TWI707841B - 使用甲酸和甲醇之甲氧羰基化反應 - Google Patents
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- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
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- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
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Abstract
一種使用甲酸和甲醇之甲氧羰基化反應的方法。
Description
本發明係關於一種使用甲酸和甲醇之甲氧羰基化反應的方法。
本發明之目的是要提供一種利用CO氣體以外之CO源之方法,將該CO源導入該反應槽中。該方法將獲得高產率的甲酯。 本發明之目的係藉由根據申請專利範圍第1項的方法達成。 該方法為一種包含下列步驟之方法: a)添加烯烴; b)添加包含Pd之化合物,其中該Pd能形成錯合物; c)添加通式(I
)之化合物:其中R1
、R2
、R3
、R4
各自獨立選自:-H、-(C1
-C12
)-烷基、-O-(C1
-C12
)-烷基、-(C4
-C14
)-芳基、-O-(C4
-C14
)-芳基、環烷基、-(C1
-C12
)-雜烷基、-O-(C1
-C12
)-雜烷基、 -(C3
-C14
)-雜芳基、-O-(C3
-C14
)-雜芳基、-COO-烷基、 -COO-芳基、-C-O-烷基、-C-O-芳基、NH2
、鹵素,且該等殘基也能形成較大縮合環; 其中該經列舉之烷基基團、芳基基團、環烷基、雜烷基基團、雜芳基基團可經下列取代: -(C1
-C12
)-烷基、-O-(C1
-C12
)-烷基、鹵素; 且該等基團R1
、R2
、R3
、R4
中之至少一者不表示苯基; d)添加MeOH; e)添加HCOOH, 其中基於2 mmol烯烴,所使用的體積是在0.3 ml至0.8 ml之範圍中; f)加熱該反應混合物以轉變該烯烴成甲酯。 在該方法之一變化型中,不供應CO至該反應混合物。 在該方法之一變化型中,HCOOH用作為該反應之唯一CO來源。 在該方法之一變化型中,在方法步驟b)中之該化合物係選自:Pd(acac)2
、PdCl2
、Pd(dba)3
*CH3
Cl (dba=二亞苄基丙酮)、Pd(OAc)2
、Pd(TFA)2
、Pd(CH3
CN)Cl2
。 在該方法之一變化型中,在方法步驟b)中之該化合物係Pd(OAc)2
。 在該方法之一變化型中,該方法包含額外的方法步驟g): g)添加酸。 在該方法之一變化型中,該酸係選自:H2
SO4
、CH3
SO3
H、CF3
SO3
H、PTSA (對-甲苯磺酸)。 在該方法之一變化型中,該酸是PTSA(對-甲苯磺酸)。 在該方法之一變化型中,基於2 mmol烯烴,HCOOH的使用體積是在0.4 ml至0.6 ml之範圍中。 在該方法之一變化型中,R1
、R2
、R3
、R4
各自獨立選自:-(C1
-C12
)-烷基、-O-(C1
-C12
)-烷基、-(C4
-C14
)-芳基、 -O-(C4
-C14
)-芳基、環烷基、-(C1
-C12
)-雜烷基、-O-(C1
-C12
)-雜烷基、-(C3
-C14
)-雜芳基、-O-(C3
-C14
)-雜芳基、 -COO-烷基、-COO-芳基、-C-O-烷基、-C-O-芳基、NH2
、鹵素,且該等殘基也能形成較大縮合環; 其中該經列舉之烷基基團、芳基基團、環烷基、雜烷基基團、雜芳基基團可經下列取代: -(C1
-C12
)-烷基、-O-(C1
-C12
)-烷基、鹵素; 且該等基團R1
、R2
、R3
、R4
中之至少一者不表示苯基。 在該方法之一變化型中,R1
、R2
、R3
及R4
各自獨立選自:-(C1
-C12
)-烷基、-(C4
-C14
)-芳基、環烷基、-(C1
-C12
)-雜烷基、-(C3
-C14
)-雜芳基、鹵素,且該等殘基也能形成較大縮合環; 其中該經列舉之烷基基團、芳基基團、環烷基、雜烷基基團、雜芳基基團可經下列取代: -(C1
-C12
)-烷基、-O-(C1
-C12
)-烷基、鹵素; 且該等基團R1
、R2
、R3
、R4
中之至少一者不表示苯基。 在該方法之一變化型中,R1
、R2
、R3
及R4
各自獨立選自:-(C1
-C12
)-烷基、環烷基、-(C3
-C14
)-雜芳基,且該等殘基也能形成較大縮合環; 其中該經列舉之烷基基團、環烷基、雜芳基基團可經下列取代: -(C1
-C12
)-烷基、-O-(C1
-C12
)-烷基、鹵素; 且該等基團R1
、R2
、R3
、R4
中之至少一者不表示苯基。 在該方法之一變化型中,R1
、R4
各自獨立選自: -(C1
-C12
)-烷基、環烷基,且該等殘基也能形成較大縮合環; 其中該經列舉之烷基基團、環烷基可經下列取代: -(C1
-C12
)-烷基、-O-(C1
-C12
)-烷基、鹵素。 在該方法之一變化型中,R2
、R3
各自獨立表示: -(C3
-C14
)-雜芳基, 其中該經列舉之雜芳基基團可經下列取代: -(C1
-C12
)-烷基、-O-(C1
-C12
)-烷基、鹵素。 在該方法之一變化型中,通式(I
)之化合物具有結構(II
):。
本發明將由以下示範性的具體實施例來詳細說明。 利用HCOOH之經Pd催化之四甲基乙烯1a
的甲氧羰基化反應:HCOOH之使用體積的影響添加[Pd(OAc)2
](1.12 mg, 0.25 mol%)、(II
)(8.72 mg, 1.0 mol%)、對-甲苯磺酸(PTSA·H2
O)(15.2 mg, 4 mol%)和經烘乾之攪拌棒至經密封之35 ml管內。將管與蓋子一同置於具有大開口之長Schlenk管。Schlenk管經抽空且再填充氬重覆三次。在氬氣環境下,使用注射器,將1a
(2 mmol)、MeOH (1.5 ml)和HCOOH (X ml)(X參見表1)注入35 ml管。然後用蓋子密封35 ml管。反應在100℃下進行超過13小時。在反應結束時,在無額外冷卻且小心洩壓下,令反應管到達室溫。然後,注射異辛烷(100 μl)作為內部標準。轉化率藉由GC分析測量。 結果摘述於以下表1。如上述實驗所顯示,藉由根據本發明之方法可解決本發明所針對的問題。
Claims (12)
- 一種使用甲酸和甲醇之甲氧羰基化的方法,其包含下列方法步驟:a)添加烯烴;b)添加包含Pd之化合物,其中該Pd能形成錯合物;c)添加通式(I)之化合物:
- 如請求項1之方法,其中HCOOH用作為該反應之唯一CO來源。
- 如請求項1之方法,其中在方法步驟b)中之該化合物係選自:Pd(acac)2、PdCl2、Pd(dba)3*CH3Cl(dba=二亞苄基丙酮)、Pd(OAc)2、Pd(TFA)2、Pd(CH3CN)Cl2。
- 如請求項1之方法,其中該方法包含額外的方法步驟g):g)添加酸。
- 如請求項4之方法,其中該酸係選自:H2SO4、CH3SO3H、CF3SO3H、PTSA。
- 如請求項1之方法,其中基於2mmol烯烴,HCOOH的使用體積是在0.4ml 至0.6ml之範圍中。
- 如請求項1之方法,其中R1、R2、R3、R4各自獨立選自:-(C1-C12)-烷基、-O-(C1-C12)-烷基、-(C4-C14)-芳基、-O-(C4-C14)-芳基、環烷基、-(C1-C12)-雜烷基、-O-(C1-C12)-雜烷基、-(C3-C14)-雜芳基、-O-(C3-C14)-雜芳基、-COO-烷基、-COO-芳基、-C-O-烷基、-C-O-芳基、NH2、鹵素,且該等殘基也能形成較大縮合環;其中該經列舉之烷基基團、芳基基團、環烷基、雜烷基基團、雜芳基基團可經下列取代:-(C1-C12)-烷基、-O-(C1-C12)-烷基、鹵素;且該等基團R1、R2、R3、R4中之至少一者不表示苯基。
- 如請求項1之方法,其中R1、R2、R3及R4各自獨立選自:-(C1-C12)-烷基、-(C4-C14)-芳基、環烷基、-(C1-C12)-雜烷基、-(C3-C14)-雜芳基、鹵素,且該等殘基也能形成較大縮合環;其中該經列舉之烷基基團、芳基基團、環烷基、雜烷基基團、雜芳基基團可經下列取代:-(C1-C12)-烷基、-O-(C1-C12)-烷基、鹵素;且該等基團R1、R2、R3、R4中之至少一者不表示苯基。
- 如請求項1之方法,其中R1、R2、R3及R4各自獨立選自:-(C1-C12)-烷基、環烷基、-(C3-C14)-雜芳基,且該等殘基也能形成較大縮合環;其中該經列舉之烷基基團、環烷基、雜芳基基團可經下列取代:-(C1-C12)-烷基、-O-(C1-C12)-烷基、鹵素;且該等基團R1、R2、R3、R4中之至少一者不表示苯基。
- 如請求項1之方法,其中R1、R4各自獨立選自:-(C1-C12)-烷基、環烷基,且該等殘基也能形成較大縮合環;其中該經列舉之烷基基團、環烷基可經下列取代:-(C1-C12)-烷基、-O-(C1-C12)-烷基、鹵素。
- 如請求項1之方法,其中R2、R3各自獨立表示:-(C3-C14)-雜芳基,其中該經列舉之雜芳基基團可經下列取代:-(C1-C12)-烷基、-O-(C1-C12)-烷基、鹵素。
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EP (1) | EP3441384B1 (zh) |
JP (1) | JP6823624B2 (zh) |
KR (1) | KR102147692B1 (zh) |
CN (1) | CN109384672A (zh) |
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TW201335134A (zh) * | 2011-12-19 | 2013-09-01 | Evonik Industries Ag | 由甲酸酯和烯系不飽和化合物製備酯類 |
TW201718093A (zh) * | 2015-07-23 | 2017-06-01 | 贏創德固賽有限責任公司 | 用於烷氧基羰基化的苯系雙膦配位子 |
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GB1176654A (en) | 1966-04-04 | 1970-01-07 | Ici Ltd | Decomposition of Formic Acid. |
US6706912B2 (en) * | 2000-03-14 | 2004-03-16 | Shell Oil Company | Process for the carbonylation of ethylenically unsaturated compounds |
TWI301481B (en) * | 2002-08-10 | 2008-10-01 | Lucite Int Uk Ltd | A catalyst system |
JP2010511600A (ja) * | 2006-12-02 | 2010-04-15 | ルーサイト インターナショナル ユーケー リミテッド | 新規のカルボニル化配位子及びエチレン性不飽和化合物のカルボニル化におけるその使用 |
GB0812297D0 (en) * | 2008-07-04 | 2008-08-13 | Lucite Int Uk Ltd | Novel carbonylation ligand sand thier use of in the carbonylation of ethylenically unsaturated compounds |
GB201000078D0 (en) * | 2010-01-05 | 2010-02-17 | Lucite Int Uk Ltd | Process for the carbonylation of ethylenically unsaturated compounds, novel carbonylation ligands and catalyst systems incorporatng such ligands |
DE102011007661A1 (de) | 2011-04-19 | 2012-10-25 | Leibniz-Institut Für Katalyse E.V. An Der Universität Rostock | Verfahren zur Wasserstoffgewinnung durch katalytische Zersetzung von Ameisensäure |
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---|---|---|---|---|
TW201335134A (zh) * | 2011-12-19 | 2013-09-01 | Evonik Industries Ag | 由甲酸酯和烯系不飽和化合物製備酯類 |
TW201718093A (zh) * | 2015-07-23 | 2017-06-01 | 贏創德固賽有限責任公司 | 用於烷氧基羰基化的苯系雙膦配位子 |
Non-Patent Citations (2)
Title |
---|
Tsumoru Morimoto et al, "Catalytic Carbonylation Methods without the Direct Use of Carbon Monoxide", 有機合成化学協会誌, Vol.63, No.9, 2004, page 861-871 * |
Tsumoru Morimoto et al, "Catalytic Carbonylation Methods without the Direct Use of Carbon Monoxide", 有機合成化学協会誌, Vol.63, No.9, 2004, page 861-871。 |
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TW201910304A (zh) | 2019-03-16 |
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