JP4499566B2 - 工業的メチルt−ブチルエーテルからイソブテンを製造する方法 - Google Patents
工業的メチルt−ブチルエーテルからイソブテンを製造する方法 Download PDFInfo
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- isobutene
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- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims description 177
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 title claims description 77
- 238000000034 method Methods 0.000 title claims description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 162
- 238000000926 separation method Methods 0.000 claims description 50
- 239000000047 product Substances 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 28
- 238000004821 distillation Methods 0.000 claims description 19
- 238000000354 decomposition reaction Methods 0.000 claims description 13
- 229930195733 hydrocarbon Natural products 0.000 claims description 13
- 238000000066 reactive distillation Methods 0.000 claims description 8
- 210000003918 fraction a Anatomy 0.000 claims description 7
- FVNIMHIOIXPIQT-UHFFFAOYSA-N 2-methoxybutane Chemical compound CCC(C)OC FVNIMHIOIXPIQT-UHFFFAOYSA-N 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 6
- 238000005336 cracking Methods 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 22
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 16
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 10
- 230000002378 acidificating effect Effects 0.000 description 10
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- -1 C 5 aldehydes Chemical class 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 6
- 239000003456 ion exchange resin Substances 0.000 description 6
- 229920003303 ion-exchange polymer Polymers 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 229920001429 chelating resin Polymers 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 239000000446 fuel Substances 0.000 description 5
- 239000001282 iso-butane Substances 0.000 description 5
- 238000012856 packing Methods 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 3
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000356 contaminant Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000006266 etherification reaction Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- GGNZMWOPPLQFQU-UHFFFAOYSA-N methanol;2-methoxy-2-methylpropane Chemical compound OC.COC(C)(C)C GGNZMWOPPLQFQU-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- VTPNYMSKBPZSTF-UHFFFAOYSA-N 1-ethenyl-2-ethylbenzene Chemical compound CCC1=CC=CC=C1C=C VTPNYMSKBPZSTF-UHFFFAOYSA-N 0.000 description 1
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- LAAVYEUJEMRIGF-UHFFFAOYSA-N 2,4,4-trimethylpent-2-ene Chemical compound CC(C)=CC(C)(C)C LAAVYEUJEMRIGF-UHFFFAOYSA-N 0.000 description 1
- ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000013590 bulk material Substances 0.000 description 1
- SOUGLODYPBMACB-UHFFFAOYSA-N butane;hydrate Chemical compound O.CCCC SOUGLODYPBMACB-UHFFFAOYSA-N 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 230000006326 desulfonation Effects 0.000 description 1
- 238000005869 desulfonation reaction Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/08—Alkenes with four carbon atoms
- C07C11/09—Isobutene
-
- 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
- C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
- C07C7/08—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by extractive distillation
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
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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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
MTBE、C4−、C5−炭化水素、メタノール、メチル−s−ブチルエーテル、TBAおよびC4−オリゴマーを含有する出発混合物を、
a)MTBE、MSBE、TBAおよびC4−オリゴマーを含有する留分a)と、
b)C4−、C5−炭化水素、MTBEおよびメタノールを含有する留分b)に分離し、
c)留分a)に含まれるMTBEをメタノールとイソブテンに分解し、かつ
d)c)からの分解生成物を、イソブテン含有流の分離後に出発混合物に返送する。
MTBEの分解および未反応MTBEからの製造したイソブテンとメタノールの分離を図1に示される、MTBE合成工程(13)を有しない装置で実施した。MTBE−メタノール共沸混合物およびC4−およびC5−炭化水素部分の分離のために、織物充填物Sulzer BXが充填され、30個の理論的分離段を有するカラム(2)を使用した。その際濃縮部分は内径50mmおよび15個の分離段を有し、可動部分は内径80mmおよび同様に15個の分離段を有した。イソブテンの分離を、内径50mmを有するカラム(9)内で実施し、前記カラムは同様に織物充填物Sulzer BXが充填され、35個の理論的分離段を有した。MTBE分解のために、内径21mmおよび長さ160mmを有する管形反応器(7)を使用した。触媒として市販されているイオン交換樹脂 Bayer LewatitK2621を使用した。管形反応器は温度調節された油浴中、100℃で運転した。
ジメチルエーテルおよび水の分離によるイソブテンの精製を図3により直径50mmを有するカラム中で実施した。前記カラムはSulzer BX織物充填物が充填され、35個の理論的分離段を有した。その際デカンター(22)はカラム(18)の塔頂に配置され、デカンターから水相(23)が取り出される。装置の供給物はMTBE分離(例えば図1による)に由来し、水での抽出によるメタノール分離が後方に接続されていた。
この試験においては図2により例2と同じカラムを使用して運転したが、デカンターは供給段の下に配置された。
Claims (9)
- メチルt−ブチルエーテル(MTBE)の酸性触媒作用させた分解によりイソブテンを製造する方法において、MTBE、C4−、C5−炭化水素、メタノール、メチルs−ブチルエーテル、t−ブタノール(TBA)およびC4−オリゴマーを含有する出発混合物を、
a)MTBE,2−メトキシブタン(MSBE),TBAおよびC4−オリゴマーを含有する留分a)と、
b)C4−、C5−炭化水素、MTBEおよびメタノールを含有する留分b)に分離し、
c)留分a)に含まれるMTBEをメタノールとイソブテンに分解し、かつ
d)未反応MTBE、メタノール、イソブテン、低沸点物および高沸点物を含有する、c)からの分解生成物を、塔中で、イソブテン含有塔頂生成物と、未反応MTBEおよび大部分の分離メタノールを含有する塔底生成物に分離し、塔底生成物を出発混合物に返送する
ことを特徴とするイソブテンの製造方法。 - 留分a)からC4−オリゴマー、MSBEおよびTBAを蒸留工程により塔底生成物として分離する請求項1記載の方法。
- 留分a)からC4−オリゴマー、MSBEおよびTBAを排出流により分離する請求項1記載の方法。
- c)からの分解生成物から分離されたイソブテン含有流を、精留塔で純粋なイソブテンを含有する塔底生成物と、イソブテンおよび揮発しやすい副生成物を含有する塔頂生成物に分留する請求項1から3までのいずれか1項記載の方法。
- c)からの分解生成物から分離されたイソブテン含有流を水で洗浄し、引続き精留塔で、純粋なイソブテンを含有する塔底生成物と、イソブテンおよび揮発しやすい副生成物を含有する塔頂生成物に分留する請求項1から3までのいずれか1項記載の方法。
- イソブテン含有流に含まれる水を、デカンターを用いて除去する請求項4または5記載の方法。
- イソブテン含有流に含まれる水を、精留塔の塔頂部に配置されているデカンターを用いて除去する請求項4から6までのいずれか1項記載の方法。
- イソブテン含有流に含まれる水を、精留塔の側面排出部として配置されているデカンターを用いて除去する請求項4から6までのいずれか1項記載の方法。
- 留分a)に含まれるMTBEのc)による分解およびd)によるイソブテンの分離を、反応蒸留塔中で実施する請求項1から8までのいずれか1項記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10238370A DE10238370A1 (de) | 2002-08-22 | 2002-08-22 | Verfahren zur Herstellung von Isobuten aus technischen Methyl-tert.-butylether |
PCT/EP2003/007543 WO2004018393A1 (de) | 2002-08-22 | 2003-07-11 | Verfahren zur herstellung von isobuten aus technischen methyl-tert.-butylether |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005536542A JP2005536542A (ja) | 2005-12-02 |
JP4499566B2 true JP4499566B2 (ja) | 2010-07-07 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2004530017A Expired - Fee Related JP4499566B2 (ja) | 2002-08-22 | 2003-07-11 | 工業的メチルt−ブチルエーテルからイソブテンを製造する方法 |
Country Status (10)
Country | Link |
---|---|
US (1) | US7439413B2 (ja) |
EP (1) | EP1530556A1 (ja) |
JP (1) | JP4499566B2 (ja) |
KR (1) | KR20050058406A (ja) |
CN (1) | CN1325444C (ja) |
AU (1) | AU2003246684A1 (ja) |
DE (1) | DE10238370A1 (ja) |
PL (1) | PL206182B1 (ja) |
TW (1) | TWI307686B (ja) |
WO (1) | WO2004018393A1 (ja) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102005062722A1 (de) * | 2005-12-28 | 2007-07-12 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Ethyl-tert.-Butylether aus technischen Mischungen von C4-Kohlenwasserstoffen |
JP2007269708A (ja) * | 2006-03-31 | 2007-10-18 | Sumitomo Chemical Co Ltd | 第3級オレフィンおよび脂肪族アルコールの製造方法 |
DE102006040433A1 (de) * | 2006-08-29 | 2008-03-13 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Isoolefinen |
DE102006040431A1 (de) | 2006-08-29 | 2008-03-20 | Oxeno Olefinchemie Gmbh | Verfahren zur Spaltung von MTBE |
DE102006040434A1 (de) | 2006-08-29 | 2008-03-06 | Oxeno Olefinchemie Gmbh | Verfahren zur Spaltung von MTBE |
DE102006040430B4 (de) * | 2006-08-29 | 2022-06-15 | Evonik Operations Gmbh | Verfahren zur Spaltung von MTBE |
DE102006040432A1 (de) * | 2006-08-29 | 2008-03-20 | Oxeno Olefinchemie Gmbh | Katalysator und Verfahren zur Herstellung von Isoolefinen |
SI1995231T1 (sl) * | 2007-05-25 | 2014-03-31 | Evonik Roehm Gmbh | Postopek za pripravo metil metakrilata z uporabo recikliranega metanola |
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2002
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- 2003-07-11 WO PCT/EP2003/007543 patent/WO2004018393A1/de active Application Filing
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US7439413B2 (en) | 2008-10-21 |
US20060135833A1 (en) | 2006-06-22 |
CN1325444C (zh) | 2007-07-11 |
WO2004018393A1 (de) | 2004-03-04 |
CN1678549A (zh) | 2005-10-05 |
JP2005536542A (ja) | 2005-12-02 |
EP1530556A1 (de) | 2005-05-18 |
PL206182B1 (pl) | 2010-07-30 |
PL373774A1 (en) | 2005-09-19 |
TWI307686B (en) | 2009-03-21 |
AU2003246684A1 (en) | 2004-03-11 |
DE10238370A1 (de) | 2004-03-04 |
KR20050058406A (ko) | 2005-06-16 |
TW200413275A (en) | 2004-08-01 |
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