JP2009541417A5 - - Google Patents
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- Publication number
- JP2009541417A5 JP2009541417A5 JP2009517122A JP2009517122A JP2009541417A5 JP 2009541417 A5 JP2009541417 A5 JP 2009541417A5 JP 2009517122 A JP2009517122 A JP 2009517122A JP 2009517122 A JP2009517122 A JP 2009517122A JP 2009541417 A5 JP2009541417 A5 JP 2009541417A5
- Authority
- JP
- Japan
- Prior art keywords
- amide
- reaction
- alcohol
- oxidant
- cocatalyst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000007800 oxidant agent Substances 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 150000001408 amides Chemical class 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 20
- 230000001590 oxidative effect Effects 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 125000003368 amide group Chemical group 0.000 claims description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 6
- 150000008045 alkali metal halides Chemical group 0.000 claims description 6
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 claims description 5
- UXBLSWOMIHTQPH-UHFFFAOYSA-N 4-acetamido-TEMPO Chemical compound CC(=O)NC1CC(C)(C)N([O])C(C)(C)C1 UXBLSWOMIHTQPH-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000002585 base Substances 0.000 claims 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims 2
- ISAOUZVKYLHALD-UHFFFAOYSA-N 1-chloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)NC(=O)NC1=O ISAOUZVKYLHALD-UHFFFAOYSA-N 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229940098691 coco monoethanolamide Drugs 0.000 claims 1
- 239000013029 homogenous suspension Substances 0.000 claims 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910019093 NaOCl Inorganic materials 0.000 description 24
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 24
- -1 amide carboxylic acids Chemical class 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 10
- 229940065856 cocoyl glycinate Drugs 0.000 description 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 8
- 239000007791 liquid phase Substances 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 6
- JWGGSJFIGIGFSQ-UHFFFAOYSA-N N-dodecanoylglycine Chemical compound CCCCCCCCCCCC(=O)NCC(O)=O JWGGSJFIGIGFSQ-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 150000003138 primary alcohols Chemical class 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- 239000007844 bleaching agent Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 241000282320 Panthera leo Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FMRWQLAJBBKXDM-UHFFFAOYSA-N 2,2,5,5-tetramethylpyrrolidine Chemical compound CC1(C)CCC(C)(C)N1 FMRWQLAJBBKXDM-UHFFFAOYSA-N 0.000 description 1
- VCSBYMNXXXLPNA-UHFFFAOYSA-N 2,2,7,7-tetramethylazepane Chemical compound CC1(C)CCCCC(C)(C)N1 VCSBYMNXXXLPNA-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QZXSMBBFBXPQHI-UHFFFAOYSA-N N-(dodecanoyl)ethanolamine Chemical compound CCCCCCCCCCCC(=O)NCCO QZXSMBBFBXPQHI-UHFFFAOYSA-N 0.000 description 1
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001513 alkali metal bromide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001616 alkaline earth metal bromide Inorganic materials 0.000 description 1
- 229910001617 alkaline earth metal chloride Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910001622 calcium bromide Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
- 238000000105 evaporative light scattering detection Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- NABGJEMOSRZQSY-UHFFFAOYSA-N n-oxaldehydoyldodecanamide Chemical compound CCCCCCCCCCCC(=O)NC(=O)C=O NABGJEMOSRZQSY-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical group O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003140 primary amides Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/475,824 US20070299269A1 (en) | 2006-06-27 | 2006-06-27 | Process for converting primary amidoalcohols to amidocarboxylic acids in high yield |
| US11/475,824 | 2006-06-27 | ||
| PCT/EP2007/056140 WO2008000671A1 (en) | 2006-06-27 | 2007-06-20 | Process for converting primary amidoalcohols to amidocarboxylic acids in high yield using water as solvent |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015087360A Division JP2015180629A (ja) | 2006-06-27 | 2015-04-22 | 水を溶媒として使用して、第一級アミドアルコールを高収率でアミドカルボン酸へ変換する方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009541417A JP2009541417A (ja) | 2009-11-26 |
| JP2009541417A5 true JP2009541417A5 (enExample) | 2015-06-18 |
| JP5886515B2 JP5886515B2 (ja) | 2016-03-16 |
Family
ID=38474353
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009517122A Expired - Fee Related JP5886515B2 (ja) | 2006-06-27 | 2007-06-20 | 水を溶媒として使用して、第一級アミドアルコールを高収率でアミドカルボン酸へ変換する方法 |
| JP2015087360A Pending JP2015180629A (ja) | 2006-06-27 | 2015-04-22 | 水を溶媒として使用して、第一級アミドアルコールを高収率でアミドカルボン酸へ変換する方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015087360A Pending JP2015180629A (ja) | 2006-06-27 | 2015-04-22 | 水を溶媒として使用して、第一級アミドアルコールを高収率でアミドカルボン酸へ変換する方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US20070299269A1 (enExample) |
| EP (1) | EP2044003B1 (enExample) |
| JP (2) | JP5886515B2 (enExample) |
| KR (1) | KR20090021363A (enExample) |
| CN (1) | CN101479234B (enExample) |
| AU (1) | AU2007263835B2 (enExample) |
| BR (1) | BRPI0712647B1 (enExample) |
| ES (1) | ES2393519T3 (enExample) |
| MX (1) | MX2008016346A (enExample) |
| PL (1) | PL2044003T3 (enExample) |
| RU (1) | RU2453534C2 (enExample) |
| WO (1) | WO2008000671A1 (enExample) |
| ZA (1) | ZA200810837B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006038853A1 (de) | 2006-08-18 | 2008-02-21 | Clariant International Limited | Verfahren zur Herstellung von Acylglycinaten mittels Direktoxidation |
| DE102007055265A1 (de) | 2007-11-20 | 2009-05-28 | Clariant International Ltd. | Verfahren zur Herstellung von Acylglycinaten |
| DE102008003825A1 (de) | 2008-01-10 | 2009-07-16 | Clariant International Ltd. | Verfahren zur Herstellung von Acylglycinaten mittels Direktoxidation |
| EP2697202B1 (en) | 2011-04-13 | 2015-07-22 | Rennovia, Inc. | Production of caprolactam from carbohydrate-containing materials |
| DE102011107503A1 (de) * | 2011-07-15 | 2012-03-01 | Clariant International Ltd. | Verfahren zur Herstellung von Acylglycinaten und Zusammensetzungen enthaltend derartige Verbindungen |
| US8658589B2 (en) | 2011-07-28 | 2014-02-25 | Conopco, Inc. | Fatty acyl amido based surfactant concentrates |
| US8853447B2 (en) | 2011-07-28 | 2014-10-07 | Conopco, Inc. | General method for preparing fatty acyl amido based surfactants |
| US8853433B2 (en) | 2011-07-28 | 2014-10-07 | Conopco, Inc. | General method for preparing fatty acyl amido based surfactants |
| US8697897B2 (en) | 2011-07-28 | 2014-04-15 | Conopco, Inc. | Method for preparing fatty acyl amido carboxylic acid based surfactants |
| US8653018B2 (en) | 2011-07-28 | 2014-02-18 | Conopco, Inc. | Fatty acyl amido based surfactant concentrates |
| US8822711B2 (en) | 2011-07-28 | 2014-09-02 | Conopco, Inc. | Method for preparing fatty acyl amido carboxylic acid based surfactants |
| US8981134B2 (en) | 2011-07-28 | 2015-03-17 | Conopco, Inc. | Amino acid salt containing compositions |
| CN108430624A (zh) * | 2015-12-18 | 2018-08-21 | 株式会社Acenet | 自由基产生催化剂、自由基的制造方法、氧化反应产物的制造方法、药剂及农业畜牧业用药剂 |
| CN105503637A (zh) * | 2016-01-22 | 2016-04-20 | 江南大学 | 一种合成脂肪酰基甘氨酸的方法 |
| US10618867B2 (en) | 2016-06-29 | 2020-04-14 | Evonik Operations Gmbh | Method for producing surfactants |
| CN115872859A (zh) * | 2021-09-28 | 2023-03-31 | 佳化化学(上海)有限公司 | 一种醇醚羧酸的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4016287A (en) * | 1972-07-17 | 1977-04-05 | Boehringer Ingelheim Gmbh | Dermatological compositions containing an acylamino-carboxylic acid or an alkyl ester thereof |
| US5175360A (en) * | 1990-11-26 | 1992-12-29 | Shell Oil Company | Preparation of alkoxyalkanoic acids |
| US5506224A (en) * | 1991-12-31 | 1996-04-09 | Lifegroup S.P.A. | N-acyl derivatives of aminoalcohols active as local autacoids and useful in the therapy of autoimmune processes |
| US5488154A (en) * | 1994-10-13 | 1996-01-30 | Shell Oil Company | Process for the preparation of alkoxyalkanoic acids |
| US5646319A (en) * | 1995-06-23 | 1997-07-08 | The Procter & Gamble Company | Synthesis of N-acyl-N-alkylcarboxylates |
| JPH09151169A (ja) * | 1995-12-01 | 1997-06-10 | Kao Corp | アミドエーテルカルボン酸又はその塩の製造方法 |
| JPH1087554A (ja) * | 1996-09-12 | 1998-04-07 | Lion Corp | アミドカルボン酸またはアルコキシカルボン酸およびそれらの塩の製造方法 |
| DE69720494T2 (de) * | 1996-09-13 | 2004-02-05 | Nippon Kayaku K.K. | Optisch aktive erythro-3-amino-2-hydroxy-buttersäureester und verfahren zur herstellung der genannten ester |
| JPH10130195A (ja) * | 1996-11-01 | 1998-05-19 | Lion Corp | カルボン酸およびその塩の製造方法 |
| JP4407846B2 (ja) * | 1998-02-27 | 2010-02-03 | 花王株式会社 | １級アルコールの酸化方法 |
| JP2003221371A (ja) * | 2001-11-26 | 2003-08-05 | Ajinomoto Co Inc | Ｎ−長鎖アシル中性アミノ酸の製造方法 |
-
2006
- 2006-06-27 US US11/475,824 patent/US20070299269A1/en not_active Abandoned
-
2007
- 2007-05-24 US US11/753,096 patent/US7439388B2/en not_active Expired - Fee Related
- 2007-06-20 WO PCT/EP2007/056140 patent/WO2008000671A1/en not_active Ceased
- 2007-06-20 JP JP2009517122A patent/JP5886515B2/ja not_active Expired - Fee Related
- 2007-06-20 ES ES07730270T patent/ES2393519T3/es active Active
- 2007-06-20 CN CN200780023935XA patent/CN101479234B/zh not_active Expired - Fee Related
- 2007-06-20 KR KR1020087031592A patent/KR20090021363A/ko not_active Withdrawn
- 2007-06-20 ZA ZA200810837A patent/ZA200810837B/xx unknown
- 2007-06-20 BR BRPI0712647A patent/BRPI0712647B1/pt not_active IP Right Cessation
- 2007-06-20 MX MX2008016346A patent/MX2008016346A/es active IP Right Grant
- 2007-06-20 RU RU2009102502/04A patent/RU2453534C2/ru not_active IP Right Cessation
- 2007-06-20 AU AU2007263835A patent/AU2007263835B2/en not_active Ceased
- 2007-06-20 PL PL07730270T patent/PL2044003T3/pl unknown
- 2007-06-20 EP EP07730270A patent/EP2044003B1/en not_active Not-in-force
-
2015
- 2015-04-22 JP JP2015087360A patent/JP2015180629A/ja active Pending
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