DE2217782A1 - Kontinuierliches verfahren zur herstellung von terephthalaldehyd - Google Patents
Kontinuierliches verfahren zur herstellung von terephthalaldehydInfo
- Publication number
- DE2217782A1 DE2217782A1 DE19722217782 DE2217782A DE2217782A1 DE 2217782 A1 DE2217782 A1 DE 2217782A1 DE 19722217782 DE19722217782 DE 19722217782 DE 2217782 A DE2217782 A DE 2217782A DE 2217782 A1 DE2217782 A1 DE 2217782A1
- Authority
- DE
- Germany
- Prior art keywords
- xylene
- tetrachloro
- terephthalaldehyde
- steam
- reactor
- 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.)
- Pending
Links
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 title claims description 26
- 238000010924 continuous production Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000003054 catalyst Substances 0.000 claims description 16
- 239000012808 vapor phase Substances 0.000 claims description 13
- 230000007062 hydrolysis Effects 0.000 claims description 11
- 238000006460 hydrolysis reaction Methods 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 claims description 6
- 229910000165 zinc phosphate Inorganic materials 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 5
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000003752 zinc compounds Chemical class 0.000 claims description 2
- 239000000356 contaminant Substances 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000011049 filling Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 238000009826 distribution Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- UMFGCTFGHULLPN-UHFFFAOYSA-N 4-(dichloromethyl)benzaldehyde Chemical compound ClC(Cl)C1=CC=C(C=O)C=C1 UMFGCTFGHULLPN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 159000000014 iron salts Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- CTSQZGJZQUVGBQ-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3,6-dimethylbenzene Chemical group CC1=C(Cl)C(Cl)=C(C)C(Cl)=C1Cl CTSQZGJZQUVGBQ-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000010416 ion conductor Substances 0.000 description 1
- 150000002506 iron compounds Chemical class 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- -1 sensitizers Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
- C07C45/43—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis of >CX2 groups, X being halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722217782 DE2217782A1 (de) | 1972-04-13 | 1972-04-13 | Kontinuierliches verfahren zur herstellung von terephthalaldehyd |
| DD16937773A DD106351A5 (cs) | 1972-04-13 | 1973-03-12 | |
| IT4907373A IT980025B (it) | 1972-04-13 | 1973-03-27 | Procedimento continuo per la produzione di aldeide tereftalica |
| CH493873A CH590190A5 (cs) | 1972-04-13 | 1973-04-06 | |
| SU7301907672A SU568358A3 (ru) | 1972-04-13 | 1973-04-10 | Способ получени терефталевого альдегида |
| JP4077373A JPS497240A (cs) | 1972-04-13 | 1973-04-10 | |
| FR7313286A FR2180045B1 (cs) | 1972-04-13 | 1973-04-12 | |
| GB1773973A GB1425348A (en) | 1972-04-13 | 1973-04-12 | Preparation of terephthalaldehyde |
| BE129975A BE798176A (fr) | 1972-04-13 | 1973-04-13 | Procede de preparation en continu de terephtalaldehyde |
| NL7305202A NL7305202A (cs) | 1972-04-13 | 1973-04-13 | |
| US05/777,800 US4125561A (en) | 1972-04-13 | 1977-03-15 | Process for production of terephthalic dialdehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722217782 DE2217782A1 (de) | 1972-04-13 | 1972-04-13 | Kontinuierliches verfahren zur herstellung von terephthalaldehyd |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2217782A1 true DE2217782A1 (de) | 1973-10-25 |
Family
ID=5841821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722217782 Pending DE2217782A1 (de) | 1972-04-13 | 1972-04-13 | Kontinuierliches verfahren zur herstellung von terephthalaldehyd |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS497240A (cs) |
| BE (1) | BE798176A (cs) |
| CH (1) | CH590190A5 (cs) |
| DD (1) | DD106351A5 (cs) |
| DE (1) | DE2217782A1 (cs) |
| FR (1) | FR2180045B1 (cs) |
| GB (1) | GB1425348A (cs) |
| IT (1) | IT980025B (cs) |
| NL (1) | NL7305202A (cs) |
| SU (1) | SU568358A3 (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2568439C1 (ru) * | 2015-01-12 | 2015-11-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Казанский национальный исследовательский технологический университет" (ФГБОУ ВПО "КНИТУ") | Способ получения терефталевого альдегида |
-
1972
- 1972-04-13 DE DE19722217782 patent/DE2217782A1/de active Pending
-
1973
- 1973-03-12 DD DD16937773A patent/DD106351A5/xx unknown
- 1973-03-27 IT IT4907373A patent/IT980025B/it active
- 1973-04-06 CH CH493873A patent/CH590190A5/xx not_active IP Right Cessation
- 1973-04-10 JP JP4077373A patent/JPS497240A/ja active Pending
- 1973-04-10 SU SU7301907672A patent/SU568358A3/ru active
- 1973-04-12 FR FR7313286A patent/FR2180045B1/fr not_active Expired
- 1973-04-12 GB GB1773973A patent/GB1425348A/en not_active Expired
- 1973-04-13 NL NL7305202A patent/NL7305202A/xx unknown
- 1973-04-13 BE BE129975A patent/BE798176A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7305202A (cs) | 1973-10-16 |
| BE798176A (fr) | 1973-07-31 |
| JPS497240A (cs) | 1974-01-22 |
| CH590190A5 (cs) | 1977-07-29 |
| GB1425348A (en) | 1976-02-18 |
| DD106351A5 (cs) | 1974-06-12 |
| FR2180045A1 (cs) | 1973-11-23 |
| SU568358A3 (ru) | 1977-08-05 |
| IT980025B (it) | 1974-09-30 |
| FR2180045B1 (cs) | 1977-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |