JP2004238393A - グリセリン、硝酸および苛性アルカリからグリシジルニトレートを製造するための連続法および装置系、並びにグリシジルニトレートのポリ・グリシジルニトレートへの転化 - Google Patents
グリセリン、硝酸および苛性アルカリからグリシジルニトレートを製造するための連続法および装置系、並びにグリシジルニトレートのポリ・グリシジルニトレートへの転化 Download PDFInfo
- Publication number
- JP2004238393A JP2004238393A JP2004005608A JP2004005608A JP2004238393A JP 2004238393 A JP2004238393 A JP 2004238393A JP 2004005608 A JP2004005608 A JP 2004005608A JP 2004005608 A JP2004005608 A JP 2004005608A JP 2004238393 A JP2004238393 A JP 2004238393A
- Authority
- JP
- Japan
- Prior art keywords
- product
- reaction vessel
- dinitroglycerin
- nitrate
- nitric acid
- 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.)
- Pending
Links
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 152
- ADZAAKGRMMGJKM-UHFFFAOYSA-N oxiran-2-ylmethyl nitrate Chemical compound [O-][N+](=O)OCC1CO1 ADZAAKGRMMGJKM-UHFFFAOYSA-N 0.000 title claims abstract description 115
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims abstract description 75
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 229910017604 nitric acid Inorganic materials 0.000 title claims abstract description 59
- 239000003518 caustics Substances 0.000 title claims abstract description 38
- 235000011187 glycerol Nutrition 0.000 title claims abstract description 37
- 238000010924 continuous production Methods 0.000 title abstract description 13
- -1 poly(glycidyl nitrate) Polymers 0.000 title 2
- 238000000926 separation method Methods 0.000 claims abstract description 50
- VSOJWGJCPFPODA-UHFFFAOYSA-N 1,3-dinitropropane-1,2,3-triol Chemical compound [O-][N+](=O)C(O)C(O)C(O)[N+]([O-])=O VSOJWGJCPFPODA-UHFFFAOYSA-N 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims description 165
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 110
- 239000000047 product Substances 0.000 claims description 104
- 230000008569 process Effects 0.000 claims description 70
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 64
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 56
- 239000002904 solvent Substances 0.000 claims description 40
- 239000004317 sodium nitrate Substances 0.000 claims description 28
- 235000010344 sodium nitrate Nutrition 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 229910001868 water Inorganic materials 0.000 claims description 25
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 20
- 239000012267 brine Substances 0.000 claims description 18
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 18
- 239000002699 waste material Substances 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 15
- ASIGVDLTBLZXNC-UHFFFAOYSA-N 1,3-dinitroglycerol Chemical compound [O-][N+](=O)OCC(O)CO[N+]([O-])=O ASIGVDLTBLZXNC-UHFFFAOYSA-N 0.000 claims description 14
- 239000011780 sodium chloride Substances 0.000 claims description 10
- 230000007246 mechanism Effects 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 229910002651 NO3 Inorganic materials 0.000 claims description 7
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 7
- 239000006227 byproduct Substances 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 3
- 230000003068 static effect Effects 0.000 claims description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000007599 discharging Methods 0.000 claims 2
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 49
- 239000000463 material Substances 0.000 abstract description 2
- 238000010963 scalable process Methods 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 25
- 238000006396 nitration reaction Methods 0.000 description 11
- 150000002823 nitrates Chemical class 0.000 description 9
- 238000000746 purification Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 6
- 239000002360 explosive Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 238000012545 processing Methods 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003380 propellant Substances 0.000 description 4
- 238000004065 wastewater treatment Methods 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000010865 sewage Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000012993 chemical processing Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000000006 Nitroglycerin Substances 0.000 description 1
- KIMIUKVFFFDXBW-UHFFFAOYSA-N O=NOCC1CO1 Chemical compound O=NOCC1CO1 KIMIUKVFFFDXBW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009993 causticizing Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 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
- 238000004090 dissolution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 229960003711 glyceryl trinitrate Drugs 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 239000002920 hazardous waste Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000013461 intermediate chemical Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000010815 organic waste Substances 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007100 recyclization reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/340,167 US6870061B2 (en) | 2003-01-10 | 2003-01-10 | Continuous process and system for production of glycidyl nitrate from glycerin, nitric acid and caustic and conversion of glycidyl nitrate to poly(glycidyl nitrate) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004238393A true JP2004238393A (ja) | 2004-08-26 |
| JP2004238393A5 JP2004238393A5 (https=) | 2006-03-30 |
Family
ID=31188249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004005608A Pending JP2004238393A (ja) | 2003-01-10 | 2004-01-13 | グリセリン、硝酸および苛性アルカリからグリシジルニトレートを製造するための連続法および装置系、並びにグリシジルニトレートのポリ・グリシジルニトレートへの転化 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US6870061B2 (https=) |
| JP (1) | JP2004238393A (https=) |
| FR (1) | FR2851770B1 (https=) |
| GB (1) | GB2398567B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011500735A (ja) * | 2007-10-25 | 2011-01-06 | 北京天▲チン▼化工有限責任公司 | ３−イソチアゾリノン誘導体およびその中間体生成物を連続的に生産する方法 |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10350672B4 (de) * | 2003-10-30 | 2009-10-29 | Südzucker Aktiengesellschaft | Verfahren zur Reduzierung des Kalkverbrauches bei der Zuckerrübensaft-Reinigung |
| US20070135380A1 (en) * | 2005-08-12 | 2007-06-14 | Radiorx, Inc. | O-nitro compounds, pharmaceutical compositions thereof and uses thereof |
| US8471041B2 (en) * | 2010-02-09 | 2013-06-25 | Alliant Techsystems Inc. | Methods of synthesizing and isolating N-(bromoacetyl)-3,3-dinitroazetidine and a composition including the same |
| WO2014047319A1 (en) * | 2012-09-20 | 2014-03-27 | M-I L.L.C. | Oil based flocculation mixing and dispersion system |
| CN109069420A (zh) | 2016-01-11 | 2018-12-21 | 埃皮辛特瑞柯斯公司 | 2-溴-1-(3，3-二硝基氮杂环丁烷-1-基)乙酮静脉施用的组合物和方法 |
| WO2019164593A2 (en) | 2018-01-08 | 2019-08-29 | Epicentrx, Inc. | Methods and compositions utilizing rrx-001 combination therapy for radioprotection |
| US10562873B1 (en) | 2018-12-07 | 2020-02-18 | Northrop Grumman Innovation Systems, Inc. | Methods of producing glycidyl nitrate |
| US20230183198A1 (en) * | 2021-12-10 | 2023-06-15 | Northrop Grumman Systems Corporation | Methods of producing glycidyl nitrate and related systems |
| CN119746792B (zh) * | 2024-12-17 | 2025-10-03 | 中国石油大学(华东) | 一种基于氯闭环循环利用的环氧烷烃氯醇法清洁生产装置 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990001028A1 (en) * | 1988-07-22 | 1990-02-08 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Preparation of nitratoalkyl-substituted cyclic ethers |
| GB8817545D0 (en) * | 1988-07-22 | 1988-08-24 | Secr Defence | Preparation of epoxy nitrates |
| US5120827A (en) * | 1990-08-02 | 1992-06-09 | Thiokol Corporation | Process for producing improved poly(glycidyl nitrate) |
| WO2001029111A1 (en) * | 1999-10-19 | 2001-04-26 | Alliant Techsystems Inc. | Polymerization of poly(glycidyl nitrate) from high purity glycidyl nitrate synthesized from glycerol |
-
2003
- 2003-01-10 US US10/340,167 patent/US6870061B2/en not_active Expired - Lifetime
- 2003-12-24 GB GB0330032A patent/GB2398567B/en not_active Expired - Fee Related
-
2004
- 2004-01-08 FR FR0400105A patent/FR2851770B1/fr not_active Expired - Fee Related
- 2004-01-13 JP JP2004005608A patent/JP2004238393A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011500735A (ja) * | 2007-10-25 | 2011-01-06 | 北京天▲チン▼化工有限責任公司 | ３−イソチアゾリノン誘導体およびその中間体生成物を連続的に生産する方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2851770A1 (fr) | 2004-09-03 |
| FR2851770B1 (fr) | 2007-08-03 |
| GB2398567B (en) | 2007-08-01 |
| US6870061B2 (en) | 2005-03-22 |
| GB0330032D0 (en) | 2004-01-28 |
| US20040138481A1 (en) | 2004-07-15 |
| GB2398567A (en) | 2004-08-25 |
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