EP1856034A1 - Verfahren zur herstellung von bifunktionellen ammoniumnitrilen - Google Patents
Verfahren zur herstellung von bifunktionellen ammoniumnitrilenInfo
- Publication number
- EP1856034A1 EP1856034A1 EP06723108A EP06723108A EP1856034A1 EP 1856034 A1 EP1856034 A1 EP 1856034A1 EP 06723108 A EP06723108 A EP 06723108A EP 06723108 A EP06723108 A EP 06723108A EP 1856034 A1 EP1856034 A1 EP 1856034A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- dialkylaminoacetonitrile
- general formula
- alkyl
- works
- formula
- 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.)
- Withdrawn
Links
- -1 ammonium nitriles Chemical class 0.000 title claims abstract description 30
- 230000001588 bifunctional effect Effects 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- PLXBWEPPAAQASG-UHFFFAOYSA-N 2-(Dimethylamino)acetonitrile Chemical compound CN(C)CC#N PLXBWEPPAAQASG-UHFFFAOYSA-N 0.000 claims description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- LVPZSMIBSMMLPI-UHFFFAOYSA-N 2-(diethylamino)acetonitrile Chemical compound CCN(CC)CC#N LVPZSMIBSMMLPI-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- 239000003599 detergent Substances 0.000 claims description 4
- GJRQTCIYDGXPES-UHFFFAOYSA-N isobutyl acetate Chemical compound CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 4
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- ZPVXOYNIUUYGQD-UHFFFAOYSA-N 2-(dibutylamino)acetonitrile Chemical compound CCCCN(CC#N)CCCC ZPVXOYNIUUYGQD-UHFFFAOYSA-N 0.000 claims description 2
- PTMNLAPQVWUAFM-UHFFFAOYSA-N 2-(dihexylamino)acetonitrile Chemical compound CCCCCCN(CC#N)CCCCCC PTMNLAPQVWUAFM-UHFFFAOYSA-N 0.000 claims description 2
- ZFQYTSCUGODUDB-UHFFFAOYSA-N 2-(dipropylamino)acetonitrile Chemical compound CCCN(CCC)CC#N ZFQYTSCUGODUDB-UHFFFAOYSA-N 0.000 claims description 2
- NDVZMKCMHIWQGQ-UHFFFAOYSA-N 2-(ethylamino)propanenitrile Chemical compound CCNC(C)C#N NDVZMKCMHIWQGQ-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005011 alkyl ether group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims 3
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims 1
- 238000004140 cleaning Methods 0.000 claims 1
- 239000012459 cleaning agent Substances 0.000 claims 1
- 239000000645 desinfectant Substances 0.000 claims 1
- 238000004851 dishwashing Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 description 8
- 239000012190 activator Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000004061 bleaching Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 6
- 229940113088 dimethylacetamide Drugs 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 125000005219 aminonitrile group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- XSVSPKKXQGNHMD-UHFFFAOYSA-N 5-bromo-3-methyl-1,2-thiazole Chemical compound CC=1C=C(Br)SN=1 XSVSPKKXQGNHMD-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 125000004982 dihaloalkyl group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 125000003106 haloaryl group Chemical group 0.000 description 2
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SMWUDAKKCDQTPV-UHFFFAOYSA-N 1,3-dimethylimidazolidine Chemical compound CN1CCN(C)C1 SMWUDAKKCDQTPV-UHFFFAOYSA-N 0.000 description 1
- HYOAGWAIGJXNQH-UHFFFAOYSA-N 1-bromo-1-chloropropane Chemical compound CCC(Cl)Br HYOAGWAIGJXNQH-UHFFFAOYSA-N 0.000 description 1
- NTIGNJOEVBTPJJ-UHFFFAOYSA-N 3,3-dibromopentane Chemical compound CCC(Br)(Br)CC NTIGNJOEVBTPJJ-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 235000021438 curry Nutrition 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3902—Organic or inorganic per-compounds combined with specific additives
- C11D3/3905—Bleach activators or bleach catalysts
- C11D3/3907—Organic compounds
- C11D3/3917—Nitrogen-containing compounds
- C11D3/3927—Quarternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Definitions
- the present invention relates to the synthesis of bifunctional
- Ammonium nitriles by one-step reaction of dialkylaminoacetonitriles with dihaloalkylene or dihaloarylene.
- EP-A-458 386 are obtained in EP-A-458 386 as part of a two-step reaction.
- first step the synthesis of a tertiary aminonitrile by reaction of the corresponding aldehyde or ketone with potassium cyanide and a secondary amine and in a second step, the quaternization of the aminonitrile with dimethyl sulfate.
- EP-A-464 880 the quaternization of the aminonitrile is carried out with para-methyltoluenesulfonate or para-dodecylalkylbenzenesulfonate.
- the corresponding tertiary amine is reacted with chloroacetonitrile to the respective ammonium nitrile.
- a problem for the industrial applicability of the process is the high cost of the haloacetonitriles, which make the production of these used as bleach activators in detergents and cleaners class more expensive.
- the present invention thus provides a process for the preparation of bifunctional ammonium nitriles of the formula (1)
- R 1 , R 2 , R 3 and R 4 are each individually hydrogen, hydroxyl, d- to C 2 4-alkyl, C 2 - to
- R 5 and R 6 are each independently a straight or branched Cr to C 2 4 alkyl, alkenyl or alkyl ether group, and X is an anion, the variable n is an integer 1-16 alkyl; wherein a dialkylaminoacetonitrile of the general formula (2)
- the process according to the invention is carried out by first dissolving or suspending the dialkylaminoacetonitrile of the formula (2) in a suitable polar aprotic solvent.
- suitable solvents are, for example: ethyl acetate, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate and mixtures thereof, dimethyl sulfoxide, N-methylpyrrolidone, 1,3-dimethylimidazolidine. on.
- a dihaloalkyl compound or a haloaryl compound of the general formula (3) in the form of substance or as a solution is added dropwise to this solution or suspension.
- the two halogen atoms X may be the same or different.
- Dialkylaminoacetonitrile is 1, 8 to 2.5, preferably 2.0 to 2.3 molar equivalents based on the dihaloalkyl or haloaryl. Suitable dialkylaminoacetonitrile dimethylaminoacetonitrile, diethylaminoacetonitrile, methyl ethylaminoacetonitrile, di-n-propylaminoacetonitrile, di-n-butylaminoacetonitrile, di-n-hexylaminoacetonitrile, dimethylaminoacetonitrile and are preferred
- the reaction temperature is generally from 20 to 120 0 C, preferably 30 to 100 0 C, particularly preferably 40 to 8O 0 C.
- the reaction takes place over a period of 1 to 10 hours, preferably 2 to 9 hours, more preferably 4 to 8 hours ,
- the resulting product can be removed by filtration, suction filtration,
- Reaction mixture was stirred at 60 ° C for 5 hours. The reaction mixture was cooled to room temperature and the precipitated solid was filtered off.
- Example 5 Bleaching performance of bifunctional ammonium nitriles
- Bleaching compositions were prepared and tested with the inventive cationic nitrile compounds of Inventive Examples 1 and 2 and Comparative Substances 3 and 4.
- the compounds 1 to 4 have the following structure:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005009137A DE102005009137A1 (de) | 2005-03-01 | 2005-03-01 | Verfahren zur Herstellung von bifunktionellen Ammoniumnitrilen |
| PCT/EP2006/001735 WO2006092247A1 (de) | 2005-03-01 | 2006-02-24 | Verfahren zur herstellung von bifunktionellen ammoniumnitrilen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1856034A1 true EP1856034A1 (de) | 2007-11-21 |
Family
ID=36609298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP06723108A Withdrawn EP1856034A1 (de) | 2005-03-01 | 2006-02-24 | Verfahren zur herstellung von bifunktionellen ammoniumnitrilen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20090023942A1 (hu) |
| EP (1) | EP1856034A1 (hu) |
| JP (1) | JP2008531622A (hu) |
| DE (1) | DE102005009137A1 (hu) |
| WO (1) | WO2006092247A1 (hu) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2387723A (en) * | 1940-04-03 | 1945-10-30 | Celanese Corp | Manufacture of organic compounds |
| US4915863A (en) * | 1987-08-14 | 1990-04-10 | Kao Corporation | Bleaching composition |
| JP2551962B2 (ja) * | 1988-02-03 | 1996-11-06 | 花王株式会社 | 自動食器洗浄機用洗剤 |
| JPH02132196A (ja) * | 1988-11-11 | 1990-05-21 | Kao Corp | 漂白剤及び漂白洗剤組成物 |
| DE10211389A1 (de) * | 2002-03-15 | 2003-09-25 | Clariant Gmbh | Ammoniumnitrile und deren Verwendung als hydrophobe Bleichaktivatoren |
-
2005
- 2005-03-01 DE DE102005009137A patent/DE102005009137A1/de not_active Withdrawn
-
2006
- 2006-02-24 WO PCT/EP2006/001735 patent/WO2006092247A1/de active Application Filing
- 2006-02-24 JP JP2007557395A patent/JP2008531622A/ja not_active Withdrawn
- 2006-02-24 US US11/885,610 patent/US20090023942A1/en not_active Abandoned
- 2006-02-24 EP EP06723108A patent/EP1856034A1/de not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2006092247A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006092247A1 (de) | 2006-09-08 |
| DE102005009137A1 (de) | 2006-09-07 |
| US20090023942A1 (en) | 2009-01-22 |
| JP2008531622A (ja) | 2008-08-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 20071001 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR |
|
| 17Q | First examination report despatched |
Effective date: 20080116 |
|
| DAX | Request for extension of the european patent (deleted) | ||
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
|
| 18W | Application withdrawn |
Effective date: 20090805 |