AU651808B2 - Nitrate ester preparation - Google Patents
Nitrate ester preparation Download PDFInfo
- Publication number
- AU651808B2 AU651808B2 AU71691/91A AU7169191A AU651808B2 AU 651808 B2 AU651808 B2 AU 651808B2 AU 71691/91 A AU71691/91 A AU 71691/91A AU 7169191 A AU7169191 A AU 7169191A AU 651808 B2 AU651808 B2 AU 651808B2
- Authority
- AU
- Australia
- Prior art keywords
- nitric acid
- nitrate
- published
- carbon atoms
- organic
- 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.)
- Ceased
Links
- 229910002651 NO3 Inorganic materials 0.000 title claims description 46
- -1 Nitrate ester Chemical class 0.000 title claims description 46
- 238000002360 preparation method Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 64
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical group O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 47
- 229910017604 nitric acid Inorganic materials 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 35
- 150000002823 nitrates Chemical class 0.000 claims description 34
- 238000006396 nitration reaction Methods 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 239000003960 organic solvent Substances 0.000 claims description 26
- 239000011541 reaction mixture Substances 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 230000000802 nitrating effect Effects 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000012266 salt solution Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 125000001931 aliphatic group Chemical group 0.000 claims 4
- 239000003513 alkali Substances 0.000 claims 4
- 150000002894 organic compounds Chemical class 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 150000008282 halocarbons Chemical group 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 47
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 3
- TXPURXMTKXRAMV-UHFFFAOYSA-N 2-[2-[2-(2-nitrooxyethoxy)ethoxy]ethoxy]ethyl nitrate Chemical compound [O-][N+](=O)OCCOCCOCCOCCO[N+]([O-])=O TXPURXMTKXRAMV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical compound [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000003440 toxic substance 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US466221 | 1990-01-17 | ||
| US07/466,221 US5089652A (en) | 1990-01-17 | 1990-01-17 | Nitrate ester preparation |
| PCT/US1991/000030 WO1991010640A1 (en) | 1990-01-17 | 1991-01-10 | Nitrate ester preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7169191A AU7169191A (en) | 1991-08-05 |
| AU651808B2 true AU651808B2 (en) | 1994-08-04 |
Family
ID=23850957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU71691/91A Ceased AU651808B2 (en) | 1990-01-17 | 1991-01-10 | Nitrate ester preparation |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5089652A (https=) |
| EP (1) | EP0471043A1 (https=) |
| JP (1) | JPH04503961A (https=) |
| AU (1) | AU651808B2 (https=) |
| BR (1) | BR9103969A (https=) |
| CA (1) | CA2050288A1 (https=) |
| NZ (1) | NZ236788A (https=) |
| WO (1) | WO1991010640A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001029111A1 (en) | 1999-10-19 | 2001-04-26 | Alliant Techsystems Inc. | Polymerization of poly(glycidyl nitrate) from high purity glycidyl nitrate synthesized from glycerol |
| DE102004007706A1 (de) * | 2004-02-16 | 2005-08-25 | Dynamit Nobel Gmbh Explosivstoff- Und Systemtechnik | Verfahren zur Herstellung von flüssigen Nitratestern |
| JP2008521770A (ja) | 2004-11-25 | 2008-06-26 | ニコックス エス エイ | ハロゲノアルキルナイトレートの製造方法 |
| PL2222628T3 (pl) * | 2007-12-20 | 2012-12-31 | Dsm Fine Chemicals Austria Nfg Gmbh & Co Kg | Tworzenie estrów azotanowych w mikroreaktorach i milireaktorach z zastosowaniem ciągłej ekstrakcji produktu w układzie przepływu burzliwego |
| GB2535234A (en) * | 2015-02-15 | 2016-08-17 | Avocet Fuel Solutions Inc | Fuel additive, fuel and method |
| US10562873B1 (en) * | 2018-12-07 | 2020-02-18 | Northrop Grumman Innovation Systems, Inc. | Methods of producing glycidyl nitrate |
| US20250361627A1 (en) * | 2022-11-30 | 2025-11-27 | Yale University | Electrochemical Alcohol Nitration Systems and Methods |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1660651A (en) * | 1926-12-31 | 1928-02-28 | Du Pont | Nitration process |
| US1936020A (en) * | 1928-12-03 | 1933-11-21 | Hough Arthur | Method of nitrating organic substances |
| US2957021A (en) * | 1959-01-20 | 1960-10-18 | Chattanooga Medicine Co | Nitrate esters of amino alcohols and salts thereof |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1426313A (en) * | 1922-08-15 | Hermann oehme | ||
| US541899A (en) * | 1895-07-02 | Bruno thieme | ||
| US879899A (en) * | 1907-09-11 | 1908-02-25 | Du Pont Powder Co | Process of obtaining dinitroglycerin, &c. |
| US1206223A (en) * | 1914-10-22 | 1916-11-28 | Arthur Hough | Process of making glycol dinitrate for explosive uses. |
| US1371215A (en) * | 1917-07-14 | 1921-03-15 | Commercial Res Company | Explosive and process of making explosives |
| US1901003A (en) * | 1927-02-05 | 1933-03-14 | Karl Schmid | Process of washing nitroglycerine and similar esters |
| US1912399A (en) * | 1928-05-10 | 1933-06-06 | Hercules Powder Co Ltd | Method of purifying aliphatic organic nitrates |
| US1868388A (en) * | 1928-12-03 | 1932-07-19 | Hough Arthur | Explosive |
| US1852041A (en) * | 1929-09-14 | 1932-04-05 | Hercules Powder Co Ltd | Method of purifying nitrated polyhydric alcohols |
| US2254352A (en) * | 1937-12-08 | 1941-09-02 | Standard Oil Dev Co | Process for the manufacture of alkyl nitrates |
| NL55185C (https=) * | 1939-03-30 | |||
| US2294592A (en) * | 1940-04-29 | 1942-09-01 | Trojan Powder Co | Preparation and purification of nitrated pentaerythritols |
| US2389228A (en) * | 1943-04-14 | 1945-11-20 | Trojan Powder Co | Preparation of tripentaerythritol octanitrate |
| US2678946A (en) * | 1944-12-30 | 1954-05-18 | Us Navy | Process of preparing nitroxy alkyl nitramines |
| US2461582A (en) * | 1944-12-30 | 1949-02-15 | Honorary Advisory Council Sci | Nitramines and their preparation |
| US2485855A (en) * | 1944-12-30 | 1949-10-25 | Us Seeretary Of The Navy | Nitramines |
| US2978484A (en) * | 1951-01-06 | 1961-04-04 | Aerojet General Co | 2, 2-dinitropropane-1, 3-dinitrate |
| US3000928A (en) * | 1958-02-18 | 1961-09-19 | Aerojet General Co | Polynitro nitrate compounds and method of preparation |
| US3423256A (en) * | 1968-01-08 | 1969-01-21 | Commercial Solvents Corp | Explosives containing an impact-sensitive liquid nitrated polyol and trimethylolethane trinitrate and process of conitrating mixtures of polyols and trimethylol ethane |
| US3711345A (en) * | 1970-08-18 | 1973-01-16 | Du Pont | Chemical foaming of water-bearing explosives |
| US3899374A (en) * | 1974-03-29 | 1975-08-12 | Dow Chemical Co | Calcium nitrate explosive composition |
| US4381958A (en) * | 1980-08-07 | 1983-05-03 | Hercules Incorporated | Triaminoguanidine nitrate-containing propellants |
| US4371408A (en) * | 1980-10-27 | 1983-02-01 | Atlas Powder Company | Low water emulsion explosive compositions optionally containing inert salts |
| US4383873A (en) * | 1980-10-27 | 1983-05-17 | Atlas Powder Company | Sensitive low water emulsion explosive compositions |
| US4352699A (en) * | 1981-06-01 | 1982-10-05 | Hercules Incorporated | Co-nitrating trimetholethane and diethylene glycol |
| US4457791A (en) * | 1982-06-25 | 1984-07-03 | The United States Of America As Represented By The Secretary Of The Navy | New plasticizer for nitropolymers |
| US4450110A (en) * | 1983-03-24 | 1984-05-22 | Hercules Incorporated | Azido nitramine |
| US4522756A (en) * | 1983-03-28 | 1985-06-11 | Rockwell International Corporation | Alkyl, azido, nitro ethers and method of preparation |
| AU571530B2 (en) * | 1983-06-24 | 1988-04-21 | Aeci Limited | Manufacture of nitric acid esters |
| US4523967A (en) * | 1984-08-06 | 1985-06-18 | Hercules Incorporated | Invert emulsion explosives containing a one-component oil phase |
| US4726919A (en) * | 1985-05-06 | 1988-02-23 | Morton Thiokol, Inc. | Method of preparing a non-feathering nitramine propellant |
| US4761250A (en) * | 1985-08-09 | 1988-08-02 | Rockwell International Corporation | Process for preparing 1,5-diazido-3-nitrazapentane |
| US4664729A (en) * | 1986-04-14 | 1987-05-12 | Independent Explosives Co. Of Penna. | Water-in-oil explosive emulsion composition |
-
1990
- 1990-01-17 US US07/466,221 patent/US5089652A/en not_active Expired - Fee Related
-
1991
- 1991-01-10 JP JP3502965A patent/JPH04503961A/ja active Pending
- 1991-01-10 WO PCT/US1991/000030 patent/WO1991010640A1/en not_active Ceased
- 1991-01-10 EP EP91902460A patent/EP0471043A1/en not_active Withdrawn
- 1991-01-10 BR BR919103969A patent/BR9103969A/pt not_active Application Discontinuation
- 1991-01-10 AU AU71691/91A patent/AU651808B2/en not_active Ceased
- 1991-01-10 CA CA002050288A patent/CA2050288A1/en not_active Abandoned
- 1991-01-16 NZ NZ236788A patent/NZ236788A/xx unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1660651A (en) * | 1926-12-31 | 1928-02-28 | Du Pont | Nitration process |
| US1936020A (en) * | 1928-12-03 | 1933-11-21 | Hough Arthur | Method of nitrating organic substances |
| US2957021A (en) * | 1959-01-20 | 1960-10-18 | Chattanooga Medicine Co | Nitrate esters of amino alcohols and salts thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| BR9103969A (pt) | 1992-03-03 |
| NZ236788A (en) | 1993-02-25 |
| WO1991010640A1 (en) | 1991-07-25 |
| EP0471043A4 (https=) | 1994-02-02 |
| US5089652A (en) | 1992-02-18 |
| CA2050288A1 (en) | 1991-07-18 |
| AU7169191A (en) | 1991-08-05 |
| EP0471043A1 (en) | 1992-02-19 |
| JPH04503961A (ja) | 1992-07-16 |
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