JP2773049B2 - 四級塩化方法 - Google Patents
四級塩化方法Info
- Publication number
- JP2773049B2 JP2773049B2 JP1502099A JP50209989A JP2773049B2 JP 2773049 B2 JP2773049 B2 JP 2773049B2 JP 1502099 A JP1502099 A JP 1502099A JP 50209989 A JP50209989 A JP 50209989A JP 2773049 B2 JP2773049 B2 JP 2773049B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- reactor
- iii
- flow rate
- weight
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 19
- 150000001805 chlorine compounds Chemical group 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000007864 aqueous solution Substances 0.000 claims description 16
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 13
- 239000007789 gas Substances 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 11
- 239000012429 reaction media Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 16
- 229940050176 methyl chloride Drugs 0.000 description 8
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 6
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229960003505 mequinol Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000005956 quaternization reaction Methods 0.000 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 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- WZFUNVKBTGDQDB-UHFFFAOYSA-N 2-aminoethyl 2,3-dimethylbut-2-enoate;hydrochloride Chemical compound Cl.CC(C)=C(C)C(=O)OCCN WZFUNVKBTGDQDB-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
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-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
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 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
- 239000012320 chlorinating reagent Substances 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
- 230000007423 decrease 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
- -1 dimethylethylaminoethyl acrylate Chemical compound 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229960004337 hydroquinone Drugs 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8801636 | 1988-02-11 | ||
| FR88/1636 | 1988-02-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03502451A JPH03502451A (ja) | 1991-06-06 |
| JP2773049B2 true JP2773049B2 (ja) | 1998-07-09 |
Family
ID=9363186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1502099A Expired - Lifetime JP2773049B2 (ja) | 1988-02-11 | 1989-02-02 | 四級塩化方法 |
Country Status (10)
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 NL NL8920072A patent/NL193088C/nl not_active IP Right Cessation
- 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 WO PCT/FR1989/000037 patent/WO1989007589A1/fr active Application Filing
- 1989-02-09 IT IT8947625A patent/IT1230445B/it active
- 1989-02-09 ES ES8900468A patent/ES2010133A6/es not_active Expired
- 1989-02-10 CA CA000590756A patent/CA1333613C/fr not_active Expired - Fee Related
- 1989-02-10 BE BE8900135A patent/BE1006876A4/fr not_active IP Right Cessation
-
1990
- 1990-07-09 GB GB9015070A patent/GB2232980B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB9015070D0 (en) | 1990-09-26 |
| CA1333613C (fr) | 1994-12-20 |
| GB2232980B (en) | 1992-01-08 |
| IT1230445B (it) | 1991-10-23 |
| CH678724A5 (enrdf_load_stackoverflow) | 1991-10-31 |
| JPH03502451A (ja) | 1991-06-06 |
| BE1006876A4 (fr) | 1995-01-17 |
| DE3990121C2 (de) | 1999-02-11 |
| NL193088C (nl) | 1998-10-05 |
| GB2232980A (en) | 1991-01-02 |
| IT8947625A0 (it) | 1989-02-09 |
| NL8920072A (nl) | 1990-12-03 |
| ES2010133A6 (es) | 1989-10-16 |
| NL193088B (nl) | 1998-06-02 |
| WO1989007589A1 (fr) | 1989-08-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4745214A (en) | Process for the preparation of an aqueous solution of unsaturated quaternary ammonium salts | |
| JP2776597B2 (ja) | 四級塩化方法 | |
| JP2945356B2 (ja) | 不飽和第四級アンモニム塩の安定な水溶液 | |
| JP2773049B2 (ja) | 四級塩化方法 | |
| US5260480A (en) | Quaternization process | |
| US5919974A (en) | Process for the manufacture of aqueous solutions of unsaturated quaternary ammonium salts | |
| JP3789755B2 (ja) | 不飽和第四級アンモにウム塩の水溶液の製造方法 | |
| JP3640612B2 (ja) | 不飽和第四級アンモニウム塩の水溶液の製造方法 | |
| JPH02272A (ja) | アルキルチオエチルアミン塩類の製造プロセス | |
| JP3032155B2 (ja) | ベタインモノマーの製法 | |
| JP2002155104A (ja) | カチオン性アクリルオイルオキシエチルトリメチル塩化アンモニウム共重合体のモル質量を増加させる方法と、それに対応する共重合体 | |
| JP2000229919A (ja) | 高純度不飽和第四級アンモニウム塩水溶液の製造方法 | |
| JPH0995586A (ja) | 水溶性整髪用樹脂組成物およびその製法 | |
| JP2003286235A (ja) | 不飽和第四級アンモニウム塩の製造方法 | |
| JPS6318936B2 (enrdf_load_stackoverflow) | ||
| JP2705827B2 (ja) | 不飽和第四級アンモニウム塩の製造方法 | |
| JPH08283194A (ja) | ３−クロロプロピオン酸の製造方法 | |
| FR2642424A1 (fr) | Procede de preparation de solutions aqueuses de sels insatures d'ammonium quaternaire | |
| JPH03135945A (ja) | 第四級アンモニウム塩の製造方法 | |
| JPH02212457A (ja) | 不飽和第４級アンモニウム塩の製造方法 | |
| JPH04198154A (ja) | テトラシクロドデセン誘導体の製造方法 | |
| JPH0553785B2 (enrdf_load_stackoverflow) | ||
| JPH04217648A (ja) | 不飽和第四級アンモニウム塩の製造法 | |
| JPH04124164A (ja) | 不飽和第４級アンモニウム塩水溶液の製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050127 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20070524 |
|
| A131 | Notification of reasons for refusal |
Effective date: 20070605 Free format text: JAPANESE INTERMEDIATE CODE: A131 |
|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20070726 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20080115 |
|
| A61 | First payment of annual fees (during grant procedure) |
Effective date: 20080121 Free format text: JAPANESE INTERMEDIATE CODE: A61 |
|
| R150 | Certificate of patent (=grant) or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (prs date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110125 Year of fee payment: 3 |
|
| S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
| FPAY | Renewal fee payment (prs date is renewal date of database) |
Year of fee payment: 3 Free format text: PAYMENT UNTIL: 20110125 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| LAPS | Cancellation because of no payment of annual fees |