DE2934614C2 - Verfahren zur Herstellung von Terephthalaldehyd bzw. Isophthalaldehyd - Google Patents
Verfahren zur Herstellung von Terephthalaldehyd bzw. IsophthalaldehydInfo
- Publication number
- DE2934614C2 DE2934614C2 DE2934614A DE2934614A DE2934614C2 DE 2934614 C2 DE2934614 C2 DE 2934614C2 DE 2934614 A DE2934614 A DE 2934614A DE 2934614 A DE2934614 A DE 2934614A DE 2934614 C2 DE2934614 C2 DE 2934614C2
- Authority
- DE
- Germany
- Prior art keywords
- chlorination
- xylene
- mixture
- terephthalaldehyde
- hexamethylenetetramine
- 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
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims abstract description 6
- IZALUMVGBVKPJD-UHFFFAOYSA-N benzene-1,3-dicarbaldehyde Chemical compound O=CC1=CC=CC(C=O)=C1 IZALUMVGBVKPJD-UHFFFAOYSA-N 0.000 title claims description 5
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 38
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims abstract description 32
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000004312 hexamethylene tetramine Substances 0.000 claims abstract description 16
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims abstract description 16
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 21
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 abstract description 14
- 150000001299 aldehydes Chemical class 0.000 abstract description 12
- 239000008096 xylene Substances 0.000 abstract description 3
- 229960004011 methenamine Drugs 0.000 description 14
- 239000000047 product Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VOWDXSFJQOEFSH-UHFFFAOYSA-N 1,4-bis(dichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=C(C(Cl)Cl)C=C1 VOWDXSFJQOEFSH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 1
- RGDYIHSZBVIIND-UHFFFAOYSA-N 1-(dichloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(C(Cl)Cl)C=C1 RGDYIHSZBVIIND-UHFFFAOYSA-N 0.000 description 1
- NVLHGZIXTRYOKT-UHFFFAOYSA-N 1-chloro-2,3-dimethylbenzene Chemical group CC1=CC=CC(Cl)=C1C NVLHGZIXTRYOKT-UHFFFAOYSA-N 0.000 description 1
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- IWLBIFVMPLUHLK-UHFFFAOYSA-N azane;formaldehyde Chemical compound N.O=C IWLBIFVMPLUHLK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 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
- 230000003287 optical effect Effects 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
-
- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
- C07C45/565—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom by reaction with hexamethylene-tetramine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2934614A DE2934614C2 (de) | 1979-08-28 | 1979-08-28 | Verfahren zur Herstellung von Terephthalaldehyd bzw. Isophthalaldehyd |
| EP80104456A EP0026291B1 (de) | 1979-08-28 | 1980-07-29 | Verfahren zur Herstellung von Terephthalaldehyd bzw. Isophthalaldehyd |
| AT80104456T ATE2421T1 (de) | 1979-08-28 | 1980-07-29 | Verfahren zur herstellung von terephthalaldehyd bzw. isophthalaldehyd. |
| DE8080104456T DE3061902D1 (en) | 1979-08-28 | 1980-07-29 | Process for the preparation of terephthalaldehyde or isophthalaldehyde |
| JP11715880A JPS5634653A (en) | 1979-08-28 | 1980-08-27 | Manufacture of terephthalaldehyde or isophthalaldehyde form ppxylol or mmxylol |
| US06/350,905 US4465865A (en) | 1979-08-28 | 1982-02-22 | Method of preparing terephthalic aldehyde and isophthalic aldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2934614A DE2934614C2 (de) | 1979-08-28 | 1979-08-28 | Verfahren zur Herstellung von Terephthalaldehyd bzw. Isophthalaldehyd |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2934614A1 DE2934614A1 (de) | 1981-03-26 |
| DE2934614C2 true DE2934614C2 (de) | 1982-05-06 |
Family
ID=6079413
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2934614A Expired DE2934614C2 (de) | 1979-08-28 | 1979-08-28 | Verfahren zur Herstellung von Terephthalaldehyd bzw. Isophthalaldehyd |
| DE8080104456T Expired DE3061902D1 (en) | 1979-08-28 | 1980-07-29 | Process for the preparation of terephthalaldehyde or isophthalaldehyde |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8080104456T Expired DE3061902D1 (en) | 1979-08-28 | 1980-07-29 | Process for the preparation of terephthalaldehyde or isophthalaldehyde |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4465865A (en, 2012) |
| EP (1) | EP0026291B1 (en, 2012) |
| JP (1) | JPS5634653A (en, 2012) |
| AT (1) | ATE2421T1 (en, 2012) |
| DE (2) | DE2934614C2 (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4845305A (en) * | 1988-07-07 | 1989-07-04 | National Starch And Chemical Corporation | Process for the preparation of isophthaladehyde |
| KR100651394B1 (ko) * | 2001-08-10 | 2006-11-28 | 에스케이 주식회사 | 이소프탈알데하이드의 제조방법 |
| US6891069B1 (en) * | 2004-01-30 | 2005-05-10 | Ethicon, Inc. | Synthesis of 4-substituted phthalaldehyde |
| KR100657744B1 (ko) | 2005-01-26 | 2006-12-13 | 주식회사 엘지화학 | 테레프탈알데히드의 정제방법 |
| KR100754499B1 (ko) * | 2005-05-10 | 2007-09-03 | 주식회사 엘지화학 | 아로마틱 디알데히드 분리 방법, 및 장치 |
| WO2008023836A1 (fr) * | 2006-08-23 | 2008-02-28 | Ube Industries, Ltd. | Procédé de fabrication d'un composé du benzaldéhyde |
| CN103980130A (zh) * | 2014-05-16 | 2014-08-13 | 南京理工大学 | 1,4-二（3-氨基-2,4,6-三硝基苯乙烯基）苯化合物、制备方法及其应用 |
| RU2633366C1 (ru) * | 2016-12-08 | 2017-10-12 | федеральное государственное бюджетное образовательное учреждение высшего образования "Казанский национальный исследовательский технологический университет" (ФГБОУ ВО "КНИТУ") | Способ получения терефталевого альдегида |
| RU2633365C1 (ru) * | 2016-12-08 | 2017-10-12 | федеральное государственное бюджетное образовательное учреждение высшего образования "Казанский национальный исследовательский технологический университет" (ФГБОУ ВО "КНИТУ") | Способ получения терефталевого альдегида |
| CN111704534A (zh) * | 2020-06-15 | 2020-09-25 | 杭州迈科瑞科技有限公司 | 一种使用微通道反应器连续化工业生产对苯二甲醛的工艺 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3081347A (en) * | 1958-12-29 | 1963-03-12 | Exxon Research Engineering Co | Preparation of polyaminomethyl aromatic compounds |
| DE2339086A1 (de) * | 1973-08-02 | 1975-02-20 | Dynamit Nobel Ag | Verfahren zur herstellung von terephthaldialdehyd |
| US4085147A (en) * | 1976-02-05 | 1978-04-18 | Shell Oil Company | Preparation of meta-aryloxy-benzaldehydes |
| US4108904A (en) * | 1976-09-22 | 1978-08-22 | American Cyanamid Company | Process for the preparation of m-phenoxybenzaldehyde |
| DE2860613D1 (en) * | 1977-12-30 | 1981-04-30 | Ciba Geigy Ag | Process for the preparation of o-phthalic aldehydes optionally having several substituents |
-
1979
- 1979-08-28 DE DE2934614A patent/DE2934614C2/de not_active Expired
-
1980
- 1980-07-29 EP EP80104456A patent/EP0026291B1/de not_active Expired
- 1980-07-29 DE DE8080104456T patent/DE3061902D1/de not_active Expired
- 1980-07-29 AT AT80104456T patent/ATE2421T1/de not_active IP Right Cessation
- 1980-08-27 JP JP11715880A patent/JPS5634653A/ja active Granted
-
1982
- 1982-02-22 US US06/350,905 patent/US4465865A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0026291B1 (de) | 1983-02-09 |
| US4465865A (en) | 1984-08-14 |
| ATE2421T1 (de) | 1983-03-15 |
| JPS6351133B2 (en, 2012) | 1988-10-13 |
| EP0026291A1 (de) | 1981-04-08 |
| JPS5634653A (en) | 1981-04-06 |
| DE2934614A1 (de) | 1981-03-26 |
| DE3061902D1 (en) | 1983-03-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8330 | Complete renunciation |