CN106542948B - The method for preparing pentadecylcyclohexane and pentadecyl benzene as raw material using anacardol - Google Patents
The method for preparing pentadecylcyclohexane and pentadecyl benzene as raw material using anacardol Download PDFInfo
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- CN106542948B CN106542948B CN201610903813.0A CN201610903813A CN106542948B CN 106542948 B CN106542948 B CN 106542948B CN 201610903813 A CN201610903813 A CN 201610903813A CN 106542948 B CN106542948 B CN 106542948B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
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- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
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Abstract
The present invention relates to a kind of methods for preparing pentadecylcyclohexane and pentadecyl benzene as raw material using anacardol.This method comprises: Pt/Al will be equipped with2O3The fixed bed reactors of granule type solid catalyst carry out nitrogen treatment；Hydrogen is passed through into the fixed bed reactors equipped with catalyst through nitrogen treatment；Anacardol is sent into the hydrogen stream that hydrogen is formed, the gas-liquid mixture stream formed after mixing enters the fixed bed reactors equipped with catalyst, and pentadecylcyclohexane and pentadecyl benzene are generated after reaction.The catalyst Pt of granule type solid used in the present invention/Al2O3With excellent catalytic activity, catalytic stability and anti-carbon deposition ability, and catalyst is renewable and reuses；By-product and the three wastes are less in the method for the present invention production process, and target product selectivity is higher；The method of the present invention product yield is relatively high；Production technology of the invention and easy to operate, only needs single step reaction, is particularly conducive to industrialized production.
Description
Technical field
The invention belongs to Industrial Catalysis fields, and in particular to it is a kind of using anacardol as raw material prepare pentadecylcyclohexane and
The method of pentadecyl benzene.Pentadecane basic ring is prepared as raw material on fixed bed hydrogenation reactor using anacardol more particularly to one kind
The method of hexane and pentadecyl benzene.
Background technique
Pentadecylcyclohexane is a kind of important Organic Chemicals intermediate, also can be used as liquid alkane fuel.Mesh
The production of preceding pentadecylcyclohexane mainly passes through the method for organic synthesis.
Pentadecyl benzene is the important component of linear alkyl benzene (or linear alkylbenzene (LAB), LAB), is also important virtue
Fragrant race's Organic Chemicals, for producing surfactant and synthetic detergent, LAB is mainly for the manufacture of LINER ALKYL BENZENE SULPHONIC ACID SOFT 96
Salt (LAS) synthetic detergent, LAS have become the most important raw material of household and industrial detergent.
The production of pentadecyl benzene mainly is alkylated to react and is made by C15 n-alkane with benzene at present；Traditional technology
With HF or AlC13For catalyst, production line mainly has 3 kinds: (1) chloralkane that normal paraffin chlorination generates, in AlCl3
In the presence of catalyst and benzene is alkylated reaction；(2) chloralkane that normal paraffin chlorination generates, then dehydrochlorination generate phase
Then the monoolefine answered is alkylated reaction with benzene again；(3) n-alkane direct dehydrogenation under platinum catalysis generates corresponding single
Alkene, then carry out reaction with benzene in the presence of HF catalyst and generate pentadecyl benzene.Prepare the traditional handicraft road of pentadecyl benzene
Line is as shown in Figure 1.
The above-mentioned prior art for preparing pentadecylcyclohexane and pentadecyl benzene is constantly present such or some like that asks
Topic, for example, by-product and the three wastes it is more, target product selectivity is lower, and cost of material is higher etc..Therefore, it needs to research and develop
A kind of cost of material is lower, by-product and the three wastes are less, the higher pentadecylcyclohexane of target product selectivity and pentadecane
Base benzene production technology.
Summary of the invention
The technical problem to be solved by the present invention is in view of the deficiencies of the prior art, provide one kind using anacardol as raw material system
The method of standby pentadecylcyclohexane and pentadecyl benzene.Raw material anacardol used in this method is with renewable, price is low
It is honest and clean, have excellent performance, abundance the advantages that, by-product and the three wastes are less in production process, and target product selectivity is higher, 15
Alkyl cyclohexane and pentadecyl benzene yield are high.
For this purpose, the present invention provides a kind of sides for preparing pentadecylcyclohexane and pentadecyl benzene using anacardol as raw material
Method comprising:
Fixed bed reactors equipped with catalyst are carried out nitrogen treatment by step B；
Step C is passed through hydrogen into the fixed bed reactors equipped with catalyst through nitrogen treatment；
Anacardol is sent into the hydrogen stream that hydrogen is formed by step D, and the gas-liquid mixture stream formed after mixing, which enters, to be equipped with
The fixed bed reactors of catalyst generate pentadecylcyclohexane and pentadecyl benzene after reaction；
Wherein, the catalyst is the Pt/Al of 20-40 mesh2O3Granule type solid catalyst.
According to the present invention, the Pt/Al2O3Granule type solid catalyst is loaded in aluminium oxide basis carrier particle surface
Metal platinum is formed.
In some embodiments of the invention, in stepb, the temperature of nitrogen treatment is 300-400 DEG C.
In some embodiments of the invention, in stepb, the time of nitrogen treatment is 1-2 hours.
In some embodiments of the invention, in step C, to the fixed bed reaction equipped with catalyst through nitrogen treatment
It is passed through hydrogen to pressure in device and reaches 3.0-4.0MPa.
In some embodiments of the invention, in step C, the flow velocity of hydrogen is 100-120ml/min, preferably hydrogen
Flow velocity is 100ml/min.
In some embodiments of the invention, in step D, with 2.4-2.6h-1Air speed by anacardol be sent into hydrogen shape
At hydrogen stream in, preferably with 2.4 air speed will anacardol be sent into hydrogen formed hydrogen stream in.
In some embodiments of the invention, in step D, the feed flow rate of anacardol is 0.2-0.4ml/min, cashew nut
The feed flow rate of phenol is 0.2ml/min.
In some embodiments of the invention, in step D, the temperature of the reaction is 300-400 DEG C.
The raw materials used in the present invention anacardol is the main component of cashew nut shell oil.Cashew nut shell oil is the agriculture in cashew nut process
Industry by-product, by natural cashew nut shell through being pyrolyzed, supercritical CO2The methods of extraction is made.The main component of anacardol is 3- 15
Alkylphenol, the phenolic hydroxyl group in molecule can be carried out aldol condensation, and the unsaturated long-chain on phenyl ring makes anacardol have both sexes, benzene
Ring can carry out π-pi-electron overlapping and functionalization, these features make anacardol become the idealization for preparing various functional materials
Learn modification presoma.Anacardol is rare natural biomass phenol, belongs to the environmentally protective raw material of industry, because its have can be again
It is raw, cheap, have excellent performance, abundance the advantages that, become Recent study exploitation hot spot.As a kind of day abundant
Right renewable resource, anacardol are widely used in the every field such as industry, agricultural, national defence, polynary to promotion China's energy
Change, renewable energy industrial upgrading alleviate the energy and environmental pressure with very far-reaching realistic meaning.
Granular pattern acidic catalyst Pt/Al used in the present invention2O3With excellent catalytic activity, catalytic stability and resist
Coke formation, and catalyst is renewable and reuses；By-product and the three wastes are less in the method for the present invention production process, target
Higher (the pentadecylcyclohexane: 80.6%) of selectivity of product；The method of the present invention product yield is relatively high, can achieve 80%
Above liquid yield, reaction generate 49.6%-80.6% (mol), the pentadecane that pentadecylcyclohexane accounts for about liquid product
Base benzene accounts for about the 10.3%-23.4% (mol) of liquid product, such as increases catalyst amount, increases pressure, product yield can also be into
One step improves.Production technology of the invention and easy to operate, only needs single step reaction, is particularly conducive to industrialized production.
Detailed description of the invention
Fig. 1 shows the conventional processing routes for preparing pentadecyl benzene.
Fig. 2 shows that the reaction mechanism of pentadecylcyclohexane is made in anacardol catalytic hydrogenation.
Fig. 3 shows that the reaction mechanism of pentadecyl benzene is made in pentadecyl phenol catalytic hydrogenation.
Fig. 4 is the GC/MS spectrogram of product prepared in embodiment 5.
Specific embodiment
It elaborates below in conjunction with specific embodiment and attached drawing to the present invention, these embodiments only rise illustrative
Effect, it is not limited to application range of the invention.
Heretofore described anacardol main component is compound described in formula 1；The pentadecylcyclohexane is described in formula 2
Compound；The pentadecyl benzene is compound described in formula 3.
The reaction mechanism of the obtained pentadecylcyclohexane of anacardol catalytic hydrogenation is as shown in Figure 2 in the present invention.
The reaction mechanism of the obtained pentadecyl benzene of pentadecyl phenol catalytic hydrogenation is as shown in Figure 3 in the present invention.
According to certain embodiments of the present invention, the method for the present invention the following steps are included:
The Pt/Al of 20-40 mesh is added into tubular reactor by step A2O3It is anti-that granule type solid catalyst constitutes fixed bed
Answer device；
Step B will be equipped with the fixed bed reactors of catalyst, be placed in tubular heater, heats and rise in nitrogen atmosphere
Temperature to 300-400 DEG C progress nitrogen treatment 1-2 hours, remove reactor in air；
Step C is preferably urged with the flow velocity of 100ml/min to being equipped with through nitrogen treatment with the flow velocity of 100-120ml/min
It is passed through hydrogen in the fixed bed reactors of agent, pressure is made to reach 3.0-4.0MPa；
Step D, after temperature and pressure are stablized, with 2.4-2.6h-1Air speed, preferably with 2.4h-1Air speed, and with
Anacardol is preferably sent into the hydrogen stream that hydrogen is formed with the flow velocity of 0.2ml/min by the flow velocity of 0.2-0.4ml/min, mixing
The gas-liquid mixture stream formed afterwards enter equipped with catalyst reactor, 300-400 DEG C at a temperature of reaction after generate 15
Alkyl cyclohexane and pentadecyl benzene；Liquid product yield is up to 80% or more.
It is right using gas chromatography-mass spectrometry (Aligent 7890A 5975C, Agilent company of the U.S.) in the present invention
Product is detected.
Embodiment
Embodiment 1: pentadecylcyclohexane and pentadecyl benzene are prepared by raw material of anacardol:
(1) Pt/Al of 5 grams of 20-40 mesh is added into tubular reactor2O3It is anti-that granule type solid catalyst constitutes fixed bed
Answer device；
(2) fixed bed reactors of catalyst will be housed, be placed in tubular heater, be heated in nitrogen atmosphere
400 DEG C progress nitrogen treatment 1-2 hours, remove reactor in air；
(3) hydrogen is passed through into the fixed bed reactors equipped with catalyst through nitrogen treatment with the flow velocity of 100ml/min,
Pressure is set to reach 3.5MPa；
(4) after temperature and pressure are stablized, use product pump with 2.4h-1Air speed and with the flow velocity of 0.2ml/min by waist
Fruit phenol is sent into the hydrogen stream that hydrogen is formed, and the gas-liquid mixture stream formed after mixing enters the fixed bed reaction equipped with catalyst
Device generates pentadecylcyclohexane (49.6%) and pentadecyl benzene (23.4%) in 400 DEG C of at a temperature of reaction.Product yield
Up to 80% or more.
Embodiment 2: pentadecylcyclohexane and pentadecyl benzene are prepared by raw material of anacardol:
(1) Pt/Al of 5 grams of 20-40 mesh is added into tubular reactor2O3It is anti-that granule type solid catalyst constitutes fixed bed
Answer device；
(2) fixed bed reactors of catalyst will be housed, be placed in tubular heater, be heated in nitrogen atmosphere
400 DEG C progress nitrogen treatment 1-2 hours, remove reactor in air；
(3) hydrogen is passed through into the fixed bed reactors equipped with catalyst through nitrogen treatment with the flow velocity of 100ml/min,
Pressure is set to reach 3.0MPa；
(4) after temperature and pressure are stablized, use product pump with 2.4h-1Air speed and with the flow velocity of 0.2ml/min by waist
Fruit phenol is sent into the hydrogen stream that hydrogen is formed, and the gas-liquid mixture stream formed after mixing enters the fixed bed reaction equipped with catalyst
Device, 400 DEG C at a temperature of carry out reaction and generate pentadecylcyclohexane (39.7%) and pentadecyl benzene (13.9%).Product
Yield is 80% or more.
Embodiment 3: pentadecylcyclohexane and pentadecyl benzene are prepared by raw material of anacardol:
(1) Pt/Al of 5 grams of 20-40 mesh is added into tubular reactor2O3It is anti-that granule type solid catalyst constitutes fixed bed
Answer device；
(2) fixed bed reactors of catalyst will be housed, be placed in tubular heater, be heated in nitrogen atmosphere
400 DEG C progress nitrogen treatment 1-2 hours, remove reactor in air；
(3) hydrogen is passed through into the fixed bed reactors equipped with catalyst through nitrogen treatment with the flow velocity of 100ml/min,
Pressure is set to reach 4.0MPa；
(4) after temperature and pressure are stablized, use product pump with 2.4h-1Air speed and with the flow velocity of 0.2ml/min by waist
Fruit phenol is sent into the hydrogen stream that hydrogen is formed, and the gas-liquid mixture stream formed after mixing enters the fixed bed reaction equipped with catalyst
Device, 400 DEG C at a temperature of carry out reaction and generate pentadecylcyclohexane (56%) and pentadecyl benzene (11.5%).Product is received
Rate is up to 80% or more.
Embodiment 4: pentadecylcyclohexane and pentadecyl benzene are prepared by raw material of anacardol:
(1) Pt/Al of 5 grams of 20-40 mesh is added into tubular reactor2O3It is anti-that granule type solid catalyst constitutes fixed bed
Answer device；
(2) fixed bed reactors of catalyst will be housed, be placed in tubular heater, be heated in nitrogen atmosphere
380 DEG C progress nitrogen treatment 1-2 hours, remove reactor in air；
(3) hydrogen is passed through into the fixed bed reactors equipped with catalyst through nitrogen treatment with the flow velocity of 100ml/min,
Pressure is set to reach 4.0MPa；
(4) after temperature and pressure are stablized, use product pump with 2.4h-1Air speed and with the flow velocity of 0.2ml/min by waist
Fruit phenol is sent into the hydrogen stream that hydrogen is formed, and the gas-liquid mixture stream formed after mixing enters the fixed bed reaction equipped with catalyst
Device, 380 DEG C at a temperature of carry out reaction and generate pentadecylcyclohexane (61.5%) and pentadecyl benzene (9.7%).Product
Yield is up to 80% or more.
Embodiment 5: pentadecylcyclohexane and pentadecyl benzene are prepared by raw material of anacardol:
(1) Pt/Al of 5 grams of 20-40 mesh is added into tubular reactor2O3It is anti-that granule type solid catalyst constitutes fixed bed
Answer device；
(2) fixed bed reactors of catalyst will be housed, be placed in tubular heater, be heated in nitrogen atmosphere
360 DEG C progress nitrogen treatment 1-2 hours, remove reactor in air；
(3) hydrogen is passed through into the fixed bed reactors equipped with catalyst through nitrogen treatment with the flow velocity of 100ml/min,
Pressure is set to reach 4.0MPa；
(4) after temperature and pressure are stablized, use product pump with 2.4h-1Air speed and with the flow velocity of 0.2ml/min by waist
Fruit phenol is sent into the hydrogen stream that hydrogen is formed, and the gas-liquid mixture stream formed after mixing enters the fixed bed reaction equipped with catalyst
Device, 360 DEG C at a temperature of carry out reaction and generate pentadecylcyclohexane (80.5%) and pentadecyl benzene (9.2%).Product
Yield is up to 80% or more.
Product is carried out using gas chromatography-mass spectrometry (Aligent 7890A 5975C, Agilent company of the U.S.)
Detection, GC/MS spectrogram are as shown in Figure 4.
It can be seen that by case study on implementation described above through control reaction condition, available higher product yield,
Under optimum reaction condition (reaction temperature is 360 DEG C, and hydrogen pressure is 4.0MPa), pentadecylcyclohexane selectivity highest.
It should be noted that embodiment described above for explaining only the invention, is not constituted to of the invention any
Limitation.By referring to exemplary embodiments, invention has been described, it should be appreciated that word used in it is descriptive
With explanatory vocabulary, rather than limited vocabulary.The present invention can be made within the scope of the claims by regulation
Modification, and the present invention is revised in without departing substantially from scope and spirit of the present invention.Although the present invention described in it relates to
And specific method, material and embodiment, it is not intended that the present invention is limited to particular case disclosed in it, on the contrary, this hair
It is bright to can be extended to other all methods and applications with the same function.
Claims (8)
1. a kind of method for preparing pentadecylcyclohexane and pentadecyl benzene as raw material using anacardol comprising:
Fixed bed reactors equipped with catalyst are carried out nitrogen treatment by step B；
Step C is passed through hydrogen into the fixed bed reactors equipped with catalyst through nitrogen treatment；
Anacardol is sent into the hydrogen stream that hydrogen is formed by step D, and the gas-liquid mixture stream formed after mixing enters equipped with catalysis
The fixed bed reactors of agent generate pentadecylcyclohexane and pentadecyl benzene after reaction；
Wherein, the catalyst is the Pt/Al of 20-40 mesh2O3Granule type solid catalyst；
In step D, the temperature of the reaction is 300-400 DEG C.
2. the method according to claim 1, wherein the Pt/Al2O3Granule type solid catalyst is to aoxidize
Aluminium base plinth carrier particle surface loaded metal platinum is formed.
3. method according to claim 1 or 2, which is characterized in that in stepb, the temperature of nitrogen treatment is 300-400
℃。
4. method according to claim 1 or 2, which is characterized in that in stepb, the time of nitrogen treatment is that 1-2 is small
When.
5. method according to claim 1 or 2, which is characterized in that in step C, catalysis is housed to through nitrogen treatment
It is passed through hydrogen to pressure in the fixed bed reactors of agent and reaches 3.0-4.0MPa.
6. method according to claim 1 or 2, which is characterized in that in step C, the flow velocity of hydrogen is 100-120ml/
min。
7. method according to claim 1 or 2, which is characterized in that in step D, with 2.4-2.6h-1Air speed by cashew nut
Phenol is sent into the hydrogen stream that hydrogen is formed.
8. method according to claim 1 or 2, which is characterized in that in step D, the feed flow rate of anacardol is 0.2-
0.4ml/min。
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