DE1518308C3 - Verfahren zur Herstellung von AmmonJum-O-alkylcarbonaten und -thiolcarbonaten - Google Patents
Verfahren zur Herstellung von AmmonJum-O-alkylcarbonaten und -thiolcarbonatenInfo
- Publication number
- DE1518308C3 DE1518308C3 DE19651518308 DE1518308A DE1518308C3 DE 1518308 C3 DE1518308 C3 DE 1518308C3 DE 19651518308 DE19651518308 DE 19651518308 DE 1518308 A DE1518308 A DE 1518308A DE 1518308 C3 DE1518308 C3 DE 1518308C3
- Authority
- DE
- Germany
- Prior art keywords
- carbon
- carbonates
- tertiary amine
- alkanol
- methanol
- 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 17
- -1 thiol carbonates Chemical class 0.000 title claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 40
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 32
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 claims description 24
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 20
- 150000003512 tertiary amines Chemical class 0.000 claims description 18
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 17
- 239000001569 carbon dioxide Substances 0.000 claims description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 11
- IJCVBMSXIPFVLH-UHFFFAOYSA-N [C].S=O Chemical compound [C].S=O IJCVBMSXIPFVLH-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- OWSBHFWSKFIEGF-UHFFFAOYSA-M sodium;methyl carbonate Chemical compound [Na+].COC([O-])=O OWSBHFWSKFIEGF-UHFFFAOYSA-M 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000012973 diazabicyclooctane Substances 0.000 description 2
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- BCWWAXYNZMBSPL-UHFFFAOYSA-N CC[N+](CC)(CC)OCOC([O-])=O Chemical compound CC[N+](CC)(CC)OCOC([O-])=O BCWWAXYNZMBSPL-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- DXHPZXWIPWDXHJ-UHFFFAOYSA-N carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- BWZVWVOEWUSVMS-UHFFFAOYSA-N n,n-dimethylmethanamine;methanol Chemical compound OC.CN(C)C BWZVWVOEWUSVMS-UHFFFAOYSA-N 0.000 description 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/04—Preparation of esters of carbonic or haloformic acids from carbon dioxide or inorganic carbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37240964A | 1964-06-03 | 1964-06-03 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1518308A1 DE1518308A1 (de) | 1969-07-24 |
| DE1518308B2 DE1518308B2 (de) | 1974-07-11 |
| DE1518308C3 true DE1518308C3 (de) | 1975-03-06 |
Family
ID=23467985
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651518308 Expired DE1518308C3 (de) | 1964-06-03 | 1965-05-26 | Verfahren zur Herstellung von AmmonJum-O-alkylcarbonaten und -thiolcarbonaten |
| DE19681768458 Granted DE1768458A1 (de) | 1964-06-03 | 1968-05-15 | Verfahren zur Herstellung von Dialkylcarbonaten aus einer Ammoniumverbindung eines Kohlensaeurehalbesters |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681768458 Granted DE1768458A1 (de) | 1964-06-03 | 1968-05-15 | Verfahren zur Herstellung von Dialkylcarbonaten aus einer Ammoniumverbindung eines Kohlensaeurehalbesters |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE663796A (cg-RX-API-DMAC7.html) |
| DE (2) | DE1518308C3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES311889A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1061675A (cg-RX-API-DMAC7.html) |
| NL (1) | NL6506759A (cg-RX-API-DMAC7.html) |
-
1965
- 1965-03-25 GB GB1268765A patent/GB1061675A/en not_active Expired
- 1965-04-14 ES ES0311889A patent/ES311889A1/es not_active Expired
- 1965-05-12 BE BE663796D patent/BE663796A/xx unknown
- 1965-05-26 DE DE19651518308 patent/DE1518308C3/de not_active Expired
- 1965-05-28 NL NL6506759A patent/NL6506759A/xx unknown
-
1968
- 1968-05-15 DE DE19681768458 patent/DE1768458A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ES311889A1 (es) | 1965-08-16 |
| DE1518308B2 (de) | 1974-07-11 |
| BE663796A (cg-RX-API-DMAC7.html) | 1965-09-01 |
| DE1768458B2 (cg-RX-API-DMAC7.html) | 1974-05-16 |
| GB1061675A (en) | 1967-03-15 |
| DE1768458A1 (de) | 1972-01-05 |
| DE1768458C3 (cg-RX-API-DMAC7.html) | 1974-12-19 |
| DE1518308A1 (de) | 1969-07-24 |
| NL6506759A (cg-RX-API-DMAC7.html) | 1965-12-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3723354A1 (de) | Sulfatierte hydroxy-mischether, verfahren zu ihrer herstellung und ihre verwendung | |
| EP0185882B1 (de) | Verfahren zur Herstellung von optisch aktivem 1-Benzyl-3,4-bis-(diphenylphosphino)-pyrrolidin | |
| DE1518308C3 (de) | Verfahren zur Herstellung von AmmonJum-O-alkylcarbonaten und -thiolcarbonaten | |
| DE1493673C3 (de) | Verfahren zur Herstellung von grenzflächenaktiven Aminoalkyloxyalkanmono- und -dlsuHonaten | |
| DE602218C (de) | Verfahren zur Darstellung von Pyridylhydantoinen | |
| DE2362396C2 (de) | 3-Methyl-10-methylen-2,9-dioxatricyclo[4,3,1,0↑3↑,↑7↑] decane | |
| DE1936419B2 (cg-RX-API-DMAC7.html) | ||
| DE1962261C3 (de) | Verfahren zur Herstellung von 2,6- Bis-(diäthanolamino)-4,8-dipiperidinopyrimido[5,4-d]pyrimidin | |
| DE2849993A1 (de) | Verfahren zur abtrennung und gewinnung von 1,4-diazabicyclo eckige klammer auf 2.2.2 eckige klammer zu octan | |
| DE2112778B2 (de) | Verfahren zur Herstellung von 2-CyBn-S^Ae-IeITaChIOr- bzw. brombenzoesäurealkylestern | |
| DE68902000T2 (de) | Verfahren zur herstellung von orthosubstituiertem monobromiertem phenolderivat. | |
| DE2646884C3 (de) | Verfahren zur Herstellung von Schwefelsäurediamiden | |
| DE69112077T2 (de) | Verfahren zur herstellung von ethanolamid-alkoxylaten. | |
| DE2003043C3 (de) | Verfahren zur Herstellung von 2,6-Bis-(diäthanolamino)-4,8-di- piperidino-pyrimido [5,4d] pyrimidin | |
| AT302340B (de) | Verfahren zur Herstellung von 1,2-Di-N-morpholinoäthan | |
| DE961086C (de) | Verfahren zur Herstellung von Oxazolidonen-(2) | |
| DE1178085B (de) | Verfahren zur Herstellung von 2,3,5,6-Tetra-cyan-1,4-dithiin | |
| DE956046C (de) | Verfahren zur Herstellung von Diphenylamin und kernalkylsubstituierten Diphenylaminen | |
| DE1105866B (de) | Verfahren zur Herstellung von N, N'-substituierten Harnstoff-verbindungen | |
| DE2024805C3 (de) | Verfahren zur Herstellung von 2-Amino-3-chlorpyrazin | |
| AT239252B (de) | Verfahren zur partiellen oder vollständigen Carbamylierung von zweiwertigen Alkoholen oder von deren partiell O-substituierten Derivaten | |
| AT319960B (de) | Verfahren zur Herstellung von neuen Pyridazinverbindungen | |
| DE2653398A1 (de) | Verfahren zur herstellung von 5-fluor-uracil-derivaten | |
| DE2221792C3 (de) | Verfahren zur Herstellung von 4-Methyl-l-penten durch Dimerisieren von Propylen | |
| DE1173437B (de) | Verfahren zur Herstellung von Sulfaminsaeure |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |