CN106318433B - A kind of hydrotreating method of animal and plant fat - Google Patents
A kind of hydrotreating method of animal and plant fat Download PDFInfo
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- CN106318433B CN106318433B CN201510342587.9A CN201510342587A CN106318433B CN 106318433 B CN106318433 B CN 106318433B CN 201510342587 A CN201510342587 A CN 201510342587A CN 106318433 B CN106318433 B CN 106318433B
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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
Abstract
A kind of hydrotreating method of animal and plant fat, after vegetable oil and/or animal fat and hydrogen and regulation and control gas mixing, it is contacted with the hydrotreating catalyst of sulphided state and carries out that hydrotreating reaction product is obtained by the reaction, hydrotreating reaction product passes through gas-liquid separation, liquid phase hydrocarbon material flow, gaseous stream and water are obtained, Partial Liquid Phase hydrocarbon material flow is recycled to hydrotreating reactor entrance.Using method provided by the invention, CO and CO in reaction product is effectively reduced2The content of product, while improving the yield of liquid hydrocarbon product.
Description
Technical field
The present invention relates to one kind in presence of hydrogen, the processing method of animal and plant fat.
Background technology
As traditional fossil energy supply is becoming tight, the pressure of carbon dioxide discharge-reduction increasingly increases, and development is renewable, cleans
Alternative energy source have become global common recognition.Since bioenergy has recyclability, green, especially it is taken seriously in recent years,
It is considered as most one of the desirable route for solving global energy crisis.
It is continuously increased with the demand of jet fuel, the technology of jet fuel is prepared increasingly by people from renewable raw materials
Attention.These renewable raw materials include but do not limit in this way, such as：Vegetable oil (soybean oil, rapeseed oil, palm oil, leprosy
Tree oil, Chinese tallow), animal tallow (lard, butter, fish oil), acidification oil, various aliphatic acid and acidification oil etc..
Have currently, research is more, using vegetable oil and/or animal fat, aliphatic acid is prepared by ester exchange reaction
Methyl esters.Fatty acid methyl ester is a kind of clean regenerative resource, is the substitute products of good petroleum diesel, is current use most
More biodiesel oil products.
But the prior art does not provide a kind of method that can regulate and control different carbon number n-alkane ratios in hydrogenation products.
Invention content
The purpose of the present invention is on the basis of existing technology, providing a kind of hydrotreating method of animal and plant fat, it is
A kind of method that can regulate and control different carbon number n-alkane ratios in hydrogenation products.
A kind of hydrotreating method of animal and plant fat provided by the invention, including：
In hydrotreating reactor, in the presence of hydrogen and regulation and control gas, vegetable oil and/or animal fat and sulphided state
Hydrotreating catalyst contacts, and is reacted at hydrotreating reaction conditions, obtains hydrotreating reaction product, the tune
Control gas is CO and/or CO2, in the reaction zone, hydrogen partial pressure is 1.0MPa~20.0MPa；Hydrogen partial pressure and regulation and control gas
Intrinsic standoff ratio be 2~300, hydrotreating reaction product pass through gas-liquid separation, obtain liquid phase hydrocarbon material flow, gaseous stream and
Water, the liquid phase hydrocarbon material flow are C8-C24N-alkane, wherein even carbon n-alkane are more than odd number carbon n-alkane, part
Liquid phase hydrocarbon material flow is sent as recycle oil to hydrotreating reactor entrance.
In method provided by the invention, the vegetable oil and/or animal fat contain glyceride and free fat to be any
The raw material and vegetable oil and/or animal fat of fat acid pass through fatty acid methyl ester or fatty-acid ethyl ester prepared by ester exchange method.
The glyceride includes triglycerides, diglyceride and monoglyceride.Including but not limited to, soybean oil, rapeseed oil, cottonseed
Oil, corn oil, rice bran oil, sunflower oil, peanut oil, castor oil, sesame oil, Fructus Zanthoxyli oil, tea oil, coconut oil, olive oil, Huang
Even one or more of wood oil, palm oil, tung oil, curcas oil, turpentine oil, Chinese tallow and algae oil.The vegetable and animals oils
Fat further includes waste oil from restaurant.The vegetable oil and animal fat can be mixed with arbitrary proportion.In addition, according to the present invention
Vegetable and animals oils fat raw material also includes that animal and plant fat passes through fatty acid methyl ester or fatty-acid ethyl ester prepared by ester exchange method.
By taking palm oil hydrogenation process as an example, palm oil contains a variety of reactions based on triglycerides, wherein including mainly
Hydrogen saturated reaction and hydrogenation deoxidation is added to react.Shown in palm oil hydrogenation reaction approach figure below：
The first step of reaction is double bond plus hydrogen saturation in unsaturated fatty acid, and hydrogenation deoxidation reaction then occurs.Add hydrogen
There are mainly three types of approach for deoxidation：Hydrogenation deoxidation reacts, and product is mainly propane, water and C16、C18Equal even numbers alkane；Add hydrogen de-
Carbonyl reaction, product are mainly propane, water, carbon monoxide and C15、C17Equal odd numbers alkane；Add hydrogen decarboxylation to react, generates production
Object is propane, carbon dioxide and C15、C17Equal odd numbers alkane.
Palm oil adds hydrogen primary product to be the C of positive structure15、C16、C17、C18, by-product propane, water, carbon monoxide, titanium dioxide
Carbon.Inventor carries out further investigation discovery, with the difference of reaction condition, in the hydrogenation products obtained on same catalyst, and m
(C15+C17)/m(C16+C18) numerical value can change, wherein m (C15+C17) refer to C15N-alkane and C17N-alkane
Quality sum, m (C16+C18) refer to C16N-alkane and C18The quality sum of n-alkane.
The present invention regulates and controls the partial pressure of gas by increasing during the reaction, and the size of adjustment regulation and control partial pressure is reduced
The generation of odd number normal alkane makes reaction be carried out to deoxygenation, the n-alkane of voluminous even number, and the regulation and control gas is CO
And/or CO2.The method provided through the invention effectively reduces the decarburizing reaction of raw material, increases deoxygenation, to subtract
CO and CO in reaction product is lacked2Carbon atom has been retained in liquid phase hydrocarbon product, has accordingly increased liquid phase by product assay
The yield of hydrocarbon product.By taking palm oil raw material as an example, by regulation and control, m (C can be controlled15+C17)/m(C16+C18) ratio be 1：
1~1：5.
After vegetable oil and/or animal fat are sufficiently mixed with hydrogen and regulation and control gas, enter back into hydrotreating reactor and
The hydrotreating catalyst of sulphided state contacts, and in hydrotreating reactor, hydrogen partial pressure is 3.0MPa~15.0MPa；Hydrogen
Partial pressure is 5~250 with regulation and control partial pressure ratio.
In order to ensure that hydrotreating catalyst is constantly in the state of sulphided state, the vegetable oil and/or animal fat
It is mixed into vulcanizing agent before into hydrotreating reactor, on the basis of vegetable oil and/or animal fat, sulphur concentration is 0.01 weight %
~0.5 weight %.The vulcanizing agent is selected from H2S、CS2, dimethyl disulfide, Dimethyl sulfide, in n-butyl sulfide and thiophene
It is one or more of.
The hydrotreating reaction condition is：Reaction pressure 1.0MPa~20.0MPa, 200 DEG C~400 DEG C of reaction temperature,
Volume space velocity 0.5h-1~5.0h-1,300~1500Nm of hydrogen to oil volume ratio3/m3, the volume ratio of recycle oil and feedstock oil is 3：1~
1:5.It is preferred that the hydrotreating reaction condition is：Reaction pressure reaction pressure 3.0MPa~15.0MPa, 220 DEG C of reaction temperature
~360 DEG C, volume space velocity 0.8h-1~3.0h-1, 400~1200Nm of hydrogen to oil volume ratio3/m3, the volume ratio of recycle oil and feedstock oil
It is 2：1~1:3.
The hydrotreating catalyst be containing heat-resistant inorganic oxide carrier and load on this carrier plus hydrogen live
Property component, active component is selected from the combination of one or more of one or more of VI B races metal and VIII race's metal.
The one kind or more of the carrier in aluminium oxide, silica, magnesia, titanium oxide, zirconium oxide and molecular sieve
The mixture of kind；The active component is one or more of cobalt, nickel, molybdenum, tungsten；On the basis of the weight of catalyst, with
The content of oxide meter, molybdenum and/or tungsten is 5~40 weight %, and the content of cobalt and/or nickel is 1~10 weight %.
The hydrotreating catalyst is with or without auxiliary agent phosphorus and with or without organic additive, organic addition
Object is selected from one or more of oxygen-containing organic compound or organic compounds containing nitrogen.Preferred oxygen-containing organic compound, which is selected from, to be had
One or more of machine alcohol and organic acid；Preferred organic compounds containing nitrogen is selected from one or more of organic amine.For example,
Oxygen-containing organic compound can enumerate ethylene glycol, glycerine, polyethylene glycol (molecular weight 200-1500), diethylene glycol, fourth two
In alcohol, acetic acid, maleic acid, oxalic acid, aminotriacetic acid, 1,2- cyclohexanediamine tetraacetic acids, citric acid, tartaric acid, malic acid
One or more, organic compounds containing nitrogen can enumerate ethylenediamine, EDTA and its ammonium salt.
They can be commercially available commodity or be prepared using arbitrary existing method.For example, a kind of disclosed in CN1085934A
Hydrogenation catalyst, the catalyst contain by magnesia, nickel oxide, tungsten oxide and aluminium oxide, consisting of：Magnesia 0.1~1.9
Weight %, 2.5~6 weight % of nickel oxide, 24~34 weight % of tungsten oxide and remainder alumina.
It is a kind of using aluminium oxide as the hydrogenation catalyst of containing phosphor of carrier disclosed in CN1872960A, the group after catalyst roasting
As 1~10 weight % of nickel oxide, the sum of molybdenum oxide and tungsten oxide are more than 10 to 50 weight %, phosphorous oxide 1~9 weight %, remaining
Amount is aluminium oxide, wherein in terms of oxide, the molar ratio of tungsten and molybdenum is more than 2.6 to 30.
CN1840618A is a kind of using silica-alumina as the hydrogenation catalyst of carrier and its preparation, catalyst roasting
Group afterwards becomes：1~10 weight % of nickel oxide, the sum of molybdenum oxide and tungsten oxide are more than 10 to 50 weight %, and surplus is carrier.
In catalyst disclosed in CN1872960A and CN1840618A, preferably also contain organic additive, wherein described
The molar ratio of organic matter and the sum of hydrogenation active metal component in terms of oxide is 0.03~2 preferably 0.08~1.5.
These catalyst can be used as the hydrotreating catalyst and be used for the present invention.About the more detailed of above-mentioned catalyst
Preparation method, it is on the books in the above documents, here together using they as the content of present invention a part quote.
Energy hydrotreating renewable raw materials of the invention produce biodiesel, and the present invention by increasing regulation and control during the reaction
Partial pressure, the size of adjustment regulation and control partial pressure, makes reaction be carried out to deoxygenation, the n-alkane of voluminous even number.Pass through
Method provided by the invention effectively reduces the decarburizing reaction of raw material, increases deoxygenation, to reduce reaction product
Middle CO and CO2Product assay, carbon atom has been retained in liquid hydrocarbon product, accordingly increases the receipts of liquid hydrocarbon product
Rate.
Description of the drawings
Attached drawing is a kind of hydrotreating method flow simplified schematic diagram of animal and plant fat provided by the invention.
Specific implementation mode
The method of the present invention is further explained below in conjunction with the accompanying drawings, but not thereby limiting the invention.
After raw oil material from pipeline 1 is sufficiently mixed with the hydrogen from pipeline 2 and the regulation and control gas from pipeline 3,
It into hydrotreating reactor, contacts and is reacted with hydrotreating catalyst, reaction product enters high pressure point through pipeline 6
Gas-liquid separation is carried out from device 50, is divided into two-way after the extraction of hydrotreating reaction liquid phase hydro carbons stream passes via line 4 of gained, makees all the way
Hydrotreating reactor entrance is returned to through pipeline 8 for recycle oil, another way is through 9 carrying device of pipeline.High-pressure separator 50 detaches
The gaseous stream of gained enters after circulating hydrogen compressor 60 pressurizeed, and hydrotreating reactor entrance is sent into through pipeline 7.High pressure
The separating obtained waste water of separator 50 is through 5 discharger of pipeline.
Below by embodiment, the invention will be further described, but not thereby limiting the invention.
In embodiment and comparative example：
Hydrotreating catalyst is prepared according to CN1085934A published methods, consisting of：1 weight % of magnesia, oxidation
4 weight % of nickel, 29 weight % of tungsten oxide and remainder alumina.
1 raw material oil nature of table
| Project | Palm oil | Waste cooking oil |
| Density (20 DEG C)/(g/cm3) | 0.9151 | 0.9173 |
| Bromine valency, gBr/100mL | 26.1 | 17.2 |
| 40 DEG C of viscosity/(mm2/s) | 40.84 | 33.41 |
| Solidification point/DEG C | 10 | 10 |
| Total acid number/(mgKOH/g) | 0.0505 | 11.2 |
| C content/% | 76.66 | 76.00 |
| H content/% | 11.95 | 11.89 |
| O content/% | 11.39 | 11.76 |
| Cl contents/% | 3.8 | 11 |
| S contents/(μ g/g) | <2.0 | 18 |
| D-2887 boiling ranges/DEG C | ||
| 10% | 524 | 571 |
| 50% | 542 | 611 |
| 70% | 552 | 614 |
| 90% | 567 | 620 |
| 99% | 575 | 657 |
Embodiment 1
Feedstock oil uses palm oil, and property is shown in Table 1, and using method provided by the invention, palm oil and hydrogen and CO are abundant
It after mixing, is reacted into hydrotreating reactor with the hydrotreating catalyst of sulphided state, obtains hydrotreating reaction life
At object.Wherein, the palm oil is mixed into dimethyl disulfide before entering hydrotreating reactor, on the basis of palm oil, sulphur
A concentration of 0.1 weight %.After gas-liquid separation, liquid phase hydro carbons stream portions are recycled back to be added at hydrogen hydrotreating reaction product
Manage reactor inlet, remainder ejector.
Hydrogenation conditions are shown in Table 2, and product distribution and property are shown in Table 3.
Embodiment 2
Feedstock oil uses certain waste cooking oil, and property is shown in Table 1, using method provided by the invention, waste cooking oil and hydrogen
And CO2It after being sufficiently mixed, is reacted into hydrotreating reactor with the hydrotreating catalyst of sulphided state, obtains adding at hydrogen
Manage reaction product.Wherein, the waste cooking oil is mixed into dimethyl disulfide before entering hydrotreating reactor, useless with food and drink
On the basis of oil, sulphur concentration is 0.2 weight %.Hydrotreating reaction product after gas-liquid separation, liquid phase hydro carbons stream portions
It is recycled back to hydrotreating reactor entrance, remainder ejector.Hydrogenation conditions are shown in Table 2, and product distribution and property are shown in
Table 3.
Embodiment 3
Feedstock oil uses palm oil, property to be shown in Table 1, using method provided by the invention, palm oil and hydrogen and regulation and control gas
After body is sufficiently mixed, is reacted into hydrotreating reactor with the hydrotreating catalyst of sulphided state, obtain hydrotreating
Reaction product.Wherein, regulation and control gas is CO and CO2Mixed gas, CO and CO2Volume ratio 50：50, the palm oil
It is mixed into dimethyl disulfide before into hydrotreating reactor, on the basis of palm oil, sulphur concentration is 0.1 weight %.Add at hydrogen
Manage reaction product after gas-liquid separation, liquid phase hydro carbons stream portions are recycled back to hydrotreating reactor entrance, remainder
Ejector.
Hydrogenation conditions are shown in Table 2, and product distribution and property are shown in Table 3.
Comparative example 1
For feedstock oil with embodiment 1, technological process is same as Example 1, and difference lies in be free of in hydrotreating reactor
There is CO, other reaction conditions are the same as embodiment 1.
Reaction condition and product distribution are shown in Table 2 and table 3 respectively.
Comparative example 2
For feedstock oil with embodiment 2, technological process is same as Example 2, difference lies in hydrotreating reaction area not
Contain CO2, other reaction conditions are the same as embodiment 2.
Reaction condition and product distribution are shown in Table 2 and table 3 respectively.
2 hydrogenation conditions of table
3 hydrotreating product property of table
From above-described embodiment in terms of comparative example, method provided by the invention, in the reaction atmosphere in hydrotreating reaction area
Increase CO and/or CO2Regulation and control gas, make hydrogenation reaction to deoxidation direction carry out, by-product is with H2Based on O, liquid hydrocarbon product
Yield 4.1 percentage points and 7.5 percentage points have been respectively increased.
Claims (9)
1. a kind of hydrotreating method of animal and plant fat, which is characterized in that in hydrotreating reactor, in hydrogen and regulation and control
In the presence of gas, vegetable oil and/or animal fat are contacted with sulphided state hydrotreating catalyst, at hydrotreating reaction conditions
It is reacted, obtains hydrotreating reaction product, the regulation and control gas is CO and/or CO2, in hydrotreating reactor,
Hydrogen partial pressure is 1.0MPa~20.0MPa；The intrinsic standoff ratio of hydrogen partial pressure and regulation and control gas is 2~300, and hydrotreating reaction generates
Object passes through gas-liquid separation, obtains liquid phase hydrocarbon material flow, gaseous stream and water, and the liquid phase hydrocarbon material flow is C8-C24N-alkane,
Wherein even carbon n-alkane is more than odd number carbon n-alkane, and Partial Liquid Phase hydrocarbon material flow send anti-to hydrotreating as recycle oil
Answer device entrance, the hydrotreating catalyst be containing heat-resistant inorganic oxide carrier and load on this carrier plus hydrogen live
Property component, active component is selected from the combination of one or more of one or more of VI B races metal and VIII race's metal.
2. according to method of claim 1, which is characterized in that vegetable oil and/or animal fat and hydrogen and regulation and control gas are abundant
It after mixing, enters back into hydrotreating reactor and is contacted with hydrotreating catalyst, in hydrotreating reactor, hydrogen partial pressure is
3.0MPa~15.0MPa；Hydrogen partial pressure is 5~250 with regulation and control partial pressure ratio.
3. according to method of claim 1, which is characterized in that it is anti-that the vegetable oil and/or animal fat enters hydrotreating
It is mixed into vulcanizing agent before answering device, on the basis of vegetable oil and/or animal fat, sulphur concentration is 0.01 weight of weight %~0.5 %.
4. according to the method for claim 3, which is characterized in that the vulcanizing agent is selected from H2S、CS2, dimethyl disulfide, methyl
One or more of thioether, n-butyl sulfide and thiophene.
5. according to method of claim 1, which is characterized in that the hydrotreating reaction condition is：Hydrogen partial pressure 1.0MPa~
20.0MPa, 200 DEG C~400 DEG C of reaction temperature, volume space velocity 0.5h-1~5.0h-1, 300~1500Nm of hydrogen to oil volume ratio3/m3,
The volume ratio of recycle oil and feedstock oil is 3:1~1:5.
6. according to method of claim 1, which is characterized in that the hydrotreating reaction condition is：Hydrogen partial pressure 3.0MPa~
15.0MPa, 220 DEG C~360 DEG C of reaction temperature, volume space velocity 0.8h-1~3.0h-1, 400~1200Nm of hydrogen to oil volume ratio3/m3,
The volume ratio of recycle oil and feedstock oil is 2:1~1:3.
7. according to method of claim 1, which is characterized in that the carrier is selected from aluminium oxide, silica, magnesia, oxidation
One or more mixtures in titanium, zirconium oxide and molecular sieve；The active component be cobalt, nickel, molybdenum, one kind in tungsten or
It is several；On the basis of the weight of catalyst, in terms of oxide, the content of molybdenum and/or tungsten is 5~40 weight %, cobalt and/or nickel
Content is 1~10 weight %.
8. according to the method for claim 1 or 7, which is characterized in that the hydrotreating catalyst with or without auxiliary agent phosphorus with
And with or without organic additive, the one kind of the organic additive in oxygen-containing organic compound or organic compounds containing nitrogen
Or it is several.
9. according to the method for claim 1, which is characterized in that the vegetable oil and/or animal fat be it is any containing
The raw material and vegetable oil and/or animal fat of glyceride and free fatty pass through fatty acid methyl prepared by ester exchange method
Ester or fatty-acid ethyl ester.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109294623B (en) * | 2017-07-25 | 2021-01-08 | 中国石油化工股份有限公司 | Hydrogenation method for preparing diesel oil fraction from oil raw material |
| CN108624358A (en) * | 2018-05-25 | 2018-10-09 | 未名生物能源有限公司 | A method of preparing biodiesel blending component by raw material of acidification oil |
| CN109126813A (en) * | 2018-09-17 | 2019-01-04 | 龙岩卓越新能源股份有限公司 | Utilize the method for waste animal and plant fat production atoleine |
| CN110423631A (en) * | 2019-01-24 | 2019-11-08 | 易高环保能源研究院有限公司 | A kind of method that animal and plant fat direct hydrogenation prepares high cetane number diesel oil |
| CN111925824A (en) * | 2020-08-07 | 2020-11-13 | 易高生物化工科技(张家港)有限公司 | Method for preparing renewable alkane by hydrogenating waste animal and vegetable oil |
| CN111909720A (en) * | 2020-08-08 | 2020-11-10 | 易高生物化工科技(张家港)有限公司 | Hydrotreatment method for waste animal and vegetable oil |
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| CN103154201A (en) * | 2010-08-31 | 2013-06-12 | 杰富意钢铁株式会社 | Method for decomposing organic substance into lower molecules, and method for utilizing exhaust gas generated by metallurgical furnace |
| CN104136580A (en) * | 2012-02-27 | 2014-11-05 | 杰富意钢铁株式会社 | Method for lowering molecular weight of organic substance |
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| WO2011031435A2 (en) * | 2009-08-28 | 2011-03-17 | Exxonmobil Research And Engineering Company | Reducing hydrogen consumption in hydrotreating of biocomponent feeds |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103154201A (en) * | 2010-08-31 | 2013-06-12 | 杰富意钢铁株式会社 | Method for decomposing organic substance into lower molecules, and method for utilizing exhaust gas generated by metallurgical furnace |
| CN104136580A (en) * | 2012-02-27 | 2014-11-05 | 杰富意钢铁株式会社 | Method for lowering molecular weight of organic substance |
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