IL42901A - Manufacture of urethanes - Google Patents
Manufacture of urethanesInfo
- Publication number
- IL42901A IL42901A IL42901A IL4290173A IL42901A IL 42901 A IL42901 A IL 42901A IL 42901 A IL42901 A IL 42901A IL 4290173 A IL4290173 A IL 4290173A IL 42901 A IL42901 A IL 42901A
- Authority
- IL
- Israel
- Prior art keywords
- process according
- compound
- catalyst
- selenium
- dinitrotoluene
- Prior art date
Links
- 150000003673 urethanes Chemical class 0.000 title claims 4
- 238000004519 manufacturing process Methods 0.000 title claims 2
- -1 nitrogenous organic compound Chemical class 0.000 claims abstract 9
- 239000003054 catalyst Substances 0.000 claims abstract 6
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims abstract 3
- 150000002894 organic compounds Chemical class 0.000 claims abstract 3
- 229910052711 selenium Inorganic materials 0.000 claims abstract 3
- 239000011669 selenium Substances 0.000 claims abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 125000004122 cyclic group Chemical group 0.000 claims abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 229940065287 selenium compound Drugs 0.000 claims abstract 2
- 150000003343 selenium compounds Chemical class 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 16
- DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 150000002828 nitro derivatives Chemical class 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- XTRDKALNCIHHNI-UHFFFAOYSA-N 2,6-dinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O XTRDKALNCIHHNI-UHFFFAOYSA-N 0.000 claims 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 150000002832 nitroso derivatives Chemical class 0.000 claims 1
- 150000003464 sulfur compounds Chemical class 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 abstract 2
- 229920002635 polyurethane Polymers 0.000 abstract 2
- 239000004814 polyurethane Substances 0.000 abstract 2
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
- C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
- C08G71/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/08—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
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)
- Polyurethanes Or Polyureas (AREA)
- Catalysts (AREA)
Abstract
1402379 Polyurethanes ATLANTIC RICHFIELD CO 31 July 1973 [30 Aug 1972] 36369/73 Heading C3R [Also in Division C2] Polyurethanes are prepared by reacting an organic compound containing at least two hydroxyl groups with carbon monoxide and a nitrogenous organic compound which has at least two non-cyclic groups in which a nitrogen atom is directly attached to a single carbon atom and is also attached through a double bond to an oxygen or nitrogen atom at an elevated temperature and pressure in the presence of a catalyst which is at least one of selenium, sulphur, a selenium compound, a sulphur compound or a mixture thereof a base and/or water.
[GB1402379A]
Claims (12)
1. CLAIMS 1. A process for preparing urethanes which comprises reacting an organic compound containing at least one hydroxyl group as herein defined with carbon monoxide and a nitrogenous organic compound as herein defined at an elevated temperature and pressure in the presence of a catalyst which is at least one of selenium, sulfur, a selenium compound, a sulfur compound or a mixture thereof as herein defined and at least one of a base or water.
2. A process according to claim 1, wherein the catalyst is selenium metal.
3. A process according to claim 1, wherein the catalyst is a mixture of selenium and sulfur.
4. A process according to any one of claims 1 to 3, wherein both base and water are present during the reaction.
5. A process according to any one of claims 1 to 4, wherein the process is conducted under an initial carbon monoxide pressure of from 10 to 100 atmospheres.
6. A process according.to any one of claims 1 to 5, wherein the temperature is maintained below 200 degrees C.
7. A process according to claim 6, wherei the temperature is from 100 to 200°C. and the catalyst is present in a molar amount of from 10 to 1 to 1000 o^ 1 of nitrogenous organic compound to catalyst.
8. A process according to any one of claims 1 to 7, wherein the organic compound containing at least one s 1 · hydroxy1 group is ethanol.
9. A process according to any one of claims 1 to 8 , wherein the nitrogenous organic oompound is at least one of an aromatic nitro compound, a tertiary aliphatic nitro compound, a tertiary cycloaliphatic nitro compound, a nitroso compound or an azo compound.
10. A process according to claim 9» wherein the aromatic nitro compound is a dinitrotoluene.
11. A process according to claim 10, wherein said dinitrotoluene is 2,l^-dinitrotoluene or 2,6-dinitrotoluene.
12. A process according to any one of claims 1 to 8, wherein the nitrogenous compound contains at least one non-cyclic group, in which a nitrogen atom is directly attached to a single carbon atom and is also attached through a double bond to an oxygen or nitrogen atom. 13· A process for the preparation of urethanes substantially as hereinbefore described with particular reference to Examples I to XXV. ll A process for the preparation of urethanes substantially as hereinbefore described with particular reference to Examples XXVI to XXXV. 15· A urethane when produced by a process according to claim 1. 16. A process according to claim 1, wherein an aliphatic or aromatic alcohol or a phenol is reacted with a nitro compound.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28487272A | 1972-08-30 | 1972-08-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42901A0 IL42901A0 (en) | 1973-11-28 |
| IL42901A true IL42901A (en) | 1976-09-30 |
Family
ID=23091841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42901A IL42901A (en) | 1972-08-30 | 1973-08-03 | Manufacture of urethanes |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS5243822B2 (en) |
| KR (1) | KR790001664B1 (en) |
| AR (1) | AR195740A1 (en) |
| AT (1) | AT332421B (en) |
| BE (1) | BE803976A (en) |
| BR (1) | BR7306716D0 (en) |
| CH (1) | CH577961A5 (en) |
| CS (1) | CS178903B2 (en) |
| DD (1) | DD105802A5 (en) |
| DK (1) | DK140984B (en) |
| EG (1) | EG11040A (en) |
| ES (1) | ES418439A1 (en) |
| FI (1) | FI58633C (en) |
| FR (1) | FR2197862B1 (en) |
| GB (1) | GB1402379A (en) |
| HU (1) | HU167891B (en) |
| IL (1) | IL42901A (en) |
| IT (1) | IT990429B (en) |
| LU (1) | LU68333A1 (en) |
| MY (1) | MY7700029A (en) |
| NO (1) | NO139859C (en) |
| PH (1) | PH13003A (en) |
| RO (1) | RO68466A (en) |
| SE (1) | SE403284B (en) |
| SU (1) | SU538661A3 (en) |
| TR (1) | TR17286A (en) |
| YU (1) | YU214973A (en) |
| ZA (1) | ZA735241B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS555601U (en) * | 1977-12-19 | 1980-01-14 | ||
| US4976679A (en) * | 1987-11-05 | 1990-12-11 | Takashi Okawa | Process for producing a urethane and a carbonic acid ester |
| CN113698597A (en) * | 2021-09-08 | 2021-11-26 | 华南理工大学 | Polydithiocarbamate compound and preparation method and application thereof |
-
1973
- 1973-07-31 SE SE7310511A patent/SE403284B/en unknown
- 1973-07-31 GB GB3636973A patent/GB1402379A/en not_active Expired
- 1973-08-01 ZA ZA735241A patent/ZA735241B/en unknown
- 1973-08-03 PH PH14882A patent/PH13003A/en unknown
- 1973-08-03 IL IL42901A patent/IL42901A/en unknown
- 1973-08-07 YU YU02149/73A patent/YU214973A/en unknown
- 1973-08-20 AT AT725373A patent/AT332421B/en not_active IP Right Cessation
- 1973-08-23 JP JP48093947A patent/JPS5243822B2/ja not_active Expired
- 1973-08-24 FR FR7330774A patent/FR2197862B1/fr not_active Expired
- 1973-08-24 BE BE1005312A patent/BE803976A/en unknown
- 1973-08-27 EG EG331/73A patent/EG11040A/en active
- 1973-08-27 FI FI2671/73A patent/FI58633C/en active
- 1973-08-28 AR AR249793A patent/AR195740A1/en active
- 1973-08-29 KR KR7301434A patent/KR790001664B1/en not_active Expired
- 1973-08-29 HU HUAA749A patent/HU167891B/hu unknown
- 1973-08-29 DD DD173150A patent/DD105802A5/xx unknown
- 1973-08-29 NO NO733407A patent/NO139859C/en unknown
- 1973-08-29 RO RO7375932A patent/RO68466A/en unknown
- 1973-08-29 SU SU1959122A patent/SU538661A3/en active
- 1973-08-29 DK DK474273AA patent/DK140984B/en unknown
- 1973-08-29 CS CS7300006020A patent/CS178903B2/en unknown
- 1973-08-29 TR TR17286A patent/TR17286A/en unknown
- 1973-08-29 CH CH1238673A patent/CH577961A5/xx not_active IP Right Cessation
- 1973-08-30 ES ES418439A patent/ES418439A1/en not_active Expired
- 1973-08-30 BR BR6716/73A patent/BR7306716D0/en unknown
- 1973-08-30 IT IT52250/73A patent/IT990429B/en active
- 1973-08-30 LU LU68333A patent/LU68333A1/xx unknown
-
1977
- 1977-12-30 MY MY29/77A patent/MY7700029A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO139859C (en) | 1979-05-23 |
| KR790001664B1 (en) | 1979-12-07 |
| BE803976A (en) | 1974-02-25 |
| AU5878173A (en) | 1975-02-06 |
| BR7306716D0 (en) | 1974-07-18 |
| PH13003A (en) | 1979-11-09 |
| ATA725373A (en) | 1976-01-15 |
| AT332421B (en) | 1976-09-27 |
| DD105802A5 (en) | 1974-05-12 |
| NO139859B (en) | 1979-02-12 |
| EG11040A (en) | 1976-12-31 |
| SU538661A3 (en) | 1976-12-05 |
| JPS5243822B2 (en) | 1977-11-02 |
| HU167891B (en) | 1976-01-28 |
| CH577961A5 (en) | 1976-07-30 |
| RO68466A (en) | 1981-06-26 |
| FR2197862A1 (en) | 1974-03-29 |
| AR195740A1 (en) | 1973-10-31 |
| TR17286A (en) | 1975-03-24 |
| MY7700029A (en) | 1977-12-31 |
| FI58633B (en) | 1980-11-28 |
| YU214973A (en) | 1982-02-25 |
| IT990429B (en) | 1975-06-20 |
| GB1402379A (en) | 1975-08-06 |
| DK140984C (en) | 1980-06-02 |
| FI58633C (en) | 1981-03-10 |
| JPS4962420A (en) | 1974-06-17 |
| IL42901A0 (en) | 1973-11-28 |
| ZA735241B (en) | 1974-07-31 |
| LU68333A1 (en) | 1974-03-07 |
| ES418439A1 (en) | 1976-10-16 |
| FR2197862B1 (en) | 1976-05-07 |
| SE403284B (en) | 1978-08-07 |
| CS178903B2 (en) | 1977-10-31 |
| DK140984B (en) | 1979-12-17 |
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