DE1160427B - Verfahren zur Herstellung von Salpetersaeureestern mehrwertiger Alkohole - Google Patents
Verfahren zur Herstellung von Salpetersaeureestern mehrwertiger AlkoholeInfo
- Publication number
- DE1160427B DE1160427B DEN21677A DEN0021677A DE1160427B DE 1160427 B DE1160427 B DE 1160427B DE N21677 A DEN21677 A DE N21677A DE N0021677 A DEN0021677 A DE N0021677A DE 1160427 B DE1160427 B DE 1160427B
- Authority
- DE
- Germany
- Prior art keywords
- nitric acid
- polyhydric alcohols
- phase
- acid esters
- pentaerythritol
- 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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 13
- 150000005846 sugar alcohols Polymers 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- 229910017604 nitric acid Inorganic materials 0.000 claims description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 6
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- ZODDGFAZWTZOSI-UHFFFAOYSA-N nitric acid;sulfuric acid Chemical compound O[N+]([O-])=O.OS(O)(=O)=O ZODDGFAZWTZOSI-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000006396 nitration reaction Methods 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- BRBAEHHXGZRCBK-UHFFFAOYSA-N pentrinitrol Chemical compound [O-][N+](=O)OCC(CO)(CO[N+]([O-])=O)CO[N+]([O-])=O BRBAEHHXGZRCBK-UHFFFAOYSA-N 0.000 description 4
- 229950006286 pentrinitrol Drugs 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OORDEDRRTSWSRC-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] acetate Chemical compound CC(=O)OCC(CO)(CO)CO OORDEDRRTSWSRC-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- -1 pentaerythritol 1,1,3-trimethylol acetone 1,1,3-trimethylol acetone trinitrate Chemical compound 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- FZJWITMDCJLVSZ-UHFFFAOYSA-N [2-(hydroxymethyl)-3-nitrooxy-2-(nitrooxymethyl)propyl] acetate Chemical compound [N+](=O)([O-])OCC(COC(C)=O)(CO[N+](=O)[O-])CO FZJWITMDCJLVSZ-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YXCDZXGJZDGMEP-UHFFFAOYSA-N 4-hydroxy-3,3-bis(hydroxymethyl)butan-2-one Chemical compound CC(=O)C(CO)(CO)CO YXCDZXGJZDGMEP-UHFFFAOYSA-N 0.000 description 1
- KHAIISDEIXPDCH-UHFFFAOYSA-N 4-hydroxy-3,3-bis(hydroxymethyl)butan-2-one nitric acid Chemical compound [N+](=O)(O)[O-].[N+](=O)(O)[O-].C(O)C(C(=O)C)(CO)CO KHAIISDEIXPDCH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical class ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- OUHCZCFQVONTOC-UHFFFAOYSA-N [3-acetyloxy-2,2-bis(acetyloxymethyl)propyl] acetate Chemical compound CC(=O)OCC(COC(C)=O)(COC(C)=O)COC(C)=O OUHCZCFQVONTOC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- IODDQGMEFSNLGV-UHFFFAOYSA-N butane;hydrochloride Chemical class Cl.CCCC IODDQGMEFSNLGV-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- KGMXPXPXPAAUMD-UHFFFAOYSA-N propane;dihydrochloride Chemical class Cl.Cl.CCC KGMXPXPXPAAUMD-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C203/00—Esters of nitric or nitrous acid
- C07C203/02—Esters of nitric acid
- C07C203/04—Esters of nitric acid having nitrate groups bound to acyclic carbon atoms
-
- 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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE632627D BE632627A (en, 2012) | 1962-06-07 | ||
| DEN21677A DE1160427B (de) | 1962-06-07 | 1962-06-07 | Verfahren zur Herstellung von Salpetersaeureestern mehrwertiger Alkohole |
| CH572963A CH420093A (de) | 1962-06-07 | 1963-05-07 | Verfahren zur Herstellung von Salpetersäureestern mehrwertiger Alkohole |
| FR935457A FR1357403A (fr) | 1962-06-07 | 1963-05-21 | Procédé pour la nitration partielle d'alcools polyvalents |
| GB2152563A GB1040139A (en) | 1962-06-07 | 1963-05-29 | A method of partially nitrating polyhydric alcohols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEN21677A DE1160427B (de) | 1962-06-07 | 1962-06-07 | Verfahren zur Herstellung von Salpetersaeureestern mehrwertiger Alkohole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1160427B true DE1160427B (de) | 1964-01-02 |
Family
ID=7341824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEN21677A Pending DE1160427B (de) | 1962-06-07 | 1962-06-07 | Verfahren zur Herstellung von Salpetersaeureestern mehrwertiger Alkohole |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE632627A (en, 2012) |
| CH (1) | CH420093A (en, 2012) |
| DE (1) | DE1160427B (en, 2012) |
| GB (1) | GB1040139A (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2039609A1 (de) * | 1970-06-30 | 1972-02-17 | Council Scient Ind Res | Verfahren zur Herstellung von Alkylnitratestern aus Glykolaethern |
| EP0066999A1 (en) * | 1981-06-01 | 1982-12-15 | Hercules Incorporated | Process for co-nitrating trimethylolethane and diethylene glycol |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5503199A (en) * | 1998-06-24 | 2000-01-10 | Alpharma-Isis Gmbh And Co. Kg | Analytic substrates and antioxidative agents |
| EP1136468A3 (en) * | 2000-03-23 | 2001-11-14 | Cordant Technologies, Inc. | Method of synthesizing diglycerol tetranitrate, and solid rocket motor propellant containing the same |
| ITMI20022410A1 (it) * | 2002-11-14 | 2004-05-15 | Dinamite Dipharma S P A | Procedimento per la nitrazione di alcandioli. |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2465984A (en) * | 1946-05-21 | 1949-03-29 | Union Oil Co | Production of cycloalkyl nitrites |
| US2545538A (en) * | 1947-12-11 | 1951-03-20 | Du Pont | Process for manufacture of nitric esters of normally solid primary alcohols |
| DE1016701B (de) | 1956-02-24 | 1957-10-03 | Basf Ag | Verfahren zur Herstellung cycloaliphatischer Nitrate |
-
0
- BE BE632627D patent/BE632627A/xx unknown
-
1962
- 1962-06-07 DE DEN21677A patent/DE1160427B/de active Pending
-
1963
- 1963-05-07 CH CH572963A patent/CH420093A/de unknown
- 1963-05-29 GB GB2152563A patent/GB1040139A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2465984A (en) * | 1946-05-21 | 1949-03-29 | Union Oil Co | Production of cycloalkyl nitrites |
| US2545538A (en) * | 1947-12-11 | 1951-03-20 | Du Pont | Process for manufacture of nitric esters of normally solid primary alcohols |
| DE1016701B (de) | 1956-02-24 | 1957-10-03 | Basf Ag | Verfahren zur Herstellung cycloaliphatischer Nitrate |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2039609A1 (de) * | 1970-06-30 | 1972-02-17 | Council Scient Ind Res | Verfahren zur Herstellung von Alkylnitratestern aus Glykolaethern |
| EP0066999A1 (en) * | 1981-06-01 | 1982-12-15 | Hercules Incorporated | Process for co-nitrating trimethylolethane and diethylene glycol |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1040139A (en) | 1966-08-24 |
| BE632627A (en, 2012) | |
| CH420093A (de) | 1966-09-15 |
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