CN105670679B - A kind of method for preparing long chain alkane and aromatic hydrocarbons simultaneously by raw material of oleic acid - Google Patents
A kind of method for preparing long chain alkane and aromatic hydrocarbons simultaneously by raw material of oleic acid Download PDFInfo
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- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 title claims abstract description 45
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 title claims abstract description 45
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 239000005642 Oleic acid Substances 0.000 title claims abstract description 45
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 title claims abstract description 45
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 title claims abstract description 45
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 title claims abstract description 45
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims abstract description 44
- 150000001335 aliphatic alkanes Chemical class 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 24
- 239000002994 raw material Substances 0.000 title claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000001914 filtration Methods 0.000 claims abstract description 15
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 14
- 239000012263 liquid product Substances 0.000 claims abstract description 14
- 239000007790 solid phase Substances 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 26
- 239000001257 hydrogen Substances 0.000 abstract description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 23
- 239000003795 chemical substances by application Substances 0.000 abstract description 5
- 230000003197 catalytic effect Effects 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 150000002431 hydrogen Chemical class 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 47
- 238000010792 warming Methods 0.000 description 16
- 239000000446 fuel Substances 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- 238000006114 decarboxylation reaction Methods 0.000 description 9
- 238000005516 engineering process Methods 0.000 description 8
- 238000005899 aromatization reaction Methods 0.000 description 7
- 239000004519 grease Substances 0.000 description 7
- 238000006356 dehydrogenation reaction Methods 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- 239000002028 Biomass Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- NDJKXXJCMXVBJW-UHFFFAOYSA-N Heptadecane Natural products CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000003350 kerosene Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000295 fuel oil Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 206010003694 Atrophy Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive 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
- 238000004458 analytical method Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000001736 capillary Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- -1 heptadecane Alkane Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Classifications
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
Abstract
The present invention relates to a kind of method for preparing long chain alkane and aromatic hydrocarbons simultaneously by raw material of oleic acid, comprise the following steps:1) oleic acid and catalyst, heat temperature raising reaction are added in high-temperature high-pressure reaction kettle;Described catalyst is Pt/C;2) reaction product is cooled down, organic solvent dissolving, and liquid product and solid-phase catalyst are obtained after filtering.Not additional any hydrogen, hydrogen supply agent or solvent in above-mentioned preparation method, using oleic acid and Pt/C catalytic action one-step synthesis long chain alkane and aromatic hydrocarbons, yield can be respectively up to 72% and more than 19%.
Description
Technical field
The present invention relates to the preparation method of long chain alkane and aromatic hydrocarbons, and in particular to one kind prepares length simultaneously by raw material of oleic acid
The method of alkane and aromatic hydrocarbons.
Background technology
With developing rapidly for aircraft industry, it will be got on the car to the amount of carbon dioxide produced by the year two thousand fifty aircraft more than ground row
The summation put, and with the atrophy of petroleum resources, crude oil price will when the river rises the boat goes up, airline is faced huge existence
Pressure.Under the pressure of pressure, people are hardy seeking the substitute of traditional fossil energy, biology boat coal be using renewable resource as
The aviation kerosine of raw material production, compared with conventional petroleum base aviation kerosine, not only has drop well in whole life cycle
The effect of low carbon dioxide emission, but also be regenerative resource, the research and development application of bio-aviation fuel turns into international airline
One of main trend of industry future development.Aviation Fuel basic composition is alkane of the carbon chain lengths between 8-17, cycloalkane,
Aromatic hydrocarbons and a small amount of additive.Although alkane has more preferable combustibility, the expansion function of the whole elastic system of fuel oil is also
It is that must obtain to be realized by aromatic hydrocarbons, so aromatic hydrocarbons is also essential composition.Grease is the high-energy-density of C, H, O formation
Compound, main component is triglyceride and free fatty.Grease is efficiently converted into catalysis technique biological aviation fuel into
It is most popular and most have one of technology of industrial prospect for biomass energy source domain.
It is with H by the O in grease at present using mainstream technology that grease is the biological aviation fuel of raw material production as hydrogenation deoxidation2O's
Form is sloughed and obtains long chain alkane, and then long chain alkane prepares biological aviation fuel by isomerization.Cheng Jun et al. (CN
103897753A) in H2A kind of biological Aviation Fuel is obtained using HZSM-5 catalysis under atmosphere, however, the H of hydrogenation deoxidation method2
Consumption is larger.
And hydrolysis-decarboxylation method is the new technology being developed in recent years, the complicated low-grade grease of energy processes composition is first hydrolyzed
Aliphatic acid is obtained, then the oxygen in fatty acid molecule is removed by non-hydrogen decarboxylation, hydrocarbon compound is converted into.O during decarboxylation
It is with CO2Form slough, hydrogen is not consumed in terms of deoxidation, thus reduce in biological aviation fuel production process hydrogen consumption.But, oil
(40~60%) containing a large amount of oleic acid in the aliphatic acid that fat hydrolysis is obtained, still suffer from suitable hydrogen consumption.
As being sayed above, aromatic hydrocarbons is very important component in Aviation Fuel, but be difficult from technology it is very ripe plus
Obtain, both typically be from virgin kerosene in hydrogen deoxy technology or F- T synthesis.It is considerably less from biomass production aromatic hydrocarbons, only
The method of some cracking can produce a small amount of aromatic hydrocarbons, and can produce the biology of usually these low energy density of lignin of aromatic hydrocarbons
Matter, and the aromatic hydrocarbons produced is polycyclic mostly, and do not meet requirement (Fuel, 2015.160 of Aviation Fuel:p.375-
385).For preparing aromatic hydrocarbons from grease cracking, although aromatics yield can reach 24%, but condition is very harsh, temperature
Spend for 800 DEG C, the quality requirement of catalyst is 20 times of biomass, and there remains 24% unknown residue.Go out for oleic acid
Hair prepares aromatic hydrocarbons, Rabaev (Fuel, 2015.161:P.287-294 research) shows Pt/Al2O3Under/SAPO-11 catalysis,
Oleic acid is unable to aromatisation, even the yield of the palm oil aromatisation containing 52.8% single unsaturated bond and 12.2% how unsaturated key
Also there was only 1.7%.
《Aliphatic acid (ester) non-hydrogen catalytic decarboxylation repercussion study》(Yang Cuiyue, Chinese excellent MA theses full text number
According to II volume of storehouse engineering science and technology) disclose microalgae grease in a kind of high temperature liquid water and carry out non-hydrogen catalytic decarboxylation and prepare long chain alkane
Method, but the reaction does not have aromatic hydrocarbons generation, and this method needs aqueous solvent, and the presence just because of reaction reclaimed water causes not
The dehydrogenation of saturated acid and its intermediate product is suppressed, so as to can not proceed intramolecular D-A reaction aromatisation, is caused final
Product does not have aromatic hydrocarbons.
The content of the invention
In view of the above-mentioned deficiencies in the prior art, it is an object of the present invention to provide one kind by raw material of oleic acid while preparing long alkane
The method of hydrocarbon and aromatic hydrocarbons, solves from oleic acid and prepares the technical deficiency of biological Aviation Fuel, while solving biological boat
The problem of hydrogen consumption is big in air-fuel oil, hydrogen supply dosage hardly possible is controlled, aromatic hydrocarbons hardly possible is obtained and alkane yield is not high.
The present invention solves the technical scheme that is provided of above-mentioned technical problem:
A kind of method for preparing long chain alkane and aromatic hydrocarbons simultaneously by raw material of oleic acid, comprises the following steps:
1) oleic acid and catalyst, heat temperature raising reaction are added in high-temperature high-pressure reaction kettle;Described catalyst is Pt/C;
2) reaction product is cooled down, organic solvent dissolving, and liquid product and solid-phase catalyst are obtained after filtering.
Step 1 in above-mentioned technical proposal) in only add oleic acid and Pt/C, not additional any hydrogen, hydrogen supply agent or molten
Agent, exactly because without external hydrogen source in system of the present invention, Pt/C can just make a part of oleic acid and its decarboxylate 17
Alkene dehydrogenation and further intramolecular D-A reactions aromatisation hydrogen supply, the hydrogen of generation are rapidly saturated remaining oleic acid into stearic acid, stearic
Acid decarboxylation couples dehydrogenation, decarboxylation, hydrogenation, four steps of technical process one of aromatisation, it is length to make oleic acid Efficient Conversion into heptadecane
Alkane and aromatic hydrocarbons.
Preferably, described oleic acid and the mass ratio of catalyst are 5:1~15:1.
Preferably, described step 1) in be heated to 290~370 DEG C.In the range of reaction temperature, temperature is improved
The activity of catalyst and reaction substrate can be increased, accelerate reaction speed, reaction yield is improved
Preferably, described step 1) in the reaction time be 1~10h.
Preferably, described organic solvent can be acetone, n-hexane or dichloromethane etc..
As an improvement, described step 2) in solid-phase catalyst proceed to clean and be dried in vacuo.Solid-phase catalyst is passed through
It can be used, increased economic efficiency with circulating repetition after over cleaning and drying.
It is 5 as the mass ratio of further preferred, described oleic acid and catalyst:1~10:1.
Be used as further preferred, described step 1) in be heated to 330~370 DEG C.It is long in the heating temperature range
The yield of alkane be more than 50% and aromatic hydrocarbons yield be more than 14%.
It is 5 as the mass ratio of further preferred, described oleic acid and catalyst:1~6:1;Described step 1) in plus
Heat is warming up to 350~370 DEG C, and the reaction time is 1~2h.Under the optimum condition, the yield of long chain alkane is more than 72% and virtue
The yield of hydrocarbon is more than 19%.
Compared with the existing technology, beneficial effects of the present invention are embodied in:
(1) the not additional any hydrogen of the present invention, hydrogen supply agent or solvent, make a part of oleic acid using Pt/C catalytic action
And simultaneously further intramolecular D-A reacts aromatisation hydrogen supply for its alkene dehydrogenation of decarboxylate 17, the hydrogen of generation is rapidly saturated being left
Oleic acid into stearic acid, stearic acid decarboxylation is into heptadecane, by dehydrogenation, decarboxylation, hydrogenation, the step coupling of four technical process of aromatisation one
Close, make oleic acid Efficient Conversion for long chain alkane and aromatic hydrocarbons, the yield of long chain alkane and aromatic hydrocarbons can be respectively up to 72% and more than 19%.
(2) present invention only needs to add appropriate oleic acid and catalyst in high-temperature high-pressure reaction kettle, it is not necessary to add hydrogen
Gas, hydrogen supply agent, solvent and any other hydrogen source, realize zero hydrogen consumption, but also directly obtained hydrogenation deoxidation and Fischer-Tropsch conjunction
Into the aromatic hydrocarbons for being difficult to obtain.Solid-liquid two-phase can be to realize separation through filtering after the completion of reaction, and product separation process is simple, solid
Catalyst is easy to be recycled, and production process green, zero hydrogen consumption, energy consumption is low, simply preferably go, safe and reliable.
Brief description of the drawings
Fig. 1 is that the present invention consumes one-step method by raw material zero hydrogen of oleic acid while preparing the technique of the method for long chain alkane and aromatic hydrocarbons
General flow chart.
Embodiment
The gas chromatograph-mass spectrometer (GC-MS) (Agilent 5977A MSD) provided with three shuntings is used in the present invention while right
Long chain alkane and aromatic hydrocarbons carry out qualitative and quantitative analysis, and concrete analysis condition is as follows:Chromatographic column is Agilent HP-5MS capillarys
Tubing string (30m × 0.25mm × 0.25 μm), injector temperature:300℃;Sample introduction flow:11.383mL/min;Sample size:1μL;Three
Individual detector FID, TCD, MS detection temperature are 300 DEG C;Temperature programming:50 DEG C are kept for 4 minutes, afterwards with 25 DEG C/min's
Speed is warming up to 190 DEG C, and 200 DEG C are warming up to 5 DEG C/min speed, 250 DEG C is warming up to 15 DEG C/min speed, with 25
DEG C/min speed is warming up to 300 DEG C, last 300 DEG C are kept for 2.5 minutes.
Embodiment 1
240g oleic acid and 16g Pt/C catalyst are added in 500mL intermittent high temperatures autoclaves, 350 DEG C are warming up to instead
Answer 90min;After the completion of reaction, reaction product cooling, with acetone solution, filtering;Liquid product after acetone constant volume with using GC-MS-
FID is analyzed, and it is respectively 54% and 14%, specific technological process that calculating, which obtains C8-17 long chain alkanes and the molar yield of aromatic hydrocarbons,
As shown in Figure 1.
Embodiment 2
240g oleic acid and 24g Pt/C sieve catalysts are added in 500mL intermittent high temperatures autoclaves, 350 DEG C are warming up to
React 90min;After the completion of reaction, reaction product cooling, with acetone solution, filtering;Liquid product after acetone constant volume with using GC-
MS-FID is analyzed, and it is respectively 58% and 14% that calculating, which obtains C8-17 long chain alkanes and the molar yield of aromatic hydrocarbons,.
Embodiment 3
240g oleic acid and 32g Pt/C catalyst are added in 500mL intermittent high temperatures autoclaves, 350 DEG C are warming up to instead
Answer 90min;After the completion of reaction, reaction product cooling, with acetone solution, filtering;Liquid product after acetone constant volume with using GC-MS-
FID is analyzed, and it is respectively 61% and 14% that calculating, which obtains C8-17 long chain alkanes and the molar yield of aromatic hydrocarbons,.
Embodiment 4
240g oleic acid and 40g Pt/C catalyst are added in 500mL intermittent high temperatures autoclaves, 350 DEG C are warming up to instead
Answer 90min;After the completion of reaction, reaction product cooling, with acetone solution, filtering;Liquid product after acetone constant volume with using GC-MS-
FID is analyzed, and it is respectively 71% and 17% that calculating, which obtains C8-17 long chain alkanes and the molar yield of aromatic hydrocarbons,.
Embodiment 5
240g oleic acid and 48g Pt/C catalyst are added in 500mL intermittent high temperatures autoclaves, 350 DEG C are warming up to instead
Answer 90min;After the completion of reaction, reaction product cooling, with acetone solution, filtering;Liquid product after acetone constant volume with using GC-MS-
FID is analyzed, and it is respectively 68% and 18% that calculating, which obtains C8-17 long chain alkanes and the molar yield of aromatic hydrocarbons,.
Embodiment 6
240g oleic acid and 48g Pt/C catalyst are added in 500mL intermittent high temperatures autoclaves, 290 DEG C are warming up to instead
Answer 200min;After the completion of reaction, reaction product cooling, with acetone solution, filtering;Liquid product after acetone constant volume with using GC-MS-
FID is analyzed, and it is respectively 14% and 5% that calculating, which obtains C8-17 long chain alkanes and the molar yield of aromatic hydrocarbons,.
Embodiment 7
240g oleic acid and 48g Pt/C catalyst are added in 500mL intermittent high temperatures autoclaves, 290 DEG C are warming up to instead
Answer 560min;After the completion of reaction, reaction product cooling, with acetone solution, filtering;Liquid product after acetone constant volume with using GC-MS-
FID is analyzed, and it is respectively 32% and 9% that calculating, which obtains C8-17 long chain alkanes and the molar yield of aromatic hydrocarbons,.
Embodiment 8
240g oleic acid and 48g Pt/C catalyst are added in 500mL intermittent high temperatures autoclaves, 330 DEG C are warming up to instead
Answer 110min;After the completion of reaction, reaction product cooling, with acetone solution, filtering;Liquid product after acetone constant volume with using GC-MS-
FID is analyzed, and it is respectively 50% and 17% that calculating, which obtains C8-17 long chain alkanes and the molar yield of aromatic hydrocarbons,.
Embodiment 9
240g oleic acid and 48g Pt/C catalyst are added in 500mL intermittent high temperatures autoclaves, 330 DEG C are warming up to instead
Answer 150min;After the completion of reaction, reaction product cooling, with acetone solution, filtering;Liquid product after acetone constant volume with using GC-MS-
FID is analyzed, and it is respectively 56% and 17% that calculating, which obtains C8-17 long chain alkanes and the molar yield of aromatic hydrocarbons,.
Embodiment 10
240g oleic acid and 48g Pt/C catalyst are added in 500mL intermittent high temperatures autoclaves, 330 DEG C are warming up to instead
Answer 200min;After the completion of reaction, reaction product cooling, with acetone solution, filtering;Liquid product after acetone constant volume with using GC-MS-
FID is analyzed, and it is respectively 63% and 19% that calculating, which obtains C8-17 long chain alkanes and the molar yield of aromatic hydrocarbons,.
Embodiment 11
240g oleic acid and 48g Pt/C catalyst are added in 500mL intermittent high temperatures autoclaves, 370 DEG C are warming up to instead
Answer 80min;After the completion of reaction, reaction product cooling, with acetone solution, filtering;Liquid product after acetone constant volume with using GC-MS-
FID is analyzed, and it is respectively 72% and 19% that calculating, which obtains C8-17 long chain alkanes and the molar yield of aromatic hydrocarbons,.
Claims (5)
1. a kind of method for preparing long chain alkane and aromatic hydrocarbons simultaneously by raw material of oleic acid, it is characterised in that comprise the following steps:
1) oleic acid and catalyst, heat temperature raising reaction are added in high-temperature high-pressure reaction kettle;Described catalyst is Pt/C;It is described
Oleic acid and catalyst mass ratio be 5:1~15:1;Described is heated to 290~370 DEG C;The described reaction time is
1~10h;
2) reaction product is cooled down, organic solvent dissolving, and liquid product and solid-phase catalyst are obtained after filtering.
2. the method according to claim 1 for preparing long chain alkane and aromatic hydrocarbons simultaneously by raw material of oleic acid, it is characterised in that
Described step 2) in solid-phase catalyst proceed to clean and be dried in vacuo.
3. the method according to claim 1 for preparing long chain alkane and aromatic hydrocarbons simultaneously by raw material of oleic acid, it is characterised in that
Described oleic acid and the mass ratio of catalyst are 5:1~10:1.
4. the method according to claim 1 for preparing long chain alkane and aromatic hydrocarbons simultaneously by raw material of oleic acid, it is characterised in that
Described step 1) in be heated to 330~370 DEG C.
5. the method according to claim 1 for preparing long chain alkane and aromatic hydrocarbons simultaneously by raw material of oleic acid, it is characterised in that
Described oleic acid and the mass ratio of catalyst are 5:1~6:1;Described step 1) in be heated to 350~370 DEG C, reaction
Time is 1~2h.
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US8389782B2 (en) * | 2010-08-31 | 2013-03-05 | Chevron U.S.A. Inc. | Biofuel production through catalytic deoxygenation |
CN103614155B (en) * | 2013-09-11 | 2016-08-10 | 浙江工业大学 | A kind of algae oil produces the preparation method of HC fuel |
US20150080623A1 (en) * | 2013-09-18 | 2015-03-19 | University Of Louisville Research Foundation, Inc. | Single-Step Process for Production of Branched, Cyclic, Aromatic, and Cracked Hydrocarbons from Fatty Acids |
CN104673352B (en) * | 2015-01-30 | 2016-09-14 | 浙江大学 | A kind of method preparing long chain alkane for raw material low hydrogen consumption with waste oil |
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