DE2522745C2 - Verfahren zur Herstellung von Glycidäthern - Google Patents
Verfahren zur Herstellung von GlycidäthernInfo
- Publication number
- DE2522745C2 DE2522745C2 DE19752522745 DE2522745A DE2522745C2 DE 2522745 C2 DE2522745 C2 DE 2522745C2 DE 19752522745 DE19752522745 DE 19752522745 DE 2522745 A DE2522745 A DE 2522745A DE 2522745 C2 DE2522745 C2 DE 2522745C2
- Authority
- DE
- Germany
- Prior art keywords
- epichlorohydrin
- reaction
- stage
- epihalohydrin
- alkali
- 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 description 26
- 238000004519 manufacturing process Methods 0.000 title description 8
- 150000002170 ethers Chemical class 0.000 title description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 24
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 238000000926 separation method Methods 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 4
- 150000001447 alkali salts Chemical class 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 239000012266 salt solution Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 28
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- 239000000460 chlorine Substances 0.000 description 15
- 229910052801 chlorine Inorganic materials 0.000 description 13
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 11
- 235000002639 sodium chloride Nutrition 0.000 description 11
- 239000003513 alkali Substances 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000007792 addition Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- -1 epichlorohydrin Alkali hydroxide Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- XEPXTKKIWBPAEG-UHFFFAOYSA-N 1,1-dichloropropan-1-ol Chemical compound CCC(O)(Cl)Cl XEPXTKKIWBPAEG-UHFFFAOYSA-N 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007033 dehydrochlorination reaction Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 208000020442 loss of weight Diseases 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000010626 work up procedure Methods 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
- 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
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/063—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with epihalohydrins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH711874A CH593272A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-05-24 | 1974-05-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2522745A1 DE2522745A1 (de) | 1975-11-27 |
| DE2522745C2 true DE2522745C2 (de) | 1981-10-08 |
Family
ID=4320240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752522745 Expired DE2522745C2 (de) | 1974-05-24 | 1975-05-22 | Verfahren zur Herstellung von Glycidäthern |
Country Status (7)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR910001133B1 (ko) * | 1982-04-28 | 1991-02-25 | 스미또모 가까구 고교 가부시끼가이샤 | 1가 또는 다가 페놀의 글리시딜 에테르의 제조방법 |
| ATE511498T1 (de) | 2003-11-20 | 2011-06-15 | Solvay | Verfahren zur herstellung von dichlorpropanol aus glycerin und einem chlorinierungsmittel in anwesenheit von einem katalysator ausgewählt aus adipin- und glutarsaeure |
| WO2006106153A2 (fr) | 2005-05-20 | 2006-10-12 | Solvay (Société Anonyme) | Procede de fabrication d'une chlorhydrine par reaction entre un hydrocarbure aliphatique poly hydroxyle et un agent de chloration |
| KR20080019005A (ko) | 2005-05-20 | 2008-02-29 | 솔베이(소시에떼아노님) | 폴리히드록실화 지방족 탄화수소에서 출발하여클로로히드린을 제조하는 방법 |
| EA200970011A1 (ru) | 2006-06-14 | 2009-06-30 | Солвей (Сосьете Аноним) | Неочищенный продукт на основе глицерина, способ его очистки и его применение в производстве дихлорпропанола |
| FR2913421B1 (fr) | 2007-03-07 | 2009-05-15 | Solvay | Procede de fabrication de dichloropropanol. |
| FR2913684B1 (fr) | 2007-03-14 | 2012-09-14 | Solvay | Procede de fabrication de dichloropropanol |
| TW200911740A (en) | 2007-06-01 | 2009-03-16 | Solvay | Process for manufacturing a chlorohydrin |
| TWI500609B (zh) | 2007-06-12 | 2015-09-21 | Solvay | 含有環氧氯丙烷的產品，其製備及其不同應用中的用途 |
| TW200911693A (en) | 2007-06-12 | 2009-03-16 | Solvay | Aqueous composition containing a salt, manufacturing process and use |
| CN101896262A (zh) | 2007-10-02 | 2010-11-24 | 索尔维公司 | 含硅的组合物用于改进容器的抗腐蚀性的用途 |
| FR2925045B1 (fr) | 2007-12-17 | 2012-02-24 | Solvay | Produit a base de glycerol, procede pour son obtention et son utilisation dans la fabrication de dichloropropanol |
| TWI478875B (zh) | 2008-01-31 | 2015-04-01 | Solvay | 使水性組成物中之有機物質降解之方法 |
| US8507643B2 (en) | 2008-04-03 | 2013-08-13 | Solvay S.A. | Composition comprising glycerol, process for obtaining same and use thereof in the manufacture of dichloropropanol |
| FR2935968B1 (fr) | 2008-09-12 | 2010-09-10 | Solvay | Procede pour la purification de chlorure d'hydrogene |
| WO2011054770A1 (en) * | 2009-11-04 | 2011-05-12 | Solvay Sa | Process for manufacturing an epoxy resin |
| FR2954772B1 (fr) * | 2009-12-24 | 2012-12-28 | Solvay | Procede de fabrication d'une resine epoxy |
| WO2012041816A1 (en) | 2010-09-30 | 2012-04-05 | Solvay Sa | Derivative of epichlorohydrin of natural origin |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2841595A (en) * | 1955-01-31 | 1958-07-01 | Shell Dev | Process for manufacture of glycidyl ethers of polyhydric phenols |
| GB1050641A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1963-01-18 |
-
1974
- 1974-05-24 CH CH711874A patent/CH593272A5/xx not_active IP Right Cessation
-
1975
- 1975-04-28 GB GB1747275A patent/GB1493538A/en not_active Expired
- 1975-05-21 EG EG30375A patent/EG11717A/xx active
- 1975-05-22 FR FR7515973A patent/FR2272090B1/fr not_active Expired
- 1975-05-22 IT IT4971775A patent/IT1035822B/it active
- 1975-05-22 DE DE19752522745 patent/DE2522745C2/de not_active Expired
- 1975-05-23 BR BR7504159A patent/BR7503250A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1493538A (en) | 1977-11-30 |
| FR2272090A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-12-19 |
| IT1035822B (it) | 1979-10-20 |
| CH593272A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-11-30 |
| BR7503250A (pt) | 1976-04-27 |
| DE2522745A1 (de) | 1975-11-27 |
| FR2272090B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-09-22 |
| EG11717A (en) | 1977-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: INVENTA AG, 8006 ZUERICH, CH |
|
| 8330 | Complete disclaimer |