Compound comprising certain level of bio-based carbon

Patent metadata

Field	Value
Publication number	US-11142494-B2
Application number	US-201716311162-A
Country	US
Kind code	B2
Filing date	Jun 19, 2017
Priority date	Jun 20, 2016
Publication date	Oct 12, 2021
Grant date	Oct 12, 2021

Abstract

The present invention relates to a compound according to Formula (3), wherein the compound comprises from 28 wt. % to 100 wt. % bio-based carbon content, relative to the total mass of carbon in the compound, measured according to standard ASTM D6866-12, Method B;and wherein X+is a proton. The present invention also relates to a polymer obtained by polymerising at least one of compound according to Formula (3), in addition to processes and uses related thereto.

First claim

What is claimed is:

1. A compound according to Formula (3), wherein the compound comprises from 28 wt. % to 100 wt. %, bio-based carbon content, relative to the total mass of carbon in the compound, according to standard ASTM D6866-12, Method B, calculated by multiplying the percent modern carbon value, as determined by measuring the carbon-14 content relative to the total carbon content, by a correction factor of 0.95;

and wherein X + is a proton.

2. A compound, according to Formula (3), derived from isobutene, wherein the isobutene has at least 90 wt. % bio-based carbon content, relative to the total mass of carbon in isobutene, according to standard ASTM D6866-12, Method B, calculated by multiplying the percent modern carbon value, as determined by measuring the carbon-14 content relative to the total carbon content, by a correction factor of 0.95;

and wherein X + is a proton.

3. A compound, according to Formula (3), derived from acrylonitrile, wherein the acrylonitrile has at least 90 wt. % bio-based carbon content, relative to the total mass of carbon in acrylonitrile, according to standard ASTM D6866-12, Method B, calculated by multiplying the percent modern carbon value, as determined by measuring the carbon-14 content relative to the total carbon content, by a correction factor of 0.95;

and wherein X + is a proton.

4. The compound according to claim 1 , wherein the compound is derived from both isobutene and acrylonitrile, wherein the isobutene has at least 90 wt. % bio-based carbon content, relative to the total mass of carbon in isobutene, measured according to standard ASTM D6866-12, Method B, calculated by multiplying the percent modern carbon value, as determined by measuring the carbon-14 content relative to the total carbon content, by a correction factor of 0.95; and wherein the acrylonitrile has at least 90 wt. % bio-based carbon content, relative to the total mass of carbon in acrylonitrile, measured according to standard ASTM D6866-12, Method B.

5. A polymer prepared by polymerising at least one compound according to Formula (3), wherein the at least one compound according to Formula (3) comprises from 28 wt. % to 100 wt. %, bio-based carbon content, relative to the total mass of carbon in the compound, according to standard ASTM D6866-12, Method B, calculated by multiplying the percent modern carbon value, as determined by measuring the carbon-14 content relative to the total carbon content, by a correction factor of 0.95;

and wherein X + is a proton.

6. A polymer according to claim 5 , wherein the polymer comprises at least one repeating unit according to Formula (1),

wherein R 1 and R 2 are H; A is —C(CH 3 ) 2 —H 2 C—; and Q+ is cation.

7. The polymer according to claim 5 , wherein the polymer has a weight average molecular weight of at least 700 g/mol.

8. The polymer according to claim 5 , wherein the polymer is a homopolymer.

9. A process for synthesizing a compound according to Formula (3), comprising reacting acrylonitrile, fuming sulfuric acid and isobutene in a solvent; wherein the isobutene has at least 90 wt. % bio-based carbon content, relative to the total mass of carbon in isobutene, measured according to standard ASTM D6866-12, Method B, calculated by multiplying the percent modern carbon value, as determined by measuring the carbon-14 content relative to the total carbon content, by a correction factor of 0.95;
and/or wherein the acrylonitrile has at least 90 wt. % bio-based carbon content, relative to the total mass of carbon in acrylonitrile, measured according to standard ASTM D6866-12, Method B, calculated by multiplying the percent modern carbon value, as determined by measuring the carbon-14 content relative to the total carbon content, by a correction factor of 0.95;

and wherein X + is a proton.

10. The process according to claim 9 , comprising:
(a) a first step of mixing fuming sulfuric acid with the acrylonitrile to produce a mixture of acrylonitrile and fuming sulfuric acid in an aprotic polar solvent;
(b) a second step of contacting the mixture produced in the first step, with the isobutene, to obtain an aprotic polar solvent slurry of compound according to Formula (3)

wherein X + is a proton;
(c) optionally a third step of subjecting the slurry obtained in the second step, to solid-liquid separation to obtain a cake of crude compound according to Formula (3), and then washing the cake with an aprotic polar solvent of mass of at least two times that of the cake, and
(d) optionally a fourth step of drying the cake washed in the third step.

11. The process according to claim 10 , wherein the first step is carried out at a temperature of from −50° C. to 10° C.

12. The process according to claim 10 , wherein the second step is carried out at a temperature of from 10° C. to 70° C.

13. The process according to claim 9 , further comprising isolating a compound according to Formula (3);

wherein X + is a proton; and then optionally employing said compound to synthesize a polymer.

14. A polymer according to claim 5 , wherein the at least one compound according to Formula (3) is derived from isobutene, wherein the isobutene has at least 90 wt. % bio-based carbon content, relative to the total mass of carbon in isobutene, according to standard ASTM D6866-12, Method B, calculated by multiplying the percent modern carbon value, as determined by measuring the carbon-14 content relative to the total carbon content, by a correction factor of 0.95.

15. A polymer according to claim 5 , wherein the at least one compound according to Formula (3) is derived from acrylonitrile, wherein the acrylonitrile has at least 90 wt. % bio-based carbon content, relative to the total mass of carbon in acrylonitrile, according to standard ASTM D6866-12, Method B, calculated by multiplying the percent modern carbon value, as determined by measuring the carbon-14 content relative to the total carbon content, by a correction factor of 0.95.

16. A polymer according to claim 5 , wherein the at least one compound according to Formula (3) is derived from both isobutene and acrylonitrile, wherein the isobutene has at least 90 wt. % bio-based carbon content, relative to the total mass of carbon in isobutene, measured according to standard ASTM D6866-12, Method B, calculated by multiplying the percent modern carbon value, as determined by measuring the carbon-14 content relative to the total carbon content, by a correction factor of 0.95; and wherein the acrylonitrile has at least 90 wt. % bio-based carbon content, relative to the total mass of carbon in acrylonitrile, measured according to standard ASTM D6866-12, Method B, calculated by multiplying the percent modern carbon value, as determined by measurin

Assignees

• Clariant Int Ltd

Inventors

• Kayser Christoph
• Starkulla Gundula
• Fischer Dirk
• Kaufmann Paul
• Schäfer Michael
• Götz Katharina

Classifications

• C07C303/44

  Separation; Purification · CPC title

• C07C303/06

  by reaction with sulfuric acid or sulfur trioxide · CPC title

• C08F20/58

  containing oxygen in addition to the carbonamido oxygen {, e.g. N-methylolacrylamide, N-acryloylmorpholine} · CPC title

• C07C309/15 Primary

  the nitrogen atom of at least one of the amino groups being part of any of the groups [IMAGE cpc-sch-C07C-0975.gif], X being a hetero atom, Y being any atom · CPC title

• C08F10/00

  Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond · CPC title