CN114591133A - High-quality acenaphthylene - Google Patents
High-quality acenaphthylene Download PDFInfo
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- CN114591133A CN114591133A CN202011426163.8A CN202011426163A CN114591133A CN 114591133 A CN114591133 A CN 114591133A CN 202011426163 A CN202011426163 A CN 202011426163A CN 114591133 A CN114591133 A CN 114591133A
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- Prior art keywords
- acenaphthylene
- resin
- polyacenaphthylene
- product
- oxygen
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- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 title claims abstract description 105
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 title claims abstract description 99
- 239000011347 resin Substances 0.000 claims abstract description 44
- 229920005989 resin Polymers 0.000 claims abstract description 44
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 29
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 29
- 239000001301 oxygen Substances 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 239000004065 semiconductor Substances 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims abstract description 7
- 238000000921 elemental analysis Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 4
- 238000004817 gas chromatography Methods 0.000 claims description 2
- 238000004811 liquid chromatography Methods 0.000 claims description 2
- 238000004949 mass spectrometry Methods 0.000 claims description 2
- 239000012535 impurity Substances 0.000 abstract description 30
- 238000000034 method Methods 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- 239000012044 organic layer Substances 0.000 description 18
- 239000002994 raw material Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006356 dehydrogenation reaction Methods 0.000 description 9
- 239000011810 insulating material Substances 0.000 description 8
- -1 LCO bicyclic aromatic hydrocarbon Chemical class 0.000 description 7
- 238000011161 development Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- JBXIOAKUBCTDES-UHFFFAOYSA-N 2h-acenaphthylen-1-one Chemical compound C1=CC(C(=O)C2)=C3C2=CC=CC3=C1 JBXIOAKUBCTDES-UHFFFAOYSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 150000002927 oxygen compounds Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910001868 water Inorganic materials 0.000 description 2
- QLLUAUADIMPKIH-UHFFFAOYSA-N 1,2-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=C(C=C)C(C=C)=CC=C21 QLLUAUADIMPKIH-UHFFFAOYSA-N 0.000 description 1
- IYSVFZBXZVPIFA-UHFFFAOYSA-N 1-ethenyl-4-(4-ethenylphenyl)benzene Chemical group C1=CC(C=C)=CC=C1C1=CC=C(C=C)C=C1 IYSVFZBXZVPIFA-UHFFFAOYSA-N 0.000 description 1
- APSUAECGGVKVBU-UHFFFAOYSA-N 1-nitroacenaphthylene Chemical group C1=CC(C([N+](=O)[O-])=C2)=C3C2=CC=CC3=C1 APSUAECGGVKVBU-UHFFFAOYSA-N 0.000 description 1
- 241000209128 Bambusa Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000018997 Growth Hormone Human genes 0.000 description 1
- 108010051696 Growth Hormone Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- AFPRJLBZLPBTPZ-UHFFFAOYSA-N acenaphthoquinone Chemical compound C1=CC(C(C2=O)=O)=C3C2=CC=CC3=C1 AFPRJLBZLPBTPZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000000122 growth hormone Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- ILRLTAZWFOQHRT-UHFFFAOYSA-N potassium;sulfuric acid Chemical compound [K].OS(O)(=O)=O ILRLTAZWFOQHRT-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/14—Purification; Separation; Use of additives by crystallisation; Purification or separation of the crystals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/005—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
-
- 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
- C08F132/00—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F132/08—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
-
- 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
- C08F32/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F32/08—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having two condensed rings
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to high-quality acenaphthylene, which is applied to the field of electronic chemistry, in particular to the field of semiconductor materials. The acenaphthylene provided by the invention does not contain or basically does not contain oxygen-containing compound impurities, and the polyacenaphthylene resin prepared by using the acenaphthylene resin can obtain excellent electrical characteristics, such as the advantage of low relative permittivity.
Description
Technical Field
The invention relates to the field of electronic chemicals, in particular to an insulating material used in the field of semiconductor materials. Specifically, the invention relates to high-quality acenaphthylene, and particularly relates to acenaphthylene applied to the field of electronic chemical products.
Background
Acenaphthylene, also known as dihydroacenaphthylene, the english name Acenaphthylene, CAS number: 208-96-8, the structural formula is as follows:
the acenaphthylene can be used for manufacturing polyacenaphthylene resin, and then used for manufacturing electric insulating materials, ion exchange resins and the like, and can also be directly applied to the field of semiconductor materials. Acenaphthylene can also be used as an organic synthetic raw material to produce 1, 8-naphthalic anhydride, nitro acenaphthylene, acenaphthoquinone and the like for preparing dyes, such as vaseline scarlet and fluorescent whitening agents. The acenaphthylene can also be used for preparing pesticides such as plant growth hormone, insecticides and bactericides.
The following methods are known for the preparation of acenaphthylene:
one is the synthesis of acenaphthylene by acenaphthylene gas-phase oxidation. In a paper "Acenaphthylene" from "j.appl.chem" 1951: the preparation of acenaphthylene and the preparation of acenaphthylene Polymers and Copolymers of acenaphthylene are reported in Its Polymers and Copolymers and in the Patent of Polymers and Copolymers of acenaphthylene (United States Patent: 2445181);
in "the second order journal: nature science, in the 01 th 1959, jiaoyunwei 20736published a paper that catalytic dehydrogenation of coal tar to a combined utilization of ii, acenaphthene describes three catalysts: i, two vanadium pentoxide deposits on pumice, II, zinc oxide, the oxidation magnesium, the oxidation calcium, the mixture of sulfuric acid potassium, chromium acid , the mixture of chromium, III, the mixture of manganese dioxide and alumina. The dehydrogenation of acenaphthene with air as oxidant does not allow obtaining an effect which can be weight-reduced, wherein catalyst I is not suitable for use as a dehydrogenation catalyst. With catalysts II and III, respectively carrying out gas-phase catalytic dehydrogenation of acenaphthene under the condition that water vapor is a dilute agent, the reduction of weight is achieved. In the two catalysts, the JI of the catalyst III is better than a minimum, the optimum reaction temperature is 600 ℃, the yield of the dehydro-products is 90 percent, and the content of acenaphthylene in the catalyst is 96 percent measured by a photoelectric colorimetry.
A method for preparing acenaphthylene is described in a paper published in 1972 of Liaoning chemical industry, namely test success for preparing acenaphthylene by using acenaphthylene, wherein acenaphthylene is gasified and passes through a catalyst under the condition of high temperature, and the catalyst is catalyzed and dehydrogenated to generate the acenaphthylene under the conditions of air and steam respectively; in addition, patent "a method for preparing acenaphthylene and a reaction device thereof" (application number: CN200910054846.2) also reports a method for producing acenaphthylene by gasifying acenaphthylene, passing it through a catalyst, and performing catalytic dehydrogenation in a carbon dioxide atmosphere.
The other is a process for preparing acenaphthylene by rectification extraction. In the invention patent of 'device and method for extracting acenaphthene and acenaphthylene in LCO bicyclic aromatic hydrocarbon' (patent number: CN201811485681.X) published by Gui, Cao Xiao Yan and Ling hong Yu of Nanjing university in 2018, a process for preparing acenaphthylene by rectification extraction method is reported.
The third method is acenaphthene bromination and elimination dehydrogenation. In 1999, a paper "research on dehydrogenation reaction of methylene-containing aromatic hydrocarbons" published by Jiang Ju university in mining industry reported dehydrogenation reactions of various methylene-containing aromatic hydrocarbons in the presence of N-bromosuccinimide (NBS). The method can prepare acenaphthylene by acenaphthylene dehydrogenation.
And the fourth method is a method of bromoaddition and elimination of acenaphthylene. In 2005, taitian koucao and bambusa domestica, new york corporation, patent "method for producing polycyclic aromatic vinyl compound" (patent No. CN200510008106.7) described that a polycyclic aromatic vinyl compound of high purity was produced by adding an addition agent such as halogen, hydrogen halide, and water to a vinyl group of a polycyclic aromatic vinyl compound such as divinylnaphthalene, divinylbiphenyl, or acenaphthylene to give a corresponding polycyclic aromatic vinyl compound derivative, separating and purifying the polycyclic aromatic vinyl compound derivative by recrystallization, adsorption, or chemical reaction, and removing the addition agent added to the polycyclic aromatic vinyl compound derivative.
Researches show that the electrical property indexes of the acenaphthylene and the polyacenaphthylene resin prepared by the method are not ideal when the acenaphthylene and the polyacenaphthylene resin are applied to the field of semiconductors, for example, the prepared polyacenaphthylene resin has high relative permittivity and large dielectric loss, and the application of the polyacenaphthylene resin is influenced. Therefore, there is a need to provide a technical solution to improve the electrical characteristics of the final product to meet the application requirements of the final product in electronic chemical products.
Disclosure of Invention
In order to meet the raw material demand of acenaphthylene in the electronic chemical industry, various methods are attempted to improve the product characteristics, such as adding related additives to acenaphthylene or polyacenaphthylene resin, improving the acenaphthylene polymerization method, and the like. However, the above method is either complicated or the effect is not ideal enough, and thus the method cannot have practical application value in the aspect of industrialization.
The inventor finds out through research that the main reason influencing the electrical characteristics of the product is that the known preparation methods generally generate oxygen-containing impurities in the production process, and the specific impurities are different from other impurities and have significant adverse effects on the electrical characteristics of the product. Thus, the effective removal of the oxygen-containing compound impurities may improve the electrical properties of the polyacenaphthylene resin product or further semiconductor material. Then, the invention provides a high-quality acenaphthylene product, namely an acenaphthylene product containing no or basically no oxygen-containing compound, so that an excellent technical effect is obtained, the use requirement of the high-quality polyacenaphthylene resin is met, and the blank of the product is filled.
The acenaphthylene has the following structure:
there is essentially no requirement in the literature for the impurity content of the acenaphthylene product used, which may contain many different types and amounts of impurities, such as acenaphthylene, biphenyl, dibenzofuran, acenaphthenone, and the like. If not subjected to a particular purification process, it generally contains oxygen-containing compound impurities such as acenaphthenone, dibenzofuran, and the like. The oxygen-containing compound impurities have two main sources, one is introduced from the raw material for preparing acenaphthylene, namely the purity of the raw material is not high, and the raw material contains various oxygen-containing impurities; the other is a by-product in the process of producing acenaphthylene, which may be in a major form such as acenaphthenone, dibenzofuran, etc. The term oxygenate as well as oxygenate impurities, oxygenated impurities or the like in the present invention refers to compounds containing oxygen atoms in the various structures present in the acenaphthylene product.
The polyacenaphthylene resin prepared from acenaphthylene containing oxygen-containing compound impurities has high polarity, high water absorption and other adverse effects, and the reason why the product containing oxygen-containing compounds does not have excellent electrical characteristics may not be determined at present, however, the inventor believes that the defects of the polyacenaphthylene resin may cause high relative permittivity and large dielectric loss, and influence the application of the polyacenaphthylene resin, and the inventor determines through experiments that the acenaphthylene product containing no oxygen-containing compound impurities is the basis for obtaining high-quality polyacenaphthylene resin with excellent electrical characteristics.
By "free or substantially free of oxygenate impurities" herein is meant that the weight percent of the oxygenate is controlled in the range of 0 to 0.1 percent based on the total weight of the product based on the elemental oxygen content of the oxygenate.
The content is determined by various content measuring methods known in the art, such as elemental analysis, gas chromatography, liquid chromatography including high performance liquid chromatography, mass spectrometry, gas chromatography-mass spectrometry, liquid chromatography-mass spectrometry, and the like. Wherein an oxygenate content of 0 represents that the oxygen content in the sample does not reach the limit of detection when said content is determined by one of the known methods described above, or is determined by calculation to not reach the limit of detection. For example, elemental analysis can be used to determine the feed, product, and impurity levels described herein, wherein carbon and hydrogen can be determined by measured or calculated values, oxygen by calculated values, and elemental analysis by% results.
The core of the present application is to remove the oxygen-containing compound impurities as much as possible in the acenaphthylene product, while making no special requirements for other impurities, since this can significantly improve the electrical properties of the polyacenaphthylene resin and subsequent products.
Detailed Description
The raw materials and reagents used in the examples of the invention were as follows:
example 1
1. The raw material acenaphthylene (95%, shihei chemical industry development limited) was analyzed using an elemental analyzer, and the measured value: c94.52, H5.31 (Calculations: C94.53, H5.33, O0.14), where O is represented by a calc because it cannot be directly determined. Adding acenaphthylene (10.2g, 95%, echiei (shanghai) chemical industry development limited) into n-hexane (100mL), heating to 50 ℃, stirring for 10min to completely dissolve the acenaphthylene, adding 50% calcium chloride aqueous solution (50mL multiplied by 3), separating an organic layer by a separating funnel, adding 10% sodium hydroxide aqueous solution (50mL multiplied by 3) into the organic layer, separating an organic layer by the separating funnel, adding deionized water (50mL multiplied by 3) into the organic layer, separating the organic layer by the separating funnel, drying, distilling and concentrating the organic layer by anhydrous magnesium sulfate to (20mL), transferring to a refrigerator at-15 ℃, freezing and crystallizing for 12h, filtering to obtain 7.2g of crystallized acenaphthylene, wherein the yield is 70.6%, and the purity is 98.1%;
2. the product was analyzed using an elemental analyzer, with the measurements: c94.61, H5.33 (calculated: C94.68, H5.32, oxygen content 0);
3. in a 20mL reactor, the acenaphthylene (6.2g) containing no oxygen-containing compound impurities was added, stirred and heated to 110 ℃, and then 2, 2-azobisisobutyronitrile (59mg) was added, stirred and reacted for 1.5h, to obtain polyacenaphthylene resin 1.
4. The polyacenaphthylene resin 1 is prepared into a sheet of 10cm multiplied by 1cm, and the relative permittivity epsilon of the polyacenaphthylene resin 1 is measured at 10GHz according to a recommended method GB/T1409-2006 for measuring the permittivity and the dielectric loss factor of the electric insulating material under power frequency, audio frequency and high frequency (including the wavelength of a meter wave)r＝2.64。
Example 2
1. The raw material acenaphthylene (90%, shanghai alatin biochemistry science and technology, ltd.) was analyzed using an elemental analyzer, and the measured value: c94.28, H5.35 (calculated: C94.29, H5.37, O0.34). Adding acenaphthylene (10.4g, 90%, Shanghai Aladdin Biotechnology, Ltd.) into n-hexane (100mL), stirring and heating to 50 ℃, stirring for 10min, completely dissolving acenaphthylene, adding 50% calcium chloride aqueous solution (50mL multiplied by 3), separating an organic layer by a separating funnel, adding 10% sodium hydroxide aqueous solution (50mL multiplied by 3) into the organic layer, separating an organic layer by the separating funnel, adding deionized water (50mL multiplied by 3) into the organic layer, separating the organic layer by the separating funnel, drying the organic layer by anhydrous magnesium sulfate, distilling and concentrating to 20mL, transferring to a refrigerator at-15 ℃, freezing and crystallizing for 12h, and filtering to obtain 6.8g of crystallized acenaphthylene, wherein the yield is 66.1%, and the purity is 95.5%;
2. the product was analyzed using an elemental analyzer, with the measurements: c94.64, H5.33 (calculated: C94.65, H5.35, oxygen content 0);
3. in a 20mL reactor, the acenaphthylene (6.1g) containing no oxygen-containing compound impurities was added, heated to 110 ℃, and then 2, 2-azobisisobutyronitrile (60mg) was added, and stirred to react for 1.5h, to obtain polyacenaphthylene resin 2.
The polyacenaphthylene resin 2 is prepared into a sheet of 10cm multiplied by 1cm, and the relative permittivity epsilon of the polyacenaphthylene resin 2 is measured at 10GHz according to a recommended method GB/T1409-2006 for measuring the permittivity and the dielectric loss factor of the electric insulating material under power frequency, audio frequency and high frequency (including the wavelength of a meter wave)r＝2.70。
Comparative example 1
1. The raw material acenaphthylene (95%, shihei chemical industry development limited) was analyzed using an elemental analyzer, and the measured value: c94.52, H5.31 (calculated: C94.53, H5.33, O0.14);
2. in a 20mL reactor, acenaphthylene (6.1g, 95%, Chishiea chemical industry development Co., Ltd.) was added, stirred and heated to 110 ℃, and then 2, 2-azobisisobutyronitrile (60mg) was added, stirred and reacted for 1.5 hours, to obtain polyacenaphthylene resin 3.
3. The polyacenaphthylene resin 3 is prepared into a sheet of 10cm multiplied by 1cm, and the relative permittivity epsilon of the polyacenaphthylene resin 3 is measured at 10GHz according to a recommended method GB/T1409-2006 for measuring the permittivity and the dielectric loss factor of the electric insulating material under power frequency, audio frequency and high frequency (including the wavelength of a meter wave)r＝3.06。
Comparative example 2
1. The raw material acenaphthylene (90%, shanghai alatin biochemistry science and technology, ltd.) was analyzed using an elemental analyzer, and the measured value: c94.28, H5.35 (calculated: C94.29, H5.37, O0.34);
2. in a 20mL reactor, acenaphthylene (6.0g, 90%, Shanghai Alatin Biotech Co., Ltd.) was added, stirred and heated to 110 ℃, and 2, 2-azobisisobutyronitrile (59mg) was added, stirred and reacted for 1.5 hours, to obtain polyacenaphthylene resin 4.
3. The polyacenaphthylene resin 4 is prepared into a sheet of 10cm multiplied by 1cm, and the relative permittivity epsilon of the polyacenaphthylene resin 4 is measured at 10GHz according to a recommended method GB/T1409-2006 for measuring the permittivity and the dielectric loss factor of the electric insulating material under power frequency, audio frequency and high frequency (including the wavelength of a meter wave)r＝3.09。
Comparative example 3
1. The raw material acenaphthylene (95%, shihei chemical industry development limited) was analyzed using an elemental analyzer, and the measured value: c94.52, H5.31 (calculated: C94.53, H5.33, O0.14);
2. the raw material acenaphthylene (95%, echiei (shanghai) chemical industry development limited) is purified and prepared by using a simulated moving bed preparation chromatographic system, the purity of the obtained acenaphthylene is 98.9%, the content of impurities is 1.0%, the content of impurities is 0.1%, and the measured value is as follows: c94.58, H5.28 (calculated: C94.60, H5.29, O0.11);
3. in a 20mL reactor, acenaphthylene prepared as described above (6.2g, 99.7%) was added, stirred and heated to 110 deg.C, and 2, 2-azobisisobutyronitrile (59mg) was added, stirred and reacted for 1.5h to obtain polyacenaphthylene resin 5.
4. The polyacenaphthylene resin 5 is prepared into a sheet of 10cm multiplied by 1cm, and the relative permittivity epsilon of the polyacenaphthylene resin 5 is measured at 10GHz according to a recommended method GB/T1409-2006 for measuring the permittivity and the dielectric loss factor of the electric insulating material under power frequency, audio frequency and high frequency (including the wavelength of a meter wave)r＝3.08。
Comparative example 4
1. The raw material acenaphthylene (95%, shihei chemical industry development limited) was analyzed using an elemental analyzer, and the measured value: c94.52, H5.31 (calculated: C94.53, H5.33, O0.14);
2. adding acenaphthylene (10.4g, 95%, echiei (shanghai) chemical industry development limited) into n-hexane (100mL), heating to 50 ℃, stirring for 10min to completely dissolve the acenaphthylene, adding 50% calcium chloride aqueous solution (50mL multiplied by 3), separating an organic layer by a separating funnel, adding 10% sodium hydroxide aqueous solution (50mL multiplied by 3) into the organic layer, separating an organic layer by the separating funnel, adding deionized water (50mL multiplied by 3) into the organic layer, separating the organic layer by the separating funnel, drying, distilling and concentrating the organic layer by anhydrous magnesium sulfate to (20mL), transferring to a refrigerator at-15 ℃, freezing and crystallizing for 12h, and filtering to obtain 6.9g of crystallized acenaphthylene, wherein the yield is 66.3% and the purity is 99.1%;
3. in a 20mL reactor, the acenaphthylene prepared above (5.6g, 99.1%) and dibenzofuran (0.6g, 98%, Shanghai Alatin Biotech Co., Ltd.) were added, stirred and heated to 110 deg.C, and a sample was taken for elemental analysis (measured value: C93.77, H5.27 (calculated value: C93.81, H5.26, O0.93), acenaphthylene content was 89.5%), 2-azobisisobutyronitrile (60mg) was added, and stirred and reacted for 1.5H to obtain polyacenaphthylene resin 6.
4. The polyacenaphthylene resin 6 is prepared into a sheet of 10cm multiplied by 1cm, and the relative permittivity epsilon of the polyacenaphthylene resin 6 is measured at 10GHz according to a recommended method GB/T1409-2006 for measuring the permittivity and the dielectric loss factor of the electric insulating material under power frequency, audio frequency and high frequency (including the wavelength of a meter wave)r＝3.17。
Table 1: summary of the specific embodiments
Through the embodiment of the invention and the proportion, the following can be found:
1. the lower the oxygen content in the acenaphthylene is, the lower the relative permittivity of the prepared polyacenaphthylene resin is, and the polyacenaphthylene resin prepared from acenaphthylene which does not contain oxygen-containing compound impurities has very excellent electronic properties such as relative permittivity and the like;
2. other impurities are removed from the acenaphthylene, for example, the acenaphthylene impurity is reduced to a lower level (0.1%, but still contains oxygenate impurities), and the electronic properties of the prepared polyacenaphthylene resin are not improved; indicating that the content of other impurities is insensitive to the electronic performance of the product of the polyacenaphthylene resin.
3. When the acenaphthylene contains impurities such as dibenzofuran (9.5%, oxygen-containing compound impurities), the electronic performance of the prepared polyacenaphthylene resin is obviously reduced. Therefore, the polyacenaphthylene resin prepared by the oxygen-containing compound impurities in the acenaphthylene has obvious influence on the electronic performance.
On this basis, the patent relates to acenaphthylene products characterized by a low content of oxygen compounds, e.g. 0.1-0 as shown by elemental analysis or other known content determination methods; alternatively 0.1 to 0.001; or 0.05-0.001. The oxygen element compound content of 0 in the present patent refers to a state not detected by the detection device or a case where a trace amount of oxygen is contained, and an absolute content of 0 is not required. Based on this understanding, the elemental oxygen compound content of this patent may also be defined as less than 0.1 to greater than 0.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention. Moreover, the present invention includes the combination of the technical features of the above embodiments in addition to the above embodiments, because after reading the present invention, those skilled in the art can directly and unambiguously determine that the technical features mentioned in the present invention can still solve the related technical problems after being properly combined.
Claims (9)
1. An acenaphthylene product comprising no or substantially no oxygenates, wherein the weight percent of said oxygenates is controlled within the range of 0-0.1% by weight of the total weight of the product based on the oxygen content of the oxygenates.
2. An acenaphthylene product according to claim 1 wherein the oxygen content of the oxygen-containing compound is less than 0.1% to greater than 0% by weight of the total product.
3. The acenaphthylene product of claim 1 wherein the oxygenate content is 0.05% to 0.001%.
4. The acenaphthylene product of claim 1, wherein the oxygen-containing compound content is 0, i.e., no trace oxygen is detected or contains no more than the detection limit.
5. An acenaphthylene product according to claims 1-4 wherein said content is determined by elemental analysis, liquid chromatography, gas chromatography, mass spectrometry or a combination thereof.
6. An acenaphthylene product of claim 1 wherein the relative permittivity of the polyacenaphthylene resin produced using the acenaphthylene is less than 2.80.
7. An acenaphthylene product of claim 6 wherein the relative permittivity of the polyacenaphthylene resin produced using said acenaphthylene is less than 2.70.
8. Use of acenaphthylene in the preparation of a polyacenaphthylene resin having a low relative permittivity, wherein the acenaphthylene is according to any of claims 1-5, the acenaphthylene resin having a relative permittivity of less than 2.80.
9. Use of acenaphthylene in a semiconductor material, wherein said acenaphthylene is as described in any of claims 1-5, first made into an acenaphthylene resin, and then used to prepare a semiconductor material; and the acenaphthylene is directly used for preparing semiconductor materials.
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| CN101177372A (en) * | 2007-12-12 | 2008-05-14 | 卫宏远 | Method for purifying pure acenaphthene |
| CN101955407A (en) * | 2009-07-15 | 2011-01-26 | 华东理工大学 | Preparation method and reaction device of acenaphthylene |
| CN109438164A (en) * | 2018-12-06 | 2019-03-08 | 南京师范大学 | The device and method for extracting acenaphthene and acenaphthylene in LCO double ring arene |
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| JP2002003547A (en) * | 2000-06-26 | 2002-01-09 | Hitachi Chem Co Ltd | Acenaphthylene derivative-containing copolymer, and molding material, sheet or film and optical part obtained by using the same |
| TWI317365B (en) * | 2002-07-31 | 2009-11-21 | Jsr Corp | Acenaphthylene derivative, polymer, and antireflection film-forming composition |
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| CN101177372A (en) * | 2007-12-12 | 2008-05-14 | 卫宏远 | Method for purifying pure acenaphthene |
| CN101955407A (en) * | 2009-07-15 | 2011-01-26 | 华东理工大学 | Preparation method and reaction device of acenaphthylene |
| CN109438164A (en) * | 2018-12-06 | 2019-03-08 | 南京师范大学 | The device and method for extracting acenaphthene and acenaphthylene in LCO double ring arene |
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