IL106166A - תהליך לייצור ולהפקת האלוניטרואלקאנים - Google Patents
תהליך לייצור ולהפקת האלוניטרואלקאניםInfo
- Publication number
- IL106166A IL106166A IL106166A IL10616693A IL106166A IL 106166 A IL106166 A IL 106166A IL 106166 A IL106166 A IL 106166A IL 10616693 A IL10616693 A IL 10616693A IL 106166 A IL106166 A IL 106166A
- Authority
- IL
- Israel
- Prior art keywords
- halonitroalkane
- reaction mixture
- nitroalkane
- salt
- recovery
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 38
- 230000008569 process Effects 0.000 title claims description 28
- 238000011084 recovery Methods 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 26
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 18
- DNPRVXJGNANVCZ-UHFFFAOYSA-N bromo(nitro)methane Chemical group [O-][N+](=O)CBr DNPRVXJGNANVCZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000002585 base Substances 0.000 claims description 15
- 238000004821 distillation Methods 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 10
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 238000010533 azeotropic distillation Methods 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 7
- LYGJENNIWJXYER-BJUDXGSMSA-N nitromethane Chemical class [11CH3][N+]([O-])=O LYGJENNIWJXYER-BJUDXGSMSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
- 229910052794 bromium Inorganic materials 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000020477 pH reduction Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- FMXOEQQPVONPBU-UHFFFAOYSA-N methylidene(dioxido)azanium Chemical class [O-][N+]([O-])=C FMXOEQQPVONPBU-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000001256 steam distillation Methods 0.000 description 5
- 238000003556 assay Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000005893 bromination reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000003068 static effect Effects 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000010979 pH adjustment Methods 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical group CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- LKCWTYWDYSYPCJ-UHFFFAOYSA-N [Br-](Br)Br.[Na+] Chemical compound [Br-](Br)Br.[Na+] LKCWTYWDYSYPCJ-UHFFFAOYSA-N 0.000 description 1
- GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical class Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001509 metal bromide Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- -1 sodium bisulfite Chemical class 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- RZJLHJFNHJKOAZ-UHFFFAOYSA-N sodium;methylidene(dioxido)azanium Chemical compound [Na+].[O-][N+]([O-])=C RZJLHJFNHJKOAZ-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010626 work up procedure Methods 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
- C07C201/06—Preparation of nitro compounds
- C07C201/16—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/01—Compounds containing nitro groups bound to a carbon skeleton having nitro 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
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/910,005 US5180859A (en) | 1992-07-07 | 1992-07-07 | Process for the production and recovery of halonitroalkanes in high yield |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL106166A0 IL106166A0 (en) | 1993-10-20 |
| IL106166A true IL106166A (he) | 1998-02-08 |
Family
ID=25428175
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL106166A IL106166A (he) | 1992-07-07 | 1993-06-29 | תהליך לייצור ולהפקת האלוניטרואלקאנים |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5180859A (he) |
| EP (1) | EP0649401B1 (he) |
| JP (1) | JPH07508754A (he) |
| KR (1) | KR950702521A (he) |
| AU (1) | AU675075B2 (he) |
| CA (1) | CA2139753A1 (he) |
| DE (1) | DE69314637T2 (he) |
| IL (1) | IL106166A (he) |
| MX (1) | MX9304062A (he) |
| WO (1) | WO1994001391A1 (he) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5866511A (en) * | 1997-05-15 | 1999-02-02 | Great Lakes Chemical Corporation | Stabilized solutions of bromonitromethane and their use as biocides |
| EP1917231B1 (en) | 2005-08-26 | 2013-10-02 | Bromine Compounds Ltd. | Process of preparing bromopicrin |
| IL183445A (en) | 2007-05-27 | 2013-02-28 | Bromine Compounds Ltd | Continuous process of preparing bromopicrin |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2632776A (en) * | 1950-11-02 | 1953-03-24 | Dow Chemical Co | Production of monobromonitromethane |
| GB1011115A (en) * | 1961-07-31 | 1965-11-24 | Aerojet General Co | Process for the production of gem-dinitro alcohols and gem-dinitro alkanes and products obtained by the process |
| US5043489A (en) * | 1988-12-02 | 1991-08-27 | Angus Chemical Company | Method of preparing monohalogenated nitroalkanes |
| US4922030A (en) * | 1988-12-05 | 1990-05-01 | Angus Chemical Company | Method of preparing halogenated nitroalcohols |
| US5243092A (en) * | 1991-09-11 | 1993-09-07 | K·I Chemical Industry Co., Ltd. | Method for producing 2,2-dibromo-2-nitroethanol |
-
1992
- 1992-07-07 US US07/910,005 patent/US5180859A/en not_active Expired - Fee Related
-
1993
- 1993-06-29 IL IL106166A patent/IL106166A/he not_active IP Right Cessation
- 1993-07-02 AU AU46628/93A patent/AU675075B2/en not_active Ceased
- 1993-07-02 EP EP93916939A patent/EP0649401B1/en not_active Expired - Lifetime
- 1993-07-02 JP JP6503439A patent/JPH07508754A/ja active Pending
- 1993-07-02 KR KR1019950700027A patent/KR950702521A/ko not_active Abandoned
- 1993-07-02 DE DE69314637T patent/DE69314637T2/de not_active Expired - Fee Related
- 1993-07-02 CA CA002139753A patent/CA2139753A1/en not_active Abandoned
- 1993-07-02 WO PCT/US1993/006306 patent/WO1994001391A1/en not_active Ceased
- 1993-07-06 MX MX9304062A patent/MX9304062A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL106166A0 (en) | 1993-10-20 |
| DE69314637D1 (de) | 1997-11-20 |
| KR950702521A (ko) | 1995-07-29 |
| AU675075B2 (en) | 1997-01-23 |
| EP0649401B1 (en) | 1997-10-15 |
| US5180859A (en) | 1993-01-19 |
| JPH07508754A (ja) | 1995-09-28 |
| WO1994001391A1 (en) | 1994-01-20 |
| DE69314637T2 (de) | 1998-04-30 |
| AU4662893A (en) | 1994-01-31 |
| EP0649401A4 (en) | 1995-03-01 |
| MX9304062A (es) | 1994-04-29 |
| CA2139753A1 (en) | 1994-01-20 |
| EP0649401A1 (en) | 1995-04-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| RH1 | Patent not in force |