DE2657734A1 - Verfahren zur herstellung von saeurechloriden durch katalytische heissphosgenierung von carbonsaeuren - Google Patents
Verfahren zur herstellung von saeurechloriden durch katalytische heissphosgenierung von carbonsaeurenInfo
- Publication number
- DE2657734A1 DE2657734A1 DE19762657734 DE2657734A DE2657734A1 DE 2657734 A1 DE2657734 A1 DE 2657734A1 DE 19762657734 DE19762657734 DE 19762657734 DE 2657734 A DE2657734 A DE 2657734A DE 2657734 A1 DE2657734 A1 DE 2657734A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- catalyst
- reactor
- chloride
- production
- 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
- 239000002253 acid Substances 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 21
- 230000008569 process Effects 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 title description 5
- 230000003197 catalytic effect Effects 0.000 title description 3
- 150000004653 carbonic acids Chemical class 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims description 28
- 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 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 9
- 150000001805 chlorine compounds Chemical class 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 9
- 150000008064 anhydrides Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 4
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- WFSGQBNCVASPMW-UHFFFAOYSA-N 2-ethylhexanoyl chloride Chemical compound CCCCC(CC)C(Cl)=O WFSGQBNCVASPMW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 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
- 230000008901 benefit Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- TVPCUVQDVRZTAL-UHFFFAOYSA-N 2-ethylhexanoyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC(=O)C(CC)CCCC TVPCUVQDVRZTAL-UHFFFAOYSA-N 0.000 description 1
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-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
- TUWJQNVAGYRRHA-UHFFFAOYSA-N Menadiol dibutyrate Chemical compound C1=CC=C2C(OC(=O)CCC)=CC(C)=C(OC(=O)CCC)C2=C1 TUWJQNVAGYRRHA-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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 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
- -1 carboxylic acid chlorides Chemical class 0.000 description 1
- BWRHOYDPVJPXMF-UHFFFAOYSA-N cis-Caran Natural products C1C(C)CCC2C(C)(C)C12 BWRHOYDPVJPXMF-UHFFFAOYSA-N 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000004044 response Effects 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
- 239000002689 soil Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
-
- 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
- Y02P20/584—Recycling of catalysts
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 |
|---|---|---|---|
| FR7540210A FR2337122A1 (fr) | 1975-12-31 | 1975-12-31 | Catalyseurs phosphores pour la phosgenation des acides en chlorures d'acides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2657734A1 true DE2657734A1 (de) | 1977-07-07 |
Family
ID=9164353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762657734 Pending DE2657734A1 (de) | 1975-12-31 | 1976-12-20 | Verfahren zur herstellung von saeurechloriden durch katalytische heissphosgenierung von carbonsaeuren |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS52102206A (enExample) |
| BE (1) | BE850041A (enExample) |
| DE (1) | DE2657734A1 (enExample) |
| DK (1) | DK588076A (enExample) |
| FR (1) | FR2337122A1 (enExample) |
| LU (1) | LU76494A1 (enExample) |
| NL (1) | NL7614324A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0022484A1 (de) * | 1979-07-03 | 1981-01-21 | Bayer Ag | Verfahren zur Herstellung aromatischer Dicarbonsäuredichloride und ihre Verwendung bei der Herstellung von Polykondensaten |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 FR7540210A patent/FR2337122A1/fr active Granted
-
1976
- 1976-12-20 DE DE19762657734 patent/DE2657734A1/de active Pending
- 1976-12-23 NL NL7614324A patent/NL7614324A/xx not_active Application Discontinuation
- 1976-12-28 JP JP15764176A patent/JPS52102206A/ja active Pending
- 1976-12-29 LU LU76494A patent/LU76494A1/xx unknown
- 1976-12-30 DK DK588076A patent/DK588076A/da unknown
- 1976-12-31 BE BE173795A patent/BE850041A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0022484A1 (de) * | 1979-07-03 | 1981-01-21 | Bayer Ag | Verfahren zur Herstellung aromatischer Dicarbonsäuredichloride und ihre Verwendung bei der Herstellung von Polykondensaten |
Also Published As
| Publication number | Publication date |
|---|---|
| LU76494A1 (enExample) | 1978-07-10 |
| JPS52102206A (en) | 1977-08-27 |
| FR2337122A1 (fr) | 1977-07-29 |
| DK588076A (da) | 1977-07-01 |
| NL7614324A (nl) | 1977-07-04 |
| FR2337122B1 (enExample) | 1978-07-28 |
| BE850041A (fr) | 1977-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |