DE2222488C3 - Verfahren zur Herstellung von cyclischen Carbonaten aus Glykolen - Google Patents
Verfahren zur Herstellung von cyclischen Carbonaten aus GlykolenInfo
- Publication number
- DE2222488C3 DE2222488C3 DE2222488A DE2222488A DE2222488C3 DE 2222488 C3 DE2222488 C3 DE 2222488C3 DE 2222488 A DE2222488 A DE 2222488A DE 2222488 A DE2222488 A DE 2222488A DE 2222488 C3 DE2222488 C3 DE 2222488C3
- Authority
- DE
- Germany
- Prior art keywords
- carbon monoxide
- glycol
- glycols
- reaction
- carbonates
- 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
Links
- 238000000034 method Methods 0.000 title claims description 13
- 150000002334 glycols Chemical class 0.000 title claims description 5
- 150000005676 cyclic carbonates Chemical class 0.000 title claims 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 13
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims description 4
- 239000001569 carbon dioxide Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 5
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims 3
- 229910001431 copper ion Inorganic materials 0.000 claims 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- -1 alkaline earth metal carbonates Chemical class 0.000 claims 2
- 150000004651 carbonic acid esters Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229910000510 noble metal Inorganic materials 0.000 claims 2
- 150000007530 organic bases Chemical class 0.000 claims 2
- 150000000185 1,3-diols Chemical class 0.000 claims 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 claims 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
- 150000003624 transition metals Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 12
- 239000007789 gas Substances 0.000 description 5
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000021523 carboxylation Effects 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
Classifications
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/36—General preparatory processes using carbon monoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/01—Preparation of esters of carbonic or haloformic acids from carbon monoxide and oxygen
-
- 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
-
- 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
- C07D317/38—Ethylene carbonate
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/02—Aliphatic polycarbonates
- C08G64/0208—Aliphatic polycarbonates saturated
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
- C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2446871 | 1971-05-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2222488A1 DE2222488A1 (de) | 1972-11-23 |
| DE2222488B2 DE2222488B2 (de) | 1977-08-11 |
| DE2222488C3 true DE2222488C3 (de) | 1978-04-06 |
Family
ID=11213639
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2222488A Expired DE2222488C3 (de) | 1971-05-13 | 1972-05-08 | Verfahren zur Herstellung von cyclischen Carbonaten aus Glykolen |
| DE19722265228 Ceased DE2265228A1 (de) | 1971-05-13 | 1972-05-08 | Verfahren zur herstellung von polymeren carbonaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722265228 Ceased DE2265228A1 (de) | 1971-05-13 | 1972-05-08 | Verfahren zur herstellung von polymeren carbonaten |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5627516B1 (OSRAM) |
| AT (1) | AT319906B (OSRAM) |
| BE (1) | BE783337A (OSRAM) |
| CA (1) | CA965426A (OSRAM) |
| CH (2) | CH575941A5 (OSRAM) |
| DE (2) | DE2222488C3 (OSRAM) |
| DK (1) | DK135836B (OSRAM) |
| FR (1) | FR2137704B1 (OSRAM) |
| GB (1) | GB1382313A (OSRAM) |
| LU (1) | LU65333A1 (OSRAM) |
| NL (1) | NL151083B (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4423205A (en) | 1982-05-24 | 1983-12-27 | Ethyl Corporation | Cationic polymerization of cyclic carbonates |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57131244A (en) * | 1981-02-05 | 1982-08-14 | Furukawa Electric Co Ltd:The | Crosslinking of polycarbonate resin |
| US4456745A (en) * | 1982-05-24 | 1984-06-26 | Ethyl Corporation | Polyurethanes prepared from polycarbonates |
| DE3933617A1 (de) * | 1989-10-07 | 1991-04-18 | Boehringer Ingelheim Kg | Verfahren zum herstellen von cyclischen kohlensaeureestern |
| DE4225870A1 (de) * | 1992-08-05 | 1994-02-10 | Basf Ag | Verfahren zur Herstellung von Glycerincarbonat |
| US6222002B1 (en) | 1999-08-20 | 2001-04-24 | General Electric Company | Method for preparing polycarbonates by oxidative carbonylation |
| WO2010013579A1 (ja) * | 2008-08-01 | 2010-02-04 | 宇部興産株式会社 | ポリカ－ボネートジオール及びポリカーボネートジオール共重合体 |
| JP5573206B2 (ja) * | 2010-02-01 | 2014-08-20 | 宇部興産株式会社 | ポリウレタン樹脂、及びポリウレタン樹脂組成物 |
| DE102010042937A1 (de) | 2010-10-08 | 2012-04-12 | Bayer Materialscience Aktiengesellschaft | Verfahren zur Herstellung von Diarylcarbonaten aus Dialkylcarbonaten |
| DE102010042214A1 (de) | 2010-10-08 | 2012-04-12 | Bayer Materialscience Aktiengesellschaft | Katalysatorsystem für die oxidative Carbonylierung von Diolen und Polyolen |
| EP2650278A1 (de) | 2012-04-11 | 2013-10-16 | Bayer MaterialScience AG | Verfahren zur Herstellung von Diarylcarbonaten aus Dialkylcarbonaten |
-
1972
- 1972-05-08 DE DE2222488A patent/DE2222488C3/de not_active Expired
- 1972-05-08 DE DE19722265228 patent/DE2265228A1/de not_active Ceased
- 1972-05-09 DK DK229672AA patent/DK135836B/da unknown
- 1972-05-10 FR FR727216673A patent/FR2137704B1/fr not_active Expired
- 1972-05-11 CA CA142,225A patent/CA965426A/en not_active Expired
- 1972-05-11 GB GB2223772A patent/GB1382313A/en not_active Expired
- 1972-05-12 CH CH703372A patent/CH575941A5/xx not_active IP Right Cessation
- 1972-05-12 CH CH893775A patent/CH578023A5/xx not_active IP Right Cessation
- 1972-05-12 LU LU65333D patent/LU65333A1/xx unknown
- 1972-05-12 BE BE783337A patent/BE783337A/xx not_active IP Right Cessation
- 1972-05-12 AT AT416372A patent/AT319906B/de not_active IP Right Cessation
- 1972-05-13 JP JP4691272A patent/JPS5627516B1/ja active Pending
- 1972-05-15 NL NL727206503A patent/NL151083B/xx not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4423205A (en) | 1982-05-24 | 1983-12-27 | Ethyl Corporation | Cationic polymerization of cyclic carbonates |
Also Published As
| Publication number | Publication date |
|---|---|
| DK135836B (da) | 1977-07-04 |
| DE2222488A1 (de) | 1972-11-23 |
| NL151083B (nl) | 1976-10-15 |
| CH575941A5 (OSRAM) | 1976-05-31 |
| JPS5627516B1 (OSRAM) | 1981-06-25 |
| DK135836C (OSRAM) | 1977-11-28 |
| CH578023A5 (OSRAM) | 1976-07-30 |
| CA965426A (en) | 1975-04-01 |
| LU65333A1 (OSRAM) | 1972-08-23 |
| BE783337A (fr) | 1972-09-01 |
| DE2222488B2 (de) | 1977-08-11 |
| DE2265228A1 (de) | 1976-12-02 |
| AT319906B (de) | 1975-01-10 |
| NL7206503A (OSRAM) | 1972-11-15 |
| FR2137704A1 (OSRAM) | 1972-12-29 |
| FR2137704B1 (OSRAM) | 1974-07-05 |
| GB1382313A (en) | 1975-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BGA | New person/name/address of the applicant | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |