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 (ja) |
| CN (1) | CN104203932A (ja) |
| MY (1) | MY167592A (ja) |
| PH (1) | PH12014501498B1 (ja) |
| WO (1) | WO2013122185A1 (ja) |
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 |
| JPWO2004002973A1 (ja) * | 2002-06-28 | 2005-10-27 | 株式会社カネカ | 光学活性１−置換アミノ−２，３−エポキシプロパンの製造方法並びにその合成中間体およびそれらの製造方法 |
| 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 |
| JP5103545B2 (ja) * | 2010-06-18 | 2012-12-19 | 花王株式会社 | アルキルグリシジルエーテルの製造方法 |
| 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 MY MYPI2014702266A patent/MY167592A/en unknown
- 2013-02-15 CN CN201380007756.2A patent/CN104203932A/zh active Pending
-
2014
- 2014-06-27 PH PH12014501498A patent/PH12014501498B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PH12014501498A1 (en) | 2014-10-08 |
| CN104203932A (zh) | 2014-12-10 |
| JP2013189425A (ja) | 2013-09-26 |
| JP6004962B2 (ja) | 2016-10-12 |
| WO2013122185A1 (ja) | 2013-08-22 |
| MY167592A (en) | 2018-09-20 |
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