CN107556152A - Photocatalysis decarboxylation method conversion higher fatty acids is the method for long chain alkane - Google Patents
Photocatalysis decarboxylation method conversion higher fatty acids is the method for long chain alkane Download PDFInfo
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Abstract
The present invention relates to the method that a kind of photocatalysis decarboxylation conversion higher fatty acids is long chain alkane, methods described includes：Under nitrogen atmosphere, solvent existence condition, higher fatty acids is subjected to the step of light-catalyzed reaction is converted into long chain alkane；The catalyst is TiO2And/or the TiO of metal surface modification2.Low power consuming, long chain alkane can be efficiently synthesized, yield may be up to 46% under conditions of without external hydrogen source using the method for the present invention.It is raw material that this method, which makes full use of higher fatty acids, room temperature is reacted in luminous energy presence, avoid needs to consume a large amount of fossil fuels in traditional industry preparation method, reaction condition without HTHP, without the catalyst for preparing complexity, it is simple to operate, without external hydrogen source, conversion ratio is higher, reaction dissolvent and product can carry out simple rotary evaporation and be separated or can be advantageous to industrialized production directly as fuel.Product long chain alkane may be used as aero oil, substitute the use of conventional fossil fuel.
Description
Technical field
The invention belongs to field of energy and chemical technology, and in particular to a kind of photocatalysis decarboxylation conversion higher fatty acids is long-chain
The method of alkane.
Background technology
In contemporary society, with human society industry, economical, science and technology fast development and energy resource consumption, energy crisis claims
To restrict a big factor of human development, find substitutability clean energy resource be referred to as top priority that current mankind faces it
One.The consumption of the conventional fossil class energy not only brings huge environmental problem, and finiteness due to its reserves and the mankind open
The quick volume increase of speed is adopted, gradually faces exhaustion.Therefore, reduce the dependence to fossil fuel, develop a kind of new, safety
, reproducible clean energy resource turned into the mankind and solved the urgent task for alleviating energy shortage and environmental pollution.
Current regenerative resource has：Solar energy, biomass energy, water energy, wind energy, tide energy etc..And wherein solar energy is made
For a kind of coverage rate is high, energy is big, the endless energy is not yet widely used.On the other hand, biomass energy is to be converted into
The exclusive source of liquid fuel, is the substitute of fossil fuel, and aero oil source can be widely used as in future.
Aviation Fuel is as a kind of special fuel, it is necessary to high calorific value and energy density.Generally it is the alkane by C8-16
Hydrocarbon, alkene and aromatic hydrocarbon composition, but aero oil can not be replaced by any one industrialized bio oil at present.The opposing party
Face, crude oil has heaviness development trend, and oil plant improves the yield of light petroleum using Deep Catalytic Cracking process at present, still
The Cetane number of the catalytic diesel oil cut obtained by this technique is relatively low.The long chain alkanes such as pentadecane are as a kind of aliphatic saturated hydrocarbon
It is the important component of diesel oil distillate, it is possible to increase the Cetane number of diesel oil.Therefore, using light-catalysed mode by advanced fat
Fat acid, which is converted into, more has the diesel hydrocarbons of value significant to alleviating energy crisis.
The method of production biomass type Aviation Fuel is mainly thermochemical method at present：The hydrogenation of vegetable oil or animal oil takes off
Water and follow-up cracking and isomerization reaction and direct decarboxylation and decarbonylation production aero oil.The former needs greatly during the course of the reaction
Amount hydrogen adds the cost of production aero oil, prevents hydrogenation deoxidation technology development and application on a large scale.The latter is current
It is decarboxylation method used to still suffer from many problems：First, their basic need external hydrogen sources or reducing agent；Second, decarboxylation technology needs 370
DEG C high temperature and 1MPa high pressure grade height energy consumption condition；Third, course of reaction complexity is not easy to realize.Therefore, more low energy consumption is found
The preparation scheme of sustainability is advantageous to the further development of diesel hydrocarbons and biomass type Aviation Fuel.
The content of the invention
The technical problem to be solved in the present invention is, in view of the shortcomings of the prior art, it is advanced to provide a kind of photocatalysis decarboxylation conversion
Aliphatic acid is the method for long chain alkane.The reproducible raw material that the present invention uses hydrolyzes gained higher aliphatic by animal and plant fat
Acid is used as reaction raw materials.Long chain alkane is produced by light-catalysed mode, the chemical reagent of required addition is few, course of reaction is simple
It is single, can utilize solar energy and biomass resource simultaneously, have low energy consumption, recyclability, sustainability, raw material total amount enrich and
The features such as widely distributed, there is larger application prospect.
The purpose of the present invention is achieved through the following technical solutions：
The invention provides the method that a kind of photocatalysis decarboxylation conversion higher fatty acids is long chain alkane, methods described includes
The step of higher fatty acids progress light-catalyzed reaction is converted into long chain alkane；The catalyst is TiO2And/or metal surface
The TiO of modification2。
Preferably, the one or more in monoacid of the higher fatty acids selected from C5~C26.More preferably palmitic acid,
Laurate, stearic acid.The long chain alkane is C4~C25 alkane.
Preferably, the temperature of the light-catalyzed reaction is 10~70 DEG C, and the reaction time is 4~28h.More preferably temperature is 20
℃.The catalytic temperature is less than 10 DEG C, can cause to need additional condensing unit refrigeration temperature control, power consumption more；Higher than 70 DEG C, then can lead
Cause a large amount of volatilizations of partial solvent.
Preferably, the TiO of the metal surface modification2For metal or metal oxide supported TiO2；The metal or gold
Category oxide includes Pt, Ni, Cu, Fe, Co, Fe2O3、Co3O4、Ni2O3、Fe3O4, CuO or Cu2At least one of O.
Preferably, the metal or metal oxide supported TiO2In, the load capacity of metal or metal oxide is 0.1
~10wt%；More preferably load capacity is 0.5~5wt%；Most preferably load capacity is 1~2wt%.
Preferably, the concentration of the higher fatty acids in a solvent is 0.005M, the catalyst higher fatty acids with
Mass concentration in the solution that solvent is formed is 0.5mg/mL.
Preferably, the TiO2It is all including P25, brookite type, Detitanium-ore-type, rutile-type, nanometer rods, nanosphere etc.
The TiO of different-shape2。
Preferably, the light source used in the light-catalyzed reaction includes at least one of ultraviolet light, visible ray；The light
The power in source is 100-300W.
Preferably, the course of reaction is not added with hydrogen source and reducing agent.
Preferably, before the light-catalyzed reaction, in addition to the step of reactant is ultrasonically treated；The supersound process
Power be 60-600W, time 30-40min.
Preferably, the solvent includes normal heptane.
Preferably, in the catalytic reaction process, reaction solution is stirred.
Preferably, after the light-catalyzed reaction terminates, solvent and long chain alkane are separated with rotary distillation method.
The present invention is a kind of method of the production long chain alkane of new high-efficient simple, and the long chain alkane of preparation is adapted as
Aero oil constituent.The shortcomings of the method overcome high temperature needed for traditional preparation methods, high pressure, external hydrogen source, can be
Reacted under normal temperature and pressure, products collection efficiency is higher, catalyst preparation is simple, solvent simple to operate, using can be straight with product
Connect rotation separated or be directly used in as fuel, and be advantageous to industrialized production.The long chain alkane that it is prepared is as bavin
Oils hydrocarbon can be used as Aviation Fuel, it can also be used to organic synthesis.
Compared with prior art, the present invention has following beneficial effect：
(1) present invention prepares long chain alkane using the hydrolysate higher fatty acids of animal and plant fat as raw material, and reaction is former
Material is with popularity and ready availability.Animal and plant fat and its hydrolysate higher fatty acids are widely present in nature, almost
The higher aliphatic acid constituents all not waited containing quantity in all animal and plant fats, without consuming fossil energy, can partly alleviate
Nowadays the energy problem that the whole world faces；
(2) method that the present invention uses can be such that the conversion of higher fatty acids carries out at normal temperatures and pressures, avoid traditional heat
The weakness of the high energy consumptions such as the HTHP of chemical method conversion higher fatty acids and severe reaction conditions.
(3) present invention makes higher aliphatic acid decarboxylation be converted into long chain alkane using light-catalysed method, can take full advantage of
Ubiquitous solar energy resources, energy consumption is low, renewable, reduces reaction cost, is with a wide range of applications.
(4) present invention need not additionally be passed through high-purity hydrogen, significantly reduce energy consumption of reaction and consumption of raw materials, and greener
Colour circle is protected, and environmental pollution is small；
(5) the required photochemical catalyst of the present invention can be prepared by the way of light deposition, and preparation process is simple, repeat profit
With, and some metals cheap and easy to get and metal oxide can be used to carry out TiO2Surface modification, reduce reaction cost.
(6) method of the invention is without adding acid, alkali.
(7) method of the invention need not add reducing agent.
(8) for the present invention to the less demanding of reaction unit, reactor is simple and easy to get, can be glass reaction kettle or stainless steel
Reactor.
(9) yield of method long chain alkane of the invention may be up to 46%, and conversion ratio is higher.
Brief description of the drawings
The detailed description made by reading with reference to the following drawings to non-limiting example, further feature of the invention,
Objects and advantages will become more apparent upon：
Fig. 1 is the general flow chart of the method for the present invention；
Fig. 2 is the GC-MS spectrograms of the product of embodiment 1；
Fig. 3 is the GC-FID spectrograms of the product of embodiment 1.
Embodiment
With reference to specific embodiment, the present invention is described in detail.Following examples will be helpful to the technology of this area
Personnel further understand the present invention, but the invention is not limited in any way.It should be pointed out that the ordinary skill to this area
For personnel, without departing from the inventive concept of the premise, some changes and improvements can also be made.These belong to the present invention
Protection domain.
Herein, the scope represented by " numerical value to another numerical value ", is that one kind avoids enumerating in the description
The summary representation of all numerical value in the scope.Therefore, the record of a certain special value scope, covers the number range
Interior any number and the relatively fractional value scope defined by any number in the number range, as bright in the description
Text writes out any number and is somebody's turn to do as compared with fractional value scope.
Embodiment 1
The present embodiment provides a kind of photochemical catalyst TiO2Lower catalyzed conversion hexadecylic acid, which is irradiated, in ultraviolet source prepares 15
The method of alkane, as shown in Figure 1.
Methods described comprises the following steps：
By hexadecylic acid n-heptane solution 30ml (hexadecylic acid concentration 0.005M) and TiO215mg loads light-catalyzed reaction kettle
In, ultrasonic 30min, reaction unit is purged with nitrogen until being nitrogen atmosphere in reactor, reactor is sealed, and is placed on
It is 20 DEG C to make reaction temperature control in 20 DEG C of cooling circulating water tanks, is placed in stirring on magnetic stirring apparatus, is shone in 150W mercury lamps
Penetrate lower reaction 4h.Product carries out qualitative (see Fig. 2) and GC-FID quantitative analyses (see Fig. 3) with GC-MS after reacting, and GC-MS is fixed
Property analysis shows, pentadecane is primary product, and GC-FID quantitative analyses show, yield is up to 9.75%.
Suitable photo catalysis reactor is used in commercial Application on demand, can be using controlling reaction temperature as 10~40 DEG C, instead
4~28h is answered, reaction atmosphere is nitrogen.By this reaction, hexadecylic acid can be largely converted into pentadecane, it is easy to operation, urge
Agent is cheap and easy to get and stability is stronger.
Wherein, reaction dissolvent normal heptane and reaction product directly can be directly separated by rotary distillation, or reaction dissolvent
Normal heptane and reaction product can use directly as fuel, so as to reduce the pollutant component for being discharged into environment to a certain extent,
So that industrial manufacturing processes are simplified.
Embodiment 2
In the present embodiment, using photochemical catalyst TiO2/ Pt (1wt%) irradiates lower catalyzed conversion 16 in ultraviolet source
Acid prepares pentadecane.
The method of the present embodiment is as follows：Using stainless steel light-catalyzed reaction kettle, by hexadecylic acid n-heptane solution 30ml (16
Acid concentration 0.005M) and TiO2/ Pt (1wt%) 15mg is fitted into light-catalyzed reaction kettle, ultrasonic 30min, is purged and reacted with nitrogen
Device is sealed reactor, and be placed in 20 DEG C of cooling circulating water tanks and make reaction until be nitrogen atmosphere in reactor
Temperature control is 20 DEG C, is placed in stirring on magnetic stirring apparatus, reacts 24h under 150W Hg lamp irradiations.Product is used after reacting
GC-MS carries out qualitative and GC-FID quantitative analyses, and GC-MS qualitative analyses show that pentadecane is primary product, and GC-FID quantitatively divides
Analysis shows that yield is up to 42.05%.
Suitable photo catalysis reactor is used in commercial Application on demand, can be using controlling reaction temperature as 10~40 DEG C, instead
4~28h is answered, reaction atmosphere is nitrogen.By this reaction, hexadecylic acid can be largely converted into pentadecane, it is easy to operation, urge
Agent is cheap and easy to get and stability is stronger.
Wherein, reaction dissolvent normal heptane and reaction product directly can be directly separated by rotary distillation, or reaction dissolvent
Normal heptane and reaction product can use directly as fuel, so as to reduce the pollutant component for being discharged into environment to a certain extent,
So that industrial manufacturing processes are simplified.
Embodiment 3
In the present embodiment, using photochemical catalyst TiO2/Co3O4(1wt%) irradiates lower catalyzed conversion ten in ultraviolet source
Six acid prepare pentadecane.
The method of the present embodiment is as follows：Using stainless steel light-catalyzed reaction kettle, by hexadecylic acid n-heptane solution 30ml (16
Acid concentration 0.005M) and TiO2/Co3O4(1wt%) 15mg is fitted into light-catalyzed reaction kettle, ultrasonic 30min, is purged with nitrogen anti-
Answer device until reactor in be nitrogen atmosphere, reactor is sealed, and be placed in 20 DEG C of cooling circulating water tanks make instead
It is 20 DEG C to answer temperature control, is placed in stirring on magnetic stirring apparatus, reacts 4h under 150W Hg lamp irradiations.Product is used after reacting
GC-MS carries out qualitative and GC-FID quantitative analyses, and GC-MS qualitative analyses show that pentadecane is primary product, and GC-FID quantitatively divides
Analysis shows that yield is up to 6.93%.
Suitable photo catalysis reactor is used in commercial Application on demand, can be using controlling reaction temperature as 10~40 DEG C, instead
4~28h is answered, reaction atmosphere is nitrogen.By this reaction, hexadecylic acid can be converted into pentadecane, easy to operation, catalyst
Cheap and easy to get and stability is stronger.
Wherein, reaction dissolvent normal heptane and reaction product directly can be directly separated by rotary distillation, or reaction dissolvent
Normal heptane and reaction product can use directly as fuel, so as to reduce the pollutant component for being discharged into environment to a certain extent,
So that industrial manufacturing processes are simplified.
Embodiment 4
In the present embodiment, using photochemical catalyst TiO2/ Cu (1wt%) irradiates lower catalyzed conversion hexadecylic acid in full radiant
Prepare pentadecane.
The method of the present embodiment is as follows：Using stainless steel light-catalyzed reaction kettle, by hexadecylic acid n-heptane solution 30ml (16
Acid concentration 0.005M) and TiO2/ Cu (1wt%) 15mg is fitted into light-catalyzed reaction kettle, ultrasonic 30min, is purged and reacted with nitrogen
Device is sealed reactor, and be placed in 20 DEG C of cooling circulating water tanks and make reaction until be nitrogen atmosphere in reactor
Temperature control is 20 DEG C, is placed in stirring on magnetic stirring apparatus, reacts 4h under xenon lamp irradiation.By product GC-MS after reaction
Qualitative and GC-FID quantitative analyses are carried out, GC-MS qualitative analyses show, pentadecane is primary product, GC-FID quantitative analysis tables
Bright, yield is up to 25.57%.
Suitable photo catalysis reactor is used in commercial Application on demand, can be using controlling reaction temperature as 10~40 DEG C, instead
4~28h is answered, reaction atmosphere is nitrogen.By this reaction, hexadecylic acid can be largely converted into pentadecane, easy to operation, Cu
The TiO2 catalyst cost of surface modification is relatively low compared with other noble metals.
Wherein, reaction dissolvent normal heptane and reaction product directly can be directly separated by rotary distillation, or reaction dissolvent
Normal heptane and reaction product can use directly as fuel, so as to reduce the pollutant component for being discharged into environment to a certain extent,
So that industrial manufacturing processes are simplified.
Embodiment 5
In the present embodiment, photocatalysis decarboxylation under ultraviolet light is used to convert stearic acid as heptadecane.
The method of the present embodiment is as follows：Using stainless steel light-catalyzed reaction kettle, by stearic acid n-heptane solution 30ml (18
Acid concentration 0.005M) and TiO2/ Pt (1wt%) 15mg is fitted into light-catalyzed reaction kettle, ultrasonic 30min, is purged and reacted with nitrogen
Device is sealed reactor, and be placed in 20 DEG C of cooling circulating water tanks and make reaction until be nitrogen atmosphere in reactor
Temperature control is 20 DEG C, is placed in stirring on magnetic stirring apparatus, reacts 24h under 150W Hg lamp irradiations.Product is used after reacting
GC-MS carries out qualitative and GC-FID quantitative analyses, and GC-MS qualitative analyses show that heptadecane is primary product, and GC-FID quantitatively divides
Analysis shows that yield is up to 46.39%.
Suitable photo catalysis reactor is used in commercial Application on demand, can be using controlling reaction temperature as 10~40 DEG C, instead
4~28h is answered, reaction atmosphere is nitrogen.By this reaction, stearic acid can be largely converted into heptadecane, it is easy to operation, urge
Agent is cheap and easy to get and stability is stronger.
Wherein, reaction dissolvent normal heptane and reaction product directly can be directly separated by rotary distillation, or reaction dissolvent
Normal heptane and reaction product can use directly as fuel, so as to reduce the pollutant component for being discharged into environment to a certain extent,
So that industrial manufacturing processes are simplified.
Embodiment 6
In the present embodiment, photocatalysis decarboxylation under ultraviolet light is used to convert lauric acid/dodecanoic acid as hendecane.
The method of the present embodiment is as follows：Using stainless steel light-catalyzed reaction kettle, by lauric acid/dodecanoic acid n-heptane solution 30ml (12
Acid concentration 0.005M) and TiO2/ Pt (1wt%) 15mg is fitted into light-catalyzed reaction kettle, ultrasonic 30min, is purged and reacted with nitrogen
Device is sealed reactor, and be placed in 20 DEG C of cooling circulating water tanks and make reaction until be nitrogen atmosphere in reactor
Temperature control is 20 DEG C, is placed in stirring on magnetic stirring apparatus, reacts 24h under 150W Hg lamp irradiations.Product is used after reacting
GC-MS carries out qualitative and GC-FID quantitative analyses, and GC-MS qualitative analyses show that hendecane is primary product, and GC-FID quantitatively divides
Analysis shows that yield is up to 43.09%.
Suitable photo catalysis reactor is used in commercial Application on demand, can be using controlling reaction temperature as 10~40 DEG C, instead
4~28h is answered, reaction atmosphere is nitrogen.By this reaction, lauric acid/dodecanoic acid can be largely converted into hendecane, it is easy to operation, urge
Agent is cheap and easy to get and stability is stronger.
Wherein, reaction dissolvent normal heptane and reaction product directly can be directly separated by rotary distillation, or reaction dissolvent
Normal heptane and reaction product can use directly as fuel, so as to reduce the pollutant component for being discharged into environment to a certain extent,
So that industrial manufacturing processes are simplified.
Embodiment 7
In the present embodiment, photocatalysis decarboxylation is used to convert hexadecylic acid as pentadecane.Its specific preparation process and embodiment 1
It is essentially identical, it the difference is that only：The catalyst that the present embodiment uses is TiO2/ Ni (5wt%), light source are xenon source.
Product carries out qualitative and GC-FID quantitative analyses with GC-MS after reacting, and GC-MS qualitative analyses show, pentadecane is main production
Thing, GC-FID quantitative analyses show that yield is up to 7.13%.
Embodiment 8
In the present embodiment, photocatalysis decarboxylation is used to convert hexadecylic acid as pentadecane.Its specific preparation process and embodiment 1
It is essentially identical, it the difference is that only：The catalyst that the present embodiment uses is TiO2/ Cu (0.5wt%), light source are xenon lamp
Source.Product carries out qualitative and GC-FID quantitative analyses with GC-MS after reacting, and GC-MS qualitative analyses show that pentadecane is main
Product, GC-FID quantitative analyses show that yield is up to 22.05%.
The specific embodiment of the present invention is described above.It is to be appreciated that the invention is not limited in above-mentioned
Particular implementation, those skilled in the art can make a variety of changes or change within the scope of the claims, this not shadow
Ring the substantive content of the present invention.In the case where not conflicting, the feature in embodiments herein and embodiment can any phase
Mutually combination.
Claims (10)
1. a kind of photocatalysis decarboxylation conversion higher fatty acids is the method for long chain alkane, it is characterised in that methods described includes：
Under nitrogen atmosphere, solvent existence condition, higher fatty acids is subjected to the step of light-catalyzed reaction is converted into long chain alkane；It is described to urge
Agent is TiO2And/or the TiO of metal surface modification2。
2. photocatalysis decarboxylation conversion higher fatty acids according to claim 1 is the method for long chain alkane, it is characterised in that
One or more in monoacid of the higher fatty acids selected from C5~C26；The long chain alkane is C4~C25 alkane.
3. photocatalysis decarboxylation conversion higher fatty acids according to claim 1 is the method for long chain alkane, it is characterised in that
The temperature of the light-catalyzed reaction is 10~70 DEG C, and the reaction time is 4~28h.
4. photocatalysis decarboxylation conversion higher fatty acids according to claim 1 is the method for long chain alkane, it is characterised in that
The TiO of the metal surface modification2For metal or metal oxide supported TiO2；The metal or metal oxide include Pt,
Ni、Cu、Fe、Co、Fe2O3、Co3O4、Ni2O3、Fe3O4, CuO or Cu2At least one of O.
5. photocatalysis decarboxylation conversion higher fatty acids according to claim 4 is the method for long chain alkane, it is characterised in that
The metal or metal oxide supported TiO2In, the load capacity of metal or metal oxide is 0.1~10wt%.
6. the photocatalysis decarboxylation conversion higher fatty acids according to claim 1,4 or 5 any one is the method for long chain alkane,
Characterized in that, the concentration of the higher fatty acids in a solvent is 0.005M, the catalyst is in higher fatty acids and solvent
Mass concentration in the solution of formation is 0.5mg/mL.
7. photocatalysis decarboxylation conversion higher fatty acids according to claim 1 is the method for long chain alkane, it is characterised in that
The light source used in the light-catalyzed reaction includes at least one of ultraviolet light, visible ray；The power of the light source is 100-
300W。
8. photocatalysis decarboxylation conversion higher fatty acids according to claim 1 is the method for long chain alkane, it is characterised in that
The course of reaction is not added with hydrogen source and reducing agent.
9. photocatalysis decarboxylation conversion higher fatty acids according to claim 1 is the method for long chain alkane, it is characterised in that
Before the light-catalyzed reaction, in addition to the step of reactant is ultrasonically treated；The power of the supersound process is 60-
600W, time 30-40min.
10. photocatalysis decarboxylation conversion higher fatty acids according to claim 1 is the method for long chain alkane, its feature exists
In the solvent includes normal heptane.
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| CN112707602A (en) * | 2020-12-31 | 2021-04-27 | 西安交通大学 | Method for treating volatile fatty acid in wastewater by coupling of optical enzyme |
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| CN109796299A (en) * | 2019-02-21 | 2019-05-24 | 浙江诺诚技术发展有限公司 | A kind of method that environmentally protective visible light catalytic prepares hexafluoro-isobutene |
| CN109796299B (en) * | 2019-02-21 | 2022-02-08 | 浙江诺诚技术发展有限公司 | Method for preparing hexafluoroisobutylene through green and environment-friendly visible light catalysis |
| CN112707602A (en) * | 2020-12-31 | 2021-04-27 | 西安交通大学 | Method for treating volatile fatty acid in wastewater by coupling of optical enzyme |
| CN112707602B (en) * | 2020-12-31 | 2022-04-22 | 西安交通大学 | Method for treating volatile fatty acid in wastewater by coupling of optical enzyme |
| CN113307713A (en) * | 2021-06-29 | 2021-08-27 | 南京工程学院 | Method for preparing long-chain alkane by micro-channel-photocatalysis coupling |
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Application publication date: 20180109 |