JPH0582380B2 - - Google Patents
Info
- Publication number
- JPH0582380B2 JPH0582380B2 JP6633984A JP6633984A JPH0582380B2 JP H0582380 B2 JPH0582380 B2 JP H0582380B2 JP 6633984 A JP6633984 A JP 6633984A JP 6633984 A JP6633984 A JP 6633984A JP H0582380 B2 JPH0582380 B2 JP H0582380B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- methanol
- sodium
- liquid
- crystals
- 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 - Lifetime
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 5
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical group 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 239000007788 liquid Substances 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 7
- 238000007033 dehydrochlorination reaction Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 150000007514 bases Chemical class 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- -1 monochloroacetic acid ester Chemical class 0.000 description 2
- 238000012805 post-processing Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229920006015 heat resistant resin Polymers 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6633984A JPS60209552A (ja) | 1984-04-03 | 1984-04-03 | ４，４’−ビス（カルボアルコキシメチレンアミノ）ジフエニルメタンの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6633984A JPS60209552A (ja) | 1984-04-03 | 1984-04-03 | ４，４’−ビス（カルボアルコキシメチレンアミノ）ジフエニルメタンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60209552A JPS60209552A (ja) | 1985-10-22 |
| JPH0582380B2 true JPH0582380B2 (nl) | 1993-11-18 |
Family
ID=13312995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6633984A Granted JPS60209552A (ja) | 1984-04-03 | 1984-04-03 | ４，４’−ビス（カルボアルコキシメチレンアミノ）ジフエニルメタンの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60209552A (nl) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH093442A (ja) * | 1995-06-20 | 1997-01-07 | Matsushita Electric Ind Co Ltd | 表面処理剤とその使用方法 |
-
1984
- 1984-04-03 JP JP6633984A patent/JPS60209552A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60209552A (ja) | 1985-10-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6351358A (ja) | ジタ−シヤリ−ブチルジカ−ボネ−トの製法 | |
| FR2470758A1 (fr) | Procede pour la fixation de groupes alkyles sur une chaine carbonee portant un groupe fonctionnel | |
| JPS59175484A (ja) | Ｎ−ホルミルアスパラギン酸無水物の製造法 | |
| JPH0582380B2 (nl) | ||
| JPS6210510B2 (nl) | ||
| JPH029576B2 (nl) | ||
| EP1146040A2 (en) | Method of crystallizing 2-azabicyclo(2.2.1)hept-5-en-3-one | |
| JPH07278156A (ja) | ジメチルアミン−ボランの製造方法 | |
| JP3486922B2 (ja) | 酸アミドの製造法 | |
| JPH03190856A (ja) | 精製ヒドロペルオキシドの製造方法 | |
| JPS6351146B2 (nl) | ||
| JPS6320438B2 (nl) | ||
| JP4370460B2 (ja) | アミド化合物の製造方法 | |
| JPH0948789A (ja) | Ｏ，ｓ−ジメチル−ｎ−アセチルホスホルアミドチオエートの精製法 | |
| JPH027305B2 (nl) | ||
| JP4076649B2 (ja) | ２−アザビシクロ［２．２．１］ヘプト−５−エン−３−オンの製造方法 | |
| JP2590436B2 (ja) | ジフェニルジスルホニルフルオライドの合成方法 | |
| JP2006199599A (ja) | ビス含フッ素フタロニトリル化合物の製造方法 | |
| JP2000001474A (ja) | Ｎ―ベンジル―３―ヒドロキシアゼチジンの製造法 | |
| JPH05125023A (ja) | ２−ビスアリールアミノ−９，９−ジアルキルフルオレンの単離方法 | |
| JPH075493B2 (ja) | ビス（２―ヒドロキシヘキサフルオロ―２―プロピル）ベンゼン誘導体の製造方法 | |
| JPS58121251A (ja) | ５−〔２−（ジアルキルアミノ）エトキシ〕カルバクロ−ルアセテ−ト塩酸塩の製法 | |
| JPS6356218B2 (nl) | ||
| JPH03112966A (ja) | ３―アルキル―２，６―ジアミノピリジンの製造法 | |
| JPH04346961A (ja) | Ｐ−アセトキシ安息香酸の製造方法 |