IE42098B1 - Process for the preparation of aliphatic polycarbonate diols - Google Patents
Process for the preparation of aliphatic polycarbonate diolsInfo
- Publication number
- IE42098B1 IE42098B1 IE2430/75A IE243075A IE42098B1 IE 42098 B1 IE42098 B1 IE 42098B1 IE 2430/75 A IE2430/75 A IE 2430/75A IE 243075 A IE243075 A IE 243075A IE 42098 B1 IE42098 B1 IE 42098B1
- Authority
- IE
- Ireland
- Prior art keywords
- diol
- acid
- transesterification
- process according
- catalyst
- Prior art date
Links
- 125000001931 aliphatic group Chemical group 0.000 title claims abstract description 19
- 150000002009 diols Chemical class 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000004417 polycarbonate Substances 0.000 title description 8
- 229920000515 polycarbonate Polymers 0.000 title description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000011541 reaction mixture Substances 0.000 claims abstract description 10
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 7
- 239000003377 acid catalyst Substances 0.000 claims abstract description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000005406 washing Methods 0.000 claims abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 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 description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000006378 damage Effects 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 8
- 229920002635 polyurethane Polymers 0.000 abstract description 3
- 239000004814 polyurethane Substances 0.000 abstract description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 abstract description 2
- 235000021355 Stearic acid Nutrition 0.000 abstract description 2
- 238000000748 compression moulding Methods 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract description 2
- 239000008117 stearic acid Substances 0.000 abstract description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 abstract 2
- -1 HCl Chemical class 0.000 abstract 1
- 238000004898 kneading Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000004821 distillation Methods 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- JFUIHGAGFMFNRD-UHFFFAOYSA-N fica Chemical compound FC1=CC=C2NC(C(=O)NCCS)=CC2=C1 JFUIHGAGFMFNRD-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940045860 white wax Drugs 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
-
- 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
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/305—General preparatory processes using carbonates and alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7440839A FR2294200A1 (fr) | 1974-12-11 | 1974-12-11 | Procede perfectionne de preparation d'oligocarbonates par double catalyse |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE42098L IE42098L (en) | 1976-06-11 |
| IE42098B1 true IE42098B1 (en) | 1980-06-04 |
Family
ID=9146038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2430/75A IE42098B1 (en) | 1974-12-11 | 1975-11-07 | Process for the preparation of aliphatic polycarbonate diols |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4005121A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS5183694A (cg-RX-API-DMAC10.html) |
| BE (1) | BE836533A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1064956A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2555882C3 (cg-RX-API-DMAC10.html) |
| DK (1) | DK559075A (cg-RX-API-DMAC10.html) |
| FR (1) | FR2294200A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1477285A (cg-RX-API-DMAC10.html) |
| IE (1) | IE42098B1 (cg-RX-API-DMAC10.html) |
| IT (1) | IT1051459B (cg-RX-API-DMAC10.html) |
| LU (1) | LU73969A1 (cg-RX-API-DMAC10.html) |
| NL (1) | NL7514068A (cg-RX-API-DMAC10.html) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2373570A1 (fr) * | 1976-12-10 | 1978-07-07 | Poudres & Explosifs Ste Nale | Nouveaux polycarbonates aliphatiques triols et leurs applications |
| US4349486A (en) * | 1978-12-15 | 1982-09-14 | General Electric Company | Monocarbonate transesterification process |
| IT1130285B (it) * | 1980-03-05 | 1986-06-11 | Anic Spa | Procedimento per la sintesi di allil carbonati di alcoli poliidrici e loro derivati |
| US4456745A (en) * | 1982-05-24 | 1984-06-26 | Ethyl Corporation | Polyurethanes prepared from polycarbonates |
| WO1987000185A1 (en) * | 1985-07-01 | 1987-01-15 | The Dow Chemical Company | A process for increasing the molecular weight of poly(alkylene carbonate) polyols |
| DE4130807A1 (de) * | 1991-09-17 | 1993-03-18 | Wolff Walsrode Ag | Verfahren zur herstellung von polysaccharidcarbonaten |
| TWI761404B (zh) | 2016-12-19 | 2022-04-21 | 德商科思創德意志股份有限公司 | 製備具有低反應性（環）脂族聚碳酸酯多元醇之方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2915529A (en) * | 1957-04-15 | 1959-12-01 | Jefferson Chem Co Inc | Method for preparing glycerin carbonate |
| DE1493757A1 (de) * | 1965-12-29 | 1969-01-30 | Bayer Ag | Verfahren zur Herstellung von gemischten Kohlensaeureestern |
-
1974
- 1974-12-11 FR FR7440839A patent/FR2294200A1/fr active Granted
-
1975
- 1975-11-07 IE IE2430/75A patent/IE42098B1/en unknown
- 1975-11-18 GB GB4746975A patent/GB1477285A/en not_active Expired
- 1975-12-01 CA CA240,851A patent/CA1064956A/en not_active Expired
- 1975-12-03 NL NL7514068A patent/NL7514068A/xx not_active Application Discontinuation
- 1975-12-04 US US05/637,758 patent/US4005121A/en not_active Expired - Lifetime
- 1975-12-09 LU LU73969A patent/LU73969A1/xx unknown
- 1975-12-09 IT IT70019/75A patent/IT1051459B/it active
- 1975-12-10 DK DK559075A patent/DK559075A/da not_active Application Discontinuation
- 1975-12-11 DE DE2555882A patent/DE2555882C3/de not_active Expired
- 1975-12-11 JP JP50146951A patent/JPS5183694A/ja active Pending
- 1975-12-11 BE BE162656A patent/BE836533A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1064956A (en) | 1979-10-23 |
| BE836533A (fr) | 1976-06-11 |
| FR2294200B1 (cg-RX-API-DMAC10.html) | 1984-02-17 |
| DE2555882A1 (de) | 1976-10-28 |
| DK559075A (da) | 1976-06-12 |
| DE2555882C3 (de) | 1980-04-03 |
| IE42098L (en) | 1976-06-11 |
| FR2294200A1 (fr) | 1976-07-09 |
| NL7514068A (nl) | 1976-06-15 |
| US4005121A (en) | 1977-01-25 |
| LU73969A1 (cg-RX-API-DMAC10.html) | 1977-07-01 |
| GB1477285A (en) | 1977-06-22 |
| DE2555882B2 (de) | 1979-08-02 |
| IT1051459B (it) | 1981-04-21 |
| JPS5183694A (cg-RX-API-DMAC10.html) | 1976-07-22 |
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