CN101289491B - Method for separating sterane and hopane from crude oil or rock extract by using 10X molecular sieve - Google Patents
Method for separating sterane and hopane from crude oil or rock extract by using 10X molecular sieve Download PDFInfo
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- 239000002808 molecular sieve Substances 0.000 title claims abstract description 31
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 11
- 239000011435 rock Substances 0.000 title claims abstract description 10
- 239000010779 crude oil Substances 0.000 title claims abstract description 9
- ZRLNBWWGLOPJIC-PYQRSULMSA-N A'-neogammacerane Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1C(C)C ZRLNBWWGLOPJIC-PYQRSULMSA-N 0.000 title abstract 8
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 title abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 238000005303 weighing Methods 0.000 claims abstract description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000741 silica gel Substances 0.000 claims abstract description 7
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000945 filler Substances 0.000 claims abstract description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000002245 particle Substances 0.000 claims abstract description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 43
- UACIBCPNAKBWHX-CTBOZYAPSA-N gonane Chemical compound C1CCC[C@@H]2[C@H]3CC[C@@H]4CCC[C@H]4[C@@H]3CCC21 UACIBCPNAKBWHX-CTBOZYAPSA-N 0.000 claims description 29
- 239000004215 Carbon black (E152) Substances 0.000 claims description 12
- 229930195733 hydrocarbon Natural products 0.000 claims description 12
- 150000002430 hydrocarbons Chemical class 0.000 claims description 12
- 238000005406 washing Methods 0.000 claims description 12
- 238000007873 sieving Methods 0.000 claims description 9
- 230000004913 activation Effects 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 3
- 238000012856 packing Methods 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 5
- 238000004949 mass spectrometry Methods 0.000 abstract description 5
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract description 3
- 238000002386 leaching Methods 0.000 abstract 4
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 abstract 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 abstract 2
- 238000001514 detection method Methods 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 description 9
- WEEGYLXZBRQIMU-UHFFFAOYSA-N Eucalyptol Chemical compound C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- 238000011160 research Methods 0.000 description 6
- 230000000155 isotopic effect Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- GKBHKNPLNHLYHT-OWDZWQNUSA-N 5alpha-stigmastane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]2(C)CC1 GKBHKNPLNHLYHT-OWDZWQNUSA-N 0.000 description 2
- WAAWMJYYKITCGF-XRWQUZPPSA-N 5beta-ergostane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@H](C)C(C)C)[C@@]2(C)CC1 WAAWMJYYKITCGF-XRWQUZPPSA-N 0.000 description 2
- XIIAYQZJNBULGD-XWLABEFZSA-N 5α-cholestane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 XIIAYQZJNBULGD-XWLABEFZSA-N 0.000 description 2
- -1 Keniing F Chemical compound 0.000 description 2
- 239000000090 biomarker Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- XIIAYQZJNBULGD-CJPSHIORSA-N β-cholestane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 XIIAYQZJNBULGD-CJPSHIORSA-N 0.000 description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
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- Treatment Of Liquids With Adsorbents In General (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
The invention relates to a molecular sieve separation preparation method of sterane and hopane, which comprises the steps of taking 60mg of crude oil or rock extract, filling a column with 6g of silica gel with the particle diameter of 40 microns, and leaching 15ml of n-hexane to prepare saturated hydrocarbon; filling a ZSM molecular sieve with the mass about 100 times that of the saturated hydrocarbon into a column, and leaching 20ml of isooctane to prepare cyclic hydrocarbon; filling a 10X molecular sieve with the mass about 300 times that of the cyclic hydrocarbon into a column, and leaching with 80ml of n-pentane after 30 minutes to prepare a fraction; recovering and volatilizing the solvent of the fractions, weighing the mass of the solvent, filling 200 times of 10X molecular sieve into a column, and leaching with 10ml after 30 minutes to obtain sterane; drying the column filler obtained in the step 3 by using nitrogen, and extracting for 12 hours by using isooctane to obtain hopane; the separation effect is good through the detection of chromatography-mass spectrometry, and is basically consistent with the effect of a separation spectrogram displayed abroad, and the enriching and separating method of the hopane is simple to operate.
Description
Technical field:
The present invention relates to a kind of with the gonane in 10X molecular sieving enrichment crude oil or the rock extract and the method for alkane suddenly.
Background technology:
Gonane and suddenly alkane be a class biomarker compound very important in crude oil and the rock extract, by to gonane and the research of alkane suddenly, can determine the information of the aspects such as matrix type, sedimentary environment and ripening degree of oil, be the major objective compound of researchs such as OIL SOURCE CORRELATION and oil and gas secondary migration.Along with the development of detailed hydrocarbon stable isotope determination technology, the oil and gas geochemistry worker begins the isotopic research of biomarker compound, to obtain more, more detailed information, solves an indeterminable difficult problem in the past.Realize the gonane and the stable isotope determination of alkane suddenly, must from oil or rock extract, separate it, get rid of the interference of its condistillation component.Abroad, Kenig F. etc. utilizes the ultra-steady Y molecular sieve filler to isolate gonane and alkane suddenly on high performance liquid chromatography, has realized its isotopic mensuration.But used domestic can't the purchases of ultra-steady Y molecular sieve such as Keniing F, the home-made ultra-steady Y molecular sieve can't repeat its result.Another family realize gonane and suddenly the alkane stable isotope determination be the oil gas earth laboratory of Stanford Univ USA, showed the result in the AAAPG geochemistry international conference that Moldowan J.M. holds in Beijing, but how separating the gonane that obtains says nothing, belong to secrecy technology, external service only is provided.At home, bear is waited by force forever the particular sample of Karamay oilfield has been carried out the enrichment of alkane suddenly, but utilize the 10X molecular sieve to gonane and suddenly the Separation Research of alkane still be a blank, up to the present, also do not see report about this respect.
Reference:
1、Kenig，F.，Popp，B.N.and?Summons，R.E.Preparative?HPLC?withultrastable-Y?zeolite?for?compound-specific?carbon?isotopic?analyses.Organic?Geochem.，2000，31，1087-1094.
2、Moldowan?J.M.and?Dahl?J.，AAAPG，2004，Beijing，China
3, the strong forever Geng An pine of bear Liu gets terpenoid free carbon isotopics Science Bulletin 1998,43 (12), 1312-1315. in the light Karamay oilfield viscous crude
Summary of the invention:
Purpose of the present invention is exactly to utilize homemade molecular sieve to realize gonane and separating of alkane suddenly, fills up the blank of China in this invention research, for the research of processes such as the oil gas matrix source of complex areas such as superimposed basin, one-tenth Tibetan provides new technical support.
Gonane is very close with the structure of alkane suddenly, following structural formula, and with the gonane of carbon number with the retention behavior of alkane on adsorption chromatography is very close suddenly, very difficult that structure is the close gonane of traditional method separates with alkane suddenly.The present invention utilizes the gonane and the difference of alkane molecular diameter suddenly, utilizes home-made 10X molecular sieve to realize the separating of gonane and alkane suddenly, enrichment.
Gonane and alkane molecular structural formula suddenly
10X molecular sieving, enrichment gonane and the process of alkane suddenly:
1, crude oil or rock extract 60mg, with the silica gel filling pillar of 40 microns of 6g particle diameters, stable hydrocarbon is prepared in the drip washing of 15ml normal hexane;
2, solvent flashing on Nitrogen evaporator, the quality of weighing stable hydrocarbon is got the about 100 times ZSM molecular sieve filling pillar of stable hydrocarbon quality, and cyclic hydrocarbon is prepared in the drip washing of 20ml octane-iso;
3, solvent flashing on Nitrogen evaporator, the quality of weighing cyclic hydrocarbon is got the about 300 times 10X molecular sieve filling pillar of cyclic hydrocarbon quality, prepares cut with the drip washing of 80ml Skellysolve A after 30 minutes;
The solvent of 4, recovery, volatile fraction, its quality of weighing is got 200 times 10X molecular sieve filling pillar, and the Skellysolve A drip washing with 10ml after 30 minutes obtains gonane;
5, after the column packing of step 3 dries up with nitrogen, after 12 hours, obtain alkane suddenly with the octane-iso extracting.
The used pillar of preceding four step column chromatographies requires to meet nitrogen pressure 0.2Mpa, and the leacheate take-off rate is not more than 30 droplets/minute, and the used filler of filling pillar need activate 10 hours before use, and activation temperature is respectively: silica gel, 220 ℃; The ZSM molecular sieve, 450 ℃; The 10X molecular sieve, 470 ℃.
The core of invention was the 3rd, 4,5 steps, promptly used home-made 10X molecular sieve and did filler, separated respectively and prepared gonane and alkane suddenly.
The invention effect:
The gonane that 10X molecular sieve concentration and separation is gone out and suddenly alkane carry out chromatogram-mass spectrum and identify (selecting ion to contain all ions that saturated hydrocarbon component detects), the evaluation collection of illustrative plates of gonane is seen accompanying drawing 2, the evaluation collection of illustrative plates of alkane is seen accompanying drawing 3 suddenly.Relatively can see with the total ion current figure before the 10X separation and concentration: the present invention can effectively separate and enrichment gonane and alkane suddenly, makes isotopic mensuration become possibility.Separating effect is compared (reference 2) basically identical with the spectrogram effect that MoldowanJ.M. shows in the international conference of AAPG geochemistry, illustrate utilize home-made 10X molecular sieving gonane and suddenly alkane be feasible, separation and concentration gonane and alkane effectively suddenly.Present method institute enrichment method of alkane is suddenly compared than the method for document 3, uses the 10X molecular sieve instead, because particle is bigger, operates more simple, convenient.
Description of drawings:
Fig. 1. the separator column structural representation;
Fig. 2 .10X molecular sieving goes out the chromatography-mass spectroscopy total ion current figure of gonane;
Fig. 3 .10X molecular sieving goes out the chromatography-mass spectroscopy total ion current figure of alkane suddenly;
Fig. 4. remove sample chromatogram-mass spectrum total ion current figure that positive structure hydrocarbon is handled without molecular sieve.
Embodiment:
1, crude oil or rock extract 60mg, with the silica gel filling pillar of 40 microns of 6g particle diameters, stable hydrocarbon is prepared in the drip washing of 15ml normal hexane.
2, solvent flashing on Nitrogen evaporator, the quality of weighing stable hydrocarbon is got the about 100 times ZSM molecular sieve filling pillar of stable hydrocarbon quality, and cyclic hydrocarbon is prepared in the drip washing of 20ml octane-iso.
3, solvent flashing on Nitrogen evaporator, the quality of weighing cyclic hydrocarbon is got the about 300 times 10X molecular sieve filling pillar of cyclic hydrocarbon quality, prepares cut Z with the drip washing of 80ml Skellysolve A alkane after 30 minutes.
4, at the solvent of recovery, volatile fraction Z, its quality of weighing is got 200 times 10X molecular sieve filling pillar, and the drip washing with 10ml after 30 minutes obtains gonane.
5, after the column packing of step 3 dries up with nitrogen, after 12 hours, obtain alkane suddenly with the octane-iso extracting.
The used pillar of preceding four step column chromatographies requires to connect nitrogen pressure 0.2Mpa (see figure 1), and pillar is to be made of nitrogen connecting joint 1 and shaft 4, by the bistrique 2 of nitrogen connecting joint below and the ground 3 of shaft top the nitrogen connecting joint is connected with shaft.The leacheate take-off rate is not more than 30 droplets/minute.The used filler of filling pillar need activate 10 hours before use, and activation temperature is respectively: silica gel, 220 ℃; The ZSM molecular sieve, 450 ℃; The 10X molecular sieve, 470 ℃.
The 10X molecular sieving goes out the chromatography-mass spectroscopy total ion current of gonane and sees Fig. 2.
Wherein:
(1) 5 α, 14 α, 17 α-cholestane 20S; (2) 5 α, 14 β, 17 β-cholestane 20R;
(3) 5 α, 14 β, 17 β-cholestane 20S; (4) 5 α, 14 α, 17 α-cholestane 20R;
(5) 13 β, 17 α-rearrangement sitostane 20R; (6) 13 β, 17 α-rearrangement sitostane 20S;
(7) 5 α, 14 α, 17 α-ergostane 20S; (8) 5 α, 14 β, 17 β-ergostane 20R;
(9) 5 α, 14 β, 17 β-ergostane 20S; (10) 5 α, 14 α, 17 α-ergostane 20R;
(11) 5 α, 14 α, 17 α-sitostane 20S; (12) 5 α, 14 β, 17 β-sitostane 20R;
(13) 5 α, 14 β, 17 β-sitostane 20S; (14) 5 α, 14 α, 17 α-sitostane 20R;
The 10X molecular sieving goes out suddenly the chromatography-mass spectroscopy total ion current of alkane and sees Fig. 3.
Wherein:
(1) C
20Tricyclic terpane (2) C
21Tricyclic terpane
(3) C
22Tricyclic terpane (4) C
23Tricyclic terpane
(5) C
24Tricyclic terpane (6) 17 α (H), alkane suddenly falls in 21 β (H)-30-;
(7) 17 α (H), 21 β (H)-Huo alkane; (8) 17 β (H), 21 α (H)-Huo alkane;
(9) 7 α (H), 21 β (H)-29-rises alkane 22S suddenly; (10) 7 α (H), 21 β (H)-29-rises alkane 22R suddenly;
(11) 7 α (H), two liters of 21 β (H)-29-are alkane 22S suddenly; (12) 7 α (H), two liters of 21 β (H)-29-are alkane 22R suddenly;
(13) 7 α (H), three liters of 21 β (H)-29-are alkane 22S suddenly; (14) 7 α (H), three liters of 21 β (H)-29-are alkane 22R suddenly;
(15) 7 α (H), four liters of 21 β (H)-29-are alkane 22S suddenly; (16) 7 α (H), four liters of 21 β (H)-29-are alkane 22R suddenly;
(17) 7 α (H), five liters of 21 β (H)-29-are alkane 22S suddenly; (18) 7 α (H), five liters of 21 β (H)-29-are alkane 22R suddenly;
Remove positive structure hydrocarbon and see Fig. 4 without the sample chromatogram-mass spectrum total ion current of molecular sieve processing.
Claims (1)
1. the gonane in 10X molecular sieving crude oil or the rock extract and the method for alkane suddenly is characterized in that:
(1), get crude oil or rock extract 60mg, with the silica gel filling pillar of 40 microns of 6g particle diameters, stable hydrocarbon is prepared in the drip washing of 15ml normal hexane;
(2), on Nitrogen evaporator solvent flashing, the quality of weighing stable hydrocarbon is got the ZSM molecular sieve filling pillar of 100 times of stable hydrocarbon quality, cyclic hydrocarbon is prepared in the drip washing of 20ml octane-iso;
(3), on Nitrogen evaporator solvent flashing, the quality of weighing cyclic hydrocarbon is got the 10X molecular sieve filling pillar of 300 times of cyclic hydrocarbon quality, prepares cut with the drip washing of 80ml Skellysolve A after 30 minutes;
(4), the solvent of recovery, volatile fraction, its quality of weighing is got 200 times 10X molecular sieve filling pillar, the Skellysolve A drip washing with 10ml after 30 minutes obtains gonane;
(5), after the column packing of step (3) dries up with nitrogen, after 12 hours, obtain alkane suddenly with the octane-iso extracting;
Preceding four step column chromatographies used pillars meet nitrogen pressure 0.2Mpa, leacheate take-off rate＜30 droplet/minute, and the used filler of filling pillar need activate 10 hours before use, and activation temperature is respectively: 220 ℃ in silica gel; 450 ℃ in ZSM molecular sieve; 470 ℃ in 10X molecular sieve.
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Families Citing this family (4)
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| CN104628809B (en) * | 2013-11-13 | 2016-09-07 | 中国石油天然气股份有限公司 | Method for separating and enriching biomarker compounds sterane and hopane by using molecular sieve combination |
| CN106124660B (en) * | 2016-07-04 | 2018-11-16 | 中国石油天然气股份有限公司 | Method for separating alkylbenzene compounds from petroleum |
| CN113804535B (en) * | 2020-06-11 | 2022-12-16 | 中国石油大学(北京) | Method and device for enriching C15-C32 molecular marker of wellhead dry gas |
| CN112625082B (en) * | 2020-12-14 | 2022-05-24 | 长江大学 | Method for separating and purifying hopane by neutral alumina |
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