NL193088C - Werkwijze voor de bereiding van waterige oplossingen van onverzadigde quaternaire ammoniumzouten. - Google Patents
Werkwijze voor de bereiding van waterige oplossingen van onverzadigde quaternaire ammoniumzouten. Download PDFInfo
- Publication number
- NL193088C NL193088C NL8920072A NL8920072A NL193088C NL 193088 C NL193088 C NL 193088C NL 8920072 A NL8920072 A NL 8920072A NL 8920072 A NL8920072 A NL 8920072A NL 193088 C NL193088 C NL 193088C
- Authority
- NL
- Netherlands
- Prior art keywords
- reaction
- water
- quaternary ammonium
- unsaturated quaternary
- ammonium salts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims description 12
- 239000007864 aqueous solution Substances 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 20
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229940050176 methyl chloride Drugs 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 3
- FZGFBJMPSHGTRQ-UHFFFAOYSA-M trimethyl(2-prop-2-enoyloxyethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCOC(=O)C=C FZGFBJMPSHGTRQ-UHFFFAOYSA-M 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- VMEZXMFPKOMWHR-UHFFFAOYSA-N (dimethylamino)methyl prop-2-enoate Chemical compound CN(C)COC(=O)C=C VMEZXMFPKOMWHR-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- UFQHFMGRRVQFNA-UHFFFAOYSA-N 3-(dimethylamino)propyl prop-2-enoate Chemical compound CN(C)CCCOC(=O)C=C UFQHFMGRRVQFNA-UHFFFAOYSA-N 0.000 description 1
- ZWAPMFBHEQZLGK-UHFFFAOYSA-N 5-(dimethylamino)-2-methylidenepentanamide Chemical compound CN(C)CCCC(=C)C(N)=O ZWAPMFBHEQZLGK-UHFFFAOYSA-N 0.000 description 1
- 241001104043 Syringa Species 0.000 description 1
- 235000004338 Syringa vulgaris Nutrition 0.000 description 1
- -1 air or pure oxygen Chemical compound 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- USFMMZYROHDWPJ-UHFFFAOYSA-N trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium Chemical compound CC(=C)C(=O)OCC[N+](C)(C)C USFMMZYROHDWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/38—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/08—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8801636 | 1988-02-11 | ||
| FR8801636 | 1988-02-11 | ||
| PCT/FR1989/000037 WO1989007589A1 (fr) | 1988-02-11 | 1989-02-02 | Procede de quaternisation |
| FR8900037 | 1989-02-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NL8920072A NL8920072A (nl) | 1990-12-03 |
| NL193088B NL193088B (nl) | 1998-06-02 |
| NL193088C true NL193088C (nl) | 1998-10-05 |
Family
ID=9363186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8920072A NL193088C (nl) | 1988-02-11 | 1989-02-02 | Werkwijze voor de bereiding van waterige oplossingen van onverzadigde quaternaire ammoniumzouten. |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JP2773049B2 (fr) |
| BE (1) | BE1006876A4 (fr) |
| CA (1) | CA1333613C (fr) |
| CH (1) | CH678724A5 (fr) |
| DE (1) | DE3990121C2 (fr) |
| ES (1) | ES2010133A6 (fr) |
| GB (1) | GB2232980B (fr) |
| IT (1) | IT1230445B (fr) |
| NL (1) | NL193088C (fr) |
| WO (1) | WO1989007589A1 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3938528A1 (de) * | 1989-11-21 | 1991-05-23 | Basf Ag | Verfahren zur herstellung waessriger loesungen oder suspensionen von quaternierungsprodukten von tertiaeren aminoalkylestern oder tertiaeren aminoalkylamiden der acryl- oder methacrylsaeure, beispielsweise von dimethylaminoethylacrylat-methochlorid |
| SE0104346L (sv) | 2001-12-21 | 2003-06-22 | Akzo Nobel Nv | Process för kontinuerlig kvartärnering av tertiära aminer med en alkylhalid |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2608868A1 (de) * | 1975-03-05 | 1976-09-16 | Mitsubishi Chem Ind | Verfahren zur herstellung eines quartaeren ammoniumsalzes |
| JPS5692252A (en) * | 1979-12-27 | 1981-07-25 | Nitto Chem Ind Co Ltd | Production of unsaturated quaternary ammonium salt |
| JPS57126452A (en) * | 1981-01-28 | 1982-08-06 | Sanyo Chem Ind Ltd | Preparation of quaternary ammonium salt |
| US4745214A (en) * | 1986-06-20 | 1988-05-17 | Norsolor | Process for the preparation of an aqueous solution of unsaturated quaternary ammonium salts |
-
1989
- 1989-02-02 DE DE3990121A patent/DE3990121C2/de not_active Expired - Fee Related
- 1989-02-02 WO PCT/FR1989/000037 patent/WO1989007589A1/fr active Application Filing
- 1989-02-02 CH CH3591/89A patent/CH678724A5/fr not_active IP Right Cessation
- 1989-02-02 JP JP1502099A patent/JP2773049B2/ja not_active Expired - Lifetime
- 1989-02-02 NL NL8920072A patent/NL193088C/nl not_active IP Right Cessation
- 1989-02-09 ES ES8900468A patent/ES2010133A6/es not_active Expired
- 1989-02-09 IT IT8947625A patent/IT1230445B/it active
- 1989-02-10 BE BE8900135A patent/BE1006876A4/fr not_active IP Right Cessation
- 1989-02-10 CA CA000590756A patent/CA1333613C/fr not_active Expired - Fee Related
-
1990
- 1990-07-09 GB GB9015070A patent/GB2232980B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE1006876A4 (fr) | 1995-01-17 |
| GB9015070D0 (en) | 1990-09-26 |
| ES2010133A6 (es) | 1989-10-16 |
| CA1333613C (fr) | 1994-12-20 |
| JP2773049B2 (ja) | 1998-07-09 |
| IT8947625A0 (it) | 1989-02-09 |
| WO1989007589A1 (fr) | 1989-08-24 |
| DE3990121C2 (de) | 1999-02-11 |
| CH678724A5 (fr) | 1991-10-31 |
| NL8920072A (nl) | 1990-12-03 |
| GB2232980B (en) | 1992-01-08 |
| JPH03502451A (ja) | 1991-06-06 |
| NL193088B (nl) | 1998-06-02 |
| IT1230445B (it) | 1991-10-23 |
| GB2232980A (en) | 1991-01-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1B | A search report has been drawn up | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BC | A request for examination has been filed | ||
| BN | A decision not to publish the application has become irrevocable | ||
| V1 | Lapsed because of non-payment of the annual fee |
Effective date: 20020901 |