CA2269082A1 - Procede pour preparer des activateurs de blanchiment a base d'imides acycliques asymetriques - Google Patents
Procede pour preparer des activateurs de blanchiment a base d'imides acycliques asymetriques Download PDFInfo
- Publication number
- CA2269082A1 CA2269082A1 CA002269082A CA2269082A CA2269082A1 CA 2269082 A1 CA2269082 A1 CA 2269082A1 CA 002269082 A CA002269082 A CA 002269082A CA 2269082 A CA2269082 A CA 2269082A CA 2269082 A1 CA2269082 A1 CA 2269082A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- carboxylic acid
- imide
- amide
- linear
- 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
Links
- -1 acyclic imide Chemical class 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 239000012190 activator Substances 0.000 title abstract description 49
- 239000007844 bleaching agent Substances 0.000 title abstract description 40
- 150000001408 amides Chemical class 0.000 claims abstract description 40
- 150000003949 imides Chemical class 0.000 claims abstract description 35
- 150000003855 acyl compounds Chemical class 0.000 claims abstract description 26
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims abstract description 25
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 16
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims abstract description 16
- 239000011541 reaction mixture Substances 0.000 claims abstract description 14
- 150000001733 carboxylic acid esters Chemical class 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 150000001412 amines Chemical class 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000001735 carboxylic acids Chemical class 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- 238000010936 aqueous wash Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000004508 fractional distillation Methods 0.000 claims description 3
- 238000000638 solvent extraction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 125000002252 acyl group Chemical group 0.000 abstract description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000002209 hydrophobic effect Effects 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000010933 acylation Effects 0.000 description 11
- 238000005917 acylation reaction Methods 0.000 description 11
- 150000008064 anhydrides Chemical class 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000004061 bleaching Methods 0.000 description 8
- UUEFORZDCGMFHB-UHFFFAOYSA-N n-methyl-n-nonylacetamide Chemical compound CCCCCCCCCN(C)C(C)=O UUEFORZDCGMFHB-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- NTQYXUJLILNTFH-UHFFFAOYSA-N nonanoyl chloride Chemical compound CCCCCCCCC(Cl)=O NTQYXUJLILNTFH-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000005643 Pelargonic acid Substances 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- DWWMMANVIWQXLM-UHFFFAOYSA-N n-methylnonanamide Chemical compound CCCCCCCCC(=O)NC DWWMMANVIWQXLM-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- FRPJTGXMTIIFIT-UHFFFAOYSA-N tetraacetylethylenediamine Chemical group CC(=O)C(N)(C(C)=O)C(N)(C(C)=O)C(C)=O FRPJTGXMTIIFIT-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000004851 dishwashing Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000006358 imidation reaction Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 101100281516 Caenorhabditis elegans fox-1 gene Proteins 0.000 description 1
- 238000000023 Kugelrohr distillation Methods 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 238000010640 amide synthesis reaction Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000005323 carbonate salts Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 229910052806 inorganic carbonate Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- GHLZUHZBBNDWHW-UHFFFAOYSA-N nonanamide Chemical compound CCCCCCCCC(N)=O GHLZUHZBBNDWHW-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011012 sanitization Methods 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/90—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated
- C07C233/91—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated with carbon atoms of the carboxamide groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/90—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
L'invention concerne un procédé permettant de préparer des activateurs de blanchiment à base d'imides acycliques asymétriques. Les composés préparés selon ledit procédé sont représentés par la formule (I), dans laquelle R1 est un groupe alkyle C7-C13 saturé ou insaturé, à chaîne linéaire ou ramifiée, R2 est un groupe alkyle C1-C8 saturé ou insaturé, à chaîne linéaire ou ramifiée, et R3 est un groupe alkyle C1-C4 saturé ou insaturé, à chaîne linéaire ou ramifiée. Selon le procédé, on fait réagir avec un composé acyle réactif, de façon à former ledit imide, un amide de formule (II), dans laquelle Y est choisi dans le groupe constitué de R1 et R3, et où ledit composé acyle réactif contient ledit groupe R3 quand Y est R1 et ledit groupe R1 quand Y est R3, ledit groupe acyle réactif étant de préférence choisi dans le groupe de composés comprenant les halogénures, les esters et les anhydrides de l'acide carboxylique; puis on sépare ledit imide du mélange de réaction.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2859996P | 1996-10-16 | 1996-10-16 | |
| US60/028,599 | 1996-10-16 | ||
| PCT/US1997/017910 WO1998016496A1 (fr) | 1996-10-16 | 1997-10-09 | Procede pour preparer des activateurs de blanchiment a base d'imides acycliques asymetriques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2269082A1 true CA2269082A1 (fr) | 1998-04-23 |
Family
ID=21844344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002269082A Abandoned CA2269082A1 (fr) | 1996-10-16 | 1997-10-09 | Procede pour preparer des activateurs de blanchiment a base d'imides acycliques asymetriques |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0934251A1 (fr) |
| AU (1) | AU4745397A (fr) |
| CA (1) | CA2269082A1 (fr) |
| WO (1) | WO1998016496A1 (fr) |
| ZA (1) | ZA979200B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT201600070454A1 (it) * | 2016-07-06 | 2016-10-06 | 3V Sigma Spa | Attivatori di composti perossigenati |
| CN113548977A (zh) * | 2021-07-12 | 2021-10-26 | 广州乐信生物科技有限公司 | N-甲基-β-丙氨酸衍生物的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2672470A (en) * | 1948-02-24 | 1954-03-16 | Armour & Co | Preparation of the higher monoacylamides from monoamides and acid halides |
| DE2509481C3 (de) * | 1975-03-05 | 1978-03-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von N-Acetylsalicylamid |
| US4158560A (en) * | 1977-11-17 | 1979-06-19 | Gaf Corporation | Broad spectrum herbicidal diacylimide compositions |
-
1997
- 1997-10-09 WO PCT/US1997/017910 patent/WO1998016496A1/fr not_active Ceased
- 1997-10-09 AU AU47453/97A patent/AU4745397A/en not_active Abandoned
- 1997-10-09 CA CA002269082A patent/CA2269082A1/fr not_active Abandoned
- 1997-10-09 EP EP97909967A patent/EP0934251A1/fr not_active Ceased
- 1997-10-14 ZA ZA979200A patent/ZA979200B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA979200B (en) | 1998-07-20 |
| EP0934251A1 (fr) | 1999-08-11 |
| WO1998016496A1 (fr) | 1998-04-23 |
| AU4745397A (en) | 1998-05-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |