JP4705416B2 - イソブテンを含有する炭化水素混合物からt−ブタノールを製造する方法 - Google Patents
イソブテンを含有する炭化水素混合物からt−ブタノールを製造する方法 Download PDFInfo
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- JP4705416B2 JP4705416B2 JP2005184097A JP2005184097A JP4705416B2 JP 4705416 B2 JP4705416 B2 JP 4705416B2 JP 2005184097 A JP2005184097 A JP 2005184097A JP 2005184097 A JP2005184097 A JP 2005184097A JP 4705416 B2 JP4705416 B2 JP 4705416B2
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 title claims description 246
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims description 189
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- 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
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- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
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Classifications
-
- 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
- C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
- C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/12—Monohydroxylic acyclic alcohols containing four carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
a)第一の反応器に期間aの間に混合物(I)を送入する。同時に第二の反応器に、期間bの間に混合物(II)を送入し、かつ引き続き、期間cの間に混合物(I)を送入し、その際、期間bおよびcの合計は、期間aに相応する。ここから全サイクル時間aの場合、(a+c)/bのサイクル時間の比が生じる。
n−ブタン 15.4質量%、
イソブタン 1.4質量%、
1−ブテン 31.3質量%、
2−ブテン(シスおよびトランス) 46.6質量%、
イソブテン 5.3質量%。
反応器に混合物(Xa)および(Xb)を交互に送入した。サイクル時間は4時間であった。つまり最初の4時間で混合物(Xa)を供給し、次の4時間で混合物(Xb)を、その後の4時間でふたたび混合物(Xa)を、などと供給した。供給速度は混合物(Xa)に関して47g/hであり、かつ混合物(Xb)に関しては61.6g/hであった。混合物を48時間(混合物(Xa)を6サイクル時間および混合物(Xb)を6サイクル時間)回収し、かつその後、この混合物から平均的な分析が得られた。
イソブテン 4.19、
残りのC4 81.95、
TBA 10.62、
水 3.04、
その他の物質 0.2。
反応器中に使用混合物(Xc)を供給した。供給速度は54.3g/hであった。48hの反応搬出物を回収し、かつ平均的な分析が得られた。
イソブテン 4.40、
残りのC4 81.95、
TBA 10.33、
水 3.11、
その他の物質 0.21。
Claims (19)
- イソブテンを含有する炭化水素混合物と水とを固体の酸性触媒を用いて反応器カスケード中で反応させることによりt−ブタノール(TBA)を製造する方法において、少なくとも1つの反応器に2つの異なったイソブテン含有炭化水素混合物を交互に送入し、その際、該混合物の一方が、他方の混合物よりも高いt−ブタノール含有率および高い含水率を有することを特徴とする、t−ブタノール(TBA)を製造する方法。
- より少ないt−ブタノール含有率を有する炭化水素混合物が1質量%より少ないt−ブタノールを含有する、請求項1記載の方法。
- より少ないt−ブタノール含有率を有する炭化水素混合物が0.1質量%より少ないt−ブタノールを含有する、請求項2記載の方法。
- より少ないt−ブタノール含有率を有する炭化水素混合物が1〜30質量%のイソブテンの含有率を有する、請求項1記載の方法。
- より少ないt−ブタノール含有率を有する炭化水素混合物が、炭化水素混合物中で可溶性である含有率を最大で10%超える水の含有率を有する、請求項1から4までのいずれか1項記載の方法。
- イソブテンを含有する2つの異なった混合物を反応器に交互に送入する、請求項1から5までのいずれか1項記載の方法。
- 1つの反応器ユニットを形成する2つの、互いに並列接続された反応器に、2つの異なったイソブテンを含有する混合物を交互に送入する、請求項1から5までのいずれか1項記載の方法。
- 交互に運転される反応器の、交互の送入により得られる両方の異なった反応搬出物を一緒に蒸留ユニット中で、炭化水素を含有する流と、粗製t−ブタノールとに分離する、請求項1から7までのいずれか1項記載の方法。
- 交互に運転される反応器の、交互の送入により得られる両方の異なった反応搬出物を別々に、2つの蒸留ユニット中で、炭化水素を含有する流と、粗製t−ブタノールとに分離し、かつより高いイソブテン含有率を有する塔頂生成物を、交互に運転される反応器の送入のために使用する、請求項1から7までのいずれか1項記載の方法。
- 少なくとも2つの反応器または反応器ユニットを交互に運転する、請求項1から9までのいずれか1項記載の方法。
- 混合物の交換が0.5〜10時間のサイクルで行われるように、反応器に交互に送入する、請求項1から10までのいずれか1項記載の方法。
- 水およびTBAがより少ない混合物による送入に対する、水およびTBAがより富化された混合物による反応器の送入の時間的な比率が、1以上である、請求項1から11までのいずれか1項記載の方法。
- 水およびTBAがより富化された混合物による反応器の送入対水およびTBAがより少ない混合物による反応器の送入の時間的な比率を、1.5対1〜2.5対1に調節する、請求項12記載の方法。
- 方法を30〜120℃の温度で実施する、請求項1から13までのいずれか1項記載の方法。
- 反応器カスケードの第一の反応器へ、25質量%より大きいイソブテンの含有率を有する炭化水素混合物を供給する、請求項1から14までのいずれか1項記載の方法。
- 交互に運転されない反応器カスケードの反応器において、それぞれの反応器への反応混合物の導入前に水を供給する、請求項1から15までのいずれか1項記載の方法。
- 反応器カスケードの全ての反応器を、10Kより小さい反応器入口から反応器出口への反応混合物の温度差で運転する、請求項1から16までのいずれか1項記載の方法。
- 触媒として、1〜60m/hの線速度で運転される反応器中で、0.1〜5mmの平均粒径を有するイオン交換樹脂を使用する、請求項1から17までのいずれか1項記載の方法。
- 2つの異なったイソブテンを含有する炭化水素混合物が交互に送入され、その際、該混合物の一方は他方の混合物よりも高いt−ブタノール含有率および高い含水率を有する反応器が、反応器カスケードの最後の反応器であるか、または並列接続された2つ以上の反応器からなる最後の反応器ユニットである、請求項1から18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 |
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DE102004030943.4 | 2004-06-26 | ||
DE102004030943A DE102004030943B4 (de) | 2004-06-26 | 2004-06-26 | Verfahren zur Herstellung von tert.-Butanol aus Isobuten-haltigen Kohlenwasserstoffgemischen |
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JP2006008689A JP2006008689A (ja) | 2006-01-12 |
JP4705416B2 true JP4705416B2 (ja) | 2011-06-22 |
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Country Status (10)
Country | Link |
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US (1) | US7002050B2 (ja) |
EP (1) | EP1616848B1 (ja) |
JP (1) | JP4705416B2 (ja) |
KR (1) | KR101157813B1 (ja) |
CN (1) | CN100410223C (ja) |
DE (1) | DE102004030943B4 (ja) |
ES (1) | ES2456668T3 (ja) |
PL (1) | PL1616848T3 (ja) |
SG (1) | SG118303A1 (ja) |
TW (1) | TW200611889A (ja) |
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US7838708B2 (en) | 2001-06-20 | 2010-11-23 | Grt, Inc. | Hydrocarbon conversion process improvements |
JP2007525477A (ja) | 2003-07-15 | 2007-09-06 | ジーアールティー インコーポレイテッド | 炭化水素の合成 |
US20050171393A1 (en) | 2003-07-15 | 2005-08-04 | Lorkovic Ivan M. | Hydrocarbon synthesis |
US7674941B2 (en) | 2004-04-16 | 2010-03-09 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
US8642822B2 (en) | 2004-04-16 | 2014-02-04 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor |
US20060100469A1 (en) | 2004-04-16 | 2006-05-11 | Waycuilis John J | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
US8173851B2 (en) | 2004-04-16 | 2012-05-08 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
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2005
- 2005-02-04 SG SG200500716A patent/SG118303A1/en unknown
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- 2005-05-02 ES ES05103618.4T patent/ES2456668T3/es active Active
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Also Published As
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DE102004030943B4 (de) | 2013-10-02 |
JP2006008689A (ja) | 2006-01-12 |
TW200611889A (en) | 2006-04-16 |
US20050288534A1 (en) | 2005-12-29 |
EP1616848B1 (de) | 2014-01-22 |
EP1616848A2 (de) | 2006-01-18 |
ES2456668T3 (es) | 2014-04-23 |
EP1616848A3 (de) | 2006-04-19 |
DE102004030943A1 (de) | 2006-01-12 |
SG118303A1 (en) | 2006-01-27 |
KR101157813B1 (ko) | 2012-07-02 |
PL1616848T3 (pl) | 2014-06-30 |
US7002050B2 (en) | 2006-02-21 |
KR20060049702A (ko) | 2006-05-19 |
CN100410223C (zh) | 2008-08-13 |
CN1712391A (zh) | 2005-12-28 |
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