FI86719B - Foerfarande foer framstaellning av 2-oxo-1,3-dioxolaner. - Google Patents
Foerfarande foer framstaellning av 2-oxo-1,3-dioxolaner. Download PDFInfo
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- FI86719B FI86719B FI863298A FI863298A FI86719B FI 86719 B FI86719 B FI 86719B FI 863298 A FI863298 A FI 863298A FI 863298 A FI863298 A FI 863298A FI 86719 B FI86719 B FI 86719B
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- process according
- epoxide
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- 238000005057 refrigeration Methods 0.000 title 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 42
- 150000002118 epoxides Chemical class 0.000 claims description 42
- -1 tritolylphosphane Chemical group 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 22
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical group CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 18
- 239000001569 carbon dioxide Substances 0.000 claims description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 16
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 12
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 11
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- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical group C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
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- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 5
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
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- 239000000203 mixture Substances 0.000 description 12
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
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- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
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- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229960004337 hydroquinone Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical class C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 229910000064 phosphane Inorganic materials 0.000 description 1
- 150000003002 phosphanes Chemical class 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000921 polyethylene adipate Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- LVBXEMGDVWVTGY-UHFFFAOYSA-N trans-2-octenal Natural products CCCCCC=CC=O LVBXEMGDVWVTGY-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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)
- Epoxy Compounds (AREA)
- Epoxy Resins (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Secondary Cells (AREA)
Claims (11)
1. Förfarande för framställning av 2-oxo-l,3-dioxo-laner genom att omsätta epoxider med koldioxid i närvaro 5 av en katalysator och eventuellt i närvaro av en kokataly-sator och ett inert lösningsmedel, känneteck-n a t därav, att reaktionen utförs vid en temperatur av 40 - 180 °C och under normaltryck eller nägot förhöjt tryck i närvaro av minst en katalysator, som är trifenyl-10 fosfan, tritolylfosfan, diazabicyklo[2.2.2]oktan, 4-dime-tylaminopyridin, 4-(1-pyrrolidinyl)pyridin, amidin, imid-azol eller en alkyl-, aryl- eller aralkyl-substitutions-produkt därav.
2. Förfarande enligt patentkravet 1, k ä n n e -15 tecknat därav, att reaktionen utförs under ett tryck av 1 - 5 bar.
3. Förfarande enligt patentkravet 1 eller 2, k ä n-netecknat därav, att man använder 0,02 - 10 vikt-% katalysator beräknat pä epoxidkomponenten. 20
4. Förfarande enligt nägot av patentkraven 1-3, kännetecknat därav, att reaktionen av epoxid-föreningen med koldioxid utförs endast delvis.
5. Förfarande enligt nägot av patentkraven 1-4, kännetecknat därav, att som imidazol används 25 1-metyl-, 2-metyl- och/eller 2-etyl-4-metyl-imidazol.
6. Förfarande enligt nägot av patentkraven 1-5, kännetecknat därav, att ytterligare används 0,1 - 10 vikt-% kokatalysatorer beräknat pä epoxidkomponenten . 30
7. Förfarande enligt nägot av patentkraven 1-6, kännetecknat därav, att som kokatalysator används natrium- och/eller kaliumjodid.
8. Förfarande enligt nägot av de föregäende patentkraven, kännetecknat därav, att epoxidföre-35 ningarna innehäller minst en terminal 1,2-epoxigrupp. 2i 86719
9. Förfarande enligt patentkravet 8, känne- t e c k n a t därav, att som epoxidföreningar används alifatiska epoxider, som innehäller minst 6 kolatomer, glycidol eller en epihalogenhydrin med formeln (2), 5 Z X-CH0-C-CH„ (2) 2 \</ 10 där Z är en väteatom eller en metyl- eller etylgrupp, och X är en halogenatom eller en OH-grupp.
10. Förfarande enligt patentkravet 8, känne-t e c k n a t därav, att som epoxidföreningar används sä-dana epoxider, som innehäller i medeltal minst en substi- 15 tuerad eller icke-substituerad glycidyletergrupp med formeln (3), Z -0-CHo-C-CH„ (3) 2 \ / 2 20 0 eller en substituerad eller icke-substituerad glycidyles-tergrupp med formeln (4),
25 Z l -OC-O-CH^-C-CH0 (4) 2 varvid Z i bäda formlerna betecknar samma som ovan, och 30 ytterligare epoxiderade, mängfaldigt omättade föreningar och epoxider innehällande amid- eller uretangrupper.
11. Förfarande enligt nägot av patentkraven 8 - 10, kännetecknat därav, att som epoxidföreningar används en polyglycidyleter, plasticerade epoxihartser, 35 som innehäller terminals epoxidgrupper, eller glycidylest-rar av mättade eller etyleniskt omättade (poly)karboxylsy-ror.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3529263 | 1985-08-16 | ||
DE19853529263 DE3529263A1 (de) | 1985-08-16 | 1985-08-16 | Verfahren zur herstellung von 2-oxo-1,3-dioxolanen |
Publications (4)
Publication Number | Publication Date |
---|---|
FI863298A0 FI863298A0 (fi) | 1986-08-14 |
FI863298A FI863298A (fi) | 1987-02-17 |
FI86719B true FI86719B (fi) | 1992-06-30 |
FI86719C FI86719C (sv) | 1992-10-12 |
Family
ID=6278572
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI863298A FI86719C (sv) | 1985-08-16 | 1986-08-14 | Förfarande för framställning av 2-oxo-1,3-dioxolaner |
Country Status (18)
Country | Link |
---|---|
US (1) | US4892954A (sv) |
EP (1) | EP0212409B1 (sv) |
JP (1) | JP2565875B2 (sv) |
KR (1) | KR940008751B1 (sv) |
CN (1) | CN1020729C (sv) |
AR (1) | AR242201A1 (sv) |
AT (1) | ATE51225T1 (sv) |
AU (1) | AU585385B2 (sv) |
BR (1) | BR8603901A (sv) |
CA (1) | CA1334851C (sv) |
DE (2) | DE3529263A1 (sv) |
DK (1) | DK164864C (sv) |
ES (1) | ES2000286A6 (sv) |
FI (1) | FI86719C (sv) |
MX (1) | MX170907B (sv) |
NO (1) | NO863302L (sv) |
PT (1) | PT83209B (sv) |
ZA (1) | ZA866149B (sv) |
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CN115181087A (zh) * | 2022-08-25 | 2022-10-14 | 山东东岳高分子材料有限公司 | 一种离子液体复合催化剂制备碳酸乙烯酯的方法 |
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-
1985
- 1985-08-16 DE DE19853529263 patent/DE3529263A1/de not_active Withdrawn
-
1986
- 1986-08-04 EP EP86110736A patent/EP0212409B1/de not_active Expired - Lifetime
- 1986-08-04 DE DE8686110736T patent/DE3669717D1/de not_active Expired - Lifetime
- 1986-08-04 AT AT86110736T patent/ATE51225T1/de not_active IP Right Cessation
- 1986-08-14 AR AR86304909A patent/AR242201A1/es active
- 1986-08-14 ES ES8601130A patent/ES2000286A6/es not_active Expired
- 1986-08-14 DK DK387386A patent/DK164864C/da not_active IP Right Cessation
- 1986-08-14 FI FI863298A patent/FI86719C/sv not_active IP Right Cessation
- 1986-08-14 PT PT83209A patent/PT83209B/pt not_active IP Right Cessation
- 1986-08-15 NO NO863302A patent/NO863302L/no unknown
- 1986-08-15 CA CA000516014A patent/CA1334851C/en not_active Expired - Fee Related
- 1986-08-15 BR BR8603901A patent/BR8603901A/pt not_active IP Right Cessation
- 1986-08-15 AU AU61506/86A patent/AU585385B2/en not_active Ceased
- 1986-08-15 ZA ZA866149A patent/ZA866149B/xx unknown
- 1986-08-15 MX MX003452A patent/MX170907B/es unknown
- 1986-08-15 JP JP61190730A patent/JP2565875B2/ja not_active Expired - Lifetime
- 1986-08-16 CN CN86105205A patent/CN1020729C/zh not_active Expired - Fee Related
- 1986-08-16 KR KR1019860006754A patent/KR940008751B1/ko not_active IP Right Cessation
-
1987
- 1987-10-21 US US07/111,979 patent/US4892954A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
AU585385B2 (en) | 1989-06-15 |
EP0212409B1 (de) | 1990-03-21 |
DK387386A (da) | 1987-02-17 |
AR242201A1 (es) | 1993-03-31 |
EP0212409A3 (en) | 1987-10-21 |
BR8603901A (pt) | 1987-03-24 |
CA1334851C (en) | 1995-03-21 |
MX170907B (es) | 1993-09-22 |
KR870002117A (ko) | 1987-03-30 |
AU6150686A (en) | 1987-02-19 |
ATE51225T1 (de) | 1990-04-15 |
NO863302D0 (no) | 1986-08-15 |
PT83209A (en) | 1986-09-01 |
FI86719C (sv) | 1992-10-12 |
FI863298A0 (fi) | 1986-08-14 |
US4892954A (en) | 1990-01-09 |
ZA866149B (en) | 1987-04-29 |
CN86105205A (zh) | 1987-02-11 |
JPS6245584A (ja) | 1987-02-27 |
ES2000286A6 (es) | 1988-02-01 |
DK164864B (da) | 1992-08-31 |
DK387386D0 (da) | 1986-08-14 |
KR940008751B1 (ko) | 1994-09-26 |
EP0212409A2 (de) | 1987-03-04 |
NO863302L (no) | 1987-02-17 |
DE3529263A1 (de) | 1987-02-19 |
JP2565875B2 (ja) | 1996-12-18 |
DK164864C (da) | 1993-01-18 |
DE3669717D1 (de) | 1990-04-26 |
FI863298A (fi) | 1987-02-17 |
CN1020729C (zh) | 1993-05-19 |
PT83209B (pt) | 1989-03-30 |
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MM | Patent lapsed | ||
MM | Patent lapsed |
Owner name: HOECHST AKTIENGESELLSCHAFT |