DE269938C - - Google Patents
Info
- Publication number
- DE269938C DE269938C DENDAT269938D DE269938DA DE269938C DE 269938 C DE269938 C DE 269938C DE NDAT269938 D DENDAT269938 D DE NDAT269938D DE 269938D A DE269938D A DE 269938DA DE 269938 C DE269938 C DE 269938C
- Authority
- DE
- Germany
- Prior art keywords
- urethane
- melting point
- glycol ethers
- ether
- cresol
- 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.)
- Active
Links
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 14
- -1 glycol ethers Chemical class 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 150000003673 urethanes Chemical class 0.000 claims description 3
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- WOAZEKPXTXCPFZ-UHFFFAOYSA-N dimethyl(phenyl)azanium;chloride Chemical compound Cl.CN(C)C1=CC=CC=C1 WOAZEKPXTXCPFZ-UHFFFAOYSA-N 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- AQJFATAFTQCRGC-UHFFFAOYSA-N 2-Chloro-4-methylphenol Chemical compound CC1=CC=C(O)C(Cl)=C1 AQJFATAFTQCRGC-UHFFFAOYSA-N 0.000 description 1
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- LIXQEKDONFVMOB-UHFFFAOYSA-N benzene;carbonyl dichloride Chemical compound ClC(Cl)=O.C1=CC=CC=C1 LIXQEKDONFVMOB-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical class OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 description 1
- FFNJJMHCIRZBJO-UHFFFAOYSA-N ethyl n-(2-phenoxyethyl)carbamate Chemical compound CCOC(=O)NCCOC1=CC=CC=C1 FFNJJMHCIRZBJO-UHFFFAOYSA-N 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE269938C true DE269938C (en:Method) |
Family
ID=526741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT269938D Active DE269938C (en:Method) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE269938C (en:Method) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2609386A (en) * | 1951-07-26 | 1952-09-02 | Squibb & Sons Inc | Carbamate of 3-ortho-toloxy-1, 2-propanediol |
| US4382765A (en) * | 1977-02-05 | 1983-05-10 | Henkel Kommanditgesellschaft Auf Aktien | Method of moisturizing the skin with carbamide acid esters |
-
0
- DE DENDAT269938D patent/DE269938C/de active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2609386A (en) * | 1951-07-26 | 1952-09-02 | Squibb & Sons Inc | Carbamate of 3-ortho-toloxy-1, 2-propanediol |
| US4382765A (en) * | 1977-02-05 | 1983-05-10 | Henkel Kommanditgesellschaft Auf Aktien | Method of moisturizing the skin with carbamide acid esters |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE269938C (en:Method) | ||
| DE506282C (de) | Verfahren zur Darstellung hochalkylierter Guanidine | |
| DE2620445C3 (de) | Verfahren zur Herstellung von Glycinnitrilen | |
| DE927992C (de) | Verfahren zur Herstellung von Salzen des 1, 2-Dimethyl-3-phenyl-4-amino-5-pyrazolons | |
| DE952981C (de) | Verfahren zur Herstellung von oberflaechenaktiven polyoxalkylierten N-(tert.-Alkyl)-aminen | |
| DE607870C (de) | Verfahren zur Herstellung von Diazopraeparaten | |
| DE510441C (de) | Verfahren zur Herstellung wasserloeslicher, gemischt aromatisch-aliphatischer Diazoaminoverbindungen | |
| AT235839B (de) | Verfahren zur Herstellung von Chinazolon-(4)-Derivaten | |
| DE762425C (de) | Verfahren zur Herstellung von eine acylierte Benzylaminogruppe enthaltenden quartaeren Ammoniumverbindungen | |
| EP0003767A1 (de) | N-Acylaminohydroxynaphthalinsulfonsäuresalze, Verfahren zu ihrer Herstellung und ihre Verwendung als Kupplungskomponenten zur Herstellung von Azofarbstoffen | |
| DE961086C (de) | Verfahren zur Herstellung von Oxazolidonen-(2) | |
| DE1904293C (de) | Verfahren zur Herstellung von wasser freien Halogenalkylaminhydrohalogemden | |
| DE955055C (de) | Verfahren zur Herstellung von Aminooxyphenylisothioharnstoff | |
| DE664309C (de) | Verfahren zur Herstellung von Amiden hoehermolekularer Carbonsaeuren | |
| DE930212C (de) | Verfahren zur Herstellung von neuen Phosphonsaeuredialkylestern | |
| DE478331C (de) | Verfahren zur Darstellung von Sulfoderivaten der Oxyarylcarbonsaeurearylide | |
| DE1545824A1 (de) | Verfahren zur Herstellung von 2-Sulfonamido- bzw. 2-Sulfonhydrazido-Benzoxazinonen | |
| DE678194C (de) | Verfahren zur Herstellung von Verbindungen von Mercaptothiazolen | |
| DE501280C (de) | Verfahren zur Darstellung von 4-(B-Oxyaethylamino-) 1-oxybenzol | |
| DE860064C (de) | Verfahren zur Herstellung von Polyaminoverbindungen | |
| DE892135C (de) | Verfahren zur Herstellung von Harnstoffabkoemmlingen | |
| DE814151C (de) | Verfahren zur Herstellung von N-Alkyl-2-thioalkylbenzimidazolen | |
| DE858565C (de) | Verfahren zur Herstellung von Sulfonamiden der 1, 3-Dioxanreihe | |
| DE168115C (en:Method) | ||
| DE553074C (de) | Verfahren zur Darstellung von Aminosulfonsaeuren |