公开(公告)号：JP2001270889A

公开(公告)日：2001-10-02

申请号：JP2001059147

申请日：2001-03-02

Applicant: BASF AG

Inventor： WEGNER CHRISTOPH ,  JOHN MICHAEL

IPC: C07F9/54

Abstract: PROBLEM TO BE SOLVED: To provide a method for manufacturing 3,7,11-trimethyldodeca-2,4,6,10- tetraen-1-yl phosphonium salt. SOLUTION: The method for manufacturing a phosphonium salt expressed by general formula I (wherein, R is an aryl; and X is an anion of an organic acid or an inorganic acid selected from the group consisting of hydrohalogenic acids, sulfuric acid, sulfonic acid, phosphoric acid and 1-6C alkanoic acids) comprises a process in which 3,7,11-trimethyldodeca-1,4,6,10-tetraen-3-ol expressed by formula II is made to react with a triarylphosphane and an organic or inorganic acid shown above. The method is carried out by the following two steps: (a) at first, a process in which a tertiary phosphonium salt expressed by formula III (wherein, R and X are same as defined above) is produced at a temperature of -20 to 40 deg.C; and (b) a process in which the resultant tertiary phosphonium salt of formula III is rearranged to a primary phosphonium salt of formula I at a temperature of 40-100 deg.C.

公开(公告)号：JPH11130787A

公开(公告)日：1999-05-18

申请号：JP22461398

申请日：1998-08-07

Applicant: BASF AG

Inventor： WEGNER CHRISTOPH ,  PAUST JOACHIM ,  JOHN MICHAEL

IPC: C07C403/24 ,  C07C11/21 ,  C07F9/54

Abstract: PROBLEM TO BE SOLVED: To produce a 3,7,11-trimethyldodeca-2,4,6,10-tetraene-1-yl-phoshonium salt at a high rate of E, the salt providing a high E/Z selectivity in synthesizing lycopene, by reacting vinylpseudoionol with two kinds of specific compounds. SOLUTION: This compound of formula II (R is a aryl; and X is Cn H2n+1 -So3 , Ar-SO3 or CF3 -SO3 ) is obtained by reacting an alcohol of formula I with triarylphosphine (e.g. triphenylphosphine) and a sulfonic acid [pref. methane sulfonic acid (70%)] of any formulas Cn H2n+1 -SO3 H ((n) is 1 to 4), Ar-So3 H (Ar is a phenyl or tolyl) or CF3 -SO3 H in a solvent (pref. acetic acid, etc.). The compound of formula II is pref. used for a Witting reaction with 2,7- dimethyl-2,4,6-octatrienedial so as to produce a lycopene.

公开(公告)号：DE19840746A1

公开(公告)日：2000-03-09

申请号：DE19840746

申请日：1998-09-07

Applicant: BASF AG

Inventor： JAEDICKE HAGEN ,  JOHN MICHAEL

IPC: C07C45/71 ,  C07B61/00 ,  C07C45/67 ,  C07C49/203 ,  C07C45/68 ,  C07C45/65 ,  C07C49/255

Abstract: The invention relates to a method for producing gamma , delta -unsaturated ketones of general formula (I) by reacting an acetoacetic alkyl ester with an allyl alcohol or a propargyl alcohol of general formula (II) in which R can represent H or a saturated or unsaturated, branched hydrocarbon radical which is optionally substituted by methoxy groups and which has 1 to 33 C-atoms, and the dashed line can represent another bond between the C-atoms carrying the same. The reaction is carried out at temperatures ranging from 150 to 220 DEG C in an optionally modified Carroll reaction, in the presence of an aluminum catalyst, and by distilling off the alkanol formed during the reaction. The inventive method is characterized in that an acetoacetic ester of general formula (III) is used as an acetoacetic alkyl ester in which R represents an alkyl group with 1 to 4 C-atoms.

公开(公告)号：DE59806098D1

公开(公告)日：2002-12-12

申请号：DE59806098

申请日：1998-08-07

Applicant: BASF AG

Inventor： WEGNER CHRISTOPH ,  PAUST JOACHIM ,  JOHN MICHAEL

IPC: C07C403/24 ,  C07C11/21 ,  C07F9/54

Abstract: New and known phosphonium salts are prepared by reacting an alcohol with a triarylphosphine and a sulfonic acid in a solvent. Preparation of phosphonium salts of formula (I) comprises reaction of 3,7,11-trimethyldodeca-1,4,6,10-tetraen-3-ol (II) with a triarylphosphine and a sulfonic acid of formula XH (III) in a solvent. X = Q-SO3 ; Q = CnH2n+1, Ar' or CF3; R = aryl; n = 1, 2, 3 or 4; Ar' = phenyl or toluyl Independent claims are included for: (1) compounds (I) when Q is other than Ar'; and (2) preparation of lycopine by reaction of a compound of formula (I) with 2,7-dimethyl-2,4,6- octatrienedial.

公开(公告)号：ES2186065T3

公开(公告)日：2003-05-01

申请号：ES98114885

申请日：1998-08-07

Applicant: BASF AG

Inventor： WEGNER CHRISTOPH ,  PAUST JOACHIM ,  JOHN MICHAEL

IPC: C07C403/24 ,  C07C11/21 ,  C07F9/54

Abstract: New and known phosphonium salts are prepared by reacting an alcohol with a triarylphosphine and a sulfonic acid in a solvent. Preparation of phosphonium salts of formula (I) comprises reaction of 3,7,11-trimethyldodeca-1,4,6,10-tetraen-3-ol (II) with a triarylphosphine and a sulfonic acid of formula XH (III) in a solvent. X = Q-SO3 ; Q = CnH2n+1, Ar' or CF3; R = aryl; n = 1, 2, 3 or 4; Ar' = phenyl or toluyl Independent claims are included for: (1) compounds (I) when Q is other than Ar'; and (2) preparation of lycopine by reaction of a compound of formula (I) with 2,7-dimethyl-2,4,6- octatrienedial.

公开(公告)号：DE10103708A1

公开(公告)日：2002-08-01

申请号：DE10103708

申请日：2001-01-26

Applicant: BASF AG

Inventor： WEGNER CHRISTOPH ,  JOHN MICHAEL

IPC: C07C5/22 ,  C07C11/21

Abstract: The invention relates to a method for the thermal isomerization of a mixture of all-E-lycopene and its Z-isomers in any combination, producing an increase in the all-E content. Said method is characterized in that the isomerization takes place in a polar solvent, in which lycopene is poorly soluble.

公开(公告)号：DE10009459C1

公开(公告)日：2001-06-07

申请号：DE10009459

申请日：2000-03-02

Applicant: BASF AG

Inventor： WEGNER CHRISTOPH ,  JOHN MICHAEL

IPC: C07F9/54

Abstract: Preparation of triaryl-3,7,11-trimethyldodeca-2,4,6,10-tetraen-1-yl-p hosphonium salts (I) comprises: (1) reacting 3,7,11-trimethyldodeca-1,4,6,10-tetraen-3-ol with triarylphosphane and a hydrohalic, sulfuric, sulfonic, phosphoric or 1-6C alkanoic acid at -20 to 40 [deg] C to give 3,7,11-trimethyldodeca-1,4,6,10-tetraen-3-yl-phosphonium salt (III); and (2) rearranging (III) at 40-100 [deg] C to form the primary salt (I). Preparation of triaryl-3,7,11-trimethyldodeca-2,4,6-10-tetraen-1-yl-p hosphonium salts of formula (I) comprises: (1) reacting 3,7,11-trimethyldodeca-1,4,6,10-tetraen-3-ol with triarylphosphane and a hydrohalic, sulfuric, sulfonic, phosphoric or 1-6C alkanoic acid at -20 to 40 [deg] C to give 3,7,11-trimethyldodeca-1,4,6,10-tetraen-3-yl-phosphonium salt (III); and (2) rearranging (III) at 40-100 [deg] C to form the primary salt (I). [Image] R : aryl; and X : the anion of hydrohalic, sulfuric, sulfonic, phosphoric or 1-6 C alkanoic acid.

公开(公告)号：CA2343521A1

公开(公告)日：2000-03-16

申请号：CA2343521

申请日：1999-09-02

Applicant: BASF AG

Inventor： JOHN MICHAEL ,  JAEDICKE HAGEN

IPC: C07C45/71 ,  C07B61/00 ,  C07C45/67 ,  C07C49/203

Abstract: The invention relates to a method for producing .gamma.,.delta.-unsaturated ketones of general formula (I) by reacting an acetoacetic alkyl ester with a n allyl alcohol or a propargyl alcohol of general formula (II) in which R1 can represent H or a saturated or unsaturated, branched hydrocarbon radical whic h is optionally substituted by methoxy groups and which has 1 to 33 C-atoms, a nd the dashed line can represent another bond between the C-atoms carrying the same. The reaction is carried out at temperatures ranging from 150 to 220 ~C in an optionally modified Carroll reaction, in the presence of an aluminum catalyst, and by distilling off the alkanol formed during the reaction. The inventive method is characterized in that an acetoacetic ester of general formula (III) is used as an acetoacetic alkyl ester in which R2 represents a n alkyl group with 1 to 4 C-atoms.

公开(公告)号：ES2282407T3

公开(公告)日：2007-10-16

申请号：ES02719721

申请日：2002-01-24

Applicant: BASF AG

Inventor： WEGNER CHRISTOPH ,  JOHN MICHAEL

IPC: C07C5/22 ,  C07C11/21

Abstract: Procedimiento para la isomerización térmica de una mezcla de licopina-todo-E y su isómero Z, en cualquier composición, con aumento de la proporción en todo-E, caracterizado porque la isomerización tiene lugar en un disolvente polar.

公开(公告)号：DK1358139T3

公开(公告)日：2007-07-02

申请号：DK02719721

申请日：2002-01-24

Applicant: BASF AG

Inventor： WEGNER CHRISTOPH ,  JOHN MICHAEL

IPC: C07C5/22 ,  C07C11/21

Abstract: The present invention relates to a process for the thermal isomerization of a mixture of all-E-lycopene and its Z isomers of any composition to increase the proportion of all-E, wherein the isomerization takes place in a polar solvent in which lycopene is only slightly soluble.