DE3933617C2 - - Google Patents
Info
- Publication number
- DE3933617C2 DE3933617C2 DE3933617A DE3933617A DE3933617C2 DE 3933617 C2 DE3933617 C2 DE 3933617C2 DE 3933617 A DE3933617 A DE 3933617A DE 3933617 A DE3933617 A DE 3933617A DE 3933617 C2 DE3933617 C2 DE 3933617C2
- Authority
- DE
- Germany
- Prior art keywords
- tin
- carbonic acid
- enyl
- general formula
- catalyst
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- -1 cyclic carbonic acid esters Chemical class 0.000 claims description 18
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
- 150000004651 carbonic acid esters Chemical class 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 6
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000002009 diols Chemical class 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 238000004508 fractional distillation Methods 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 150000005676 cyclic carbonates Chemical class 0.000 abstract description 3
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229940035437 1,3-propanediol Drugs 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Substances [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 229920002988 biodegradable polymer Polymers 0.000 description 2
- 239000004621 biodegradable polymer Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 2
- ZSUXOVNWDZTCFN-UHFFFAOYSA-L tin(ii) bromide Chemical compound Br[Sn]Br ZSUXOVNWDZTCFN-UHFFFAOYSA-L 0.000 description 2
- YXTDAZMTQFUZHK-ZVGUSBNCSA-L (2r,3r)-2,3-dihydroxybutanedioate;tin(2+) Chemical compound [Sn+2].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O YXTDAZMTQFUZHK-ZVGUSBNCSA-L 0.000 description 1
- UJGHGRGFKZWGMS-UHFFFAOYSA-N 1,3-dioxan-2-one Chemical compound O=C1OCCCO1.O=C1OCCCO1 UJGHGRGFKZWGMS-UHFFFAOYSA-N 0.000 description 1
- HFSKWPUHEMGYMQ-UHFFFAOYSA-N 1,3-dioxolan-2-one Chemical compound O=C1OCCO1.O=C1OCCO1 HFSKWPUHEMGYMQ-UHFFFAOYSA-N 0.000 description 1
- NGCDGPPKVSZGRR-UHFFFAOYSA-J 1,4,6,9-tetraoxa-5-stannaspiro[4.4]nonane-2,3,7,8-tetrone Chemical compound [Sn+4].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O NGCDGPPKVSZGRR-UHFFFAOYSA-J 0.000 description 1
- SKEZDZQGPKHHSH-UHFFFAOYSA-J 2-hydroxypropanoate;tin(4+) Chemical compound [Sn+4].CC(O)C([O-])=O.CC(O)C([O-])=O.CC(O)C([O-])=O.CC(O)C([O-])=O SKEZDZQGPKHHSH-UHFFFAOYSA-J 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- SMUSIFOACPPWGZ-UHFFFAOYSA-L di(hexadecanoyloxy)tin Chemical compound [Sn+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O SMUSIFOACPPWGZ-UHFFFAOYSA-L 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- CYCFYXLDTSNTGP-UHFFFAOYSA-L octadecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CYCFYXLDTSNTGP-UHFFFAOYSA-L 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Catalysts (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3933617A DE3933617A1 (de) | 1989-10-07 | 1989-10-07 | Verfahren zum herstellen von cyclischen kohlensaeureestern |
| JP2267519A JP2916706B2 (ja) | 1989-10-07 | 1990-10-03 | 環状炭酸エステルの製造方法 |
| DE59008704T DE59008704D1 (de) | 1989-10-07 | 1990-10-05 | Verfahren zum Herstellen von cyclischen Kohlensäureestern. |
| ES90119161T ES2068962T3 (es) | 1989-10-07 | 1990-10-05 | Procedimiento para la preparacion de esteres ciclicos de acido carbonico. |
| EP90119161A EP0422523B1 (de) | 1989-10-07 | 1990-10-05 | Verfahren zum Herstellen von cyclischen Kohlensäureestern |
| AT90119161T ATE119899T1 (de) | 1989-10-07 | 1990-10-05 | Verfahren zum herstellen von cyclischen kohlensäureestern. |
| DK90119161.9T DK0422523T3 (da) | 1989-10-07 | 1990-10-05 | Fremgangsmåde til fremstilling af cykliske kulsyreestere |
| US07/900,519 US5212321A (en) | 1989-10-07 | 1992-06-17 | Process for the preparation of trimethylene carbonate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3933617A DE3933617A1 (de) | 1989-10-07 | 1989-10-07 | Verfahren zum herstellen von cyclischen kohlensaeureestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3933617A1 DE3933617A1 (de) | 1991-04-18 |
| DE3933617C2 true DE3933617C2 (enExample) | 1991-10-31 |
Family
ID=6391077
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3933617A Granted DE3933617A1 (de) | 1989-10-07 | 1989-10-07 | Verfahren zum herstellen von cyclischen kohlensaeureestern |
| DE59008704T Expired - Lifetime DE59008704D1 (de) | 1989-10-07 | 1990-10-05 | Verfahren zum Herstellen von cyclischen Kohlensäureestern. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59008704T Expired - Lifetime DE59008704D1 (de) | 1989-10-07 | 1990-10-05 | Verfahren zum Herstellen von cyclischen Kohlensäureestern. |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0422523B1 (enExample) |
| JP (1) | JP2916706B2 (enExample) |
| AT (1) | ATE119899T1 (enExample) |
| DE (2) | DE3933617A1 (enExample) |
| DK (1) | DK0422523T3 (enExample) |
| ES (1) | ES2068962T3 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0816354A1 (de) * | 1996-06-25 | 1998-01-07 | Bayer Ag | Verfahren zur Herstellung und Stabilisierung von aliphatischen Sechsringcarbonaten |
| JPH11269166A (ja) * | 1998-03-19 | 1999-10-05 | Daicel Chem Ind Ltd | 環状炭酸エステルの製造方法 |
| US8323368B2 (en) | 2005-05-20 | 2012-12-04 | Nissan Chemical Industries, Ltd. | Production method of polishing composition |
| EP2709995B1 (en) * | 2011-05-14 | 2018-06-13 | Sang-Hyun Pyo | Method for producing cyclic carbonates |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3663569A (en) * | 1969-09-02 | 1972-05-16 | Atlas Chem Ind | Process for preparing cyclic carbonates from polyhydric alcohols |
| DE2265228A1 (de) * | 1971-05-13 | 1976-12-02 | Snam Progetti | Verfahren zur herstellung von polymeren carbonaten |
| US4374259A (en) * | 1978-06-29 | 1983-02-15 | Texaco Development Corporation | Process for converting substituted ethylene carbonates into substituted ethylene oxides using tin catalysts |
-
1989
- 1989-10-07 DE DE3933617A patent/DE3933617A1/de active Granted
-
1990
- 1990-10-03 JP JP2267519A patent/JP2916706B2/ja not_active Expired - Lifetime
- 1990-10-05 ES ES90119161T patent/ES2068962T3/es not_active Expired - Lifetime
- 1990-10-05 EP EP90119161A patent/EP0422523B1/de not_active Expired - Lifetime
- 1990-10-05 AT AT90119161T patent/ATE119899T1/de not_active IP Right Cessation
- 1990-10-05 DK DK90119161.9T patent/DK0422523T3/da active
- 1990-10-05 DE DE59008704T patent/DE59008704D1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03130279A (ja) | 1991-06-04 |
| EP0422523A3 (en) | 1991-09-18 |
| EP0422523A2 (de) | 1991-04-17 |
| DE59008704D1 (de) | 1995-04-20 |
| ATE119899T1 (de) | 1995-04-15 |
| DE3933617A1 (de) | 1991-04-18 |
| EP0422523B1 (de) | 1995-03-15 |
| DK0422523T3 (da) | 1995-05-22 |
| JP2916706B2 (ja) | 1999-07-05 |
| ES2068962T3 (es) | 1995-05-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0057360B1 (de) | Neue cyclische Kohlensäurederivate, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Copolymerisationskomponenten bei der Herstellung von Polycarbonaten | |
| EP0254950B1 (de) | (Meth)-acrylsäureester | |
| DE69409595T2 (de) | Verfahren zur Herstellung von Dialkylcarbonat | |
| DE3804820C2 (enExample) | ||
| DE3743782A1 (de) | Ester-urethan-(meth)-acrylsaeurederivate | |
| DE3235933A1 (de) | Verfahren zur herstellung bicyclischer orthoesteramide | |
| DE3933617C2 (enExample) | ||
| US5212321A (en) | Process for the preparation of trimethylene carbonate | |
| EP0017614B1 (de) | Verfahren zur Herstellung von Estern von Mercapto-alkanolen mit Hydroxyphenylcarbonsäuren | |
| WO2004076439A1 (de) | Verfahren zur herstellung von 4-fluor-1,3-dioxolan-2-on | |
| EP1924547A1 (de) | Verfahren zur herstellung von (meth) acrylaten vier- oder mehrwertiger alkohole | |
| DE2263819B2 (de) | Verfahren zur Herstellung von a- Alkoxy w-siloxanolen | |
| EP0001823A2 (de) | Verwendung von Borsäureestern zum Stabilisieren von phosphitfreien Polycarbonaten und die erhaltenen stabilisierten Polycarbonatformmassen | |
| EP0240871B1 (de) | Verfahren zur Herstellung aliphatischer Chlorverbindungen | |
| EP0090185B1 (de) | Verfahren zur Herstellung von Acetalen und Enoläthern aus Acryloxymethylenverbindungen | |
| EP0893427B1 (de) | Verfahren zur Herstellung von Cyclobutan-1,2-dicarbonsäureestern | |
| DE2508512C3 (de) | Verfahren zur Herstellung von O-Derivaten des p-Isopropenylphenols | |
| DE69707824T2 (de) | Neue Peroxyoxalate, abgeleitet von Hydroxy-hydroperoxiden | |
| DE2538310B2 (de) | Verfahren zur Herstellung von O.O-Dialkylthionophosphorsäurechloriden | |
| DE3639374A1 (de) | Ester von 3-tert.-butyl- bzw. 3-tert.-butyl-5-alkyl-4-hydroxyphenyl-(alkan)-carbonsaeuren mit oxethylaten von bis-(4- bzw. 2-hydroxyphenyl)-alkanen, -oxiden, -sulfiden und -sulfonen von tris-(4-hydroxyphenyl)-alkanen und von 1,3,5-tris-(4-hydroxyphenyl-isopropyliden)-arylen, verfahren zu ihrer herstellung und ihre verwendung als stabilisatoren | |
| EP0385194B1 (de) | Verfahren zur Herstellung von unsymmetrischen Spiroorthocarbonaten | |
| DE1281450B (de) | Verfahren zur Herstellung von cyclischen Carbonaten | |
| US3355481A (en) | Cyclopropane derivatives of 1, 7-octadiene | |
| DE3217665C2 (enExample) | ||
| DE3540216C2 (de) | Verfahren zur Herstellung von N-Methylphosphonsäurediestern von Acryl- bzw. Methacrylsäureamiden aus Methylolverbindungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |