WO2003078371A1 - Procede de production des cetones monocycliques substitues - Google Patents

Procede de production des cetones monocycliques substitues Download PDF

Info

Publication number
WO2003078371A1
WO2003078371A1 PCT/RU2002/000494 RU0200494W WO03078371A1 WO 2003078371 A1 WO2003078371 A1 WO 2003078371A1 RU 0200494 W RU0200494 W RU 0200494W WO 03078371 A1 WO03078371 A1 WO 03078371A1
Authority
WO
WIPO (PCT)
Prior art keywords
reaction
nitrous oxide
case
atm
inert gas
Prior art date
Application number
PCT/RU2002/000494
Other languages
English (en)
Russian (ru)
Inventor
Constantin Alexandrovich Dubkov
Evgeny Vladimirovich Starokon
Gennady Ivanovich Panov
Dmitry Petrovich Ivanov
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.)
Filing date
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 AU2002349603A priority Critical patent/AU2002349603A1/en
Publication of WO2003078371A1 publication Critical patent/WO2003078371A1/fr

Links

Classifications

    • 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

  • Substituted cyclic ketones C 4 -C 20 are the source materials for the synthesis of various organic products, including synthetic ones,
  • a mixture of alkyl substituted cyclic ketones and systems can also be obtained from the use of cyclic pressure regulators at a temperature of -120 ° C.
  • Alkyl substituted mono-cyclic ketones can also be obtained by deactivating and cycling alkyl substituted dicarboxylic acids [Sh. 5600013, C07C 45/48, 1997]. The process conducts at 200-300 ° C, using as a means of catalytic analysis of metals 1a, 2a or 3Z group of the chemical system of elements.
  • a serious serious disadvantage of this method is that it is possible to develop flammable mixtures, to avoid the use of explosives, it is a self
  • a dormant patent expands the methods of receiving substituted mnets through the oxidation of substituted mnets Alkaline in the presence of nitrogen, ⁇ , which does not have the indicated disadvantages.
  • the reaction is carried out under milder conditions, when the system is in the form of a liquid phase in the vehicle An excessive 5 increase in the temperature and / or pressure of the gas is undesirable, since it may be necessary to reduce the selectivity due to the contribution of the gas-oxidation.
  • composition of the original substituted cyclic alcohols is expressed in the form of ⁇ n (2 ⁇ . 2. T) ⁇ ; protest( ⁇ ), where ⁇ 'is the same or different substituents with a value of 2, (2 ⁇ -2).
  • Substituents ⁇ 'in formula (I) may be provided by halogen atoms, alkylene, alkenyl, aryl or any other non-organic, organic or metallic
  • radicals including those containing different functional groups, except for radicals, which also include non-automatic, non-automatic, and non-automatic communications.
  • radicals which also include non-automatic, non-automatic, and non-automatic communications.
  • inert gas can play the flue gases of the reaction.
  • gas for example, nitrogen, helium, argon, carbon dioxide, etc., or any mixture.
  • Non-inert gas can play the flue gases of the reaction.
  • cyclic: nitrous oxide for inert gas necessary for
  • the process closes and heats up the temperature of the temperature ⁇ eb ⁇ vany same, ⁇ edyavlyaemy ⁇ ⁇ ⁇ tsessu and m ⁇ zhe ⁇ izmenya ⁇ sya ⁇ nes ⁇ l ⁇ i ⁇ desya ⁇ v 20 minutes the d ⁇ nes ⁇ l ⁇ i ⁇ desya ⁇ v chas ⁇ v
  • the 25 basic products of the reaction are 3-methylcyclohexan and 4-methylcycane.
  • ⁇ ⁇ 1 indicates the total selectivity for 3- and 4-steel microhexans, which are generally used in equal quantities.
  • EXAMPLE 2 is similar to Example 1 with the exception that experience occurs within 12 hours.
  • Example 3 is similar to Example 1 with the exception that it is more than 150 ° C for 20 hours.
  • Example 4 is similar to Example 1 with the exception that it is experience of 198 ° C for 15 hours.
  • EXAMPLE 5 is similar to Example 1 with the exception that experience of 220 ° C for 12 hours.
  • Example 6 is similar to Example 1 with the exception that experience is achieved at 300 ° C for 3 hours. Table 1
  • Example 8 is analogous to Example 4, with the exception that the long-standing initial nitrous oxide recordings in this experiment are set to 40 atoms and experience lasting 25 hours.
  • Example 9 is similar to Example 5 with the exception that the initial pressure of nitrous oxide in this experiment is set to 10 atm Table 2
  • Example 10 is analogous to Example 4 with the exception that the oxidation of 4-methyl-1-cyclohexene leads to the presence of 0 5 g Less 2 % / v ⁇ 2 (2 8% by weight 2 %)
  • Example 12 20 cycles, including the use of consumables in the form of acid-containing products in the process Example 12 is similar to Example 1, which means that they fill 25 cm 3 with 1 methyl-1-cyclohexene (99%) and have a maximum of 250 ° C.
  • Example 14 is similar to Example 13, which, in turn, uses the transmitter and the amplifier for 220 seconds for 5-10 hours, which means that it takes about a couple of minutes.
  • Example 16 is analogous to Example 4 with the exception of 4-methyl
  • Examples 17-22 show the possibility of reacting with 25 diluted nitrous oxide mixtures (Table 4).
  • Example 19 is similar to Example 18 with the exception that the initial pressure in the process is set to 90 atm. It is experienced at 220 ° C for 12 hours
  • Example 20 is similar to Example 19 with a difference that a concentration of ⁇ 2 0 in the mixture is 40%; the initial pressure in the process is 40 atm.
  • EXAMPLE 22 is similar to Example 21, in other words, instead of using carbon dioxide.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention se rapporte à un procédé de production des cétones monocycliques substitués C4-C20.. Le procédé selon l'invention est basé sur la réaction d'oxydation en phase liquide des cétones monocycliques substitués C4-C20 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/RU2002/000494 2002-03-20 2002-11-06 Procede de production des cetones monocycliques substitues WO2003078371A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002349603A AU2002349603A1 (en) 2002-03-20 2002-11-06 Method for producing substituted monocyclic ketones

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
RU2002106988 2002-03-20
RU2002106988/04A RU2227134C2 (ru) 2002-03-20 2002-03-20 Способ получения замещенных моноциклических кетонов

Publications (1)

Publication Number Publication Date
WO2003078371A1 true WO2003078371A1 (fr) 2003-09-25

Family

ID=28036515

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/RU2002/000494 WO2003078371A1 (fr) 2002-03-20 2002-11-06 Procede de production des cetones monocycliques substitues

Country Status (3)

Country Link
AU (1) AU2002349603A1 (fr)
RU (1) RU2227134C2 (fr)
WO (1) WO2003078371A1 (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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

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, 3001, 3004, 3009-3011, 3015 *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7692045B2 (en) 2004-09-23 2010-04-06 Basf Aktiengesellschaft Method for purifying and concentrating dinitrogen monoxide
US7803971B2 (en) 2004-09-23 2010-09-28 Basf Akiengesellschaft Method for the production of cyclopentanone
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
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
US8420866B2 (en) 2008-12-30 2013-04-16 Basf Se Process for preparing ketones by reacting 1,1-disubstituted olefins with N2O
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

Also Published As

Publication number Publication date
RU2227134C2 (ru) 2004-04-20
AU2002349603A1 (en) 2003-09-29

Similar Documents

Publication Publication Date Title
Wang et al. Selective cyclohexane oxidation catalyzed by manganese porphyrins and co-catalysts
WO2003078371A1 (fr) Procede de production des cetones monocycliques substitues
US20090306425A1 (en) Production of Carboxylic Acids
WO2003078375A1 (fr) Procede de production des cetones monocycliques c7-c20
WO2005092827A1 (fr) Processus de production d’un composé acide dicarboxylique aliphatique
US3059028A (en)
CN111848371A (zh) 一种臭氧氧化芳烃制备芳香酮的方法
US3944620A (en) Process for the preparation of oxophorones
CN113620790B (zh) 一种β-IP氧化制备4-氧代异佛尔酮的方法
US4877903A (en) Cyclohexanol/cyclohexanone mixtures produced from cyclohexane
US3251876A (en) Process for air-oxidation of beta-acyloxyaldehydes to beta-acyloxy-carboxylic acids
US3231620A (en) Production of carbonyl compounds
Kamath et al. Liquid phase oxidation of cyclohexanone to adipic acid by air in acetic acid solution
US3366680A (en) Process for preparing dodecandioic acid from cyclododecane
SU172296A1 (fr)
CN111548333A (zh) 一种制备δ-戊内酯的新方法
Kuramshin et al. Oxidation of cyclic acetals as a preparative method of diol monoester production
US3125600A (en) figures i
DiCosimo et al. Cobalt (III)-catalyzed trifluoroacetoxylation of benzene
US3042722A (en) Oxidation of cyclic olefins
KR910002280B1 (ko) 아디프산의 제조방법
US6307100B1 (en) Catalytic oxidation of hydrocarbons
US6258981B1 (en) Catalytic oxidation of hydrocarbons
CN113651761A (zh) 一种联苯吡嗪菌胺前体的合成方法
EP1279657B1 (fr) Procédé pour la préparation de composés carbonyliques à partir d'alcools

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AT AU BG BR CA CN CO CU CZ DE DK DZ EE ES FI GB GE HR HU ID IL IN IS JP KP KR KZ LT LV MK MN MX NO NZ PL PT RO SD SE SG SI SK TR UA US UZ VN YU ZA

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR IE IT LU MC NL PT SE SK TR

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP

WWW Wipo information: withdrawn in national office

Country of ref document: JP