CN1566943A - Method for separating and preparing neutral nitrogen compound in crude oil - Google Patents
Method for separating and preparing neutral nitrogen compound in crude oil Download PDFInfo
- Publication number
- CN1566943A CN1566943A CN 03147795 CN03147795A CN1566943A CN 1566943 A CN1566943 A CN 1566943A CN 03147795 CN03147795 CN 03147795 CN 03147795 A CN03147795 A CN 03147795A CN 1566943 A CN1566943 A CN 1566943A
- Authority
- CN
- China
- Prior art keywords
- crude oil
- nitrogen compound
- neutral nitrogen
- separating
- millimeters
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 230000007935 neutral effect Effects 0.000 title claims abstract description 27
- 229910017464 nitrogen compound Inorganic materials 0.000 title claims abstract description 26
- 150000002830 nitrogen compounds Chemical class 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 22
- 239000010779 crude oil Substances 0.000 title claims abstract description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000003463 adsorbent Substances 0.000 claims abstract description 11
- -1 alkyl silica gel Chemical compound 0.000 claims description 11
- 239000000741 silica gel Substances 0.000 claims description 10
- 229910002027 silica gel Inorganic materials 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims description 7
- 239000011521 glass Substances 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 abstract description 8
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 4
- 230000001376 precipitating effect Effects 0.000 abstract 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical class C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- HIAGSPVAYSSKHL-UHFFFAOYSA-N 1-methyl-9h-carbazole Chemical class N1C2=CC=CC=C2C2=C1C(C)=CC=C2 HIAGSPVAYSSKHL-UHFFFAOYSA-N 0.000 description 4
- UGFOTZLGPPWNPY-UHFFFAOYSA-N 3.4-Benzo-carbazol Natural products C1=CC=CC2=C3C4=CC=CC=C4NC3=CC=C21 UGFOTZLGPPWNPY-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- YTFVRYKNXDADBI-UHFFFAOYSA-N 3,4,5-trimethoxycinnamic acid Chemical compound COC1=CC(C=CC(O)=O)=CC(OC)=C1OC YTFVRYKNXDADBI-UHFFFAOYSA-N 0.000 description 2
- ROEOVWIEALGNLM-UHFFFAOYSA-N 5h-benzo[b]carbazole Chemical compound C1=CC=C2C=C3C4=CC=CC=C4NC3=CC2=C1 ROEOVWIEALGNLM-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- PWJYOTPKLOICJK-UHFFFAOYSA-N 2-methyl-9h-carbazole Chemical class C1=CC=C2C3=CC=C(C)C=C3NC2=C1 PWJYOTPKLOICJK-UHFFFAOYSA-N 0.000 description 1
- HJBWJAPEBGSQPR-UHFFFAOYSA-N DMCA Natural products COC1=CC=C(C=CC(O)=O)C=C1OC HJBWJAPEBGSQPR-UHFFFAOYSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 231100000004 severe toxicity Toxicity 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
The invention relates to a separation preparation method for separating and extracting neutral nitrogen compounds from crude oil, which is characterized in that crude oil samples are concentrated in C after normal hexane is used for precipitating asphaltene18On the non-polar adsorbent, filling C on the self-made separation column18Non-polar adsorbent to be adsorbed on C18The method has the advantages of simple process, simple and convenient operation, single used reagent and less amount, reduces the labor intensity of analyzing the neutral nitrogen compound and the degree of harm of an operator by the reagent, and has low cost, short period and strong operability.
Description
Technical field:
The present invention relates to a kind of from crude oil the method for separating and preparing of separation and Extraction neutral nitrogen compound
Background technology:
In the oil and gas geochemistry field, the isolation and identification method of neutral nitrogen compound has been widely used in the knowledge of declaring of oil and gas secondary migration in the crude oil, the method for separating and preparing of neutral nitrogen compound, now most popular both at home and abroad is the two-step approach separation method that Later and Maowen Li developed in the nineties, its separation process figure sees accompanying drawing 2, this separation method is owing to adopting twice different (neutral alumina and acidic silica gel) pillar to separate, so be two-step approach.From our characteristics of this method (deficiency) as can be seen of its flow process: 1) step is various, flow process is longer, and the analytical cycle of a sample needs 3 days time at least; 2) reagent type is many, consumption is big, and toluene severe toxicity, high carcinogenic.3) analysis cost height.
Summary of the invention:
Order of the present invention ground is exactly the method for separating and preparing that designs a kind of new neutral nitrogen compound, and it can be quick, neutral nitrogen compound is separated preparing easily from crude oil, makes it to be convenient in oil-gas exploration the declare knowledge of staff to oil and gas secondary migration.
Neutral nitrogen compound is meant the class nitrogen-containing compound with pyrroles's configuration, the neutral nitrogen compound that relates in this method mainly refers to carbazoles (comprising carbazole, methyl carbazole series, 2 methyl carbazole series etc.) and benzo carbazoles (comprising benzo [a] carbazole, benzo [b] carbazole, benzo [c] carbazole etc.), the following diagram of chemical constitution of carbazole and benzo carbazole:
The separation preparation process of neutral nitrogen compound:
Get 0.08 the gram crude oil sample, with normal hexane with asphaltene precipitation after, concentrate in 0.5 the gram 18 alkyl silica gel (C
18) on the non-polar adsorbent,
1) on homemade separating column, fills 1.5 gram 18 alkyl silica gel (C
18) non-polar adsorbent, will be adsorbed in 18 alkyl silica gel (C
18) sample on the non-polar adsorbent changes over to, with 6 ml n-hexane drip washing, removes stable hydrocarbon and aromatic hydrocarbons;
2) use 15 ml n-hexanes, divide and continue drip washing 3 times, flush out neutral nitrogen compound.
Homemade separating column is to be made by common glass, and the following segment length of pillar is 450 millimeters, and internal diameter is 5 millimeters, and path length is 150 millimeters in the epimere, and internal diameter is 15 millimeters.The upper end of pillar joins by ground and nitrogen connector (also being that glass is made), changes pillar at sample, and leacheate (normal hexane) carries out drip washing by nitrogen gas pressure to sample.
The characteristics of method: this method technology is simple, easy and simple to handle, and use reagent is single, amount is few, has reduced the labour intensity of neutral nitrogen compound analysis and the degree that the operator is endangered by reagent.In addition, this method cost is low, the cycle short, and is workable.
Description of drawings:
Fig. 1. the separating column structural representation
Fig. 2. two-step approach separation method process flow diagram
Fig. 3. the chromatogram-mass spectrogram of neutral nitrogen compound
Specific embodiments:
Embodiment 1
Get the crude oil sample of the sheep three wooden crude oil of 0.08 gram Dagang Oilfield, after normal hexane precipitation bitumens matter, concentrate in the 18 alkyl silica gel (C of 0.5 gram
18) on the non-polar adsorbent.
1) on homemade separating column, fills 1.5 gram 18 alkyl silica gel (C
18) non-polar adsorbent, will be adsorbed in 18 alkyl silica gel (C
18) sample on the non-polar adsorbent changes over to, with 6 ml n-hexane drip washing, removes stable hydrocarbon and aromatic hydrocarbons.
2) use 15 ml n-hexanes, divide and continue drip washing 3 times, flush out neutral nitrogen compound.
Become separating column with common glass, the following segment length (1) of pillar is 450 millimeters, and internal diameter is 5 millimeters, and the interior path length of epimere (2) is 150 millimeters, and internal diameter is 15 millimeters.The upper end of pillar joins by ground (3) and nitrogen connector (4) (also being that glass is made), and after sample changed pillar over to, leacheate (normal hexane) carried out drip washing by nitrogen gas pressure to sample.
The neutral nitrogen compound that chromatogram-mass spectrum is identified is in the distribution of lessivation: (following table)
Each step is gone out the contrast of compound chromaticness analysis result
| Sequence number | Reagent dosage | Neutral nitrogen compound |
| ??1 | The 3ml normal hexane | Do not have (containing high concentration stable hydrocarbon, aromatic hydrocarbons) |
| ??2 | The 3ml normal hexane | Do not have (containing stable hydrocarbon, aromatic hydrocarbons) |
| ????3 | The 3ml normal hexane | (containing a small amount of stable hydrocarbon, aromatic hydrocarbons) arranged |
| ????4 | The 5ml normal hexane | Have |
| ????5 | The 4ml normal hexane | Have |
| ????6 | The 3ml normal hexane | Have |
| ????7 | The 3ml normal hexane | Do not have |
From table as can be seen: 6 milliliters normal hexane can be removed stable hydrocarbon and aromatic hydrocarbons substantially, and 15 milliliters normal hexane continues drip washing can obtain purer neutral nitrogen compound.Chromatogram-the mass spectrogram of neutral nitrogen compound is seen Fig. 3.
The repeatability of method: the sample to same crude oil is done parallel analysis, the results are shown in following table, from table as can be seen: this method repeated very good.
CA represents carbazole in the table, and BCA represents the benzo carbazole, and MCA represents the methyl carbazole, and DMCA represents 2 methyl carbazoles, and TMCA represents 3 methyl carbazoles, [a] expression benzo [a] carbazole, [c] expression benzo [c] carbazole.
Embodiment 2～3
Get the crude oil of 0.08 gram Liaohe Oil Field and the crude oil of Xinjiang Oilfield respectively, with equipment and the method for embodiment 1, the preparation neutral nitrogen compound, the chromatogram-mass spectrogram of neutral nitrogen compound, repeatability are with embodiment 1.
Embodiment 4～7
Crude oil sample picks up from four structural belts in East River wetlands district: i.e. No. 4 brokebacks of East River tiltedly, No. 6 anticlines of East River, No. 1 anticline of East River and East River 3 north structures, with the equipment of embodiment 1 and method, the crude oil amount of getting, the preparation neutral nitrogen compound is inferred the possible migration path of crude oil according to the absolute content of isolated carbazole compound from sample.
Claims (2)
1. the method for separating and preparing of neutral nitrogen compound in the crude oil is characterized in that: get the crude oil sample of 0.08 gram, after normal hexane precipitation bitumens matter, concentrate in the 18 alkyl silica gel (C of 0.5 gram
18) on the non-polar adsorbent,
(1) on homemade separating column, fills 1.5 gram 18 alkyl silica gel (C
18) non-polar adsorbent, will be adsorbed in 18 alkyl silica gel (C
18) sample on the non-polar adsorbent changes over to, with 6 ml n-hexane drip washing, removes stable hydrocarbon and aromatic hydrocarbons.
(2) use 15 ml n-hexanes, divide and continue drip washing 3 times, flush out neutral nitrogen compound.
2. the used equipment of method for separating and preparing of neutral nitrogen compound in the crude oil according to claim 1, it is characterized in that: separating column is to be made by common glass, the following segment length of pillar is 450 millimeters, internal diameter is 5 millimeters, path length is 150 millimeters in the epimere, internal diameter is 15 millimeters, and the upper end of pillar joins by ground and nitrogen connector (also being that glass is made).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03147795 CN1239903C (en) | 2003-06-27 | 2003-06-27 | Method for separating and preparing neutral nitrogen compound in crude oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03147795 CN1239903C (en) | 2003-06-27 | 2003-06-27 | Method for separating and preparing neutral nitrogen compound in crude oil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1566943A true CN1566943A (en) | 2005-01-19 |
| CN1239903C CN1239903C (en) | 2006-02-01 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 03147795 Expired - Fee Related CN1239903C (en) | 2003-06-27 | 2003-06-27 | Method for separating and preparing neutral nitrogen compound in crude oil |
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| Country | Link |
|---|---|
| CN (1) | CN1239903C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101776536B (en) * | 2009-01-14 | 2014-02-19 | 中国科学院地理科学与资源研究所 | Apparatus for absorbing ion in water |
| CN105588740A (en) * | 2014-10-20 | 2016-05-18 | 中国石油天然气股份有限公司 | Sample flushing device and method for extracting crude oil and measuring content of oil-bearing rock |
| CN106324158A (en) * | 2015-06-17 | 2017-01-11 | 中国石油天然气股份有限公司 | Method for solid phase extraction of nitrogen-containing compounds in diesel oil |
| CN112903872A (en) * | 2021-01-15 | 2021-06-04 | 中国石油大学(北京) | Separation method and application of carbazole nitride in petroleum component |
-
2003
- 2003-06-27 CN CN 03147795 patent/CN1239903C/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101776536B (en) * | 2009-01-14 | 2014-02-19 | 中国科学院地理科学与资源研究所 | Apparatus for absorbing ion in water |
| CN105588740A (en) * | 2014-10-20 | 2016-05-18 | 中国石油天然气股份有限公司 | Sample flushing device and method for extracting crude oil and measuring content of oil-bearing rock |
| CN105588740B (en) * | 2014-10-20 | 2018-08-14 | 中国石油天然气股份有限公司 | Sample flushing device and method for extracting crude oil and measuring content of oil-bearing rock |
| CN106324158A (en) * | 2015-06-17 | 2017-01-11 | 中国石油天然气股份有限公司 | Method for solid phase extraction of nitrogen-containing compounds in diesel oil |
| CN106324158B (en) * | 2015-06-17 | 2018-11-16 | 中国石油天然气股份有限公司 | Method for solid phase extraction of nitrogen-containing compounds in diesel oil |
| CN112903872A (en) * | 2021-01-15 | 2021-06-04 | 中国石油大学(北京) | Separation method and application of carbazole nitride in petroleum component |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1239903C (en) | 2006-02-01 |
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Granted publication date: 20060201 |