CA2766933A1 - Continuous method for acylating amino group-carrying organic acids - Google Patents
Continuous method for acylating amino group-carrying organic acids Download PDFInfo
- Publication number
- CA2766933A1 CA2766933A1 CA2766933A CA2766933A CA2766933A1 CA 2766933 A1 CA2766933 A1 CA 2766933A1 CA 2766933 A CA2766933 A CA 2766933A CA 2766933 A CA2766933 A CA 2766933A CA 2766933 A1 CA2766933 A1 CA 2766933A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- microwave
- reaction
- carbon atoms
- oil
- 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.)
- Abandoned
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- 150000007524 organic acids Chemical class 0.000 title claims abstract description 35
- 235000005985 organic acids Nutrition 0.000 title claims abstract description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title abstract description 5
- 238000011437 continuous method Methods 0.000 title abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 132
- 239000002253 acid Substances 0.000 claims abstract description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 34
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 31
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 17
- 229910052751 metal Inorganic materials 0.000 claims abstract description 10
- 239000002184 metal Substances 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 69
- 230000008569 process Effects 0.000 claims description 69
- 239000011541 reaction mixture Substances 0.000 claims description 66
- -1 alkaline earth metal salt Chemical group 0.000 claims description 56
- 125000003277 amino group Chemical group 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 21
- 239000004020 conductor Substances 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 19
- 150000001408 amides Chemical class 0.000 claims description 18
- 150000001735 carboxylic acids Chemical group 0.000 claims description 15
- 150000007513 acids Chemical class 0.000 claims description 14
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 13
- 239000000194 fatty acid Substances 0.000 claims description 13
- 229930195729 fatty acid Natural products 0.000 claims description 13
- 150000004665 fatty acids Chemical class 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 8
- 230000007704 transition Effects 0.000 claims description 8
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 6
- 230000006181 N-acylation Effects 0.000 claims description 6
- ZOCYQVNGROEVLU-UHFFFAOYSA-N isopentadecanoic acid Chemical compound CC(C)CCCCCCCCCCCC(O)=O ZOCYQVNGROEVLU-UHFFFAOYSA-N 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 239000003921 oil Substances 0.000 claims description 5
- 235000019198 oils Nutrition 0.000 claims description 5
- BITHHVVYSMSWAG-KTKRTIGZSA-N (11Z)-icos-11-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCC(O)=O BITHHVVYSMSWAG-KTKRTIGZSA-N 0.000 claims description 4
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 claims description 4
- XKLJLHAPJBUBNL-UHFFFAOYSA-N 12-methyltetradecanoic acid Chemical compound CCC(C)CCCCCCCCCCC(O)=O XKLJLHAPJBUBNL-UHFFFAOYSA-N 0.000 claims description 4
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 4
- OPVAJFQBSDUNQA-UHFFFAOYSA-N 3,4-dimethylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1C OPVAJFQBSDUNQA-UHFFFAOYSA-N 0.000 claims description 4
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 4
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical class OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 claims description 4
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 claims description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 4
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims description 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 claims description 4
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical class OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 4
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims description 4
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims description 4
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical class OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 claims description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 4
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 claims description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
- 235000021355 Stearic acid Nutrition 0.000 claims description 3
- 235000011054 acetic acid Nutrition 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 3
- XSXIVVZCUAHUJO-AVQMFFATSA-N (11e,14e)-icosa-11,14-dienoic acid Chemical compound CCCCC\C=C\C\C=C\CCCCCCCCCC(O)=O XSXIVVZCUAHUJO-AVQMFFATSA-N 0.000 claims description 2
- OOJGMLFHAQOYIL-SQIWNDBBSA-N (2e,4e)-hexadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C(O)=O OOJGMLFHAQOYIL-SQIWNDBBSA-N 0.000 claims description 2
- GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 claims description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- ULNRTPCFRBIMKL-GHVJWSGMSA-N (e)-2-tetracosenoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCC\C=C\C(O)=O ULNRTPCFRBIMKL-GHVJWSGMSA-N 0.000 claims description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 2
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical class C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims description 2
- ZONJATNKKGGVSU-UHFFFAOYSA-N 14-methylpentadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCC(O)=O ZONJATNKKGGVSU-UHFFFAOYSA-N 0.000 claims description 2
- UZULEJNWMHZSGY-UHFFFAOYSA-N 2-(2,3-dimethoxyphenyl)acetic acid Chemical compound COC1=CC=CC(CC(O)=O)=C1OC UZULEJNWMHZSGY-UHFFFAOYSA-N 0.000 claims description 2
- DWXSYDKEWORWBT-UHFFFAOYSA-N 2-(2-bromophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1Br DWXSYDKEWORWBT-UHFFFAOYSA-N 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- IVEWTCACRDEAOB-UHFFFAOYSA-N 2-(2-methoxyphenyl)acetic acid Chemical compound COC1=CC=CC=C1CC(O)=O IVEWTCACRDEAOB-UHFFFAOYSA-N 0.000 claims description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- ZYBVOCTZGINDED-UHFFFAOYSA-N 2-(hydroxymethoxy)benzoic acid Chemical class OCOC1=CC=CC=C1C(O)=O ZYBVOCTZGINDED-UHFFFAOYSA-N 0.000 claims description 2
- MGMNPSAERQZUIM-UHFFFAOYSA-N 2-(hydroxymethyl)benzoic acid Chemical class OCC1=CC=CC=C1C(O)=O MGMNPSAERQZUIM-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- CGMMPMYKMDITEA-UHFFFAOYSA-N 2-ethylbenzoic acid Chemical compound CCC1=CC=CC=C1C(O)=O CGMMPMYKMDITEA-UHFFFAOYSA-N 0.000 claims description 2
- WVDGHGISNBRCAO-UHFFFAOYSA-N 2-hydroxyisophthalic acid Chemical class OC(=O)C1=CC=CC(C(O)=O)=C1O WVDGHGISNBRCAO-UHFFFAOYSA-N 0.000 claims description 2
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 claims description 2
- CNXZMGRWEYQCOQ-UHFFFAOYSA-N 2-methoxy-3-phenylprop-2-enoic acid Chemical compound COC(C(O)=O)=CC1=CC=CC=C1 CNXZMGRWEYQCOQ-UHFFFAOYSA-N 0.000 claims description 2
- IPKIIZQGCWXJFM-UHFFFAOYSA-N 2-methyl-1-(4-nitrophenyl)sulfonylaziridine Chemical compound CC1CN1S(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 IPKIIZQGCWXJFM-UHFFFAOYSA-N 0.000 claims description 2
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 claims description 2
- GADSJKKDLMALGL-UHFFFAOYSA-N 2-propylbenzoic acid Chemical compound CCCC1=CC=CC=C1C(O)=O GADSJKKDLMALGL-UHFFFAOYSA-N 0.000 claims description 2
- SKBJYRPOZXOUIG-UHFFFAOYSA-N 3-(hydroxymethyl)pyridine-2-carboxylic acid Chemical compound OCC1=CC=CN=C1C(O)=O SKBJYRPOZXOUIG-UHFFFAOYSA-N 0.000 claims description 2
- HXUSUAKIRZZMGP-UHFFFAOYSA-N 3-ethylbenzoic acid Chemical compound CCC1=CC=CC(C(O)=O)=C1 HXUSUAKIRZZMGP-UHFFFAOYSA-N 0.000 claims description 2
- WHKZBVQIMVUGIH-UHFFFAOYSA-N 3-hydroxyquinoline-2-carboxylic acid Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=NC2=C1 WHKZBVQIMVUGIH-UHFFFAOYSA-N 0.000 claims description 2
- GIFHXKJTAILWRE-UHFFFAOYSA-N 3-propylbenzoic acid Chemical compound CCCC1=CC=CC(C(O)=O)=C1 GIFHXKJTAILWRE-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- ZQVKTHRQIXSMGY-UHFFFAOYSA-N 4-Ethylbenzoic acid Chemical compound CCC1=CC=C(C(O)=O)C=C1 ZQVKTHRQIXSMGY-UHFFFAOYSA-N 0.000 claims description 2
- PKGWLCZTTHWKIZ-UHFFFAOYSA-N 4-Hydroxypheoxyacetate Chemical compound OC(=O)COC1=CC=C(O)C=C1 PKGWLCZTTHWKIZ-UHFFFAOYSA-N 0.000 claims description 2
- CHHQEMBTCQDAHF-UHFFFAOYSA-N 4-hydroxy-2,3-dimethoxybenzoic acid Chemical class COC1=C(O)C=CC(C(O)=O)=C1OC CHHQEMBTCQDAHF-UHFFFAOYSA-N 0.000 claims description 2
- ATZHGRNFEFVDDJ-UHFFFAOYSA-N 4-propylbenzoic acid Chemical compound CCCC1=CC=C(C(O)=O)C=C1 ATZHGRNFEFVDDJ-UHFFFAOYSA-N 0.000 claims description 2
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 claims description 2
- YZKLUEWQADEGKP-UHFFFAOYSA-N 5-(2,4-dichlorophenyl)cyclohexane-1,3-dione Chemical compound ClC1=CC(Cl)=CC=C1C1CC(=O)CC(=O)C1 YZKLUEWQADEGKP-UHFFFAOYSA-N 0.000 claims description 2
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- AAOISIQFPPAFQO-UHFFFAOYSA-N 7:0(6Me,6Me) Chemical compound CC(C)(C)CCCCC(O)=O AAOISIQFPPAFQO-UHFFFAOYSA-N 0.000 claims description 2
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- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 2
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- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 2
- 210000000988 bone and bone Anatomy 0.000 claims description 2
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Clinical Laboratory Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102009031056.8 | 2009-06-30 | ||
| DE102009031056A DE102009031056A1 (de) | 2009-06-30 | 2009-06-30 | Kontinuierliches Verfahren zur Acrylierung von Aminogruppen tragenden organischen Säuren |
| PCT/EP2010/003444 WO2011000461A2 (de) | 2009-06-30 | 2010-06-09 | Kontinuierliches verfahren zur acylierung von aminogruppen tragenden organischen säuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2766933A1 true CA2766933A1 (en) | 2011-01-06 |
Family
ID=43128285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2766933A Abandoned CA2766933A1 (en) | 2009-06-30 | 2010-06-09 | Continuous method for acylating amino group-carrying organic acids |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20120090983A1 (https=) |
| EP (1) | EP2448913B1 (https=) |
| JP (1) | JP5851397B2 (https=) |
| KR (1) | KR20120060199A (https=) |
| CA (1) | CA2766933A1 (https=) |
| DE (1) | DE102009031056A1 (https=) |
| ES (1) | ES2410632T3 (https=) |
| WO (1) | WO2011000461A2 (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006047617B4 (de) * | 2006-10-09 | 2008-11-27 | Clariant International Limited | Verfahren zur Herstellung basischer (Meth)acrylamide |
| DE102006047619B4 (de) * | 2006-10-09 | 2008-11-13 | Clariant International Limited | Verfahren zur Herstellung basischer Fettsäureamide |
| DE102008017213B4 (de) * | 2008-04-04 | 2012-08-09 | Clariant International Limited | Kontinuierliches Verfahren zur Herstellung von Amiden aliphatischer Hydroxycarbonsäuren |
| DE102008017216B4 (de) * | 2008-04-04 | 2013-08-14 | Clariant International Ltd. | Kontinuierliches Verfahren zur Herstellung von Fettsäureamiden |
| DE102008017219A1 (de) * | 2008-04-04 | 2009-10-08 | Clariant International Ltd. | Verfahren zur Herstellung von Amiden in Gegenwart von überhitztem Wasser |
| DE102008017215B4 (de) * | 2008-04-04 | 2012-08-09 | Clariant International Ltd. | Kontinuierliches Verfahren zur Herstellung von Amiden ethylenisch ungesättigter Carbonsäuren |
| DE102008017218B4 (de) * | 2008-04-04 | 2011-09-22 | Clariant International Ltd. | Kontinuierliches Verfahren zur Herstellung von Amiden niederer aliphatischer Carbonsäuren |
| DE102008017214B4 (de) * | 2008-04-04 | 2012-02-16 | Clariant International Limited | Kontinuierliches Verfahren zur Herstellung von Fettsäurealkanolamiden |
| DE102008017217A1 (de) * | 2008-04-04 | 2009-10-08 | Clariant International Ltd. | Kontinuierliches Verfahren zur Herstellung von Amiden aromatischer Carbonsäuren |
| DE102009031059A1 (de) | 2009-06-30 | 2011-01-05 | Clariant International Ltd. | Vorrichtung zur kontinuierlichen Durchführung chemischer Reaktionen bei hohen Temperaturen |
| DE102009031058A1 (de) * | 2009-06-30 | 2011-01-27 | Clariant International Ltd. | Kontinuierliches Verfahren zur Herstellung von Amiden aromatischer Carbonsäuren |
| DE102009042523B4 (de) | 2009-09-22 | 2012-02-16 | Clariant International Ltd. | Vorrichtung und Verfahren zur kontinuierlichen Durchführung heterogen katalysierter chemischer Reaktionen bei hohen Temperaturen |
| DE102009042522A1 (de) | 2009-09-22 | 2011-04-07 | Clariant International Ltd. | Kontinuierliches Umesterungsverfahren |
| DE102010056564A1 (de) | 2010-12-30 | 2012-07-05 | Clariant International Limited | Hydroxylgruppen und Estergruppen tragende Polymere und Verfahren zu ihrer Herstellung |
| DE102010056565A1 (de) | 2010-12-30 | 2012-07-05 | Clariant International Ltd. | Verfahren zur Modifizierung Hydroxylgruppen tragender Polymere |
| CN106588710B (zh) * | 2016-12-12 | 2018-07-10 | 湖北远大生命科学与技术有限责任公司 | 一种应用微波合成n-酰基-n-甲基牛磺酸盐的方法 |
| EP3647303B1 (en) * | 2018-10-31 | 2022-08-31 | Clariant International Ltd | Process for preparing fatty acid chlorides and n-acyl amino acid salts |
| JP2021038146A (ja) * | 2019-08-30 | 2021-03-11 | マイクロ波化学株式会社 | Ｎ−アシルアミン類の製造方法 |
| IT202000030185A1 (it) * | 2020-12-09 | 2022-06-09 | Prod Gianni S R L | Alchilesteri di lipoamminoacidi quali spf boosters |
| CN114031516B (zh) * | 2021-11-23 | 2023-09-01 | 长沙普济生物科技股份有限公司 | 一种基于锆催化剂催化合成n-酰基氨基酸表面活性剂的方法 |
| CN114181119B (zh) * | 2021-12-18 | 2023-04-18 | 湖北天安日用化工有限公司 | 一种甲基月桂酰基牛磺酸钠的制备方法 |
| CN115160189B (zh) * | 2022-08-11 | 2023-06-16 | 广州天赐高新材料股份有限公司 | 一种n-酰基甲基牛磺酸钠的连续化制备方法 |
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| US3461261A (en) * | 1966-10-31 | 1969-08-12 | Du Pont | Heating apparatus |
| US3836551A (en) * | 1970-01-30 | 1974-09-17 | Roehm Gmbh | Method for making salts of n-acylamino carboxylic acids |
| JPH01133910A (ja) * | 1987-06-08 | 1989-05-26 | Cil Inc | マイクロ波エネルギ−を使用して発煙硫酸から三酸化硫黄を発生させる方法及び装置 |
| WO1990003840A1 (en) * | 1988-10-10 | 1990-04-19 | Commonwealth Scientific And Industrial Research Organisation | Method and apparatus for continuous chemical reactions |
| JP2784789B2 (ja) * | 1989-03-27 | 1998-08-06 | 山本化成株式会社 | ２―アルキルアントラキノンの製造方法 |
| US6020580A (en) * | 1997-01-06 | 2000-02-01 | International Business Machines Corporation | Microwave applicator having a mechanical means for tuning |
| US6020579A (en) * | 1997-01-06 | 2000-02-01 | International Business Machines Corporation | Microwave applicator having a mechanical means for tuning |
| US5114684A (en) * | 1990-12-13 | 1992-05-19 | Serawaste Systems Corporation | In-line electromagnetic energy wave applicator |
| US5471037A (en) * | 1992-08-18 | 1995-11-28 | E. I. Du Pont De Nemours And Company | Process for preparing polymeric material with microwave |
| FR2698869B1 (fr) * | 1992-12-09 | 1995-02-24 | Morelle Jean | Acylaminoacides obtenus à partir de fibres issues du Bombyx Mori. |
| DE4433977A1 (de) * | 1994-09-23 | 1996-03-28 | Basf Ag | Verfahren zur Herstellung von N-Acylaminocarbonsäuren und N-Acylaminosulfonsäuren sowie deren Alkalimetallsalzen |
| US5710295A (en) * | 1995-06-06 | 1998-01-20 | Hampshire Chemical Corp. | Preparation of alkali metal acyl amino acids |
| US5646319A (en) * | 1995-06-23 | 1997-07-08 | The Procter & Gamble Company | Synthesis of N-acyl-N-alkylcarboxylates |
| FR2751830B1 (fr) * | 1996-07-23 | 1998-10-23 | Prolabo Sa | Dispositif pour realiser des reactions chimiques sous micro-ondes sur une grande quantite de produits |
| ES2256546T3 (es) * | 2001-10-19 | 2006-07-16 | Biotage Ab | Aparato para calentar por microondas. |
| FR2849343B1 (fr) * | 2002-12-23 | 2009-01-23 | Aldivia | Synthese chimique comportant un traitement thermique par chauffage dielectrique intermittent, combine a un systeme de recirculation |
| US7393920B2 (en) * | 2003-06-23 | 2008-07-01 | Cem Corporation | Microwave-assisted peptide synthesis |
| JP4759668B2 (ja) * | 2004-05-11 | 2011-08-31 | 株式会社Ｉｄｘ | マイクロ波加熱装置 |
| JP2006272055A (ja) * | 2005-03-28 | 2006-10-12 | Idx Corp | マイクロ波化学反応装置 |
| JP2006181533A (ja) * | 2004-12-28 | 2006-07-13 | Idx Corp | マイクロ波化学反応装置 |
| JP2007222696A (ja) * | 2005-12-23 | 2007-09-06 | Tokyo Electric Power Co Inc:The | マイクロ波反応用の触媒カラム及びそれを用いた分解処理方法 |
| CN100352793C (zh) * | 2006-01-20 | 2007-12-05 | 杨鸿生 | 用于以天然气制乙烯的槽波导微波化学反应设备及制备方法 |
| DE102006047619B4 (de) * | 2006-10-09 | 2008-11-13 | Clariant International Limited | Verfahren zur Herstellung basischer Fettsäureamide |
| WO2008043493A1 (de) * | 2006-10-09 | 2008-04-17 | Clariant Finance (Bvi) Limited | Verfahren zur herstellung von fettsäurealkanolamiden |
| US8128788B2 (en) * | 2008-09-19 | 2012-03-06 | Rf Thummim Technologies, Inc. | Method and apparatus for treating a process volume with multiple electromagnetic generators |
-
2009
- 2009-06-30 DE DE102009031056A patent/DE102009031056A1/de not_active Withdrawn
-
2010
- 2010-06-09 CA CA2766933A patent/CA2766933A1/en not_active Abandoned
- 2010-06-09 US US13/378,181 patent/US20120090983A1/en not_active Abandoned
- 2010-06-09 EP EP10724308.1A patent/EP2448913B1/de not_active Not-in-force
- 2010-06-09 WO PCT/EP2010/003444 patent/WO2011000461A2/de not_active Ceased
- 2010-06-09 ES ES10724308T patent/ES2410632T3/es active Active
- 2010-06-09 JP JP2012518032A patent/JP5851397B2/ja not_active Expired - Fee Related
- 2010-06-09 KR KR1020127002479A patent/KR20120060199A/ko not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| KR20120060199A (ko) | 2012-06-11 |
| US20120090983A1 (en) | 2012-04-19 |
| WO2011000461A3 (de) | 2011-03-31 |
| JP2012531450A (ja) | 2012-12-10 |
| EP2448913A2 (de) | 2012-05-09 |
| WO2011000461A2 (de) | 2011-01-06 |
| ES2410632T3 (es) | 2013-07-02 |
| DE102009031056A1 (de) | 2011-01-27 |
| JP5851397B2 (ja) | 2016-02-03 |
| EP2448913B1 (de) | 2013-04-24 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20150605 |
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| FZDE | Discontinued |
Effective date: 20171011 |