WO2017201964A1 - Copolymère fonctionnel préparé directement à partir d'un mélange d'hydrocarbures supérieurs et procédé pour sa préparation - Google Patents

Copolymère fonctionnel préparé directement à partir d'un mélange d'hydrocarbures supérieurs et procédé pour sa préparation Download PDF

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WO2017201964A1
WO2017201964A1 PCT/CN2016/103475 CN2016103475W WO2017201964A1 WO 2017201964 A1 WO2017201964 A1 WO 2017201964A1 CN 2016103475 W CN2016103475 W CN 2016103475W WO 2017201964 A1 WO2017201964 A1 WO 2017201964A1
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fraction
copolymer
fractions
mah
coal tar
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PCT/CN2016/103475
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Chinese (zh)
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杨万泰
陈延昭
陈冬
王力
马育红
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Beijing University of Chemical Technology
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Beijing University of Chemical Technology
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    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/04—Anhydrides, e.g. cyclic anhydrides
    • C08F222/06—Maleic anhydride
    • C08F222/08—Maleic anhydride with vinyl aromatic monomers
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/04—Polymerisation in solution
    • C08F2/06—Organic solvent
    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/04—Anhydrides, e.g. cyclic anhydrides
    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/04—Anhydrides, e.g. cyclic anhydrides
    • C08F222/06—Maleic anhydride

Definitions

  • the invention belongs to the field of resource application of C8, C9 fraction and coal tar light fraction in petroleum cracking and reforming, and particularly relates to the direct use of these mixture fractions with maleic anhydride (MAH), maleimide and its derivatives, clothing One or several reactions of the anhydride are used to prepare a functional copolymer.
  • MAH maleic anhydride
  • maleimide maleimide
  • clothing One or several reactions of the anhydride are used to prepare a functional copolymer.
  • the C8 and C9 fractions are mainly derived from the steam cracking ethylene process and the naphtha platinum reforming process, and some are derived from toluene disproportionation or transalkylation products and coal tar, etc., and their compositions are shown in Tables 1-4.
  • the C8 fraction mainly contains unsaturated hydrocarbons including styrene, allylbenzene, vinyl toluene, hydrazine, formazan, etc., and further rectification can be carried out to obtain a main component of xylene/ethylbenzene (60%-65). %), a mixture of styrene (about 30%).
  • the C9 fraction is a mixture of C9 aromatics and olefins. There are two main sources: one is reforming C9, mainly from the refinery of the refinery, and the other is from the ethylene production. product. As can be seen from Table 3, the composition of the C9 fractions of different manufacturers is substantially the same.
  • the cracked C 9 fraction contains a large amount of unsaturated hydrocarbons, and its composition is very complicated, and the boiling points are close to each other, which makes it difficult to perform fine separation.
  • the output of ethylene which represents the level of industrial development, has also increased significantly, so the production of C8 and C9 fractions as ethylene by-products has also increased. Therefore, how to effectively utilize high carbon number mixed by-products has become an important issue in the petroleum industry.
  • the light oil component in coal tar mainly contains styrene, ⁇ -methylstyrene, alkylbenzene, vinyltoluene, dicyclopentadiene, benzofuran, anthracene, formazan and methylbenzofuran, etc. Mainly used as a dark-light color coumarone resin raw material.
  • China's C8 fraction is mainly used in the production of para-xylene, blended gasoline and solvents.
  • Paraxylene is the basic raw material for the production of polyester, and unsaturated mixtures such as styrene and derivatives have not been utilized. .
  • the advantage of extracting styrene from pyrolysis gasoline is more obvious, while the C8 fraction contains more styrene, so the C8 extraction styrene technology has received more and more attention.
  • the first step in C8 extraction of styrene is to selectively convert the phenylacetylene in the C8 fraction to styrene through a selective hydrogenation reactor, and then separate the styrene from the other C8 components by extractive rectification. .
  • C8 extraction of styrene has a long process route, which is very difficult in practical operation.
  • First, the relative volatility of styrene and o-xylene in C8 is very small, and second, there is a trace amount of phenylacetylene in styrene.
  • the product styrene is colored for purity reasons.
  • C9 petroleum resin is a thermoplastic resin with a molecular weight of about 300-3000.
  • the production process of C9 petroleum resin mainly includes three methods of catalytic polymerization, free radical initiated polymerization and thermal polymerization, and catalytic polymerization is the most commonly used polymerization method.
  • the polymerization temperature is usually set at about 50 ° C
  • the reaction time is about 1-5 h
  • the reaction temperature and reaction time are not too high.
  • the most widely used catalytic polymerization method in the industry is an acid-catalyzed polymerization process using Lewis acid as a catalyst.
  • the catalytic polymerization process has the advantages of high polymerization speed and mild regulation, but it is easy to generate a large amount of industrial wastewater when the catalyst is removed. It is described in US Pat. No. 6,479,598 that the catalyst is coated on the catalyst support during the catalytic polymerization of the C9 fraction, thereby eliminating catalyst recovery and post-treatment.
  • the production of C9 petroleum resin is complicated, the production line is long, and a large amount of industrial wastewater is easily generated. Therefore, the production rate of C9 petroleum resin has been low, which greatly limits the reuse of C9 fraction resources.
  • Synthesis method of copolymer a method for synthesizing a low molecular weight styrene/maleic anhydride alternating copolymer disclosed in Chinese Patent No. ZL 200910079490.8, the disclosure of which is incorporated herein by reference.
  • a method of alternating copolymers of itaconic anhydride with a styrenic monomer discloses a process for preparing a series of monodisperse polymer microspheres of different sizes and compositions by self-stabilizing precipitation polymerization.
  • a cross-linking structure of monodisperse functional copolymer microspheres can be prepared by adding a crosslinking agent to a self-stabilizing precipitation polymerization system, and a crosslinked structure is disclosed in a series of patents.
  • a method of preparing copolymer microspheres For example, "A Method for Preparing a Crosslinked Maleic Anhydride-Vinyl Acetate Copolymer", which is disclosed in Chinese Patent Application No. 200810118553.1, discloses a crosslinked maleic anhydride-styrene copolymer disclosed in Chinese Patent Application No. 200810118552.7.
  • the object of the present invention is to prepare a copolymer containing a functional group in a one-step reaction using a high carbon number hydrocarbon mixture as a raw material.
  • the C8, C9 fraction and the coal tar light fraction in the petroleum cracking and reforming are directly subjected to copolymerization reaction with one or more of MAH, maleimide and its derivatives, and itaconic anhydride.
  • the functional copolymer is prepared by a stable precipitation polymerization method using a high carbon number hydrocarbon mixture as a raw material.
  • the monomer in the reaction system is composed of an electron donating monomer and an electron accepting monomer, wherein the electron donating monomer is composed of C8 and C9 fractions and Olefins in coal tar light fractions (styrene, allylbenzene, vinyl toluene, hydrazine, formamidine, dihydrodicyclopentadiene, dihydromethyldicyclopentadiene, dihydrodimethyldicyclopentadiene) One or several components of cyclopentadiene, methylcyclopentadiene, methyldicyclopentadiene, ⁇ -methylstyrene, dicyclopentadiene, benzofuran and methylbenzofuran;
  • the electron-accepting monomer is composed of one or more of MAH, maleimide and its derivative, itaconic an
  • the initiator used in the polymerization system is a common oil-soluble free radical initiator well known to those skilled in the art, and may be an azo initiator or a peroxide initiator.
  • the initiator content in the system is 0.05 to 10 wt% of the mass of the monomer. %, preferably 1 to 3 wt%.
  • the azo initiator includes: azobisisobutyronitrile, azobisisoheptanyl, azobisisobutyric acid a methyl ester or the like;
  • the peroxide initiator includes: dibenzoyl peroxide, dicumyl peroxide, bis(2,4-dichlorobenzoyl peroxide), di-tert-butyl peroxide, peroxidation Dodecyl, tert-butyl peroxybenzoate, diisopropyl peroxydicarbonate and dicyclohexyl peroxydicarbonate.
  • the solvent of the polymerization system may be an alkyl acid ester of an organic acid, an aromatic hydrocarbon or a mixed solution of a ketone and an alkane.
  • the structural formula of the organic acid alkyl ester is
  • R 1 is an alkyl group having 1 to 8 carbon atoms, a benzyl group, a phenyl group or a substituted phenyl group
  • R 2 is an alkyl group having 1 to 5 atomic atoms.
  • the organic acid alkyl ester includes ethyl formate, propyl formate, isobutyl formate, amyl formate, ethyl acetate, butyl acetate, isobutyl acetate, amyl acetate, isoamyl acetate, benzyl acetate, acetic acid.
  • Phenyl ester methyl propionate, ethyl propionate, propyl propionate, butyl propionate, methyl butyrate, ethyl butyrate, propyl butyrate, butyl butyrate, isobutyl butyrate, butyl Isoamyl acid ester, ethyl isobutyrate, ethyl isovalerate, isoamyl isovalerate, methyl benzoate, ethyl benzoate, propyl benzoate, butyl benzoate, isoamyl benzoate, An ester solvent such as methyl phenylacetate, ethyl phenylacetate, propyl phenylacetate, butyl phenylacetate or isoamyl phenylacetate; the aromatic hydrocarbon is selected from the group consisting of toluene, xylene, ethylbenzene and the like; and the ketone is mixed with an al
  • the volume fraction of the ketone in the solution is 5%-65%
  • the ketone is selected from the group consisting of acetone, methyl ethyl ketone, cyclohexanone, methyl isobutyl ketone, methyl isopropyl ketone
  • the alkane is selected from the group consisting of n-pentane
  • An alkane solvent such as an alkane, n-hexane, cyclohexane, n-heptane, n-octane or isooctane.
  • the electron-accepting monomer MAH, maleimide and its derivative, one or several of itaconic anhydride and the initiator are added to the organic solvent medium to be fully dissolved, and then transferred to the reaction system.
  • the mass ratio of electron accepting monomer to C8, C9 fraction and coal tar light fraction in the reaction system is 0.08-0.4, and at 60- The reaction is carried out at 120 ° C for 0.05-6 h.
  • reaction After the reaction is completed, it is centrifuged and dried in vacuo to obtain a C8, C9 fraction and a tar fraction of coal tar and a olefin monomer and MAH, maleimide and its derivative, and itaconic anhydride.
  • a functional copolymer formed by one or several copolymerization reactions.
  • the alkane, aromatic hydrocarbon and other components in the C8, C9 fraction and coal tar light fraction can be used as a poor medium for the reaction system, which is favorable for the formation and stability of the obtained copolymer dispersion system.
  • the beneficial effects of the invention are as follows: (1) The method directly divides the C8, C9 fraction and the coal tar light fraction into raw materials, without refining and separating, greatly reducing the cost, and the C8 fraction contains about 30% of the olefin component, and the C9 fraction is about Containing 37% of the olefin component, about 40% of the olefin component in the coal tar light fraction can be copolymerized as an electron donating monomer with MAH, maleimide and its derivatives, itaconic anhydride, and the rest Alkanes, aromatics and other components can be used as a reaction system medium, which is favorable for the formation and stability of the copolymer dispersion system, and the prepared copolymer anhydride functional group content is very high, so that the C8, C9 fraction and coal tar light fraction Resources are used effectively.
  • the invention also overcomes the problems that the C8, C9 fraction and the coal tar light fraction are complicated in composition, the boiling point is close, and the separation is difficult, so that the application thereof is limited.
  • the method adopts self-stabilized precipitation polymerization, does not require any stabilizer and stabilizer, and has high preparation efficiency, the obtained polymer is easy to be separated, the solvent is easy to be recycled and reused, and the solvent used is an alkyl acid ester, a ketone and an alkane. , low toxicity.
  • Figure 1 is a nuclear magnetic resonance ( 1 H-NMR) spectrum of a C8-MAH copolymer.
  • Figure 2 is a nuclear magnetic resonance ( 1 H-NMR) spectrum of a C9-MAH copolymer.
  • Figure 3 is an infrared spectrum of the C8-MAH and C9-MAH copolymers.
  • reaction product was centrifuged at 4000 rpm for 10 minutes, washed with petroleum ether, centrifuged three times, and dried under vacuum to constant weight to obtain 1.27 g of a C8-MAH copolymer in a yield of 94.23%. .
  • the copolymer was analyzed by three elements of C, H and O. The results are shown in Table 5. It was found that the content of the C element in the obtained C8-MAH copolymer was about 72.06%, the content of the H element was about 5.42%, and the content of the O element was about 22.52%. Since only the maleic anhydride monomer unit contains oxygen in the C8-MAH copolymer, the mass fraction of maleic anhydride in the C8-MAH copolymer is about 45.97%. By calculation, about 30% of the olefin component in the C8 fraction can be used as a comonomer for alternate copolymerization with MAH.
  • the nuclear magnetic resonance ( 1 H-NMR) spectrum of C8-MAH polymer is shown in Figure 1;
  • Figure 3 is the infrared spectrum of C8-MAH copolymer, where 1223 cm -1 is the stretching of the five-membered ring in maleic anhydride.
  • reaction product was centrifuged at 4000 rpm for 10 minutes, and washed with petroleum ether and centrifuged three times. Drying under vacuum to constant weight gave 1.91 g of a C8-MAH copolymer in a yield of 90.55%.
  • reaction product was centrifuged at 4000 rpm for 10 minutes, and washed with petroleum ether and centrifuged three times. The mixture was vacuum dried to constant weight to obtain 0.63 g of a C8-iconic anhydride copolymer, and the yield was 88.47%.
  • reaction product was centrifuged at 4000 rpm for 10 minutes, and washed with petroleum ether and centrifuged three times. Drying under vacuum to constant weight gave 4.24 g of a C8-maleimide copolymer in a yield of 89.19%.
  • xylene as a solvent for the reaction system, 5.0 g of maleic anhydride and 0.487 g of azobisisobutyronitrile were dissolved in 12.5 g of a C9 fraction (composition shown in Table 2, olefin content 38.78%) and 12.5 mL of xylene, so that ultrasonication was carried out. It is fully dissolved and mixed After homogenization, the mass ratio of MAH to C9 fraction in the reaction system was 0.40; the system was purged with nitrogen for 20 minutes, the reaction temperature was 60 ° C, and the reaction time was 6 hours.
  • reaction product was centrifuged at 4000 rpm for 10 minutes, and washed with petroleum ether and centrifuged three times. Drying under vacuum to constant weight gave 9.17 g of a C9-MAH copolymer in a yield of 93.10%.
  • the copolymer was analyzed by three elements of C, H and O. The results are shown in Table 6. It is understood that the content of the C element in the obtained C9-MAH copolymer is about 71.87%, the content of the H element is about 5.83%, and the content of the O element is about 22.30%. Since only the maleic anhydride monomer contains oxygen in the C9-MAH copolymer, the mass fraction of maleic anhydride in the C9-MAH copolymer is about 45.52%. By calculation, about 37% of the monomers in the C9 fraction can participate in the copolymerization reaction.
  • the nuclear magnetic resonance ( 1 H-NMR) spectrum of C9-MAH polymer is shown in Figure 2;
  • Figure 3 is the infrared spectrum of C9-MAH copolymer, where 1223 cm -1 is the stretching of the five-membered ring in maleic anhydride.
  • reaction product was centrifuged at 4000 rpm for 10 minutes, and washed with petroleum ether and centrifuged three times. Drying under vacuum to constant weight gave 9.33 g of a C9-MAH copolymer in a yield of 94.74%.
  • ethyl butyrate as a solvent for the reaction system, 3.0 g of maleimide and 0.097 g of dibenzoyl peroxide were dissolved in 12.5 g of C9 fraction (composition shown in Table 2, olefin content 38.78%) and 12.5 mL.
  • the mass ratio of the maleimide to the C9 fraction in the reaction system was 0.24 after the ultrasonic solution was sufficiently dissolved and uniformly mixed; the system was purged with nitrogen for 20 minutes, the reaction temperature was 95 ° C, and the reaction time was 6 hours.
  • reaction product was centrifuged at 4000 rpm for 10 minutes, and washed with petroleum ether and centrifuged three times. Drying under vacuum to constant weight gave 6.68 g of a C9-maleimide copolymer in a yield of 85.11%.
  • reaction product was centrifuged at 4000 rpm for 10 minutes, and washed with petroleum ether and centrifuged three times. Drying under vacuum to constant weight gave 1.32 g of a C9-iconic anhydride copolymer in a yield of 93.81%.
  • reaction product was centrifuged at 4000 rpm for 10 minutes, and washed with petroleum ether and centrifuged three times. Drying under vacuum to constant weight gave 8.78 g of coal tar-maleimide copolymer in a yield of 90.01%.

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Abstract

L'invention concerne un copolymère fonctionnel préparé directement à partir d'un mélange d'hydrocarbures supérieurs et un procédé pour sa préparation, relevant du domaine des applications de ressources pétrolières. Dans des conditions de protection contre l'azote, un ou plusieurs parmi le MAH, le maléimide et des dérivés correspondants, de l'anhydride itaconique ainsi qu'un initiateur de radicaux libres soluble dans l'huile sont ajoutés dans un solvant sélectionné pour être totalement dissous, puis une ou plusieurs des fractions en C8 et en C9 susmentionnées et des fractions légères de goudron de houille sont ajoutées dans le système mentionné ci-dessus pour être mélangées uniformément, on effectue ensuite une réaction à une température de 60-120°C et après la fin de la réaction, le copolymère fonctionnel formé par copolymérisation de constituants oléfiniques et d'anhydride maléique dans le mélange susmentionné est obtenu par la réalisation d'une séparation et d'un séchage. Dans la présente invention, des fractions en C8 et en C9 et des fractions légères de goudron de houille sont directement utilisées en tant que matières premières destinées à être soumises à une réaction en une étape pour préparer le copolymère comprenant des groupes fonctionnels. Le procédé est simple, les conditions de réaction sont douces et l'efficacité de préparation est élevée, le copolymère préparé est facile à séparer des constituants non polymérisés et la teneur en groupes fonctionnels dans le copolymère est élevée, de sorte que les ressources en fractions en C8 et en C9 ainsi qu'en fractions légères de goudron de houille peuvent être utilisées de manière raisonnable et efficace.
PCT/CN2016/103475 2016-05-23 2016-10-27 Copolymère fonctionnel préparé directement à partir d'un mélange d'hydrocarbures supérieurs et procédé pour sa préparation Ceased WO2017201964A1 (fr)

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