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公开(公告)号：JPH1053548A
公开(公告)日：1998-02-24
申请号：JP12040397
申请日：1997-05-12
Applicant: DEGUSSA
Inventor： HUEBNER FRANK DR , KRILL STEFFEN DR , DRAPAL BERND , HERUMAN SHIYUMITSUTO , HUTHMACHER KLAUS DR , TANNER HERBERT DR
Abstract: PROBLEM TO BE SOLVED: To obtain the subject compound in high yield by reacting a trimethylcyclohexenedione with an acylating agent in the presence of a protonic acid. SOLUTION: 3,3,5-Trimethylcyclohex-2-ene-1,4-dione is reacted with an acylating agent in the presence of a protonic acid and the formed trimethylhydroquinone ester is successively saponified to give the objective compound. A trifluoromethanesulfonic acid, chlorosulfonic acid, polyphosphoric acid, fuming sulfuric acid or a mixture of these acids is used as the protonic acid. The amount of the acylating agent is 2-4mol based on 1mol of 3,5,5- trimethylcyclohex-2-ene-1,4-dione and that of the acid is 0.1-50wt.%. The saponification is carried out in the presence of a phase mediation agent (e.g. n-butanol). The amount of the acid used is reduced and the saponification can also be extremely readily carried out.
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公开(公告)号：JP2001114723A
公开(公告)日：2001-04-24
申请号：JP2000312411
申请日：2000-10-12
Applicant: DEGUSSA
Inventor： NONGYUAN SHI , HUEBNER FRANK , DRAPAL BERND , PETER RAINER , KRILL STEFFEN DR , HUTHMACHER KLAUS DR , WECKBECKER CHRISTOPH
Abstract: PROBLEM TO BE SOLVED: To obtain the subject ketone compounds in good yield by improving space-time yield in reacting tertiary propargyl alcohol with an alkenyl ether. SOLUTION: A time required for reaction of tertiary propargyl alcohol with an alkenyl ether is shortened and the product can be obtained in high yield by selecting an aliphatic sulfonic acid or a sulfonic acid salt as a catalyst.
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公开(公告)号：JPH11246549A
公开(公告)日：1999-09-14
申请号：JP35904798
申请日：1998-12-17
Applicant: DEGUSSA
Inventor： KRILL STEFFEN DR , HUEBNER FRANK DR , HAHN RAINER DR , WEIGEL HORST , HUTHMACHER KLAUS DR
IPC: C07B61/00 , C07D311/72
Abstract: PROBLEM TO BE SOLVED: To industrially obtain an α-tocopherol ester useful as a feed additive, etc., while saving raw materials and reducing the number of processes by reacting a diacetylated substituted hydroquinone with a specific compound in the presence of a catalytic action compound. SOLUTION: This method for producing an α-tocopherol ester of formula I (R1 is a 1-20C alkyl; R3 -R5 are each H or a 1-3C alkyl) comprises reacting (A) a hydroquinone mono- or di-ester of formula II (R2 is a 1-20C alkyl) with (B) an allyl alcohol derivative of formula III [(n) is 0-5; L is a hydroxyl group, a halogen group, an acetoxy group or the like] or (C) an allyl alcohol of formula IV in the presence of (D) a zinc halide (for example, zinc dichloride) and (E) a proton-releasing acid (preferably hydrochloric acid, hydrobromic acid, sulfuric acid, trifluoromethanesulfonic acid, etc.), at a temperature of 25-100 deg.C.
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公开(公告)号：JPH10168023A
公开(公告)日：1998-06-23
申请号：JP25839597
申请日：1997-09-24
Applicant: DEGUSSA
Inventor： KRILL STEFFEN DR , GIRAY GUENES , HUTHMACHER KLAUS DR , HUEBNER FRANK DR , TANNER HERBERT DR
IPC: B01J23/78 , B01J27/138 , B01J27/232 , C07B61/00 , C07C45/67 , C07C49/603
Abstract: PROBLEM TO BE SOLVED: To provide a method for producing 3,5,5-trimethylcyclohex-3-en-1-one by isomerizing 3,5,5-trimethylcyclohex-2-en-1-one (α-isophorone) in a liquid phase in the presence of a heterogeneous catalyst. SOLUTION: In the case of isomerizing 3,5,5-trimethylcyclohex-2-en-1-one (α-isophorone) in a liquid phase in the presence of a heterogeneous catalyst, an oxide, a mixed oxide or an insoluble salt of an element of the groups IIa, VIII, Ib, IIIa and Va of the periodic table is used as the catalyst and the isomerization is carried out without adding an organic base to produce 3,5,5- trimethylcyclohex-3-en-1-one (β-isophorone).
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公开(公告)号：JPH10109955A
公开(公告)日：1998-04-28
申请号：JP25839697
申请日：1997-09-24
Applicant: DEGUSSA
Inventor： KRILL STEFFEN DR , GIRAY GUENES , HUEBNER FRANK , RAINER HAHN , HUTHMACHER KLAUS , TANNER HERBERT
IPC: B01J23/02 , B01J23/75 , B01J23/755 , C07B61/00 , C07C45/67 , C07C45/82 , C07C45/83 , C07C49/603
Abstract: PROBLEM TO BE SOLVED: To obtain the subject compound useful as a raw material for medicines with slight formation of by-products in excellent space and time yield and in a high conversion ratio, by taking out a mixture containing a specific amount of β-isophorone from a reaction solution during isomerization of α-isophorone by distillation. SOLUTION: While (A) 3,5,5-trimethylcyclohexa-2-en-1-one is isomerized by (B) a catalyst [e.g. a (mixed) oxide of the groups IIa and VIII of the periodic table, to be concrete, Ca or Mg(mixed) oxide or Co or Ni (mixed) oxide], a mixture containing 0.5-75wt.%, preferably 0.5-40wt.% of 3,5,5- trimethylcyclohexa-3-en-I-one (β-isophorone) is taken out by distillation and β-isophorone is isolated by vacuum distillation from the mixture.
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Patent Agency Ranking
公开(公告)号：JP2001278835A
公开(公告)日：2001-10-10
申请号：JP2001067447
申请日：2001-03-09
Applicant: DEGUSSA
Inventor： MAASSEN RALF , KRILL STEFFEN DR , HUTHMACHER KLAUS DR
Abstract: PROBLEM TO BE SOLVED: To enable the oxidation of trimethylphenol into trimethyl-p- benzoquinone in a good yield while surely excluding the danger of explosion of a reactional mixture and also to avoid the defects of existing methods which are enumerated in the evaluation of prior art. SOLUTION: A mixture of water with a 8-11C neocarboxylic acid, favorably neodecanoic acid is used as a solvent system. A copper (II) halide activated by being added with an alkaline earth metal halide, an alkali metal halide, a transition metal halide or a rare earth element halide is used as an especially preferable catalyst.
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公开(公告)号：JP2001151721A
公开(公告)日：2001-06-05
申请号：JP2000312413
申请日：2000-10-12
Applicant: DEGUSSA
Inventor： MAASSEN RALF , KRILL STEFFEN DR , JAEGER BARBARA , HUTHMACHER KLAUS DR
IPC: B01J27/122 , C07B61/00 , C07C46/08 , C07C50/02
Abstract: PROBLEM TO BE SOLVED: To provide a new method for producing 2,3,5-trimethyl-p-benzoquinone capable of partially settling significant defects described in conventional technology level and relative to charged material cost, post-treatment cost and especially viewpoint of safety technology in industrially preventing degradation. SOLUTION: This method comprises carrying out the oxidation of phenol, at 20-120 deg.C, consisting of water and a 5-10C fatty alcohol or water, a 1-4C fatty alcohol and an aromatic hydrocarbon, in the presence of a catalyst system comprising a copper halide and a transition metal halide of a group consisting of Fe, Cr, Mn, Co, Ni and Zn or a rare earth element halide.
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公开(公告)号：JPH1053553A
公开(公告)日：1998-02-24
申请号：JP12439297
申请日：1997-05-14
Applicant: DEGUSSA
Inventor： HAHN RAINER DR , GORA ULRICH , HUTHMACHER KLAUS DR , HUEBNER FRANK DR , KRILL STEFFEN DR
IPC: B01J31/22 , C07B61/00 , C07C45/34 , C07C49/603
Abstract: PROBLEM TO BE SOLVED: To provide an improved method for producing 3,5,5- trimethylcyclohex-2-ene-1,4-dione (KIP) by oxidizing 3,5,5-trimethylcyclohex-3- ene-1-one (β-IP) in the presence of a manganese complex-like catalyst and an additive having a fixed catalytic action. SOLUTION: 3,5,5-Trimethylcyclohex 3-ene-1-one is oxidized in the presence of a manganese complex-like catalyst and another compound X having a catalytic action selected from the group consisting of an organic acid having 2-7pKa value, an aldehyde corresponding to the organic acid, a 1-4C-containing aliphatic alcohol or phenol, a compound capable of forming an enol structure and lithium sulfate. In the case, the amount of the compound X used is in a molar ratio to the catalyst of (1:1) to (100:1) and the amount of β-IP based on the whole amount of the mixture is at least more than 15%.
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公开(公告)号：AT252533T
公开(公告)日：2003-11-15
申请号：AT00121161
申请日：2000-09-29
Applicant: DEGUSSA
Inventor： NONGYUAN SHI DR , HUEBNER FRANK DR , DRAPAL BERND , PETER RAINER , KRILL STEFFEN DR , HUTHMACHER KLAUS DR , WECKBECKER CHRISTOPH DR
Abstract: A process for the preparation of unsaturated 4,5-alleneketones comprises reaction of a tertiary propargylalcohol with an alkenylalkylether or a ketal in the presence of an aliphatic sulfonic acid or salt. A process for the preparation of unsaturated 4,5-alleneketones (I) of formula (1) comprises reaction of a tertiary propargylalcohol of formula (2) with an alkenylalkylether of formula (3) or a ketal of formula (4) in the presence of an aliphatic sulfonic acid of formula (5) or sulfonic acid salt of formula (6). An Independent claim is included for a process for the preparation of unsaturated 3,5-dieneketones and their corresponding saturated ketones by isomerization or hydrogenation of 4,5-alleneketones (I) of formula (1). R -O-C(R )=CH-R (3), R SO3H (5), R SO3M (6) R , R = H, 1-20C alkyl, aryl or alkylaryl or R and R may combine to form a 5-6 membered ring; R , R = 1-4C alkyl; R ,R = 1-4C alkyl; R , R = halogen, 1-20C alkyl or cycloalkyl optionally substituted with halogen, R is additionally an optionally substituted aryl; and M = cation of an organic or inorganic base.
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公开(公告)号：AT243182T
公开(公告)日：2003-07-15
申请号：AT01710004
申请日：2001-02-01
Applicant: DEGUSSA
Inventor： MAASSEN RALF DR , KRILL STEFFEN DR , HUTHMACHER KLAUS DR
Abstract: Production of 2,3,5-trimethyl-p-benzoquinone comprises the oxidation of 2,3,5- or 2,3,6-trimethylphenol with oxygen or an oxygen-containing gas in a mixture of water and an 8-11C neocarboxylic acid and in the presence of a catalyst containing one or more copper(II) salts at 50-100 degrees C.
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