PH12014501498B1 - Method for producing epoxy compound - Google Patents
Method for producing epoxy compound Download PDFInfo
- Publication number
- PH12014501498B1 PH12014501498B1 PH12014501498A PH12014501498A PH12014501498B1 PH 12014501498 B1 PH12014501498 B1 PH 12014501498B1 PH 12014501498 A PH12014501498 A PH 12014501498A PH 12014501498 A PH12014501498 A PH 12014501498A PH 12014501498 B1 PH12014501498 B1 PH 12014501498B1
- Authority
- PH
- Philippines
- Prior art keywords
- epoxy compound
- mass
- reaction
- chlorohydrin
- producing
- Prior art date
Links
- 239000004593 Epoxy Substances 0.000 title claims abstract description 102
- 150000001875 compounds Chemical class 0.000 title claims abstract description 102
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 66
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 claims abstract description 97
- 239000003513 alkali Substances 0.000 claims abstract description 93
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 91
- -1 alkali metal salt Chemical class 0.000 claims abstract description 69
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 63
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 58
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 89
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 61
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 54
- 239000007864 aqueous solution Substances 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 48
- 239000012528 membrane Substances 0.000 claims description 36
- 239000000243 solution Substances 0.000 claims description 31
- 239000011780 sodium chloride Substances 0.000 claims description 27
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 14
- 238000005868 electrolysis reaction Methods 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- 239000001103 potassium chloride Substances 0.000 claims description 9
- 235000011164 potassium chloride Nutrition 0.000 claims description 9
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims description 6
- 239000003014 ion exchange membrane Substances 0.000 claims description 6
- 150000008044 alkali metal hydroxides Chemical group 0.000 claims description 4
- 150000001805 chlorine compounds Chemical group 0.000 claims description 2
- 101100243022 Mus musculus Pcnt gene Proteins 0.000 abstract 2
- 230000000052 comparative effect Effects 0.000 description 24
- 238000000034 method Methods 0.000 description 23
- 239000007795 chemical reaction product Substances 0.000 description 20
- HBIDQESLANDBPJ-UHFFFAOYSA-N 3-pentan-2-yloxypropane-1,2-diol Chemical compound CCCC(C)OCC(O)CO HBIDQESLANDBPJ-UHFFFAOYSA-N 0.000 description 17
- 239000002994 raw material Substances 0.000 description 16
- NCZPCONIKBICGS-UHFFFAOYSA-N 3-(2-ethylhexoxy)propane-1,2-diol Chemical compound CCCCC(CC)COCC(O)CO NCZPCONIKBICGS-UHFFFAOYSA-N 0.000 description 14
- 239000003011 anion exchange membrane Substances 0.000 description 14
- 238000005341 cation exchange Methods 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- QGJIHMFIXIWYAY-UHFFFAOYSA-N 2-(pentan-2-yloxymethyl)oxirane Chemical compound CCCC(C)OCC1CO1 QGJIHMFIXIWYAY-UHFFFAOYSA-N 0.000 description 11
- 239000006227 byproduct Substances 0.000 description 11
- 230000007062 hydrolysis Effects 0.000 description 11
- 238000006460 hydrolysis reaction Methods 0.000 description 11
- 238000000926 separation method Methods 0.000 description 10
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000011521 glass Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- MXXYMDQZEAUJPT-UHFFFAOYSA-N 1-chloro-4-(1-chloro-5-ethyl-2-hydroxynonan-4-yl)oxy-5-ethylnonan-2-ol Chemical compound ClCC(CC(C(CCCC)CC)OC(C(CCCC)CC)CC(CCl)O)O MXXYMDQZEAUJPT-UHFFFAOYSA-N 0.000 description 6
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000003792 electrolyte Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XRHGOQVKTMDFAB-UHFFFAOYSA-N 1-chloro-3-(8-methylnonoxy)propan-2-ol Chemical compound ClCC(COCCCCCCCC(C)C)O XRHGOQVKTMDFAB-UHFFFAOYSA-N 0.000 description 4
- YIEWJUDIKXQGKF-UHFFFAOYSA-N 1-chloro-3-decoxypropan-2-ol Chemical compound CCCCCCCCCCOCC(O)CCl YIEWJUDIKXQGKF-UHFFFAOYSA-N 0.000 description 4
- BYAAUZDTUKVBDS-UHFFFAOYSA-N 1-chloro-3-dodecoxypropan-2-ol Chemical compound CCCCCCCCCCCCOCC(O)CCl BYAAUZDTUKVBDS-UHFFFAOYSA-N 0.000 description 4
- DNZUNVIOUMBUHF-UHFFFAOYSA-N 1-chloro-3-hexoxypropan-2-ol Chemical compound CCCCCCOCC(O)CCl DNZUNVIOUMBUHF-UHFFFAOYSA-N 0.000 description 4
- RONHEAQGRBGOCO-UHFFFAOYSA-N 1-chloro-3-pentoxypropan-2-ol Chemical compound CCCCCOCC(O)CCl RONHEAQGRBGOCO-UHFFFAOYSA-N 0.000 description 4
- 238000007599 discharging Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- LLABJEIITAMJKJ-UHFFFAOYSA-N 1-chloro-3-octoxypropan-2-ol Chemical compound CCCCCCCCOCC(O)CCl LLABJEIITAMJKJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 3
- 229910017053 inorganic salt Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000004065 wastewater treatment Methods 0.000 description 3
- IZHGMMBZJWHGND-UHFFFAOYSA-N 1-butoxy-3-chloropropan-2-ol Chemical compound CCCCOCC(O)CCl IZHGMMBZJWHGND-UHFFFAOYSA-N 0.000 description 2
- KAZQUWDPQHMZIY-UHFFFAOYSA-N 1-chloro-3-pentan-2-yloxypropan-2-ol Chemical compound ClCC(COC(C)CCC)O KAZQUWDPQHMZIY-UHFFFAOYSA-N 0.000 description 2
- HCTDRZMGZRHFJV-UHFFFAOYSA-N 1-chloro-3-phenoxypropan-2-ol Chemical compound ClCC(O)COC1=CC=CC=C1 HCTDRZMGZRHFJV-UHFFFAOYSA-N 0.000 description 2
- XSQINWRJMQOTIV-UHFFFAOYSA-N 1-chloro-4-(1-chloro-2-hydroxy-5-methylheptan-4-yl)oxy-5-methylheptan-2-ol Chemical compound ClCC(CC(C(CC)C)OC(C(CC)C)CC(CCl)O)O XSQINWRJMQOTIV-UHFFFAOYSA-N 0.000 description 2
- MXTOERJFDQFGEM-UHFFFAOYSA-N 1-chloro-4-(1-chloro-2-hydroxy-5-methyloctan-4-yl)oxy-5-methyloctan-2-ol Chemical compound ClCC(CC(C(CCC)C)OC(C(CCC)C)CC(CCl)O)O MXTOERJFDQFGEM-UHFFFAOYSA-N 0.000 description 2
- NKRXGUMTFKQZRZ-UHFFFAOYSA-N 1-chloro-4-(1-chloro-2-hydroxy-5-methylundecan-4-yl)oxy-5-methylundecan-2-ol Chemical compound ClCC(CC(C(CCCCCC)C)OC(C(CCCCCC)C)CC(CCl)O)O NKRXGUMTFKQZRZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- IQCASZIDTNHBIW-UHFFFAOYSA-N 2-(pentoxymethyl)oxirane Chemical compound CCCCCOCC1CO1 IQCASZIDTNHBIW-UHFFFAOYSA-N 0.000 description 1
- 235000008375 Decussocarpus nagi Nutrition 0.000 description 1
- 244000309456 Decussocarpus nagi Species 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 206010027977 Morose Diseases 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000909 electrodialysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000012358 sourcing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/27—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms
- C07D301/28—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms by reaction with hydroxyl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012031266 | 2012-02-16 | ||
| PCT/JP2013/053652 WO2013122185A1 (ja) | 2012-02-16 | 2013-02-15 | エポキシ化合物の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PH12014501498A1 PH12014501498A1 (en) | 2014-10-08 |
| PH12014501498B1 true PH12014501498B1 (en) | 2014-10-08 |
Family
ID=48984294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH12014501498A PH12014501498B1 (en) | 2012-02-16 | 2014-06-27 | Method for producing epoxy compound |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP6004962B2 (enrdf_load_stackoverflow) |
| CN (1) | CN104203932A (enrdf_load_stackoverflow) |
| MY (1) | MY167592A (enrdf_load_stackoverflow) |
| PH (1) | PH12014501498B1 (enrdf_load_stackoverflow) |
| WO (1) | WO2013122185A1 (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108928895A (zh) * | 2018-08-13 | 2018-12-04 | 浙江迪萧环保科技有限公司 | 一种邻位双卤代羧酸的双极膜电渗析环化方法 |
| CN115925653B (zh) * | 2022-09-27 | 2024-05-24 | 江苏三木化工股份有限公司 | 一种环氧活性稀释剂邻甲酚缩水甘油醚的合成方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01265044A (ja) * | 1988-04-18 | 1989-10-23 | Idemitsu Kosan Co Ltd | 新規４，６−ジメチル−１−ヘプテン誘導体およびその製造法 |
| JPH0699411B2 (ja) * | 1989-02-22 | 1994-12-07 | ダイソー株式会社 | 液晶性化合物及び用途 |
| JP2894134B2 (ja) * | 1993-01-14 | 1999-05-24 | ダイソー株式会社 | 光学活性エピクロルヒドリンの製造法 |
| JPH10251196A (ja) * | 1997-03-07 | 1998-09-22 | Hamari Yakuhin Kogyo Kk | 光学活性３−ヒドロキシ脂肪酸の合成法 |
| JP4651178B2 (ja) * | 2000-10-23 | 2011-03-16 | 三菱レイヨン株式会社 | ２−グリシジルオキシエチル（メタ）アクリレートの製造方法 |
| JP2002293755A (ja) * | 2001-03-30 | 2002-10-09 | Yokkaichi Chem Co Ltd | β−アルキルハロヒドリンエーテルの製造方法 |
| EP1553093A1 (en) * | 2002-06-28 | 2005-07-13 | Kaneka Corporation | Process for preparation of optically active 1-substituted amino-2,3-epoxypropanes, intermediates for the synthesis thereof and process for preparation of the intermediates |
| JP4540442B2 (ja) * | 2004-10-14 | 2010-09-08 | 花王株式会社 | グリシジルエーテルの製造方法 |
| FR2887873A1 (fr) * | 2005-06-30 | 2007-01-05 | Rhodia Chimie Sa | PROCEDE DE PREPARATION D'UN ALCYNE PRESENTANT UN GROUPE HYDROXYLE OPTIQUEMENT ACTIF EN POSITION b OU g D'UNE TRIPLE LIAISON ET PRODUITS INTERMEDIAIRES OBTENUS |
| JP2007297330A (ja) * | 2006-04-28 | 2007-11-15 | Daiso Co Ltd | ２−メチルグリシジル誘導体の製造法 |
| US20100032617A1 (en) * | 2007-02-20 | 2010-02-11 | Solvay (Societe Anonyme) | Process for manufacturing epichlorohydrin |
| JP2009184943A (ja) * | 2008-02-05 | 2009-08-20 | Daiso Co Ltd | エピクロロヒドリンの製造方法 |
| AT507260B1 (de) * | 2008-08-25 | 2010-10-15 | Kanzler Walter | Verfahren zur herstellung von epichlorhydrin aus glyzerin |
| JP2010143890A (ja) * | 2008-12-22 | 2010-07-01 | Kao Corp | エポキシ化合物の製造方法 |
| PH12012502342A1 (en) * | 2010-06-18 | 2017-01-27 | Kao Corp | Method for producing alkylglycidyl ether |
| CN102304723A (zh) * | 2011-09-20 | 2012-01-04 | 福建师范大学 | 一种基于阴阳离子交换膜与双极膜构成的三膜四室无氯产碱电解槽 |
-
2013
- 2013-02-14 JP JP2013026885A patent/JP6004962B2/ja active Active
- 2013-02-15 WO PCT/JP2013/053652 patent/WO2013122185A1/ja active Application Filing
- 2013-02-15 CN CN201380007756.2A patent/CN104203932A/zh active Pending
- 2013-02-15 MY MYPI2014702266A patent/MY167592A/en unknown
-
2014
- 2014-06-27 PH PH12014501498A patent/PH12014501498B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP6004962B2 (ja) | 2016-10-12 |
| PH12014501498A1 (en) | 2014-10-08 |
| JP2013189425A (ja) | 2013-09-26 |
| CN104203932A (zh) | 2014-12-10 |
| MY167592A (en) | 2018-09-20 |
| WO2013122185A1 (ja) | 2013-08-22 |
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