MX2016005015A - Sintesis de diacidos, dialdehidos o diaminas a partir de thf-dioles. - Google Patents
Sintesis de diacidos, dialdehidos o diaminas a partir de thf-dioles.Info
- Publication number
- MX2016005015A MX2016005015A MX2016005015A MX2016005015A MX2016005015A MX 2016005015 A MX2016005015 A MX 2016005015A MX 2016005015 A MX2016005015 A MX 2016005015A MX 2016005015 A MX2016005015 A MX 2016005015A MX 2016005015 A MX2016005015 A MX 2016005015A
- Authority
- MX
- Mexico
- Prior art keywords
- thf
- bis
- dinitrile
- sulfonate
- tetrahydrofuran
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 150000004985 diamines Chemical class 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 3
- PAIRTZWGOWLBHO-UHFFFAOYSA-N [5-(sulfomethyl)oxolan-2-yl]methanesulfonic acid Chemical compound C1(CCC(CS(=O)(=O)O)O1)CS(=O)(=O)O PAIRTZWGOWLBHO-UHFFFAOYSA-N 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 abstract 2
- YCZZQSFWHFBKMU-UHFFFAOYSA-N [5-(hydroxymethyl)oxolan-2-yl]methanol Chemical compound OCC1CCC(CO)O1 YCZZQSFWHFBKMU-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000001588 bifunctional effect Effects 0.000 abstract 1
- 238000001311 chemical methods and process Methods 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Se describe un procedimiento químico sencillo y elegante para la síntesis de productos oxigenados, tales como ácidos y aldehídos, u otros productos derivados, tales como aminas y nitrilos, de moléculas bifuncionales cíclicas preparados a partir de fuentes de base biológica renovables tales como HMF y/o su producto de reducción, 2,5-bis(hidroximetil)-tetrahidrofurano (bHMTHF). En general, el procedimiento implica: a) generar un tetrahidrofurano-2,5-diil-bis(metilen)-bis(sulfonato) a partir de bHMTHF utilizando un sulfonato; b) desplazar de manera nucleófila al menos un grupo saliente de sulfonato del tetrahidrofurano-2,5-d iil-bis (metilen)-bis(sulfonato) para formar un THF-dinitrilo; y o bien c) oxidar el THF-dinitrilo con un ácido que tiene un pKa de = 0 para generar un diácido, o bien d) reducir parcialmente el THF-dinitrilo para generar un dialdehído, o bien e) reducir totalmente el THF-dinitrilo para generar una diamina.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361891928P | 2013-10-17 | 2013-10-17 | |
| PCT/US2014/057399 WO2015057365A2 (en) | 2013-10-17 | 2014-09-25 | Synthesis of diacids, dialdehydes, or diamines from thf-diols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2016005015A true MX2016005015A (es) | 2016-06-24 |
Family
ID=52828839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2016005015A MX2016005015A (es) | 2013-10-17 | 2014-09-25 | Sintesis de diacidos, dialdehidos o diaminas a partir de thf-dioles. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20160207894A1 (es) |
| EP (1) | EP3057946A4 (es) |
| JP (1) | JP2016535084A (es) |
| KR (1) | KR20160083865A (es) |
| CN (1) | CN105555773A (es) |
| AU (1) | AU2014334822A1 (es) |
| CA (1) | CA2922405A1 (es) |
| MX (1) | MX2016005015A (es) |
| WO (1) | WO2015057365A2 (es) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2931552A1 (en) * | 2013-12-19 | 2015-06-25 | Archer Daniels Midland Company | Sulfonates of furan-2,5-dimethanol and (tetrahydrofuran-2,5-diyl)dimethanol and derivatives thereof |
| CN106795127A (zh) * | 2014-08-28 | 2017-05-31 | 微麦德斯公司 | 二胺化合物、二硝基化合物和其它化合物及其制备方法和与其相关的用途 |
| WO2017222532A1 (en) * | 2016-06-23 | 2017-12-28 | Archer Daniels Midland Company | Preparation of mono- and di-alkyl halide furanic compounds from 2,5-bis(hydroxymethyl)-tetrahydrofurans (bhmthf) and derivatives thereof |
| CN113248355B (zh) * | 2021-07-07 | 2022-04-26 | 山东国邦药业有限公司 | 一种对氯苯甲醛的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2415261A (en) * | 1944-12-15 | 1947-02-04 | Du Pont | Production of nitriles |
| US3372195A (en) * | 1964-05-04 | 1968-03-05 | Dow Chemical Co | Reduction of nitriles to primary amines |
| US3856783A (en) * | 1973-06-14 | 1974-12-24 | Ici America Inc | 8-oxa-3-azabi cyclo(3.2.1)octane compounds |
| US5124487A (en) * | 1991-08-05 | 1992-06-23 | Occidental Chemical Corporation | Catalytic reduction of nitriles to aldehydes |
| US20090018300A1 (en) * | 2007-07-11 | 2009-01-15 | Archer-Daniels-Midland Company | Monomers and polymers from bioderived carbon |
| CA2992861C (en) * | 2010-12-16 | 2019-03-05 | Archer Daniels Midland Company | Preparation of aminomethyl furan and alkoxymethyl furan derivatives from carbohydrates |
-
2014
- 2014-09-25 MX MX2016005015A patent/MX2016005015A/es unknown
- 2014-09-25 CN CN201480051841.3A patent/CN105555773A/zh active Pending
- 2014-09-25 WO PCT/US2014/057399 patent/WO2015057365A2/en not_active Ceased
- 2014-09-25 AU AU2014334822A patent/AU2014334822A1/en not_active Abandoned
- 2014-09-25 US US14/914,284 patent/US20160207894A1/en not_active Abandoned
- 2014-09-25 KR KR1020167010825A patent/KR20160083865A/ko not_active Withdrawn
- 2014-09-25 JP JP2016549016A patent/JP2016535084A/ja active Pending
- 2014-09-25 CA CA2922405A patent/CA2922405A1/en not_active Abandoned
- 2014-09-25 EP EP14854795.3A patent/EP3057946A4/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP3057946A4 (en) | 2017-03-29 |
| EP3057946A2 (en) | 2016-08-24 |
| AU2014334822A1 (en) | 2016-03-10 |
| CA2922405A1 (en) | 2015-04-23 |
| KR20160083865A (ko) | 2016-07-12 |
| CN105555773A (zh) | 2016-05-04 |
| JP2016535084A (ja) | 2016-11-10 |
| WO2015057365A2 (en) | 2015-04-23 |
| WO2015057365A3 (en) | 2015-06-11 |
| US20160207894A1 (en) | 2016-07-21 |
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