DE2138727C3 - Verfahren zur Herstellung von Orthokohlensäureestern - Google Patents
Verfahren zur Herstellung von OrthokohlensäureesternInfo
- Publication number
- DE2138727C3 DE2138727C3 DE2138727A DE2138727A DE2138727C3 DE 2138727 C3 DE2138727 C3 DE 2138727C3 DE 2138727 A DE2138727 A DE 2138727A DE 2138727 A DE2138727 A DE 2138727A DE 2138727 C3 DE2138727 C3 DE 2138727C3
- Authority
- DE
- Germany
- Prior art keywords
- acid esters
- aromatic
- preparation
- reaction
- monofunctional
- 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
- 238000000034 method Methods 0.000 title claims description 10
- RXCVUXLCNLVYIA-UHFFFAOYSA-N orthocarbonic acid Chemical class OC(O)(O)O RXCVUXLCNLVYIA-UHFFFAOYSA-N 0.000 title description 3
- -1 aromatic hydroxy compound Chemical class 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- SXLDBFDRSPKHLY-UHFFFAOYSA-N trichloro(isocyano)methane Chemical compound ClC(Cl)(Cl)[N+]#[C-] SXLDBFDRSPKHLY-UHFFFAOYSA-N 0.000 description 9
- 239000007789 gas Substances 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CNBXDJWILPHVPK-UHFFFAOYSA-N ClC(C=C1)=CC(Cl)=C1OC(OC(C=CC(Cl)=C1)=C1Cl)(OC(C=CC(Cl)=C1)=C1Cl)OC(C=CC(Cl)=C1)=C1Cl Chemical compound ClC(C=C1)=CC(Cl)=C1OC(OC(C=CC(Cl)=C1)=C1Cl)(OC(C=CC(Cl)=C1)=C1Cl)OC(C=CC(Cl)=C1)=C1Cl CNBXDJWILPHVPK-UHFFFAOYSA-N 0.000 description 1
- ROZUXUFQNKPPBP-UHFFFAOYSA-N ClC1=C(C=CC=C1)OC(OC1=C(C=CC=C1)Cl)(OC1=C(C=CC=C1)Cl)OC1=C(C=CC=C1)Cl Chemical compound ClC1=C(C=CC=C1)OC(OC1=C(C=CC=C1)Cl)(OC1=C(C=CC=C1)Cl)OC1=C(C=CC=C1)Cl ROZUXUFQNKPPBP-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- QORPNMNELZSPSU-UHFFFAOYSA-N [O-][N+](C(C=C1)=CC=C1OC(OC(C=C1)=CC=C1[N+]([O-])=O)(OC(C=C1)=CC=C1[N+]([O-])=O)OC(C=C1)=CC=C1[N+]([O-])=O)=O Chemical compound [O-][N+](C(C=C1)=CC=C1OC(OC(C=C1)=CC=C1[N+]([O-])=O)(OC(C=C1)=CC=C1[N+]([O-])=O)OC(C=C1)=CC=C1[N+]([O-])=O)=O QORPNMNELZSPSU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- ZTBRXBQEWWMNBC-UHFFFAOYSA-N triphenoxymethoxybenzene Chemical compound C=1C=CC=CC=1OC(OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 ZTBRXBQEWWMNBC-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/315—Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE787136D BE787136A (fr) | 1971-08-03 | Procede de preparation d'orthocarbonates | |
| DE2138727A DE2138727C3 (de) | 1971-08-03 | 1971-08-03 | Verfahren zur Herstellung von Orthokohlensäureestern |
| US00272224A US3857897A (en) | 1971-08-03 | 1972-07-17 | Process for the production of orthocarbonic acid esters |
| GB3538172A GB1336099A (en) | 1971-08-03 | 1972-07-20 | Process for the production of orthocarbonic acid esters |
| CH1137372A CH573390A5 (cg-RX-API-DMAC7.html) | 1971-08-03 | 1972-07-31 | |
| IT27759/72A IT963638B (it) | 1971-08-03 | 1972-08-01 | Processo per la produzione di este ri orto carbonici |
| NL7210663A NL7210663A (cg-RX-API-DMAC7.html) | 1971-08-03 | 1972-08-03 | |
| FR7228096A FR2148251B1 (cg-RX-API-DMAC7.html) | 1971-08-03 | 1972-08-03 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2138727A DE2138727C3 (de) | 1971-08-03 | 1971-08-03 | Verfahren zur Herstellung von Orthokohlensäureestern |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2138727A1 DE2138727A1 (de) | 1973-02-15 |
| DE2138727B2 DE2138727B2 (de) | 1978-08-10 |
| DE2138727C3 true DE2138727C3 (de) | 1979-04-05 |
Family
ID=5815616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2138727A Expired DE2138727C3 (de) | 1971-08-03 | 1971-08-03 | Verfahren zur Herstellung von Orthokohlensäureestern |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3857897A (cg-RX-API-DMAC7.html) |
| BE (1) | BE787136A (cg-RX-API-DMAC7.html) |
| CH (1) | CH573390A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2138727C3 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2148251B1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1336099A (cg-RX-API-DMAC7.html) |
| IT (1) | IT963638B (cg-RX-API-DMAC7.html) |
| NL (1) | NL7210663A (cg-RX-API-DMAC7.html) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5268008A (en) * | 1982-12-27 | 1993-12-07 | Union Oil Company Of California | Hydrocarbon fuel composition |
| US5290325A (en) * | 1990-02-28 | 1994-03-01 | Union Oil Company Of California | Hydrocarbon fuel composition containing alpha-ketocarboxylate additive |
| US6177389B1 (en) * | 1997-04-24 | 2001-01-23 | The Procter & Gamble Company | Detergent compositions comprising orthocarbonate pro-fragrances |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2527494A (en) * | 1946-12-21 | 1950-10-24 | Gen Aniline & Film Corp | Process for preparation of orthoformic esters |
| US2567927A (en) * | 1949-02-04 | 1951-09-18 | American Cyanamid Co | Aliphatic orthoformic esters |
| US2611787A (en) * | 1951-05-19 | 1952-09-23 | Minnesota Mining & Mfg | Fluorocarbon ortho esters |
| US3306939A (en) * | 1956-12-05 | 1967-02-28 | Marion E Hill | Orthoesters of 2,2,2-trinitroethanol |
| US3388147A (en) * | 1965-12-09 | 1968-06-11 | Navy Usa | 2-fluoro-2, 2-dinitroethyl carbonates and production thereof |
| US3354100A (en) * | 1966-10-03 | 1967-11-21 | Union Carbide Corp | Polyurethanes prepared from reaction products of polyoxyalkylene polyols and orthoesters |
-
0
- BE BE787136D patent/BE787136A/xx unknown
-
1971
- 1971-08-03 DE DE2138727A patent/DE2138727C3/de not_active Expired
-
1972
- 1972-07-17 US US00272224A patent/US3857897A/en not_active Expired - Lifetime
- 1972-07-20 GB GB3538172A patent/GB1336099A/en not_active Expired
- 1972-07-31 CH CH1137372A patent/CH573390A5/xx not_active IP Right Cessation
- 1972-08-01 IT IT27759/72A patent/IT963638B/it active
- 1972-08-03 NL NL7210663A patent/NL7210663A/xx not_active Application Discontinuation
- 1972-08-03 FR FR7228096A patent/FR2148251B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1336099A (en) | 1973-11-07 |
| DE2138727A1 (de) | 1973-02-15 |
| DE2138727B2 (de) | 1978-08-10 |
| BE787136A (fr) | 1973-02-05 |
| FR2148251B1 (cg-RX-API-DMAC7.html) | 1976-03-12 |
| IT963638B (it) | 1974-01-21 |
| NL7210663A (cg-RX-API-DMAC7.html) | 1973-02-06 |
| CH573390A5 (cg-RX-API-DMAC7.html) | 1976-03-15 |
| FR2148251A1 (cg-RX-API-DMAC7.html) | 1973-03-11 |
| US3857897A (en) | 1974-12-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2445862B1 (de) | Herstellung von substituierten 2-fluoracrylsäurederivaten | |
| EP0027189A1 (de) | Derivat des 2.5-Diketopiperazines, Verfahren zu seiner Herstellung und seine Verwendung | |
| DE2138727C3 (de) | Verfahren zur Herstellung von Orthokohlensäureestern | |
| DE2126148A1 (en) | Prepn of uracil derivs - useful as plant - protection agents and their inters | |
| DE2835157A1 (de) | Verfahren zur herstellung von n-substituierten alpha -halogenacetaniliden | |
| DE2320040A1 (de) | Verfahren zur herstellung von 7acylamino-desacetoxy-cephalosporansaeureester | |
| CH620930A5 (cg-RX-API-DMAC7.html) | ||
| EP0782991B1 (de) | Verfahren zur Herstellung von 2-substituierten 5-Chlorimidazol-4-carbaldehyden | |
| EP0435824A1 (de) | Verfahren zur Herstellung von Isothiocyanaten | |
| DE2624360A1 (de) | Verfahren zur herstellung von gegebenenfalls substituiertem 3-phenoxybenzaldehyd | |
| DE69611380T2 (de) | Verfahren zur herstellung von dioxoazabiclohexanderivaten | |
| DE2054342A1 (de) | Neue 1,2,4-Oxdiazole | |
| DE3829957A1 (de) | Verfahren zur herstellung von oxyguanidinen | |
| DE2351556C2 (de) | Verfahren zur Herstellung von N-Halogenformyl-carbamidsäurehalogeniden | |
| DE3122261C2 (cg-RX-API-DMAC7.html) | ||
| DE69203856T2 (de) | Verfahren zur Herstellung von 1,3A,8-Trimethyl-1,2,3,3A,8,8A-HEXAHYDROPYROLO(2,3-B)INDOL-5(3AS,8AR)-HEPTYLCARBAMAT. | |
| DE1932297A1 (de) | Verfahren zur Herstellung von Benzimidazol-2-carbaminsaeureestern | |
| DE3634927A1 (de) | Verfahren zur herstellung von sulfonylisothioharnstoffen | |
| DE2942195C2 (cg-RX-API-DMAC7.html) | ||
| DE2002065A1 (de) | Verfahren zur-Herstellung von Sulfimiden | |
| DE2922374A1 (de) | Verfahren zur herstellung von benzoxanthen- und benzothioxanthenfarbstoffen | |
| AT274802B (de) | Verfahren zur Herstellung von Indolderivaten | |
| DE1934227A1 (de) | Neue Iminokohlensaeureester-Derivate | |
| DE2038526A1 (de) | Verfahren zur Herstellung von organischen Isocyanaten | |
| DE2138726A1 (de) | Verfahren zur herstellung von spirocyclischen orthokohlensaeureestern |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHV | Ceased/renunciation |