JP5027544B2 - テトラシクロドデセンの製造方法 - Google Patents
テトラシクロドデセンの製造方法 Download PDFInfo
- Publication number
- JP5027544B2 JP5027544B2 JP2007093197A JP2007093197A JP5027544B2 JP 5027544 B2 JP5027544 B2 JP 5027544B2 JP 2007093197 A JP2007093197 A JP 2007093197A JP 2007093197 A JP2007093197 A JP 2007093197A JP 5027544 B2 JP5027544 B2 JP 5027544B2
- Authority
- JP
- Japan
- Prior art keywords
- tetracyclododecene
- dicyclopentadiene
- exhaust gas
- norbornene
- raw material
- 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.)
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- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 title claims description 42
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 46
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 37
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 28
- 239000002994 raw material Substances 0.000 claims description 26
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 17
- 239000005977 Ethylene Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 239000007788 liquid Substances 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 4
- 239000012295 chemical reaction liquid Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 2
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000007789 gas Substances 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 8
- 239000012535 impurity Substances 0.000 description 7
- 239000000295 fuel oil Substances 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 238000005698 Diels-Alder reaction Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- -1 propenyl norbornene Chemical compound 0.000 description 2
- APYBVJQVVPJCEB-UHFFFAOYSA-N 1-cyclonona-1,3-dien-1-yl-2-methylcyclonona-1,3-diene Chemical compound C1CCCCC=CC(C)=C1C1=CC=CCCCCC1 APYBVJQVVPJCEB-UHFFFAOYSA-N 0.000 description 1
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- HYPABJGVBDSCIT-UPHRSURJSA-N cyclododecene Chemical compound C1CCCCC\C=C/CCCC1 HYPABJGVBDSCIT-UPHRSURJSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(A)シクロペンタジエンとエチレンとの反応によりノルボルネンを生成する下記反応(1)
ガス吸収塔で排ガスをジシクロペンタジエンに吸収させた。そのときの底部温度34℃、塔頂温度32℃、圧力は常圧で行った。排ガスの流量80m3/時間、ジシクロペンタジエンの流量11.2m3/時間であった。
各成分の分析はガスクロマトグラフィーで行った。
カラム:DB−1、 30m
昇温条件:50℃→10℃/min→230℃(10min)
INJ温度:250℃、検出器温度:250℃
検出器:FID、キャリアーガス:He
Claims (7)
- エチレン、シクロペンタジエン又はジシクロペンタジエン、およびノルボルネンを原料成分として連続供給してテトラシクロドデセンを製造する方法において、反応器からの排ガス中に含まれる前記原料成分をジシクロペンタジエンに吸収させ、該原料成分を吸収したジシクロペンタジエンを原料として反応器に供給することを特徴とするテトラシクロドデセンの製造方法。
- 前記反応器からの排ガス中に含まれる前記原料成分をスクラバー中のジシクロペンタジエンに吸収させることを特徴とする請求項1に記載のテトラシクロドデセンの製造方法。
- 前記反応器からの排ガスが反応液の気液分離処理の気体成分であることを特徴とする請求項1に記載のテトラシクロドデセンの製造方法。
- 前記反応器からの排ガスが、さらに、ノルボルネン及びテトラシクロドデセン混合物の蒸留精製の蒸留塔頂部からの成分を含むことを特徴とする請求項3に記載のテトラシクロドデセンの製造方法。
- ジシクロペンタジエンに吸収される前記原料成分がノルボルネンである請求項1に記載のテトラシクロドデセンの製造方法。
- 前記排ガス中に含まれるノルボルネンの回収率が90%以上であることを特徴とする請求項5に記載のテトラシクロドデセンの製造方法。
- 前記反応器からの排ガス中の前記原料成分をジシクロペンタジエンに吸収させた後の排ガス中に含まれるエチレンを回収し、原料として使用することを特徴とする請求項1に記載のテトラシクロドデセンの製造方法。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007093197A JP5027544B2 (ja) | 2007-03-30 | 2007-03-30 | テトラシクロドデセンの製造方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007093197A JP5027544B2 (ja) | 2007-03-30 | 2007-03-30 | テトラシクロドデセンの製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008247851A JP2008247851A (ja) | 2008-10-16 |
JP5027544B2 true JP5027544B2 (ja) | 2012-09-19 |
Family
ID=39973232
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007093197A Active JP5027544B2 (ja) | 2007-03-30 | 2007-03-30 | テトラシクロドデセンの製造方法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP5027544B2 (ja) |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2771735B1 (fr) * | 1997-12-02 | 2000-03-03 | Atochem Elf Sa | Procede et reacteur pour la fabrication du norbornene |
JP3991650B2 (ja) * | 2001-10-26 | 2007-10-17 | 日本ゼオン株式会社 | ノルボルネン及びテトラシクロドデセンの同時製造方法 |
JP2003286204A (ja) * | 2002-03-27 | 2003-10-10 | Nippon Zeon Co Ltd | ノルボルネン系化合物の製造方法 |
-
2007
- 2007-03-30 JP JP2007093197A patent/JP5027544B2/ja active Active
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JP2008247851A (ja) | 2008-10-16 |
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