JPH0430939B2 - - Google Patents
Info
- Publication number
- JPH0430939B2 JPH0430939B2 JP17504684A JP17504684A JPH0430939B2 JP H0430939 B2 JPH0430939 B2 JP H0430939B2 JP 17504684 A JP17504684 A JP 17504684A JP 17504684 A JP17504684 A JP 17504684A JP H0430939 B2 JPH0430939 B2 JP H0430939B2
- Authority
- JP
- Japan
- Prior art keywords
- dichlorobenzene
- crystals
- reaction
- methanol
- phosgenation
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- 239000013078 crystal Substances 0.000 claims description 37
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 18
- 229940117389 dichlorobenzene Drugs 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 9
- 238000002425 crystallisation Methods 0.000 claims description 8
- 230000008025 crystallization Effects 0.000 claims description 8
- 239000002612 dispersion medium Substances 0.000 claims description 4
- -1 ethylhexanoate trihydrochloride Chemical compound 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 description 19
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000007789 gas Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 238000010298 pulverizing process Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- JBBURJFZIMRPCZ-XRIGFGBMSA-N (2s)-2,6-diaminohexanoic acid;hydron;dichloride Chemical compound Cl.Cl.NCCCC[C@H](N)C(O)=O JBBURJFZIMRPCZ-XRIGFGBMSA-N 0.000 description 2
- PMUNIMVZCACZBB-UHFFFAOYSA-N 2-hydroxyethylazanium;chloride Chemical compound Cl.NCCO PMUNIMVZCACZBB-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229940073579 ethanolamine hydrochloride Drugs 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000011164 primary particle Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- BOWUOGIPSRVRSJ-UHFFFAOYSA-N 2-aminohexano-6-lactam Chemical compound NC1CCCCNC1=O BOWUOGIPSRVRSJ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940031098 ethanolamine Drugs 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP17504684A JPS6153249A (ja) | 1984-08-24 | 1984-08-24 | 2,6,2′―トリアミノエチルヘキサノエート・三塩酸塩のホスゲン化方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP17504684A JPS6153249A (ja) | 1984-08-24 | 1984-08-24 | 2,6,2′―トリアミノエチルヘキサノエート・三塩酸塩のホスゲン化方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6153249A JPS6153249A (ja) | 1986-03-17 |
JPH0430939B2 true JPH0430939B2 (el) | 1992-05-25 |
Family
ID=15989277
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP17504684A Granted JPS6153249A (ja) | 1984-08-24 | 1984-08-24 | 2,6,2′―トリアミノエチルヘキサノエート・三塩酸塩のホスゲン化方法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6153249A (el) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3626705B1 (en) | 2017-05-15 | 2021-03-24 | Asahi Kasei Kabushiki Kaisha | Isocyanate production method |
-
1984
- 1984-08-24 JP JP17504684A patent/JPS6153249A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS6153249A (ja) | 1986-03-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US6022985A (en) | Process for the preparation of 4-acetoxy-2α-benzoyloxy-5β, 20-epoxy-1, 7β-10β-trihydroxy-9-oxo-tax-11-en-13α-yl(2R,3S)-3-tert-b utoxy-carbonYlamino-2-hydroxy-3-phenylpropionate trihydrate | |
JPS62171905A (ja) | 遊離ヒドロキシルアミン水溶液の製造方法 | |
JPS6245576A (ja) | 安定化トラセミドを含有する利尿剤 | |
EP1377544B2 (en) | Purification of 2-nitro-4-methylsulphonylbenzoic acid | |
JPH03128392A (ja) | 3α,7β―ジヒドロキシ―12―ケト―5β―コラン酸の精製方法 | |
CN1297885A (zh) | 1,1-环己基二乙酸单酰胺的制备方法 | |
US4016210A (en) | Crystallization process | |
JPH0430939B2 (el) | ||
JP3521242B2 (ja) | ビスクレゾール類の精製方法 | |
JPS5926612B2 (ja) | D d’−2 2’− ( エチレンジイミノ ) ジ −1− ブタノ−ルニエンサンエンノ セイホウ | |
US2978514A (en) | Separation of pentaerythritol and dipentaerythritol from solution | |
US4154759A (en) | Preparation of N-(phosphonoacetyl)-L-aspartic acid | |
US3784562A (en) | Methyl acetoacetic ester enamine of d-2-(1,4-cyclohexadien-1-yl)glycine, sodium salt-dimethylformamide adduct | |
JPH0466863B2 (el) | ||
JP3208971B2 (ja) | O,o’−ジアシル酒石酸の製造方法 | |
EP0035759B1 (en) | Process for producing dithionites | |
JPS60258151A (ja) | 付加的官能基を含有するn‐ベンジルオキシカルボニルアミノ酸の製造法 | |
JPS6153254A (ja) | 2,6,2′−トリイソシアネ−トエチルヘキサノエ−トの製造方法 | |
JPH0446253B2 (el) | ||
JP3862981B2 (ja) | 2−エチル−2−アダマンチルメタクリレート結晶粉末 | |
WO1999041272A1 (fr) | Procede de purification du sterol de tall oil | |
JPH02306961A (ja) | ターフェナジンの高融点多形型の製造 | |
EP0018813B1 (en) | Crystalline germaazaspirodiones,their preparation and their use in the preparation of germaazaspiranes | |
CN116375594A (zh) | 一种依喜替康中间体制备工艺 | |
JPS6252754B2 (el) |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
EXPY | Cancellation because of completion of term |