CA1319368C - Process for the manufacture of nitric acid esters - Google Patents
Process for the manufacture of nitric acid estersInfo
- Publication number
- CA1319368C CA1319368C CA000457348A CA457348A CA1319368C CA 1319368 C CA1319368 C CA 1319368C CA 000457348 A CA000457348 A CA 000457348A CA 457348 A CA457348 A CA 457348A CA 1319368 C CA1319368 C CA 1319368C
- Authority
- CA
- Canada
- Prior art keywords
- solvent
- nitric acid
- acid
- organic
- reaction
- 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 - Fee Related
Links
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 title claims abstract description 113
- 238000000034 method Methods 0.000 title claims abstract description 66
- 238000004519 manufacturing process Methods 0.000 title description 10
- 239000002904 solvent Substances 0.000 claims abstract description 137
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 107
- 239000002253 acid Substances 0.000 claims abstract description 79
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 73
- 235000011149 sulphuric acid Nutrition 0.000 claims abstract description 73
- 239000001117 sulphuric acid Substances 0.000 claims abstract description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 58
- 238000006243 chemical reaction Methods 0.000 claims abstract description 55
- 238000006396 nitration reaction Methods 0.000 claims abstract description 42
- 150000002440 hydroxy compounds Chemical class 0.000 claims abstract description 28
- -1 alkyl nitrates Chemical class 0.000 claims abstract description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 229920001515 polyalkylene glycol Polymers 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 150000001346 alkyl aryl ethers Chemical class 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000006353 oxyethylene group Chemical group 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 2
- RQLOBLXCVODRRW-UHFFFAOYSA-N 1-butoxy-2-ethoxyethanol Chemical compound CCCCOC(O)COCC RQLOBLXCVODRRW-UHFFFAOYSA-N 0.000 claims 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 claims 1
- RDQAMPWQSKJXLE-UHFFFAOYSA-N C(CCC)OCCO.C(CC)OCCO.C(C)OCCO.COCCO Chemical compound C(CCC)OCCO.C(CC)OCCO.C(C)OCCO.COCCO RDQAMPWQSKJXLE-UHFFFAOYSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 abstract description 8
- 150000002823 nitrates Chemical class 0.000 abstract description 8
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 229920005862 polyol Polymers 0.000 abstract description 2
- 150000003077 polyols Chemical class 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 239000000047 product Substances 0.000 description 46
- 239000012071 phase Substances 0.000 description 43
- 238000003860 storage Methods 0.000 description 32
- 239000000243 solution Substances 0.000 description 25
- 238000011084 recovery Methods 0.000 description 22
- 239000000463 material Substances 0.000 description 19
- 238000006386 neutralization reaction Methods 0.000 description 19
- 239000012044 organic layer Substances 0.000 description 16
- 238000000926 separation method Methods 0.000 description 15
- 239000000758 substrate Substances 0.000 description 15
- 150000007513 acids Chemical class 0.000 description 14
- 239000006227 byproduct Substances 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- 239000000376 reactant Substances 0.000 description 11
- 239000008346 aqueous phase Substances 0.000 description 10
- 238000013019 agitation Methods 0.000 description 9
- 239000003513 alkali Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
- 235000011114 ammonium hydroxide Nutrition 0.000 description 8
- 238000010790 dilution Methods 0.000 description 8
- 239000012895 dilution Substances 0.000 description 8
- 238000004566 IR spectroscopy Methods 0.000 description 7
- AGCQZYRSTIRJFM-UHFFFAOYSA-N triethylene glycol dinitrate Chemical compound [O-][N+](=O)OCCOCCOCCO[N+]([O-])=O AGCQZYRSTIRJFM-UHFFFAOYSA-N 0.000 description 7
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000012467 final product Substances 0.000 description 5
- 238000005057 refrigeration Methods 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- LYAGTVMJGHTIDH-UHFFFAOYSA-N diethylene glycol dinitrate Chemical compound [O-][N+](=O)OCCOCCO[N+]([O-])=O LYAGTVMJGHTIDH-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZQXMBZPLNQCFKE-UHFFFAOYSA-N 2-butoxyethyl nitrate Chemical compound CCCCOCCO[N+]([O-])=O ZQXMBZPLNQCFKE-UHFFFAOYSA-N 0.000 description 3
- NNKQLUVBPJEUOR-UHFFFAOYSA-N 3-ethynylaniline Chemical compound NC1=CC=CC(C#C)=C1 NNKQLUVBPJEUOR-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- UQXKXGWGFRWILX-UHFFFAOYSA-N ethylene glycol dinitrate Chemical compound O=N(=O)OCCON(=O)=O UQXKXGWGFRWILX-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000013505 freshwater Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- 229940082615 organic nitrates used in cardiac disease Drugs 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- APMDXOLCMUOZLD-UHFFFAOYSA-N 1-nitrooxybutyl nitrate Chemical compound CCCC(O[N+]([O-])=O)O[N+]([O-])=O APMDXOLCMUOZLD-UHFFFAOYSA-N 0.000 description 1
- GDNQXPDYGNUKII-UHFFFAOYSA-N 2-ethoxyethyl nitrate Chemical compound CCOCCO[N+]([O-])=O GDNQXPDYGNUKII-UHFFFAOYSA-N 0.000 description 1
- KLSTYOFWPIMPSJ-UHFFFAOYSA-N 2-ethylbutyl nitrate Chemical compound CCC(CC)CO[N+]([O-])=O KLSTYOFWPIMPSJ-UHFFFAOYSA-N 0.000 description 1
- NKRVGWFEFKCZAP-UHFFFAOYSA-N 2-ethylhexyl nitrate Chemical class CCCCC(CC)CO[N+]([O-])=O NKRVGWFEFKCZAP-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 230000009194 climbing Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- HLYOOCIMLHNMOG-UHFFFAOYSA-N cyclohexyl nitrate Chemical compound [O-][N+](=O)OC1CCCCC1 HLYOOCIMLHNMOG-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- UEFBRXQBUTYIJI-UHFFFAOYSA-N decyl nitrate Chemical compound CCCCCCCCCCO[N+]([O-])=O UEFBRXQBUTYIJI-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229960003711 glyceryl trinitrate Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- MZVGTZNDBKNLAH-UHFFFAOYSA-N oxolan-2-ylmethyl nitrate Chemical compound [O-][N+](=O)OCC1CCCO1 MZVGTZNDBKNLAH-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- HKSZLNNOFSGOKW-HMWZOHBLSA-N staurosporine Chemical compound C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1[C@@H]1C[C@H](NC)[C@H](OC)[C@@]4(C)O1 HKSZLNNOFSGOKW-HMWZOHBLSA-N 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000006228 supernatant Substances 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
- C07C201/02—Preparation of esters of nitric acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ZA83/4643 | 1983-06-24 | ||
| ZA834643 | 1983-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1319368C true CA1319368C (en) | 1993-06-22 |
Family
ID=25576783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000457348A Expired - Fee Related CA1319368C (en) | 1983-06-24 | 1984-06-25 | Process for the manufacture of nitric acid esters |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4853157A (enExample) |
| EP (1) | EP0129995B2 (enExample) |
| JP (1) | JPS6064948A (enExample) |
| AU (1) | AU571530B2 (enExample) |
| BR (1) | BR8402993A (enExample) |
| CA (1) | CA1319368C (enExample) |
| DE (1) | DE3463647D1 (enExample) |
| GB (1) | GB2142016B (enExample) |
| MW (1) | MW1084A1 (enExample) |
| NO (1) | NO159789C (enExample) |
| NZ (1) | NZ208387A (enExample) |
| ZW (1) | ZW8384A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5089652A (en) * | 1990-01-17 | 1992-02-18 | Atlas Powder Company | Nitrate ester preparation |
| US4980000A (en) * | 1990-01-17 | 1990-12-25 | Atlas Powder Company | Nitrostarch emulsion explosives production process |
| US5051142A (en) * | 1990-01-17 | 1991-09-24 | Atlas Powder Company | Emulsion explosive containing nitrostarch |
| EP1240234B1 (en) | 1999-10-19 | 2004-12-29 | Alliant Techsystems Inc. | Polymerization of poly(glycidyl nitrate) from high purity glycidyl nitrate synthesized from glycerol |
| RU2259348C1 (ru) * | 2004-02-04 | 2005-08-27 | ФГУП "Бийский олеумный завод" | Способ получения 2-этилгексилнитрата непрерывным методом |
| WO2006056535A1 (en) * | 2004-11-25 | 2006-06-01 | Nicox S.A. | Process for preparing halogenoalkylnitrates |
| DE102005057555B3 (de) * | 2005-11-21 | 2007-05-16 | Meissner Gmbh & Co Kg Josef | Verfahren zur Herstellung von Salpetersäureestern einwertiger Alkohole |
| CN101696168B (zh) * | 2009-11-04 | 2014-08-13 | 西安万德能源化学股份有限公司 | 一种硝酸异辛酯粗产品的脱水干燥系统及工艺 |
| RU2532663C1 (ru) * | 2013-05-21 | 2014-11-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Нижегородский государственный технический университет им. Р.Е. Алексеева", НГТУ | Способ получения цетаноповышающих присадок к дизельному топливу |
| CN104892425A (zh) | 2014-03-07 | 2015-09-09 | 康宁股份有限公司 | 在流动反应器中连续合成硝酸异辛酯 |
| RU2567236C1 (ru) * | 2014-07-29 | 2015-11-10 | Федеральное государственное унитарное предприятие "Специальное конструкторско-технологическое бюро "Технолог" | Безопасный способ получения алифатических полинитратов спиртов в промышленных условиях |
| CN104557556B (zh) * | 2015-01-26 | 2017-07-18 | 大连微凯化学有限公司 | 一种生产硝酸异辛酯的装置及工艺方法 |
| GB2535234A (en) * | 2015-02-15 | 2016-08-17 | Avocet Fuel Solutions Inc | Fuel additive, fuel and method |
| RU2688690C2 (ru) * | 2017-10-31 | 2019-05-22 | Федеральное государственное унитарное предприятие "Специальное конструкторско-технологическое бюро "Технолог" | Безопасный способ получения динитратов вицинальных гликолей |
| CN107935857A (zh) * | 2017-12-11 | 2018-04-20 | 中国科学院大连化学物理研究所 | 一种硝酸异辛酯的生产方法 |
| RU2680963C1 (ru) * | 2018-06-14 | 2019-03-01 | федеральное государственное бюджетное образовательное учреждение высшего образования "Иркутский национальный исследовательский технический университет" (ФГБОУ ВО "ИРНИТУ") | Присадка к дизельному топливу комплексного действия и способ ее получения |
| CN109574849A (zh) * | 2018-12-17 | 2019-04-05 | 山东益丰生化环保股份有限公司 | 一种十六烷值改进剂的制备方法 |
| CN110683953B (zh) * | 2019-05-15 | 2021-01-15 | 中国科学院大连化学物理研究所 | 一种在微反应器中连续合成硝酸异辛酯并萃取其中残余酸的方法 |
| CN111568859B (zh) * | 2020-05-19 | 2022-07-19 | 启东市新晨企业管理咨询有限公司 | 一种硝酸甘油的外用制剂 |
| CN115677508A (zh) * | 2022-11-11 | 2023-02-03 | 万华化学集团股份有限公司 | 一种二醇单硝酸酯的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL98269C (enExample) * | 1956-02-24 | |||
| US3111538A (en) * | 1957-02-07 | 1963-11-19 | Hercules Powder Co Ltd | Continuous manufacture of explosive liquid nitric acid esters |
| US3331867A (en) * | 1961-06-08 | 1967-07-18 | Du Pont | Process for preparing tetra(di-fluoroamino)hexanediol dinitrate |
| US3408388A (en) * | 1961-07-10 | 1968-10-29 | Eastman Kodak Co | Process for preparing esters of unsaturated alcohols from monoesters of saturated 2, 2, 4-trisubstituted-1, 3-diols |
| GB1444341A (en) * | 1961-12-19 | 1976-07-28 | Secr Defence | Manufacture of nitric esters |
| DE2820890C2 (de) * | 1978-05-12 | 1986-09-25 | Josef Meissner GmbH & Co, 5000 Köln | Verfahren zur kontinuierlichen Herstellung von Salpetersäureestern mehrwertiger Alkohole |
| US4352699A (en) * | 1981-06-01 | 1982-10-05 | Hercules Incorporated | Co-nitrating trimetholethane and diethylene glycol |
-
1984
- 1984-06-04 DE DE8484303752T patent/DE3463647D1/de not_active Expired
- 1984-06-04 GB GB08414201A patent/GB2142016B/en not_active Expired
- 1984-06-04 AU AU28990/84A patent/AU571530B2/en not_active Ceased
- 1984-06-04 EP EP84303752A patent/EP0129995B2/en not_active Expired - Lifetime
- 1984-06-05 NZ NZ208387A patent/NZ208387A/en unknown
- 1984-06-07 MW MW10/84A patent/MW1084A1/xx unknown
- 1984-06-11 ZW ZW83/84A patent/ZW8384A1/xx unknown
- 1984-06-14 US US06/620,624 patent/US4853157A/en not_active Expired - Fee Related
- 1984-06-19 BR BR8402993A patent/BR8402993A/pt not_active IP Right Cessation
- 1984-06-22 NO NO84842526A patent/NO159789C/no unknown
- 1984-06-22 JP JP59127731A patent/JPS6064948A/ja active Granted
- 1984-06-25 CA CA000457348A patent/CA1319368C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0129995A2 (en) | 1985-01-02 |
| GB8414201D0 (en) | 1984-07-11 |
| NO159789C (no) | 1989-02-08 |
| MW1084A1 (en) | 1986-03-12 |
| NZ208387A (en) | 1987-03-31 |
| BR8402993A (pt) | 1985-05-28 |
| GB2142016A (en) | 1985-01-09 |
| JPS6064948A (ja) | 1985-04-13 |
| EP0129995A3 (en) | 1985-06-12 |
| AU571530B2 (en) | 1988-04-21 |
| DE3463647D1 (en) | 1987-06-19 |
| GB2142016B (en) | 1986-07-23 |
| US4853157A (en) | 1989-08-01 |
| NO842526L (no) | 1984-12-27 |
| NO159789B (no) | 1988-10-31 |
| EP0129995B1 (en) | 1987-05-13 |
| EP0129995B2 (en) | 1993-09-08 |
| JPH0422896B2 (enExample) | 1992-04-20 |
| AU2899084A (en) | 1985-01-03 |
| ZW8384A1 (en) | 1986-01-22 |
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