CN106542948A - In the method that Cardanol prepares pentadecylcyclohexane and pentadecyl benzene as raw material - Google Patents
In the method that Cardanol prepares pentadecylcyclohexane and pentadecyl benzene as raw material Download PDFInfo
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- CN106542948A CN106542948A CN201610903813.0A CN201610903813A CN106542948A CN 106542948 A CN106542948 A CN 106542948A CN 201610903813 A CN201610903813 A CN 201610903813A CN 106542948 A CN106542948 A CN 106542948A
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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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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- 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 method for preparing pentadecylcyclohexane and pentadecyl benzene as raw material with Cardanol.The method includes：Will be equipped with Pt/Al2O3The fixed bed reactors of granule type solid catalyst carry out nitrogen treatment；Hydrogen is passed through in the fixed bed reactors equipped with catalyst of Jing nitrogen treatments；Cardanol is sent in the hydrogen stream that hydrogen is formed, the gas-liquid mixed logistics formed after mixing enters the fixed bed reactors equipped with catalyst, after reaction, generate pentadecylcyclohexane and pentadecyl benzene.Granule type solid catalyst Pt/Al used by the present invention2O3With excellent catalysis activity, catalytic stability and anti-carbon deposition ability, and catalyst is renewable and reuses；In the inventive method production process, by-product and the three wastes are less, and target product selectivity is higher；The inventive method product yield is of a relatively high；The production technology and easy to operate of the present invention, only needs single step reaction, is particularly conducive to industrialized production.
Description
Technical field
The invention belongs to Industrial Catalysis field, and in particular to it is a kind of with Cardanol as raw material prepare pentadecylcyclohexane and
The method of pentadecyl benzene.Specifically related to one kind prepares pentadecane basic ring on fixed bed hydrogenation reactor by raw material of Cardanol
The method of hexane and pentadecyl benzene.
Background technology
Pentadecylcyclohexane is a kind of important Organic Chemicals intermediate, also can be used as liquid alkane fuel.Mesh
The production of front pentadecylcyclohexane is mainly by the method for organic synthesiss.
Pentadecyl benzene is the important component part of linear alkyl benzene (or claiming 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 topmost raw material of domestic and industrial detergent.
The production of pentadecyl benzene at present is mainly alkylated reaction by C15 n-alkanes and benzene and makes；Conventional art
With HF or AlC13For catalyst, its production line mainly has 3 kinds：(1) chloralkane that normal paraffin chlorination is generated, in AlCl3
Reaction is alkylated with benzene in the presence of catalyst；(2) chloralkane that normal paraffin chlorination is generated, then dehydrochlorination generates phase
The monoolefine answered, is then alkylated reaction again with benzene；(3) n-alkane direct dehydrogenation under platinum catalysis generates corresponding single
Alkene, then in the presence of HF catalyst carry out reaction and generate pentadecyl benzene with 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 are asked like that
Topic, such as by-product and the three wastes are more, and target product selectivity is relatively low, and cost of material is higher etc..Therefore, research and development are needed badly
A kind of cost of material is relatively low, by-product and the three wastes are less, the higher pentadecylcyclohexane of target product selectivity and pentadecane
Base benzene production technology.
The content of the invention
The technical problem to be solved is for the deficiencies in the prior art, there is provided one kind is with Cardanol as raw material system
The method of standby pentadecylcyclohexane and pentadecyl benzene.The raw material Cardanol used by the method has renewable, price low
The advantages of honest and clean, excellent performance, abundance, in production process, by-product and the three wastes are less, and target product selectivity is higher, and 15
Alkyl cyclohexane and pentadecyl benzene yield are high.
For this purpose, a kind of the invention provides side for preparing pentadecylcyclohexane and pentadecyl benzene with Cardanol as raw material
Method, which includes：
Step B, the fixed bed reactors that will be equipped with catalyst carry out nitrogen treatment；
Step C, is passed through hydrogen in the fixed bed reactors equipped with catalyst of Jing nitrogen treatments；
Step D, Cardanol is sent in the hydrogen stream that hydrogen is formed, and the gas-liquid mixed logistics formed after mixing is entered and is equipped with
The fixed bed reactors of catalyst, generate pentadecylcyclohexane and pentadecyl benzene after reaction；
Wherein, Pt/Al of the catalyst for 20-40 mesh2O3Granule type solid catalyst.
According to the present invention, the Pt/Al2O3Granule type solid catalyst is in the carrier particle surface load of aluminium oxide basis
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 of Jing nitrogen treatments
Hydrogen is passed through in device 3.0-4.0MPa is reached to pressure.
In some embodiments of the invention, in step C, the flow velocity of hydrogen is 100-120ml/min, preferred hydrogen
Flow velocity is 100ml/min.
In some embodiments of the invention, in step D, with 2.4-2.6h-1Air speed by Cardanol send into hydrogen shape
Into hydrogen stream in, preferably with 2.4 air speed by Cardanol send into hydrogen formed hydrogen stream in.
In some embodiments of the invention, in step D, the feed flow rate of Cardanol be 0.2-0.4ml/min, Fructus anacardii
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 Cardanol of the present invention is the main component of cashew shell oil.Cashew shell oil is the agriculture in the Fructus anacardii course of processing
Industry by-product, is pyrolyzed by natural cashew nut shell Jing, supercritical CO2The methods such as extraction are obtained.The main component of Cardanol is 3- 15
Alkylphenol, the phenolic hydroxyl group in its molecule can carry out aldol condensation, and the unsaturated long-chain on phenyl ring makes Cardanol have both sexes, benzene
Ring can carry out π-pi-electron and overlap and functionalization, and these features cause Cardanol to become the idealization for preparing various functions material
Learn modification presoma.Cardanol is rare natural biomass phenol, belongs to the raw material of industry of environmental protection, because which has can be again
The advantages of raw, cheap, excellent performance, abundance, become the focus of Recent study exploitation.As a kind of abundant day
Right Renewable resource, Cardanol are widely used in the every field such as industry, agricultural, national defence, to promoting China's energy polynary
Change, regenerative resource industrial upgrading, the alleviation energy and ambient pressure have very far-reaching realistic meaning.
Granular pattern acidic catalyst Pt/Al used by the present invention2O3With excellent catalysis activity, catalytic stability and anti-
Coke formation, and catalyst is renewable and reuses；In the inventive method production process, by-product and the three wastes are less, target
Higher (the pentadecylcyclohexane of selectivity of product：80.6%)；The inventive method product yield is of a relatively high, can reach 80%
Liquid yield above, reaction generate pentadecylcyclohexane and account for the 49.6%-80.6% (mol) of fluid product, pentadecane
Base benzene accounts for the 10.3%-23.4% (mol) of fluid product, such as increases catalyst amount, increase pressure, and product yield can also enter
One step is improved.The production technology and easy to operate of the present invention, only needs single step reaction, is particularly conducive to industrialized production.
Description of the drawings
Fig. 1 shows the conventional processing routes for preparing pentadecyl benzene.
Fig. 2 shows that Cardanol catalytic hydrogenation is obtained the reaction mechanism of pentadecylcyclohexane.
Fig. 3 shows that pentadecyl phenol catalytic hydrogenation is obtained the reaction mechanism of pentadecyl benzene.
GC/MS spectrograms of the Fig. 4 for product prepared in embodiment 5.
Specific embodiment
The present invention is elaborated below in conjunction with specific embodiment and accompanying drawing, these embodiments only rise illustrative
Effect, it is not limited to the range of application of the present invention.
Heretofore described Cardanol 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.
In the present invention, the reaction mechanism of the prepared pentadecylcyclohexane of Cardanol catalytic hydrogenation is as shown in Figure 2.
In the present invention, the reaction mechanism of the prepared pentadecyl benzene of pentadecyl phenol catalytic hydrogenation is as shown in Figure 3.
According to certain embodiments of the present invention, the inventive method is comprised the following steps：
Step A, adds the Pt/Al of 20-40 mesh in tubular reactor2O3It 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, and the heating in nitrogen atmosphere rises
Temperature carries out nitrogen treatment 1-2 hour to 300-400 DEG C, removes the air in reactor；
Step C, with the flow velocity of 100-120ml/min, preferably with the flow velocity of 100ml/min to Jing nitrogen treatments equipped with urging
Hydrogen is passed through in the fixed bed reactors of agent, makes pressure reach 3.0-4.0MPa；
Step D, after temperature and pressure are stable, with 2.4-2.6h-1Air speed, preferably with 2.4h-1Air speed, and with
The flow velocity of 0.2-0.4ml/min, is preferably sent into Cardanol in the hydrogen stream that hydrogen is formed with the flow velocity of 0.2ml/min, mixing
The gas-liquid mixed logistics for being formed afterwards enters the reactor equipped with catalyst, generates ten five after reacting at a temperature of 300-400 DEG C
Alkyl cyclohexane and pentadecyl benzene；Liquid product yield is up to more than 80%.
It is right using gas chromatograph-mass spectrometer (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 Cardanol：
(1) Pt/Al of 5 grams of 20-40 mesh is added in tubular reactor2O3It is anti-that granule type solid catalyst constitutes fixed bed
Answer device；
(2) fixed bed reactors of catalyst are will be equipped with, is placed in tubular heater, is heated in nitrogen atmosphere
400 DEG C carry out nitrogen treatment 1-2 hour, remove the air in reactor；
(3) hydrogen is passed through with the flow velocity of 100ml/min in the fixed bed reactors equipped with catalyst of Jing nitrogen treatments,
Pressure is made to reach 3.5MPa；
(4) after temperature and pressure are stable, product pump is adopted with 2.4h-1Air speed and with the flow velocity of 0.2ml/min by waist
Fruit phenol is sent in the hydrogen stream that hydrogen is formed, and the gas-liquid mixed logistics formed after mixing enters the fixed bed reaction equipped with catalyst
Device, reacts at a temperature of 400 DEG C and generates pentadecylcyclohexane (49.6%) and pentadecyl benzene (23.4%).Product yield
Up to more than 80%.
Embodiment 2：Pentadecylcyclohexane and pentadecyl benzene are prepared by raw material of Cardanol：
(1) Pt/Al of 5 grams of 20-40 mesh is added in tubular reactor2O3It is anti-that granule type solid catalyst constitutes fixed bed
Answer device；
(2) fixed bed reactors of catalyst are will be equipped with, is placed in tubular heater, is heated in nitrogen atmosphere
400 DEG C carry out nitrogen treatment 1-2 hour, remove the air in reactor；
(3) hydrogen is passed through with the flow velocity of 100ml/min in the fixed bed reactors equipped with catalyst of Jing nitrogen treatments,
Pressure is made to reach 3.0MPa；
(4) after temperature and pressure are stable, product pump is adopted with 2.4h-1Air speed and with the flow velocity of 0.2ml/min by waist
Fruit phenol is sent in the hydrogen stream that hydrogen is formed, and the gas-liquid mixed logistics formed after mixing enters the fixed bed reaction equipped with catalyst
Device, carries out reaction at a temperature of 400 DEG C and generates pentadecylcyclohexane (39.7%) and pentadecyl benzene (13.9%).Product
Yield is more than 80%.
Embodiment 3：Pentadecylcyclohexane and pentadecyl benzene are prepared by raw material of Cardanol：
(1) Pt/Al of 5 grams of 20-40 mesh is added in tubular reactor2O3It is anti-that granule type solid catalyst constitutes fixed bed
Answer device；
(2) fixed bed reactors of catalyst are will be equipped with, is placed in tubular heater, is heated in nitrogen atmosphere
400 DEG C carry out nitrogen treatment 1-2 hour, remove the air in reactor；
(3) hydrogen is passed through with the flow velocity of 100ml/min in the fixed bed reactors equipped with catalyst of Jing nitrogen treatments,
Pressure is made to reach 4.0MPa；
(4) after temperature and pressure are stable, product pump is adopted with 2.4h-1Air speed and with the flow velocity of 0.2ml/min by waist
Fruit phenol is sent in the hydrogen stream that hydrogen is formed, and the gas-liquid mixed logistics formed after mixing enters the fixed bed reaction equipped with catalyst
Device, carries out reaction at a temperature of 400 DEG C and generates pentadecylcyclohexane (56%) and pentadecyl benzene (11.5%).Product is received
Rate is up to more than 80%.
Embodiment 4：Pentadecylcyclohexane and pentadecyl benzene are prepared by raw material of Cardanol：
(1) Pt/Al of 5 grams of 20-40 mesh is added in tubular reactor2O3It is anti-that granule type solid catalyst constitutes fixed bed
Answer device；
(2) fixed bed reactors of catalyst are will be equipped with, is placed in tubular heater, is heated in nitrogen atmosphere
380 DEG C carry out nitrogen treatment 1-2 hour, remove the air in reactor；
(3) hydrogen is passed through with the flow velocity of 100ml/min in the fixed bed reactors equipped with catalyst of Jing nitrogen treatments,
Pressure is made to reach 4.0MPa；
(4) after temperature and pressure are stable, product pump is adopted with 2.4h-1Air speed and with the flow velocity of 0.2ml/min by waist
Fruit phenol is sent in the hydrogen stream that hydrogen is formed, and the gas-liquid mixed logistics formed after mixing enters the fixed bed reaction equipped with catalyst
Device, carries out reaction at a temperature of 380 DEG C and generates pentadecylcyclohexane (61.5%) and pentadecyl benzene (9.7%).Product
Yield is up to more than 80%.
Embodiment 5：Pentadecylcyclohexane and pentadecyl benzene are prepared by raw material of Cardanol：
(1) Pt/Al of 5 grams of 20-40 mesh is added in tubular reactor2O3It is anti-that granule type solid catalyst constitutes fixed bed
Answer device；
(2) fixed bed reactors of catalyst are will be equipped with, is placed in tubular heater, is heated in nitrogen atmosphere
360 DEG C carry out nitrogen treatment 1-2 hour, remove the air in reactor；
(3) hydrogen is passed through with the flow velocity of 100ml/min in the fixed bed reactors equipped with catalyst of Jing nitrogen treatments,
Pressure is made to reach 4.0MPa；
(4) after temperature and pressure are stable, product pump is adopted with 2.4h-1Air speed and with the flow velocity of 0.2ml/min by waist
Fruit phenol is sent in the hydrogen stream that hydrogen is formed, and the gas-liquid mixed logistics formed after mixing enters the fixed bed reaction equipped with catalyst
Device, carries out reaction at a temperature of 360 DEG C and generates pentadecylcyclohexane (80.5%) and pentadecyl benzene (9.2%).Product
Yield is up to more than 80%.
Product is carried out using gas chromatograph-mass spectrometer (Aligent 7890A 5975C, Agilent company of the U.S.)
Detection, GC/MS spectrograms are as shown in Figure 4.
Can be seen that by controlling reaction condition by case study on implementation described above, higher product yield can be obtained,
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 is only used for explaining the present invention, do not constitute to any of the present invention
Limit.By referring to exemplary embodiments, invention has been described, it should be appreciated that word wherein used is descriptive
With explanatory vocabulary, rather than limited vocabulary.Within the scope of the claims the present invention can be made 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 which is related to
And specific method, material and embodiment, it is not intended that the present invention is limited to wherein disclosed particular case, conversely, this
It is bright to can be extended to other all methods and applications with identical function.
Claims (9)
1. a kind of method for preparing pentadecylcyclohexane and pentadecyl benzene as raw material with Cardanol, which includes：
Step B, the fixed bed reactors that will be equipped with catalyst carry out nitrogen treatment；
Step C, is passed through hydrogen in the fixed bed reactors equipped with catalyst of Jing nitrogen treatments；
Step D, Cardanol is sent in the hydrogen stream that hydrogen is formed, and the gas-liquid mixed logistics formed after mixing is entered equipped with catalysis
The fixed bed reactors of agent, generate pentadecylcyclohexane and pentadecyl benzene after reaction；
Wherein, Pt/Al of the catalyst for 20-40 mesh2O3Granule type solid catalyst.
2. method according to claim 1, it is characterised in that the Pt/Al2O3Granule type solid catalyst is in oxidation
Aluminium base plinth carrier particle surface loaded metal platinum is formed.
3. method according to claim 1 and 2, it is characterised in that in stepb, the temperature of nitrogen treatment is 300-400
℃。
4. the method according to any one in claim 1-3, it is characterised in that in stepb, the time of nitrogen treatment
For 1-2 hours.
5. the method according to any one in claim 1-4, it is characterised in that in step C, to Jing nitrogen treatments
Hydrogen is passed through in fixed bed reactors equipped with catalyst 3.0-4.0MPa is reached to pressure.
6. the method according to any one in claim 1-5, it is characterised in that in step C, the flow velocity of hydrogen is
100-120ml/min。
7. the method according to any one in claim 1-6, it is characterised in that in step D, with 2.4-2.6h-1's
Cardanol is sent in the hydrogen stream that hydrogen is formed by air speed.
8. the method according to any one in claim 1-7, it is characterised in that in step D, the feed stream of Cardanol
Speed is 0.2-0.4ml/min.
9. the method according to any one in claim 1-8, it is characterised in that in step D, the temperature of the reaction
For 300-400 DEG C.
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| CN201610903813.0A CN106542948B (en) | 2016-10-17 | 2016-10-17 | The method for preparing pentadecylcyclohexane and pentadecyl benzene as raw material using anacardol |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113150823A (en) * | 2021-04-02 | 2021-07-23 | 福建省格兰尼生物工程股份有限公司 | Method for producing aromatic hydrocarbon and biodiesel through cardanol hydrogenation |
-
2016
- 2016-10-17 CN CN201610903813.0A patent/CN106542948B/en active Active
Non-Patent Citations (2)
| Title |
|---|
| FOSTER, ANDREW J. ET AL: "The Synergy of the Support Acid Function and the Metal Function in the Catalytic Hydrodeoxygenation of m-Cresol", 《TOPICS IN CATALYSIS》 * |
| MORE, ARVIND S. ET AL: "Synthesis and characterization of polyesters based on 1,1,1-[bis(4-hydroxyphenyl)-4"-pentadecylphenyl]ethane", 《POLYMER INTERNATIONAL》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113150823A (en) * | 2021-04-02 | 2021-07-23 | 福建省格兰尼生物工程股份有限公司 | Method for producing aromatic hydrocarbon and biodiesel through cardanol hydrogenation |
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