane # 7. The lower half of FIG. 52 illustrates the mass spectrum of the GC / MS peak 'to demonstrate the high purity of hexamantane # 7. -54- This paper size is in accordance with China National Standard (CNS) A4 (210X 297mm) ^ 1 1244477 Α7 ----- 一 Β7 5. Invention Description (52) ~ ^-It can be separated in the same way with other Various remaining 0 DS HPLC hexaamantane residues (Figure 19). By using a similar method as described above, that is, using Hypercarb or other applicable columns, and collecting at the corresponding dissolution time (fractionation of hexaamantane containing The 〇DS fraction separates the remaining hexamantane with high purity. This is also applicable to hexamantane with molecular weight 382 ("irregular, hexamantane). Its amount in this raw material is far lower than the molecular weight of 396 Figures 53 and 54 show goodbye ion chromatography at m / z 382, showing hexamantane operating at 18.30 and 18.07 minutes, respectively. Figures 53 and 54 also show the phases of these 18.30 minutes and 18.07 minutes peaks Corresponding to mass spectrometry, it is proved to contain pyrolysis process from raw material B steaming house fraction # 6 The 382 molecular weight hexamantane in the saturated hydrocarbon fraction of the product. The 382 molecular weight hexamantane shows internal bond tension, which is lower in stability than the 396 molecular weight hexamantane, and the corresponding low concentration, which results in a worse 382 molecular weight of hexamantane. Hexamantane. Stereoisomers Hexamantane was not separated in the GC / MS analysis, and therefore these carcass isomer pairs are represented by a single number. These stereoisomers can be separated by a palm separation method Example 7D: Substituted raw materials A and B of substituted hexamantane also contain substituted hexamantanes containing tiger-based hexamantine. These substituted hexamantanes are used in the same way as unsubstituted hexamantanes. And can be used as an intermediate in various hexamantane applications (such as polymer products) 'and can be de-sintered to produce relatively underivatized hexamantane hydrazone. Therefore,' design the method of replacing hexamantane with a single Examples of alkyl substituted hexamantane. Substituted hexamantane (including alkyl hexamantane) can be separated by HPLC with appropriate distillation fractions and isolated with high purity, as shown in Figure 55 -55- This paper is applicable to the standard in National Standard (CNS) A4 specification (210 X 297 mm) 1244477 A7 B7 V. Description of the invention (53). Figure 55 shows the fraction # 55 separated by SDS HPLC from the saturated hydrocarbon fraction of raw material B, containing The high-purity methylated hexamantane lipid distillation fraction 6 is pyrolyzed. The monomethylated hexamantane has a molecular weight alkane 4 10 (the resulting molecular ion is m / z 4 10 and the mass loss of the methyl group is obtained. m / z 3 95 partial ions (Figure 55B)). Separating the substituted hexamantane component by HPLC requires multiple columns with different selectivity. For example, ODS and Hypercarb HPLC columns are operated continuously to isolate the methylcyclohexamantane component (the methyl-substituted mole weight of 342 hexamantane) from the steam product saturated with hydrocarbons. From this first SDS HPLC operation, fractions # 23-26 were combined and further purified in a second HPLC system. The combined fractions contain a mixture of hexamantane (Molar weight 342 refers to cyclohexamantane), three methyl cyclohexamantane (12.31 minutes dissolution on the GC / MS system and dissolution at 12.56, 12.72 and 13.03 minutes ( # 1-3). Further purification of this mixture (i.e., combined ODS HPLC fractions # 23-26) was achieved using a Hypercarb static phase HPLC column. A 50 ml sample of acetone containing approximately 1 mg of the combined fractions was injected into a Hypercarb column (10 mm ID X 25 0 mm), using 3.00 ml / min of acetone as a mobile phase, and operated using a differential phase refraction detector ( @ 480 psi). In this Hypercarb system, methylcyclohexamantane # 1 is first dissolved in fractions 18-22, and methylcycloadamantane # 2 is dissolved in fractions 23-25. Methylcycloadamantane # 1 and # 2 were isolated with sufficient purity to form crystals. The GC / MS total ion chromatograms and mass spectra of these compounds are illustrated in Figures 57 and 59 and illustrated by the crystals of the photographs in Figures 59 and 60. Figure 9 illustrates methylcyclohexamantane crystals precipitated from Hypercarb HPLC fraction # 19-21, and Figure 60 illustrates methylcyclohexamantane crystals precipitated from Hypercarb HPLC fraction # 23. -56- This paper size applies to China National Standard (CNS) A4 (210 X 297 mm) 1244477

The stereoisomer pairs need to be further divided and separated to get the two components. After obtaining crystals of an appropriate size, you can choose μ ... shot, 'spring crystal chart to determine the structure of non-stereoisomeric alkyl hexadiamond. Male 'Example 8 A · Isolation of heptammeine compound by GC / MS analysis of the eluate of column chromatography (step 6, Fig. 12) to determine heptammein (GC residence time. &Gt; + amounts 394 and 448 The individual heptamole components are numbered according to their dissociation order in the GC / MS analysis (see Figure &quot; A 4 representative analysis value). The molecular weight 448 heptamantane (with the most heptamole value) is in this example. Easy to use. Similar analysis can be used to prepare other seven molecular weight institutes of other molecular weights. Then use two-column preparation for siphon gas chromatography to remove from column chromatography &lt; Separate fractions separate heptamantane. Heptamantane The fractionation time is based on the dwell time and pattern of GC / MS analysis (from step 2 above, Figure 12). It is set for the first preparation siphon GC column (methyl silicone DB-1 equivalent). List The results are listed above Fig. 61, and they are sent to column 2 &quot; with the peaks of the π peaks of the seven diamond ridges two from the raw material b. The first type of column is used to remove and then sent to the second column. The remaining concentrated heptamantane (see Figure 6 1 explaining heptamantane # 1 and # 2). Second column (phenyl group -Methylsilicone, DB-17 equivalent) Further separation and purification of heptamantane, which was then used to isolate the peak of the target and leave it in a separate carrier cry (carriers 1 -6). Collect 0 (1: Carrier House 2 and further processing for separation of heptamantane # 1. Collect GC carrier fraction 4 and further process for separation of heptamantane # 2. Subsequent GC / MS analysis (Figure 62) shows that it is mainly based on the GC / MS analysis of the earlier operation of Step 4. -57- ^ The paper size applies the Chinese National Standard (CNS) Α4 specification (210 X 297 male ~ &quot; '&quot; &quot; &quot; &quot; '~~' *-1244477 A7 B7 V. Description of the Invention (55) Heptamantane # 1. Similarly, the GC analysis of the substance # 4 (Figure 63) shows that it is heptamantane # 2. This procedure can be repeated to separate the other heptamantane components. The highly concentrated heptamantane can then be directly added to the carrier or crystallized from the solution. Under a 30x magnification microscope, it can be prepared in Crystals were seen in the GC carrier Fraction 2 (see Figure 64). These crystals are preferably transparent and show a high refractive index. Crystals of adamantane # 1 did not exist. When the concentration was not high enough to cause crystallization, it was necessary to further concentrate with preparative GC. Figure 65 is a photo of seven adamantane # 2 crystallized in the preparative GC carrier 4. Single There is no crystal containing heptamantane # 2 before leaving. After obtaining a crystal of an appropriate size, the structure of heptamantane can be determined using an X-ray crystal chart. The stereoisomeric heptamantane can be further separated and analyzed for its two components. Example 8B : Purification HPLC of a single heptamantane isomer has also been shown to provide a sufficient amount of heptamantane to crystallize. The HPLC column used was the same as the other examples (ODS and Hypercarb). A 500 ml sample of a saturated distillate solution of pyrolysis product 7 (step 6, FIG. 12) of hydrocarbons was injected into the ODS column. The pyrolysis of fraction 7 used 25.8 g and was heated at 450 ° C for 16 hours. ODS HPLC fractions reach the purity required for crystallization of heptamantane alone, as shown by heptamantane # 1 in ODS HPLC fraction # 45 (Figure 66). Others, such as heptamantane # 2 in ODS HPLC fraction # 41 (Figure 67), heptamantane # 9 in ODS HPLC fraction # 61 (Figure 68), and ODS HPLC fraction # 87 (Figure 69) All of the seven Kanaoka | Jane # 10 may need to be further separated in HPLC system with different selectivity. Progress on Hypercarb column -58- This paper size is applicable to China National Standard (CNS) A4 (210 X 297 mm)

Pretend

1244477 A7 B7 V. Description of the invention (56) ODS fractionation (Figure 13B) to obtain the purity required for crystallization of heptamantane alone, such as heptamantane ingredient # 1 and seven in Hypercarb HPLC fraction # 55 (Fig. 70) Adamantane # 2 (Figure 71). Advanced diamond samples in each HPLC fraction can be separated using other chromatography techniques including preparative gas chromatography, or other HPLC using columns of different selectivity, as listed below. In addition, other techniques in the crystallization technique can be used, including (but not limited to) branch sublimation, stepwise recrystallization, or zone purification can be used to purify heptamantane. By using a similar method as described above, that is, using Hypercarb or other applicable columns, and collecting at the corresponding dissolution time, the division of the 0DS containing heptamantane can be better or better than the single ionization of the seven adamantane. . This is for heptamantane with molecular weights of 420 and 434 (the amount in the raw material is much lower than that of heptamantane with molecular weights of 394 and 448). The heptamantane component with a molecular weight of 420 is shown in an ODS HPLC fraction # 61 (Figure 73A) with extremely strong molecular ions in a mass spectrum with m / z 420 component at 16.71 minutes (m / z 420 in this example, Figure 73B) )in. This mass spectrometry (a very low amount of prominent molecular ions and an included part) is characteristic of the stone-like composition. Example 8C: Isolation of substituted heptamantane The starting materials A and B also contained alkyl heptamantane containing substituted heptamantane. The alkyl heptamantane can be purified by removing non-diamond-like impurities from the raw materials by using pyrolysis as described above. The specific alkyl heptamantane is left in the thermal process, as previously identified for heptamantane. The alkyl heptamantane containing the substituted heptamantane component can be separated using a single HPLC and isolated in high purity, as shown in Figure 74. The molecular weight of the monomethylated heptamantane is 408 (the obtained molecular ion of the mass spectrum is m / z 408, and it shows the mass loss of the methyl group, -59- This paper size applies to the Chinese National Standard (CNS) A4 specification (210 X 297 Mm)

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1244477 A7 B7 V. Description of the invention (57) The 111/2393 mass spectrum ion showing the heptamantane site was obtained (Figure 748). Example 9A: Isolation of the octamantane component The octamantane rich in step 6 :): The finished fraction was subjected to reverse phase Plc. In some cases, the purification can be performed by reverse-phase HPLC using acetone as a mobile phase. Raw material B distillation fraction 7 pyrolysis product-saturated hydrocarbon fraction (used in Example 8A) was prepared using an ODS HPLC operation, and the HPLC analysis was recorded using a differential refractometer. The HPLC fractions were analyzed by GC / MS to determine the dissolution time of octamantane HPLC and monitor the purity (see Figure 13A of the analytical values for preparation). The HPLC column used was the same as the ODS and Hypercarb systems previously used in practice. A 500 ml sample of a hydrocarbon (25 mg) distillate acetone solution containing the pyrolysis product of saturated fraction 7 was injected into an ODS column. Although this HPLC system was used, some octamantane reached the purity required for octamantane crystallization alone. For example, Figure 75 illustrates GC / MS total ion chromatography and mass spectrometry of an HPLC fraction in which octamantane # 1 has been purified to the point where crystals are formed (see Figure 76). HPLC fraction 63 yields the combined octamantane # 3 and # 5 (Figure 77), which co-crystallizes from the fractions (Figure 78). For the high-purity ionization of other octamantane components (for example, Figures 79 and 80), Multi-column columns such as Hyper ere arb can be used. Example 9B: A mono-alkylated octamantane substituted with an octamantane component can be purified using the method described for the non-alkylated octamantane in Examples 1 and 3. Figure 81 (A / B) shows that ODS HPLC fraction 94 contains high purity methylated octamantane. The monomethylated octamantane has a molecular weight of 460 (m / z 460 mass spectrum molecular ion is obtained, and the m / z 445 mass fraction ion of the octamantane portion of the methyl mass read loss is shown (Fig. 81B). Moreover, when ODS or -60- This paper size applies to China National Standard (CNS) A4 (210 X 297 mm) 1244477 A7 B7 V. Description of the invention (58)

When the Hypercarb HPLC fraction contains more than one alkyl octamantane, additional HPLC separation or preparation of the fraction using a GC procedure (as in Example 3) can result in high purity octamantan. Example 10A: Isolation of the nonadamantane component. Raw material B. Distillation fraction 7. Preparation of saturated hydrocarbon fractions of pyrolysis products. SDS HPLC operation (substance described in Example 8A). To determine the dissolution time of nonamantane HPLC (Figure 82) and monitor purity. A 500 ml sample of a hydrocarbon (25 mg) portion of acetone solution containing saturated pyrolysis product 7 was injected into the column. The column was started using 5.00 ml / min of acetone as a mobile phase carrier. For high-purity monomeric adamantane components, multi-column HPLC columns can be used. To illustrate this method, HPLC columns with different selectivities of ODS and Hypercarb (as described in the previous example) were used continuously to isolate a single nonamantane. From the operation of ODS HPLC, the diamantane-containing fractions 84-88 (Fig. 13B) were combined and further purified in a Hypercarb HPLC column system. · Inject 50 microliters of a dichloromethane sample containing 1 mg of ODS HPLC combined fractions (84-88) into a two Hypercarb column (two 4.6 mm IDX 200 mm), using 1.30 ml / min of dichloromethane as a mobile Phase continuous operation. Figure 83 shows GC / MS Total Ion Chromatography (TIC) of Hypercarb HPLC fractions containing concentrated Nine Diamonds. The lower half of Figure 83 illustrates the mass spectrum of the GC / MS peak. Jiujingang uses the same Hypercarb static phase column, and its solvent contains dichloromethane / acetone (70:30 vol%, operating at 1.00 ml / min), and is isolated by a third HPLC operation. The obtained mono-nine adamantane crystal and -61- This paper size is applicable to Chinese national standards (CNS &gt; A4 size (210 X 297 mm)

Pretend

1244477 A7 B7 5. Explanation of the invention (59) The relative mass spectrum is not shown in Fig. 84. By using a method similar to the above, that is, using a column with a different selectivity (such as Hypercarb or other applicable columns) to separate the ODS HPLC fraction containing nine diamonds, with a high purity of 498 Nine adamantane. This method can be repeated to isolate the nonamantane with a molecular weight of 552 and the nonamantane with a molecular weight of 538, 484, and 444, which are low in the raw materials. It is necessary to understand that the stereoisomers of nonamantane are not resolved in GC / MS, however, these stereoisomers can be isolated in a single palm separation method. Example 10B .. Single Isolation of Substituted Amantadine Raw materials A and B also contained substituted nonamantane. Alkyl nonamantane can be purified using methods described for non-alkylated nonamantane. Figure 85 (A / B) shows methylated nonamantane in the pyrolysis product of distillation fraction # 7. The molecular weight of one type of monomethylamtamantane is 512 (obtain a mass molecular ion of m / z 512 and show the mass loss of the methyl group to obtain the m / z 497 mass ion showing the nonamantane position) (Figure 85B) ). There are more than one type of alkyl pentamycin, and these can be isolated using ODS or Hyper arb column. Additional HPLC separation or GC isolation for preparation can be used to obtain high-purity alkyl pentamide. Example 11A: Desolation of decamantane component. Distillation of raw material B. Preparation of saturated hydrocarbon fraction of pyrolysis product. DS HPLC operation was performed and HPLC fraction was analyzed by GC / MS to determine decamantane HPLC. Dissolution time (Figure 86) and purity monitoring. The HPLC column used was two 50 cm X 20 mm I.D. Whatman octadecylsilane (ODS) tubes operated in series. 500 ml of saturated hydrocarbons containing pyrolysis products of fraction 7

A sample of the fraction (25 mg) of the acetone solution was injected into the column. The column was started using 5.00 ml / min of acetone as a mobile phase carrier. For high-purity monodecamantane, multi-column HpLC can be used. In order to illustrate the method, HPLc tubes with different selectivities are used continuously to separate a single decamantane. The HPLC system contains the same ODs column as previously described. From the operation of this HPLC, the decamantane-containing full fractions 74-83 can be combined and further purified in a second HPLC column system. The remote operation was repeated five times' and the ten adamantane-containing fractions of all operations were combined. The combined fractions contained decamantane with a molecular weight of 456 and various impurities. To purify the combined HPLC fractions 74-83 from ODS HPLC separation, 50 microliters of gold containing approximately 1 耄 g of ODS HPLC combined fractions of acetone / dichloromethane (70: 30% by volume) was injected using 1.00 ml / Min. Acetone / dichloromethane (70: 30% by volume) was used as the mobile phase (@ 480 psi) in a Hypercarb column (4,6 mm ID X 200 mm). Figure 87 shows GC / MS total ion chromatography (TIC) of a concentrated decamantane-containing Hypercarb HPLC library that dissolves for another 18.55 minutes. The lower half of Figure 87 illustrates a GC / MS mass spectrum with a prominent peak at m / z 456. The crystals and mass spectra of the obtained [123 124 1 (2) 3] molecule in 4 5 6 ten diamond pits are shown in Figs. 4 5 6 10 Ammonia® dissolves in the Hypercarb HPLC system earlier than Hardane # 3 because of its smaller, extremely low surface area structure (Figure 10). This property of 456-molecular weight ten diamonds allows it to be isolated with extremely high purity. By using a similar method as described above, that is, using a column with a different selectivity (such as Hypercarb or other applicable columns) to separate the fraction containing ΗDS Η PLC i from Shijingangyuan with a high molecular weight of 4 5 6 ten ten King Kong, j: charge. The -63- This paper size applies to China National Standard (CNS) A4 (210 X 297 mm)

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1244477 A7 ^ ----- -B7_ V. Invention 61) &quot; --- Wanfa can repeat with a molecular weight of 496 (the saturated fraction of the pyrolysis product of distillation fraction # 7 is shown in Figure 89) And decamantane with a molecular weight of 55 or 60, and decamantane with a molecular weight of 536, 576, and 590, which are low content in this raw material, respectively. It is to be understood that the stereoisomer decamantane is not resolved in Gc / Ms', however, these decamantane can be isolated in a single palm separation method. Example 11B: Single ion of substituted ten adamantane. Raw materials A and B also contain substituted adamantane. Alkyl decamantane can be purified using methods described for non-alkylated decamantane. Figure 90 shows methylated decamantane in the saturated fraction of the pyrolysis product of distillation fraction # 7. One type of monomethylated decamantane has a molecular weight of 47 ° (mass molecular ions of m / z 47 ° are obtained). Furthermore, when ODS or Hypercarb-containing HPLC fractions contain more than one decyladamantane, these fractions can be separated by additional PlIX separation or different GC procedures can be used to obtain high purity alkyl decamantane. Example 12: Isolation of eleven adamantane ingredients To separate elundadamantane ingredients with high purity, a multi-hplc column can be used. This method was used when adamantane was used continuously with HPLC columns of different selectivity, as demonstrated by a single decamantane (example u). Applicable starting materials (raw material B, distillation fraction 7 pyrolysis product) have been shown to contain elundamidine (Figure 9 1). Concentrated undecamantane (Figure 13B) from the ODDS HPLC fraction 100+ is shown in Figure 92. This fraction can be purified on Hypercarb HPLC using the system (same as described in Example i i). This method can be repeated with eleven adamantines having an molecular weight of 656 and / or 602, and a molecular weight of 642, 628, 5 88, 548, or 5 3 4 (which are as expected in this raw material, respectively). I -64- This paper size applies to China National Standard (CNS) A4 (210 X 297 mm)

Claims (1)

4 物 复 i — 7 ¥ of Lion 110 Patent Application A _7.4, Patent Application Scope Farming 3 Select moxibustion 鬲 -grade diamond-like ingredients, it is not eight, 2. Anti-four Jingang m, also does not contain rich Ring Six King Kong ;, s rich in unsubstituted; high-grade diamond-like components present at least 25 wt% &lt; V where 蔹 is rich in the choice of one kind of rich-one or more choices of high-grade diamond into :. Medium-species or multiple choices of high-grade turnstone-like ingredients: two :: thing 'its 1 w t❶', the condition is that when there is only-one choice of at least the composition, it is not an unsubstituted anti-four King Kong :::: Stone-like ingredients Six King Kong. Not an unsubstituted ring 3. The high-grade diamond-like composition of the composition as claimed in the scope of the patent application, including the composition;-one or more options 4. The composition as the scope of the patent application, the second category ... ::%. Or a selection of premium diamond-like ingredients. … / A kind containing 70 to 100 wt%, a kind containing 95 to 100 wt%, a kind containing 99 to 1000 wt%, 5. A composition such as the scope of the patent application item 2, or a variety of advanced options Diamond-like composition. 6. The composition as claimed in item 2 of the patent application or a variety of advanced diamond-like ingredients. 7. The composition of item 2 of the scope of patent application or a selection of advanced diamond-like ingredients. 8. The composition of any of the "items", in which one or more of the selected high eight YK knives are single-selected high-grade diamond samples = including one or more selected high-grade shells relative to the total number of diamond samples. K-shaped knife-like diamond-like composition, in which at least 25 of the total number of diamond-like diamonds is one or more selected types of high-grade diamond-like diamonds, the condition is that when only> X 297 mm) 1244477 When choosing a kind of high-grade diamond-like composition, it is also not a ring six diamond. It is the unsubstantiated reverse. The composition of item 9 in the patent scope of the eye, in A-: The selected high-level squatting stone-like composition is in a single-like stone:-one or more kinds of economic scores. Many of the diamond-like families are U. For example, please apply for the composition in item 9 of the patent scope, where-: 睪: grade diamond-like ingredients are single selection: :: or multiple outlines. 9 to "item of any stone": ingredients. Among them, selected advanced diamond-like ingredients J &lt; composition, ingredients. Estimate one or more types of tetra-ammonium entertainment One or more types of tetra-ammonium, of which the single-tetra-ammonium flammable component is the middle-mono-tetra-adamantane component 13. The composition such as the scope of application for item 12 of the door 1J k component is a single-tetra-adamantane component. 14. If the composition of claim 13 is iso-tetramantane. 15. The composition according to item 13 of the patent application is helical-tetramantane. Medium monotetramantanane composition Medium tetratemantine composition package 16. The composition of item 13 in the scope of the patent, which is a single stereoisomer of helical-tetramantane. 17. A composition as claimed in claim No. 2 and including a substituted tetramantane component. A rich iso-tetramantane that exhibits a purity of at least 25% by weight. The helical-tetramantane stereoisomer a contained in 19 ′ species was found to have a purity of 25 w t%. J 20 · —The helical-tetramantane stereoisomer B contained in the species, which appears to ... -2- Wood paper size is applicable to China National Standard (CNS) A4 specifications (210X297 mm) A8 B8 C8 1244477 Six, The patent application range is 25 wt% purity. 21. If the tetramantane rich in any of Patent Application No. 18-2 "is crystalline. 22. If the combination of any one of Patent Application Nos. 丄 to 7 and 9 to 丨 丨The diamond-like components selected by the Chinese court include one or more metal adamantane components. 23. For example, in the composition of claim 22, one or more metal adamantane components are mono-metal adamantane. 24. If the composition of claim 22 of the patent claim, one or more of the components of the freshly burned metal are isolated optical isomers. 25. If the composition of claim 22 of the patent claim, one or A variety of hardware steels and components are heterogeneous hardware burned components. 26. For example, the composition claimed in item 22 of the patent scope, where one or more hardware steels: ^ The composition is a non-isomeric five represented by the formula (^ 出 ⑼ Amantadine component. 27 · —A kind of metal adamantane component contained in §, which has a purity of at least 25 wt%. 28. If the metal adamantane component rich in the 27th item of the patent application scope, it is crystalline. 29 · If the patent application scope 27 is rich in hardware adamane, of which hardware The alkane component is [1 23 1] hardware adamantane. 30. For example, the 27th aspect of the scope of patent application is rich in hardware adamantane component, wherein the metal just burned component is [1 2 13] stereoisomer A hardware adamantane. 31 · If the 27th item in the scope of patent application is rich in metal adamantane, and the first metal component is [12 1 3] isomer B hardware Dangxuan *. 32. If the 27th scope of patent application is rich in Components of metal adamantane, of which hardware-3- This paper size is applicable to Chinese National Standard (CNS) A4 specification (210 X 297 mm) 1244477 as B8 C8 _ D8 VI. Patent application Fanyuan amantane composition is [1234] three-dimensional Structure A. Hardware adamane. 33. For example, the scope of patent application No. 27 is rich in hardware adamane, where the hardware adamane component is [1234] stereoisomer B hardware adamantane. 34. If the scope of patent application is 27 The item rich in metal adamantane, of which the metal adamantane is [12 (1) 3] stereoisomer A metal adamantane. 35. For example, if the item 27 of the scope of patent application is rich in metal adamantane, five of them The adamantane component is [12 (1) 3] stereoisomer B metal adamantane. 36. For example, the 27th item in the patent application Components of metal rigid pits, of which metal rigids are [1212] metal rigids. 37. For example, the scope of patent application for item 27 is rich in metal rigids, among which metal rigids is [1 (2,3) 4] Hardware adamane. 38. If the 27th item of the scope of patent application is rich in metal adamantane component, of which the metal agglutination component is [12 (3) 4] hardware agglutination. 39. if the patent application is rich in item 27 Hardware adamantane component, wherein the hardware adamantane component is an unsubstituted hardware adamantane component. 40. If the patent application scope item 27 is rich in metal adamantane, the metal adamantane component is a substituted metal adamantane component. 41. The composition as claimed in any one of claims 1 to 7 and 9 to 11 in the patent application range, wherein the selected higher diamond-like ingredients include one or more hexamantane components. 42. The composition according to item 41 of the scope of patent application, wherein one or more of the six diamonds are single-six diamonds. 43. The composition according to item 41 of the application, wherein one or more of the hexamantane components are isolated optical isomers. -4- The paper size is suitable for financial standards (CNS) A4 specification (2igx mm j 1244477 as B8 C8 D8 VI. Patent application scope 44. For example, the composition of patent application scope item 41, one or more of which The diamond-like composition is a heterogeneous six-kingdom-fired ingredient. 45. For example, in the composition of claim 41 in the scope of patent application, one or more of the six-kingdom-fired ingredient is one or more six-kingdom-fired ingredient represented by the formula C3GH36. 46. For example, the composition in the scope of application for item 41, wherein one or more hexamantine: fe component is one or more hexamantine ingredients represented by the formula C 2 9 Η 3 4. 47.-hexamantane-rich component It is represented by substituted or unsubstituted formulas C30H364 C29H34, and it exhibits a purity of at least 25 wt%. 48. If the hexaamantane-rich component in item 47 of the patent application scope is rich, it is crystalline. 49. If the hexamantane-rich component in item 47 of the patent application scope is represented by formula C29H36. 50. If the hexamantane-rich component in item 47 of the patent application scope is represented by formula C30H36. 51 · If the scope of patent application is 50th It is rich in hexamantane, which is selected from the group: [1 (2) 3 14] stereoisomer A hexadamantane [1 (2) 3 14] stereoisomer B hexadamantane [ 12 (1) 32] stereoisomer A hexamantane [12 (1) 32] stereoisomer B hexamantane [12 (1) 34] stereoisomer A hexamantane [12 (1) 34 ] Stereoisomer B Hexamantane The paper size is applicable to Chinese National Standards (CNS) A4 specifications (210 X 297 mm 1244477 as B8 C8 D8 6. Application scope [12 (1,3) 4] Hexamantane [ 12 (3) 14] stereoisomer A hexaadamantane [12 (3) 14] stereoisomer B hexaadamantane [121 (2) 3] stereoisomer A hexaadamantane [12 1 (2) 3] Stereoisomer B Hexamantane [12 123] Stereoisomer A Hexamantane [12 123] Stereoisomer B Hexamantane [121 31] Stereoisomer A Hexamantane [12131] Stereo Isomer B Hexadamantane [121 34] Stereoisomer A Hexamantane [12134] Stereoisomer B Hexamantane [12324] Stereoisomer A Hexamantane [12324] Stereoisomer B Hexamantane [12341] Stereoisomer A Hexamantane [12341] Stereoisomer B Hexamantane [1 (2) 3 (1) 2] Hexamantane [12 (3) 12] Hexade [121 (3) 4] hexamantane [12 12 1] hexamantane [12321] hexamantane [1 (2) 3 (1) 4] stereoisomer A hexamantane [1 (2) 3 (1) 4] Stereoisomer B Hexamantane 52. For example, the hexaamantane-rich component in Item 47 of the scope of application for patents, in which the hexa-amantadine component is an unsubstituted hexa-amantadine component. -6- This paper size applies to China National Standard (CNS) A4 (210 X 297 mm) A8 B8 C8 1244477 53. If the patent application No. 47 of the patented garden is rich in six-gold. Oka &quot; "Parts are substituted hexaamantane components. 'Of which six-gold 54. Farming D's substituted cyclic hexa-amantanes, which presents A purity of at least 25 wt%. 55. The composition of any one of claims 1 to 7 and 9 to 11 in the patent application scope, wherein the selected higher diamond-like component includes one or more heptamantane components. 56 · For example, if the composition in the scope of patent application No. 55, one or more of the heptamantane component is a mono-heptamantane component. 57. In the composition in the scope of patent application No. 55, one or more of the heptamantane component is Single-isolated optical isomers. 58. For example, in the composition of the patent application No. 55, one or more of the heptamantane components are isomeric heptamantane components. 59. Such as the patent application No. 5 5 The composition according to item 1, wherein one or more heptamantane components are one or more isomeric heptamantane components represented by formula C3GH34. 60. The composition according to item 55 of the patent application scope, wherein one or more The composition of Vajrayana is C32h3 One or more isomers of heptamantane represented by 6 61. The composition of item y of Shenyang Patent Fanyuan, wherein one or more of the heptamantane ingredients is one or more isomers represented by the formula C3 3 H38 Heptamantane component 62. For example, in the composition of the Shenyang Patent Fanyuan Item μ, one or more of the heptamantane component is one or more heterogeneous seven adamantane papers expressed by the formula C34H4G Fresh (CNS) A4 specification (㈣χ 297 public envy) 1244477 Yi C8 D8 Six, apply for patent scope burned ingredients. 63.-Seven I Kongangyuan ingredients contained in 'I' presents a purity of at least 25 wt%. 64. If applied The painting in item 63 of the patent scope contains the heptammonite component, which is in a crystalline state. 65. For example, the application in the scope of the patent item 63 contains a heptammonite component, in which the molecular weight of the heptamantane component is 394. 66. If applying for a patent The heptamantane-rich component of the 63rd item, of which the heptamantane component is [12 1 32 1] heptamantane. 67. For example, the heptamantane-rich component of the 63th item of the patent application scope, wherein the heptamantane component [123 124] Heptamantane. 68. If the heptamantane-rich component of item 63 in the scope of the patent application is applied, of which the heptamate dry component is the unsubstituted heptamantane component. 69. If the heptamantane-rich component of item 63 of the patent application scope, of which The heptammonite component is a substituted heptamantane component. 70. The composition of any one of claims 1 to 7 and 9 to 11 in which the selected advanced diamond-like component includes one or more octamantine Hexane ingredient. 71. The composition according to item 70 of the patent application scope, wherein one or more of the octamantine components are mono-octamantine components. 72. A composition as claimed in claim 70, wherein one or more octamantane components are isolated optical isomers. 73. The composition of claim 70, wherein one or more octamantane components are isomeric octamantane components. 74. As claimed in the patent, the composition of the accumulation of which, one or more kinds of eight gold 1244477 A8 B8 C8 D8, one or more kinds of eight gold or more isomers One of the one or more eight gold species or more isomers of one of the eight golds' one or more eight gold species or more isomers of one or more eight golds is one of the ingredients represented by the formula C: 33H36. 75. If the composition in the scope of patent application No. 70 is just burned, it is one of the formula C; 34H38. 76. The composition according to item 70 of the scope of application for patent: The ingredient is one of the ingredients expressed by the formula c36h4q. 77. The composition according to the scope of patent application No. 70. The freshly burned component is one of the components expressed by the formula C37H42. One or more eight gold species isomerized eight diamonds 78. The composition according to item 70 of the patent application scope, wherein the freshly burned component is one or more slave components represented by the formula C38H ". ^ ^ ^ &Lt; 乂 2 5 wt% purity. Muscle; wide patent range 79 rich in adamantine ingredients, which is crystal 81 ·: Π: 利 范围 79 The item is rich in octamantine, of which octamantine J and 6% are unsubstituted octamantane. 82. For example, the octamantane-rich component in item 79 of the patent application scope, of which octamantine fe is Substituted octamantane component 83. The composition according to any one of claims 1 to 7 and 9 to 11 of the scope of patent application, wherein the selected high-grade diamond-like component includes one or more nonamantane components 0 84 · For example, for the composition in the scope of patent application No. 83, one or more of nine gold-9 X2Q7 mm) A B c I 1244477 6. Scope of patent application The calcined ingredients are single adamantane ingredients. 85. The composition of claim 83, wherein one or more of the nine-fired diamond components are isolated optical isomers. 86. The composition of claim 83 in the scope of patent application, in which one or more of the nine diamond k components are isomeric nine diamond burner components. 87. The composition of claim 83 in the scope of patent application, wherein one or more of the nonadamantane components are isomeric nonamantane components represented by the formula C ^ H36. 88. The composition according to item 83 of the patent application, wherein one or more of the nonamantane component is one or more isomerized nonamantane components expressed by the formula. 89. The composition as claimed in claim 83, wherein the one or more nonamantane components are one or more isomerized nine adamantane components represented by the formula CwH42. 90_ The composition according to item 83 of the patent application scope, wherein the one or more nine diamond components are one or more isomeric nine diamond components expressed by the formula C40H44. 91. The composition according to item 83 of the patent application scope, wherein one or more of the nonadamantane: fe component is one or more isomeric adamantane components represented by the formula C ^ H46. 92. If the composition of the scope of application for item 83 is used, one or more of the nine diamond content is one or more isomerized nine diamond content expressed by the formula C ^ H4 8. 93. A nonamantane-rich ingredient with a purity of at least 25% by weight. 94- If it is rich in nonamantane in the scope of the patent application No. 93, it is crystalline. -10- This paper size is in accordance with Chinese National Standard (CNS) A4 specification (210 X 297 mm) 1244477 A8 B8 C8 ______ —_ D8 VI. Application scope of patent 95. For example, the scope of application for patent scope 93 is rich in nonamantane Ingredients, of which Nine King Kong, the ingredients are unreplaced Nine King Kong. … 96. For example, in the 93rd patent application, it is rich in nonamantane, in which the nine adamantane component is a substituted nonamantane component. ', 97. The composition according to any one of items} to 7 and 9 to 11 in the scope of patent application, wherein the selected high-grade diamond-like component includes one or more decamantane components. 98. The composition according to item 97 of the application, wherein one or more of the decamanthin components are a single decamantane component. 99. The composition according to claim 97, wherein one or more of the decamantine components are isolated optical isomers. The composition of the scope of application of the patent No. 97, wherein one or more of the decamantane component is isomeric decamantane component. 101. The composition according to item 97 of the application, wherein one or more of the decamantane components are non-isomeric decamantane components represented by the formula C ^ H36. 102. If the composition of the scope of application for the patent No. 97, the m &amp; k: k component is one or more isomeric decamantane components represented by formula (i). 103. The composition according to item 97 of the application, wherein the κ μ + &amp; adamantane component is one or more isomeric decamantane components represented by the formula D 44. 104. For example, if the composition of the scope of patent application No. 97, one or more decamidine J ^ into wounds is one or more isomeric decamantane components represented by the formula C42H ". 105. If the scope of the patent application is 97 Meridian compounds of the item, in which one or more ten gold-11-! 244477 A8 B8 C8 r- ___ D8 _______ Six, the patent application Fanyuan adamantane component is one or more isomeric decamantane expressed by the formula c44H48 106. For example, the composition in the scope of patent application No. 97, wherein one or more of the decamantane component is one or more isomeric decamantane components represented by the formula C45H5G. 107. In the scope of patent application No. 97, A composition in which one or more decamantane components are one or more isomeric decamantane components represented by the formula C46H5 2. 108.-A decamanthin component contained in a kind of radon, which exhibits a purity of at least 25 wt% 109. If the tenth diamond-rich component in item 1 (1) of the patent application scope is crystalline. 110. The ten diamond-pit-rich component in item i of the patent application scope, where the decamantane component is [123 1241 (2 3) Ten King Kong 111. For example, in the application for the scope of patent No. 108, the ten-amantanes-rich component, in which the decamantane component is an unsubstituted decamantane component. 112. For example, the patent application scope No. 108 is rich in ten components. The adamantane component, of which the decamantine component is the substituted decamantane component. 113. The composition according to any one of claims 1 to 7 and 9 to 11 in the patent application scope, wherein the selected high-grade diamond-like components include One or more eleven amantadine ingredients. U4. A composition as claimed in item n3 of the scope of patent application, wherein one or more elundamantane ingredients are a single undecamantane component. 115. As in item 113 of the scope of patent application A composition in which one or more eleven rambutan components are isolated optical isomers. 116. The composition according to item 113 of the patent application range, wherein one or more ten-12- 8 8 8 8 AB c D 1244477 6. Scope of patent application: The one-and-one adamantine composition is isomeric and one-and-a-one adamantine composition. 117. For example, the composition of item 113 of the application scope, wherein one or more of the undanadamantane component is represented by formula C39H4 ( Heterogeneous ten The adamantane component. 118. The composition according to item 113 of the patent application scope, in which one or more undecamantane components are one or more isomeric decamanthin components represented by the formula C41H42. 119. If the scope of patent application The composition according to item 113, wherein the one or more undecamantane components are one or more non-isomeric amaranthine components represented by the formula C42H44. 120. For example, the composition of claim 11 in the scope of patent application, wherein one or more eleven adamantane components are one or more non-isomeric osmium fragrant ingredients represented by formula C45H48. 121. For example, the composition of item 113 of the scope of application for patent, wherein one or more of the eleven diamond-fired ingredients are one or more non-isomeric osmium-^-diamond-fired ingredients represented by the formula C46H5Q. 122. For example, in the composition of claim 113, one or more of the eleven emery ingredients are one or more non-isomeric eleven emery ingredients represented by the formula C48H52. 123. For example, the composition of claim 113 in the scope of patent application, wherein the one or more eleven adamantane components are one or more non-isomeric Η aramid components represented by the formula C49H54. 124. If the composition of the scope of application for patent No. 113, wherein one or more eleven adamantane components is one or more non-isomeric eleven adamantane, j: finished part represented by formula C5QH56. -13- The size of wood paper is applicable to Chinese National Standard (CNS) A4- € (210X 297 mm) 1244477 as B8 C8 D8 6. Application scope of patent 125. — 11 kinds of eleven adamantane rich in ingredients, which present at least 2 5 wt% purity. 126. If the eleven adamantane-rich component in the scope of the application for a patent is 125, it is crystalline. 127. If the scope of application for patent No. 125 is rich in undecamantane, of which the depotent of the eleven diamonds is the undeprecated constituent of the eleven diamonds. 128. For example, the eleven amantadine-rich ingredients in the 125th scope of the application for patents, of which Η the diamond-fired ingredients are substituted eleven-adamantines. 129. A method for recovering a composition rich in high-grade diamond-like ingredients, the method comprising: a. Selecting a raw material including a recoverable amount of high-grade diamond-like ingredients; b. Under conditions that have a boiling point lower than the target high-grade diamond-like ingredients The lowest boiling point raw material is removed from a sufficient amount of the component to obtain a processed raw material, and the advanced diamond-like component is recovered from the raw material; and c. Selected from the group consisting of chromatography technology, thermal diffusion technology, zone refining, progressive recrystallization and size Separation technology Separation technology recovers advanced diamond-like components from the processed raw materials. 130. A method for recovering high-grade diamond-like samples as described in the first scope of the patent application, including: a. Selecting components that include recoverable quantities of high-grade diamond-like components or recycled, non-high-grade diamond-like components, and boiling points lower than those selected Recovered raw materials with the lowest boiling point of high-grade diamond-like materials; b. Under the conditions, remove a sufficient amount of components with a boiling point lower than the lowest boiling point of the high-grade diamond-like components that are selected for recovery, among which a recoverable amount of high-grade diamond-like components or choose to recover Composition of sulfur and processed raw materials-14- This paper size applies to Chinese National Standards (CNS :) A4 specifications (210 X 297 mm) A BCD 1244477 6. In the scope of patent application; and C. Heat treatment recovered in b) above For raw materials, at least a sufficient amount of non-diamond-like ingredients are pyrolyzed, and selected high-grade diamond-like ingredients or ingredients are recovered from raw materials treated by pyrolysis. The pyrolysis is performed under conditions to obtain a recoverable amount. Selected high-grade diamond-like ingredients or processed raw materials of the ingredients; d. Selected from the group consisting of chromatography techniques, thermal diffusion techniques, zone refining, stepwise recrystallization, and size separation techniques The separation from the treated feedstock recovered after the selection of the advanced diamond-like component. -15- This paper size applies to the national standard (CNS) A4 (210X297 mm) of b