JP5441025B2 - ジシクロペンタジエンの精製方法 - Google Patents
ジシクロペンタジエンの精製方法 Download PDFInfo
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- JP5441025B2 JP5441025B2 JP2008333241A JP2008333241A JP5441025B2 JP 5441025 B2 JP5441025 B2 JP 5441025B2 JP 2008333241 A JP2008333241 A JP 2008333241A JP 2008333241 A JP2008333241 A JP 2008333241A JP 5441025 B2 JP5441025 B2 JP 5441025B2
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- Prior art keywords
- dicyclopentadiene
- fraction
- crude
- distillation column
- distillation
- Prior art date
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- 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 title claims description 127
- 238000000034 method Methods 0.000 title claims description 28
- 238000004821 distillation Methods 0.000 claims description 64
- 239000007789 gas Substances 0.000 claims description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 239000011261 inert gas Substances 0.000 claims description 9
- -1 methyl dicyclopentadiene Chemical compound 0.000 claims description 9
- 238000006471 dimerization reaction Methods 0.000 claims description 8
- 239000002994 raw material Substances 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- 238000000746 purification Methods 0.000 description 23
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 14
- 238000011084 recovery Methods 0.000 description 14
- 239000007788 liquid Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 description 4
- PPWUTZVGSFPZOC-UHFFFAOYSA-N 1-methyl-2,3,3a,4-tetrahydro-1h-indene Chemical compound C1C=CC=C2C(C)CCC21 PPWUTZVGSFPZOC-UHFFFAOYSA-N 0.000 description 3
- 241001550224 Apha Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000000447 dimerizing effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000007858 starting material Substances 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
ジシクロペンタジエン(DCPD)
LPGクラッカーで副生した分解ガソリンの二量化反応による反応生成物からC5留分及びBTX留分を除去することにより得られた表2に示す組成を有する粗ジシクロペンタジエンを用意した。
実施例1と同様の蒸留塔(理論段数20段)に、予め80℃に加熱した上記の粗ジシクロペンタジエンを100g/minの流量で供給し、塔頂における圧力12.5kPaA及び還流比40とした。第1の留分は塔頂から5段目の位置でサイドカット抜き出しとし、流量66g/minで回収した。また、塔頂からの回収量は8g/min、塔底からは第2の留分を26g/minの流量で回収した。このときの塔頂温度は103℃、塔底温度は124℃であった。第1の留分におけるジシクロペンタジエンの含有量は、93.3質量%であった。また、第1の留分の色相は、APHAで60であった。
Claims (5)
- C2留分、C3留分及びC4留分を原料とするエチレンプラントで副生した分解ガソリンの二量化反応による反応生成物からC5留分及びBTX留分を除去してなる、ジシクロペンタジエンを含む粗ジシクロペンタジエン、
を蒸留することによりジシクロペンタジエンを分離回収する、ジシクロペンタジエンの精製方法であって、
前記粗ジシクロペンタジエンが、メチルジシクロペンタジエンを10〜40質量%含有するものであり、
分離回収されたジシクロペンタジエンにおけるメチルジシクロペンタジエンの含有量が1.0質量%未満となるように前記粗ジシクロペンタジエンを蒸留する、ジシクロペンタジエンの精製方法。 - 前記粗ジシクロペンタジエンの蒸留を理論段数30〜60段の蒸留塔により行う、請求項1に記載のジシクロペンタジエンの精製方法。
- 前記粗ジシクロペンタジエンにおけるジシクロペンタジエンの含有量が40〜90質量%であり、
分離回収されたジシクロペンタジエンの純度が93質量%以上となるように前記粗ジシクロペンタジエンを蒸留する、請求項1又は2に記載のジシクロペンタジエンの精製方法。 - 前記粗ジシクロペンタジエンを130℃以下で蒸留する、請求項1〜3のいずれか一項に記載のジシクロペンタジエンの精製方法。
- 前記粗ジシクロペンタジエンを蒸留することにより、ジシクロペンタジエンを含む第1の留分と、該第1の留分よりも軽質な軽質留分とを得るステップと、
前記軽質留分と、不活性ガス又は炭素数1〜3の炭化水素ガスと、を接触させるステップと、
を備える、請求項1〜4のいずれか一項に記載のジシクロペンタジエンの精製方法。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008333241A JP5441025B2 (ja) | 2008-12-26 | 2008-12-26 | ジシクロペンタジエンの精製方法 |
CA2748247A CA2748247C (en) | 2008-12-26 | 2009-11-11 | Method for refining dicyclopentadiene |
US13/141,145 US9242909B2 (en) | 2008-12-26 | 2009-11-11 | Method for refining dicyclopentadiene |
PCT/JP2009/069210 WO2010073841A1 (ja) | 2008-12-26 | 2009-11-11 | ジシクロペンタジエンの精製方法 |
US14/962,512 US9783469B2 (en) | 2008-12-26 | 2015-12-08 | Method for refining dicyclopentadiene |
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JP2008333241A JP5441025B2 (ja) | 2008-12-26 | 2008-12-26 | ジシクロペンタジエンの精製方法 |
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JP2010150224A JP2010150224A (ja) | 2010-07-08 |
JP5441025B2 true JP5441025B2 (ja) | 2014-03-12 |
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JP2008333241A Active JP5441025B2 (ja) | 2008-12-26 | 2008-12-26 | ジシクロペンタジエンの精製方法 |
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Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2011256156A (ja) * | 2010-05-12 | 2011-12-22 | Mitsubishi Chemicals Corp | 蒸留塔の温度制御方法 |
WO2020014040A1 (en) * | 2018-07-13 | 2020-01-16 | Momentive Performance Materials Inc. | Preparation of isocyanatosilanes |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5764622A (en) * | 1980-10-06 | 1982-04-19 | Mitsui Toatsu Chem Inc | Separating method of dicyclopentadiene |
JPH0739354B2 (ja) * | 1985-07-08 | 1995-05-01 | 日本ゼオン株式会社 | 高純度ジシクロペンタジエンの製造方法 |
JPH0832642B2 (ja) * | 1987-01-13 | 1996-03-29 | 日本ゼオン株式会社 | ジシクロペンタジエンの精製法 |
JP2905910B2 (ja) * | 1991-04-18 | 1999-06-14 | 丸善石油化学株式会社 | ジシクロペンタジエンの気相熱分解方法および高純度ジシクロペンタジエンの製造方法 |
US5254781A (en) * | 1991-12-31 | 1993-10-19 | Amoco Corporation | Olefins process which combines hydrocarbon cracking with coupling methane |
DE10000889C2 (de) * | 2000-01-12 | 2002-12-19 | Mg Technologies Ag | Verfahren zum Erzeugen von C¶2¶- und C¶3¶-Olefinen aus Kohlenwasserstoffen |
TW583178B (en) * | 2001-09-29 | 2004-04-11 | China Petrochemical Corp | Process for separating C5 cuts obtained from a petroleum cracking process |
EP2017245A1 (en) * | 2006-05-10 | 2009-01-21 | Idemitsu Kosan Co., Ltd. | Process for production of dicyclopentadiene |
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