CA1166650A - Process for the production of n- and o-substituted mono- or bis-urethanes and the use thereof as starting material for the production of aliphatic isocyanates - Google Patents
Process for the production of n- and o-substituted mono- or bis-urethanes and the use thereof as starting material for the production of aliphatic isocyanatesInfo
- Publication number
- CA1166650A CA1166650A CA000385292A CA385292A CA1166650A CA 1166650 A CA1166650 A CA 1166650A CA 000385292 A CA000385292 A CA 000385292A CA 385292 A CA385292 A CA 385292A CA 1166650 A CA1166650 A CA 1166650A
- Authority
- CA
- Canada
- Prior art keywords
- hydrocarbon radical
- thallium
- carbon atoms
- general formula
- salts
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/04—Preparation of derivatives of isocyanic acid from or via carbamates or carbamoyl halides
-
- 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
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Mo-2239 LeA 20,581 PROCESS FOR THE PRODUCTION OF N- AND O-SUBSTITUTED MONO- OR BIS-URETHANES AND THE
USE THEREOF AS STARTING MATERIAL FOR THE
PRODUCTION OF ALIPHATIC ISOCYANATES
ABSTRACT OF THE DISCLOSURE
The present invention is directed to a process for the production of N- and O-substituted mono- or bis-urethanes, characterized in that urethanes corre-sponding to the following general formula:
R1?NH-CO-O-R2)n wherein R1 represents either an n-functional, aliphatic C1-C6 hydrocarbon radical optionally containing ether bridges or an n-functional cycloaliphatic C6-C13 hydrocarbon radical;
R2 represents a hydroxyalkyl group containing 2 or 3 carbon atoms, 2 carbon atoms being arranged between the oxygen atom of the hydroxyl group and the oxygen atom of the urethane group; and n represents 1 or 2;
are subjected to a transesterification reaction using alcohols containing only primary hydroxyl groups and corresponding to the following general formula:
R3?OH)m wherein R3 represents a monofunctional (m = 1), linear or branched saturated aliphatic C8-C18 hydrocarbon radical optionally containing ether bridges, a monofunctional (m = 1), araliphatic C8-C15 hydrocarbon radical or a difunctional (m = 2), linear or branched, saturated aliphatic C3-C18 hydrocarbon radical optionally con-taining ether bridges, in which at least 3 carbon atoms are arranged between the 2 hydroxyl groups; and Mo-2239 LeA 20,581 m represents 1 or 2, with the proviso that not both m and n represent 2;
in the presence of catalysts selected from; (i) thallium oxides, thallium hydroxides, thallium salts of organic acids, thallium salts of weak inorganic acids and organic complex compounds of monovalent thallium and, (ii) salts of organic acids of divalent and tetravalent tin and organic compounds of tetravalent tin with organ-ic residues which are not bound like salts, the reaction being accompanied by the elimination of alcohols corresponding to the following general formula:
R2-OH.
Mo-2239 LeA 20,581
USE THEREOF AS STARTING MATERIAL FOR THE
PRODUCTION OF ALIPHATIC ISOCYANATES
ABSTRACT OF THE DISCLOSURE
The present invention is directed to a process for the production of N- and O-substituted mono- or bis-urethanes, characterized in that urethanes corre-sponding to the following general formula:
R1?NH-CO-O-R2)n wherein R1 represents either an n-functional, aliphatic C1-C6 hydrocarbon radical optionally containing ether bridges or an n-functional cycloaliphatic C6-C13 hydrocarbon radical;
R2 represents a hydroxyalkyl group containing 2 or 3 carbon atoms, 2 carbon atoms being arranged between the oxygen atom of the hydroxyl group and the oxygen atom of the urethane group; and n represents 1 or 2;
are subjected to a transesterification reaction using alcohols containing only primary hydroxyl groups and corresponding to the following general formula:
R3?OH)m wherein R3 represents a monofunctional (m = 1), linear or branched saturated aliphatic C8-C18 hydrocarbon radical optionally containing ether bridges, a monofunctional (m = 1), araliphatic C8-C15 hydrocarbon radical or a difunctional (m = 2), linear or branched, saturated aliphatic C3-C18 hydrocarbon radical optionally con-taining ether bridges, in which at least 3 carbon atoms are arranged between the 2 hydroxyl groups; and Mo-2239 LeA 20,581 m represents 1 or 2, with the proviso that not both m and n represent 2;
in the presence of catalysts selected from; (i) thallium oxides, thallium hydroxides, thallium salts of organic acids, thallium salts of weak inorganic acids and organic complex compounds of monovalent thallium and, (ii) salts of organic acids of divalent and tetravalent tin and organic compounds of tetravalent tin with organ-ic residues which are not bound like salts, the reaction being accompanied by the elimination of alcohols corresponding to the following general formula:
R2-OH.
Mo-2239 LeA 20,581
Claims (3)
1. A process for the production of N- and O-substituted mono- or bis-urethanes, characterized in that urethanes corresponding to the following general formula:
R1?NH-CO-O-R2)n wherein R1 represents either an n-functional, aliphatic C1-C6 hydrocarbon radical optionally containing ether bridges or an n-functional cycloaliphatic C6-C13 hydrocarbon radical;
R2 represents a hydroxyalkyl group containing 2 or 3 carbon atoms, 2 carbon atoms being arranged between the oxygen atom of the hydroxyl group and the oxygen atom of the urethane group; and n represents 1 or 2;
are subjected to a transesterification reaction using alcohols containing only primary hydroxyl groups and corresponding to the following general formula:
R3?OH)m wherein R3 represents a monofunctional (m =1), linear or branched saturated aliphatic C8-C18 hydrocarbon radical optionally containing ether bridges, a mono-functional (m = 1), araliphatic C8-C15 hydrocarbon radical or a difunctional (m = 2), linear or branched, saturated aliphatic C3-C18 hydrocarbon radical option-ally containing ether bridges, in which at least 3 carbon atoms are arranged between the 2 hydroxyl groups; and m represents 1 or 2, with the proviso that not both m and n represent 2;
Mo-2239 LeA 20,581 in the presence of catalysts selected from; (i) thallium oxides, thallium hydroxides, thallium salts of organic acids, thallium salts of weak inorganic acids and or-ganic complex compounds of monovalent thallium and, (ii) salts of organic acids of divalent and tetravalent tin and organic compounds of tetravalent tin with or-ganic residues which are not bound like salts, the reaction being accompanied by the elimination of alcohols corresponding to the following general formu-la:
R2-OH.
R1?NH-CO-O-R2)n wherein R1 represents either an n-functional, aliphatic C1-C6 hydrocarbon radical optionally containing ether bridges or an n-functional cycloaliphatic C6-C13 hydrocarbon radical;
R2 represents a hydroxyalkyl group containing 2 or 3 carbon atoms, 2 carbon atoms being arranged between the oxygen atom of the hydroxyl group and the oxygen atom of the urethane group; and n represents 1 or 2;
are subjected to a transesterification reaction using alcohols containing only primary hydroxyl groups and corresponding to the following general formula:
R3?OH)m wherein R3 represents a monofunctional (m =1), linear or branched saturated aliphatic C8-C18 hydrocarbon radical optionally containing ether bridges, a mono-functional (m = 1), araliphatic C8-C15 hydrocarbon radical or a difunctional (m = 2), linear or branched, saturated aliphatic C3-C18 hydrocarbon radical option-ally containing ether bridges, in which at least 3 carbon atoms are arranged between the 2 hydroxyl groups; and m represents 1 or 2, with the proviso that not both m and n represent 2;
Mo-2239 LeA 20,581 in the presence of catalysts selected from; (i) thallium oxides, thallium hydroxides, thallium salts of organic acids, thallium salts of weak inorganic acids and or-ganic complex compounds of monovalent thallium and, (ii) salts of organic acids of divalent and tetravalent tin and organic compounds of tetravalent tin with or-ganic residues which are not bound like salts, the reaction being accompanied by the elimination of alcohols corresponding to the following general formu-la:
R2-OH.
2. A process as claimed in Claim 1, charac-terized in that compounds wherein R1 represents a monofunctional aliphatic hydrocarbon radical containing from 1 to 6 carbon atoms;
R2 is as defined in Claim l; and n represents 1 are used as the compounds corresponding to the general formula:
R1?NH-CO-O-R2)n and the transesterification reaction is carried out using alcohols corresponding to the following general formula:
R3?OH)m wherein R3 represents a monofunctional aliphatic hydrocarbon radical containing from 8 to 18 carbon atoms; and m represents 1.
R2 is as defined in Claim l; and n represents 1 are used as the compounds corresponding to the general formula:
R1?NH-CO-O-R2)n and the transesterification reaction is carried out using alcohols corresponding to the following general formula:
R3?OH)m wherein R3 represents a monofunctional aliphatic hydrocarbon radical containing from 8 to 18 carbon atoms; and m represents 1.
3. A process as claimed in Claim 2, charac-terized in that compounds wherein R represents a hydroxy ethyl radical Mo-2239 LeA 20,581 are used as the compounds corresponding to the general formula:
R1?NH-CO-O-R2).
Mo-2239 LeA 20,581
R1?NH-CO-O-R2).
Mo-2239 LeA 20,581
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3035146.3 | 1980-09-18 | ||
| DE19803035146 DE3035146A1 (en) | 1980-09-18 | 1980-09-18 | METHOD FOR THE PRODUCTION OF N- AND O-SUBSTITUTED MONO- OR BIS-URETHANES, AND THE USE THEREOF AS THE STARTING MATERIAL FOR THE PRODUCTION OF ALIPHATIC ISOCYANATES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1166650A true CA1166650A (en) | 1984-05-01 |
Family
ID=6112229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000385292A Expired CA1166650A (en) | 1980-09-18 | 1981-09-04 | Process for the production of n- and o-substituted mono- or bis-urethanes and the use thereof as starting material for the production of aliphatic isocyanates |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0048368B1 (en) |
| JP (1) | JPS5782360A (en) |
| AU (1) | AU7523681A (en) |
| BR (1) | BR8105942A (en) |
| CA (1) | CA1166650A (en) |
| DE (2) | DE3035146A1 (en) |
| ES (1) | ES8206451A1 (en) |
| ZA (1) | ZA816453B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT390442B (en) * | 1988-05-30 | 1990-05-10 | Vianova Kunstharz Ag | METHOD FOR THE PRODUCTION OF N- (2-BENZIMIDAZOLYL) -CARBAMIDSAEUREALKYLESTER PR PARATIONS AND THE USE THEREOF FOR WOOD PROTECTIVE VARNISHES |
| US4883854A (en) * | 1988-09-30 | 1989-11-28 | Medtronic, Inc. | Hydroxyl functional monomers |
| US5001210A (en) * | 1988-09-30 | 1991-03-19 | Medtronic, Inc. | Method for producing polyurethanes from poly-(hydroxyalkyl urethanes) |
| US5326903A (en) * | 1992-01-10 | 1994-07-05 | Nippon Shokubai Co., Ltd. | Process for preparing isocyanates using sintered oxides |
| JPH11343276A (en) | 1998-03-31 | 1999-12-14 | Mitsui Chem Inc | New urethane compound and production of multifunctional aliphatic diisocyanate |
| US6133473A (en) * | 1998-06-25 | 2000-10-17 | Rohm And Haas Company | Synthesis of carbamate compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3265728A (en) * | 1962-07-18 | 1966-08-09 | Armour Pharma | Substituted phenethyl carbamates |
| US3734941A (en) * | 1968-09-06 | 1973-05-22 | American Cyanamid Co | Process for converting urethanes to isocyanates |
| GB1231946A (en) * | 1969-03-20 | 1971-05-12 | ||
| US3919280A (en) * | 1974-07-05 | 1975-11-11 | Atlantic Richfield Co | Recovery of solvents employed in the production of isocyanates from esters of carbamic acids |
-
1980
- 1980-09-18 DE DE19803035146 patent/DE3035146A1/en not_active Withdrawn
-
1981
- 1981-09-04 CA CA000385292A patent/CA1166650A/en not_active Expired
- 1981-09-05 EP EP81106989A patent/EP0048368B1/en not_active Expired
- 1981-09-05 DE DE8181106989T patent/DE3164185D1/en not_active Expired
- 1981-09-15 AU AU75236/81A patent/AU7523681A/en not_active Abandoned
- 1981-09-16 JP JP56144845A patent/JPS5782360A/en active Pending
- 1981-09-17 ZA ZA816453A patent/ZA816453B/en unknown
- 1981-09-17 BR BR8105942A patent/BR8105942A/en unknown
- 1981-09-17 ES ES505559A patent/ES8206451A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU7523681A (en) | 1982-03-25 |
| BR8105942A (en) | 1982-06-08 |
| EP0048368B1 (en) | 1984-06-13 |
| JPS5782360A (en) | 1982-05-22 |
| EP0048368A2 (en) | 1982-03-31 |
| ES505559A0 (en) | 1982-08-16 |
| ZA816453B (en) | 1982-09-29 |
| EP0048368A3 (en) | 1982-05-12 |
| ES8206451A1 (en) | 1982-08-16 |
| DE3164185D1 (en) | 1984-07-19 |
| DE3035146A1 (en) | 1982-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |