CN107879871A - The preparation method of α-methylstyrene cyclodimerization body - Google Patents
The preparation method of α-methylstyrene cyclodimerization body Download PDFInfo
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- CN107879871A CN107879871A CN201711214912.9A CN201711214912A CN107879871A CN 107879871 A CN107879871 A CN 107879871A CN 201711214912 A CN201711214912 A CN 201711214912A CN 107879871 A CN107879871 A CN 107879871A
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- methylstyrene
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- cyclodimerization body
- cyclodimerization
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- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000006074 cyclodimerization reaction Methods 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 238000001816 cooling Methods 0.000 claims abstract description 10
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 6
- 230000000977 initiatory effect Effects 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003999 initiator Substances 0.000 claims abstract description 5
- 229910052751 metal Inorganic materials 0.000 claims abstract description 5
- 239000002184 metal Substances 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 239000012535 impurity Substances 0.000 claims description 5
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 3
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 2
- 150000002900 organolithium compounds Chemical class 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 150000002642 lithium compounds Chemical class 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000004140 cleaning Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000011964 heteropoly acid Substances 0.000 description 4
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000006471 dimerization reaction Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- -1 aliphatic diol class compound Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000012869 ethanol precipitation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000012690 ionic polymerization Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920003251 poly(α-methylstyrene) Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003026 anti-oxygenic effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910001570 bauxite Inorganic materials 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
Classifications
-
- 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
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/42—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons homo- or co-oligomerisation with ring formation, not being a Diels-Alder conversion
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to polymeric material field, there is provided a kind of new method for preparing α-methylstyrene cyclodimerization body, this method comprise the following steps successively：(1) solution preparation step, the solution contain α-methylstyrene monomer and a kind of aprotic solvent, and the solution preparation step also includes removing water the solution cleaning；(2) cooling step, the solution obtained in step (1) is cool below to 0 DEG C of temperature；(3) the initiation step of polymerisation, including organic metal initiator is added into the solution after the cooling obtained in step (2)；(4) step is terminated, including a kind of proton solvent is added into the solution obtained in step (3).Method provided by the invention can realize the controlledly synthesis of α-methylstyrene cyclodimerization body, and the selectivity of purpose product is high, yield is high.
Description
The invention belongs to polymeric material field, is related to the method that one kind prepares poly- (α-methylstyrene), more specifically
It is related to a kind of preparation method of α-methylstyrene cyclodimerization body.
Background technology
α-methylstyrene cyclodimerization body, chemical name 1,1,3- trimethyl -3- phenyl indans, structural formula such as following formula
(I) shown in.Because the methyl in α-methylstyrene cyclodimerization body molecular structure makes phenyl ring produce induced dipole, itself and many height
Molecular material has good compatibility；Because forming indane ring structure, not degradable, its heat endurance and antioxygenic property are good
It is good.Therefore, α-methylstyrene cyclodimerization body has very extensive purposes in high polymer material, such as lubricant, prevents
Shake conveying medium of agent, heat transfer medium, plasticizer and processing aid, spicy filler, electronics industry inorganic ions etc..
The production method of α-methylstyrene dimer can be roughly divided into two major classes：Ionic polymerization type and polycomplexation mould assembly.
Ionic polymerization can be divided into cationic polymerization and anionic polymerisation again.Wherein, cationic poly is combined into α-methylstyrene dimer
Most, most ripe method in known method, also referred to as acidic catalyst are reacted.The acidic catalyst used has：It is inorganic
Acidic catalyst, such as：Sulfuric acid, phosphoric acid etc.；Organic acid catalyst, such as：Phenyl ring acid, oxalic acid etc.；Solid acid catalyst, such as：Mars
Carclazyte, resin cation etc..Wherein organic acid, activated bauxite catalyst are conventional for production α-methylstyrene dimer at present
Catalyst.
Two patents of JP57010850B, CN1249733A all refer to carry out Alpha-Methyl benzene second using heteropoly acid catalyst
The dimerization of alkene, oligomerisation reaction.The former directly uses heteropoly acid active component, and such as phosphomolybdic acid, phosphotungstic acid carry out Alpha-Methyl benzene second
The dimerization of alkene.Its feature is：Catalyst amount is few, active height, and reaction speed is fast, but high polymer yield is higher in product, and urges
The separation of agent need to use washing, alkali washing process, the problems such as environmental issue and product colourity, stability be present.The latter is load
Type heteropolyacid catalyst, due to acid strong, the degree of polymerization of uncontrollable polymerisation, product is mainly the high polymer of resin type.
CN1281563C uses carried heteropoly acid class compound and C2-C6The mixture of aliphatic diol class compound is as catalyst
The polymerisation of α-methylstyrene is carried out, catalyst activity is high, and reaction rate is high, but it is low the degree of polymerization to be present, and molecular weight point
The drawbacks of cloth is wider.
The content of the invention
It is an object of the invention to overcome the shortcomings of existing α-methylstyrene dimerization preparation, there is provided Yi Zhongxin
Preparation α-methylstyrene cyclodimerization body method, this method can realize the controlledly synthesis of α-methylstyrene cyclodimerization body,
And the selectivity of purpose product is high, yield is high.
The above-mentioned purpose referred to can be realized and after it have studied description below to art technology by the present invention
Should be obvious other objects of the present invention for personnel, the present invention includes a kind of system of α-methylstyrene cyclodimerization body
Preparation Method, it the described method comprises the following steps：(1) solution preparation step, the solution contain α-methylstyrenemonomer and one
Kind aprotic solvent, the solution preparation step, which includes removing water the solution, to clean；(2) cooling step, will be in step (1)
The obtained solution is cool below 0 DEG C of temperature；(3) the initiation step of polymerisation, including obtained in step (2)
To the cooling after solution in add organic metal initiator；(4) step is terminated, including to obtaining in step (3)
A kind of proton solvent is added in the solution.
Wherein, aprotic solvent described in solution preparation step (1) is tetrahydrofuran, toluene, dioxane or dimethyl
Formamide, preferably tetrahydrofuran.
The cooling step (2) includes the solution obtained in solution preparation step (1) being cooled to -78 DEG C to -10
Within the temperature range of DEG C, preferred range is -78 DEG C -65 DEG C.Such temperature range is in order to advantageously stable subsequent
Trigger the tertiary carbon anions formed in step.
The organic metal initiator is a kind of organo-lithium compound, selected from n-BuLi, s-butyl lithium or tert-butyl lithium
In one or more, preferred tert-butyl lithium.
It is methanol or ethanol to terminate proton solvent described in step (4).
The solution preparation step (1), cooling step (2), the initiation step (3) of polymerisation are in inert gas ring
Carried out in border.Inert gas can be understood as a kind of gas being made up of chemical inertness element, such as argon gas, helium or nitrogen.
The step of also including a separation α-methylstyrene cyclodimerization body after the termination step (4), the separation
The step of α-methylstyrene cyclodimerization body is by that will add ethanol by the reactant mixture that termination step (4) obtain
In, it is concentrated and dried and realizes after then obtained precipitation is dissolved with toluene.
According to the present invention, in foregoing and following description, term " aprotic solvent " is also known as non-protonic solvent, such molten
The autoprotolysis reaction of agent is extremely faint or not from tendency is passed, and proton can not be provided in reaction system.
Term " proton solvent " refers to the solvent that strong hydrogen bond can be formed with anion, and the solvent makes nucleopilic reagent solvent
Change, usually contain-OH ,-NH, such as methanol.
Had the following advantages that according to the method for being used to prepare α-methylstyrene cyclodimerization body of the present invention：Due to it is poly- (α-
Methyl styrene) the degree of polymerization and the amount of initiator, unit concentration etc. it is relevant, can quantify and calculate, thus this method can realize α-
The controlledly synthesis of methyl styrene cyclodimerization body, and the narrow molecular weight distribution of polymer.In addition, the polymerisation is strict anhydrous
Carried out under conditions of anaerobic, it also avoid the influence that the water of trace or oxygen cause molecular weight distribution to broaden.
Brief description of the drawings
Fig. 1 is the process chart of the preparation method of α-methylstyrene cyclodimerization body of the present invention.
Embodiment
Present disclosure is described in detail below in conjunction with embodiment, but protection scope of the present invention not by
Any restrictions herein.
Reagent purification processing
Tetrahydrofuran：Add sodium to flow back, and add benzophenone solution colour is now steamed when being changed into navy blue current.Toluene：：
Add CaH2It is evaporated under reduced pressure, now steams current.α-methylstyrene：Add CaH2It is evaporated under reduced pressure, now steams current.Methanol：Add CaH2Distillation is simultaneously
It is sealed, it is stand-by.
Embodiment 1：Reaction bulb is removed to the impurity such as air and the water vapour in bottle through vacuum-nitrogen in advance, will dissolved with α-
The tetrahydrofuran solution (300mL) of methyl styrene (118g, 1mol) is added by the liquid transfer techniques under anhydrous and oxygen-free
In 500mL reaction bulb, then through vacuum-nitrogen it is swapped out in system the residual air and other gaseous impurities that may introduce.Drop
Temperature adds a certain amount of tert .-butyllithium solution to -78 DEG C, and reaction system becomes laking, and dropwise addition 6mL methanol terminates after reacting 5h
Reaction.Reaction solution is precipitated with absolute ethyl alcohol, again with toluene dissolving ethanol precipitation, 3 times repeatedly, is dried in vacuum overnight, obtains target
Product 108.56g (92%).Product appearance is colourless crystallization body, and fusing point is 51-52 DEG C.
Embodiment 2：Reaction bulb is removed to the impurity such as air and the water vapour in bottle through vacuum-nitrogen in advance, will dissolved with α-
The toluene solution (300mL) of methyl styrene (118g, 1mol) adds 500mL's by the liquid transfer techniques under anhydrous and oxygen-free
In reaction bulb, then through vacuum-nitrogen it is swapped out in system the residual air and other gaseous impurities that may introduce.It is cooled to -78
DEG C, a certain amount of Sec-Butyllithium solution is added, reaction system becomes laking, and 6mL methanol terminating reactions are added dropwise after reacting 5h.Will
Reaction solution is precipitated with absolute ethyl alcohol, again with toluene dissolving ethanol precipitation, 3 times repeatedly, is dried in vacuum overnight, is obtained target product
105.18g (89%).Product appearance is colourless crystallization body, and fusing point is 50-52 DEG C.
Claims (11)
1. a kind of preparation method of α-methylstyrene cyclodimerization body, methods described comprise the following steps successively：(1) prepared by solution
Step, the solution contain α-methylstyrenemonomer and a kind of aprotic solvent, and the solution preparation step is also included institute
State solution water removal removal of impurities；(2) cooling step, the solution obtained in step (1) is cool below to 0 DEG C of temperature；(3)
The initiation step of polymerisation, including add organic metal into the solution after the cooling obtained in step (2) and trigger
Agent；(4) step is terminated, including a kind of proton solvent is added into the solution obtained in step (3).
2. a kind of preparation method of α-methylstyrene cyclodimerization body as claimed in claim 1, it is characterised in that prepared by solution
Aprotic solvent described in step (1) is tetrahydrofuran, toluene, dioxane or dimethylformamide.
A kind of 3. preparation method of α-methylstyrene cyclodimerization body as claimed in claim 2, it is characterised in that the non-matter
Sub- solvent is tetrahydrofuran.
A kind of 4. preparation method of α-methylstyrene cyclodimerization body as claimed in claim 1, it is characterised in that the cooling
Step (2) includes the solution obtained in solution preparation step (1) being cooled within the temperature range of -78 DEG C to -10 DEG C.
A kind of 5. preparation method of α-methylstyrene cyclodimerization body as claimed in claim 4, it is characterised in that the temperature
Scope is -78 DEG C to -65 DEG C.
A kind of 6. preparation method of α-methylstyrene cyclodimerization body as claimed in claim 1, it is characterised in that polymerisation
Initiation step (3) described in organic metal initiator be a kind of organo-lithium compound.
7. a kind of preparation method of α-methylstyrene cyclodimerization body as claimed in claim 6, it is characterised in that described organic
Lithium compound is n-BuLi, s-butyl lithium or tert-butyl lithium.
8. a kind of preparation method of α-methylstyrene cyclodimerization body as claimed in claim 7, it is characterised in that described organic
Lithium compound is tert-butyl lithium.
9. a kind of preparation method of α-methylstyrene cyclodimerization body as claimed in claim 1, it is characterised in that terminate step
(4) proton solvent described in is methanol or ethanol.
10. a kind of preparation method of α-methylstyrene cyclodimerization body as claimed in any one of claims 1-9 wherein, its feature exist
In the initiation step (3) of the solution preparation step (1), cooling step (2), polymerisation be to enter in inert gas environment
Capable.
11. a kind of preparation method of α-methylstyrene cyclodimerization body as claimed in claim 10, it is characterised in that described
The step of also including a separation α-methylstyrene cyclodimerization body after termination step (4), the separate alphamethylstyrene
The step of cyclodimerization body is by being added in ethanol by the reactant mixture that termination step (4) obtain, then being obtained
Precipitation dissolved with toluene after be concentrated and dried and realize.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR19980056208A (en) * | 1996-12-28 | 1998-09-25 | 김흥기 | Selective hydrogenation of olefinic double bonds in living polymers |
| CN1541989A (en) * | 2003-11-04 | 2004-11-03 | 华东师范大学 | Catalytic synthesis method of 1,3,3-trimethyl-1-phenyl indan |
| CN1751071A (en) * | 2003-03-31 | 2006-03-22 | 法国原子能委员会 | Method for the preparation of poly (alpha-methylstyrene) |
| CN104058922A (en) * | 2013-03-19 | 2014-09-24 | 北京英力科技发展有限公司 | Synthetic method of 1,1,3-trimethyl-3-phenyl indane |
-
2017
- 2017-11-28 CN CN201711214912.9A patent/CN107879871A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR19980056208A (en) * | 1996-12-28 | 1998-09-25 | 김흥기 | Selective hydrogenation of olefinic double bonds in living polymers |
| CN1751071A (en) * | 2003-03-31 | 2006-03-22 | 法国原子能委员会 | Method for the preparation of poly (alpha-methylstyrene) |
| CN1541989A (en) * | 2003-11-04 | 2004-11-03 | 华东师范大学 | Catalytic synthesis method of 1,3,3-trimethyl-1-phenyl indan |
| CN104058922A (en) * | 2013-03-19 | 2014-09-24 | 北京英力科技发展有限公司 | Synthetic method of 1,1,3-trimethyl-3-phenyl indane |
Non-Patent Citations (1)
| Title |
|---|
| 韦军: "《高分子合成工艺学》", 28 February 2011, 华东理工大学出版社 * |
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