SU545251A3 - Способ получени м-ип фенилендиамина - Google Patents
Способ получени м-ип фенилендиаминаInfo
- Publication number
- SU545251A3 SU545251A3 SU2006474A SU2006474A SU545251A3 SU 545251 A3 SU545251 A3 SU 545251A3 SU 2006474 A SU2006474 A SU 2006474A SU 2006474 A SU2006474 A SU 2006474A SU 545251 A3 SU545251 A3 SU 545251A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- reaction
- water
- terephthalic
- reaction mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000005660 chlorination reaction Methods 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 4
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/54—Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions
- C07C209/58—Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions from or via amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/51—Phenylenediamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyamides (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2313496A DE2313496C3 (de) | 1973-03-19 | 1973-03-19 | Verfahren zur Herstellung von m- und p- Phenylendiamin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU545251A3 true SU545251A3 (ru) | 1977-01-30 |
Family
ID=5875163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2006474A SU545251A3 (ru) | 1973-03-19 | 1974-03-19 | Способ получени м-ип фенилендиамина |
Country Status (16)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2449983C1 (ru) * | 2010-12-23 | 2012-05-10 | Открытое акционерное общество "Каустик" (ОАО "Каустик") | СПОСОБ ПОЛУЧЕНИЯ п-ФЕНИЛЕНДИАМИНА |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2298532A1 (fr) | 1975-01-22 | 1976-08-20 | Akzo Nv | Bis-n-chloramides des acides carboxyliques aromatiques et cycloaliphatiques |
| DE2502411C2 (de) * | 1975-01-22 | 1977-02-24 | Akzo Gmbh | Verfahren zur herstellung von bis-n-chloramiden gesaettigter aliphatischer dicarbonsaeuren |
| DE3019491C2 (de) * | 1980-05-22 | 1985-02-21 | Akzo Gmbh, 5600 Wuppertal | Verfahren zur Herstellung von Oximcarbamaten |
| US5011997A (en) * | 1987-10-07 | 1991-04-30 | Hoechst Celanese Corp. | Process for bis(4-aminophenyl)hexafluoropropane |
| DE3909142A1 (de) * | 1989-03-21 | 1990-10-04 | Basf Ag | Verfahren zur herstellung von aminen |
| EP1636166A2 (en) * | 2003-06-23 | 2006-03-22 | Nippon Shokubai Co., Ltd. | Method for production of fluorinated phenylenediamine |
| KR101885110B1 (ko) * | 2016-11-10 | 2018-08-03 | 주식회사 오크켐텍 | 파라페닐렌디아민의 제조방법 |
| CN111100012B (zh) * | 2019-12-16 | 2021-01-22 | 上海交通大学 | 一种制备间苯二胺的方法 |
| CN113563199A (zh) * | 2020-04-29 | 2021-10-29 | 深圳有为技术控股集团有限公司 | 苯甲酰肼重排法制备间苯二胺和对苯二胺 |
| CN112174828B (zh) * | 2020-10-29 | 2022-01-07 | 山东兴强化工产业技术研究院有限公司 | 一种制备间苯二胺的方法 |
| CN113135826A (zh) * | 2021-04-14 | 2021-07-20 | 中芳特纤股份有限公司 | 一种对苯二胺的制备工艺 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3457311A (en) * | 1967-04-11 | 1969-07-22 | Armour Ind Chem Co | Process for preparing primary and secondary amines from amides |
| GB1238332A (US06368395-20020409-C00050.png) * | 1968-05-29 | 1971-07-07 | ||
| US3567746A (en) * | 1968-07-10 | 1971-03-02 | Pennwalt Corp | N-aryl benzamides |
-
1973
- 1973-03-19 DE DE2313496A patent/DE2313496C3/de not_active Expired
-
1974
- 1974-02-13 IT IT48283/74A patent/IT1046774B/it active
- 1974-02-14 AT AT118974A patent/AT327170B/de not_active IP Right Cessation
- 1974-02-15 CH CH213774A patent/CH591419A5/xx not_active IP Right Cessation
- 1974-02-18 FR FR7405429A patent/FR2222352B2/fr not_active Expired
- 1974-02-18 ES ES423367A patent/ES423367A2/es not_active Expired
- 1974-02-25 CA CA193,459A patent/CA1025884A/en not_active Expired
- 1974-02-27 DD DD176832A patent/DD110648A6/xx unknown
- 1974-03-04 NL NL7402872A patent/NL7402872A/xx not_active Application Discontinuation
- 1974-03-12 AU AU66561/74A patent/AU6656174A/en not_active Expired
- 1974-03-13 US US450675A patent/US3897498A/en not_active Expired - Lifetime
- 1974-03-15 BE BE142048A patent/BE812358R/xx active
- 1974-03-18 SE SE7403586A patent/SE386890B/xx unknown
- 1974-03-19 GB GB1206974A patent/GB1413946A/en not_active Expired
- 1974-03-19 SU SU2006474A patent/SU545251A3/ru active
- 1974-03-19 JP JP49031434A patent/JPS49134635A/ja active Pending
-
1983
- 1983-12-19 JP JP58238054A patent/JPS6029695B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2449983C1 (ru) * | 2010-12-23 | 2012-05-10 | Открытое акционерное общество "Каустик" (ОАО "Каустик") | СПОСОБ ПОЛУЧЕНИЯ п-ФЕНИЛЕНДИАМИНА |
Also Published As
| Publication number | Publication date |
|---|---|
| AU476714B2 (US06368395-20020409-C00050.png) | 1976-09-30 |
| JPS49134635A (US06368395-20020409-C00050.png) | 1974-12-25 |
| AU6656174A (en) | 1975-09-18 |
| JPS6029695B2 (ja) | 1985-07-12 |
| FR2222352A2 (US06368395-20020409-C00050.png) | 1974-10-18 |
| ATA118974A (de) | 1975-04-15 |
| DE2313496C3 (de) | 1979-07-19 |
| CA1025884A (en) | 1978-02-07 |
| SE386890B (sv) | 1976-08-23 |
| AT327170B (de) | 1976-01-26 |
| NL7402872A (US06368395-20020409-C00050.png) | 1974-09-23 |
| DE2313496A1 (de) | 1974-10-03 |
| GB1413946A (en) | 1975-11-12 |
| FR2222352B2 (US06368395-20020409-C00050.png) | 1977-09-16 |
| DE2313496B2 (US06368395-20020409-C00050.png) | 1978-11-16 |
| ES423367A2 (es) | 1977-07-01 |
| CH591419A5 (US06368395-20020409-C00050.png) | 1977-09-15 |
| DD110648A6 (US06368395-20020409-C00050.png) | 1975-01-12 |
| US3897498A (en) | 1975-07-29 |
| IT1046774B (it) | 1980-07-31 |
| JPS59130243A (ja) | 1984-07-26 |
| BE812358R (fr) | 1974-07-01 |
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