DE2405933A1 - Verfahren zur herstellung niedermolekularer cycloaliphatischer diglycidylester - Google Patents
Verfahren zur herstellung niedermolekularer cycloaliphatischer diglycidylesterInfo
- Publication number
- DE2405933A1 DE2405933A1 DE19742405933 DE2405933A DE2405933A1 DE 2405933 A1 DE2405933 A1 DE 2405933A1 DE 19742405933 DE19742405933 DE 19742405933 DE 2405933 A DE2405933 A DE 2405933A DE 2405933 A1 DE2405933 A1 DE 2405933A1
- Authority
- DE
- Germany
- Prior art keywords
- cycloaliphatic
- low molecular
- water
- alkali
- diglycidylesters
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000002148 esters Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 9
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- -1 2,3-epoxypropyl carboxylic acid esters Chemical class 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 229910000318 alkali metal phosphate Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 2
- 238000010292 electrical insulation Methods 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 150000002924 oxiranes Chemical group 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical class OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- PMUPSYZVABJEKC-UHFFFAOYSA-N 1-methylcyclohexane-1,2-dicarboxylic acid Chemical class OC(=O)C1(C)CCCCC1C(O)=O PMUPSYZVABJEKC-UHFFFAOYSA-N 0.000 description 1
- MOBNLCPBAMKACS-UHFFFAOYSA-N 2-(1-chloroethyl)oxirane Chemical compound CC(Cl)C1CO1 MOBNLCPBAMKACS-UHFFFAOYSA-N 0.000 description 1
- HHCHLHOEAKKCAB-UHFFFAOYSA-N 2-oxaspiro[3.5]nonane-1,3-dione Chemical compound O=C1OC(=O)C11CCCCC1 HHCHLHOEAKKCAB-UHFFFAOYSA-N 0.000 description 1
- CJFPVLFGQIVQBD-UHFFFAOYSA-N 3-chloro-4-hydroxybutanoic acid Chemical class OCC(Cl)CC(O)=O CJFPVLFGQIVQBD-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- FFFPYJTVNSSLBQ-UHFFFAOYSA-N Phenolphthalin Chemical compound OC(=O)C1=CC=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 FFFPYJTVNSSLBQ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- XFUOBHWPTSIEOV-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohexane-1,2-dicarboxylate Chemical compound C1CCCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 XFUOBHWPTSIEOV-UHFFFAOYSA-N 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical class OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 235000019858 potassium salts of orthophosphoric acid Nutrition 0.000 description 1
- 239000011644 potassium salts of orthophosphoric acid Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011643 sodium salts of orthophosphoric acid Chemical group 0.000 description 1
- 235000019857 sodium salts of orthophosphoric acid Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 238000005406 washing 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
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Epoxy Resins (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742405933 DE2405933A1 (de) | 1974-02-08 | 1974-02-08 | Verfahren zur herstellung niedermolekularer cycloaliphatischer diglycidylester |
| US05/546,295 US3987070A (en) | 1974-02-08 | 1975-02-03 | Process for the production of low molecular weight cycloaliphatic diglycidyl esters |
| SE7501326A SE7501326L (en, 2012) | 1974-02-08 | 1975-02-06 | |
| JP50014915A JPS50108243A (en, 2012) | 1974-02-08 | 1975-02-06 | |
| AT91475A AT339328B (de) | 1974-02-08 | 1975-02-06 | Verfahren zur herstellung niedermolekularer cycloaliphatischer diglycidylester |
| BE153110A BE825247A (fr) | 1974-02-08 | 1975-02-06 | Procede de preparation d'esters diglycidyliques cycloaliphatiques a poids moleculaire inferieur |
| CA219,485A CA1035779A (en) | 1974-02-08 | 1975-02-06 | Process for the production of low molecular weight cycloaliphatic diglycidyl esters |
| IT48033/75A IT1029490B (it) | 1974-02-08 | 1975-02-06 | Procedimento per produrre esteri diglicidilici cicloalifatici di basso peso molecolare |
| FR7503940A FR2260582B1 (en, 2012) | 1974-02-08 | 1975-02-07 | |
| CH148475A CH597212A5 (en, 2012) | 1974-02-08 | 1975-02-07 | |
| NL7501500A NL7501500A (nl) | 1974-02-08 | 1975-02-07 | Werkwijze ter bereiding van kleinmoleculige alifatische diglycidylesters. |
| ES434548A ES434548A1 (es) | 1974-02-08 | 1975-02-07 | Procedimiento para preparar esteres de diglicidilo de aci- dos dicarboxilicos cicloalifaticos. |
| GB529275A GB1440745A (en) | 1974-02-08 | 1975-02-07 | Process for the production of low molecular weight cycloaliphatic diglycidyl esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742405933 DE2405933A1 (de) | 1974-02-08 | 1974-02-08 | Verfahren zur herstellung niedermolekularer cycloaliphatischer diglycidylester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2405933A1 true DE2405933A1 (de) | 1975-08-21 |
Family
ID=5906874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742405933 Pending DE2405933A1 (de) | 1974-02-08 | 1974-02-08 | Verfahren zur herstellung niedermolekularer cycloaliphatischer diglycidylester |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3987070A (en, 2012) |
| JP (1) | JPS50108243A (en, 2012) |
| AT (1) | AT339328B (en, 2012) |
| BE (1) | BE825247A (en, 2012) |
| CA (1) | CA1035779A (en, 2012) |
| CH (1) | CH597212A5 (en, 2012) |
| DE (1) | DE2405933A1 (en, 2012) |
| ES (1) | ES434548A1 (en, 2012) |
| FR (1) | FR2260582B1 (en, 2012) |
| GB (1) | GB1440745A (en, 2012) |
| IT (1) | IT1029490B (en, 2012) |
| NL (1) | NL7501500A (en, 2012) |
| SE (1) | SE7501326L (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU728536B2 (en) * | 1997-05-22 | 2001-01-11 | Shell Internationale Research Maatschappij B.V. | Glycidylester and thermosetting resin composition comprising the glycidylester |
| CN103857721A (zh) * | 2011-07-01 | 2014-06-11 | 陶氏环球技术有限责任公司 | 混杂的环氧树脂 |
-
1974
- 1974-02-08 DE DE19742405933 patent/DE2405933A1/de active Pending
-
1975
- 1975-02-03 US US05/546,295 patent/US3987070A/en not_active Expired - Lifetime
- 1975-02-06 CA CA219,485A patent/CA1035779A/en not_active Expired
- 1975-02-06 AT AT91475A patent/AT339328B/de not_active IP Right Cessation
- 1975-02-06 BE BE153110A patent/BE825247A/xx unknown
- 1975-02-06 JP JP50014915A patent/JPS50108243A/ja active Pending
- 1975-02-06 IT IT48033/75A patent/IT1029490B/it active
- 1975-02-06 SE SE7501326A patent/SE7501326L/xx unknown
- 1975-02-07 ES ES434548A patent/ES434548A1/es not_active Expired
- 1975-02-07 NL NL7501500A patent/NL7501500A/xx unknown
- 1975-02-07 FR FR7503940A patent/FR2260582B1/fr not_active Expired
- 1975-02-07 CH CH148475A patent/CH597212A5/xx not_active IP Right Cessation
- 1975-02-07 GB GB529275A patent/GB1440745A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50108243A (en, 2012) | 1975-08-26 |
| IT1029490B (it) | 1979-03-10 |
| USB546295I5 (en, 2012) | 1976-01-20 |
| CH597212A5 (en, 2012) | 1978-03-31 |
| BE825247A (fr) | 1975-08-06 |
| CA1035779A (en) | 1978-08-01 |
| GB1440745A (en) | 1976-06-23 |
| AT339328B (de) | 1977-10-10 |
| NL7501500A (nl) | 1975-08-12 |
| FR2260582B1 (en, 2012) | 1979-09-28 |
| FR2260582A1 (en, 2012) | 1975-09-05 |
| US3987070A (en) | 1976-10-19 |
| ES434548A1 (es) | 1976-12-16 |
| ATA91475A (de) | 1977-02-15 |
| SE7501326L (en, 2012) | 1975-08-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |