DE2308120A1 - Verfahren zur herstellung von cyanalkylepoxyaethern und zur stabilisierung von glycid und glycid-artigen verbindungen - Google Patents
Verfahren zur herstellung von cyanalkylepoxyaethern und zur stabilisierung von glycid und glycid-artigen verbindungenInfo
- Publication number
- DE2308120A1 DE2308120A1 DE19732308120 DE2308120A DE2308120A1 DE 2308120 A1 DE2308120 A1 DE 2308120A1 DE 19732308120 DE19732308120 DE 19732308120 DE 2308120 A DE2308120 A DE 2308120A DE 2308120 A1 DE2308120 A1 DE 2308120A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- compound
- compounds
- glycide
- general formula
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 21
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title description 4
- 230000006641 stabilisation Effects 0.000 title description 3
- 238000011105 stabilization Methods 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims description 21
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 17
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 150000007530 organic bases Chemical class 0.000 claims description 9
- 239000003957 anion exchange resin Substances 0.000 claims description 8
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- -1 cyano compound Chemical class 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 5
- 229920001429 chelating resin Polymers 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052753 mercury Inorganic materials 0.000 claims description 4
- 229920001467 poly(styrenesulfonates) Polymers 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 description 10
- 150000002170 ethers Chemical class 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 5
- 125000004966 cyanoalkyl group Chemical group 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 238000007265 chloromethylation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000003822 preparative gas chromatography Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 229920003060 Poly(vinyl benzyl chloride) Polymers 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- RYCNBIYTZSGSPI-UHFFFAOYSA-N ditert-butyl benzene-1,2-dicarboxylate Chemical compound CC(C)(C)OC(=O)C1=CC=CC=C1C(=O)OC(C)(C)C RYCNBIYTZSGSPI-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 239000011049 pearl Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000003643 water by type 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22759772A | 1972-02-18 | 1972-02-18 | |
| US00227598A US3819662A (en) | 1972-02-18 | 1972-02-18 | Method for stabilizing glycidol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2308120A1 true DE2308120A1 (de) | 1973-08-23 |
Family
ID=26921575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732308120 Pending DE2308120A1 (de) | 1972-02-18 | 1973-02-19 | Verfahren zur herstellung von cyanalkylepoxyaethern und zur stabilisierung von glycid und glycid-artigen verbindungen |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4886820A (enrdf_load_stackoverflow) |
| BE (1) | BE795579A (enrdf_load_stackoverflow) |
| DE (1) | DE2308120A1 (enrdf_load_stackoverflow) |
| FR (2) | FR2172287B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1419142A (enrdf_load_stackoverflow) |
| IT (1) | IT977814B (enrdf_load_stackoverflow) |
| NL (1) | NL7302237A (enrdf_load_stackoverflow) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1252717A (enrdf_load_stackoverflow) * | 1969-02-28 | 1971-11-10 |
-
0
- BE BE795579D patent/BE795579A/xx unknown
-
1973
- 1973-02-15 GB GB749373A patent/GB1419142A/en not_active Expired
- 1973-02-15 FR FR7305367A patent/FR2172287B1/fr not_active Expired
- 1973-02-16 IT IT6738373A patent/IT977814B/it active
- 1973-02-16 NL NL7302237A patent/NL7302237A/xx not_active Application Discontinuation
- 1973-02-19 DE DE19732308120 patent/DE2308120A1/de active Pending
- 1973-02-19 JP JP2007373A patent/JPS4886820A/ja active Pending
- 1973-07-25 FR FR7327268A patent/FR2202087B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7302237A (enrdf_load_stackoverflow) | 1973-08-21 |
| BE795579A (fr) | 1973-08-16 |
| GB1419142A (en) | 1975-12-24 |
| JPS4886820A (enrdf_load_stackoverflow) | 1973-11-15 |
| FR2202087A1 (enrdf_load_stackoverflow) | 1974-05-03 |
| FR2172287A1 (enrdf_load_stackoverflow) | 1973-09-28 |
| FR2202087B1 (enrdf_load_stackoverflow) | 1977-07-01 |
| FR2172287B1 (enrdf_load_stackoverflow) | 1976-06-11 |
| IT977814B (it) | 1974-09-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |