DE2260451A1 - Verfahren zur reinigung von verunreinigten alpha,alpha-disubstituierten beta-propiolactonen - Google Patents
Verfahren zur reinigung von verunreinigten alpha,alpha-disubstituierten beta-propiolactonenInfo
- Publication number
- DE2260451A1 DE2260451A1 DE2260451A DE2260451A DE2260451A1 DE 2260451 A1 DE2260451 A1 DE 2260451A1 DE 2260451 A DE2260451 A DE 2260451A DE 2260451 A DE2260451 A DE 2260451A DE 2260451 A1 DE2260451 A1 DE 2260451A1
- Authority
- DE
- Germany
- Prior art keywords
- aluminum
- propiolactone
- trialkyl
- purified
- carbon atoms
- 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 28
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical class O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 title claims description 15
- 238000004140 cleaning Methods 0.000 title description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 44
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 43
- 238000006116 polymerization reaction Methods 0.000 claims description 32
- 229960000380 propiolactone Drugs 0.000 claims description 16
- ULKFLOVGORAZDI-UHFFFAOYSA-N 3,3-dimethyloxetan-2-one Chemical compound CC1(C)COC1=O ULKFLOVGORAZDI-UHFFFAOYSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000002596 lactones Chemical class 0.000 claims description 10
- 238000000746 purification Methods 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical group C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 2
- 238000005292 vacuum distillation Methods 0.000 claims description 2
- 239000000178 monomer Substances 0.000 description 35
- 229920000642 polymer Polymers 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002518 antifoaming agent Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- -1 alkyl vinyl ethers Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WFSNNQAIZHNZGH-UHFFFAOYSA-N 2,4-diethyl-2-(hydroxymethyl)octanoic acid Chemical compound C(C)C(CC(C(=O)O)(CO)CC)CCCC WFSNNQAIZHNZGH-UHFFFAOYSA-N 0.000 description 1
- XSEPYPDPHNTXBX-UHFFFAOYSA-N 2-(hydroxymethyl)-2-methylbutanoic acid Chemical compound CCC(C)(CO)C(O)=O XSEPYPDPHNTXBX-UHFFFAOYSA-N 0.000 description 1
- ISSYFABJJSOCQG-UHFFFAOYSA-N 3-hydroxy-2-methyl-2-phenylpropanoic acid Chemical compound OCC(C)(C(O)=O)C1=CC=CC=C1 ISSYFABJJSOCQG-UHFFFAOYSA-N 0.000 description 1
- 101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000003180 beta-lactone group Chemical group 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 150000004950 naphthalene Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase 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
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Pyrane Compounds (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00208906A US3825573A (en) | 1971-12-16 | 1971-12-16 | Purification of alpha,alpha-disubstituted-beta-propiolactones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2260451A1 true DE2260451A1 (de) | 1973-06-20 |
Family
ID=22776539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2260451A Pending DE2260451A1 (de) | 1971-12-16 | 1972-12-11 | Verfahren zur reinigung von verunreinigten alpha,alpha-disubstituierten beta-propiolactonen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3825573A (Direct) |
| JP (1) | JPS4867267A (Direct) |
| CA (1) | CA982978A (Direct) |
| DE (1) | DE2260451A1 (Direct) |
| FR (1) | FR2163601B1 (Direct) |
| GB (1) | GB1385806A (Direct) |
-
1971
- 1971-12-16 US US00208906A patent/US3825573A/en not_active Expired - Lifetime
-
1972
- 1972-11-08 CA CA155,945A patent/CA982978A/en not_active Expired
- 1972-12-11 DE DE2260451A patent/DE2260451A1/de active Pending
- 1972-12-14 GB GB5787772A patent/GB1385806A/en not_active Expired
- 1972-12-14 FR FR7244475A patent/FR2163601B1/fr not_active Expired
- 1972-12-16 JP JP47126671A patent/JPS4867267A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA982978A (en) | 1976-02-03 |
| US3825573A (en) | 1974-07-23 |
| FR2163601A1 (Direct) | 1973-07-27 |
| GB1385806A (en) | 1975-02-26 |
| FR2163601B1 (Direct) | 1976-08-20 |
| JPS4867267A (Direct) | 1973-09-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1520874B1 (de) | Verfahren zur Herstellung eines Polyesters | |
| DE2804449C2 (de) | Verfahren zum Inhibieren der Polymerisation einer leicht polymerisierbaren aromatischen Vinylverbindung | |
| DE1223551B (de) | Verfahren zur Herstellung von veresterten hochmolekularen Polyoxymethylenen | |
| DE1495656B2 (Direct) | ||
| DE1230219B (de) | Initiatoren bei der Polymerisation von praktisch wasserfreiem monomerem Formaldehyd | |
| DE2260451A1 (de) | Verfahren zur reinigung von verunreinigten alpha,alpha-disubstituierten beta-propiolactonen | |
| DE1215134B (de) | Stabilisierung von Vinylchlorid zur Verhinderung der Polymerisation | |
| DE814739C (de) | Verfahren zur Reinigung synthetischer Aldehydprodukte | |
| DE1147385B (de) | Verfahren zur Herstellung von Polymerisaten oder Copolymerisaten von Aldehyden | |
| DE1520874C (de) | Verfahren zur Herstellung eines Polyesters | |
| DE875804C (de) | Verfahren zur Herstellung von Umwandlungsprodukten des Pentaerythrit-dichlorhydrin-monoschwefligsaeureesters | |
| DE1248938B (de) | Verfahren zur Herstellung kristalliner Acetaldehydpolymerisate | |
| AT232722B (de) | Verfahren zur Reinigung von Polymeren | |
| DE1037127B (de) | Katalysatoren zur Polymerisation von Formaldehyd | |
| DE2216168A1 (Direct) | ||
| DE715268C (de) | Verfahren zur Herstellung von Vinylaethern aus Acetylen und Oxyverbindungen | |
| AT218741B (de) | Verfahren zur Aufarbeitung von kontakthaltigen Olefinpolymerisaten | |
| DE1620971C (de) | Verfahren zur Herstellung von Poly furoxanen | |
| US2294346A (en) | Purification of fusel oil and amyl alcohol | |
| DE1795028C3 (de) | Verfahren zum Stabilisieren von rohem Polyoxymethylen | |
| DE1618886C (de) | Verfahren zur Stabilisierung von alpha, alpha Dimethyl beta propiolacton | |
| DE863417C (de) | Verfahren zur kontinuierlichen Herstellung von Polymeren oder von Kondensations- oder Dehydratationsprodukten | |
| DE1520945C (de) | Verfahren zur Herstellung von Poly propylen | |
| DE946187C (de) | Verfahren zum Polymerisieren von Alkylcyclosiloxanen | |
| DE848952C (de) | Verfahren zur Herstellung von organischen Verbindungen |