DE2656126A1 - Verfahren zur herstellung von saeurechloriden durch katalytische heissphosgenierung von carbonsaeuren - Google Patents
Verfahren zur herstellung von saeurechloriden durch katalytische heissphosgenierung von carbonsaeurenInfo
- Publication number
- DE2656126A1 DE2656126A1 DE19762656126 DE2656126A DE2656126A1 DE 2656126 A1 DE2656126 A1 DE 2656126A1 DE 19762656126 DE19762656126 DE 19762656126 DE 2656126 A DE2656126 A DE 2656126A DE 2656126 A1 DE2656126 A1 DE 2656126A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- catalyst
- production
- acid chlorides
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 19
- 239000002253 acid Substances 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 title description 3
- 230000003197 catalytic effect Effects 0.000 title description 2
- 150000004653 carbonic acids Chemical class 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 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 9
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- 150000001805 chlorine compounds Chemical class 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 4
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004420 diamide group Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 7
- 150000008065 acid anhydrides Chemical class 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 5
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 5
- LLDYJCVQJMCQMF-UHFFFAOYSA-N 2,4,5,6-tetramethylbenzene-1,3-dicarboxamide Chemical compound CC1=C(C)C(C(N)=O)=C(C)C(C(N)=O)=C1C LLDYJCVQJMCQMF-UHFFFAOYSA-N 0.000 description 3
- WFSGQBNCVASPMW-UHFFFAOYSA-N 2-ethylhexanoyl chloride Chemical compound CCCCC(CC)C(Cl)=O WFSGQBNCVASPMW-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- -1 carboxylic acid chlorides Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- SVWDHNLFFDIWHM-UHFFFAOYSA-N 1-n,1-n,3-n,3-n-tetramethylbenzene-1,3-dicarboxamide Chemical compound CN(C)C(=O)C1=CC=CC(C(=O)N(C)C)=C1 SVWDHNLFFDIWHM-UHFFFAOYSA-N 0.000 description 1
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7540209A FR2337121B1 (fr) | 1975-12-31 | 1975-12-31 | Phosgenation a chaud des acides en chlorures d'acides avec des diamides d'acides carboxyliques comme catalyseurs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2656126A1 true DE2656126A1 (de) | 1977-07-14 |
Family
ID=9164352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762656126 Pending DE2656126A1 (de) | 1975-12-31 | 1976-12-10 | Verfahren zur herstellung von saeurechloriden durch katalytische heissphosgenierung von carbonsaeuren |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS52102205A (enExample) |
| BE (1) | BE850040A (enExample) |
| DE (1) | DE2656126A1 (enExample) |
| DK (1) | DK587976A (enExample) |
| FR (1) | FR2337121B1 (enExample) |
| IT (1) | IT1068740B (enExample) |
| LU (1) | LU76485A1 (enExample) |
| NL (1) | NL7614323A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014030038A1 (en) * | 2012-08-23 | 2014-02-27 | Galaxy Surfactants Ltd. | Method to produce n-acyl amino acid surfactants using n-acyl amino acid surfactants or the corresponding anhydrides as catalysts |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5235082B2 (ja) * | 2008-02-25 | 2013-07-10 | 日本曹達株式会社 | クロル化方法及びその反応終点の検知方法 |
| CN101348427B (zh) | 2008-08-30 | 2011-06-29 | 西北师范大学 | 异壬酰氯的简便合成方法 |
| CN114478300B (zh) * | 2021-07-16 | 2023-05-23 | 丰益表面活性材料（连云港）有限公司 | 新型酰氯催化剂及其制备方法与应用 |
-
1975
- 1975-12-31 FR FR7540209A patent/FR2337121B1/fr not_active Expired
-
1976
- 1976-12-10 DE DE19762656126 patent/DE2656126A1/de active Pending
- 1976-12-20 IT IT7004076A patent/IT1068740B/it active
- 1976-12-23 NL NL7614323A patent/NL7614323A/xx not_active Application Discontinuation
- 1976-12-28 LU LU76485A patent/LU76485A1/xx unknown
- 1976-12-28 JP JP15764076A patent/JPS52102205A/ja active Pending
- 1976-12-30 DK DK587976A patent/DK587976A/da unknown
- 1976-12-31 BE BE173794A patent/BE850040A/xx unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014030038A1 (en) * | 2012-08-23 | 2014-02-27 | Galaxy Surfactants Ltd. | Method to produce n-acyl amino acid surfactants using n-acyl amino acid surfactants or the corresponding anhydrides as catalysts |
| CN104640839A (zh) * | 2012-08-23 | 2015-05-20 | 银河表面活性剂有限公司 | 使用n-酰基氨基酸表面活性剂或对应的酸酐作为催化剂生产n-酰基氨基酸表面活性剂的方法 |
| JP2015526460A (ja) * | 2012-08-23 | 2015-09-10 | ギャラクシー サーファクタンツ リミテッド | 触媒としてｎ−アシルアミノ酸界面活性剤またはその対応する無水物を使用するｎ−アシルアミノ酸界面活性剤を製造する方法 |
| US9187407B2 (en) | 2012-08-23 | 2015-11-17 | Galaxy Surfactants Ltd. | Method to produce N-acyl amino acid surfactants using N-acyl amino acid surfactants or the corresponding anhydrides as catalysts |
| EP2888226B1 (en) | 2012-08-23 | 2016-07-20 | Galaxy Surfactants Ltd. | Method to produce n-acyl amino acid surfactants using n-acyl amino acid surfactants or the corresponding anhydrides as catalysts |
| CN104640839B (zh) * | 2012-08-23 | 2017-02-15 | 银河表面活性剂有限公司 | 使用n‑酰基氨基酸表面活性剂或对应的酸酐作为催化剂生产n‑酰基氨基酸表面活性剂的方法 |
| RU2624026C2 (ru) * | 2012-08-23 | 2017-06-30 | Гэлакси Сёфэктентс Лтд. | Способ получения основанных на n-ациламинокислоте поверхностно-активных веществ с применением основанных на n-ациламинокислоте поверхностно-активных веществ или соответствующих ангидридов в качестве катализаторов |
Also Published As
| Publication number | Publication date |
|---|---|
| LU76485A1 (enExample) | 1978-07-10 |
| IT1068740B (it) | 1985-03-21 |
| DK587976A (da) | 1977-07-01 |
| JPS52102205A (en) | 1977-08-27 |
| FR2337121A1 (en) | 1977-07-29 |
| FR2337121B1 (fr) | 1978-07-28 |
| NL7614323A (nl) | 1977-07-04 |
| BE850040A (fr) | 1977-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHW | Rejection |