CA1067911A - Procede de preparation de monomeres acryliques destines a la fabrication de floculants cationiques - Google Patents
Procede de preparation de monomeres acryliques destines a la fabrication de floculants cationiquesInfo
- Publication number
- CA1067911A CA1067911A CA233,666A CA233666A CA1067911A CA 1067911 A CA1067911 A CA 1067911A CA 233666 A CA233666 A CA 233666A CA 1067911 A CA1067911 A CA 1067911A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- water
- solvent
- salt
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 36
- 239000000178 monomer Substances 0.000 title claims abstract description 19
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000002904 solvent Substances 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000007864 aqueous solution Substances 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 239000000243 solution Substances 0.000 claims abstract description 16
- 239000012535 impurity Substances 0.000 claims abstract description 14
- 239000008346 aqueous phase Substances 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 229920000642 polymer Polymers 0.000 claims abstract description 10
- -1 acrylic ester Chemical class 0.000 claims abstract description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract description 6
- 239000012074 organic phase Substances 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims abstract description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 238000005956 quaternization reaction Methods 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 229920001519 homopolymer Polymers 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001805 chlorine compounds Chemical group 0.000 claims description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000008394 flocculating agent Substances 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 239000012071 phase Substances 0.000 claims description 2
- 239000012047 saturated solution Substances 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 10
- 238000005406 washing Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- 229940050176 methyl chloride Drugs 0.000 description 5
- 239000012736 aqueous medium Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000002609 medium Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- SSONCJTVDRSLNK-UHFFFAOYSA-N 2-methylprop-2-enoic acid;hydrochloride Chemical compound Cl.CC(=C)C(O)=O SSONCJTVDRSLNK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- HJPOKQICBCJGHE-UHFFFAOYSA-J [C+4].[Cl-].[Cl-].[Cl-].[Cl-] Chemical compound [C+4].[Cl-].[Cl-].[Cl-].[Cl-] HJPOKQICBCJGHE-UHFFFAOYSA-J 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical class COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7429460A FR2282422A1 (fr) | 1974-08-23 | 1974-08-23 | Procede de preparation de monomeres acryliques destines a la fabrication de floculants cationiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1067911A true CA1067911A (fr) | 1979-12-11 |
Family
ID=9142647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA233,666A Expired CA1067911A (fr) | 1974-08-23 | 1975-08-18 | Procede de preparation de monomeres acryliques destines a la fabrication de floculants cationiques |
Country Status (14)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5217417A (en) * | 1975-07-31 | 1977-02-09 | Sanyo Chem Ind Ltd | Process for removal of compound to cause abnormal polymerization |
| JPS52148017A (en) * | 1976-05-31 | 1977-12-08 | Nitto Chem Ind Co Ltd | Preparation of unsaturated quaternary ammonium salt |
| JPS52148018A (en) * | 1976-05-31 | 1977-12-08 | Nitto Chem Ind Co Ltd | Preparation of unsaturated quaternary ammonium salt |
| DE2848627C2 (de) | 1978-11-09 | 1982-02-04 | Röhm GmbH, 6100 Darmstadt | Verfahren zur Herstellung eines flüssigen, unmittelbar polymerisierbaren Gemisches aus Acrylamid und Quaternierungsprodukten von tertiären Aminoalkylestern oder tertiären Aminoalkylamiden der Acryl- oder Methacrylsäure |
| JPS5584703U (enrdf_load_stackoverflow) * | 1978-11-30 | 1980-06-11 | ||
| JPS5584701U (enrdf_load_stackoverflow) * | 1978-11-30 | 1980-06-11 | ||
| JPS5656002U (enrdf_load_stackoverflow) * | 1979-10-03 | 1981-05-15 | ||
| 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 |
| US5631003A (en) * | 1991-09-25 | 1997-05-20 | Henkel Kommanditgesellschaft Auf Aktien | Hair treatment prepartation |
| DE19620036C2 (de) * | 1996-05-17 | 1998-03-12 | Roehm Gmbh | Gewinnung von wasserfreiem 2-Trimethylammoniumethylmethacrylatchlorid aus wäßriger Lösung |
-
1974
- 1974-08-23 FR FR7429460A patent/FR2282422A1/fr active Granted
-
1975
- 1975-06-25 IL IL47566A patent/IL47566A/xx unknown
- 1975-07-16 GB GB2990175A patent/GB1459811A/en not_active Expired
- 1975-07-31 IT IT50776/75A patent/IT1041109B/it active
- 1975-07-31 AT AT595575A patent/AT340378B/de not_active IP Right Cessation
- 1975-08-12 NL NL7509607A patent/NL7509607A/xx not_active Application Discontinuation
- 1975-08-14 AR AR260010A patent/AR210862A1/es active
- 1975-08-15 SE SE7509169A patent/SE7509169L/xx unknown
- 1975-08-18 CA CA233,666A patent/CA1067911A/fr not_active Expired
- 1975-08-21 BR BR7505373*A patent/BR7505373A/pt unknown
- 1975-08-21 DD DD187971A patent/DD122074A5/xx unknown
- 1975-08-21 DK DK376175A patent/DK376175A/da unknown
- 1975-08-22 JP JP10199875A patent/JPS5346824B2/ja not_active Expired
- 1975-08-22 DE DE19752537378 patent/DE2537378B2/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5346824B2 (enrdf_load_stackoverflow) | 1978-12-16 |
| JPS5143712A (enrdf_load_stackoverflow) | 1976-04-14 |
| IL47566A (en) | 1979-01-31 |
| IT1041109B (it) | 1980-01-10 |
| GB1459811A (en) | 1976-12-31 |
| DD122074A5 (de) | 1976-09-12 |
| DE2537378B2 (de) | 1978-01-19 |
| BR7505373A (pt) | 1976-08-03 |
| ATA595575A (de) | 1977-04-15 |
| SE7509169L (sv) | 1976-02-24 |
| NL7509607A (nl) | 1976-02-25 |
| FR2282422A1 (fr) | 1976-03-19 |
| IL47566A0 (en) | 1975-08-31 |
| DK376175A (da) | 1976-02-24 |
| AR210862A1 (es) | 1977-09-30 |
| AT340378B (de) | 1977-12-12 |
| DE2537378A1 (de) | 1976-03-04 |
| FR2282422B1 (enrdf_load_stackoverflow) | 1977-03-25 |
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