CN105237328B - Method for producing 2,6 diisopropyl naphthalenes - Google Patents
Method for producing 2,6 diisopropyl naphthalenes Download PDFInfo
- Publication number
- CN105237328B CN105237328B CN201410314465.4A CN201410314465A CN105237328B CN 105237328 B CN105237328 B CN 105237328B CN 201410314465 A CN201410314465 A CN 201410314465A CN 105237328 B CN105237328 B CN 105237328B
- Authority
- CN
- China
- Prior art keywords
- naphthalene
- dipn
- diisopropyl
- produce
- sio
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The present invention relates to a kind of method for being used to produce 2,6 diisopropyl naphthalenes, mainly solve prior art and there is the problem of 2,6 diisopropyl naphthalenes are selectively low, heavy constituent is more, catalyst inactivation is fast.Catalyst used in the present invention is organic silicone zeolite, and it includes the composition of following molar relationship：(1/n)Al2O3：SiO2：(m/n) n=10~350, m=0.02~50, R is at least one of alkyl, alkane alkenyl or phenyl in R, formula；The Si containing organic silicone zeolite29NMR solid state nmr collection of illustrative plates is comprised at least between 80~+50ppm a Si29Nuclear magnetic resonance spectral peak；The X x ray diffractions collection of illustrative plates containing organic silicone zeolite is 13.2 ± 0.2,12.3 ± 0.1,10.9 ± 0.3,9.1 ± 0.3,6.8 ± 0.2,6.1 ± 0.2,5.6 ± 0.2,4.4 ± 0.3, there are d spacing maximums at 4.0 ± 0.3,3.6 ± 0.2,3.4 ± 0.1 and 3.3 ± 0.2 angstroms, available in the industrial production for preparing 2,6 diisopropyl naphthalenes.
Description
Technical field
The present invention relates to a kind of method for producing 2,6- diisopropyl naphthalenes.
Background technology
Diisopropyl naphthalene is a low condensation point of class colorless and odorless low toxicity, widely used important Organic Chemicals.It is therein
2,6- diisopropyl naphthalenes are the raw materials for manufacturing the poly- 2,6- naphthalenes diethyl adipate (PEN) of high-performance polymer.PEN has heat-resisting well
The superior quality such as property, gas barrier, ultraviolet barrier property and chemical proofing, can manufacture hot canning beverage bottle, can return
Beer bottle, cosmetics of super quality bottle or high performance thin film are received, is current very powerful and exceedingly arrogant new polyester material.Manufacture 2,6- diisopropyls
The technique of base naphthalene is except using naphthalene and propylene liquid-phase alkylation method, it is also necessary to the accessory substance for producing alkylated reaction, such as isopropyl
Other isomers of base naphthalene and diisopropyl naphthalene, are converted with the method for transalkylation, to improve 2,6- diisopropyls
The yield of base naphthalene.
The molecular sieve of MWW structures has half basket structure of ten-ring and twelve-ring duct and opening simultaneously, and has hyperpyrexia
Stability and stronger acidity, are widely used in the reaction such as alkylation of benzene.Transalkylation reaction also referred to as intermolecular and
The isomerization reaction of intramolecular.Seldom have been reported that MWW molecular sieves are applied to prepare the serial anti-of 2,6- diisopropyl naphthalenes in document
Should, for the just less of transalkylating reaction.
Document US4950824 refer to can with including isopropyl naphthalene and diisopropyl naphthalene be raw material obtain it is a kind of containing it is single,
The mixture of double and triisopropyl naphthalene, the method that 2,6-DIPN is obtained after being separated through component.JP02088531 is using containing
The solid acid catalyst of sial, after naphthalene and propylene reaction obtain list and diisopropyl naphthalene product, at relatively high temperatures by product
Transalkylation reaction is carried out, the yield of 2,6-DIPN is improved.
R.Brzozowski is in Journal of Catalysis A:General166(1998):2,6-DIPN in 21-27
And 1,3- and 1,7-DIPN are used to isomerization reaction, a variety of isomers have been obtained in the presence of acidic catalyst
Mixture.But whole reaction has only been carried out 6 hours.
All there is the problem of 2,6- diisopropyl naphthalenes are selectively low, heavy constituent is more, catalyst inactivation is fast in above method.
The content of the invention
The technical problems to be solved by the invention are that prior art has that 2,6- diisopropyl naphthalenes are selectively low, heavy constituent
It is many, there is provided a kind of new method for producing 2,6-DIPN the problem of catalyst inactivation is fast.This method has 2,6-
Diisopropyl naphthalene is selectively good, the characteristics of catalyst life is long.
In order to solve the above technical problems, the technical scheme that the present invention takes is as follows：One kind is used to produce 2,6- diisopropyls
The method of naphthalene, using the mixture of diisopropyl naphthalene or isopropyl naphthalene and diisopropyl naphthalene as raw material, reaction temperature be 150~
300 DEG C, the weight space velocity of diisopropyl naphthalene is 0.1~10 hour-1, the weight of isopropyl naphthalene and diisopropyl naphthalene is than for 0~4
Under the conditions of, reaction raw materials are contacted with catalyst, generate 2,6-DIPN；The catalyst by weight percentage include with
Lower component：
A) 50~80% organic silicone zeolite；
B) 20~50% binding agent；
Organic silicone zeolite includes the composition of following molar relationship：(1/n)Al2O3：SiO2：(m/n) n=10 in R, formula
~350, m=0.02~50, R are at least one of alkyl, alkane alkenyl or phenyl；The Si containing organic silicone zeolite29NMR consolidates
Body nuclear magnetic spectrum is comprised at least between -80~+50ppm a Si29Nuclear magnetic resonance spectral peak；The X- containing organic silicone zeolite
X ray diffraction collection of illustrative plates 13.2 ± 0.2,12.3 ± 0.1,10.9 ± 0.3,9.1 ± 0.3,6.8 ± 0.2,6.1 ± 0.2,5.6 ±
0.2,4.4 there are d- spacing maximums at ± 0.3,4.0 ± 0.3,3.6 ± 0.2,3.4 ± 0.1 and 3.3 ± 0.2 angstroms.
In above-mentioned technical proposal, it is preferable that n=20~150, m=0.1~20.
In above-mentioned technical proposal, it is preferable that the alkyl is the alkyl that carbon number is 1~8, the alkane alkenyl is that carbon is former
Subnumber is 2~10 alkane alkenyl.It is highly preferred that the alkyl is methyl or ethyl, the alkane alkenyl is vinyl.
In above-mentioned technical proposal, it is preferable that the binding agent is in aluminum oxide, titanium oxide, zinc oxide or zirconium oxide
It is at least one.
In above-mentioned technical proposal, it is preferable that reaction temperature is 150~270 DEG C.
In above-mentioned technical proposal, it is preferable that the weight space velocity of diisopropyl naphthalene is 0.1~2 hour-1。
In above-mentioned technical proposal, it is preferable that the weight ratio of isopropyl naphthalene and diisopropyl naphthalene is 0.5~3.
The synthetic method of organic silicone zeolite in the inventive method is as follows：
A) organic silicon source, inorganic silicon source, silicon source, alkali, organic amine template and water are mixed, with the SiO in inorganic silicon source2
On the basis of, reactant mixture using molar ratio computing as：SiO2/Al2O3=10~350, organic silicon source/SiO2=0.001~1, OH-/
SiO2=0.01~5.0, H2O/SiO2=5~100, organic amine/SiO2=0.01~2.0；
B) by above-mentioned reactant mixture under the conditions of crystallization temperature is 80~225 DEG C, after reacting 12 hours~10 days
Take out, contain organic silicone zeolite through washing, dry be made.
In above-mentioned technical proposal, inorganic silicon source is selected from Ludox, solid oxidation silicon, silica gel, esters of silicon acis, diatomite or water
At least one of glass.Organic silicon source is selected from least one of halosilanes, silazane or alkoxy silane；Wherein halogen silicon
Alkane is selected from trim,ethylchlorosilane, dimethyldichlorosilane, chlorotriethyl silane, diethyl dichlorosilane, dimethyl chloride bromine silicon
Alkane, dimethyl ethyl chlorosilane, dimethylbutyl chlorosilane, 3,5-dimethylphenyl chlorosilane, dimethylisopropyl chlorosilane, diformazan
Base tertiary butyl chloride silane, dimethyl stearyl chlorosilane, methyl phenyl vinyl chlorosilane, vinyl trichlorosilane or hexichol
At least one of base dichlorosilane；Silazane is selected from HMDS, heptamethyldisilazane, the silicon nitrogen of tetramethyl two
At least one of alkane, divinyl tetramethyl-disilazane or diphenyltetramethyldisilazane；Alkoxy silane be selected from
Trimethylethoxysilane, dimethyldiethoxysilane, trimethylmethoxysilane, dimethyldimethoxysil,ne, front three
At least one of phenyl silane or diphenyl diethoxy silane.Silicon source is selected from sodium aluminate, sodium metaaluminate, sulfuric acid
At least one of aluminium, aluminum nitrate, aluminium chloride, aluminium hydroxide, aluminum oxide, kaolin or montmorillonite.Alkali is inorganic base, for selected from
At least one of lithium hydroxide, sodium hydroxide, potassium hydroxide, rubidium hydroxide or cesium hydroxide.Organic formwork agent is selected from second
Diamines, hexamethylene diamine, cyclohexylamine, hexamethylene imine, heptamethylene imines, pyridine, hexahydropyridine, butylamine, hexylamine, octylame, the last of the ten Heavenly stems
At least one of amine, lauryl amine, cetylamine or octadecylamine.
Reactant mixture is with the SiO in inorganic silicon source2On the basis of, using molar ratio computing preferred scope as：SiO2/Al2O3=20
~150, organic silicon source/SiO2=0.005~0.5, OH-/SiO2=0.05~1.0, H2O/SiO2=10~80, organic formwork
Agent/SiO2=0.05~1.0.Crystallization temperature preferred scope is 120~190 DEG C, and crystallization time preferred scope is 12
~120 hours.Priority scheme is that first ageing 2~100 is small under the conditions of 10~80 DEG C before crystallization for reactant mixture during synthesis
When.
The preparation method of the catalyst used in the inventive method is as follows：
Organic silicone zeolite of above-mentioned synthesis is mixed with binding agent, zeolite content is 50~80 (weight) %.Then 5 are added
(weight) % dilute nitric acid solution is kneaded and formed, drying, is calcined in atmosphere to 480~600 DEG C, roasting time is 1~15 small
When obtain finished catalyst.
As a result of with special diffraction maximum and special Si in the present invention29Organic silicone zeolite of nuclear magnetic resonance spectral peak is urged
Agent active main body, during for transalkylation reaction, restrained effectively the side reactions such as dealkylation, so that triisopropyl
The generation of the heavy constituents such as naphthalene greatly reduces, and the selectivity of 2,6-DIPN is good.The inventors discovered that reaction less than
Under the conditions of 270 DEG C, after 200 hours run, diisopropyl naphthalene is selectively maintained at more than 35%, and triisopropyl naphthalene content is accounted for
Product molar ratio is less than 12%, the sign that catalyst is not inactivated, mole of 2,6-DIPN and 2,7- diisopropyl naphthalene
Than more than 1.0, achieving good technique effect.
Below by embodiment, the invention will be further elaborated.
Embodiment
【Embodiment 1】
Sodium aluminate (is contained into 42.0 weight %Al2O3) 6.1 grams and 2.0 grams of sodium hydroxide be dissolved in 270 grams of water, then stirring
34.7 grams of hexamethylene imine is added in the case of mixing, 150 grams of Ludox is added and (contains 40 weight %SiO2), dimethyl dichloro
6.5 grams of silane, the material proportion (mol ratio) of reactant is：
SiO2/Al2O3=100
NaOH/Al2O3=0.05
Dimethyldichlorosilane/SiO2=0.05
Hexamethylene imine/SiO2=0.35
H2O/SiO2=20
After question response mixture stirs, it is fitted into stainless steel cauldron, it is small in 150 DEG C of crystallization 55 under agitation
When.Through filtering, washing, dry after taking-up.SiO is obtained through chemical analysis2/Al2O3Mol ratio is 42.3.
Dried sample after measured, its Si29There is nuclear magnetic resonance spectral peak in -18.4ppm in NMR solid cores magnetic spectrum.Its X-
Ray diffraction data is shown in Table 1.
Table 1
The powder sample of 50 grams of synthesis is taken, 550 DEG C are calcined 5 hours, are then exchanged 3 times with 1M nitric acid, filter, dry.
Afterwards, it is sufficiently mixed with 20 grams of aluminum oxide, adds the strip that 5 (weight) % nitric acid are mediated, extruded moulding is 1.6 × 2 millimeters of Φ
Thing, 120 DEG C of drying, 550 DEG C are calcined 5 hours, are prepared into the catalyst of needs.
Take the Catalyst packing of 10 grams of above-mentioned preparations in fixed bed reactors, then pass to raw material liq.Reaction condition
For：Raw material is diisopropyl naphthalene, weight space velocity=2.0 hour-1, 180 DEG C of reaction temperature, reaction pressure 1.0MPa.
After reaction 200 hours, reaction result is：More than 2,6-DIPN selectivity 35.94%, triisopropyl naphthalene weight
It is 11.61% that component, which accounts for product molar ratio,.The mol ratio of 2,6- diisopropyl naphthalenes and 2,7- diisopropyl naphthalenes is 1.11.
【Embodiment 2】
Sodium aluminate (is contained into 42.0 weight %Al2O3) 6.1 grams and 2.0 grams of sodium hydroxide be dissolved in 180 grams of water, then stirring
Add 6.6 grams of trim,ethylchlorosilane in the case of mixing, 43.0 grams of hexahydropyridine adds 150 grams of Ludox and (contains 40 weight %
SiO2), the material proportion (mol ratio) of reactant is：
SiO2/Al2O3=40
NaOH/Al2O3=0.05
Trim,ethylchlorosilane/SiO2=0.06
Hexahydropyridine/SiO2=0.50
H2O/SiO2=15
After question response mixture stirs, it is fitted into stainless steel cauldron, it is small in 152 DEG C of crystallization 50 under agitation
When.Through filtering, washing, dry after taking-up.SiO is obtained through chemical analysis2/Al2O3Mol ratio is 42.1.
Dried sample after measured, its Si29There is nuclear magnetic resonance spectral peak in 15.2ppm in NMR solid cores magnetic spectrum.Its X- is penetrated
Line diffraction data is shown in Table 2.
Table 2
The powder sample of 50 grams of synthesis is taken, the process for preparing catalyst is led to【Embodiment 1】.10 grams of Catalyst packings are taken solid
In fixed bed reactor, raw material liq is then passed to.Reaction condition is：Raw material is the mixture of isopropyl naphthalene and diisopropyl naphthalene,
The weight ratio of isopropyl naphthalene and diisopropyl naphthalene is 0.5：1, weight space velocity=1.5 hour of diisopropyl naphthalene-1, reaction temperature
230 DEG C, reaction pressure 1.0MPa.
After reaction 200 hours, reaction result is：Diisopropyl naphthalene selectivity 42.56%, triisopropyl naphthalene above heavy constituent
It is 8.69% to account for product molar ratio.The mol ratio of 2,6- diisopropyl naphthalenes and 2,7- diisopropyl naphthalenes is 1.08.
【Embodiment 3】
2.0 grams of 5.1 grams of aluminum oxide and sodium hydroxide are dissolved in 540 grams of water, six methylenes are then added in the case of stirring
42.5 grams of base imines, adds 60 grams of solid oxidation silicon, 3.2 grams of HMDS, the material proportion of reactant (mole
Than) be：
SiO2/Al2O3=20
NaOH/Al2O3=0.05
HMDS/SiO2=0.04
Hexamethylene imine/SiO2=0.50
H2O/SiO2=30
After question response mixture stirs, it is fitted into stainless steel cauldron, it is small in 163 DEG C of crystallization 50 under agitation
When.Through filtering, washing, dry after taking-up.SiO is obtained through chemical analysis2/Al2O3Mol ratio is 17.7.
Dried sample after measured, its Si29There is nuclear magnetic resonance spectral peak in 15.8ppm in NMR solid cores magnetic spectrum.Its X- is penetrated
Line diffraction data is shown in Table 3.
Table 3
The powder sample of 50 grams of synthesis is taken, the process for preparing catalyst is led to【Embodiment 1】.10 grams of Catalyst packings are taken solid
In fixed bed reactor, raw material liq is then passed to.Reaction condition is：Raw material is the mixture of isopropyl naphthalene and diisopropyl naphthalene,
The weight ratio of isopropyl naphthalene and diisopropyl naphthalene is 1：1, weight space velocity=1.0 hour of diisopropyl naphthalene-1, reaction temperature 240
DEG C, reaction pressure 1.0MPa.
After reaction 200 hours, reaction result is：Diisopropyl naphthalene selectivity 40.66%, triisopropyl naphthalene above heavy constituent
It is 8.47% to account for product molar ratio.The mol ratio of 2,6- diisopropyl naphthalenes and 2,7- diisopropyl naphthalenes is 1.06.
【Embodiment 4】
Sodium aluminate (is contained into 42.0 weight %Al2O3) 3.0 grams and 4.0 grams of sodium hydroxide be dissolved in 720 grams of water, then stirring
Add 29.8 grams of hexamethylene imine in the case of mixing, add 60 grams of solid oxidation silicon, 6.5 grams of dimethyldichlorosilane, reaction
The material proportion (mol ratio) of thing is：
SiO2/Al2O3=80
NaOH/Al2O3=0.1
Dimethyldichlorosilane/SiO2=0.05
Hexamethylene imine/SiO2=0.35
H2O/SiO2=40
After question response mixture stirs, it is fitted into stainless steel cauldron, it is small in 144 DEG C of crystallization 40 under agitation
When.Through filtering, washing, dry after taking-up.SiO is obtained through chemical analysis2/Al2O3Mol ratio is 79.0.
Dried sample after measured, its Si29There is nuclear magnetic resonance spectral peak in 16.8ppm in NMR solid cores magnetic spectrum.Its X- is penetrated
Line diffraction data is shown in Table 4.
Table 4
The powder sample of 50 grams of synthesis is taken, the process for preparing catalyst is led to【Embodiment 1】.10 grams of Catalyst packings are taken solid
In fixed bed reactor, raw material liq is then passed to.Reaction condition is：Raw material is the mixture of isopropyl naphthalene and diisopropyl naphthalene,
The weight ratio of isopropyl naphthalene and diisopropyl naphthalene is 1.5：1, weight space velocity=0.6 hour of diisopropyl naphthalene-1, reaction temperature
250 DEG C, reaction pressure 1.0MPa.
After reaction 200 hours, reaction result is：Diisopropyl naphthalene selectivity 40.16%, triisopropyl naphthalene above heavy constituent
It is 7.40% to account for product molar ratio.The mol ratio of 2,6- diisopropyl naphthalenes and 2,7- diisopropyl naphthalenes is 1.07.
【Embodiment 5】
Sodium aluminate (is contained into 42.0 weight %Al2O3) 2.0 grams and 20.0 grams of sodium hydroxide be dissolved in 810 grams of water, then stirring
In the case of mixing plus 42.5 grams of hexamethylene imine, 60 grams of solid oxidation silicon is added, 19.8 grams of trimethoxy-benzene base silane, instead
The material proportion (mol ratio) for answering thing is：
SiO2/Al2O3=120
NaOH/Al2O3=0.5
Trimethoxy-benzene base silane/SiO2=0.1
Hexamethylene imine/SiO2=0.5
H2O/SiO2=45
After question response mixture stirs, it is fitted into stainless steel cauldron, it is small in 141 DEG C of crystallization 40 under agitation
When.Through filtering, washing, dry after taking-up.SiO is obtained through chemical analysis2/Al2O3Mol ratio is 117.2.
Dried sample after measured, its Si29There is nuclear magnetic resonance spectral peak in -15.7ppm in NMR solid cores magnetic spectrum.Its X-
Ray diffraction data is shown in Table 5.
Table 5
The powder sample of 50 grams of synthesis is taken, the process for preparing catalyst is led to【Embodiment 1】.10 grams of Catalyst packings are taken solid
In fixed bed reactor, raw material liq is then passed to.Reaction condition is：Raw material is the mixture of isopropyl naphthalene and diisopropyl naphthalene,
The weight ratio of isopropyl naphthalene and diisopropyl naphthalene is 2：1, weight space velocity=0.5 hour of diisopropyl naphthalene-1, reaction temperature 220
DEG C, reaction pressure 1.0MPa.
After reaction 200 hours, reaction result is：Diisopropyl naphthalene selectivity 40.23%, triisopropyl naphthalene above heavy constituent
It is 6.52% to account for product molar ratio.The mol ratio of 2,6- diisopropyl naphthalenes and 2,7- diisopropyl naphthalenes is 1.06.
【Embodiment 6】
Sodium aluminate (is contained into 42.0 weight %Al2O3) 1.0 grams and 12.0 grams of sodium hydroxide be dissolved in 1080 grams of water, Ran Hou
In the case of stirring plus 42.5 grams of hexamethylene imine, 60 grams of solid oxidation silicon is added, 48.5 grams of divinyldichlorosilane,
The material proportion (mol ratio) of reactant is：
SiO2/Al2O3=240
NaOH/Al2O3=0.3
Divinyldichlorosilane/SiO2=0.3
Hexamethylene imine/SiO2=0.5
H2O/SiO2=60
After question response mixture stirs, it is fitted into stainless steel cauldron, it is small in 138 DEG C of crystallization 40 under agitation
When.Through filtering, washing, dry after taking-up.SiO is obtained through chemical analysis2/Al2O3Mol ratio is 221.8.
Dried sample after measured, its Si29There is nuclear magnetic resonance spectral peak in -43.8ppm in NMR solid cores magnetic spectrum.Its X-
Ray diffraction data is shown in Table 6.
Table 6
The powder sample of 50 grams of synthesis is taken, the process for preparing catalyst is led to【Embodiment 1】.10 grams of Catalyst packings are taken solid
In fixed bed reactor, raw material liq is then passed to.Reaction condition is：Raw material is the mixture of isopropyl naphthalene and diisopropyl naphthalene,
The weight ratio of isopropyl naphthalene and diisopropyl naphthalene is 0.75：1, weight space velocity=1.2 hour of diisopropyl naphthalene-1, reaction temperature
230 DEG C, reaction pressure 1.0MPa.
After reaction 200 hours, reaction result is：Diisopropyl naphthalene selectivity 41.37%, triisopropyl naphthalene above heavy constituent
It is 6.81% to account for product molar ratio.The mol ratio of 2,6- diisopropyl naphthalenes and 2,7- diisopropyl naphthalenes is 1.06.
Claims (8)
1. a kind of method for producing 2,6-DIPN, with the mixed of diisopropyl naphthalene or isopropyl naphthalene and diisopropyl naphthalene
Compound is raw material, is 150~300 DEG C in reaction temperature, and the weight space velocity of diisopropyl naphthalene is 0.1~10 hour-1, isopropyl naphthalene
It is that under conditions of 0~4, reaction raw materials are contacted with catalyst, generation 2,6-DIPN with the weight ratio of diisopropyl naphthalene；Institute
State catalyst includes following components by weight percentage：
A) 50~80% organic silicone zeolite；
B) 20~50% binding agent；
Organic silicone zeolite includes the composition of following molar relationship：(1/n)Al2O3：SiO2：(m/n) n=10 in R, formula~
350, m=0.02~50, R are at least one of alkyl, alkane alkenyl or phenyl；The Si of organic silicone zeolite29NMR solid cores
Magnetic chart spectrum is comprised at least between -80~+50ppm a Si29Nuclear magnetic resonance spectral peak；The X-ray of organic silicone zeolite is spread out
Collection of illustrative plates is penetrated 13.2 ± 0.2,12.3 ± 0.1,10.9 ± 0.3,9.1 ± 0.3,6.8 ± 0.2,6.1 ± 0.2,5.6 ± 0.2,4.4
There are d- spacing maximums at ± 0.3,4.0 ± 0.3,3.6 ± 0.2,3.4 ± 0.1 and 3.3 ± 0.2 angstroms.
2. the method for being used to produce 2,6-DIPN according to claim 1, it is characterised in that n=20~150, m=
0.1~20.
3. the method for being used to produce 2,6-DIPN according to claim 1, it is characterised in that the alkyl is that carbon is former
Subnumber is 1~8 alkyl, and the alkane alkenyl is the alkane alkenyl that carbon number is 2~10.
4. the method for being used to produce 2,6-DIPN according to claim 3, it is characterised in that the alkyl is methyl
Or ethyl, the alkane alkenyl is vinyl.
5. the method for being used to produce 2,6-DIPN according to claim 1, it is characterised in that the binding agent is selected from
At least one of aluminum oxide, titanium oxide, zinc oxide or zirconium oxide.
6. according to claim 1 be used for produce 2,6-DIPN method, it is characterised in that reaction temperature be 150~
270℃。
7. the method for being used to produce 2,6-DIPN according to claim 1, it is characterised in that the weight of diisopropyl naphthalene
It is 0.1~2 hour to measure air speed-1。
8. the method for being used to produce 2,6-DIPN according to claim 1, it is characterised in that isopropyl naphthalene is different with two
The weight ratio of propyl group naphthalene is 0.5~3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410314465.4A CN105237328B (en) | 2014-07-03 | 2014-07-03 | Method for producing 2,6 diisopropyl naphthalenes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410314465.4A CN105237328B (en) | 2014-07-03 | 2014-07-03 | Method for producing 2,6 diisopropyl naphthalenes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105237328A CN105237328A (en) | 2016-01-13 |
| CN105237328B true CN105237328B (en) | 2017-09-26 |
Family
ID=55035205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410314465.4A Active CN105237328B (en) | 2014-07-03 | 2014-07-03 | Method for producing 2,6 diisopropyl naphthalenes |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105237328B (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4950824A (en) * | 1988-09-26 | 1990-08-21 | Chiyoda Corporation | Process for the production of 2,6-diisopropylnaphthalene |
| US5026942A (en) * | 1988-10-05 | 1991-06-25 | Catalytica, Inc. | Process for selective diisopropylation of naphthyl compounds using shape selective acidic crystalline molecular sieve catalysts |
| CN101239728A (en) * | 2007-02-07 | 2008-08-13 | 中国石油化工股份有限公司 | Micro-pore zeolite, preparation method and application thereof |
| CN103664494A (en) * | 2012-09-05 | 2014-03-26 | 中国石油化工股份有限公司 | Naphthalene and propylene liquid-phase alkylation method |
-
2014
- 2014-07-03 CN CN201410314465.4A patent/CN105237328B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4950824A (en) * | 1988-09-26 | 1990-08-21 | Chiyoda Corporation | Process for the production of 2,6-diisopropylnaphthalene |
| US5026942A (en) * | 1988-10-05 | 1991-06-25 | Catalytica, Inc. | Process for selective diisopropylation of naphthyl compounds using shape selective acidic crystalline molecular sieve catalysts |
| CN101239728A (en) * | 2007-02-07 | 2008-08-13 | 中国石油化工股份有限公司 | Micro-pore zeolite, preparation method and application thereof |
| CN103664494A (en) * | 2012-09-05 | 2014-03-26 | 中国石油化工股份有限公司 | Naphthalene and propylene liquid-phase alkylation method |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105237328A (en) | 2016-01-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104511271B (en) | A kind of molecular sieve, its manufacture method and its application | |
| CN105217651B (en) | Si-Al molecular sieve SCM 6, its preparation method and use | |
| CN101172254B (en) | Organosilicon micropore zeolite, synthesizing method and uses thereof | |
| CN100554156C (en) | Organic silicon micro-pore zeolite, synthetic method and application thereof | |
| CN101239728B (en) | Micro-pore zeolite, preparation method and application thereof | |
| CN103664494B (en) | The method of naphthalene and propylene liquid-phase alkylation | |
| CN104923293B (en) | Orthoresol isomerization catalyst, its preparation method and the method that M-and P-cresols is catalyzed and synthesized using it | |
| US7494951B2 (en) | Process for the manufacture of catalysts used for producing para-xylene by toluene shape selective alkylation | |
| CN105439802B (en) | The method that hydroalkylation prepares cyclohexyl benzene | |
| CN103958411A (en) | Synthesis of high activity large crystal ZSM-5 | |
| CN105367371B (en) | The method of liquid-phase alkylation cyclohexyl benzene | |
| CN107021504B (en) | A kind of preparation method of mesoporous IM-5 molecular sieve | |
| CN108569944A (en) | The production method of branched alkylbenzene | |
| CN105237328B (en) | Method for producing 2,6 diisopropyl naphthalenes | |
| CN105272816B (en) | Method for isopropyl naphthalene disproportionated reaction | |
| DK159844B (en) | ZEOLIT EU-12 AND PROCEDURE FOR ITS MANUFACTURING | |
| CN101239726B (en) | Organic silicon micro-pore zeolite and its synthetic method and application | |
| CN105272801B (en) | Method for transalkylation reaction | |
| CN105218295B (en) | Prepare the method rich in 2,6 diisopropyl naphthalene compounds | |
| CN105294378B (en) | The production method of diisopropyl naphthalene | |
| JP2010155759A (en) | Method for synthesizing mesoporous aluminosilicate | |
| CN108569945A (en) | The production method of linear alkyl benzene | |
| CN101279885B (en) | Method for iquid-phase alkylation of benzene and N-butene | |
| CN105272802B (en) | The method that isopropyl naphthalene disproportionated reaction prepares diisopropyl naphthalene | |
| CN101279878B (en) | Method for preparing ethylene and propylene by benzin naphtha catalytic pyrolysis |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |