GB485761A - Manufacture of isocyanates - Google Patents
Manufacture of isocyanatesInfo
- Publication number
- GB485761A GB485761A GB32204/36A GB3220436A GB485761A GB 485761 A GB485761 A GB 485761A GB 32204/36 A GB32204/36 A GB 32204/36A GB 3220436 A GB3220436 A GB 3220436A GB 485761 A GB485761 A GB 485761A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isocyanate
- ester yields
- methyl ester
- acid methyl
- yields
- 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
- 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)
Abstract
Isocyanates are obtained by the action of phosgene on urethanes of the type RNHCOOR1, where R is an alkyl, aryl, aralkyl or cycloalkyl group and R1 is an alkyl group. Urethanes of the type specified may be obtained by the known process wherein an alkaline alcoholic solution of a carboxylic acid amide is treated with halogen; specified amides from which urethanes may be so prepared are those of acetic, propionic, butyric, valeric, caproic, heptoic, caprylic, nonylic, capric, undecylenic, lauric, tridecylic, myristic, pentadecylic, palmitic, margaric, stearic, nondecylic, arachidic, behenic, lignoceric, cerotic, melissic, benzoic, o- and p-toluic, o- and p-methoxybenzoic, a -naphthoic, phenylacetic, phenylpropionic, o- and p-tolylacetic, hexahydrobenzoic, cyclohexylacetic, methylcyclohexylacetic, cyclohexylpropionic, naphthenic and hydroabietic acids, and also the amides of mixed acids such as are obtainable from coconut or palm-kernel oil, carnauba or montan wax, or hydrogenated fats. Suitable unethanes may also be obtained by the interaction of a primary amine and an alkyl chloroformate. Examples are given in which, by reaction with phosgene at a raised temperature in the presence or absence of a diluent, (1) N-heptadecylcarbamic acid methyl ester yields heptadecyl isocyanate; (2) N-phenylcarbamic acid methyl ester yields phenyl isocyanate; (3) N-benzylcarbamic acid methyl ester yields benzyl isocyanate; (4) N-methylcarbamic acid ethyl ester yields methyl isocyanate; (5) a mixture of N-alkylcarbamic acid esters, obtained by the action of chlorine and sodium methoxide on the amides of coconut-oil acids, yields a mixture of the corresponding alkyl isocyanates; (6) N-o-tolylcarbamic acid ethyl ester yields o-tolyl isocyanate; (7) N-p-tolylcarbamic acid methyl ester yields p-tolyl isocyanate; (8) N-cyclohexyl carbamic acid methyl ester yields cyclohexyl isocyanate.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB32204/36A GB485761A (en) | 1936-11-24 | 1936-11-24 | Manufacture of isocyanates |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB32204/36A GB485761A (en) | 1936-11-24 | 1936-11-24 | Manufacture of isocyanates |
Publications (1)
Publication Number | Publication Date |
---|---|
GB485761A true GB485761A (en) | 1938-05-24 |
Family
ID=10334913
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB32204/36A Expired GB485761A (en) | 1936-11-24 | 1936-11-24 | Manufacture of isocyanates |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB485761A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2416068A (en) * | 1944-05-27 | 1947-02-18 | Du Pont | Preparation of nu-cycloalkenyl carbamates |
US3404170A (en) * | 1965-09-27 | 1968-10-01 | Upjohn Co | Preparation of isocyanates |
FR2362123A1 (en) * | 1976-08-18 | 1978-03-17 | Bayer Ag | PROCESS FOR PREPARING ORGANIC ISOCYANATES, BY TERT-ALKYL-URETHANN REACTION WITH PHOSGENE AND PRODUCTS OBTAINED |
-
1936
- 1936-11-24 GB GB32204/36A patent/GB485761A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2416068A (en) * | 1944-05-27 | 1947-02-18 | Du Pont | Preparation of nu-cycloalkenyl carbamates |
US3404170A (en) * | 1965-09-27 | 1968-10-01 | Upjohn Co | Preparation of isocyanates |
FR2362123A1 (en) * | 1976-08-18 | 1978-03-17 | Bayer Ag | PROCESS FOR PREPARING ORGANIC ISOCYANATES, BY TERT-ALKYL-URETHANN REACTION WITH PHOSGENE AND PRODUCTS OBTAINED |
US4259255A (en) | 1976-08-18 | 1981-03-31 | Bayer Aktiengesellschaft | Process for the production of isocyanates |
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