CN104016826A - Method for preparing alkane from halohydrocarbon - Google Patents
Method for preparing alkane from halohydrocarbon Download PDFInfo
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- CN104016826A CN104016826A CN201410267540.6A CN201410267540A CN104016826A CN 104016826 A CN104016826 A CN 104016826A CN 201410267540 A CN201410267540 A CN 201410267540A CN 104016826 A CN104016826 A CN 104016826A
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- halohydrocarbon
- alkane
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Abstract
The invention relates to a hydrocarbon compound, particularly a method for preparing alkane from halohydrocarbon. The method comprises the following steps: reacting the halohydrocarbon, metal and an initiator, collecting the liquid-phase product, and separating to obtain the alkane. The reaction between the metal and halohydrocarbon implements conversion of the halohydrocarbon; the whole reaction is performed under mild conditions, and does not need any noble metal catalyst, hydrogen, high temperature, high pressure, organic substance extractant process or the like; and by using the non-petrochemical hydrocarbon fuel preparation way, the whole production process has the advantages of lower energy consumption, higher product quality and favorable application prospects. The method has the advantages of simple technique and high efficiency, and is convenient to operate; and the prepared hydrocarbon fuel belongs to a clean renewable energy source and typical green energy source.
Description
Technical field
The present invention relates to hydrocarbon compound, particularly relate to a kind of method of being prepared alkane by halohydrocarbon.
Background technology
Along with transforming and produce the increasingly mature of polyvalent alcohol technology by biomass catalyzing, prepare hydro carbons by polyvalent alcohol and also demonstrate its development potentiality.The sorbyl alcohol that at present existing bibliographical information derives from biomass can be catalytically conveted to C
6～C
9hydrocarbon, but its reaction process complexity, catalyzer costliness, temperature of reaction are higher.But, US Patent No. 5516960 discloses a kind of in the method compared with prepared hydro carbons under mild conditions by sorbyl alcohol, hydroiodic acid HI, phosphorous acid and water reaction, and the product obtaining is C
10～C
18hydro carbons, by product is idoalkane and iodine.The method of wherein removing idoalkane is idoalkane to be reacted with alkali alcosol generate alkene, then generates alkane with hydrogen addition under high-temperature and high-pressure conditions.
Directly catalytic hydrogenation is also the method that halohydrocarbon hydrogenolysis-dehalogenation is conventional, and used catalyst is generally nickel and palladium, but this two kinds of common large usage quantities of catalyzer or be difficult to recycle and reuse.Chinese patent CN1974498A discloses a kind of method that catalytic hydrogenation reductive halogenation hydrocarbon dehalogenation is prepared hydrocarbon, and the method reaction conditions gentleness, catalyzer are capable of circulation, but the catalyzer using is palladium salt catalyst, and process need hydrogen.In a word, these common treating processess all need hydrogen and noble metal catalyst substantially, cause the conversion cost of halohydrocarbon high.
That in view of this, need to develop a kind of more efficient, less energy-consumption prepares the method for hydro carbons by halohydrocarbon.
Summary of the invention
The object of the present invention is to provide a kind of method of being prepared alkane by halohydrocarbon of mild condition.
Concrete steps of the present invention are:
By halohydrocarbon, metal and initiator for reaction, collect liquid product, after separation, obtain alkane.
Described metal can be selected from least one in sodium, iron, silver, zinc etc.
Described initiator can adopt at least one in halogen simple substance, halogen etc.
In described metal and halohydrocarbon, the mol ratio of halogen can be 1.2～5, is preferably 1.5～2.5.
The quality of described initiator can be 0.1%～1.0% of metal quality by mass percentage.
The temperature of described reaction is 60～140 DEG C, the time 0.5～3h of reaction.
Described separation can be by filtering or fractionation by distillation.
Beneficial effect of the present invention is as follows:
In the present invention, metal and reacting of halohydrocarbon have been realized the conversion of halohydrocarbon, whole reaction conditions gentleness, do not need noble metal catalyst, hydrogen, high temperature, high pressure, organic substance extraction agent process etc., adopt the hydrocarbon fuel in non-petrochemical industry source to prepare approach, whole production process energy consumption is lower, quality product is better, has a good application prospect.Preparation technology is simple, easy to operate, efficiency is high, and the hydrocarbon fuel of preparation belongs to clean renewable energy source and the category of typical " green energy resource ".
Brief description of the drawings
Fig. 1 is the GC-MS total ion current figure of 1-iodohexane in embodiment 1.
Fig. 2 is the GC-MS total ion current figure of the hydrocarbon after 1-iodohexane dehalogenation in embodiment 1.
Fig. 3 is the GC-MS total ion current figure of parent material in embodiment 2.
Fig. 4 is the GC-MS total ion current figure of halohydrocarbon dehalogenation after product in embodiment 2.
Embodiment
Below in conjunction with embodiment, the present invention is illustrated, embodiment described below is exemplary, does not limit the scope of the invention.The chemical reagent adopting in the embodiment of the present invention is commercial.
Embodiment 1
Get 1-iodohexane, zinc powder, the each 10.0g of elemental iodine, 5.0g, 0.01g in round-bottomed flask, magnetic agitation rotating speed is 800rpm, in 80 DEG C of reaction 0.5h, collects oil phase 3.9g after filtration.The GC-MS figure of the hydrocarbon after 1-iodohexane and dehalogenation is shown in respectively Fig. 1 and Fig. 2.The hexene that visible 1-iodohexane has been converted into hexane completely and has seldom measured.
Embodiment 2
Sorbyl alcohol reacts the oil-phase product of producing and carries out gaschromatographic mass spectrometric analysis with hydroiodic acid HI, as shown in Figure 3, main component is 2-iodohexane to result, and C
12and C
18hydro carbons.In 9.5g oil-phase product, add 4.0g zinc powder, temperature of reaction is 60 DEG C, and the reaction times is 1h, and therefore oil-phase product contains a small amount of elemental iodine, does not therefore need extra iodine.Reaction finishes rear leaving standstill, and is insoluble to the zinc iodide of hydrocarbon and excessive zinc and is precipitated out, and zinc iodide can be used for organic catalyst compound, sanitas, electrolytic solution and analytical reagent etc.Liquid hydrocarbon quality is 6.8g, and as shown in Figure 4, main component is C to gaschromatographic mass spectrometry detected result
6h
14and C
12and C
18hydro carbons, this product enters water distilling apparatus 8 and further separates, underpressure distillation condition is 0.02MPa, 30 DEG C, treat receiving bottle no longer include drop ooze stop distillation, the lower boiling C being distilled out
6h
14and minute quantity C
6h
12quality is 0.3g; The liquid of residue 6.5g is C
12and C
18hydro carbons, gaschromatographic mass spectrometry detected result as shown in Figure 4.Visible, this method is not only converted into hydro carbons by halohydrocarbon, has also removed the iodine in oil phase, but oil composition has not been impacted.
Embodiment 3
Get 1-iodohexane, magnesium powder, the each 12.0g of elemental iodine, 5.0g, 0.005g in round-bottomed flask, magnetic agitation rotating speed is 800rpm, in 140 DEG C of reaction 1.5h, after filtration, collect oil phase 4.8g, GC-MS detected result shows that 1-iodohexane transforms completely, in product, hexane is 47%, and hexene is 4%, and n-dodecane is 49%.
Embodiment 4
Get 1-iodohexane, magnesium powder, the each 12.0g of elemental iodine, 4.0g, 0.02g in round-bottomed flask, magnetic agitation rotating speed is 800rpm, in 70 DEG C of reaction 2.0h, collects oil phase 4.8g after filtration.GC-MS detected result shows that 1-iodohexane transforms completely, and in product, hexane is 46%, and hexene is 6%, and n-dodecane is 48%.
Embodiment 5
Get 1,6-bis-iodohexanes, magnesium powder, the each 12.0g of elemental iodine, 3.5g, 0.03g are in round-bottomed flask, magnetic agitation rotating speed is 800rpm, in 80 DEG C of reaction 3h, after filtration, collect oil phase 3.0g, GC-MS detected result shows 1,6-bis-iodohexanes transform completely, in product, hexane is 63%, and hexene is 8%, and n-dodecane is 29%.
Embodiment 6
Get 1,6-bis-iodohexanes, zinc powder, the each 12.0g of elemental iodine, 3.0g, 0.03g are in round-bottomed flask, magnetic agitation rotating speed is 800rpm, in 100 DEG C of reaction 1h, after filtration, collect oil phase 2.9g, GC-MS detected result shows that 1,6-, bis-iodohexanes transform completely, in product, hexane is 95%, and hexene is 5%.
Embodiment 7
Get 1,6-bis-iodohexanes, zinc powder, the each 12.0g of elemental iodine, 3.0g, 0.02g are in round-bottomed flask, magnetic agitation rotating speed is 800rpm, in 110 DEG C of reaction 2h, after filtration, collect oil phase 3.0g, GC-MS detected result shows that 1,6-, bis-iodohexanes transform completely, in product, hexane is 93%, and hexene is 7%.
Embodiment 8
Get 1-iodohexane, zinc powder, the each 8.0g of elemental iodine, 4.2g, 0.02g in round-bottomed flask, magnetic agitation rotating speed is 800rpm, in 120 DEG C of reaction 2h, collects oil phase 3.2g after filtration, GC-MS detected result shows that 1-iodohexane transforms completely, and in product liquid, hexane is 100%.
Embodiment 9
Get 1,6-bis-iodohexanes, zinc powder, the each 11.0g of elemental iodine, 10.5g, 0.06g are in round-bottomed flask, magnetic agitation rotating speed is 800rpm, in 120 DEG C of reaction 2.5h, after filtration, collect oil phase 2.6g, GC-MS detected result shows that 1,6-, bis-iodohexanes transform completely, in product, hexane is 92%, and hexene is 8%.
Embodiment 10
Get 1-iodohexane, zinc powder, the each 6.5g of elemental iodine, 4.9g, 0.03g in round-bottomed flask, magnetic agitation rotating speed is 800rpm, in 110 DEG C of reaction 2h, after filtration, collect oil phase 2.6g, GC-MS detected result shows that 1-iodohexane transforms completely, and in product, hexane is 95%, and hexene is 5%.
To the above-mentioned explanation of embodiments of the invention, professional and technical personnel can be realized or use, can, in the situation that not departing from principle of the present invention or scope, realize in other embodiments.Therefore, the present invention will can not be restricted to these embodiment shown in this article, and its scope is limited by claims and equivalent thereof.
Claims (8)
1. prepared a method for alkane by halohydrocarbon, it is characterized in that its concrete steps are:
By halohydrocarbon, metal and initiator for reaction, collect liquid product, after separation, obtain alkane.
2. a kind of method of being prepared alkane by halohydrocarbon as claimed in claim 1, is characterized in that described metal is selected from least one in sodium, iron, silver, zinc.
3. a kind of method of being prepared alkane by halohydrocarbon as claimed in claim 1, is characterized in that described initiator adopts at least one in halogen simple substance, halogen.
4. a kind of method of being prepared alkane by halohydrocarbon as claimed in claim 1, the mol ratio that it is characterized in that halogen in described metal and halohydrocarbon is 1.2～5.
5. a kind of method of being prepared alkane by halohydrocarbon as claimed in claim 4, the mol ratio that it is characterized in that halogen in described metal and halohydrocarbon is 1.5～2.5.
6. a kind of method of being prepared alkane by halohydrocarbon as claimed in claim 1, the quality that it is characterized in that described initiator is 0.1%～1.0% of metal quality by mass percentage.
7. a kind of method of being prepared alkane by halohydrocarbon as claimed in claim 1, the temperature that it is characterized in that described reaction is 60～140 DEG C, the time of reaction is 0.5～3h.
8. a kind of method of being prepared alkane by halohydrocarbon as claimed in claim 1, is characterized in that described separation is by filtering or fractionation by distillation.
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|---|---|---|---|
| CN201410267540.6A CN104016826A (en) | 2014-06-16 | 2014-06-16 | Method for preparing alkane from halohydrocarbon |
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| CN201410267540.6A CN104016826A (en) | 2014-06-16 | 2014-06-16 | Method for preparing alkane from halohydrocarbon |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109912382A (en) * | 2019-04-04 | 2019-06-21 | 厦门大学 | A method of 2- iodohexane is prepared by raw material of sorbierite |
-
2014
- 2014-06-16 CN CN201410267540.6A patent/CN104016826A/en active Pending
Non-Patent Citations (3)
| Title |
|---|
| 俞凌翀编: "《有机化学中的人名反应》", 31 May 1984, 科学出版社 * |
| 袁开基编著: "《理论有机化学（下册）》", 30 November 1963, 上海科学技术出版社 * |
| 邢其毅等: "《基础有机化学（上册）》", 30 June 2005, 高等教育出版社 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109912382A (en) * | 2019-04-04 | 2019-06-21 | 厦门大学 | A method of 2- iodohexane is prepared by raw material of sorbierite |
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Application publication date: 20140903 |
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