Long alpha-omega di-functional linear ethers

Patent metadata

Field	Value
Publication number	US-11634376-B2
Application number	US-201916979976-A
Country	US
Kind code	B2
Filing date	Mar 14, 2019
Priority date	Mar 14, 2018
Publication date	Apr 25, 2023
Grant date	Apr 25, 2023

Abstract

The current invention relates to long α-ω di-functional linear molecules as building blocks closing the gap between small molecules and polymers, or in a polycondensated form, in the production of oligomers and/or polymers, surfactants, lubricants, coatings, colloidal stabilizing surface chains/molecules.

First claim

The invention claimed is:

1. A compound of Formula I,
R 1 -L 1 -O-L 1 -R 2   (I)

wherein
L 1 is C 8 -alkyl;
R 1 and R 2 are each independently selected from —(CH 2 ) m OH, —(CH 2 ) n COOH, and —(CH 2 ) p NH 2 ;
each occurrence of m is independently an integer from 5 to 9;
each occurrence of n is independently an integer from 3 to 8;
each occurrence of p is independently an integer from 5 to 9; and
the compound is not HOOC—(CH 2 ) 15 —O—(CH 2 ) 16 —OH.

2. The compound of claim 1 , wherein
L 1 is C 8 -alkyl;
R 1 and R 2 are both selected from either —(CH 2 ) m OH, or both —(CH 2 ) n COOH, or both —(CH 2 ) p NH 2 ;
each occurrence of m is independently an integer from 5 to 9;
each occurrence of n is independently an integer from 3 to 8;
each occurrence of p is independently an integer from 1 to 9; preferably from 5 to 9.

3. The compound of claim 1 , wherein
L 1 is C 8 -alkyl;
R 1 and R 2 are both —(CH 2 ) m OH, or both —(CH 2 ) n COOH, or both —(CH 2 ) p NH 2 ;
m is an integer from 5 to 9;
n is an integer from 3 to 8;
p is an integer from 5 to 9; and
R 1 and R 2 are equal to each other.

4. The compound claim 1 , selected from the group consisting of:

wherein each x is an identical integer from 13 to 17;

wherein each y is an identical integer from 11 to 16; and

wherein each z is an identical integer from 13 to 17.

5. A composition comprising a compound according to claim 1 .

6. The compound of claim 1 , wherein R 1 and R 2 are each independently selected from —(CH 2 ) n COOH and —(CH 2 ) p NH 2 .

7. The compound claim 1 , selected from the group consisting of:

wherein each y is an identical integer from 11 to 16; and

wherein each z is an identical integer from 13 to 17.

8. The compound of claim 1 , wherein R 1 and R 2 are each —(CH 2 ) n COOH.

9. The compound claim 1 , selected from the group consisting of:

wherein each y is an identical integer from 11 to 16.

10. The compound of claim 1 , having a melting point of at least 70° C.

11. A method for the preparation of a compound of formula (II)
R 3 -L 3 -O-L 4 -R 4   (II)

wherein
L 3 and L 4 are alkyl chains comprising at least 8 C atoms;
R 3 and R 4 are each independently selected from —OH, —COOH, —NH 2 ;
the total number of C atoms in L 3 and R 3 together is at most 17; and
the total number of C atoms in L 4 and R 4 together is at most 17, the method comprising:
providing a first solution comprising at least one monounsaturated alcohol, dialkyl carbonate and a heterogeneous oxide based catalyst;
heating the first solution;
removing the catalyst and non-reacted dialkyl carbonate from the first solution, resulting in a second solution;
adding a heterogeneous oxide based catalyst to the second solution, resulting in a third solution;
heating the third solution to obtain an unsaturated dialkyl ether compound;
cleaving the unsaturated bond of the unsaturated dialkyl ether to obtain functionalized end groups; and
optionally further derivatizing the obtained functionalized end groups.

12. The method according to claim 11 , wherein the heterogeneous oxide based catalyst is a heterogeneous silicon/aluminum oxide based catalyst.

13. The method according to claim 11 wherein the heterogeneous oxide based catalyst is hydrotalcite.

14. The method according to claim 11 wherein the dialkyl carbonate is selected from the group consisting of dimethylcarbonate and diethylcarbonate.

15. The method according to claim 11 wherein cleaving the unsaturated bond comprises performing ozonolysis.

16. The method according to claim 15 , wherein the ozonolysis is performed under oxidative or reductive conditions.

17. The method according to claim 11 wherein cleaving the unsaturated bond comprises oxidizing the double bond resulting in a vicinal diol group wherein the vicinal diol group is oxidatively cleaved again.

18. The method according to claim 11 , comprising further derivatizing the obtained functional end groups by oxidizing and/or reducing and/or converting an alcohol group to an amine group.

19. The method according to claim 11 , wherein the compound of formula (II) is selected from the group consisting of

wherein each x is an identical integer from 13 to 17;

wherein each y is an identical integer from 11 to 16; and

wherein each z is an identical integer from 13 to 17.

Assignees

• Univ Antwerpen

Inventors

• Pazdur Lukasz
• Tavernier Serge M F

Classifications

• C07C45/40

  by oxidation with ozone; by ozonolysis · CPC title

• C07C59/305

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• C07C43/132

  both carbon chains being substituted by hydroxy or O-metal groups · CPC title

• C07C51/285

  with peroxy-compounds · CPC title

• C07C51/245

  of keto groups or secondary alcohol groups · CPC title