WO2003078370A1 - Procede de production des composes carbonyles - Google Patents

Procede de production des composes carbonyles Download PDF

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Publication number
WO2003078370A1
WO2003078370A1 PCT/RU2002/000491 RU0200491W WO03078370A1 WO 2003078370 A1 WO2003078370 A1 WO 2003078370A1 RU 0200491 W RU0200491 W RU 0200491W WO 03078370 A1 WO03078370 A1 WO 03078370A1
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WO
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Prior art keywords
reaction
goodbye
inert gas
atm
nitrous oxide
Prior art date
Application number
PCT/RU2002/000491
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English (en)
Russian (ru)
Inventor
Evgeny Vladimirovich Starokon
Gennady Ivanovich Panov
Constantin Alexandrovich Dubkov
Valentin Nikolaevich Parmon
Original Assignee
Institut Kataliza Imeni G.K. Boreskova Sibirskogo Otdeleniya Rossiiskoi Akademii Nauk
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by Institut Kataliza Imeni G.K. Boreskova Sibirskogo Otdeleniya Rossiiskoi Akademii Nauk filed Critical Institut Kataliza Imeni G.K. Boreskova Sibirskogo Otdeleniya Rossiiskoi Akademii Nauk
Priority to AU2002349594A priority Critical patent/AU2002349594A1/en
Publication of WO2003078370A1 publication Critical patent/WO2003078370A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties

Definitions

  • a removable patent expands the means of aldehyde and ketone production by oxidizing aliphatic alkenes, which does not have 5 indicated deficiencies.
  • composition of oxidizable alcohols may be expressed by formula (I)
  • the safe working conditions are offered by the method of ensuring the inert mixture of inert gas is not
  • Non-inert gas can play the flue gases of the reaction.
  • ⁇ 2 for example, nitrogen, argon, helium, carbon dioxide, etc., or any mixture.
  • Non-inert gas can play the flue gases of the reaction.
  • combustion inhibitors can be added, such as transformer, dimer, and dimer.
  • an alkyne is added to the autoclave (with or without a solvent) in such a way that the process is heated up. Then, nitrous oxide or its mixture with inert gas is supplied,
  • Nitrous nitrous oxide can be used in such a way that its pressure at the reaction temperature is 0.01-100 atm. After this reaction, the reaction is heated to a temperature of 20-350 ° ⁇ . The response time is subject to the conditions of its use, and, accordingly,
  • the proposed process is free of solvents. At the same time, with the introduction of the process and with the use of a device, it may be possible to get out of a wide range of substances,
  • EXAMPLE 1 A volume of 100 cm 3 , made from solid steel and equipped with a ⁇ : enamel mixer (Form Mag), is filled with 25 cm 2-Penten ( ⁇ ⁇ ⁇ ⁇ , 99%). They blow off nitrous oxide and then bring its pressure to 10 atm. They pressurize, heat up to 197 ° ⁇ and stand at this temperature for 12 hours. After
  • ⁇ ⁇ 1 are inverted 2-penten at different conditions of reaction, and the total selective selectivity at 2- and 3-pentents, which are in all cases experienced, is not experienced at all.
  • 10 EXAMPLE 2 is similar to Example 1 with the exception that the reaction is carried out for 5 hours, using in the quality of the transmitter. To do this, before starting the experiment, pour 10 ml of 2-Pentene and 70 ml of Toluene into the reaction.
  • Example 3 is similar to Example 2, except that, in the quality range 15 of the device, it is mesitic. For this, before starting the experiment, 15 ml of 2-pentene and 60 ml of mesitylene are poured into the reaction. The reaction is carried out at 190 ° ⁇ for 15 hours.
  • Example 4 is similar to Example 3, which is similar to that used by the consumer as a cyclohexane.
  • Example 5 is similar to Example 4, except that the reaction takes 7 hours in the case of 0.2 g of Ge 2 0Z / 8U 2 (2.8 wt.%> Ge 2 0 3 ). It is prepared by cooking with 8 ⁇ 0 2 and disposing of CeC1 3 , it is dried at 110 ° ⁇ and is heated at the temperature of 500 ° ⁇ for 2 hours.
  • Example 6 is similar to Example 5 with the same reaction that 25 is carried out at 197 ° C in the presence of 0.3 g of ⁇ / ⁇ 2 (1 wt.% ⁇ ). It is prepared by the preparation of ZU 2, which is prepared for 3 , dries at 110 ° ⁇ and is heated at the temperature of 500 ° ⁇ for 2 hours.
  • Example 7 is similar to Example 4, which is different from the fact that, as a part of the distributor, it is used.
  • Example 8 is similar to Example 4, except that the manufacturer uses it as a part of the device. Table 1
  • Example 10 describes the oxidation of propylene with the use of a mesitylene reagent.
  • Example 15 pour 50 ml of mesitylene into the temperature and feed it to a pressure of 7 atm. Then, ⁇ 2 0 is supplied, so that the total pressure of 15 atm is established in the process. Further, an experiment is carried out in a similar manner to Example 1.
  • the reaction products are acetic acid, acetaldehyde and acetaldehyde in the range of
  • Example 11 describes the oxidation of 1-hexene.
  • the experiment is carried out similarly to Example 1 with the exception that, in the original source, the alkene takes 1-hexen and the initial pressure of ⁇ 2 0 is set to 25 atm.
  • the conversion of 1-hexene is 10.5%, 5 by the following acids, the concentration of 1-hexane is 1 (35%) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1)
  • EXAMPLE 12 Describes the oxidation of 1 octene.
  • the experiment is carried out in a similar manner to Example 11 with the exception that, in addition to 1-hexene, 1-octene is used and the reaction is carried out at 220 ° C. 10
  • the result of the reaction is 10% 1% conversion is 47%), due to the following acid treatment: 2% (1%)% (1%).
  • EXAMPLE 13 Describes the oxidation of a building. ⁇ Reactor and room temperature pour 5 ml of styrene and 45 ml of cyclohexane. 15 Then feed ⁇ 2 0 to a pressure of 10 atm. Experiment at 250 ° C for 3 hours. In the case of acid-containing products, benzaldehyde, acetic acid and phenylacetaldehyde are produced in an approximate small 5: 2: 1 ratio.
  • Example 14 is similar to Example 13, which, in contrast to 20, inhibits the use of polymerization in a reactive mixture, adds 0.2 g of hydrogen and gives a reaction time of 200 ° C.
  • benzaldehyde, acetone and phenylacetaldehyde are used in an approximate small ratio of 7.5-20: 1.
  • Examples 15–20 ⁇ are given in table. 2. These examples show the possibility of selective oxidation of 2-pentene in 2- and 3-pentanes using diluted mixtures of nitrous oxide.
  • ⁇ ⁇ 2 summarized selectivities for potentials are presented.
  • Example 18 is similar to Example 17 with an exception that the concentration of nitrous oxide in the mixture is 25%, and the initial pressure of the mixture is 15 at 130 atm. Experienced within 10 hours.
  • Example 19 is similar to Example 18 with the exception that, in the case of inert gas, instead of nitrogen, use an argon, in addition to an overpressure of a mixture of 50%. Experienced within 15 hours. 20
  • Example 20 is similar to Example 19 with the exception that, instead of the argon, carbon dioxide is used. Table 2
  • Example 21 is similar to example 11 for the oxidation of 1-hexene with the exception that, in addition to a pure nitrous oxide, it uses a mixture with inert gas - nitrogen, at a temperature of 0%. ⁇ As a result of the reaction, the conversion of 1-hexen is 11>. The following acidic compounds were found in reaction products: 2-hexane (32%), 1-hexane (30%), 1-Pentanal (32%).
  • Example 22 is similar to Example 21, which is, in place of 1-
  • Compound ⁇ 2 0 in inert gas may vary in wide range, including the percentage of consumption of 25% or less, which is excluded.

Abstract

L'invention se rapporte à un procédé de production des composés carbonylés avec un numéro atomique de C2-C40. Le procédé selon l'invention est basé sur la réaction d'oxydation en phase liquide des alcènes aliphatiques C2-C40 en composés carbonylés à l'aide de l'oxyde d'azote ou de son mélange avec un gaz inerte. L'oxydation est effectuée à une température de 20-350 °C et une pression de l'oxyde d'azote de 0,01-100 atm. Le procédé assure une haute sélectivité aux produits cibles, la sécurité contre le risque d'explosion et se révèle prometteur à des fins industrielles.
PCT/RU2002/000491 2002-03-20 2002-11-06 Procede de production des composes carbonyles WO2003078370A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002349594A AU2002349594A1 (en) 2002-03-20 2002-11-06 Method for producing carbonyl compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
RU2002106989 2002-03-20
RU2002106989/04A RU2227133C2 (ru) 2002-03-20 2002-03-20 Способ получения карбонильных соединений

Publications (1)

Publication Number Publication Date
WO2003078370A1 true WO2003078370A1 (fr) 2003-09-25

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/RU2002/000491 WO2003078370A1 (fr) 2002-03-20 2002-11-06 Procede de production des composes carbonyles

Country Status (3)

Country Link
AU (1) AU2002349594A1 (fr)
RU (1) RU2227133C2 (fr)
WO (1) WO2003078370A1 (fr)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1627890A1 (fr) * 2003-05-23 2006-02-22 Institut Kataliza Imeni G.K. Boreskova, Sibirskogo Otdeleniya Rossiiskoi Akademii Nauk Procede d'introduction de groupes carbonyles dans des polymeres contenant des liaisons doubles carbone-carbone
US7649119B2 (en) 2006-06-29 2010-01-19 Basf Se Method for the production of cyclic ketones
US7692045B2 (en) 2004-09-23 2010-04-06 Basf Aktiengesellschaft Method for purifying and concentrating dinitrogen monoxide
US7714172B2 (en) 2006-06-29 2010-05-11 Basf Se Method for the production of cyclic ketones
WO2010076182A1 (fr) 2008-12-30 2010-07-08 Basf Se Procédé de production de cétones par réaction d'oléfines 1,1-disubstituées avec du n2o
US7754172B2 (en) 2005-11-22 2010-07-13 Basf Aktiengesellschaft Method for isolating N2O
US7803971B2 (en) 2004-09-23 2010-09-28 Basf Akiengesellschaft Method for the production of cyclopentanone
WO2012066296A2 (fr) 2010-11-19 2012-05-24 Invista Technologies S.A.R. L. Oxyde de diazote-contenant des liquides ioniques en tant que réactifs chimiques
CN102498145A (zh) * 2009-07-10 2012-06-13 巴斯夫欧洲公司 基于可再生资源生产多元醇的方法
US8404901B2 (en) 2008-04-02 2013-03-26 Basf Se Process for purifying dinitrogen monoxide
US8449655B2 (en) 2006-12-11 2013-05-28 Basf Aktiengesellschaft Process for isolating N2O
US8461392B2 (en) 2008-08-29 2013-06-11 Basf Se Process for preparing cyclic ketones
US8808430B2 (en) 2008-04-02 2014-08-19 Basf Se Process for purifying N2O
WO2014165424A1 (fr) 2013-04-03 2014-10-09 Shell Oil Company Procédé de préparation d'alcools en c10 à c30
WO2016114687A1 (fr) * 2015-01-12 2016-07-21 Акционерное Общество "Газпромнефть - Московский Нпз" (Ао "Газпромнефть - Мнпз") Procédé de production de composés de carbonyle с2-с4
CN108698960A (zh) * 2015-12-09 2018-10-23 股份有限公司“天然气工业石油-莫斯科炼油厂”（或“天然气工业石油-Mnpz”） 由来自催化裂化的烯烃生产高辛烷值组分的方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007055608A2 (fr) * 2005-11-08 2007-05-18 Institut Problem Khimicheskoi Fiziki Rossiiskoi Akademii Nauk Procede de fabrication de methylethylcetone

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB649680A (en) * 1948-09-22 1951-01-31 Gerard Dunstan Buckley Manufacture of oxidation products from olefinic compounds
SU504749A1 (ru) * 1974-04-19 1976-02-28 Казанский Химико-Технологический Институт Им.С.М.Кирова Способ получени 1,4-дизамещенных бутандионов-2,3

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB649680A (en) * 1948-09-22 1951-01-31 Gerard Dunstan Buckley Manufacture of oxidation products from olefinic compounds
SU504749A1 (ru) * 1974-04-19 1976-02-28 Казанский Химико-Технологический Институт Им.С.М.Кирова Способ получени 1,4-дизамещенных бутандионов-2,3

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BRIDSON-JONES ET AL.: "Oxidation of organic compounds by nitrous oxide", J. CHEM. SOC., November 1951 (1951-11-01), pages 2999 - 3333, 3003-3005, 3007-3015 *

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1627890A4 (fr) * 2003-05-23 2007-01-31 Boreskova Inst Kataliza Sibir Procede d'introduction de groupes carbonyles dans des polymeres contenant des liaisons doubles carbone-carbone
EP1627890A1 (fr) * 2003-05-23 2006-02-22 Institut Kataliza Imeni G.K. Boreskova, Sibirskogo Otdeleniya Rossiiskoi Akademii Nauk Procede d'introduction de groupes carbonyles dans des polymeres contenant des liaisons doubles carbone-carbone
US7803971B2 (en) 2004-09-23 2010-09-28 Basf Akiengesellschaft Method for the production of cyclopentanone
US7692045B2 (en) 2004-09-23 2010-04-06 Basf Aktiengesellschaft Method for purifying and concentrating dinitrogen monoxide
US7754172B2 (en) 2005-11-22 2010-07-13 Basf Aktiengesellschaft Method for isolating N2O
US7649119B2 (en) 2006-06-29 2010-01-19 Basf Se Method for the production of cyclic ketones
US7714172B2 (en) 2006-06-29 2010-05-11 Basf Se Method for the production of cyclic ketones
US8449655B2 (en) 2006-12-11 2013-05-28 Basf Aktiengesellschaft Process for isolating N2O
US8404901B2 (en) 2008-04-02 2013-03-26 Basf Se Process for purifying dinitrogen monoxide
US8808430B2 (en) 2008-04-02 2014-08-19 Basf Se Process for purifying N2O
US8461392B2 (en) 2008-08-29 2013-06-11 Basf Se Process for preparing cyclic ketones
US8420866B2 (en) 2008-12-30 2013-04-16 Basf Se Process for preparing ketones by reacting 1,1-disubstituted olefins with N2O
WO2010076182A1 (fr) 2008-12-30 2010-07-08 Basf Se Procédé de production de cétones par réaction d'oléfines 1,1-disubstituées avec du n2o
CN102498145A (zh) * 2009-07-10 2012-06-13 巴斯夫欧洲公司 基于可再生资源生产多元醇的方法
CN102498145B (zh) * 2009-07-10 2013-10-23 巴斯夫欧洲公司 基于可再生资源生产多元醇的方法
WO2012066296A2 (fr) 2010-11-19 2012-05-24 Invista Technologies S.A.R. L. Oxyde de diazote-contenant des liquides ioniques en tant que réactifs chimiques
WO2014165424A1 (fr) 2013-04-03 2014-10-09 Shell Oil Company Procédé de préparation d'alcools en c10 à c30
WO2016114687A1 (fr) * 2015-01-12 2016-07-21 Акционерное Общество "Газпромнефть - Московский Нпз" (Ао "Газпромнефть - Мнпз") Procédé de production de composés de carbonyle с2-с4
CN107108412A (zh) * 2015-01-12 2017-08-29 股份有限公司"天然气工业石油-莫斯科炼油厂"（或"天然气工业石油-Mnpz"） 生产c2‑c4羰基化合物的方法
US9975836B2 (en) 2015-01-12 2018-05-22 Aktsionernoe Obschestvo Gazpromneft—Moskovsky Npz (Ao “Gazpromneft-Mnpz”) Method of producing C2-C4 carbonyl compounds
CN107108412B (zh) * 2015-01-12 2019-03-29 股份有限公司"天然气工业石油-莫斯科炼油厂"（或"天然气工业石油-Mnpz"） 生产c2-c4羰基化合物的方法
CN108698960A (zh) * 2015-12-09 2018-10-23 股份有限公司“天然气工业石油-莫斯科炼油厂”（或“天然气工业石油-Mnpz”） 由来自催化裂化的烯烃生产高辛烷值组分的方法
EP3388410A4 (fr) * 2015-12-09 2019-01-02 Aktsionernoe Obschestvo "Gazpromneft Moskovsky NPZ" (AO "Gazpromneft - MNPZ") Procédé de production de composants à indice d'octane élevé à partir d'oléfines provenant du craquage catalytique
US10336670B2 (en) 2015-12-09 2019-07-02 Aktsionernoe Obschestvo “Gazpromneft—Moskovsky NPZ” (AO Gazpromneft-MNPZ) Method for producing high-octane components from olefins from catalytic cracking

Also Published As

Publication number Publication date
AU2002349594A1 (en) 2003-09-29
RU2227133C2 (ru) 2004-04-20

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