JPS6151575B2 - - Google Patents
Info
- Publication number
- JPS6151575B2 JPS6151575B2 JP55016136A JP1613680A JPS6151575B2 JP S6151575 B2 JPS6151575 B2 JP S6151575B2 JP 55016136 A JP55016136 A JP 55016136A JP 1613680 A JP1613680 A JP 1613680A JP S6151575 B2 JPS6151575 B2 JP S6151575B2
- Authority
- JP
- Japan
- Prior art keywords
- alkali
- bromonitroalcohol
- nitromethane
- solvent
- solution
- 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
Links
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 12
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 12
- 239000003513 alkali Substances 0.000 claims description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- -1 alkane polyol Chemical class 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 6
- 229920005862 polyol Polymers 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000008044 alkali metal hydroxides Chemical group 0.000 claims description 3
- 235000011187 glycerol Nutrition 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000007259 addition reaction Methods 0.000 description 8
- 238000005893 bromination reaction Methods 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000031709 bromination Effects 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 description 5
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001447 alkali salts Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 229910001617 alkaline earth metal chloride Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 125000004971 nitroalkyl group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- YTIXGBHAPNMOKU-UHFFFAOYSA-N 2-nitropropane-1,3-diol Chemical compound OCC(CO)[N+]([O-])=O YTIXGBHAPNMOKU-UHFFFAOYSA-N 0.000 description 1
- XIAMXNMLRAUKOQ-UHFFFAOYSA-N 3-bromo-3-nitropentane-2,4-diol Chemical compound CC(O)C(Br)(C(C)O)[N+]([O-])=O XIAMXNMLRAUKOQ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1613680A JPS56113745A (en) | 1980-02-13 | 1980-02-13 | Preparation of bromonitroalcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1613680A JPS56113745A (en) | 1980-02-13 | 1980-02-13 | Preparation of bromonitroalcohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56113745A JPS56113745A (en) | 1981-09-07 |
| JPS6151575B2 true JPS6151575B2 (fr) | 1986-11-10 |
Family
ID=11908072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1613680A Granted JPS56113745A (en) | 1980-02-13 | 1980-02-13 | Preparation of bromonitroalcohol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56113745A (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3814773A1 (de) * | 1988-04-30 | 1989-11-09 | Henkel Kgaa | Verfahren zur bromierung von nitroalkoholen |
| KR20020008330A (ko) * | 2000-07-21 | 2002-01-30 | 이재규 | 2-브로모-2-나이트로-1,3-프로판디올의 제조방법 |
-
1980
- 1980-02-13 JP JP1613680A patent/JPS56113745A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56113745A (en) | 1981-09-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2056402C1 (ru) | Способ получения гидрата трифторацетальдегида | |
| JPH0273049A (ja) | ３―ジアルキルアミノプロピオニトリル、ビス―（２―シアノエチル）―エーテル及び所望によりエチレンシアンヒドリンの共通製法 | |
| JPS6151575B2 (fr) | ||
| JPS6155902B2 (fr) | ||
| JP2006298855A (ja) | ３，３，３−トリフルオロプロピオン酸の製造方法 | |
| JPH0223535B2 (fr) | ||
| US4231962A (en) | 3-Phenoxybenzylideneamines and 3-benzylbenzylideneamines | |
| JPH0115497B2 (fr) | ||
| JP2006298854A (ja) | ３，３，３−トリフルオロプロピオン酸の製造方法 | |
| JPS5874623A (ja) | （Ｒ，Ｒ，Ｒ）―α―トコフェロールの側鎖合成のための光学活性中間体の製法 | |
| US3892814A (en) | Cyclopropane derivatives | |
| JP2000256244A (ja) | ４−メチルテトラフルオロベンジルアルコール誘導体の製造法 | |
| US6111130A (en) | Process for the preparation of trifluoromethyl containing derivatives | |
| JPS5944315B2 (ja) | ２−ペンチニルエ−テルの製造法 | |
| JPH0142951B2 (fr) | ||
| JPH0159266B2 (fr) | ||
| JPH0586000A (ja) | ２−アミノ−４−フルオロ安息香酸の製造方法 | |
| JP2791572B2 (ja) | 大環状化合物及びその製造法 | |
| JPH05155815A (ja) | グリセロール誘導体の製造方法 | |
| JP3191114B2 (ja) | ４−アルキリデン−３，５，５−トリメチル−２−シクロヘキセン−１−オンの製法 | |
| JPH027583B2 (fr) | ||
| JP2741744B2 (ja) | 有機化合物のアルキル化方法 | |
| US20040192958A1 (en) | Process for preparing derivatives of 4-halobutyraldehyde | |
| JPS6227054B2 (fr) | ||
| JPS6350340B2 (fr) |