BR112012017631B1 - método de produção contínua de sais quaternários - Google Patents
método de produção contínua de sais quaternários Download PDFInfo
- Publication number
- BR112012017631B1 BR112012017631B1 BR112012017631A BR112012017631A BR112012017631B1 BR 112012017631 B1 BR112012017631 B1 BR 112012017631B1 BR 112012017631 A BR112012017631 A BR 112012017631A BR 112012017631 A BR112012017631 A BR 112012017631A BR 112012017631 B1 BR112012017631 B1 BR 112012017631B1
- Authority
- BR
- Brazil
- Prior art keywords
- cstr
- phase
- tas
- qap
- liquid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 35
- 238000010924 continuous production Methods 0.000 title claims description 15
- 150000003839 salts Chemical group 0.000 title claims description 8
- 239000012071 phase Substances 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 17
- 239000007789 gas Substances 0.000 claims description 14
- 239000003153 chemical reaction reagent Substances 0.000 claims description 13
- 238000000605 extraction Methods 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 5
- -1 chloride cetyl Chemical compound 0.000 claims description 4
- 150000003926 acrylamides Chemical class 0.000 claims description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 3
- 229940073608 benzyl chloride Drugs 0.000 claims description 3
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 230000000704 physical effect Effects 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 230000003113 alkalizing effect Effects 0.000 claims 11
- 238000004140 cleaning Methods 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 description 18
- 229940100198 alkylating agent Drugs 0.000 description 18
- 239000012535 impurity Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 239000012467 final product Substances 0.000 description 10
- 150000001412 amines Chemical group 0.000 description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 238000007086 side reaction Methods 0.000 description 6
- 238000009834 vaporization Methods 0.000 description 6
- 230000008016 vaporization Effects 0.000 description 6
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- 230000002152 alkylating effect Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003570 air Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YTLYLLTVENPWFT-UPHRSURJSA-N (Z)-3-aminoacrylic acid Chemical compound N\C=C/C(O)=O YTLYLLTVENPWFT-UPHRSURJSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N anhydrous methyl chloride Natural products ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004590 computer program Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012876 topography Methods 0.000 description 1
Classifications
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/18—Stationary reactors having moving elements inside
-
- 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
- C07C219/20—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 unsaturated
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 |
|---|---|---|---|
| US12/691,159 US8247597B2 (en) | 2010-01-21 | 2010-01-21 | Continuous production of DMAEA quaternary salts |
| PCT/US2011/021961 WO2011091197A2 (en) | 2010-01-21 | 2011-01-21 | Continuous production of quaternary salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112012017631A2 BR112012017631A2 (pt) | 2016-03-29 |
| BR112012017631B1 true BR112012017631B1 (pt) | 2018-10-09 |
Family
ID=44278027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112012017631A BR112012017631B1 (pt) | 2010-01-21 | 2011-01-21 | método de produção contínua de sais quaternários |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8247597B2 (enExample) |
| EP (1) | EP2526083B1 (enExample) |
| JP (1) | JP5916629B2 (enExample) |
| KR (1) | KR101782186B1 (enExample) |
| CN (2) | CN102712573A (enExample) |
| BR (1) | BR112012017631B1 (enExample) |
| CA (1) | CA2786744C (enExample) |
| ES (1) | ES2567081T3 (enExample) |
| MX (1) | MX2012008452A (enExample) |
| WO (1) | WO2011091197A2 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RS55996B1 (sr) | 2011-12-22 | 2017-09-29 | Cerbios-Pharma S A | Kontinuirani postupak za alkilaciju cikličnih tercijarnih amina |
| US9303360B2 (en) | 2013-08-08 | 2016-04-05 | Ecolab Usa Inc. | Use of nanocrystaline cellulose and polymer grafted nanocrystaline cellulose for increasing retention in papermaking process |
| US9034145B2 (en) | 2013-08-08 | 2015-05-19 | Ecolab Usa Inc. | Use of nanocrystaline cellulose and polymer grafted nanocrystaline cellulose for increasing retention, wet strength, and dry strength in papermaking process |
| US9410288B2 (en) | 2013-08-08 | 2016-08-09 | Ecolab Usa Inc. | Use of nanocrystaline cellulose and polymer grafted nanocrystaline cellulose for increasing retention in papermaking process |
| US9834730B2 (en) | 2014-01-23 | 2017-12-05 | Ecolab Usa Inc. | Use of emulsion polymers to flocculate solids in organic liquids |
| CN104744275A (zh) * | 2015-03-23 | 2015-07-01 | 浙江友联化学工业有限公司 | 一种季铵盐型阳离子单体水溶液的制备方法 |
| TR201909218T4 (tr) | 2015-04-17 | 2019-07-22 | Dow Agrosciences Llc | Pestisit işlevine sahip moleküller ve bunlarla ilişkili aramaddeler, bileşimler ve işlemler. |
| WO2017066540A1 (en) | 2015-10-15 | 2017-04-20 | Ecolab Usa Inc. | Nanocrystalline cellulose and polymer-grafted nanocrystalline cellulose as rheology modifying agents for magnesium oxide and lime slurries |
| CN110997593B (zh) | 2017-07-17 | 2023-01-24 | 埃科莱布美国股份有限公司 | 使浆料的流变性改性的方法 |
| 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 (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3244274A1 (de) * | 1982-11-30 | 1984-05-30 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung konzentrierter waessriger loesungen von quaternisierungsprodukten von tertiaeren aminoalkylestern oder tertiaeren aminoalkylamiden der acryl- oder methacrylsaeure |
| US5260480A (en) | 1988-02-11 | 1993-11-09 | Norsolor | Quaternization process |
| JPH03206067A (ja) * | 1990-01-08 | 1991-09-09 | Dai Ichi Kogyo Seiyaku Co Ltd | Ｎ，ｎ―ジアルキルアミノアルキル（メタ）アクリレート類の４級化方法 |
| JP2837279B2 (ja) * | 1990-12-20 | 1998-12-14 | 三井化学株式会社 | 不飽和第四級アンモニウム塩の製造法 |
| JPH07206790A (ja) | 1994-01-20 | 1995-08-08 | Mitsui Toatsu Chem Inc | 不飽和第四級アンモニウム塩の製造方法 |
| JPH08268985A (ja) * | 1995-03-29 | 1996-10-15 | Kohjin Co Ltd | 不飽和第４級アンモニウム塩の製造法 |
| FR2788767B1 (fr) | 1999-01-21 | 2001-03-02 | Atochem Elf Sa | Procede de fabrication de solutions aqueuses de sels insatures d'ammonium quaternaire |
| JP2000229919A (ja) * | 1999-02-12 | 2000-08-22 | Mitsubishi Rayon Co Ltd | 高純度不飽和第四級アンモニウム塩水溶液の製造方法 |
| US6423871B1 (en) * | 1999-02-26 | 2002-07-23 | University Of South Florida | Efficient synthesis of secondary amines by selective alkylation of primary amines |
| CN1276367A (zh) | 1999-06-05 | 2000-12-13 | 中国石化集团齐鲁石油化工公司 | 一种不饱和季铵盐的制备方法 |
| CN1126731C (zh) | 1999-11-17 | 2003-11-05 | 中国石化集团齐鲁石油化工公司 | 一种不饱和季铵盐的制备方法 |
| FR2824062B1 (fr) * | 2001-04-27 | 2004-10-15 | Atofina | Procede de fabrication de solutions aqueuses de sels insatures d'ammonium quaternaire |
| JP4178837B2 (ja) | 2002-05-29 | 2008-11-12 | 東亞合成株式会社 | ジアルキルアミノアルキル（メタ）アクリレート４級塩の製造方法 |
| JP2004010508A (ja) | 2002-06-04 | 2004-01-15 | Toagosei Co Ltd | ジアルキルアミノアルキル（メタ）アクリレート４級塩の製造方法 |
| JP4062055B2 (ja) | 2002-11-01 | 2008-03-19 | 東亞合成株式会社 | ジアルキルアミノアルキル（メタ）アクリレート４級塩の製造方法 |
| JP2008081443A (ja) | 2006-09-27 | 2008-04-10 | Toagosei Co Ltd | ジアルキルアミノアルキル（メタ）アクリレート４級塩の製造方法及びその製造装置 |
| WO2009090791A1 (ja) * | 2008-01-17 | 2009-07-23 | Toagosei Co., Ltd. | ジアルキルアミノアルキル（メタ）アクリレート４級塩の製造方法 |
| CN201424446Y (zh) | 2009-04-29 | 2010-03-17 | 北京恒聚化工集团有限责任公司 | 阳离子单体二甲胺基乙基丙烯酸脂氯甲烷季铵盐生产系统 |
| US7973195B2 (en) * | 2009-07-22 | 2011-07-05 | Kemira Oyj | Process for unsaturated quaternary ammonium salt |
-
2010
- 2010-01-21 US US12/691,159 patent/US8247597B2/en active Active
-
2011
- 2011-01-21 WO PCT/US2011/021961 patent/WO2011091197A2/en not_active Ceased
- 2011-01-21 MX MX2012008452A patent/MX2012008452A/es active IP Right Grant
- 2011-01-21 ES ES11735210.4T patent/ES2567081T3/es active Active
- 2011-01-21 JP JP2012550133A patent/JP5916629B2/ja active Active
- 2011-01-21 BR BR112012017631A patent/BR112012017631B1/pt active IP Right Grant
- 2011-01-21 CN CN2011800064883A patent/CN102712573A/zh active Pending
- 2011-01-21 KR KR1020127018533A patent/KR101782186B1/ko active Active
- 2011-01-21 EP EP11735210.4A patent/EP2526083B1/en active Active
- 2011-01-21 CN CN201610069204.XA patent/CN105646241A/zh active Pending
- 2011-01-21 CA CA2786744A patent/CA2786744C/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CA2786744A1 (en) | 2011-07-28 |
| WO2011091197A2 (en) | 2011-07-28 |
| ES2567081T3 (es) | 2016-04-19 |
| WO2011091197A3 (en) | 2011-12-29 |
| MX2012008452A (es) | 2012-08-15 |
| CN102712573A (zh) | 2012-10-03 |
| US20110178327A1 (en) | 2011-07-21 |
| CN105646241A (zh) | 2016-06-08 |
| EP2526083B1 (en) | 2016-03-23 |
| JP5916629B2 (ja) | 2016-05-11 |
| BR112012017631A2 (pt) | 2016-03-29 |
| JP2013518047A (ja) | 2013-05-20 |
| CA2786744C (en) | 2017-10-17 |
| EP2526083A4 (en) | 2013-12-25 |
| US8247597B2 (en) | 2012-08-21 |
| KR101782186B1 (ko) | 2017-09-26 |
| EP2526083A2 (en) | 2012-11-28 |
| KR20120116440A (ko) | 2012-10-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B06A | Patent application procedure suspended [chapter 6.1 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 21/01/2011, OBSERVADAS AS CONDICOES LEGAIS. |