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    PRODUCTION OF GAMMA, DELTA-UNSATURATED KETONE
    1.
    发明专利
    PRODUCTION OF GAMMA, DELTA-UNSATURATED KETONE 失效

    公开(公告)号：JPH10147548A

    公开(公告)日：1998-06-02

    申请号：JP31011997

    申请日：1997-11-12

    Applicant: BASF AG

    Inventor： ETZRODT HEINZ DR ,  STROEZEL MANFRED ,  WELLER DIETMAR DR ,  JAEDICKE HAGEN DR

    IPC: C07C45/69 ,  C07C45/67 ,  C07C45/71 ,  C07C45/76 ,  C07C49/203

    Abstract: PROBLEM TO BE SOLVED: To obtain the subject compound useful as an intermediate product for the production of perfumes, vitamin A, etc., by Carrol reaction in a specific solvent. SOLUTION: This γ,δ-unsaturated ketone, e.g. 2-methyl-2-hepten-6-one is obtained by using a cyclic carbonate of formula I (R -R are each H, methyl, etc.; R is H, isopropyl, etc.), e.g. ethylene carbonate, etc., a γ-lactone of formula II, e.g. γ-butyrolactone, etc., as a solvent, and reacting vinycarbinol or propargyl alcohol with an acetoacetic alkyl ester or diketene, then in the presence of an aluminum catalyst and at 120-220 deg.C, by thermal rearrangement reaction of the resultant acetoacetate to the aimed γ,δ-unsaturated ketone.

    PRODUCTION OF UNSATURATED KETONE
    2.
    发明专利
    PRODUCTION OF UNSATURATED KETONE 失效

    公开(公告)号：JPH11152245A

    公开(公告)日：1999-06-08

    申请号：JP25520098

    申请日：1998-09-09

    Applicant: BASF AG

    Inventor： TELES JOAQUIM HENRIQUE DR ,  RIEBER NORBERT DR ,  BREUER KLAUS DR ,  DEMUTH DIRK DR ,  HIBST HARTMUT ,  KAESHAMMER STEFAN DR ,  ETZRODT HEINZ DR ,  KAISER WULF DR

    IPC: B01J23/06 ,  C07B61/00 ,  C07C41/08 ,  C07C41/28 ,  C07C45/51 ,  C07C49/203

    Abstract: PROBLEM TO BE SOLVED: To obtain an unsaturated ketone which is an intermediate for synthesizing a useful flavor and a natural substance by reacting isopropenyl ether with a ketal of acetone with propene, etc., in the reaction between an allyl alcohol and isopropenyl ether. SOLUTION: An allyl alcohol of formula I (R to R are each H, an alkyl, an alkenyl or the like) or a propargyl alcohol of formula II is reacted with an isopropenyl ether of formula III (R is 1-4C alkyl) with forming a ketal of formula IV to give unsaturated ketones of formula V and formula VI. The isopropenyl ether of the formula III is obtained by reacting the ketal of formula IV with propyne or allylene or its mixture in a vapor phase at a raised temperature in the presence of a heterogeneous catalyst containing silicon or oxygen and zinc or cadmium. The ketal of the formula IV is resupplied for producing the isopropenyl ether of the formula III.

    5.
    发明专利
    未知

    公开(公告)号：ES2172277T3

    公开(公告)日：2002-09-16

    申请号：ES99117101

    申请日：1999-08-31

    Applicant: BASF AG

    Inventor： OOST CARSTEN DR ,  STROEZEL MANFRED ,  ETZRODT HEINZ DR ,  WELLER DIETMAR DR ,  BOCKSTIEGEL BERNHARD DR ,  REIMER KLAUS

    IPC: B01J31/14 ,  B01D3/00 ,  B01D3/14 ,  B01D3/32 ,  B01J10/00 ,  B01J19/24 ,  C07B61/00 ,  C07C45/67 ,  C07C45/68 ,  C07C45/82 ,  C07C49/203 ,  C07C67/54 ,  C07C69/72

    Abstract: Continuous production of 5-alken-2-one or 3,5-alkadien-2-one derivatives (I) by reacting a 1-alken-3-ol or 1-alkyn-3-ol derivative (II) with an alkyl acetoacetate (III) in a fractionation column to form an acetoacetate and alcohol involves (i) removing the alcohol and (ii) contacting the acetoacetate with catalyst in the lower part or bottom of the column to form (I). Continuous production of unsaturated ketones of formula (I) by reacting an unsaturated alcohol of formula (II) with an alkyl acetoacetate of formula (III) in the presence of an organoaluminum catalyst is carried out by: (a) reacting (II) with (III) on the plates of a fractionation column to form the acetoacetate of (II) and an alcohol of formula R OH; (b) removing the alcohol in the overhead stream from the column; (c) contacting the acetoacetate of (II) with the catalyst in the lower part or bottom of the column to form (I) and CO2; (d) removing the CO2 in the overhead stream from the column; and (e) withdrawing (I) in the bottoms stream from the column. R = 1-4C alkyl; R = 1-37C (un)saturated aliphatic hydrocarbyl (optionally substituted by methoxy groups), 4-12C cycloalkyl or 5-30C cycloalkylalkyl; and R = 1-5C alkyl.

    6.
    发明专利
    未知

    公开(公告)号：AT208363T

    公开(公告)日：2001-11-15

    申请号：AT98116052

    申请日：1998-08-26

    Applicant: BASF AG

    Inventor： TELES JOAQUIM HENRIQUE DR ,  RIEBER NORBERT DR ,  BREUER KLAUS DR ,  DEMUTH DIRK DR ,  HIBST HARTMUT PROF DR ,  KAESHAMMER STEFAN DR ,  ETZRODT HEINZ DR ,  KAISER WULF DR

    IPC: B01J23/06 ,  C07B61/00 ,  C07C41/08 ,  C07C41/28 ,  C07C45/51 ,  C07C49/203

    Abstract: Unsaturated ketones, comprising optionally substituted but-3-enyl and/or buta-2.3-dienyl methyl ketones, are prepared by: (a) reacting allyl alcohols and/or propargyl alcohols with isopropenyl ethers, with formation of ketals as by-product; (b) preparing isopropenyl ethers by catalytic gas phase reaction of ketals with propyne and/or allene; and (c) feeding the ketal from stage (a) into stage (b). The but-3-enyl methyl ketones of formula (Ia) and but-2,3-dienyl methyl ketones of formula (Ib) formed, allyl alcohols of formula (IIa) and/or propargyl alcohols of formula (IIb) and isopropenyl ethers (III) used as starting materials are ketals (IV). R1, R2, R3, R4, R5 = H or (cyclo)alkyl, (cyclo)alkenyl or ar(alk)yl (optionally containing O); or R1R2 = 5-6-membered ring; and R6 = 1-4C alkyl. (III) are prepared by the gas phase reaction of (IV) and propyne or allene at elevated temperature in the presence of a heterogeneous catalyst containing Zn or Cd plus Si and O.

    8.
    发明专利
    未知

    公开(公告)号：ES2184187T3

    公开(公告)日：2003-04-01

    申请号：ES98119215

    申请日：1998-10-12

    Applicant: BASF AG

    Inventor： OOST CARSTEN DR ,  STROEZEL MANFRED ,  ETZRODT HEINZ DR ,  BOCKSTIEGEL BERNHARD DR ,  JAEDICKE HAGEN DR ,  WELLER DIETMAR DR

    IPC: B01J31/02 ,  B01J31/14 ,  B01J31/22 ,  C07B61/00 ,  C07C45/67 ,  C07C45/68 ,  C07C49/203 ,  C07F5/06

    Abstract: Preparation of gamma , delta -unsaturated ketones (I) by modified Carroll reaction is catalysed by a stable liquid aluminum acetoacetate compound or mixture of such compounds. Some such catalyst mixtures are new. Preparation of gamma , delta -unsaturated ketones of formula (I) involves modified Carroll reaction of an allyl alcohol of formula (II) with diketene or an alkyl acetoacetate of formula (III) in presence of an aluminum catalyst. R1 = H or 1-20C, saturated or unsaturated, branched hydrocarbyl; R2 = 1-5C alkyl. The novelty is that the catalyst consists of an aluminum compound (or aluminum compound mixture) which is a stable liquid at room temperature and contains at least one alkyl acetoacetate-forming group and 1 or 2 alkoxy groups or exclusively alkyl acetoacetate forming groups which are esterified sec. butanol or isobutanol or with at least two different alkanols. Independent claims are included for: (1) new mixtures of aluminum tris-acetoacetates of formula (V) which are liquid at room temperature; and (2) the preparation of mixtures as in (1). R3 = 1-5C alkyl, preferably Me or Et; R4 = 3-10C alkyl, preferably CHMe2, CH(Me)Et, CMe3 or CH(Me)-C3H7; R5 = 1-10C alkyl, preferably Me, Et, CHMe2, CH(Me)Et or CH(Me)-C3H7; provided that R3-R5 are not all the same. A further Independent claim relates to the continuous preparation of compounds (V) (or their mixtures), having the narrower proviso that R3-R5 can only be the same if they are -CH(Me)Et or -CH2CHMe2, which are liquid at room temperature. The process involves continuously reacting 1 mole of aluminum alcoholate of formula (VI) with 3-10 moles of (III), or with at least 3 moles of a mixture of 2 or 3 different compounds (III), optionally dissolved in an inert solvent. Reaction is at 100-250 (preferably 150-200) degrees C and 1-100 (preferably 1-10) bars with a dwell time of 5-120 (preferably 15-45) minutes, the pressure and temperature being such that no gas phase is formed in the reaction vessel. R6 = 2-10C alkyl, preferably -CH2CHMe2, -CH(Me)Et or -CH(Me)C3H7; provided that R2 and R6 can only be the same if they are -CH(Me)Et or -CH2CHMe2.

    9.
    发明专利
    未知

    公开(公告)号：DE59805594D1

    公开(公告)日：2002-10-24

    申请号：DE59805594

    申请日：1998-10-12

    Applicant: BASF AG

    Inventor： OOST CARSTEN DR ,  STROEZEL MANFRED ,  ETZRODT HEINZ DR ,  BOCKSTIEGEL BERNHARD DR ,  JAEDICKE HAGEN DR ,  WELLER DIETMAR DR ,  LAUPICHLER LOTHAR DR ,  REIMER KLAUS

    IPC: B01J31/02 ,  B01J31/14 ,  B01J31/22 ,  C07B61/00 ,  C07C45/67 ,  C07C45/68 ,  C07C49/203 ,  C07F5/06

    Abstract: Preparation of gamma , delta -unsaturated ketones (I) by modified Carroll reaction is catalysed by a stable liquid aluminum acetoacetate compound or mixture of such compounds. Some such catalyst mixtures are new. Preparation of gamma , delta -unsaturated ketones of formula (I) involves modified Carroll reaction of an allyl alcohol of formula (II) with diketene or an alkyl acetoacetate of formula (III) in presence of an aluminum catalyst. R1 = H or 1-20C, saturated or unsaturated, branched hydrocarbyl; R2 = 1-5C alkyl. The novelty is that the catalyst consists of an aluminum compound (or aluminum compound mixture) which is a stable liquid at room temperature and contains at least one alkyl acetoacetate-forming group and 1 or 2 alkoxy groups or exclusively alkyl acetoacetate forming groups which are esterified sec. butanol or isobutanol or with at least two different alkanols. Independent claims are included for: (1) new mixtures of aluminum tris-acetoacetates of formula (V) which are liquid at room temperature; and (2) the preparation of mixtures as in (1). R3 = 1-5C alkyl, preferably Me or Et; R4 = 3-10C alkyl, preferably CHMe2, CH(Me)Et, CMe3 or CH(Me)-C3H7; R5 = 1-10C alkyl, preferably Me, Et, CHMe2, CH(Me)Et or CH(Me)-C3H7; provided that R3-R5 are not all the same. A further Independent claim relates to the continuous preparation of compounds (V) (or their mixtures), having the narrower proviso that R3-R5 can only be the same if they are -CH(Me)Et or -CH2CHMe2, which are liquid at room temperature. The process involves continuously reacting 1 mole of aluminum alcoholate of formula (VI) with 3-10 moles of (III), or with at least 3 moles of a mixture of 2 or 3 different compounds (III), optionally dissolved in an inert solvent. Reaction is at 100-250 (preferably 150-200) degrees C and 1-100 (preferably 1-10) bars with a dwell time of 5-120 (preferably 15-45) minutes, the pressure and temperature being such that no gas phase is formed in the reaction vessel. R6 = 2-10C alkyl, preferably -CH2CHMe2, -CH(Me)Et or -CH(Me)C3H7; provided that R2 and R6 can only be the same if they are -CH(Me)Et or -CH2CHMe2.

    10.
    发明专利
    未知

    公开(公告)号：DK0909750T3

    公开(公告)日：2002-10-14

    申请号：DK98119215

    申请日：1998-10-12

    Applicant: BASF AG

    Inventor： OOST CARSTEN DR ,  STROEZEL MANFRED ,  ETZRODT HEINZ DR ,  BOCKSTIEGEL BERNHARD DR ,  JAEDICKE HAGEN DR ,  WELLER DIETMAR DR ,  LAUPICHLER LOTHAR DR ,  REIMER KLAUS

    IPC: B01J31/02 ,  B01J31/14 ,  B01J31/22 ,  C07B61/00 ,  C07C45/67 ,  C07C45/68 ,  C07C49/203 ,  C07F5/06

    Abstract: Preparation of gamma , delta -unsaturated ketones (I) by modified Carroll reaction is catalysed by a stable liquid aluminum acetoacetate compound or mixture of such compounds. Some such catalyst mixtures are new. Preparation of gamma , delta -unsaturated ketones of formula (I) involves modified Carroll reaction of an allyl alcohol of formula (II) with diketene or an alkyl acetoacetate of formula (III) in presence of an aluminum catalyst. R1 = H or 1-20C, saturated or unsaturated, branched hydrocarbyl; R2 = 1-5C alkyl. The novelty is that the catalyst consists of an aluminum compound (or aluminum compound mixture) which is a stable liquid at room temperature and contains at least one alkyl acetoacetate-forming group and 1 or 2 alkoxy groups or exclusively alkyl acetoacetate forming groups which are esterified sec. butanol or isobutanol or with at least two different alkanols. Independent claims are included for: (1) new mixtures of aluminum tris-acetoacetates of formula (V) which are liquid at room temperature; and (2) the preparation of mixtures as in (1). R3 = 1-5C alkyl, preferably Me or Et; R4 = 3-10C alkyl, preferably CHMe2, CH(Me)Et, CMe3 or CH(Me)-C3H7; R5 = 1-10C alkyl, preferably Me, Et, CHMe2, CH(Me)Et or CH(Me)-C3H7; provided that R3-R5 are not all the same. A further Independent claim relates to the continuous preparation of compounds (V) (or their mixtures), having the narrower proviso that R3-R5 can only be the same if they are -CH(Me)Et or -CH2CHMe2, which are liquid at room temperature. The process involves continuously reacting 1 mole of aluminum alcoholate of formula (VI) with 3-10 moles of (III), or with at least 3 moles of a mixture of 2 or 3 different compounds (III), optionally dissolved in an inert solvent. Reaction is at 100-250 (preferably 150-200) degrees C and 1-100 (preferably 1-10) bars with a dwell time of 5-120 (preferably 15-45) minutes, the pressure and temperature being such that no gas phase is formed in the reaction vessel. R6 = 2-10C alkyl, preferably -CH2CHMe2, -CH(Me)Et or -CH(Me)C3H7; provided that R2 and R6 can only be the same if they are -CH(Me)Et or -CH2CHMe2.

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