DE10258588A1 - Verfahren zur Decarboxylierung von Dicarbonsäuren - Google Patents
Verfahren zur Decarboxylierung von Dicarbonsäuren Download PDFInfo
- Publication number
- DE10258588A1 DE10258588A1 DE10258588A DE10258588A DE10258588A1 DE 10258588 A1 DE10258588 A1 DE 10258588A1 DE 10258588 A DE10258588 A DE 10258588A DE 10258588 A DE10258588 A DE 10258588A DE 10258588 A1 DE10258588 A1 DE 10258588A1
- Authority
- DE
- Germany
- Prior art keywords
- fluidized bed
- ethylenedioxythiophene
- reaction
- dicarboxylic acid
- carried out
- 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.)
- Withdrawn
Links
- NWIYUAISDYJVMZ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid Chemical compound O1CCOC2=C(C(=O)O)SC(C(O)=O)=C21 NWIYUAISDYJVMZ-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 239000007787 solid Substances 0.000 title claims abstract description 17
- 150000001991 dicarboxylic acids Chemical class 0.000 title claims abstract description 8
- 238000006114 decarboxylation reaction Methods 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 239000002904 solvent Substances 0.000 claims abstract description 11
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 26
- 239000007789 gas Substances 0.000 claims description 22
- 239000002245 particle Substances 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical class N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 239000007858 starting material Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical class O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
- 239000011149 active material Substances 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 229910002092 carbon dioxide Chemical class 0.000 claims description 3
- 239000001569 carbon dioxide Chemical class 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 150000001879 copper Chemical class 0.000 claims description 3
- 229910052756 noble gas Inorganic materials 0.000 claims description 3
- 150000002835 noble gases Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000012546 transfer Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 7
- 239000011261 inert gas Substances 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 229940116318 copper carbonate Drugs 0.000 description 2
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 2
- 238000005243 fluidization Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- VJPALIAORYSTKL-UHFFFAOYSA-N 3,4-dimethoxythiophene-2,5-dicarboxylic acid Chemical compound COC1=C(C(O)=O)SC(C(O)=O)=C1OC VJPALIAORYSTKL-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical class [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 239000006004 Quartz sand Substances 0.000 description 1
- QLMIABXHLCKHRF-UHFFFAOYSA-N [Cr+3].[Cu]=O Chemical compound [Cr+3].[Cu]=O QLMIABXHLCKHRF-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000012768 molten material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10258588A DE10258588A1 (de) | 2002-12-16 | 2002-12-16 | Verfahren zur Decarboxylierung von Dicarbonsäuren |
| PCT/EP2003/013679 WO2004055023A1 (de) | 2002-12-16 | 2003-12-04 | Verfahren zur decarboxylierung von dicarbonsäuren |
| JP2004559751A JP4695880B2 (ja) | 2002-12-16 | 2003-12-04 | ジカルボン酸の脱カルボキシル化法 |
| EP03780117A EP1575961B1 (de) | 2002-12-16 | 2003-12-04 | Verfahren zur decarboxylierung von dicarbonsäuren |
| AU2003288225A AU2003288225A1 (en) | 2002-12-16 | 2003-12-04 | Method for the decarboxylation of dicarboxylic acids |
| CNB2003801062452A CN100338070C (zh) | 2002-12-16 | 2003-12-04 | 二羧酸脱羧的方法 |
| US10/538,995 US7671217B2 (en) | 2002-12-16 | 2003-12-04 | Method for the decarboxylation of dicarboxylic acids |
| DE50307534T DE50307534D1 (de) | 2002-12-16 | 2003-12-04 | Verfahren zur decarboxylierung von dicarbonsäuren |
| AT03780117T ATE365168T1 (de) | 2002-12-16 | 2003-12-04 | Verfahren zur decarboxylierung von dicarbonsäuren |
| KR1020057011049A KR101057890B1 (ko) | 2002-12-16 | 2003-12-04 | 디카르복실산의 탈카르복실화 방법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10258588A DE10258588A1 (de) | 2002-12-16 | 2002-12-16 | Verfahren zur Decarboxylierung von Dicarbonsäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10258588A1 true DE10258588A1 (de) | 2004-06-24 |
Family
ID=32336336
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10258588A Withdrawn DE10258588A1 (de) | 2002-12-16 | 2002-12-16 | Verfahren zur Decarboxylierung von Dicarbonsäuren |
| DE50307534T Expired - Lifetime DE50307534D1 (de) | 2002-12-16 | 2003-12-04 | Verfahren zur decarboxylierung von dicarbonsäuren |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50307534T Expired - Lifetime DE50307534D1 (de) | 2002-12-16 | 2003-12-04 | Verfahren zur decarboxylierung von dicarbonsäuren |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7671217B2 (enExample) |
| EP (1) | EP1575961B1 (enExample) |
| JP (1) | JP4695880B2 (enExample) |
| KR (1) | KR101057890B1 (enExample) |
| CN (1) | CN100338070C (enExample) |
| AT (1) | ATE365168T1 (enExample) |
| AU (1) | AU2003288225A1 (enExample) |
| DE (2) | DE10258588A1 (enExample) |
| WO (1) | WO2004055023A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102241691B (zh) * | 2011-07-13 | 2014-03-26 | 西北大学 | 3,4-乙撑二氧噻吩的脱羧方法 |
| CN103408415A (zh) * | 2013-07-22 | 2013-11-27 | 张家港保税区超威电化技术服务有限公司 | 一种电容级2-丁基癸二酸的合成方法 |
| CN106366094B (zh) * | 2016-08-31 | 2018-09-11 | 贝利化学（张家港）有限公司 | 一种噻吩并[3,4-b] -1,4-二氧杂-5, 7-二羧酸的脱羧方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2453103A (en) * | 1944-02-25 | 1948-11-02 | Du Pont | Decarboxylation of 3,4-dihydroxy-2,5-dicarboxythiophene |
| DE3903973A1 (de) * | 1989-02-10 | 1990-08-16 | Bayer Ag | Neue heterocyclische verbindungen, ihre herstellung und ihre verwendung |
| CA2051593A1 (en) * | 1990-09-20 | 1992-03-21 | Stephen Wayne King | Process for the preparation of cyclic ethers |
| US5111327A (en) * | 1991-03-04 | 1992-05-05 | General Electric Company | Substituted 3,4-polymethylenedioxythiophenes, and polymers and electro responsive devices made therefrom |
| JP4590049B2 (ja) * | 1999-10-18 | 2010-12-01 | 住友精化株式会社 | ベンゾ［ｂ］チオフェン誘導体の製造方法 |
| DE10016723A1 (de) * | 2000-04-04 | 2001-10-11 | Bayer Ag | Verfahren zur Herstellung von Dialkoxythiophenen und Alkylendioxythiophenen |
| DE10029078A1 (de) * | 2000-06-13 | 2001-12-20 | Bayer Ag | Verfahren zur Herstellung von 3,4-Alkylendioxythiophenen |
-
2002
- 2002-12-16 DE DE10258588A patent/DE10258588A1/de not_active Withdrawn
-
2003
- 2003-12-04 US US10/538,995 patent/US7671217B2/en not_active Expired - Fee Related
- 2003-12-04 KR KR1020057011049A patent/KR101057890B1/ko not_active Expired - Fee Related
- 2003-12-04 JP JP2004559751A patent/JP4695880B2/ja not_active Expired - Fee Related
- 2003-12-04 AT AT03780117T patent/ATE365168T1/de active
- 2003-12-04 AU AU2003288225A patent/AU2003288225A1/en not_active Abandoned
- 2003-12-04 WO PCT/EP2003/013679 patent/WO2004055023A1/de not_active Ceased
- 2003-12-04 DE DE50307534T patent/DE50307534D1/de not_active Expired - Lifetime
- 2003-12-04 CN CNB2003801062452A patent/CN100338070C/zh not_active Expired - Fee Related
- 2003-12-04 EP EP03780117A patent/EP1575961B1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR20050089828A (ko) | 2005-09-08 |
| ATE365168T1 (de) | 2007-07-15 |
| DE50307534D1 (de) | 2007-08-02 |
| JP4695880B2 (ja) | 2011-06-08 |
| EP1575961B1 (de) | 2007-06-20 |
| US7671217B2 (en) | 2010-03-02 |
| CN1759119A (zh) | 2006-04-12 |
| US20060149083A1 (en) | 2006-07-06 |
| WO2004055023A1 (de) | 2004-07-01 |
| EP1575961A1 (de) | 2005-09-21 |
| AU2003288225A1 (en) | 2004-07-09 |
| JP2006515842A (ja) | 2006-06-08 |
| KR101057890B1 (ko) | 2011-08-19 |
| CN100338070C (zh) | 2007-09-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: BAYER TECHNOLOGY SERVICES GMBH, 51373 LEVERKUSEN, |
|
| 8139 | Disposal/non-payment of the annual fee |