DE3040295A1 - Verfahren zur herstellung von aromatischen carbonsaeurechloriden - Google Patents
Verfahren zur herstellung von aromatischen carbonsaeurechloridenInfo
- Publication number
- DE3040295A1 DE3040295A1 DE19803040295 DE3040295A DE3040295A1 DE 3040295 A1 DE3040295 A1 DE 3040295A1 DE 19803040295 DE19803040295 DE 19803040295 DE 3040295 A DE3040295 A DE 3040295A DE 3040295 A1 DE3040295 A1 DE 3040295A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- oxide
- thionyl chloride
- aromatic carboxylic
- carboxylic acid
- 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- Withdrawn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
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 title 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 title 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 36
- 239000003054 catalyst Substances 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- -1 aromatic carboxylic acid chlorides Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 7
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 claims 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 10
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- UZPFIKMCNFEHFO-UHFFFAOYSA-N [ethyl(phenyl)phosphoryl]methylbenzene Chemical compound C=1C=CC=CC=1P(=O)(CC)CC1=CC=CC=C1 UZPFIKMCNFEHFO-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- MNZAKDODWSQONA-UHFFFAOYSA-N 1-dibutylphosphorylbutane Chemical compound CCCCP(=O)(CCCC)CCCC MNZAKDODWSQONA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEGCITODQASXKH-UHFFFAOYSA-N [methyl(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(C)C1=CC=CC=C1 PEGCITODQASXKH-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- RDLZJCXTAYHYHX-UHFFFAOYSA-N dibenzylphosphorylmethylbenzene Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)(=O)CC1=CC=CC=C1 RDLZJCXTAYHYHX-UHFFFAOYSA-N 0.000 description 2
- XROMZTPZKHMHRY-UHFFFAOYSA-N dimethylphosphorylmethylbenzene Chemical compound CP(C)(=O)CC1=CC=CC=C1 XROMZTPZKHMHRY-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ZJLKUMPDEXOUBN-UHFFFAOYSA-N 1-[bis(chloromethyl)phosphoryl]-3-chlorobenzene Chemical compound ClCP(=O)(CCl)C1=CC=CC(Cl)=C1 ZJLKUMPDEXOUBN-UHFFFAOYSA-N 0.000 description 1
- PPDZLUVUQQGIOJ-UHFFFAOYSA-N 1-dihexylphosphorylhexane Chemical compound CCCCCCP(=O)(CCCCCC)CCCCCC PPDZLUVUQQGIOJ-UHFFFAOYSA-N 0.000 description 1
- DFGYDPMXPAQIOD-UHFFFAOYSA-N 1-dinaphthalen-1-ylphosphorylnaphthalene Chemical compound C1=CC=C2C(P(C=3C4=CC=CC=C4C=CC=3)(C=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 DFGYDPMXPAQIOD-UHFFFAOYSA-N 0.000 description 1
- FSTTVKGSJLFJAC-UHFFFAOYSA-N 1-diphenylphosphoryl-4-methylbenzene Chemical compound C1=CC(C)=CC=C1P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 FSTTVKGSJLFJAC-UHFFFAOYSA-N 0.000 description 1
- GEZGQQFKEOIGJS-UHFFFAOYSA-N 2-di(propan-2-yl)phosphorylpropane Chemical compound CC(C)P(=O)(C(C)C)C(C)C GEZGQQFKEOIGJS-UHFFFAOYSA-N 0.000 description 1
- LFEWXDOYPCWFHR-UHFFFAOYSA-N 4-(4-carboxybenzoyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C=C1 LFEWXDOYPCWFHR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UCIDBUPCEWBAAF-UHFFFAOYSA-N ClC=1C=C(C=CC=1)[PH2]=O Chemical compound ClC=1C=C(C=CC=1)[PH2]=O UCIDBUPCEWBAAF-UHFFFAOYSA-N 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- UWCPYKQBIPYOLX-UHFFFAOYSA-N benzene-1,3,5-tricarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 UWCPYKQBIPYOLX-UHFFFAOYSA-N 0.000 description 1
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- NTWZKDSMPFHONS-UHFFFAOYSA-N diethylphosphorylbenzene Chemical compound CCP(=O)(CC)C1=CC=CC=C1 NTWZKDSMPFHONS-UHFFFAOYSA-N 0.000 description 1
- GWZCCUDJHOGOSO-UHFFFAOYSA-N diphenic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1C(O)=O GWZCCUDJHOGOSO-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803040295 DE3040295A1 (de) | 1980-10-25 | 1980-10-25 | Verfahren zur herstellung von aromatischen carbonsaeurechloriden |
| EP81108189A EP0050775B1 (de) | 1980-10-25 | 1981-10-12 | Verfahren zur Herstellung von aromatischen Carbonsäurechloriden |
| DE8181108189T DE3160881D1 (en) | 1980-10-25 | 1981-10-12 | Process for the production of aromatic carboxylic-acid chlorides |
| US06/312,224 US4382898A (en) | 1980-10-25 | 1981-10-19 | Process for the production of aromatic carboxylic acid chlorides |
| JP56167324A JPS5799553A (en) | 1980-10-25 | 1981-10-21 | Manufacture of aromatic carboxylic acid chloride |
| CA000388630A CA1183550A (en) | 1980-10-25 | 1981-10-23 | Process for the production of aromatic carboxylic acid chlorides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803040295 DE3040295A1 (de) | 1980-10-25 | 1980-10-25 | Verfahren zur herstellung von aromatischen carbonsaeurechloriden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3040295A1 true DE3040295A1 (de) | 1982-06-03 |
Family
ID=6115175
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803040295 Withdrawn DE3040295A1 (de) | 1980-10-25 | 1980-10-25 | Verfahren zur herstellung von aromatischen carbonsaeurechloriden |
| DE8181108189T Expired DE3160881D1 (en) | 1980-10-25 | 1981-10-12 | Process for the production of aromatic carboxylic-acid chlorides |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8181108189T Expired DE3160881D1 (en) | 1980-10-25 | 1981-10-12 | Process for the production of aromatic carboxylic-acid chlorides |
Country Status (5)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4693851A (en) * | 1985-04-09 | 1987-09-15 | Raychem Corporation | Purification of acid halides |
| DE3927146A1 (de) * | 1989-08-17 | 1991-02-21 | Basf Ag | Verfahren zur herstellung von chlorcarbonsaeurechloriden |
| DE102004057146A1 (de) * | 2004-11-26 | 2006-06-01 | Basf Ag | Verfahren zur Herstellung von Phthalsäuredichlorid |
| KR101430949B1 (ko) * | 2005-12-01 | 2014-08-18 | 바스프 에스이 | 술폰아미드의 제조 방법 |
| MX2010003148A (es) * | 2007-10-12 | 2010-04-01 | Basf Se | Procedimiento para la preparacion de diamidas de acido sulfonico. |
| CN107290874B (zh) * | 2017-07-05 | 2023-10-31 | 浙江大学 | 大带宽电光调制器 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1127095A (en) * | 1967-05-11 | 1968-09-11 | Aerojet General Co | Preparation of tri-mesoyl chloride |
| NL175521C (nl) * | 1973-04-26 | 1984-11-16 | Hoechst Ag | Werkwijze voor het bereiden van carbonzuurchloriden. |
-
1980
- 1980-10-25 DE DE19803040295 patent/DE3040295A1/de not_active Withdrawn
-
1981
- 1981-10-12 DE DE8181108189T patent/DE3160881D1/de not_active Expired
- 1981-10-12 EP EP81108189A patent/EP0050775B1/de not_active Expired
- 1981-10-19 US US06/312,224 patent/US4382898A/en not_active Expired - Fee Related
- 1981-10-21 JP JP56167324A patent/JPS5799553A/ja active Granted
- 1981-10-23 CA CA000388630A patent/CA1183550A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6412255B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-02-28 |
| DE3160881D1 (en) | 1983-10-20 |
| EP0050775B1 (de) | 1983-09-14 |
| EP0050775A3 (en) | 1982-06-30 |
| US4382898A (en) | 1983-05-10 |
| EP0050775A2 (de) | 1982-05-05 |
| CA1183550A (en) | 1985-03-05 |
| JPS5799553A (en) | 1982-06-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |