JP2547381B2 - 不飽和第四アンモニウム塩水溶液の製造方法 - Google Patents
不飽和第四アンモニウム塩水溶液の製造方法Info
- Publication number
- JP2547381B2 JP2547381B2 JP62153178A JP15317887A JP2547381B2 JP 2547381 B2 JP2547381 B2 JP 2547381B2 JP 62153178 A JP62153178 A JP 62153178A JP 15317887 A JP15317887 A JP 15317887A JP 2547381 B2 JP2547381 B2 JP 2547381B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- quaternary ammonium
- ammonium salt
- reaction vessel
- acrylic monomer
- 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 - Fee Related
Links
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 47
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 40
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 104
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 43
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000007789 gas Substances 0.000 claims abstract description 33
- 239000000178 monomer Substances 0.000 claims abstract description 31
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000001301 oxygen Substances 0.000 claims abstract description 22
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 22
- 239000011541 reaction mixture Substances 0.000 claims abstract description 20
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 13
- 239000003112 inhibitor Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 22
- 150000003839 salts Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 238000005660 chlorination reaction Methods 0.000 claims description 3
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 abstract description 27
- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 abstract description 10
- 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 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 4
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 abstract description 3
- 238000013459 approach Methods 0.000 abstract description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 100
- 229940050176 methyl chloride Drugs 0.000 description 49
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 7
- 229940073608 benzyl chloride Drugs 0.000 description 7
- 229960003505 mequinol Drugs 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 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 4
- 230000000052 comparative effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- -1 Methacryloyloxyethyltrimethylammonium Chloride Hydroquinone methyl ether Chemical compound 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- KBEAXUCAQWQPCW-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl-(2-phenylethyl)azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[NH2+]CCC1=CC=CC=C1 KBEAXUCAQWQPCW-UHFFFAOYSA-N 0.000 description 1
- WWJCRUKUIQRCGP-UHFFFAOYSA-N 3-(dimethylamino)propyl 2-methylprop-2-enoate Chemical compound CN(C)CCCOC(=O)C(C)=C WWJCRUKUIQRCGP-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
- FLCAEMBIQVZWIF-UHFFFAOYSA-N 6-(dimethylamino)-2-methylhex-2-enamide Chemical compound CN(C)CCCC=C(C)C(N)=O FLCAEMBIQVZWIF-UHFFFAOYSA-N 0.000 description 1
- 230000004931 aggregating effect Effects 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010908 decantation Methods 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
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229960004337 hydroquinone Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/876,602 US4745214A (en) | 1986-06-20 | 1986-06-20 | Process for the preparation of an aqueous solution of unsaturated quaternary ammonium salts |
| US876602 | 1997-06-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS635064A JPS635064A (ja) | 1988-01-11 |
| JP2547381B2 true JP2547381B2 (ja) | 1996-10-23 |
Family
ID=25368120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62153178A Expired - Fee Related JP2547381B2 (ja) | 1986-06-20 | 1987-06-19 | 不飽和第四アンモニウム塩水溶液の製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4745214A (en:Method) |
| EP (1) | EP0250325B1 (en:Method) |
| JP (1) | JP2547381B2 (en:Method) |
| AT (1) | ATE72228T1 (en:Method) |
| DE (1) | DE3776423D1 (en:Method) |
| ES (1) | ES2033333T3 (en:Method) |
| GR (1) | GR3004454T3 (en:Method) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07100683B2 (ja) * | 1987-02-18 | 1995-11-01 | 株式会社興人 | 不飽和第４級アンモニウム塩の製造方法 |
| US5260480A (en) * | 1988-02-11 | 1993-11-09 | Norsolor | Quaternization process |
| JP2773049B2 (ja) * | 1988-02-11 | 1998-07-09 | ノルソロール | 四級塩化方法 |
| FR2627181B1 (fr) * | 1988-02-11 | 1990-06-08 | Norsolor Sa | Procede de preparation de solutions aqueuses de sels insatures d'ammonium quaternaire |
| FR2642424B1 (fr) * | 1989-01-27 | 1991-09-27 | Norsolor Sa | Procede de preparation de solutions aqueuses de sels insatures d'ammonium quaternaire |
| JP2813602B2 (ja) * | 1989-01-31 | 1998-10-22 | 株式会社興人 | 保存性が改善されたｎ，ｎ―ジアルキルアミノアルキル（メタ）アクリルアミド組成物 |
| DE3990121T1 (de) * | 1989-02-02 | 1990-11-22 | Norsolor Sa | Quaternisationsverfahren |
| 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 |
| DE4243466A1 (de) * | 1992-12-22 | 1994-06-23 | Roehm Gmbh | Verfahren zur Herstellung von Trialkylammoniumalkyl(meth)acryl-Verbindungen |
| KR100367906B1 (ko) * | 1995-10-20 | 2003-03-04 | 삼성정밀화학 주식회사 | 알킬아크릴레이트4급암모늄염의제조방법 |
| FR2750696B1 (fr) * | 1996-07-08 | 1998-10-30 | Atochem Elf Sa | Solutions aqueuses stabilisees de sels d'ammoniums quaternaires insatures |
| KR100491098B1 (ko) * | 1997-10-15 | 2005-09-26 | 삼성정밀화학 주식회사 | 고순도 메타아크릴레이트 4급 암모늄염의 제조방법 |
| FR2788765B1 (fr) * | 1999-01-21 | 2001-03-02 | Atochem Elf Sa | Procede de fabrication de solutions aqueuses de sels insatures d'ammonium quaternaire |
| FR2788766B1 (fr) * | 1999-01-21 | 2001-03-02 | Atochem Elf Sa | Procede de fabrication de solutions aqueuses de sels insatures d'ammonium quaternaire |
| FR2788767B1 (fr) * | 1999-01-21 | 2001-03-02 | Atochem Elf Sa | Procede de fabrication de solutions aqueuses de sels insatures d'ammonium quaternaire |
| FR2804111B1 (fr) * | 2000-01-24 | 2003-01-03 | Atofina | Nouveaux monomeres a groupes amino quaternaire, leur procede de fabrication, et les nouveaux (co)polymeres obtenus a partir de ces nouveaux monomeres |
| US7049046B2 (en) * | 2004-03-30 | 2006-05-23 | Eastman Kodak Company | Infrared absorbing compounds and their use in imageable elements |
| FR2824061B1 (fr) | 2001-04-26 | 2004-03-05 | Atofina | Procede de fabrication du (meth) acrylate de 2-(dimethylamino)-1-(dimethylaminomethyl) ethyle |
| FR2824063B1 (fr) | 2001-04-26 | 2004-03-05 | Atofina | Procede de fabrication du chlorure de l'acrylate de 1,3-bis (dimethylbenzylammonium) isopropyle seul ou en melange d'autres monomeres et (co) polymers correspondant |
| FR2824062B1 (fr) | 2001-04-27 | 2004-10-15 | Atofina | Procede de fabrication de solutions aqueuses de sels insatures d'ammonium quaternaire |
| PL211454B1 (pl) | 2002-08-09 | 2012-05-31 | Akzo Nobel Coatings Int Bv | Polimer nierozpuszczalny w wodzie morskiej, sposób wytwarzania takiego polimeru oraz przeciwporostowa kompozycja powłokowa |
| US7973195B2 (en) * | 2009-07-22 | 2011-07-05 | Kemira Oyj | Process for unsaturated quaternary ammonium salt |
| CN115745813A (zh) * | 2022-10-26 | 2023-03-07 | 浙江海联新材料科技有限公司 | 一种甲基丙烯酰氧乙基二甲基苄基氯化铵溶液的制备方法 |
| CN115845785A (zh) * | 2022-12-29 | 2023-03-28 | 江苏富淼科技股份有限公司 | （甲基）丙烯酰氧乙基三甲基氯化铵的反应装置及其工艺 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB573175A (en) * | 1943-01-22 | 1945-11-09 | Ici Ltd | Improvements in or relating to the manufacture of unsaturated organic compounds |
| 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 |
-
1986
- 1986-06-20 US US06/876,602 patent/US4745214A/en not_active Expired - Lifetime
-
1987
- 1987-06-18 ES ES198787401373T patent/ES2033333T3/es not_active Expired - Lifetime
- 1987-06-18 DE DE8787401373T patent/DE3776423D1/de not_active Expired - Fee Related
- 1987-06-18 EP EP19870401373 patent/EP0250325B1/fr not_active Expired - Lifetime
- 1987-06-18 AT AT87401373T patent/ATE72228T1/de not_active IP Right Cessation
- 1987-06-19 JP JP62153178A patent/JP2547381B2/ja not_active Expired - Fee Related
-
1992
- 1992-04-23 GR GR920400816T patent/GR3004454T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE72228T1 (de) | 1992-02-15 |
| EP0250325B1 (fr) | 1992-01-29 |
| JPS635064A (ja) | 1988-01-11 |
| GR3004454T3 (en:Method) | 1993-03-31 |
| EP0250325A3 (en) | 1988-11-09 |
| DE3776423D1 (de) | 1992-03-12 |
| EP0250325A2 (fr) | 1987-12-23 |
| ES2033333T3 (es) | 1993-03-16 |
| US4745214A (en) | 1988-05-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |