JP5015447B2 - シアノヒドリンに関連する化学反応のための改善された方法 - Google Patents
シアノヒドリンに関連する化学反応のための改善された方法 Download PDFInfo
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- 238000000034 method Methods 0.000 title claims description 58
- 238000006460 hydrolysis reaction Methods 0.000 claims description 108
- 239000000203 mixture Substances 0.000 claims description 82
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- 239000000376 reactant Substances 0.000 claims description 72
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- DRYMMXUBDRJPDS-UHFFFAOYSA-N 2-hydroxy-2-methylpropanamide Chemical compound CC(C)(O)C(N)=O DRYMMXUBDRJPDS-UHFFFAOYSA-N 0.000 claims description 13
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- BFSIDIWZBQSIHF-UHFFFAOYSA-N 2-oxopropane-1,3-disulfonic acid Chemical compound OS(=O)(=O)CC(=O)CS(O)(=O)=O BFSIDIWZBQSIHF-UHFFFAOYSA-N 0.000 description 2
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- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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- 241000364021 Tulsa Species 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
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- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940030980 inova Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- LYGJENNIWJXYER-FIBGUPNXSA-N nitromethane-d3 Chemical compound [2H]C([2H])([2H])[N+]([O-])=O LYGJENNIWJXYER-FIBGUPNXSA-N 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
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- LBZIXWRZFXPLJU-UHFFFAOYSA-N propan-2-one;sulfuric acid Chemical compound CC(C)=O.OS(O)(=O)=O LBZIXWRZFXPLJU-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
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- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/26—Nozzle-type reactors, i.e. the distribution of the initial reactants within the reactor is effected by their introduction or injection through nozzles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/32—Packing elements in the form of grids or built-up elements for forming a unit or module inside the apparatus for mass or heat transfer
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/06—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
図1は、反応プロセスがアセトンシアノヒドリンの酸での加水分解反応である本発明の実施形態の概略図である。
図2は、比較のために提供される、アセトンシアノヒドリンの酸での加水分解の公知従来技術のプロセスの概略図である。
比較例−従来法
Kirk−Othmerおよび米国特許‘093に開示されているタイプの第一加水分解プロセス(従来技術)を図2により示し、直列に並んだ2つのCSTRリアクターを含んでいた。このシステムは、H2SO4:ACHモル比が1.48、ACH添加分割比が2.3:1で操作され、ここにおいて全ACHフィードの70重量%が第一反応段階に添加され、全ACHフィードの30重量%が第二反応段階に添加された。硫酸を99.5%の濃度で、そしてACHを98.5%の濃度でこのシステムにおける反応物質として使用した。
本発明の方法による改善された加水分解システム(発明)を図1により示し、2つの連続流反応段階を含んでいた。このシステムは、前記実施例1のCSTRベースの加水分解システムに使用したのと同じ条件下で操作された。
2 インジェクター第二組
3、4、5、7、8、203、204、205 第一段階循環パイプ
6 硫酸
T8、T18、T20、T60、T230、T260 熱電対
9 アセトン中PTZ阻害剤溶液
10、50 ACH混合装置
11、12、49、99、209、219 流れ
13、15、17、18、213、214、215 第二段階循環パイプ
14 脱気容器の底部(第二段階循環パイプ)
16 任意の硫酸
19 任意のアセトン中PTZ阻害剤溶液
20 第一段階脱気装置
30、70、210、240 遠心ポンプ
40、80、220、250 熱交換器
60 第二段階脱気装置
100 クラッカーリアクター
201、211 第一ディップパイプ
202 第二ディップパイプ
212 任意の液面下硫酸
230 第一反応段階CSTR
260 第二反応段階CSTR
Claims (9)
- ある量の熱を生じさせる、シアノヒドリンに関連する発熱反応プロセスにおいて、シアノヒドリンの分解を最小限にする方法であって:
当該方法が
(a)少なくとも1つの反応ゾーンをその中に含み、かつ前記の少なくとも1つの反応ゾーンに位置する内部混合手段を有する管状リアクターに反応媒体を提供する工程;
(b)1以上の反応物質を前記管状リアクターに提供する工程;
(c)前記反応媒体を1以上の反応物質と、前記の少なくとも1つの反応ゾーンにおいて混合し、これにより実質的に均一な組成および実質的に均一な反応温度を有するバルク反応混合物を形成する工程;
(d)発熱反応プロセスからある量の熱を除去する工程であって、前記の熱の量が発熱反応プロセスにより生じる熱の量と等しいものである工程;
(e)前記の少なくとも1つの反応ゾーンにおいて前記の1以上の反応物質を反応させて、バルク温度を有する混合生成物を製造する工程;および
(f)前記工程(e)により反応ゾーンに形成された混合物の一部を前記管状リアクターに循環させる工程を含み、
前記シアノヒドリンに関連する反応プロセスが加水分解反応であり、第一反応物質が、アセトンシアノヒドリンを含み、第二反応物質が硫酸を含み、並びに、
前記ある量の熱を除去する工程の前に、少なくとも前記第二反応物質を、前記反応ゾーンに形成された混合物の一部にまず添加することにより、少なくとも前記第二反応物質が前記管状リアクターに間接的に提供され、前記ある量の熱を除去する工程が、前記反応媒体を前記管状リアクターに提供する前に行われる方法。 - ある量の熱を除去する工程が、前記反応媒体を前記管状リアクターに提供する前に、前記反応媒体を前記バルク温度よりも1℃から10℃低い温度に冷却することにより行われる請求項1記載の方法。
- 前記反応媒体および前記の1以上の反応物質が、2:1から200:1の間の反応媒体:反応物質の比で提供される請求項1記載の方法。
- 前記の1以上の反応物質の少なくとも第一のものが前記管状リアクターに、複数の添加点の少なくとも1つにおいて、前記管状リアクター装置の周りの円周に位置する、複数のインジェクター装置により提供される請求項1記載の方法。
- 前記の1以上の反応物質の少なくとも第一のものを前記管状リアクターに提供するために、前記の複数のインジェクター装置の1以上を選択し、使用することにより、反応媒体を1以上の反応物質と混合する工程が、少なくとも部分的に達成される請求項4記載の方法。
- 前記内部混合手段が:スタティックミキサー、オリフィスプレート、ベンチュリ、ジェットミキサー、エダクター、多孔板、スパージャー、アジテーター、ロータリーミキサー、高速循環ループ、およびスプレーノズル;からなる群から選択される少なくとも1つの装置である請求項1記載の方法。
- 前記管状リアクターが、少なくとも2つの管状リアクターを含む請求項1記載の方法。
- バルク反応混合物中に存在する酸:アセトンシアノヒドリンのモル比が、1.3:1〜1.9:1の範囲である請求項1記載の方法。
- 前記加水分解反応の前記混合生成物が:α−スルファトイソブチルアミド、α−ヒドロキシイソブチルアミド、およびメタクリルアミドからなる群から選択される1以上の生成物を含み:
方法が
(g)クラッカーリアクター中で加水分解反応からの混合生成物を熱変換させて、メタクリルアミドおよびメタクリル酸を含むクラッカーリアクター混合物を製造する工程;および
(h)少なくとも1つのリアクター中でクラッカーリアクター混合物を、アルカノールおよび水から選択される物質と反応させて、メタクリル酸およびそのエステルから選択されるモノマーを製造する工程をさらに含む、請求項1記載の方法。
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US63087204P | 2004-11-24 | 2004-11-24 | |
US60/630872 | 2004-11-24 |
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JP2006143732A JP2006143732A (ja) | 2006-06-08 |
JP5015447B2 true JP5015447B2 (ja) | 2012-08-29 |
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Country Status (9)
Country | Link |
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US (2) | US7582790B2 (ja) |
EP (1) | EP1666451B1 (ja) |
JP (1) | JP5015447B2 (ja) |
KR (1) | KR100724716B1 (ja) |
CN (1) | CN100363335C (ja) |
BR (1) | BRPI0505097B1 (ja) |
DE (1) | DE602005003912T2 (ja) |
ES (1) | ES2297637T3 (ja) |
TW (1) | TWI277444B (ja) |
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Publication number | Priority date | Publication date | Assignee | Title |
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HU3201U (en) * | 2006-02-08 | 2006-12-28 | Csokai Viktor Dr | Apparatus for recycling of pvc |
DE102006058249A1 (de) * | 2006-12-08 | 2008-06-12 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Cyanhydrinen sowie deren Verwendung bei der Herstellung von Methacrylsäurealkylestern |
DE102006059512A1 (de) * | 2006-12-14 | 2008-06-19 | Evonik Röhm Gmbh | Destillative Aufarbeitung von Acetoncyanhydrin und Verfahren zur Herstellung von Metharcylsäureesther und Nachfolgeprodukten |
DE102006059511A1 (de) * | 2006-12-14 | 2008-06-19 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Acetoncyanhydrin und dessen Folgeprodukten durch gezielte Kühlung |
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DE765734C (de) | 1941-12-04 | 1952-12-22 | Roehm & Haas G M B H | Verfahren zur Herstellung von Methacrylsaeureverbindungen |
DE1163800B (de) | 1958-12-09 | 1964-02-27 | Degussa | Verfahren zur Herstellung von Methacrylsaeureamidsulfat durch Umsetzung von Acetoncyanhydrin mit Schwefelsaeure |
DE3541253A1 (de) | 1985-11-22 | 1987-05-27 | Degussa | Verfahren zur herstellung von methacrylamid |
US5763687A (en) * | 1995-12-15 | 1998-06-09 | Mitsui Chemicals, Inc. | Preparation process for aromatic mononitro compounds |
FR2796939B1 (fr) | 1999-07-29 | 2001-09-14 | Atofina | Procede de fabrication de la cyanhydrine de la methyl ethyl cetone |
ZA200303241B (en) | 2002-05-01 | 2003-11-04 | Rohm & Haas | Improved process for methacrylic acid and methcrylic acid ester production. |
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DE602005003912D1 (de) | 2008-01-31 |
DE602005003912T2 (de) | 2008-12-04 |
BRPI0505097A (pt) | 2006-07-04 |
KR100724716B1 (ko) | 2007-06-04 |
EP1666451B1 (en) | 2007-12-19 |
US7582790B2 (en) | 2009-09-01 |
CN100363335C (zh) | 2008-01-23 |
EP1666451A1 (en) | 2006-06-07 |
US20060111586A1 (en) | 2006-05-25 |
US20090082587A1 (en) | 2009-03-26 |
JP2006143732A (ja) | 2006-06-08 |
TWI277444B (en) | 2007-04-01 |
KR20060058012A (ko) | 2006-05-29 |
TW200624162A (en) | 2006-07-16 |
CN1778791A (zh) | 2006-05-31 |
BRPI0505097B1 (pt) | 2020-12-01 |
US7763746B2 (en) | 2010-07-27 |
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