JPS6247867B2 - - Google Patents
Info
- Publication number
- JPS6247867B2 JPS6247867B2 JP57006218A JP621882A JPS6247867B2 JP S6247867 B2 JPS6247867 B2 JP S6247867B2 JP 57006218 A JP57006218 A JP 57006218A JP 621882 A JP621882 A JP 621882A JP S6247867 B2 JPS6247867 B2 JP S6247867B2
- Authority
- JP
- Japan
- Prior art keywords
- nitrite
- nitrogen
- molar ratio
- nitrogen oxide
- ethanol
- 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
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 145
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 80
- 238000000034 method Methods 0.000 claims description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 43
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 33
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
- 239000003085 diluting agent Substances 0.000 claims description 19
- 239000011261 inert gas Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 12
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 10
- QQZWEECEMNQSTG-UHFFFAOYSA-N Ethyl nitrite Chemical compound CCON=O QQZWEECEMNQSTG-UHFFFAOYSA-N 0.000 claims description 10
- 229910001882 dioxygen Inorganic materials 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- BLLFVUPNHCTMSV-UHFFFAOYSA-N methyl nitrite Chemical compound CON=O BLLFVUPNHCTMSV-UHFFFAOYSA-N 0.000 claims description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
- 239000001569 carbon dioxide Substances 0.000 claims description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical group [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 description 50
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 42
- 229960003753 nitric oxide Drugs 0.000 description 34
- -1 nitrite ester Chemical class 0.000 description 33
- 238000004519 manufacturing process Methods 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 229910001868 water Inorganic materials 0.000 description 15
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 14
- 150000002826 nitrites Chemical class 0.000 description 14
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 13
- 239000007789 gas Substances 0.000 description 13
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 12
- 229910017604 nitric acid Inorganic materials 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 10
- 239000007791 liquid phase Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 239000010963 304 stainless steel Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 229910000589 SAE 304 stainless steel Inorganic materials 0.000 description 5
- 125000003158 alcohol group Chemical group 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 4
- LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 description 2
- 150000002830 nitrogen compounds Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N Nitrogen oxide(NO) Natural products O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LRMHVVPPGGOAJQ-UHFFFAOYSA-N methyl nitrate Chemical group CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 description 1
- 210000002445 nipple Anatomy 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/04—Preparation of esters of nitrous acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C203/00—Esters of nitric or nitrous acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22779881A | 1981-01-23 | 1981-01-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57139041A JPS57139041A (en) | 1982-08-27 |
| JPS6247867B2 true JPS6247867B2 (enrdf_load_stackoverflow) | 1987-10-09 |
Family
ID=22854506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57006218A Granted JPS57139041A (en) | 1981-01-23 | 1982-01-20 | Manufacture of nitrous acid ester |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS57139041A (enrdf_load_stackoverflow) |
| KR (1) | KR870000802B1 (enrdf_load_stackoverflow) |
| ZA (1) | ZA82103B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102219698B (zh) * | 2010-04-15 | 2014-04-23 | 中国石油化工股份有限公司 | 生产c1～c4烷基亚硝酸酯的方法 |
-
1982
- 1982-01-07 ZA ZA82103A patent/ZA82103B/xx unknown
- 1982-01-20 JP JP57006218A patent/JPS57139041A/ja active Granted
- 1982-01-22 KR KR8200267A patent/KR870000802B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| KR870000802B1 (ko) | 1987-04-20 |
| ZA82103B (en) | 1982-11-24 |
| KR830008982A (ko) | 1983-12-16 |
| JPS57139041A (en) | 1982-08-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4353843A (en) | Preparation of nitrite esters | |
| US4879401A (en) | Process for removal of impurities in alkyl nitrite formation | |
| EP0310191B1 (en) | Process and reaction vessel for production of alkyl nitrite | |
| EP1346976A1 (en) | Process for producing alkyl nitrite | |
| EP2491000B1 (en) | Process for the manufacture of nitrated hydrocarbons | |
| US4461909A (en) | Process for continuously preparing a diester of oxalic acid | |
| JP2007105668A (ja) | 気液反応方法及びそのための装置 | |
| JP2931751B2 (ja) | 亜硝酸アルキルの連続的製造のための方法 | |
| CA1189528A (en) | Preparation of nitrite esters | |
| US4629806A (en) | Vapor state formation of diesters of oxalic acid | |
| JPS6247867B2 (enrdf_load_stackoverflow) | ||
| RU2279424C2 (ru) | Способ получения соединения (мет)акролеина или (мет)акриловой кислоты | |
| RU2049086C1 (ru) | Способ получения метанола | |
| EP0057629B1 (en) | Vapor state process for the preparation of diesters of oxalic acid | |
| Peters et al. | Methacrylonitrile and acrylonitrile | |
| Bachman et al. | Nitration studies. XVI. Conversion of nitrite and nitrate esters in nitro alkanes | |
| GB2143526A (en) | Preparing 3,3,3-trifluoro-2-trifluoromethylpropene | |
| WO2005113430A1 (en) | Concurrent sulfur dioxide oxidation process and its use in manufacture of tetrabromophthalic anhydride | |
| JP2958351B2 (ja) | モノメチルヒドラジンの水溶液の合成方法 | |
| JPS5879948A (ja) | イソブチルアルデヒドからメタクリル酸を製造する方法 | |
| US2805122A (en) | Process for producing ammonium nitrite | |
| US3649191A (en) | Process for manufacture of nitrosyl chloride | |
| US4487988A (en) | Nitration of organic compounds | |
| CA2117017A1 (en) | Process for the preparation of c1-c4-alkyl nitrites | |
| EP0060718B1 (en) | Continuous process for the production of methyl formate by the chromium catalysed liquid phase oxidation of methanol |