JPH0346461B2 - - Google Patents
Info
- Publication number
- JPH0346461B2 JPH0346461B2 JP5049887A JP5049887A JPH0346461B2 JP H0346461 B2 JPH0346461 B2 JP H0346461B2 JP 5049887 A JP5049887 A JP 5049887A JP 5049887 A JP5049887 A JP 5049887A JP H0346461 B2 JPH0346461 B2 JP H0346461B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- producing
- secondary amine
- fatty acid
- methyl
- 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.)
- Expired
Links
- -1 secondary amine compound Chemical class 0.000 claims description 16
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 15
- 239000000194 fatty acid Substances 0.000 claims description 15
- 229930195729 fatty acid Natural products 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 150000004665 fatty acids Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 230000001476 alcoholic effect Effects 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 150000003334 secondary amides Chemical class 0.000 claims description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 150000003335 secondary amines Chemical class 0.000 description 8
- 239000000843 powder Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 5
- 150000001414 amino alcohols Chemical class 0.000 description 5
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 4
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000009435 amidation Effects 0.000 description 2
- 238000007112 amidation reaction Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- XIRNKXNNONJFQO-UHFFFAOYSA-N ethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC XIRNKXNNONJFQO-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- KDQIFKKWPMBNOH-UHFFFAOYSA-N methyl 16-methylheptadecanoate Chemical compound COC(=O)CCCCCCCCCCCCCCC(C)C KDQIFKKWPMBNOH-UHFFFAOYSA-N 0.000 description 2
- QSQLTHHMFHEFIY-UHFFFAOYSA-N methyl behenate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OC QSQLTHHMFHEFIY-UHFFFAOYSA-N 0.000 description 2
- YRHYCMZPEVDGFQ-UHFFFAOYSA-N methyl decanoate Chemical compound CCCCCCCCCC(=O)OC YRHYCMZPEVDGFQ-UHFFFAOYSA-N 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- ZAZKJZBWRNNLDS-UHFFFAOYSA-N methyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC ZAZKJZBWRNNLDS-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 2
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 description 1
- NLMDJJTUQPXZFG-UHFFFAOYSA-N 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane Chemical compound C1COCCOCCNCCOCCOCCN1 NLMDJJTUQPXZFG-UHFFFAOYSA-N 0.000 description 1
- NQLIIKFWBDSAQK-UHFFFAOYSA-N 1-hexadecoxy-3-(2-hydroxyethylamino)propan-2-ol Chemical compound CCCCCCCCCCCCCCCCOCC(O)CNCCO NQLIIKFWBDSAQK-UHFFFAOYSA-N 0.000 description 1
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 1
- DVWSXZIHSUZZKJ-UHFFFAOYSA-N 18:3n-3 Natural products CCC=CCC=CCC=CCCCCCCCC(=O)OC DVWSXZIHSUZZKJ-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 description 1
- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940067592 ethyl palmitate Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- LUDJEXSMUHCBGQ-UHFFFAOYSA-N methyl 2-heptylundec-2-enoate Chemical compound CCCCCCCCC=C(CCCCCCC)C(=O)OC LUDJEXSMUHCBGQ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DVWSXZIHSUZZKJ-YSTUJMKBSA-N methyl linolenate Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OC DVWSXZIHSUZZKJ-YSTUJMKBSA-N 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PUGFCQQOYJMKOO-UHFFFAOYSA-N n-(3-hexadecoxy-2-hydroxypropyl)-n-(2-hydroxyethyl)hexadecanamide Chemical compound CCCCCCCCCCCCCCCCOCC(O)CN(CCO)C(=O)CCCCCCCCCCCCCCC PUGFCQQOYJMKOO-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5049887A JPS63216852A (ja) | 1987-03-05 | 1987-03-05 | ２級アミド誘導体の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5049887A JPS63216852A (ja) | 1987-03-05 | 1987-03-05 | ２級アミド誘導体の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63216852A JPS63216852A (ja) | 1988-09-09 |
| JPH0346461B2 true JPH0346461B2 (enrdf_load_stackoverflow) | 1991-07-16 |
Family
ID=12860605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5049887A Granted JPS63216852A (ja) | 1987-03-05 | 1987-03-05 | ２級アミド誘導体の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63216852A (enrdf_load_stackoverflow) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE109767T1 (de) * | 1989-05-19 | 1994-08-15 | Kao Corp | Amidderivate und sie enthaltende hautpräparationen. |
| US5221757A (en) * | 1989-05-19 | 1993-06-22 | Kao Corporation | Amide derivatives and dermatologic preparations containing the same |
| JPH06145123A (ja) * | 1992-11-02 | 1994-05-24 | Kao Corp | アミド誘導体及びその製造中間体、並びに該アミド誘導体を含有する皮膚外用剤 |
| WO1995007882A1 (en) * | 1993-09-14 | 1995-03-23 | The Procter & Gamble Company | Synthesis of amido acids from carboxylic acid esters and amino acid salts |
| CA2171710A1 (en) * | 1993-09-14 | 1995-03-23 | Stephen Wayne Heinzman | Synthesis of sarcosinate surfactants |
| JP4101320B2 (ja) * | 1996-10-11 | 2008-06-18 | 高砂香料工業株式会社 | 一級アミド誘導体の製造方法 |
| TWI238068B (en) | 2001-03-06 | 2005-08-21 | Kao Corp | Composition for external application |
| JP5575718B2 (ja) * | 2011-09-13 | 2014-08-20 | 花王株式会社 | Ｎ−アシルアミノトリオールの製造法 |
| JP6235844B2 (ja) | 2012-09-20 | 2017-11-22 | 花王株式会社 | 皮膚又は毛髪用洗浄剤組成物 |
| JP6040079B2 (ja) * | 2013-03-28 | 2016-12-07 | 花王株式会社 | アミド誘導体の製造方法 |
-
1987
- 1987-03-05 JP JP5049887A patent/JPS63216852A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63216852A (ja) | 1988-09-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0346461B2 (enrdf_load_stackoverflow) | ||
| JP4377594B2 (ja) | β−アルコキシプロピオンアミド類の製造方法 | |
| EP0510625B1 (en) | Process for preparing hindered amine light stabilizers | |
| KR100190784B1 (ko) | 유기 에스테르 및 아미드의 제조방법 및 이를 위한 촉매계 | |
| JPS5826849A (ja) | メタクリル−及びアクリルアミドの製造法 | |
| EP0486715B1 (en) | Aminoacetal derivatives | |
| JP2976245B2 (ja) | ヒドロキシフェニルプロピオン酸エステルの製造方法 | |
| US4104477A (en) | Ester derivatives | |
| JP2604672B2 (ja) | アミド誘導体の製造方法 | |
| JP2659407B2 (ja) | 新規ロジウム錯体、その製造法および新規ロジウム錯体を使用した不斉アルコールの製造方法 | |
| JP4250211B2 (ja) | 新規なアミノカルボン酸エステル塩誘導体 | |
| JP2001181271A (ja) | α−モノグリセリドケタールの製造法 | |
| JPS63154643A (ja) | 低級カルボン酸エステルの製法 | |
| JP4663105B2 (ja) | ２−スルホニル−４−オキシピリジン誘導体の製造方法 | |
| JP3777407B2 (ja) | カルボン酸誘導体の製造法 | |
| JPH021447A (ja) | アジドーカルボン酸エステルの製造方法 | |
| JP2531660B2 (ja) | ビス（２，２，６，６−テトラメチル−４−ピペリジル）セバケ−トの精製法 | |
| JPH10306053A (ja) | エステルの製造方法 | |
| JPH0158175B2 (enrdf_load_stackoverflow) | ||
| JP4266230B2 (ja) | 新規なアミノカルボン酸エステル塩誘導体 | |
| JPH0372054B2 (enrdf_load_stackoverflow) | ||
| JPS63295531A (ja) | β−（３，５−ジアルキル−４−ヒドロキシフェニル）プロピオン酸アルキルエステルの製造方法 | |
| EP0357428A1 (en) | Process for preparing Beta-hydroxy fatty acid | |
| JP2876531B1 (ja) | １，８−ビス（置換エチル）ナフタレン化合物及びその製造方法 | |
| KR100445781B1 (ko) | (ｓ)-1-아세틸-2-피롤리딘카복스아미드의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |