CN103664595B - Ether ester compound and application thereof - Google Patents

Ether ester compound and application thereof Download PDF

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CN103664595B
CN103664595B CN201210328706.1A CN201210328706A CN103664595B CN 103664595 B CN103664595 B CN 103664595B CN 201210328706 A CN201210328706 A CN 201210328706A CN 103664595 B CN103664595 B CN 103664595B
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dme
diethyl ether
oxygen carbonyl
ammediol
propionyloxy
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CN103664595A (en
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胡建军
刘海涛
高明智
马吉星
蔡晓霞
张晓帆
陈建华
马晶
李昌秀
李现忠
王军
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Sinopec Beijing Research Institute of Chemical Industry
China Petroleum and Chemical Corp
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Sinopec Beijing Research Institute of Chemical Industry
China Petroleum and Chemical Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/02—Preparation of ethers from oxiranes
    • C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F110/04—Monomers containing three or four carbon atoms
    • C08F110/06—Propene

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention provides an ether ester compound as shown in Formula M, wherein R<1> and R<2> are independently C1-6 alkyl respectively, and n is an integer of 1-8. The ether ester compound can be used for olefine polymerization reaction, e.g. used as an internal electron donor of an olefine polymerization catalyst. According to the invention, the ether ester compound can be prepared from cheap and accessible raw materials; and the preparation method is simple and mild in conditions. The ether ester compound catalyst used in propylene polymerization reaction shows high activity, and the obtained polymer has high isotactic index. The Formula M is shown in the specification.

Description

A kind of ether ester compound and application thereof
Technical field
The present invention relates to a kind of ether ester compound and application thereof, be specifically related to a kind of for the ether ester compound in field of olefin polymerisation and application thereof.
Background technology
The key of polyolefin industry development is the technology of preparing of catalyst for polymerization.The 1950's, Italian professor Natta has found the Ziegler-Natta catalyst (Z-N catalyzer) producing isotatic polypropylene.At present, used in the industrial production polypropylene catalyst is still main with efficient Z-N catalyst body.In catalyst preparing and polymerization process, need to add the lewis base compound being rich in electronics, i.e. electron donor compound.Electron donor compound add the activity and stereoselectivity that can improve catalyzer, control the relative molecular mass and its distribution of polymkeric substance, the properties of optimization of catalysts, thus reach the object of regulation and control polymer performance.According to the difference of feed postition, electron donor compound can be divided into internal electron donor compound and external donor compound.Internal electron donor adds in the preparation process of catalyst solid constituent, and external electron donor adds in olefin polymerization process.
From discovery Z-N catalyzer so far, polypropylene catalyst developed into for the 5th generation from the first-generation.The continuous renewal of catalyzer is regenerated, and has benefited from just employing new electron donor compound.Find the focus that desirable electron donor compound is polypropylene catalyst study on the synthesis always.Wherein, internal electron donor compound plays a part very important on improvement catalyst performance and polymer tacticity.Therefore can say that internal electron donor is the core of polypropylene catalyst.In polypropylene industrial is produced, use the internal electron donor of maximum forth generation catalyzer for aromatic diester compound Bisphthalate at present.General employing n-butyl phthalate (DNBP) and diisobutyl phthalate (DIBP).Catalyst activity containing Bisphthalate compound is not high, and resulting polymers molecular weight distribution is not wide yet, and external electron donor need be coordinated to use the polymkeric substance that just can obtain highly active catalyzer and high isotactic.
The nineties in 20th century, Himont company openly knew clearly class 1, a 3-bis-ethers electron donor compound in Chinese patent CN1041752A.Using the polypropylene that still can obtain high isotactic in the polymerization process containing the catalyzer of 1,3-diether compound without the need to adding external electron donor with high catalytic activity, this reduces the complicacy of reaction system.
But although use the catalyst activity of 1,3-bis-ethers high (be with phthalic ester internal electron donor catalyst activity 2 ~ 4 times), hydrogen response is good, and the relative molecular weight distribution of resulting polymers is narrow.In addition, 1,3-diether compounds carries out O-alkylation by 1,3-glycol of correspondence and makes.The synthesis technique of midbody compound 1, the 3-glycol involved by preparation process is comparatively complicated, and yield is lower.O-alkylation reaction condition is harsh, needs to use highly basic potassium tert.-butoxide or sodium hydride to carry out dehydrogenation, and O-alkylating reagent methyl iodide used belongs to severe poisonous chemicals control category in China simultaneously.
Summary of the invention
For the problems referred to above of the prior art, the invention provides a kind of ether ester compound, and it can be used as the composition of olefin polymerization catalysis to be applied in olefinic polyreaction.The preparation method of this ether ester compound is simple, and reaction conditions is gentle, simple to operate, and cost of material cheaply and easily obtain.
A kind of ether ester compound provided by the invention, its structural formula is such as formula shown in M:
Formula M
Wherein, R 1and R 2for identical or different alkyl, be preferably the alkyl of C1-C6, be more preferably the alkyl of C1-C4, most preferably be methyl or ethyl; N is the integer of 1 ~ 8, is preferably the integer of 1 ~ 5, is more preferably the integer of 1 ~ 3.
Following compounds can be selected from: 2-(2-methoxycarbonyl) acetoxyl group-1,3-PD dme according to ether ester compound of the present invention, 2-(2-ethoxycarbonyl) acetoxyl group-1,3-PD dme, 2-(2-third oxygen carbonyl) acetoxyl group-1,3-PD dme, 2-(2-butyloxycarbonyl) acetoxyl group-1,3-PD dme, 2-(2-butoxy carbonyl) acetoxyl group-1,3-PD dme, 2-(2-isobutyl boc) acetoxyl group-1,3-PD dme, 2-(2-tertbutyloxycarbonyl) acetoxyl group-1,3-PD dme, 2-(2-penta oxygen carbonyl) acetoxyl group-1,3-PD dme, 2-(2-isoamyl oxygen carbonyl) acetoxyl group-1,3-PD dme, 2-(the own oxygen carbonyl of 2-) acetoxyl group-1,3-PD dme, 2-(3-methoxycarbonyl) propionyloxy-1,3-PD dme, 2-(3-ethoxycarbonyl) propionyloxy-1,3-PD dme, 2-(3-third oxygen carbonyl) propionyloxy-1,3-PD dme, 2-(3-butyloxycarbonyl) propionyloxy-1,3-PD dme, 2-(3-butoxy carbonyl) propionyloxy-1,3-PD dme, 2-(3-isobutyl boc) propionyloxy-1,3-PD dme, 2-(3-tertbutyloxycarbonyl) propionyloxy-1,3-PD dme, 2-(3-penta oxygen carbonyl) propionyloxy-1,3-PD dme, 2-(3-isoamyl oxygen carbonyl) propionyloxy-1,3-PD dme, 2-(the own oxygen carbonyl of 3-) propionyloxy-1,3-PD dme, 2-(4-methoxycarbonyl) butyryl acyloxy-1,3-PD dme, 2-(4-ethoxycarbonyl) butyryl acyloxy-1,3-PD dme, 2-(4-third oxygen carbonyl) butyryl acyloxy-1,3-PD dme, 2-(4-butyloxycarbonyl) butyryl acyloxy-1,3-PD dme, 2-(4-butoxy carbonyl) butyryl acyloxy-1,3-PD dme, 2-(4-isobutyl boc) butyryl acyloxy-1,3-PD dme, 2-(4-tertbutyloxycarbonyl) butyryl acyloxy-1,3-PD dme, 2-(4-penta oxygen carbonyl) butyryl acyloxy-1,3-PD dme, 2-(4-isoamyl oxygen carbonyl) butyryl acyloxy-1,3-PD dme, 2-(the own oxygen carbonyl of 4-) butyryl acyloxy-1,3-PD dme, 2-(5-methoxycarbonyl) valeryl Oxy-1, ammediol dme, 2-(5-ethoxycarbonyl) valeryl Oxy-1, ammediol dme, 2-(5-third oxygen carbonyl) valeryl Oxy-1, ammediol dme, 2-(5-butyloxycarbonyl) valeryl Oxy-1, ammediol dme, 2-(5-butoxy carbonyl) valeryl Oxy-1, ammediol dme, 2-(5-isobutyl boc) valeryl Oxy-1, ammediol dme, 2-(5-tertbutyloxycarbonyl) valeryl Oxy-1, ammediol dme, 2-(5-penta oxygen carbonyl) valeryl Oxy-1, ammediol dme, 2-(5-isoamyl oxygen carbonyl) valeryl Oxy-1, ammediol dme, 2-(the own oxygen carbonyl of 5-) valeryl Oxy-1, ammediol dme, 2-(2-methoxycarbonyl) acetoxyl group-1,3-PD diethyl ether, 2-(2-ethoxycarbonyl) acetoxyl group-1,3-PD diethyl ether, 2-(2-third oxygen carbonyl) acetoxyl group-1,3-PD diethyl ether, 2-(2-butyloxycarbonyl) acetoxyl group-1,3-PD diethyl ether, 2-(2-butoxy carbonyl) acetoxyl group-1,3-PD diethyl ether, 2-(2-isobutyl boc) acetoxyl group-1,3-PD diethyl ether, 2-(2-tertbutyloxycarbonyl) acetoxyl group-1,3-PD diethyl ether, 2-(2-penta oxygen carbonyl) acetoxyl group-1,3-PD diethyl ether, 2-(2-isoamyl oxygen carbonyl) acetoxyl group-1,3-PD diethyl ether, 2-(the own oxygen carbonyl of 2-) acetoxyl group-1,3-PD diethyl ether, 2-(3-methoxycarbonyl) propionyloxy-1,3-PD diethyl ether, 2-(3-ethoxycarbonyl) propionyloxy-1,3-PD diethyl ether, 2-(3-third oxygen carbonyl) propionyloxy-1,3-PD diethyl ether, 2-(3-butyloxycarbonyl) propionyloxy-1,3-PD diethyl ether, 2-(3-butoxy carbonyl) propionyloxy-1,3-PD diethyl ether, 2-(3-isobutyl boc) propionyloxy-1,3-PD diethyl ether, 2-(3-tertbutyloxycarbonyl) propionyloxy-1,3-PD diethyl ether, 2-(3-penta oxygen carbonyl) propionyloxy-1,3-PD diethyl ether, 2-(3-isoamyl oxygen carbonyl) propionyloxy-1,3-PD diethyl ether, 2-(the own oxygen carbonyl of 3-) propionyloxy-1,3-PD diethyl ether, 2-(4-methoxycarbonyl) butyryl acyloxy-1,3-PD diethyl ether, 2-(4-ethoxycarbonyl) butyryl acyloxy-1,3-PD diethyl ether, 2-(4-third oxygen carbonyl) butyryl acyloxy-1,3-PD diethyl ether, 2-(4-butyloxycarbonyl) butyryl acyloxy-1,3-PD diethyl ether, 2-(4-butoxy carbonyl) butyryl acyloxy-1,3-PD diethyl ether, 2-(4-isobutyl boc) butyryl acyloxy-1,3-PD diethyl ether, 2-(4-tertbutyloxycarbonyl) butyryl acyloxy-1,3-PD diethyl ether, 2-(4-penta oxygen carbonyl) butyryl acyloxy-1,3-PD diethyl ether, 2-(4-isoamyl oxygen carbonyl) butyryl acyloxy-1,3-PD diethyl ether, 2-(the own oxygen carbonyl of 4-) butyryl acyloxy-1,3-PD diethyl ether, 2-(5-methoxycarbonyl) valeryl Oxy-1, ammediol diethyl ether, 2-(5-ethoxycarbonyl) valeryl Oxy-1, ammediol diethyl ether, 2-(5-third oxygen carbonyl) valeryl Oxy-1, ammediol diethyl ether, 2-(5-butyloxycarbonyl) valeryl Oxy-1, ammediol diethyl ether, 2-(5-butoxy carbonyl) valeryl Oxy-1, ammediol diethyl ether, 2-(5-isobutyl boc) valeryl Oxy-1, ammediol diethyl ether, 2-(5-tertbutyloxycarbonyl) valeryl Oxy-1, ammediol diethyl ether, 2-(5-penta oxygen carbonyl) valeryl Oxy-1, ammediol diethyl ether, 2-(5-isoamyl oxygen carbonyl) valeryl Oxy-1, ammediol diethyl ether or 2-(the own oxygen carbonyl of 5-) valeryl Oxy-1, ammediol diethyl ether etc.
Ether ester compound according to the present invention obtains by following preparation method:
The first step: with excessive low-carbon alcohol for solvent, reacts epoxy chloropropane and low-carbon alcohol under the effect of alkali, obtains 1,3-dialkoxy-2-propyl alcohol;
Second step: 1,3-dialkoxy-2-propyl alcohol of the first step gained and corresponding acyl chlorides are carried out esterification under acid binding agent effect, obtains such as formula the ether ester compound shown in M.
Present invention also offers such as formula the application of the ether ester compound shown in M in olefinic polyreaction.Such as, ether ester compound is used as the composition of olefin polymerization catalysis in the application.Now, ether ester compound serves as the internal electron donor in catalyst solid component of olefin polymerization.Above-mentioned alkene is preferably propylene, namely the invention provides the application of ether ester compound according to the present invention in propylene polymerization, such as using this ether ester compound as catalyst for polymerization of propylene, internal electron donor as Ziegler-Natta catalyst.
Ether ester compound provided by the invention, its structure is simple, introduces diether bond by raw material epoxy chloropropane cheap and easy to get and low-carbon alcohol reaction, then with esterification of acyl chloride and obtaining.Preparation process mild condition, simple to operate, avoid the use of severe poisonous chemicals.
Ether ester compound according to the present invention can be used as novel internal electron donor and is applied in olefin polymerization catalysis, and then is applied in the polyreaction of alkene especially propylene.Use the catalyst for polymerization of propylene of ether ester compound of the present invention to have higher catalytic activity, simultaneously the degree of isotacticity of polymkeric substance that obtains of polyreaction is high.
Embodiment
To be further described the present invention by specific embodiment below, but scope of the present invention is not limited to this.
The preparation of embodiment 1 ether ester compound (1)
The structural formula of ether ester compound (1) is as follows:
Ether ester compound (1) structural formula
The first step: take methyl alcohol as solvent, by epoxy chloropropane and methyl alcohol back flow reaction 6 hours under the effect of sodium hydroxide, obtains 1,3-dimethoxy-2-propyl alcohol.Wherein, by mole dosage, epoxy chloropropane: sodium hydroxide=1:1.05.The consumption of methyl alcohol is the every moles of epichlorohydrin of 0.6L.
Second step: take tetrahydrofuran (THF) as solvent, by 1,3-dimethoxy-2-propyl alcohol of the first step gained and pentanedioic acid diethyl ester acyl chlorides back flow reaction 7 hours under the effect of acid binding agent triethylamine, obtains ether ester compound (1).Wherein, by mole dosage, 1,3-dimethoxy-2-propyl alcohol: pentanedioic acid diethyl ester acyl chlorides: triethylamine=1:1:1.5.The consumption of tetrahydrofuran (THF) is 1.5L every mole 1,3-dimethoxy-2-propyl alcohol.
Then, use 1h NMR confirms the structure of synthesized ether ester compound (1), as follows:
1h NMR (300MHz, CDCl 3, TMS is interior mark, δ/ppm): 5.14-5.18 (m, 1H), 4.13 (q, 2H), 3.53 (d, 4H), 3.36 (s, 6H), 2.35-2.45 (m, 4H), 1.94-1.99 (m, 2H), 1.25 (t, 3H).
The preparation of embodiment 2 ether ester compound (2)
According to the method for embodiment 1, make epoxy chloropropane and R 1for the low-carbon alcohol R of methyl (Me) 1oH and corresponding acyl chloride reaction, generate such as formula the R shown in M 2for the ether ester compound (2) that ethyl (Et), n are 1, and use 1h NMR confirms its structure, refers to table 1.
The preparation of embodiment 3 ether ester compound (3)
According to the method for embodiment 1, make epoxy chloropropane and R 1for the low-carbon alcohol R of methyl (Me) 1oH and corresponding acyl chloride reaction, generate such as formula the R shown in M 2for the ether ester compound (3) that ethyl (Et), n are 2, and use 1h NMR confirms its structure, refers to table 1.
The preparation of embodiment 4 ether ester compound (4)
According to the method for embodiment 1, make epoxy chloropropane and R 1for the low-carbon alcohol R of methyl (Me) 1oH and corresponding acyl chloride reaction, generate such as formula the R shown in M 2for the ether ester compound (4) that methyl (Me), n are 2, and use 1h NMR confirms its structure, refers to table 1.
The preparation of embodiment 5 ether ester compound (5)
According to the method for embodiment 1, make epoxy chloropropane and R 1for the low-carbon alcohol R of ethyl (Et) 1oH and corresponding acyl chloride reaction, generate such as formula the R shown in M 2for the ether ester compound (5) that methyl (Me), n are 2, and use 1h NMR confirms its structure, refers to table 1.
The preparation of embodiment 6 ether ester compound (6)
According to the method for embodiment 1, make epoxy chloropropane and R 1for the low-carbon alcohol R of ethyl (Et) 1oH and corresponding acyl chloride reaction, generate such as formula the R shown in M 2for the ether ester compound (6) that ethyl (Et), n are 1, and use 1h NMR confirms its structure, refers to table 1.
The preparation of embodiment 7 ether ester compound (7)
According to the method for embodiment 1, make epoxy chloropropane and R 1for the low-carbon alcohol R of ethyl (Et) 1oH and corresponding acyl chloride reaction, generate such as formula the R shown in M 2for the ether ester compound (7) that ethyl (Et), n are 3, and use 1h NMR confirms its structure, refers to table 1.
The preparation of embodiment 8 ether ester compound (8)
According to the method for embodiment 1, make epoxy chloropropane and R 1for the low-carbon alcohol R of ethyl (Et) 1oH and corresponding acyl chloride reaction, generate such as formula the R shown in M 2for the ether ester compound (8) that ethyl (Et), n are 2, and use 1h NMR confirms its structure, refers to table 1.
Table 1
The preparation of embodiment 9 catalyst solid constituent
In the reactor of fully replacing through high pure nitrogen, add magnesium chloride 4.8g successively, toluene 95mL, epoxy chloropropane 4mL, tributyl phosphate 12.5mL, be under agitation warming up to 50 DEG C, and maintain 2.5h.Add Tetra hydro Phthalic anhydride 1.4g, continue to maintain 1h.Solution is cooled to less than-25 DEG C, in 1h, drips TiCl 456mL, slowly be warming up to 80 DEG C, in temperature-rise period, separate out solids gradually, add ether ester compound (1) 2-(4-ethoxycarbonyl) butyryl acyloxy-1 of preparation in 6mmol embodiment 1, ammediol dme as internal electron donor, holding temperature 1h.After filtration, wash twice with toluene 70mL respectively, obtain solid sediment.Then toluene 60mL and TiCl is added 440mL, is warmed up to 110 DEG C, maintains 2h, and after venting filtrate, same operation repeats once, then washs three times at 110 DEG C with toluene 70mL respectively, and the time is respectively 10min, then adds hexane 60mL, washes twice, obtains catalyst solid constituent.
Embodiment 10 propylene polymerization
After fully being replaced with nitrogen and propylene respectively by the 250mL there-necked flask of drying, add 100mL heptane, after being heated to 70 DEG C, add a certain amount of AlEt at ambient pressure 3with Cyclohexylmethyldimethoxysilane (CHMMS), make Al/Si=20 (mol ratio), add the catalyst solid constituent of preparation in embodiment 9 at this temperature, reaction 2h, then uses ethanol termination reaction.Resulting polymers absolute ethanol washing, then dry in a vacuum.The activity calculating catalyzer is 195gPP/ (gCat2h), and the isotactic index of polymkeric substance is 97.8%.

Claims (9)

1. an ether ester compound, its structural formula is such as formula shown in M:
Wherein,
R 1and R 2for identical or different C1-C6 alkyl;
N is the integer of 1 ~ 8.
2. ether ester compound according to claim 1, is characterized in that, described alkyl is the alkyl of C1-C4.
3. ether ester compound according to claim 2, is characterized in that, described alkyl is methyl or ethyl.
4. the ether ester compound according to any one of claim 1-3, is characterized in that, n is the integer of 1 ~ 5.
5. ether ester compound according to claim 4, is characterized in that, n is the integer of 1 ~ 3.
6. ether ester compound according to claim 1, is characterized in that, described ether ester compound is selected from following compounds: 2-(2-methoxycarbonyl) acetoxyl group-1,3-PD dme, 2-(2-ethoxycarbonyl) acetoxyl group-1,3-PD dme, 2-(2-third oxygen carbonyl) acetoxyl group-1,3-PD dme, 2-(2-butyloxycarbonyl) acetoxyl group-1,3-PD dme, 2-(2-butoxy carbonyl) acetoxyl group-1,3-PD dme, 2-(2-isobutyl boc) acetoxyl group-1,3-PD dme, 2-(2-tertbutyloxycarbonyl) acetoxyl group-1,3-PD dme, 2-(2-penta oxygen carbonyl) acetoxyl group-1,3-PD dme, 2-(2-isoamyl oxygen carbonyl) acetoxyl group-1,3-PD dme, 2-(the own oxygen carbonyl of 2-) acetoxyl group-1,3-PD dme, 2-(3-methoxycarbonyl) propionyloxy-1,3-PD dme, 2-(3-ethoxycarbonyl) propionyloxy-1,3-PD dme, 2-(3-third oxygen carbonyl) propionyloxy-1,3-PD dme, 2-(3-butyloxycarbonyl) propionyloxy-1,3-PD dme, 2-(3-butoxy carbonyl) propionyloxy-1,3-PD dme, 2-(3-isobutyl boc) propionyloxy-1,3-PD dme, 2-(3-tertbutyloxycarbonyl) propionyloxy-1,3-PD dme, 2-(3-penta oxygen carbonyl) propionyloxy-1,3-PD dme, 2-(3-isoamyl oxygen carbonyl) propionyloxy-1,3-PD dme, 2-(the own oxygen carbonyl of 3-) propionyloxy-1,3-PD dme, 2-(4-methoxycarbonyl) butyryl acyloxy-1,3-PD dme, 2-(4-ethoxycarbonyl) butyryl acyloxy-1,3-PD dme, 2-(4-third oxygen carbonyl) butyryl acyloxy-1,3-PD dme, 2-(4-butyloxycarbonyl) butyryl acyloxy-1,3-PD dme, 2-(4-butoxy carbonyl) butyryl acyloxy-1,3-PD dme, 2-(4-isobutyl boc) butyryl acyloxy-1,3-PD dme, 2-(4-tertbutyloxycarbonyl) butyryl acyloxy-1,3-PD dme, 2-(4-penta oxygen carbonyl) butyryl acyloxy-1,3-PD dme, 2-(4-isoamyl oxygen carbonyl) butyryl acyloxy-1,3-PD dme, 2-(the own oxygen carbonyl of 4-) butyryl acyloxy-1,3-PD dme, 2-(5-methoxycarbonyl) valeryl Oxy-1, ammediol dme, 2-(5-ethoxycarbonyl) valeryl Oxy-1, ammediol dme, 2-(5-third oxygen carbonyl) valeryl Oxy-1, ammediol dme, 2-(5-butyloxycarbonyl) valeryl Oxy-1, ammediol dme, 2-(5-butoxy carbonyl) valeryl Oxy-1, ammediol dme, 2-(5-isobutyl boc) valeryl Oxy-1, ammediol dme, 2-(5-tertbutyloxycarbonyl) valeryl Oxy-1, ammediol dme, 2-(5-penta oxygen carbonyl) valeryl Oxy-1, ammediol dme, 2-(5-isoamyl oxygen carbonyl) valeryl Oxy-1, ammediol dme, 2-(the own oxygen carbonyl of 5-) valeryl Oxy-1, ammediol dme, 2-(2-methoxycarbonyl) acetoxyl group-1,3-PD diethyl ether, 2-(2-ethoxycarbonyl) acetoxyl group-1,3-PD diethyl ether, 2-(2-third oxygen carbonyl) acetoxyl group-1,3-PD diethyl ether, 2-(2-butyloxycarbonyl) acetoxyl group-1,3-PD diethyl ether, 2-(2-butoxy carbonyl) acetoxyl group-1,3-PD diethyl ether, 2-(2-isobutyl boc) acetoxyl group-1,3-PD diethyl ether, 2-(2-tertbutyloxycarbonyl) acetoxyl group-1,3-PD diethyl ether, 2-(2-penta oxygen carbonyl) acetoxyl group-1,3-PD diethyl ether, 2-(2-isoamyl oxygen carbonyl) acetoxyl group-1,3-PD diethyl ether, 2-(the own oxygen carbonyl of 2-) acetoxyl group-1,3-PD diethyl ether, 2-(3-methoxycarbonyl) propionyloxy-1,3-PD diethyl ether, 2-(3-ethoxycarbonyl) propionyloxy-1,3-PD diethyl ether, 2-(3-third oxygen carbonyl) propionyloxy-1,3-PD diethyl ether, 2-(3-butyloxycarbonyl) propionyloxy-1,3-PD diethyl ether, 2-(3-butoxy carbonyl) propionyloxy-1,3-PD diethyl ether, 2-(3-isobutyl boc) propionyloxy-1,3-PD diethyl ether, 2-(3-tertbutyloxycarbonyl) propionyloxy-1,3-PD diethyl ether, 2-(3-penta oxygen carbonyl) propionyloxy-1,3-PD diethyl ether, 2-(3-isoamyl oxygen carbonyl) propionyloxy-1,3-PD diethyl ether, 2-(the own oxygen carbonyl of 3-) propionyloxy-1,3-PD diethyl ether, 2-(4-methoxycarbonyl) butyryl acyloxy-1,3-PD diethyl ether, 2-(4-ethoxycarbonyl) butyryl acyloxy-1,3-PD diethyl ether, 2-(4-third oxygen carbonyl) butyryl acyloxy-1,3-PD diethyl ether, 2-(4-butyloxycarbonyl) butyryl acyloxy-1,3-PD diethyl ether, 2-(4-butoxy carbonyl) butyryl acyloxy-1,3-PD diethyl ether, 2-(4-isobutyl boc) butyryl acyloxy-1,3-PD diethyl ether, 2-(4-tertbutyloxycarbonyl) butyryl acyloxy-1,3-PD diethyl ether, 2-(4-penta oxygen carbonyl) butyryl acyloxy-1,3-PD diethyl ether, 2-(4-isoamyl oxygen carbonyl) butyryl acyloxy-1,3-PD diethyl ether, 2-(the own oxygen carbonyl of 4-) butyryl acyloxy-1,3-PD diethyl ether, 2-(5-methoxycarbonyl) valeryl Oxy-1, ammediol diethyl ether, 2-(5-ethoxycarbonyl) valeryl Oxy-1, ammediol diethyl ether, 2-(5-third oxygen carbonyl) valeryl Oxy-1, ammediol diethyl ether, 2-(5-butyloxycarbonyl) valeryl Oxy-1, ammediol diethyl ether, 2-(5-butoxy carbonyl) valeryl Oxy-1, ammediol diethyl ether, 2-(5-isobutyl boc) valeryl Oxy-1, ammediol diethyl ether, 2-(5-tertbutyloxycarbonyl) valeryl Oxy-1, ammediol diethyl ether, 2-(5-penta oxygen carbonyl) valeryl Oxy-1, ammediol diethyl ether, 2-(5-isoamyl oxygen carbonyl) valeryl Oxy-1, ammediol diethyl ether or 2-(the own oxygen carbonyl of 5-) valeryl Oxy-1, ammediol diethyl ether.
7. the application of the ether ester compound according to any one of claim 1-6 in olefinic polyreaction.
8. application according to claim 7, is characterized in that, ether ester compound is used as the composition of olefin polymerization catalysis in the application.
9. the application according to claim 7 or 8, is characterized in that, described alkene is propylene.
CN201210328706.1A 2012-09-06 2012-09-06 Ether ester compound and application thereof Active CN103664595B (en)

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