EP1117704A1 - Verfahren zur hydrierung aromatischer polymere in gegenwart von sauerstoffenthaltenden kohlenwasserstoffen - Google Patents
Verfahren zur hydrierung aromatischer polymere in gegenwart von sauerstoffenthaltenden kohlenwasserstoffenInfo
- Publication number
- EP1117704A1 EP1117704A1 EP99932865A EP99932865A EP1117704A1 EP 1117704 A1 EP1117704 A1 EP 1117704A1 EP 99932865 A EP99932865 A EP 99932865A EP 99932865 A EP99932865 A EP 99932865A EP 1117704 A1 EP1117704 A1 EP 1117704A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- oxygen
- hydrogenation
- catalysts
- mixture
- pore
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/04—Reduction, e.g. hydrogenation
-
- 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
- C08F12/00—Homopolymers and 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 an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/06—Hydrocarbons
- C08F12/08—Styrene
-
- 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
- C08F12/00—Homopolymers and 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 an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/06—Hydrocarbons
- C08F12/12—Monomers containing a branched unsaturated aliphatic radical or a ring substituted by an alkyl radical
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/14—Methyl esters, e.g. methyl (meth)acrylate
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/42—Nitriles
- C08F20/44—Acrylonitrile
-
- 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
- C08F22/00—Homopolymers and 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
- C08F22/04—Anhydrides, e.g. cyclic anhydrides
- C08F22/06—Maleic anhydride
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/70—Iron group metals, platinum group metals or compounds thereof
Definitions
- the invention relates to a process for the hydrogenation of aromatic polymers, which is characterized in that metals of subgroup VIII are present together with a carrier composed of silicon dioxide or aluminum oxide or mixtures thereof.
- the catalysts have a pore size distribution which is characterized in that the pore volume is between 100 and 1,000 ⁇ less than 15%.
- the process is carried out in the presence of a reaction-accelerating oxygen-containing hydrocarbon and completely hydrogenates aromatic polymers with regard to their aromatic units and without significant degradation of the molecular weights.
- EP-A-322 731 describes the production of predominantly syndiotactic polymers based on vinylcyclohexane, a styrene-based polymer being hydrogenated in the presence of hydrogenation catalysts and solvents. Cycloaliphatic and aromatic hydrocarbons, but not ethers, are mentioned as solvents.
- the use of special silicon dioxide-assisted hydrogenation catalysts permits an almost complete hydrogenation with approximately 20% degradation of the molecular weights.
- the catalysts mentioned have a special pore size distribution of silicon dioxide, which is characterized in that 98% of the pore volume has a pore diameter greater than 600 ⁇ .
- the catalysts mentioned have surfaces between 14-17 m 2 / g and average pore diameter of 3800-3900 ⁇ . Diluted polystyrene solutions in cyclohexane (polymer concentration between 1% and a maximum of 8%) are hydrogenated to degrees of hydrogenation greater than 98% and less than 100%.
- the comparative example according to WO 96/34896 of a commercially available 5% Rh / Al 2 O 3 catalyst leads to a degree of hydrogenation of 7% and shows a lower activity of the alumina support compared to the silica-supported catalyst.
- the process is characterized by the fact that there is no significant degradation of the end product, especially at high polymer concentrations (e.g.> 20%).
- the invention relates to a process for the hydrogenation of aromatic polymers in the presence of catalysts and in the presence of an oxygen-containing hydrocarbon, the catalyst being a metal or mixture of metals of subgroup VIII of the periodic table together with a carrier composed of silicon dioxide, aluminum oxide or a mixture thereof, and that Pore volume of the pore diameter of the catalyst measured between 100 and 1,000 ⁇
- Mercury porosimetry less than 15% (preferably 2 to 12%) based on the total pore volume, measured according to the mercury porosimetry.
- the mean pore diameter, determined according to mercury porosimetry, is at most 900 ⁇ .
- the mercury method is only sufficiently accurate for pores that are larger than 60 ⁇ . Pore diameters smaller than 600 ⁇ are therefore determined by nitrogen sorption, the Barrett, Joyner and Halenda method in accordance with DIN 66 134.
- Nitrogen sorption from 100 to 10%, preferably 80 to 10%, in particular 70 to 15% for pore diameters ⁇ 600 ⁇ .
- the pore volume, measured after nitrogen sorption, refers to the total pore volume, measured according to mercury porosimetry.
- the mean pore diameter and the pore size distribution are determined by mercury porosimetry in accordance with DIN 66133.
- the catalysts consist of metals of subgroup VIII, which are present together with a support made of silicon dioxide or aluminum oxide or mixtures thereof.
- the catalysts characterized in this way have a pore size distribution which is characterized in that 100 to 10%, preferably 80 to 10%, very particularly preferably 70 to 15% of the pore volume have a pore diameter of less than 600 ⁇ , determined according to nitrogen sorption according to the measured total pore volume
- the average pore diameter is generally 10 to 1000 ⁇ , preferably 50 to 950 ⁇ , very particularly preferably 60 to 900 ⁇ .
- the specific nitrogen surface areas are generally 80 to 800 m 2 / g, preferably 100 to 600 m 2 / g.
- Metals from subgroup VIII preferably nickel, platinum, ruthenium, rhodium, palladium, are generally used.
- the metal content is generally 0.01 to 80%, preferably 0.05 to 70%, based on the total weight of the catalyst.
- the 50% value of the cumulative distribution of the particle size in the discontinuously operated process is generally 0.1 ⁇ m to 200 ⁇ m, preferably 1 ⁇ m to 100 ⁇ m, very particularly preferably 3 ⁇ m to 80 ⁇ m.
- solvents customary for hydrogenation reactions are used as solvents. These are generally aliphatic and cycloaliphatic hydrocarbons, ethers, alcohols and aromatic hydrocarbons. Cyclohexane, tetrahydrofuran or a mixture thereof are preferred.
- Part or all of the solvent is replaced by an oxygen-containing hydrocarbon or a mixture of such compounds.
- Oxygenated hydrocarbons are preferably ether having up to 20 carbon atoms and up to 10, preferably up to 6 oxygen atoms, polyethers with C j -C - alkyl units between the oxygen atoms and molecular weights of from 100 to 100,000 g MOH, C r C 2 o-alkanols or C r C 8 alkoxy-C r C 8 alkyl,
- the alkyl radicals are each straight-chain or branched.
- diethyl ether ethylene glycol diethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, tetrahydrofuran, dioxane, trioxane, crown ether e.g. [18] crown 6, [12] crown 4.
- the reaction is generally carried out at concentrations of the oxygen-containing component to the total solvent of 0.1% to 100%, preferably 1% to 60%, very particularly preferably 5% to 50%.
- concentrations of the oxygen-containing component to the total solvent of 0.1% to 100%, preferably 1% to 60%, very particularly preferably 5% to 50%.
- the process according to the invention generally leads to a virtually complete hydrogenation of the aromatic units.
- the degree of hydrogenation is> 80%, preferably> 90%, very particularly preferably> 99% to 100%.
- the degree of hydrogenation can be determined, for example, by NMR or UV spectroscopy.
- Aromatic polymers are used as starting materials, which are selected, for example, from polystyrene optionally substituted in the phenyl ring or on the vinyl group or copolymers thereof with monomers selected from the group of olefins, (meth) acrylates or mixtures thereof.
- aromatic polyethers in particular polyphenylene oxide, aromatic polycarbonates, aromatic polyesters, aromatic polyamides, polyphenylenes, polyxylenes, polyphenylene vinylenes, polyphenylene ethylenes, polyphenylene sulfides, polyaryl ether ketones, aromatic polysulfones, aromatic polyether sulfones, aromatic polyimides and mixtures thereof, Copolymers, optionally copolymers with aliphatic compounds.
- substituents in the phenyl ring come C 1 -C 4 alkyl, such as methyl, ethyl, C 1 -C 4 alkoxy, such as methoxy, ethoxy, fused aromatics which are connected to the phenyl ring via a carbon atom or two carbon atoms, with phenyl, biphenyl, Naphthyl in question.
- Possible substituents on the vinyl group are C 1 -C 4 -alkyl, such as methyl, ethyl, n- or iso-propyl, in particular methyl in the ⁇ -position.
- Suitable olefinic comonomers are ethylene, propylene, isoprene, isobutylene butadiene, cyclohexadiene, cyclohexene, cyclopentadiene, optionally substituted norbornenes, optionally substituted dicyclopentadienes, optionally substituted tetracyclododecenes, optionally substituted dihydrocyclopentadienes,
- Ci -Cg- preferably -C -C4 alkyl esters of (meth) acrylic acid, preferably
- Methyl and ethyl esters Ci -Cg-, preferably Ci -Ci-alkyl ether of vinyl alcohol, preferably methyl and ethyl ether,
- Ci-Cg- preferably Ci-Czi-alkyl esters of vinyl alcohol, preferably vinyl acetate,
- Preferred polymers are polystyrene, polymethylstyrene, copolymers of styrene and at least one further monomer selected from the group consisting of ⁇ -methylstyrene, butadiene, isoprene, acrylonitrile, methyl acrylate, methyl methacrylate, maleic anhydride and olefins such as ethylene and propylene.
- copolymers of acrylonitrile, butadiene and styrene are suitable,
- the aromatic polymers generally have molecular weights (weight average) M w from 1000 to 10,000,000, preferably from 60,000 to 1,000,000, particularly preferably 70,000 to 600,000, in particular 100,000 to 480,000, determined by light scattering.
- the polymers can have a linear chain structure as well as branching points due to co-units (e.g. graft copolymers).
- the branch centers include e.g. star-shaped polymers or other geometric shapes of the primary, secondary, tertiary, possibly quaternary polymer structure.
- the copolymers can be either random, alternating or block copolymers.
- Block copolymers include di-blocks, tri-blocks, multi-blocks and star-shaped block copolymers.
- the amount of catalyst to be used is described, for example, in WO 96/34896.
- the amount of catalyst to be used depends on the process to be carried out; this can be carried out continuously, semi-continuously or batchwise.
- the response time is much shorter; it is influenced by the dimensions of the reaction vessel.
- the trickle system and the sump system both with fixed catalysts, are possible, as is a system with a suspended and e.g. circulated catalyst.
- the fixed catalysts can be in tablet form or as
- the polymer concentrations are generally 80 to 1, preferably 50 to 10, in particular 40 to 15% by weight in the batch process.
- the reaction is generally carried out at temperatures between 0 and 500 ° C, preferably between 20 and 250 ° C, in particular between 60 and 200 ° C.
- the reaction is generally preferred at pressures from 1 bar to 1000 bar
- the absolute molecular weights Mw (weight average) of the starting polymer and of the hydrogenated product are determined by light scattering.
- Membrane osmosis provides the absolute molecular weights Mn (number average).
- the relative values of the GPC measurement compared to polystyrene standards correspond to the determined absolute molecular weights of the polystyrene used.
- the reaction time is the time from heating the batch to complete hydrogenation of the polystyrene or, if the hydrogenation is incomplete, the time until the hydrogen uptake approaches its saturation value.
- Glyme ethylene glycol dimethyl ether
- Catalyst no. 1 Aldrich, Steinheim, Germany, nickel on silicon dioxide / aluminum oxide, order no. 20 877-9 catalyst no. 2: Engelhard, De Meern BV, Netherlands, Ni-5136P, nickel on silicon dioxide / aluminum oxide! ) Average pore diameter by mercury porosimetry (DIN 66 133) 2 ) Specific nitrogen total surface according to Brunauer, Emmett and Teller (BET, DIN 66131, DIN 66132)
- the nickel catalyst (Table 1) does not completely hydrogenate polystyrene at 160 ° C. in a reaction time of 13 hours to 98.5% (comparative example 1). At 200 ° C., however, the hydrogenation is complete after only 7 hours, with a drastic decrease in molecular weight (comparative example 2).
- the process according to the invention leads to a reduction in the reaction temperature required for complete hydrogenation, with a much shorter reaction time and while maintaining the absolute molecular weights M n and M w compared to the starting polymer (Example 3,4,5).
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19833095 | 1998-07-23 | ||
DE19833095A DE19833095A1 (de) | 1998-07-23 | 1998-07-23 | Verfahren zur Hydrierung aromatischer Polymere in Gegenwart von sauerstoffenthaltenden Kohlenwasserstoffen |
PCT/EP1999/004880 WO2000005278A1 (de) | 1998-07-23 | 1999-07-12 | Verfahren zur hydrierung aromatischer polymere in gegenwart von sauerstoffenthaltenden kohlenwasserstoffen |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1117704A1 true EP1117704A1 (de) | 2001-07-25 |
Family
ID=7875001
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP99932865A Withdrawn EP1117704A1 (de) | 1998-07-23 | 1999-07-12 | Verfahren zur hydrierung aromatischer polymere in gegenwart von sauerstoffenthaltenden kohlenwasserstoffen |
Country Status (12)
Country | Link |
---|---|
US (1) | US6420491B1 (ko) |
EP (1) | EP1117704A1 (ko) |
JP (1) | JP2002521508A (ko) |
KR (1) | KR20010071017A (ko) |
CN (1) | CN1310727A (ko) |
AU (1) | AU4909599A (ko) |
BR (1) | BR9912355A (ko) |
CA (1) | CA2338229A1 (ko) |
DE (1) | DE19833095A1 (ko) |
HK (1) | HK1039343A1 (ko) |
WO (1) | WO2000005278A1 (ko) |
ZA (1) | ZA200100085B (ko) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004029103A1 (en) * | 2002-09-25 | 2004-04-08 | Dow Global Technologies Inc. | Improved process for hydrogenating unsaturated polymers |
US7408009B2 (en) * | 2002-11-05 | 2008-08-05 | North Carolina State University | Hydrogenation of polymers in the presence of supercritical carbon dioxide |
US7053156B2 (en) * | 2003-12-19 | 2006-05-30 | Kraton Polymers U.S. Llc | Process for hydrogenating block copolymers |
TWI396701B (zh) * | 2006-02-27 | 2013-05-21 | Mitsubishi Gas Chemical Co | 氫化聚合物之製法 |
JP5540703B2 (ja) | 2007-08-06 | 2014-07-02 | 三菱瓦斯化学株式会社 | 核水素化された芳香族ビニル化合物/(メタ)アクリレート系共重合体の製造方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL274062A (ko) * | 1961-01-28 | 1900-01-01 | ||
NL274061A (ko) | 1961-01-28 | 1900-01-01 | ||
LU74570A1 (ko) | 1976-03-16 | 1977-09-27 | ||
JP2597375B2 (ja) | 1987-12-29 | 1997-04-02 | 出光興産株式会社 | ビニルシクロヘキサン系重合体およびその製造方法 |
US4892928A (en) | 1988-10-12 | 1990-01-09 | Shell Oil Company | Hydrogenation process |
US5028665A (en) * | 1989-01-09 | 1991-07-02 | The Dow Chemical Company | Polymer hydrogenation catalysts |
JPH0539315A (ja) | 1991-08-02 | 1993-02-19 | Nippon Steel Chem Co Ltd | 水素化芳香族樹脂の製造方法 |
US5612422A (en) * | 1995-05-04 | 1997-03-18 | The Dow Chemical Company | Process for hydrogenating aromatic polymers |
US6248924B1 (en) | 1996-06-19 | 2001-06-19 | Basf Aktiengesellschaft | Process for reacting an organic compound in the presence of a supported ruthenium catalyst |
-
1998
- 1998-07-23 DE DE19833095A patent/DE19833095A1/de not_active Withdrawn
-
1999
- 1999-07-12 WO PCT/EP1999/004880 patent/WO2000005278A1/de not_active Application Discontinuation
- 1999-07-12 BR BR9912355-0A patent/BR9912355A/pt not_active IP Right Cessation
- 1999-07-12 EP EP99932865A patent/EP1117704A1/de not_active Withdrawn
- 1999-07-12 JP JP2000561233A patent/JP2002521508A/ja active Pending
- 1999-07-12 CN CN99809026A patent/CN1310727A/zh active Pending
- 1999-07-12 AU AU49095/99A patent/AU4909599A/en not_active Abandoned
- 1999-07-12 CA CA002338229A patent/CA2338229A1/en not_active Abandoned
- 1999-07-12 KR KR1020017000981A patent/KR20010071017A/ko not_active Application Discontinuation
- 1999-07-12 US US09/743,830 patent/US6420491B1/en not_active Expired - Fee Related
-
2001
- 2001-01-04 ZA ZA200100085A patent/ZA200100085B/en unknown
-
2002
- 2002-02-05 HK HK02100893.6A patent/HK1039343A1/zh unknown
Non-Patent Citations (1)
Title |
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See references of WO0005278A1 * |
Also Published As
Publication number | Publication date |
---|---|
CA2338229A1 (en) | 2000-02-03 |
KR20010071017A (ko) | 2001-07-28 |
JP2002521508A (ja) | 2002-07-16 |
AU4909599A (en) | 2000-02-14 |
HK1039343A1 (zh) | 2002-04-19 |
ZA200100085B (en) | 2002-01-04 |
CN1310727A (zh) | 2001-08-29 |
WO2000005278A1 (de) | 2000-02-03 |
BR9912355A (pt) | 2001-04-17 |
US6420491B1 (en) | 2002-07-16 |
DE19833095A1 (de) | 2000-01-27 |
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