Method of producing methyl propyanate

专利摘要:
Process for the carbonylation of an olefinically unsaturated compound with CO in the presence of water, an alcohol and/or a carboxylic acid and in the presence of a homogeneous catalytic system prepared by combining:- a) a Pd(II) compound, b) at least 5 mol of a triarylphosphine per gram atom Pd, and c) at least 1 mol of a non-carboxylic acid having a pKa > 2 and/or of a sterically hindered carboxylic acid having a pKa < 4.5 per mol phosphine. o
公开号:SU1597095A3
申请号:SU874202046
申请日:1987-02-26
公开日:1990-09-30
发明作者:Дрент Эйт
申请人:Шелл Интернэшнл Рисерч Маатсхаппий Б.В. (Фирма)；
IPC主号:

专利说明:

The invention relates to an improved process for the preparation of methyl propionate, which is used as an intermediate in organic synthesis.
The aim of the invention is to increase the rate of accumulation of the target product.
Example “In a 300 ml autoclave with a magnetic stirrer, 50 ml of methanol, 0.1 mmol of palladium (II) acetate, 3 mmol of triphenylphosphine and 10 mmol of orthophosphoric acid are placed. B the autoclave admits a stream of carbon monoxide, add ethylene until a pressure of 20 atm is established, then carbon monoxide is again added at a partial pressure of 30 atm.
tiziruyte the autoclave and heated to 120 ° C. The contents of the autoclave are analyzed by gas-liquid chromatography; the reaction rate is 700 g of methyl propionate per 1 g of Pd: h,
Example 2 The experiment was carried out analogously to Example 1, loading 50 m. 1 methanol into the autoclave, 10 mmol of 2.6 dichlorobenzoic acid, 0.1 mmol of palladium (II) acetate, add ethylene to 20 atm, 2 mmol of tri-c-methoxyphenyl) osfin, then carbon monoxide to 30 atm.
The reaction rate is 1000 g of methyl propionate per 1 g of Pd h,

权利要求:
Claims (1)
[1]
Example .3. The experiment was carried out analogously to example 1, loading into the autoclave 50 ml of methanol, 10 mmol of benzenephosphonic acid, 0.1 mmol of palladium (II) acetate, add ethylene to 20 atm, 2 mmol of triphenyl phosphine, carbon monoxide to 30 atm. The reaction rate is 800 g of methyl propionate per 1 g of Pd4. Example 4c The experiment was carried out analogously to example 2, but 2,6-dichlorobenzoic acid was replaced with 10 mmol 2, A, b-trimethylbenzoic acid (pK4, below 4, .5). The reaction rate is 400 g of methyl propionate per 1 g of Pd-M, Example 5 (prototype). The experiment was carried out analogously to the example of but 2,6-dichlorobenzoic acid; 10 mmol of pivalic acid (pK = 5.0) was replaced. The reaction rate is less than 5 g of methyl propionate 1 g of Pd4. Example of a bvB 300 ml autoclave with a magnetic stirrer 50 ml of methanol are placed, 0.1 mmol of palladium adduct (11). A stream of carbon monoxide is started in the autoclave, ethylene is added to setting the pressure to 20 atm, then carbon monoxide is added again to a partial pressure of 30 atm, the autoclave is sealed and heated to 75 ° C. The contents of the autoclave are analyzed by liquid chromatography; reaction rate was 32 g of methyl propionate per 1 g of Pd. Example 7 “, In a 300 ml autoclave with a magnetic stirrer, 50 ml of methanol, 0.1 mmol 1 4 palladium (II) acetate, 3 mmol triphenylphosphine and 10 mmol orthophosphoric acid. A stream of carbon monoxide is introduced into the autoclave, ethylene is added to establish a pressure of 20 atm, then carbon monoxide is added again to a partial pressure of 30 atm, the autoclave is sealed and heated until the contents of the autoclave are analyzed using gas chromatography; The reaction rate is 550 g of methyl propionate per I g of Pd h. Thus, this method allows you to increase the rate of accumulation of the target product from 5 g of the prototype to 400-1000 g per 1 g of Pdr4. Claims of the method for producing methyl propionate by carbonylation of ethylene carbon monoxide in the presence of water, alcohol, acid, palladium acetate and phosphine selected from the group of triphenylphosphine or tri (methoxyphenyl) phosphine, with a molar ratio of palladium acetate: phosphine equal to 0.1: (2-3) at a temperature of 75 -150 C and a pressure of 20-80 atm, characterized in that then, in order to increase the rate of accumulation of the target product, o-phosphoric acid or 2,6-dichlorobenzoic acid, or benzene phosphonic acid, or 2,4,6-trimethylbenzoic acid at a molar ratio of 1 acid and phosphine 10: (: ( 2-3)

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引用文献:

---

公开号 | 申请日 | 公开日 | 申请人 | 专利标题

---

RU2482916C2|2007-03-26|2013-05-27|Хераеус Прешес Металс ГмбХ энд Ко.КГ|CARBOXYLATE COMPOUNDS OF NOBLE METALS Ir, Ru, Rh, Pd, Pt AND Au, HAVING HIGH CATALYTIC EFFICIENCY|GB1051627A|1961-12-29|

---

DE1249867B|1964-12-19|1967-09-14|Badische Anilin- &. Soda-Fabnk Aktiengesellschaft, Ludwigshaf en/Rhem|Process for the production of carboxylic acids or carboxylic acid esters|

---

EP0055875B1|1981-01-06|1986-08-20|Shell Internationale Researchmaatschappij B.V.|Process for the carbonylation of olefins|

---

JPS5910545A|1982-07-08|1984-01-20|Mitsubishi Petrochem Co Ltd|Preparation of carboxylic acid or ester thereof|

---

CA1231346A|1982-09-30|1988-01-12|Eit Drent|Process for the carbonylation of olefinicallyunsaturated compounds with a palladium catalyst|

---

GB8432376D0|1984-12-21|1985-02-06|Shell Int Research|Carbonylation of acetylenically unsaturated compounds|

---

GB8501919D0|1985-01-25|1985-02-27|Shell Int Research|Carbonylation of allenically unsaturated compounds|

---

GB8509641D0|1985-04-15|1985-05-22|Shell Int Research|Carboxylic di-esters/acids|GB8712455D0|1987-05-27|1987-07-01|Shell Int Research|Preparation of cyclic carboxylic anhydrides|

---

GB8729267D0|1987-12-15|1988-01-27|Shell Int Research|Process for production of propionate esters|

---

GB2226822A|1988-12-29|1990-07-11|Shell Int Research|Process for the carbonylation polymerization of functionalized olefinically unsaturated compounds|

---

GB8917579D0|1989-08-01|1989-09-13|Shell Int Research|Preparation of alkyl propionates|

---

GB9002521D0|1990-02-05|1990-04-04|Shell Int Research|Carbonylation catalyst system|

---

US5166411A|1990-02-05|1992-11-24|Shell Oil Company|Carbonylation catalyst system|

---

US5304674A|1992-06-29|1994-04-19|Shell Oil Company|Preparation of alkanedioic derivatives|

---

TW272949B|1994-07-22|1996-03-21|Taishal Kagaku Kogyo Kk|

---

US5495041A|1995-02-22|1996-02-27|Dsm N.W.|Process for the preparation of a pentenoate ester|

---

GB0218613D0|2002-08-10|2002-09-18|Lucite Int Uk Ltd|Process for the carbonylation of ethylenically unsaturated compounds|

---

TWI301481B|2002-08-10|2008-10-01|Lucite Int Uk Ltd|A catalyst system|

---

WO2005003070A1|2003-07-03|2005-01-13|Lucite International Uk Limited|Process for the hydroformylation of ethylenically unsaturated compounds|

---

GB0403592D0|2004-02-18|2004-03-24|Lucite Int Uk Ltd|A catalyst system|

---

GB0411951D0|2004-05-28|2004-06-30|Lucite Int Uk Ltd|Carbonylation of ester|

---

GB0516556D0|2005-08-12|2005-09-21|Lucite Int Uk Ltd|Improved catalyst system|

---

JP2009515936A|2005-11-17|2009-04-16|ルーサイトインターナショナルユーケーリミテッド|Carbonylation of ethylenically unsaturated compounds.|

---

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---

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---

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---

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法律状态:

优先权:

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申请号 | 申请日 | 专利标题

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GB868605034A|GB8605034D0|1986-02-28|1986-02-28|Carbonylation of compounds|

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