WO2002014302A1 - Procede de production d'un compose de carbonate d'alkylene - Google Patents

Procede de production d'un compose de carbonate d'alkylene Download PDF

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Publication number
WO2002014302A1
WO2002014302A1 PCT/JP2000/008358 JP0008358W WO0214302A1 WO 2002014302 A1 WO2002014302 A1 WO 2002014302A1 JP 0008358 W JP0008358 W JP 0008358W WO 0214302 A1 WO0214302 A1 WO 0214302A1
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WO
WIPO (PCT)
Prior art keywords
carbonate
alkylene
oxide
group
reaction
Prior art date
Application number
PCT/JP2000/008358
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English (en)
Japanese (ja)
Inventor
Yutaka Ikushima
Hajime Kawanami
Kazuo Torii
Original Assignee
National Institute Of Advanced Industrial Science And Technology
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 National Institute Of Advanced Industrial Science And Technology filed Critical National Institute Of Advanced Industrial Science And Technology
Publication of WO2002014302A1 publication Critical patent/WO2002014302A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Definitions

  • the present invention is directed to an alkyleneoxy group in the presence of a polar organic solvent having an amide group or a sulfonyl group under supercritical carbon dioxide or subcritical carbon dioxide conditions without using a homogeneous or heterogeneous metal catalyst. And a method for efficiently synthesizing carbonate.
  • a method for producing an alkylene carbonate using a carboxylic acid type cation exchange resin having an alkyl group-substituted ammonium cation as a counter cation as a catalyst Japanese Patent Application Laid-Open No. 7-246846
  • a tungsten oxide Or a method for producing an alkylene carbonate using a catalyst comprising a methylene oxide Japanese Patent Application Laid-Open No. 7-208647
  • an anion having a tertiary amine functional group or a quaternary ammonium functional group Production method of alkylene carbonate using exchange resin as catalyst (Japanese Unexamined Patent Publication No.
  • the reaction of synthesizing alkylene carbonate from alkylene oxide and carbon dioxide is economical and is a meaningful method from the viewpoint of the global environment.However, in order to achieve industrial production with the aim of reducing the environmental burden, There is a need to develop new processes that do not use metal catalysts, for which there are various problems.
  • a polar solvent having an amide group or the like promotes the synthesis of alkylene carbonate in carbon dioxide.
  • the invention has been completed. That is, the present invention is a novel method for producing alkylene carbonate by reacting alkylene oxide with carbon dioxide in the presence of a polar solvent having an amide group or a sulfur group.
  • the alkylene oxide used as a raw material in the present invention is represented by the following general formula (1): (Chemical 1)
  • R 2 , R 3, and 4 may be the same or different groups, and each represents hydrogen or a substituted or unsubstituted aryl group having 1 to 15 carbon atoms.
  • An alkyl group, an alkenyl group, a cycloalkyl group, and an arylalkyl group, and the substituents referred to herein are a halogen atom, an amino group, a nitro group, a canolepodinole group, a canolepoxyl group, Alkylene oxide represented by an alkoxy group, an acetate group, a hydroxyl group, a mercapto group, a sulfone group, a sulfonyl group, etc.).
  • alkylene oxides such as styrene oxide, ethylene oxide, pyrene oxide, butylene oxide, halogeno propylene oxide and the like, and cyclic oxides having substituents thereof
  • examples include alicyclic oxides such as cyclohexylene oxide and cyclohexylene oxides having a substituent, and arylalkyl oxides such as styrene oxides having a substituent.
  • alkylene oxides is a carbonate produced from the alkylene oxide, and is represented by the general formula (2):
  • the solvent used in the present invention is an organic compound having an amide group or a sulfur group, and has a general formula (3) (Chemical 3)
  • R 8 and R 9 each represent a substituted alkyl group, aryl group, or cycloalkyl group.
  • the substituent herein refers to a halogen atom, an alkoxy group, an acetyl group, a carboxyl group, Is an organic compound having a sulfinyl group.
  • the compound may be an organic compound composed of a combination of [Chemical Formula 3] and [Formula 4] in a single molecule. Specific examples include N, N—dimethylformamide, N, N—dimethylacetamide, N, N—getylformamide, N, N—getylacetamide, and N—methylpyrrolidone having an amide group.
  • these organic compounds and alkylene oxide are mixed and dissolved, and reacted with supercritical carbon dioxide.
  • the amount of the organic compound to be added is not particularly limited, but it can be used preferably in a range of 2 mol or less, more preferably in a range of 0.02 to 1 equivalent, relative to 1 equivalent of alkylenoxide. Preferably, it is used in the range of 0.1 to 0.6 equivalent.
  • the reaction usually proceeds suitably in a temperature range of 50 to 300 ° C, more preferably in a temperature range of 50 to 200 ° C, and most preferably 70 to 180 ° C. Proceed in the temperature range of C.
  • Supercritical or subcritical carbon dioxide pressure is usually preferably reaction proceeds at 6 0 kg / cm 2 or more pressure range, good Ri preferably of 6 0 kg / cm 2 ⁇ 1 2 0 kg / cm 2
  • the reaction can be carried out in a pressure range, and the reaction proceeds most suitably in a pressure range of 60 kg / cm 2 to 90 kg / cm 2 .
  • the pressure is set to 120 kg / cm 2 or more, although production is possible, it is not preferable because yield is low.
  • the reaction is carried out in a batch, semi-patch, or continuous flow system.
  • the reaction time is not particularly limited because the optimum time varies depending on the type of alkylene oxide, but is generally preferably about 5 minutes to 48 hours, more preferably about 5 minutes to 2 hours.
  • Example 1 the present invention will be described in more detail with reference to Examples. However, the present embodiment specifically describes the present invention, and the present invention is not limited to only these embodiments.
  • Example 1 the present embodiment specifically describes the present invention, and the present invention is not limited to only these embodiments.
  • Example 5 The reaction was carried out in the same manner as in Example 1. However, the reaction was carried out at a temperature of 160 ° C. The yield of the obtained polyethylene carbonate was 85%.
  • Example 5 The reaction was carried out in the same manner as in Example 1. However, the reaction was carried out at a temperature of 160 ° C. The yield of the obtained polyethylene carbonate was 85%.
  • Example 10 The reaction was carried out in the same manner as in Example 8. However, the reaction temperature was 70 ° C. The yield of the obtained styrene carbonate was 51%.
  • Example 10 The reaction was carried out in the same manner as in Example 8. However, the reaction temperature was 70 ° C. The yield of the obtained styrene carbonate was 51%.
  • Example 1 2 The reaction was carried out in the same manner as in Example 1. However, the test was performed by using tetramethyl urea 5 Ommo1 instead of N, N-dimethylformamide. The yield of the obtained styrene carbonate was 31%.
  • Example 1 2 The reaction was carried out in the same manner as in Example 1. However, the test was performed by using tetramethyl urea 5 Ommo1 instead of N, N-dimethylformamide. The yield of the obtained styrene carbonate was 31%.
  • Example 1 2 The yield of the obtained styrene carbonate was 31%.
  • Example 18 The reaction was carried out under the same conditions as in Example 1 except that 50 mmo 1 of (R) -styrene oxide was used instead of styrene oxide. Obtained Tylene carbonate was an R-isomer having a three-dimensional structure, and the yield was 62%.
  • Example 18
  • Example 19 The reaction was carried out under the same conditions as in Example 1 except that (S) monostyrene oxide was used in place of styrene oxide.
  • the obtained styrene carbonate was an S-isomer having a three-dimensional shape, and the yield was 59%.
  • alkylene carbonate can be produced without using a metal catalyst at all by using supercritical carbon dioxide and allowing an organic compound having an amide group or a sulfinyl group to be present. Can be done.
  • other impurities are not basically formed during this production process, it can be isolated by a simple method which has been conventionally established in crystallization, distillation and extraction. Therefore, the industrial advantages are extremely large, such as simplification of the manufacturing process and reduction of the cost for the catalyst.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé permettant d'effectuer la synthèse d'un carbonate d'alkylène à partir d'un oxyde d'alkylène au moyen de dioxyde de carbone supercritique sans avoir recours à des catalyseurs métal. Ce procédé consiste à faire réagir un oxyde d'alkylène avec le dioxyde de carbone à 60kg/cm3 ou plus en présence d'un solvant organique polaire possédant un groupe amido ou un groupe sulfinyle afin de préparer un carbonate d'alkylène.
PCT/JP2000/008358 2000-08-10 2000-11-28 Procede de production d'un compose de carbonate d'alkylene WO2002014302A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2000/243238 2000-08-10
JP2000243238A JP2002053573A (ja) 2000-08-10 2000-08-10 アルキレンカーボネート化合物の製造方法

Publications (1)

Publication Number Publication Date
WO2002014302A1 true WO2002014302A1 (fr) 2002-02-21

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PCT/JP2000/008358 WO2002014302A1 (fr) 2000-08-10 2000-11-28 Procede de production d'un compose de carbonate d'alkylene

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JP (1) JP2002053573A (fr)
WO (1) WO2002014302A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005082943A1 (fr) * 2004-03-01 2005-09-09 Toyota Jidosha Kabushiki Kaisha Composé de polymère novateur est procédé pour fabriquer celui-ci
JP4858973B2 (ja) * 2004-03-04 2012-01-18 独立行政法人産業技術総合研究所 環状カーボネート類の製造方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH069611A (ja) * 1992-06-19 1994-01-18 Asahi Chem Ind Co Ltd シクロアルキレンカーボネートの製造方法
JPH07165750A (ja) * 1993-12-10 1995-06-27 Japan Energy Corp トリフルオロプロピレンカーボナート及びその製造法
JPH11335372A (ja) * 1998-05-25 1999-12-07 Agency Of Ind Science & Technol カーボネート化合物の製造方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH069611A (ja) * 1992-06-19 1994-01-18 Asahi Chem Ind Co Ltd シクロアルキレンカーボネートの製造方法
JPH07165750A (ja) * 1993-12-10 1995-06-27 Japan Energy Corp トリフルオロプロピレンカーボナート及びその製造法
JPH11335372A (ja) * 1998-05-25 1999-12-07 Agency Of Ind Science & Technol カーボネート化合物の製造方法

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