US 9,434,671 B2 · Nitrogen monoxide as cis/trans isomerization catalysts for unsaturated compounds

Abstract

The present invention relates to a process of a cis/trans isomerization of an unsaturated compound A being selected from the group consisting of unsaturated ketones, unsaturated ketals, unsaturated aldehydes, unsaturated acetals, unsaturated carboxylic acids, esters of an unsaturated carboxylic acid and amides of an unsaturated carboxylic acid using nitrogen monoxide as cis/trans isomerization catalyst. It has been observed that the isomerization is very efficient and fast.

Claims17

Dependent claims

A process of a cis/trans isomerization of an unsaturated compound A having at least one but not more than two conjugated carbon-carbon double bonds, the compound A being selected from the group consisting of unsaturated ketones, unsaturated ketals, unsaturated aldehydes, unsaturated acetals, unsaturated carboxylic acids, esters of an unsaturated carboxylic acid, amides of an unsaturated carboxylic acid and unsaturated alcohols, wherein the process comprises the steps of:

a) providing a cis or a trans isomer of the unsaturated compound A;
b) adding nitrogen monoxide to the cis or trans isomer of the unsaturated compound A of step a) to form a mixture thereof;
c) heating the mixture of nitrogen monoxide and cis or trans isomer of the unsaturated compound A to a temperature of between 10° C. and the boiling point of the unsaturated compound A, thereby leading to a mixture of cis/trans isomers of the unsaturated compound A.

A process of producing a respective specific cis or trans isomer of an unsaturated compound A having at least one but not more than two conjugated carbon-carbon double bonds, the compound A being selected from the group consisting of unsaturated ketones, unsaturated ketals, unsaturated aldehydes, unsaturated acetals, unsaturated carboxylic acids, esters of an unsaturated carboxylic acid, amides of an unsaturated carboxylic acid and unsaturated alcohols from a mixture of cis and trans isomers thereof, wherein the process comprises the steps of:

i) providing a mixture of cis isomers in an amount of weight wcis and trans isomers in an amount of weight wtrans of the unsaturated compound A;
ii) adding nitrogen monoxide to the mixture of cis and trans isomers provided by step i);
iii) heating the mixture of the nitrogen monoxide and cis and trans isomers obtained from step ii) to a temperature Tiso1, which is the boiling point of the isomer Ilbp having a lowest boiling point of the mixture of the cis/trans isomers of step i);
iv) distilling off the isomer Ilbp and collecting the isomer Ilbp;
v) conducting cis/trans isomerization of the isomer Ilbp having a higher boiling point than the isomer Ilbp in the presence of nitrogen monoxide being added in step ii);
wherein
step ii) can take place before, during or after steps iii) and/or iv);
and wherein
after the step v), the steps ii) and iii) and iv) and v) are repeated subsequently;
and wherein
a sum of the weight of all the collected isomer Ilbp is either (1) more than the weight wcis in the case the collected isomer Ilbp is a cis isomer of said unsaturated compound A or (2) more than the weight wtrans in the case the collected isomer Ilbp is a trans isomer of the unsaturated compound A;
and wherein
the weight wcis and the weight wtrans are each 0 grams to 10 tons, with the proviso that the ratio of wcis and wtrans is larger than 70/30 or smaller than 30/70 with the proviso that wcis and wtrans are not both 0 grams.

10 more elements

a) providing a mixture of cis isomers in an amount of weight wcis and trans isomers in an amount of weight wtrans of the unsaturated compound A;
b) adding nitrogen monoxide to the mixture of cis and trans isomers provided by step i);
c) heating the mixture of the nitrogen monoxide and cis and trans isomers obtained from step ii) to a temperature Tiso1, which is the boiling point of the isomer Ilbp having a lowest boiling point of the mixture of the cis/trans isomers of step a);
d) distilling off the isomer Ilbp;
e) isolating the specific isomer Ihbp which has a higher boiling point than the isomer Ilbp from a remainder of step d) and collecting the isomer Ihbp;
f) conducting cis/trans isomerization of the isomer Ihbp and a remainder of step e), if any, in the presence of nitrogen monoxide being added in step b);
wherein
step b) can take place before, during or after steps c) and/or f);
and wherein after the step f), the steps b) and c) and d) and e) and f) are repeated subsequently, and wherein
the weight of the collected isomer Ihbp is either (1) more than the weight wcis in the case the collected isomer Ihbp is a cis isomer of the unsaturated compound A or (2) more than the weight wtrans in the case the collected isomer Ihbp is a trans isomer of said unsaturated compound A;
and wherein
the weight wcis and the weight wtrans are each 0 grams to 10 tons, with the proviso that the ratio of wcis and wtrans is larger than 70/30 or smaller than 30/70 with the proviso that wcis and wtrans are not both 0 grams.

9 more elements

Dependencies are inferred from the claim text.

Facts

Application

14/652,286Filed 18 Dec 2013

Priority

EP 1219780318 Dec 2012

Published

US 2015/0321987 A112 Nov 2015

Granted

6 Sep 2016

Term ends

Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07C 43/313
Compounds having [IMAGE cpc-sch-C07C-0958.gif] groups: containing halogen
C07C 29/56
Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring: by isomerisation
C07C 33/02
Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms: acyclic alcohols with carbon-to-carbon double bonds
C07C 45/67
By reactions not involving the formation of >C = O groups: by isomerisation; by change of size of the carbon skeleton

Abstract

Claims17

Dependent claims

a) providing a cis or a trans isomer of the unsaturated compound A;
b) adding nitrogen monoxide to the cis or trans isomer of the unsaturated compound A of step a) to form a mixture thereof;
c) heating the mixture of nitrogen monoxide and cis or trans isomer of the unsaturated compound A to a temperature of between 10° C. and the boiling point of the unsaturated compound A, thereby leading to a mixture of cis/trans isomers of the unsaturated compound A.

i) providing a mixture of cis isomers in an amount of weight wcis and trans isomers in an amount of weight wtrans of the unsaturated compound A;
ii) adding nitrogen monoxide to the mixture of cis and trans isomers provided by step i);
iii) heating the mixture of the nitrogen monoxide and cis and trans isomers obtained from step ii) to a temperature Tiso1, which is the boiling point of the isomer Ilbp having a lowest boiling point of the mixture of the cis/trans isomers of step i);
iv) distilling off the isomer Ilbp and collecting the isomer Ilbp;
v) conducting cis/trans isomerization of the isomer Ilbp having a higher boiling point than the isomer Ilbp in the presence of nitrogen monoxide being added in step ii);
wherein
step ii) can take place before, during or after steps iii) and/or iv);
and wherein
after the step v), the steps ii) and iii) and iv) and v) are repeated subsequently;
and wherein
a sum of the weight of all the collected isomer Ilbp is either (1) more than the weight wcis in the case the collected isomer Ilbp is a cis isomer of said unsaturated compound A or (2) more than the weight wtrans in the case the collected isomer Ilbp is a trans isomer of the unsaturated compound A;
and wherein
the weight wcis and the weight wtrans are each 0 grams to 10 tons, with the proviso that the ratio of wcis and wtrans is larger than 70/30 or smaller than 30/70 with the proviso that wcis and wtrans are not both 0 grams.

10 more elements

a) providing a mixture of cis isomers in an amount of weight wcis and trans isomers in an amount of weight wtrans of the unsaturated compound A;
b) adding nitrogen monoxide to the mixture of cis and trans isomers provided by step i);
c) heating the mixture of the nitrogen monoxide and cis and trans isomers obtained from step ii) to a temperature Tiso1, which is the boiling point of the isomer Ilbp having a lowest boiling point of the mixture of the cis/trans isomers of step a);
d) distilling off the isomer Ilbp;
e) isolating the specific isomer Ihbp which has a higher boiling point than the isomer Ilbp from a remainder of step d) and collecting the isomer Ihbp;
f) conducting cis/trans isomerization of the isomer Ihbp and a remainder of step e), if any, in the presence of nitrogen monoxide being added in step b);
wherein
step b) can take place before, during or after steps c) and/or f);
and wherein after the step f), the steps b) and c) and d) and e) and f) are repeated subsequently, and wherein
the weight of the collected isomer Ihbp is either (1) more than the weight wcis in the case the collected isomer Ihbp is a cis isomer of the unsaturated compound A or (2) more than the weight wtrans in the case the collected isomer Ihbp is a trans isomer of said unsaturated compound A;
and wherein
the weight wcis and the weight wtrans are each 0 grams to 10 tons, with the proviso that the ratio of wcis and wtrans is larger than 70/30 or smaller than 30/70 with the proviso that wcis and wtrans are not both 0 grams.

9 more elements

Dependencies are inferred from the claim text.

Nitrogen monoxide as cis/trans isomerization catalysts for unsaturated compounds

Life of this patent

Abstract

Claims17

Nitrogen monoxide as cis/trans isomerization catalysts for unsaturated compounds

Life of this patent

Abstract

Claims17