DD208797A5 - Herstellung von nitritestern - Google Patents
Herstellung von nitritestern Download PDFInfo
- Publication number
- DD208797A5 DD208797A5 DD82243672A DD24367282A DD208797A5 DD 208797 A5 DD208797 A5 DD 208797A5 DD 82243672 A DD82243672 A DD 82243672A DD 24367282 A DD24367282 A DD 24367282A DD 208797 A5 DD208797 A5 DD 208797A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- item
- reaction
- alcohol
- nitrogen
- reaction zone
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 7
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 title description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims abstract description 185
- 238000006243 chemical reaction Methods 0.000 claims abstract description 80
- 238000000034 method Methods 0.000 claims abstract description 72
- 230000008569 process Effects 0.000 claims abstract description 56
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims abstract description 35
- -1 aliphatic alcohols Chemical class 0.000 claims abstract description 34
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 29
- 239000006227 byproduct Substances 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 76
- 150000002148 esters Chemical class 0.000 claims description 28
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 23
- 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 22
- 239000002253 acid Substances 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 11
- 239000007789 gas Substances 0.000 claims description 8
- 239000003701 inert diluent Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 238000012856 packing Methods 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 150000002826 nitrites Chemical class 0.000 abstract description 18
- 239000012808 vapor phase Substances 0.000 abstract description 9
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 description 56
- 229960003753 nitric oxide Drugs 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 22
- 229910052760 oxygen Inorganic materials 0.000 description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 15
- 239000001301 oxygen Substances 0.000 description 15
- 229910001220 stainless steel Inorganic materials 0.000 description 15
- 239000010935 stainless steel Substances 0.000 description 15
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 14
- 229910017604 nitric acid Inorganic materials 0.000 description 14
- 238000010517 secondary reaction Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 229910001868 water Inorganic materials 0.000 description 12
- 239000003085 diluting agent Substances 0.000 description 11
- LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 description 8
- 239000007791 liquid phase Substances 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 125000003158 alcohol group Chemical group 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 238000010276 construction Methods 0.000 description 6
- 229910001882 dioxygen Inorganic materials 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- QQZWEECEMNQSTG-UHFFFAOYSA-N Ethyl nitrite Chemical compound CCON=O QQZWEECEMNQSTG-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical group 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 229910017464 nitrogen compound Inorganic materials 0.000 description 4
- 150000002830 nitrogen compounds Chemical class 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 230000008016 vaporization Effects 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 239000010963 304 stainless steel Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229910000589 SAE 304 stainless steel Inorganic materials 0.000 description 2
- 229910000746 Structural steel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N Nitrogen oxide(NO) Natural products O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 230000002292 Radical scavenging effect Effects 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000002816 fuel additive Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BLLFVUPNHCTMSV-UHFFFAOYSA-N methyl nitrite Chemical compound CON=O BLLFVUPNHCTMSV-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 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 |
|---|---|---|---|
| US30720181A | 1981-09-30 | 1981-09-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD208797A5 true DD208797A5 (de) | 1984-04-11 |
Family
ID=23188690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD82243672A DD208797A5 (de) | 1981-09-30 | 1982-09-30 | Herstellung von nitritestern |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0076217A3 (enExample) |
| JP (1) | JPS5869840A (enExample) |
| KR (1) | KR870001853B1 (enExample) |
| AR (1) | AR231270A1 (enExample) |
| AU (1) | AU558557B2 (enExample) |
| BR (1) | BR8205669A (enExample) |
| CA (1) | CA1189528A (enExample) |
| DD (1) | DD208797A5 (enExample) |
| ES (1) | ES8308515A1 (enExample) |
| MX (1) | MX161786A (enExample) |
| ZA (1) | ZA826927B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4908466A (en) * | 1987-09-29 | 1990-03-13 | Union Carbide Chemicals And Plastics Company Inc. | Process and reaction vessel for production of alkyl nitrite |
| DE4307192A1 (de) * | 1993-03-08 | 1994-09-15 | Bayer Ag | Verfahren zur Herstellung von C¶1¶-C¶4¶-Alkyl-nitriten |
| DE4307193A1 (de) * | 1993-03-08 | 1994-09-15 | Bayer Ag | Verfahren zur Herstellung von C¶1¶-C¶4¶-Alkyl-nitriten |
| SG71167A1 (en) | 1997-10-21 | 2000-03-21 | Ube Industries | Process for producing alkyl nitrite |
| US6844464B2 (en) | 2002-03-18 | 2005-01-18 | Ube Industries, Ltd. | Process for producing alkyl nitrite |
| CN102649760B (zh) * | 2011-02-25 | 2014-03-26 | 中国石油化工股份有限公司 | C1～c4烷基亚硝酸酯的生产方法 |
| CN103570551B (zh) * | 2012-07-25 | 2015-02-04 | 中国石油化工股份有限公司 | 一种合成草酸酯用亚硝酸酯的装置和方法 |
| WO2017133995A1 (de) | 2016-02-01 | 2017-08-10 | Basf Se | Verfahren zur herstellung von c4-c15-lactamen |
| JP7511877B2 (ja) * | 2020-06-19 | 2024-07-08 | 東京都公立大学法人 | 窒素化合物変換装置および窒素化合物変換方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2831882A (en) * | 1955-09-16 | 1958-04-22 | Du Pont | Preparation of nitrite esters |
| JPS54100312A (en) * | 1978-01-25 | 1979-08-08 | Ube Ind Ltd | Preparation of oxalic diesters |
| US4353843A (en) * | 1981-01-23 | 1982-10-12 | Union Carbide Corporation | Preparation of nitrite esters |
-
1982
- 1982-09-16 CA CA000411615A patent/CA1189528A/en not_active Expired
- 1982-09-21 ZA ZA826927A patent/ZA826927B/xx unknown
- 1982-09-27 JP JP57166757A patent/JPS5869840A/ja active Granted
- 1982-09-28 AU AU88785/82A patent/AU558557B2/en not_active Ceased
- 1982-09-28 BR BR8205669A patent/BR8205669A/pt unknown
- 1982-09-29 EP EP82401770A patent/EP0076217A3/en not_active Withdrawn
- 1982-09-29 KR KR8204400A patent/KR870001853B1/ko not_active Expired - Lifetime
- 1982-09-29 ES ES516067A patent/ES8308515A1/es not_active Expired
- 1982-09-29 AR AR290803A patent/AR231270A1/es active
- 1982-09-29 MX MX194571A patent/MX161786A/es unknown
- 1982-09-30 DD DD82243672A patent/DD208797A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6335617B2 (enExample) | 1988-07-15 |
| KR840001545A (ko) | 1984-05-07 |
| MX161786A (es) | 1990-12-27 |
| EP0076217A3 (en) | 1984-03-28 |
| AU558557B2 (en) | 1987-02-05 |
| ES516067A0 (es) | 1983-10-01 |
| AR231270A1 (es) | 1984-10-31 |
| EP0076217A2 (en) | 1983-04-06 |
| ZA826927B (en) | 1984-04-25 |
| JPS5869840A (ja) | 1983-04-26 |
| KR870001853B1 (ko) | 1987-10-17 |
| AU8878582A (en) | 1983-04-14 |
| BR8205669A (pt) | 1983-08-30 |
| ES8308515A1 (es) | 1983-10-01 |
| CA1189528A (en) | 1985-06-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |