CN107827699A - The method that linear alkylbenzene (LAB) is prepared by dimethylbenzene and linear alpha olefin reaction - Google Patents
The method that linear alkylbenzene (LAB) is prepared by dimethylbenzene and linear alpha olefin reaction Download PDFInfo
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- CN107827699A CN107827699A CN201711248936.6A CN201711248936A CN107827699A CN 107827699 A CN107827699 A CN 107827699A CN 201711248936 A CN201711248936 A CN 201711248936A CN 107827699 A CN107827699 A CN 107827699A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
- C07C2/68—Catalytic processes with halides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/10—Chlorides
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract
The present invention relates to the field of chemical synthesis, and in particular to a kind of method for preparing linear alkylbenzene (LAB) by dimethylbenzene and linear alpha olefin reaction.A kind of method that linear alkylbenzene (LAB) is prepared by dimethylbenzene and linear alpha olefin reaction, using the linear alpha olefin containing 8~20 carbon atoms and dimethylbenzene as raw material, aluminum trichloride (anhydrous) is directly added thereto as catalyst, system temperature is kept to be not higher than 30 DEG C during adding, through alkylated reaction, produce, with molar ratio computing, alhpa olefin：Dimethylbenzene：Alchlor=1:3~8:0.01~0.08.The present invention, as catalyst, is obtained the complex catalyst of liquid, can be recycled, reaction system avoids contacting with the external world during use, greatly reduces blowdown, and environmentally friendly, cost is low, and course of reaction is gently easily-controllable using aluminum trichloride (anhydrous).In addition using dimethylbenzene and olefine reaction production alkylbenzene, compared with traditional alkylbenzene, obtained direct-connected alkylbenzene purity is high.
Description
Technical field
The present invention relates to the field of chemical synthesis, and in particular to a kind of to prepare straight chain alkane by dimethylbenzene and linear alpha-alkene reaction
The method of base benzene.
Background technology
Linear alkylbenzene (LAB) is that benzene or be alkylated containing short-chain alkyl benzene with long-chain olefin under catalyst action obtains, and is to close
Into the primary raw material of alkyl benzene sulfonate surfactant.Industrial conventional art is catalyzed using hydrofluoric acid, in process of production
Severe corrosion equipment simultaneously pollutes to environment, and catalyst is difficult to reuse.Non-corrosiveness is developed later, nontoxic is consolidated
Body acid catalyst substitutes hydrofluoric acid, using environment-friendly alkylation process already turns into development trend.Solid acid is corroding
Property with compare hydrofluoric acid in terms of environmental pollution and have clear improvement, but solid acid catalyst still suffers from problems, such as catalyst
Easily inactivation, harsh is required to feed moisture content, single pass life is short, and the alkylated reaction of solid acid and catalyst regeneration need
Want frequent switching.Molecular sieve catalyst is also developed in recent years, and compared to solid acid, its activity is preferably, pollution-free, but stability
Difference, cost are high.
Using aluminum trichloride (anhydrous) as the catalyst of alkylation, it is necessary to additionally add hydrogen chloride gas as co-catalysis
Agent, it is active high the advantages of such a catalyst, cost is low, but generally only produces a large amount of spent acid, post processing cost using once
Height, pollution is produced to environment.
The raw material of linear alkylbenzene (LAB) has alkene and benzene or the alkylbenzene containing short chain, uses dimethylbenzene as raw material, with current city
Benzene or toluene on field used in common allcyl groups benzene is different, on the one hand dimethylbenzene can increase the alkyl carbon number on phenyl ring, experiment
Prove that this method not only solves the carbon chain lengths problem on phenyl ring, and the toxicity of dimethylbenzene makes well below benzene and toluene
Production environment more safety is friendly；Another aspect is that the structure of diformazan benzene molecular can make the alkyl benzene sulphonate molecules of salt finally synthesized
More large area is occupied on oil-water interfaces, so as to be effectively reduced oil water interfacial tension.Due to having substituted on the phenyl ring of dimethylbenzene
Two methyl, the electronic effect that pushes away of methyl cause dimethylbenzene to be easier that electrophilic substitution reaction occurs than benzene.But dimethylbenzene is not
Di reaction easily occurs, because after a chain alkyl is instead of on dimethylbenzene, although the electricity on phenyl ring
Sub- cloud density rise, but at this moment had three substituents on phenyl ring, and one of them is chain alkyl so that electronic effect
Compared with space steric effect, it is major influence factors that space steric effect, which influences, so that the further alkyl on phenyl ring
Change is suppressed.Therefore, benzene/hydrocarbon mol ratio and alkene of the alkene when diformazan benzene alkylation reaction are compared with benzene alkylation reaction
It is greatly lowered.
The content of the invention
The present invention provides a kind of method for preparing linear alkylbenzene (LAB) by dimethylbenzene and linear alpha-alkene reaction, using ring
Border is friendly, and catalyst activity is high, the gentle easily-controllable alkylation process of reaction condition.
The preparation method includes：Using the linear alpha-alkene containing 8~20 carbon atoms and dimethylbenzene as raw material, thereto directly
Connect and add aluminum trichloride (anhydrous) as catalyst, keep system temperature to be not higher than 30 DEG C during adding, through alkylated reaction, i.e.,
, with molar ratio computing, alpha-olefin：Dimethylbenzene：Alchlor=1:3~8:0.01~0.08；Preferably, with molar ratio computing,
The alpha-olefin：Dimethylbenzene：Alchlor=1:3~5:0.05~0.08.
Above-mentioned preparation method, reaction condition is gentle, easy to operate, and suitable for industrialized production, and the purity of products therefrom is very
Height, it can reach more than 99%.
The present invention provides a kind of specific steps of preparation method in the lump, including：
1) using the linear alpha-alkene containing 8~20 carbon atoms and dimethylbenzene as raw material, aluminum trichloride (anhydrous) is catalyst, is thrown
Keep system temperature to be not higher than 30 DEG C during adding, through alkylated reaction, stratification, take upper solution, produce straight chained alkyl
Benzene；
Mol ratio is alpha-olefin：Dimethylbenzene：Alchlor=1:3~8:0.01~0.08；
2) a layer solution is removed, obtains complex compound catalyst；
3) aluminum trichloride (anhydrous) is substituted with the complex compound catalyst, produces linear alkylbenzene (LAB).
Preferably, aluminum trichloride (anhydrous) is substituted with the complex compound catalyst part, the complex compound catalyst is described
The 95~99.5% of catalyst.I.e.：Aluminum trichloride (anhydrous) is substituted with the complex compound catalyst, and supplements aluminum trichloride (anhydrous) weight
Multiple step 1), produces linear alkylbenzene (LAB)；The parts by weight of the supplement aluminum trichloride (anhydrous) are anhydrous tri-chlorination described in step 1)
The 0.5~5% of the parts by weight of aluminium.
On the linear alpha-alkene, it is preferable that selected from 1- octenes, 1- decene, 1- laurylenes, 1-tetradecylene, 1- 16
Alkene, 1- octadecylenes, one kind in 1- icosa alkenes.
On the alkylated reaction, it is preferable that the reaction temperature of the alkylated reaction is 30~80 DEG C；It is further excellent
Selection of land, the reaction time of the alkylated reaction is 3-7h.
Under the conditions of said temperature, alkylated reaction is thorough, does not produce the waste of material, and reaction rate is fast, reaction interval
Degree is preferable.
Preferably, alkali lye is added to the upper solution, regulation pH value is neutrality；It is further preferred that the alkali
Liquid is the solution of inorganic base；Yet further, the inorganic base is one kind of ammoniacal liquor, sodium hydroxide, potassium hydroxide or carbonate.
Above-mentioned preparation method, not only the purity of products therefrom is high, also uses the characteristic of raw material so that catalyst can weigh
It is multiple to utilize, while high stability and catalytic activity are kept, the pollution to environment is reduced, greatly reduces cost, and it is easy to operate,
Production efficiency greatly improves.
Preferably, the present invention provides a kind of side that linear alkylbenzene (LAB) is prepared by dimethylbenzene and linear alpha-alkene reaction
Method.Its step includes：
1) dimethylbenzene being fitted into reactor, adds aluminum trichloride (anhydrous), add alpha-olefin, keeping temperature is less than 30 DEG C,
Charging finishes, and is warming up to 40~80 DEG C, continues 3~7h of reaction.
2) lower floor of step 1) is the complex compound of the formation such as alchlor and hydrogen chloride, dimethylbenzene, is added after separating
A small amount of aluminum trichloride (anhydrous), may be reused.
3) upper strata of step 1) is the thick liquid of alkylbenzene, and containing excessive dimethylbenzene, addition alkali lye adjusts pH value to 7, isolates
Water layer, the thick liquid in upper strata go out excessive dimethylbenzene by vacuum distillation and produce linear alkylbenzene (LAB).
Described linear alpha-alkene is：1- octenes, 1- decene, 1- laurylenes, 1-tetradecylene, 1- hexadecylenes, 1- octadecylenes,
At least one of 1- icosa alkenes.
Described alkali lye includes ammoniacal liquor and inorganic base, and wherein inorganic base is ammoniacal liquor, sodium hydroxide, potassium hydroxide or carbonate
In one kind.
The described complex compound isolated, can be used as catalyst to reuse 5~8 times, need to only supplement starting institute every time
Add the 1%~5% of aluminum trichloride (anhydrous) total amount.
A kind of method for preparing linear alkylbenzene (LAB) by dimethylbenzene and linear alpha-alkene reaction proposed by the present invention, has following
Advantage：
(1) aluminum trichloride (anhydrous) is used as catalyst, it is not necessary to which extra addition dry hydrogen chloride is as co-catalyst, profit
With the denier moisture unavoidably carried in raw material, a small amount of hydrogen chloride gas is generated with alchlor reaction, you can as helping
Catalyst；
(2) after utilizing property of raw material, reaction to terminate, aluminum trichloride (anhydrous) and dimethylbenzene etc. form the complex catalysis of liquid
Agent, catalyst can be used as to reuse, and show very high activity and stability, easily separated from reaction system,
It can recycle, production equipment selects enamel material, and reaction system avoids contacting with the external world during use, greatly
Ground reduces blowdown, and environmentally friendly, cost is low, and course of reaction is gently easily-controllable；
(3) linear alkylbenzene (LAB) is prepared with linear alpha-alkene reaction using dimethylbenzene, compared with traditional alkylbenzene, this technique is several
Di is not produced, without dialkyl benzene, diphenyl alkane, polyalkylbenzene, how completely etc. indane and accessory substance, what is obtained is straight
Even alkylbenzene purity is high.Alpha-olefin conversion ratio can reach more than 99.7%.
Embodiment
Following examples are used to illustrate the present invention, but are not limited to the scope of the present invention.
It is industrial goods that following examples, which use reagent,.
Embodiment 1
The present embodiment provides a kind of method for preparing linear alkylbenzene (LAB) by dimethylbenzene and linear alpha-alkene reaction：
1) 318g dimethylbenzene is fitted into the reactor for carrying agitator, thermometer, stirs the lower addition anhydrous trichlorines of 6.7g
Change aluminium, keeping temperature is not higher than 30 DEG C, and the linear 1- laurylenes of 168g are slowly added dropwise, is added dropwise, is warming up to 45 DEG C, continue to react
3h, stand, layering.Upper strata is the thick liquid of alkylbenzene, and ammoniacal liquor is added dropwise, and adjusts pH to 7, separates water-yielding stratum, the thick liquid in upper strata is by decompression
Excessive dimethylbenzene is distilled out, obtains 272g dimethyl dodecyl base benzene.
2) lower floor is complex compound catalyst, be may be reused.
Liquid chromatographic detection, purity 99.5%.
Embodiment 2
The present embodiment provides a kind of method for preparing linear alkylbenzene (LAB) by dimethylbenzene and linear alpha-alkene reaction：
424g dimethylbenzene is fitted into the reactor for carrying agitator, thermometer, it is (i.e. real to stir lower addition 13g complex compounds
Apply obtained by the step 2) of example 1), and the fresh aluminum trichloride (anhydrous)s of 0.3g are supplemented, keeping temperature is not higher than 30 DEG C, and 168g lines are slowly added dropwise
Property 1- laurylenes, be added dropwise, be warming up to 45 DEG C, continue react 3h, stand, layering.Upper strata is the thick liquid of alkylbenzene, and ammonia is added dropwise
Water, pH to 7 is adjusted, separate water-yielding stratum, the thick liquid in upper strata goes out excessive dimethylbenzene by vacuum distillation, obtains 272g dimethyl 12
Alkylbenzene.
Liquid chromatographic detection, purity 99.3%.
Embodiment 3
The present embodiment provides a kind of method for preparing linear alkylbenzene (LAB) by dimethylbenzene and linear alpha-alkene reaction：
1) 530g dimethylbenzene is fitted into the reactor for carrying agitator, thermometer, stirs the lower addition anhydrous trichlorines of 10.6g
Change aluminium, keeping temperature is not higher than 30 DEG C, and the linear 1- hexadecylenes of 224g are slowly added dropwise, is added dropwise, is warming up to 70 DEG C, continue to react
6h, stand, layering.Upper strata is the thick liquid of alkylbenzene, and sodium hydroxide solution is added dropwise, and adjusts pH to 7, separates water-yielding stratum, the thick liquid in upper strata
Go out excessive dimethylbenzene by vacuum distillation, obtain 327.2g dimethyl hexadecyl base benzene.
2) lower floor is complex compound catalyst, be may be reused.
Liquid chromatographic detection, purity 99.2%.
Embodiment 4
The present embodiment provides a kind of method for preparing linear alkylbenzene (LAB) by dimethylbenzene and linear alpha-alkene reaction：
636g dimethylbenzene is fitted into the reactor for carrying agitator, thermometer, stirs lower addition 21.5g complex compounds (i.e.
Obtained by the step 2) of embodiment 1), and the fresh aluminum trichloride (anhydrous)s of 0.2g are supplemented, keeping temperature is not higher than 30 DEG C, and 224g is slowly added dropwise
Linear 1- hexadecylenes, are added dropwise, are warming up to 65 DEG C, continue to react 5.5h, stand, layering.Upper strata is the thick liquid of alkylbenzene, is added dropwise
Sodium hydroxide solution, pH to 7 is adjusted, separate water-yielding stratum, the thick liquid in upper strata goes out excessive dimethylbenzene by vacuum distillation, obtained
327.6g dimethyl hexadecyl base benzene.
Liquid chromatographic detection, purity 99.5%.
Although above the present invention is made to retouch in detail with general explanation, embodiment and experiment
State, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, are belonged to claimed
Scope.
Claims (10)
- A kind of 1. method that linear alkylbenzene (LAB) is prepared by dimethylbenzene and linear alpha-alkene reaction, it is characterised in that with containing 8~20 The linear alpha-alkene of carbon atom and dimethylbenzene are raw material, directly add aluminum trichloride (anhydrous) thereto as catalyst, add Keep system temperature to be not higher than 30 DEG C in journey, through alkylated reaction, produce；With molar ratio computing, alpha-olefin：Dimethylbenzene：Alchlor=1:3~8:0.01~0.08.
- 2. preparation method according to claim 1, it is characterised in that with molar ratio computing, the alpha-olefin：Dimethylbenzene：Three Aluminium chloride=1:3~5:0.05~0.08.
- 3. preparation method according to claim 1 or 2, it is characterised in that by the system stratification after alkylated reaction；Lower floor's solution is substituted at least partly described aluminum trichloride (anhydrous) as complex compound catalyst to recycle.
- 4. preparation method according to claim 3, it is characterised in that part anhydrous three is substituted with the complex compound catalyst Aluminium chloride, the complex compound catalyst are 95~99.5%, preferably the 95~99% of the catalyst.
- 5. according to the preparation method described in claim any one of 1-4, it is characterised in that the linear alpha-alkene includes：1- is pungent Alkene, 1- decene, 1- laurylenes, 1-tetradecylene, 1- hexadecylenes, 1- octadecylenes, one kind in 1- icosa alkenes.
- 6. according to the preparation method described in claim any one of 1-5, it is characterised in that the reaction temperature of the alkylated reaction For 30~80 DEG C.
- 7. preparation method according to claim 6, it is characterised in that the reaction time of the alkylated reaction is 3-7h.
- 8. according to the preparation method described in claim any one of 3-7, it is characterised in that the system after alkylated reaction is stood Layering, alkali lye is added to upper solution, regulation pH value is neutrality.
- 9. preparation method according to claim 8, it is characterised in that the alkali lye is the solution of inorganic base.
- 10. preparation method according to claim 9, it is characterised in that the inorganic base is ammoniacal liquor, sodium hydroxide, hydrogen-oxygen Change one kind of potassium or carbonate.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111533632A (en) * | 2020-06-02 | 2020-08-14 | 新乡市瑞丰新材料股份有限公司 | Preparation method of high-content monoalkylbenzene |
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| CN111533632A (en) * | 2020-06-02 | 2020-08-14 | 新乡市瑞丰新材料股份有限公司 | Preparation method of high-content monoalkylbenzene |
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Application publication date: 20180323 |