DE1593175A1 - Verfahren zur Herstellung von Dicarbonsaeuren - Google Patents
Verfahren zur Herstellung von DicarbonsaeurenInfo
- Publication number
- DE1593175A1 DE1593175A1 DE19661593175 DE1593175A DE1593175A1 DE 1593175 A1 DE1593175 A1 DE 1593175A1 DE 19661593175 DE19661593175 DE 19661593175 DE 1593175 A DE1593175 A DE 1593175A DE 1593175 A1 DE1593175 A1 DE 1593175A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- reaction
- hydroxide
- water
- nan
- 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 14
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 title description 3
- 239000002253 acid Substances 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- CWNNYYIZGGDCHS-UHFFFAOYSA-N 2-methylideneglutaric acid Chemical compound OC(=O)CCC(=C)C(O)=O CWNNYYIZGGDCHS-UHFFFAOYSA-N 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000011084 recovery Methods 0.000 claims description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 230000020477 pH reduction Effects 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 1
- FVUOCOCBVMNVGQ-IAGONARPSA-N 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin Chemical compound C=1C=C(O)C=CC=1/C=C/C(=O)OC1C(O)C(OC(=O)\C=C\C=2C=CC(O)=CC=2)C(CO)OC1OC(C(C1=C(O)C=C(O)C=C1O1)=O)=C1C1=CC=C(O)C=C1 FVUOCOCBVMNVGQ-IAGONARPSA-N 0.000 claims 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 1
- 239000005642 Oleic acid Substances 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 1
- 235000015250 liver sausages Nutrition 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000000605 extraction Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- -1 unsaturated aliphatic dicarboxylic acids Chemical class 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DOBUSJIVSSJEDA-UHFFFAOYSA-L 1,3-dioxa-2$l^{6}-thia-4-mercuracyclobutane 2,2-dioxide Chemical compound [Hg+2].[O-]S([O-])(=O)=O DOBUSJIVSSJEDA-UHFFFAOYSA-L 0.000 description 1
- NGCJVMZXRCLPRQ-UHFFFAOYSA-N 2-methylidenepentanedinitrile Chemical compound N#CC(=C)CCC#N NGCJVMZXRCLPRQ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical class [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- AFPMYNVTBFMKOI-UHFFFAOYSA-N ethene;pentanedioic acid Chemical compound C=C.OC(=O)CCCC(O)=O AFPMYNVTBFMKOI-UHFFFAOYSA-N 0.000 description 1
- ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- ZQBVUULQVWCGDQ-UHFFFAOYSA-N propan-1-ol;propan-2-ol Chemical compound CCCO.CC(C)O ZQBVUULQVWCGDQ-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48940665A | 1965-09-22 | 1965-09-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1593175A1 true DE1593175A1 (de) | 1970-07-30 |
Family
ID=23943725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661593175 Pending DE1593175A1 (de) | 1965-09-22 | 1966-09-22 | Verfahren zur Herstellung von Dicarbonsaeuren |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE687139A (enrdf_load_html_response) |
| DE (1) | DE1593175A1 (enrdf_load_html_response) |
| FR (1) | FR1495197A (enrdf_load_html_response) |
| GB (1) | GB1122448A (enrdf_load_html_response) |
| NL (1) | NL6613239A (enrdf_load_html_response) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113563180A (zh) * | 2021-07-26 | 2021-10-29 | 广东嘉博制药有限公司 | （e）-4-烯-1,8-辛二酸的制备方法 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2902095B1 (fr) * | 2006-06-09 | 2008-12-05 | Rhodia Recherches & Tech | Procede de transformation de composes nitriles en acides carboxyliques et esters correspondants |
| FR2909088B1 (fr) * | 2006-11-24 | 2009-02-13 | Rhodia Recherches & Tech | Procede de transformation de composes nitriles en acides carboxyliques et esters correspondants |
-
1966
- 1966-09-15 GB GB4124366A patent/GB1122448A/en not_active Expired
- 1966-09-20 NL NL6613239A patent/NL6613239A/xx unknown
- 1966-09-20 BE BE687139D patent/BE687139A/xx unknown
- 1966-09-21 FR FR47731A patent/FR1495197A/fr not_active Expired
- 1966-09-22 DE DE19661593175 patent/DE1593175A1/de active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113563180A (zh) * | 2021-07-26 | 2021-10-29 | 广东嘉博制药有限公司 | （e）-4-烯-1,8-辛二酸的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1495197A (fr) | 1967-09-15 |
| NL6613239A (enrdf_load_html_response) | 1967-03-23 |
| BE687139A (enrdf_load_html_response) | 1967-03-01 |
| GB1122448A (en) | 1968-08-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2507461C3 (de) | Verfahren zur Herstellung von 2,2- Dimethylolalkanalen | |
| DE2702582A1 (de) | Verfahren zur herstellung von trimethylolalkanen | |
| DE4138981A1 (de) | Verfahren zur herstellung von 3-hydroxyalkanalen | |
| WO2001051438A1 (de) | Verfahren zur herstellung von trimethylolalkanen | |
| EP0151241B1 (de) | Verfahren zur Herstellung von 1,4 Butandial | |
| DE1593175A1 (de) | Verfahren zur Herstellung von Dicarbonsaeuren | |
| EP0110031B1 (de) | Verfahren zur Herstellung von 1,2-Diolen | |
| DE1793512C3 (de) | Verfahren zur Herstellung von 2,2- Dimethyl-3-hydroxypropanal | |
| DE102006041941A1 (de) | Verfahren zur Herstellung von 1,2-Diolen aus Carbonyl-Verbindungen | |
| EP0676390B1 (de) | Verfahren zur Herstellung von 1-Aminocyclopropancarbonsäurehydrochlorid | |
| DE2151716B2 (de) | Verfahren zur Hersteilung von Estern von 2-Aryl-2-dimethylamino-lalkanolen | |
| EP0474057B1 (de) | Verfahren zur Herstellung von N-(2-Chlor-pyridin-5-yl-methyl)-ethylendiamin | |
| DE2636278A1 (de) | Verfahren zur herstellung von dialkylketalen | |
| DE1918253A1 (de) | Verbessertes Verfahren zur Herstellung von 3-Hydroxyisoxazolverbindungen | |
| DE707426C (de) | Herstellung von ungesaettigten Aldehyden | |
| DE708513C (de) | Verfahren zur Herstellung von Oxymethylencarbonsaeureestern durch Kondensation von Ameisensaeureestern mit aliphatischen Carbonsaeureestern | |
| DE2221706C2 (de) | Verfahren zur Herstellung von 4-Hydroxybenzodioxolen | |
| DE2758883B2 (de) | Verfahren zur kontinuierlichen Herstellung von a -Hydroxy- ß , ß -dimethyl- γ -butyrolacton | |
| DE2053398C3 (de) | Verfahren zur Herstellung von substituierten Acylphenoxyalkyl-carbonsäuren | |
| DE69611493T2 (de) | Verfahren zur Herstellung von Benzolhalogenid | |
| DE2443080C3 (de) | Verfahren zur Herstellung von ' 2,4-Diamino-5-(3',4'3'-triinethoxybenzyl)-pyrhnidin | |
| DE1768983A1 (de) | N,N-Bis-halogenmethyl-carbaminsaeureester und Verfahren zu ihrer Herstellung | |
| DE892893C (de) | Verfahren zur Herstellung von Carbonsaeureestern | |
| AT353774B (de) | Verfahren zur herstellung von hydrochinon- dialkylaethern | |
| DE2551498C2 (de) | Verfahren zur Herstellung von Dichlorophen |