JP2008511577A - 2,7−オクタジエニル誘導体の製造法 - Google Patents
2,7−オクタジエニル誘導体の製造法 Download PDFInfo
- Publication number
- JP2008511577A JP2008511577A JP2007528842A JP2007528842A JP2008511577A JP 2008511577 A JP2008511577 A JP 2008511577A JP 2007528842 A JP2007528842 A JP 2007528842A JP 2007528842 A JP2007528842 A JP 2007528842A JP 2008511577 A JP2008511577 A JP 2008511577A
- Authority
- JP
- Japan
- Prior art keywords
- butadiene
- treatment step
- alkyl
- hydrogenation
- telopolymerization
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- -1 2,7-octadienyl Chemical class 0.000 title claims description 82
- 150000001875 compounds Chemical class 0.000 claims abstract description 83
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 69
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 61
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 57
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 52
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 239000012434 nucleophilic reagent Substances 0.000 claims abstract description 34
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 159
- 238000000034 method Methods 0.000 claims description 84
- 239000003054 catalyst Substances 0.000 claims description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 27
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 229910052802 copper Inorganic materials 0.000 claims description 16
- 239000010949 copper Substances 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 16
- 239000002184 metal Substances 0.000 claims description 16
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 15
- 150000001361 allenes Chemical class 0.000 claims description 15
- 238000004821 distillation Methods 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229910052763 palladium Inorganic materials 0.000 claims description 13
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 5
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 claims description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004673 propylcarbonyl group Chemical group 0.000 claims description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 150000002736 metal compounds Chemical class 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 235000011054 acetic acid Nutrition 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- 150000001993 dienes Chemical class 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- HZYABSBSRWFZEG-BSWSSELBSA-N (1E,3E)-octa-1,3-dien-1-ol Chemical compound CCCC\C=C\C=C\O HZYABSBSRWFZEG-BSWSSELBSA-N 0.000 claims description 2
- MDVPRIBCAFEROC-BQYQJAHWSA-N (e)-oct-1-en-1-ol Chemical compound CCCCCC\C=C\O MDVPRIBCAFEROC-BQYQJAHWSA-N 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 125000003717 m-cresyl group Chemical group [H]C1=C([H])C(O*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000000486 o-cresyl group Chemical group [H]C1=C([H])C(O*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000000552 p-cresyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1O*)C([H])([H])[H] 0.000 claims 1
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical class CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract description 3
- 210000000540 fraction c Anatomy 0.000 abstract 1
- 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 26
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 25
- 239000002904 solvent Substances 0.000 description 25
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 20
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 16
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 14
- 238000000926 separation method Methods 0.000 description 14
- 238000000895 extractive distillation Methods 0.000 description 11
- 239000003446 ligand Substances 0.000 description 10
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 9
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
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- 150000002431 hydrogen Chemical class 0.000 description 7
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 6
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- 230000009257 reactivity Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 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
- 229930192474 thiophene Natural products 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- CPWJKGIJFGMVPL-UHFFFAOYSA-K tricesium;phosphate Chemical class [Cs+].[Cs+].[Cs+].[O-]P([O-])([O-])=O CPWJKGIJFGMVPL-UHFFFAOYSA-K 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
この場合、使用炭化水素混合物から選択水素化によってアセチレン系不飽和化合物を除去し、引続きテロ重合を実施する。
Description
R1a−O−H (III) (R1a)(R1b)N−H (IV) R1a−COOH (V)
〔式中、R1aおよびR1bは、上記の意味を有する〕で示される求核性試薬との反応によって製造されてよい。
R1bが、H、メチル、エチル、n−プロピル、イソプロピル、第三ブチル、n−ブチル、第二ブチル、ペンチル、ヘキシル、ヘプチル、オクチル、オクテニル、オクタジエニル、イソノニル、2−エチルヘキシル、n−ノニル、フェニル、m−メチルフェニル、o−メチルフェニルまたはp−メチルフェニル、ナフチル、2,4−ジ−第三ブチルフェニル、2,6−ジ−第三ブチルメチルフェニル、ヒドロジェンカルボニル、メチルカルボニル、エチルカルボニル、プロピルカルボニルまたはフェニルカルボニルであるような式Iの化合物が製造される。殊に好ましくは、本発明による方法により、R1aが水素、メチル、エチル、フェニルまたはメチルカルボニルである式IIaの化合物が製造される。式IIaおよびIIbの化合物は、シス形で存在していてもよいし、トランス形で存在していてもよい。
水、アンモニア、
モノアルコールおよびフェノール、例えばメタノール、エタノール、n−プロパノール、イソプロパノール、アリルアルコール、n−ブタノール、イソブタノール、オクタノール、2−エチルヘキサノール、イソノナノール、ベンジルアルコール、シクロヘキサノール、シクロペンタノールまたは2,7−オクタジエン−1−オール、フェノール、
ジアルコール、例えばエチレングリコール、1,2−プロパンジオール、1,3−プロパンジオール、1,4−ブタンジオール、1,2−ブタンジオール、2,3−ブタンジオールおよび1,3−ブタンジオール、
ヒドロキシ化合物、例えばα−ヒドロキシ酢酸エステル、
第1アミン、例えばメチルアミン、エチルアミン、プロピルアミン、ブチルアミン、オクチルアミン、2,7−オクタジエニルアミン、ドデシルアミン、エチレンジアミンまたはヘキサンメチレンジアミン、
第2アミン、例えばジメチルアミン、ジエチルアミン、N−メチルアニリン、ビス(2,7−オクタジエニル)アミン、ジシクロヘキシルアミン、メチルシクロヘキシルアミン、ピロリジン、ピペリジン、モルホリン、ピペラジンまたはヘキサメチレンイミンまたは
カルボン酸、例えば蟻酸、酢酸、プロパン酸、ブテン酸、イソブテン酸、安息香酸、1,2−ベンゼンジカルボン酸(フタル酸)。
基R2〜R7は、構造式VI〜IX中で次の意味を有する:
R2、R3:同一かまたは異なるa)線状、分枝鎖状の置換されたかまたは置換されていない、1〜24個の炭素原子を有する環状または脂環状のアルキル基、
またはb)置換されたかまたは置換されていない、6〜24個の炭素原子を有する単環式または多環式アリール基、
またはc)置換されたかまたは置換されていない、4〜24個の炭素原子および基N、O、Sからの少なくとも1つのヘテロ原子を有する単環式または多環式複素環、
R4、R5、R6、R7:同一かまたは異なる水素、アルキル、アリール、ヘテロアリール、−CN、−COOH、−COO−アルキル−、−COO−アリール−、−OCO−アルキル−、−OCO−アリール−、−OCOO−アルキル−、−OCOO−アリール−、−CHO−、−CO−アルキル、−CO−アリール、−O−アルキル−、−O−アリール−、−NH2、−NH(アルキル)−、−N(アルキル)2−、−NH(アリール)−、−N(アルキル)2−、−F、−Cl、−Br、−I、−OH、−CF3、−NO2、−フェロセニル、−SO3H、−PO3H2、この場合アルキル基は、1〜24個の炭素原子を含み、アリール基およびヘテロアリール基は、5〜24個の炭素原子を含み、基R4およびR5は、橋かけ脂肪族または芳香族の環の一部分であってもよい。
1〜24個の炭素原子を有する線状、分枝鎖状の環状または脂環状アルキル基、
6〜24個の炭素原子を有する単環式または多環式アリール基または
元素の窒素、酸素および硫黄から選択された少なくとも1個のヘテロ原子を有する単環式または多環式の環を表わし、
前記環は、場合によっては−CN、−COOH、−COO−アルキル−、−COO−アリール−、−OCO−アルキル−、−OCO−アリール−、−OCOO−アルキル−、−OCOO−アリール−、−CHO、−CO−アルキル−、−CO−アリール−、−アリール−、−アルキル−、−O−アルキル−、−O−アリール−、−NH2、−NH(アルキル)−、−N(アルキル)2−、−NH(アリール)−、−N(アルキル)2−、−F、−Cl、−Br、−I、−OH、−CF3、−NO2、−フェロセニル、−SO3H、−PO3H2の群から選択された他の置換基を有する。置換基の基アルキルは、1〜24個の炭素原子を有し、置換基の基アリールは、5〜24個の炭素原子を有する。
n−ブタン、イソブタン、1−ブテン、2−ブテン、イソブテン、1,3−ブタジエン、1,2−ブタジエンおよび場合によっては全部かまたは部分的に求核性試薬を含有するC4留分、
目的生成物(2,7−オクタジエニル誘導体)を有する留分、
副生成物を有する留分および/または
触媒を有する留分および
場合によっては求核性試薬を有する留分および/または
場合によっては溶剤留分。
水素化装置は、14mmの直径および2mの長さの寸法を有する注入される細流床型反応器を含み、外部に循環路を備えていた。この反応器は、電気的に加熱され、したがって反応は、断熱的に実施されることができた。触媒の体積は、0.307 lであった。触媒としては、銅−亜鉛触媒が使用された。Degussa社の型H9016のZnOペレット上のCu6%。入口温度は、30℃であり、反応器中の圧力は、水素で10バールに加圧された。C4炭化水素混合物の全供給量は、1853kgであった。選択的水素化は、英国特許第1066765号明細書の記載に関連して実施された。選択的水素化による生成物の組成は、第1表から確認することができる。4時間の試験時間後、ビニルアセチレンおよび1−ブチンの含量は、零に減少されており、1,3−ブタジエンおよび1,2−ブタジエンの含量は、本質的に変化しないことを明らかに確認することができる。
テロ重合に対する一般的な作業方法
100mlの揺動型管中で、保護ガス下にパラジウムアセチルアセトネート55.9mg(0.18ミリモル)および1,3−ビス(2,4,6−トリメチルフェニル)イミダゾリウム−o−クレソラート(kresolat)−o−クレゾール0.393g(0.75ミリモル)をメタノール50g(1.56モル)中に溶解した。Buechi社の3リットルのオートクレーブ中で、水浴中で40℃に昇温されたo−クレゾール6.72g(0.06モル)およびナトリウムメタノラート3.47g(0.06モル)をメタノール115g(3.59g)およびトリプロピレングリコール100g(0.52モル)中に溶解した。引続き、ガス圧ノズルを用いて、C4炭化水素混合物550gをオートクレーブ中に圧入した(C4貯蔵瓶中での質量損失による量測定)。このオートクレーブを撹拌下に反応温度に昇温させ、パラジウム含有溶液をオートクレーブ内容物に添加し、反応をオンラインガスクロマトグラフィーにより追跡した。反応時間は、14時間であった。
GC(第1のカラム:DB-WAX/Al2O3、第2のカラム:DB-Wax/HP-5MS;初期温度:50℃、最大温度:200℃、初期時間:1分間、平衡時間:3分間;温度プログラム:15℃/分で50℃から200℃へ、進行時間:11分間;注入:220℃、一定の流れ)。tR(C4−炭化水素)=2.762分、
tR(メタノール)=3.152分、tR(1,7−オクタジエン)=3.866分、tR(トランス−1,6−オクタジエン)=3.958分、tR(シス−1,6−オクタジエン)=4.030分、tR(シス−1,3,7−オクタトリエン)=4.291分、tR(トランス−1,3,7−オクタトリエン)=4.292分、tR(ビニルシクロヘキセン)=4.448分、tR(イソブタン)=4.552分、tR(n−ブタン)=4.822分、tR(3モード)=5.523分、tR(トランブテン)=6.116分、tR(1−ブテン)=6.240分、tR(イソブテン)=6.412分、tR(シス−ブテン)=6.616分、tR(1モード)=6.650分、tR(1,2−ブタジエン)=6.900分、tR(1,3−ブタジエン)=7.526分。2,7−オクタジエニル−1−メチルエーテル(=1モード)、1,7−オクタジエン−3−メチルエーテル(=3モード)。
本発明による本実施例において、実施例1からのC4炭化水素混合物を使用した。
本発明による本実施例において、1,3−ブタジエン43.53質量%、イソブタン1.95質量%、n−ブタン4.79質量%、トランス−ブテン4.58質量%、1−ブテン17.20質量%、イソブテン24.55質量%、シス−ブテン3.15質量%、1,2−ブタジエン0.1質量%を有する、アセチレン不含およびアレン含有のC4炭化水素混合物を使用した。
比較例において、1,3−ブタジエン43.19質量%、イソブタン1.73質量%、n−ブタン6.86質量%、トランス−ブテン5.12質量%、1−ブテン14.80質量%、イソブテン24.56質量%、シス−ブテン3.57質量%を有する、アセチレン含有およびアレン含有のC4炭化水素混合物を使用した。
比較例において、1,3−ブタジエン43.19質量%、イソブタン1.73質量%、n−ブタン6.86質量%、トランス−ブテン5.12質量%、1−ブテン14.80質量%、イソブテン24.56質量%、シス−ブテン3.57質量%、ビニルアセチレン0.0015質量%および1−ブチン0.0012質量%を有する、アセチレン含有およびアレン不含のC4炭化水素混合物を使用した。
この比較例において、1,3−ブタジエン43.53質量%、イソブタン1.95質量%、n−ブタン4.79質量%、トランス−ブテン4.58質量%、1−ブテン17.20質量%、イソブテン24.55質量%、シス−ブテン3.15質量%、1,2−ブタジエン0.11量%、ビニルアセチレン0.0017質量%および1−ブチン0.0010質量%を有する、アセチレン含有およびアレン含有のC4炭化水素混合物を使用した。
Claims (19)
- 式I
- 炭化水素流としてC4炭化水素留分を使用する、請求項1または2記載の方法。
- アセチレン系不飽和化合物を抽出によって分離する、請求項1から3までのいずれか1項に記載の方法。
- アセチレン系不飽和化合物を水素化によって除去する、請求項1から3までのいずれか1項に記載の方法。
- 水素化の際に銅含有触媒を使用する、請求項5記載の方法。
- 水素化の際にパラジウム含有触媒を使用する、請求項5記載の方法。
- 第1の処理工程の水素化搬出物として得られる炭化水素流から第2の処理工程(テロ重合)への供給前に4または5個を上廻る炭素原子を有する化合物を分離する、請求項5から7までのいずれか1項に記載の方法。
- 第1の処理工程の処理生成物として得られた炭化水素流を直接、エダクトとして第2の処理工程で使用する、請求項1から7までのいずれか1項に記載の方法。
- 第1の処理工程の処理生成物として得られた炭化水素流をブタジエン装置からのブタジエン流と混合し、この混合物を第2の処理工程で使用する、請求項1から8までのいずれか1項に記載の方法。
- テロ重合工程に供給される炭化水素混合物中で、アセチレン系不飽和化合物の含量は、50質量ppm未満である、請求項1から10までのいずれか1項に記載の方法。
- テロ重合工程に供給される炭化水素混合物中で、アセチレン系不飽和化合物の含量は、20質量ppm未満である、請求項11記載の方法。
- 求核性試薬として第2の処理工程で、メタノール、エタノール、2−エチルヘキサノール、オクタノール、オクテノール、オクタジエノール、イソプロパノール、n−プロパノール、イソブタノール、n−ブタノール、イソノナノール、蟻酸、酢酸、プロピオン酸、n−ブタン酸、イソブタン酸、安息香酸、フタル酸、フェノール、ジメチルアミン、メチルアミン、アンモニアまたは水を使用する、請求項1から12までのいずれか1項に記載の方法。
- 金属カルベン錯体をテロ重合触媒として第2の処理工程で使用する、請求項1から13までのいずれか1項に記載の方法。
- パラジウムカルベン錯体をテロ重合触媒として第2の処理工程で使用する、請求項14記載の方法。
- アレン系不飽和化合物を蒸留によりテロ重合搬出物から分離する、請求項1から15までのいずれか1項に記載の方法。
- 第2の処理工程の搬出物からC4留分を分離し、この留分からジエンを選択的水素化によって除去する、請求項1から15までのいずれか1項に記載の方法。
- 水素化C4留分、例えばラフィネートIを後処理する、請求項17記載の方法。
- 式I中のXがOR1aまたはNR1bを表わし、この場合
R1aは、H、メチル、エチル、n−プロピル、イソプロピル、第三ブチル、n−ブチル、第二ブチル、ペンチル、ヘキシル、ヘプチル、オクチル、オクテニル、オクタジエニル、イソノニル、2−エチルヘキシル、n−ノニル、フェニル、m−メチルフェニル、o−メチルフェニルまたはp−メチルフェニル、ナフチル、2,4−ジ−第三ブチルフェニル、2,6−ジ−第三ブチルメチルフェニル、ヒドロジェンカルボニル、メチルカルボニル、エチルカルボニル、プロピルカルボニルまたはフェニルカルボニルであり、および
R1bは、H、メチル、エチル、n−プロピル、イソプロピル、第三ブチル、n−ブチル、第二ブチル、ペンチル、ヘキシル、ヘプチル、オクチル、オクテニル、オクタジエニル、イソノニル、2−エチルヘキシル、n−ノニル、フェニル、m−クレシル、o−クレシルまたはp−クレシル、ナフチル、2,4−ジ−第三ブチルフェニル、2,6−ジ−第三ブチルメチルフェニル、ヒドロジェンカルボニル、メチルカルボニル、エチルカルボニル、プロピルカルボニルまたはフェニルカルボニルである、請求項1から18までのいずれか1項に記載の方法。
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2005
- 2005-08-01 DE DE102005036039A patent/DE102005036039A1/de not_active Withdrawn
- 2005-08-23 ES ES05787140T patent/ES2302231T3/es active Active
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- 2005-08-23 US US11/574,063 patent/US7462745B2/en not_active Expired - Fee Related
- 2005-08-23 AT AT05787140T patent/ATE388930T1/de not_active IP Right Cessation
- 2005-08-23 PL PL05787140T patent/PL1781588T3/pl unknown
- 2005-08-23 BR BRPI0515120-1A patent/BRPI0515120A/pt not_active Application Discontinuation
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- 2005-08-23 KR KR1020077004735A patent/KR101108382B1/ko not_active IP Right Cessation
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- 2005-08-26 TW TW094129307A patent/TWI374873B/zh not_active IP Right Cessation
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014519478A (ja) * | 2011-04-04 | 2014-08-14 | エボニック デグサ ゲーエムベーハー | 1−ブテンおよび1,3−ブタジエン誘導体の製造方法 |
Also Published As
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NO20071629L (no) | 2007-03-28 |
KR101108382B1 (ko) | 2012-01-30 |
PL1781588T3 (pl) | 2008-08-29 |
DE102005036039A1 (de) | 2006-03-02 |
KR20070045301A (ko) | 2007-05-02 |
EP1781588B1 (de) | 2008-03-12 |
BRPI0515120A (pt) | 2008-07-08 |
US7462745B2 (en) | 2008-12-09 |
DE502005003233D1 (de) | 2008-04-24 |
TWI374873B (en) | 2012-10-21 |
ATE388930T1 (de) | 2008-03-15 |
EP1781588A1 (de) | 2007-05-09 |
CA2576819A1 (en) | 2006-03-09 |
ES2302231T3 (es) | 2008-07-01 |
US20080021234A1 (en) | 2008-01-24 |
MX2007002106A (es) | 2007-03-30 |
WO2006024614A1 (de) | 2006-03-09 |
CA2576819C (en) | 2012-12-04 |
TW200615253A (en) | 2006-05-16 |
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