Abstract: Alkyl tert-alkyl ethers are cleaved into the corresponding isoolefins and alkanols by a process comprising acid-catalyzed reactive distilling an alkyl tert-alkyl ether fed into the reaction zone of a reactive distillation apparatus as an azeotrope of the alkyl tert-alkyl ether and the corresponding alkanol, wherein the reactive distillation apparatus is configured from bottom to top as a bottom zone, at least one distillation zone and a reaction zone. The process is suitable for the cleavage of primary, secondary and tertiary alkyl tert-alkyl ethers, in particular MTBE.
Type:
Grant
Filed:
April 25, 2001
Date of Patent:
April 22, 2003
Assignee:
OXENO Olefinchemie GmbH
Inventors:
Michael Sakuth, Axel Tuchlenski, Dieter Reusch, Andreas Beckman
Abstract: Olefins having from 5 to 24, in particular from 5 to 12, carbon atoms are hydroformylated by reacting an olefin or a mixture of olefins in the presence of an unmodified cobalt catalyst in a single-stage process in a reactor at a temperature of from 100° C. to 220° C. and a pressure of from 100 bar to 400 bar, to obtain an aldehyde, an alcohol or a mixture thereof. An aqueous bottom phase and an organic phase are present in the reactor, the aqueous bottom phase is mixed with the organic phase, and a concentration of the cobalt catalyst, calculated as metallic cobalt, in the aqueous bottom phase is in the range from 0.4 to 1.7% by mass based on the total weight of the aqueous bottom phase. A level of the aqueous bottom phase in the reactor is kept constant during steady-state operation.
Type:
Application
Filed:
July 24, 2002
Publication date:
February 13, 2003
Applicant:
OXENO OLEFINCHEMIE GMBH
Inventors:
Stefan Drees, Bernhard Scholz, Alfred Kaizik, Walter Toetsch, Wilfried Bueschken, Martin Trocha
Abstract: Aldehydes are prepared by a process, which comprises:
hydroformylating olefins having 3 to 21 carbon atoms under an atmosphere of CO/H2 in the presence of a rhodium catalyst in a hydroformylation reactor; and
upon discharging the reaction product from the reactor,
a) separating the discharged material into a gaseous phase and a liquid phase,
b) separating the liquid phase into a top fraction containing unconverted olefins and aldehydes and a bottoms fraction containing the rhodium catalyst, and
c) cooling the bottoms fraction below the temperature of the material discharged from the hydroformylation reactor and feeding a gas containing carbon monoxide into the bottoms fraction.
Type:
Grant
Filed:
September 25, 2001
Date of Patent:
December 31, 2002
Assignee:
Oxeno Olefinchemie GmbH
Inventors:
Klaus-Diether Wiese, Martin Trocha, Dirk Röettger, Walter Töetsch, Alfred Kaizik, Wilfried Büschken
Abstract: Catalytic multiphase reactions are conducted by a process, comprising:
conducting the catalytic multiphase reactions in a tube reactor, wherein the catalyst is present in the continuous phase and at least one starting material is present in a dispersed phase and the loading factor B of the tube reactor is equal to or greater than 0.8.
Abstract: The invention relates to a catalytic process for carrying out multiphase reactions in a tubular reactor, with the catalyst being present in the continuous phase and at least one starting material in a disperse phase and the loading factor B of the tubular reactor being equal to or greater than 0.8. The process is especially suitable in particular for the hydroformylation of olefins. The aldehydes thus prepared can ideally be used for the preparation of alcohols, carboxylic acids or in aldol condensations.
Abstract: Olefins are hydroformylated to give alcohols and/or aldehydes in a plurality of hydroformylation stages, each of which comprises:
a) hydroformylating olefins having a carbon atom content of 6 to 24 carbon atoms in the presence of a cobalt- or rhodium catalyst in a reactor to the point of conversion of olefin reactant to product of 20 to 98%;
b) removing the catalyst from the resulting liquid discharged from the reactor;
c) separating the resulting liquid hydroformylation mixture into a low-boiler fraction comprising olefins and paraffins, and a bottoms fraction comprising aldehydes and/or alcohols; and
d) reacting the olefins present in the low-boiler fraction in subsequent process stages comprising steps a, b and c and combining the bottoms fractions of process steps c) of all process stages.
Type:
Grant
Filed:
July 16, 2001
Date of Patent:
November 19, 2002
Assignee:
OXENO Olefinchemie GmbH
Inventors:
Bernhard Scholz, Franz Nierlich, Alfred Kaizik, Dieter Hess, Wilfried Bueschken, Klaus-Diether Wiese, Dirk Roettger, Guido Protzmann
Abstract: &agr;,&bgr;-Unsaturated keto compounds are prepared by base-catalyzed aldol condensation of aldehydes and/or ketones having from 1 to 15 carbon atoms, comprising:
reacting the aldehydes and/or ketones with an aqueous catalyst solution under adiabatic reaction conditions; and
separating the reaction mixture obtained by rapid distillation into a top product comprising water, aldehyde and/or ketone and a bottom product comprising &agr;,&bgr;-unsaturated keto compounds and aqueous catalyst phase.
Abstract: The invention relates to a process for separating dibutenes into an n-octene-containing fraction and a dimethylhexene-containing fraction. The fractions can be processed further separately to the corresponding C9 carboxylic acids and C9 alcohols (isononanols). Successor products of the C9 carboxylic acids include, for example, vinyl esters. Successor products of the C9 alcohols include plasticizers.
Abstract: The invention relates to a process for preparing higher oxo alcohols from mixtures of isomeric olefins having from 5 to 24 carbon atoms by hydroformylation in the presence of a catalyst at elevated temperature and at elevated pressure, in which the hydroformylation is carried out in one stage, the olefin conversion rate for one pass is restricted to from 40 to 90% to produce a reaction mixture, and the reaction mixture is selectively hydrogenated.
Type:
Grant
Filed:
September 15, 1999
Date of Patent:
June 18, 2002
Assignee:
Oxeno Olefinchemie GmbH
Inventors:
Alfred Kaizik, Bernhard Scholz, Walter Toetsch, Martin Trocha, Wilfried Bueschken, Franz Nierlich
Abstract: A process for preparing aldehydes having from 4 to 25 carbon atoms by catalytic hydroformylation of the corresponding olefins, wherein the catalyst used comprises a metal of transition group 8 of the Periodic Table in the presence of a ligand A of the formula I
where
X=As, Sb or P and
R1,R2,R3: are each a substituted or unsubstituted aliphatic, cycloaliphatic or aromatic hydrocarbon radical having from 1 to 50 carbon atoms,
where two of the radicals R1, R2, R3 can be covalently linked with the proviso that at least one of the hydrocarbon radicals R1, R2, R3 contains a heteroatom selected from the group consisting of O, S, N, F, Cl, Be, I, Se and Te, and a ligand B of the formula II
where R4, R5, R6: are each a substituted or unsubstituted aliphatic, cycloaliphatic or aromatic hydrocarbon having from 1 to 50 carbon atoms,
where two of the radicals R4, R5 and R6 can be covalently linked.
Abstract: The present invention is a process for preparing C4-25 aldehydes by hydroformylating the corresponding C3-24 olefins in the presence of a cobalt hydroformylation catalyst, and catalytically decomposing the formic acid formed in the hydroformylation reaction or in the subsequent catalyst work-up. The aldehydes so produced may be hydrogenated to form alcohols.
Type:
Grant
Filed:
February 22, 2001
Date of Patent:
June 11, 2002
Assignee:
Oxeno Olefinchemie GmbH
Inventors:
Alfred Kaizik, Walter Toetsch, Wilfried Bueschken, Felix Gosmann
Abstract: Carboxylic esters are prepared by a process, which comprises reacting dicarboxylic or polycarboxylic acids or their anhydrides with alcohols in a liquid medium with the concomitant removal of water formed by the esterification reaction by azeotropic distillation together with the alcohol in the medium, wherein the amount of liquid removed from the reaction medium by azeotropic distillation is replaced in whole or in part with the alcohol.
Abstract: Alkyl tert-alkyl ethers are cleaved into the corresponding isoolefins and alkanols by a process comprising acid-catalyzed reactive distilling an alkyl tert-alkyl ether fed into the reaction zone of a reactive distillation apparatus as an azeotrope of the alkyl tert-alkyl ether and the corresponding alkanol, wherein the reactive distillation apparatus is configured from bottom to top as a bottom zone, at least one distillation zone and a reaction zone.
Type:
Application
Filed:
April 25, 2001
Publication date:
January 24, 2002
Applicant:
OXENO Olefinchemie GmbH
Inventors:
Michael Sakuth, Axel Tuchlenski, Dieter Reusch, Andreas Beckmann
Abstract: The invention relates to a process for the catalytic aldol condensation of aldehydes by means of a multiphase reaction in a tube reactor, wherein the catalyst is present in the continuous phase and at least one aldehyde is present in a dispersed phase and the loading factor B of the tube reactor is equal to or greater than 0.8; the aldol condensation products obtained in this way can be used for preparing alcohols or carboxylic acids.
Abstract: A process for preparing higher oxo alcohols from mixtures of isomeric olefins having from 5 to 24 carbon atoms by two-stage hydroformylation in the presence of a cobalt catalyst or rhodium catalyst at elevated temperature and at elevated pressure, which comprises selectively hydrogenating the first hydroformylation stage reaction mixture, separating the hydrogenation mixture in a distillation into crude alcohol and low-boilers predominantly consisting of olefins, passing these low-boilers to the second hydroformylation stage, again selectively hydrogenating the second hydroformylation stage reaction mixture, separating the hydrogenation mixture in one distillation into crude alcohol and low-boilers, working up the crude alcohol by distillation to pure alcohol and taking off at least some of the low-boilers to discharge saturated hydrocarbons.
Type:
Grant
Filed:
September 15, 1999
Date of Patent:
December 18, 2001
Assignee:
Oxeno Olefinchemie GmbH
Inventors:
Alfred Kaizik, Bernhard Scholz, Walter Toetsch, Wilfried Bueschken, Franz Nierlich
Abstract: A nickel-containing hydrogenation catalyst is prepared by reducing nickel-containing catalyst material in the liquid phase in a single-stage process by means of hydrogen.
Type:
Grant
Filed:
July 17, 2000
Date of Patent:
October 16, 2001
Assignee:
Oxeno Olefinchemie GmbH
Inventors:
Bernhard Scholz, Alfred Kaizik, Wilfried Büschken
Abstract: The present invention is a process for preparing C4-25 aldehydes by hydroformylating the corresponding C3-24 olefins in the presence of a cobalt hydroformylation catalyst, and catalytically decomposing the formic acid formed in the hydroformylation reaction or in the subsequent catalyst work-up. The aldehydes so produced may be hydrogenated to form alcohols.
Type:
Application
Filed:
February 22, 2001
Publication date:
September 20, 2001
Applicant:
OXENO Olefinchemie GmbH
Inventors:
Alfred Kaizik, Walter Toetsch, Wilfried Bueschken, Felix Gosmann
Abstract: A process for the synthesis of vinyl esters from butene oligomers, wherein butenes are oligomerized, the butene oligomers are separated from the oligomerized mixture, the butene oligomers are converted to carboxylic acids which are longer by one carbon atom, and the resulting carboxylic acids are converted to the corresponding vinyl esters. The butene oligomers are in particular dibutene, tributene and tetrabutene. The invention also relates to the use of the vinyl esters as plasticizers or as comonomers in polymerization reactions.
Type:
Grant
Filed:
February 28, 2000
Date of Patent:
August 28, 2001
Assignee:
OXENO Olefinchemie GmbH
Inventors:
Klaus-Diether Wiese, Paul Olbrich, Juergen Gabriel