DE2053289A1 - Verfahren zur Herstellung von Delta 2,5 Cyclohexadien dicarbonsaure 1,2 durch Reduktion wäßriger Losungen von Alkali phthalat mit Alkahamalgam - Google Patents
Verfahren zur Herstellung von Delta 2,5 Cyclohexadien dicarbonsaure 1,2 durch Reduktion wäßriger Losungen von Alkali phthalat mit AlkahamalgamInfo
- Publication number
- DE2053289A1 DE2053289A1 DE19702053289 DE2053289A DE2053289A1 DE 2053289 A1 DE2053289 A1 DE 2053289A1 DE 19702053289 DE19702053289 DE 19702053289 DE 2053289 A DE2053289 A DE 2053289A DE 2053289 A1 DE2053289 A1 DE 2053289A1
- Authority
- DE
- Germany
- Prior art keywords
- alkali
- amalgam
- acid
- reaction
- solution
- 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
- 239000003513 alkali Substances 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 11
- 239000007864 aqueous solution Substances 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 title description 4
- NSMLBNDBJUCXCD-UHFFFAOYSA-N cyclohexa-2,5-diene-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C=CCC=C1)C(O)=O NSMLBNDBJUCXCD-UHFFFAOYSA-N 0.000 title 1
- 229910000497 Amalgam Inorganic materials 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 19
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical group [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 claims description 5
- 229910001023 sodium amalgam Inorganic materials 0.000 claims description 5
- -1 alkali metal phthalates Chemical class 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 229910000567 Amalgam (chemistry) Inorganic materials 0.000 claims description 2
- 238000005868 electrolysis reaction Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 239000012670 alkaline solution Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 description 20
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 150000007513 acids Chemical class 0.000 description 11
- 239000011734 sodium Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- ZSCAFJYAQAGJBT-UHFFFAOYSA-N cyclohexa-2,4-diene-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC=CC=C1 ZSCAFJYAQAGJBT-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- HQWKKEIVHQXCPI-UHFFFAOYSA-L disodium;phthalate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C([O-])=O HQWKKEIVHQXCPI-UHFFFAOYSA-L 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OYUWHGGWLCJJNP-UHFFFAOYSA-N 1,2-Dihydrophthalic acid Chemical compound OC(=O)C1C=CC=CC1C(O)=O OYUWHGGWLCJJNP-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- GJIIAJVOYIPUPY-UHFFFAOYSA-N 2-methylidenebut-3-enoic acid Chemical compound OC(=O)C(=C)C=C GJIIAJVOYIPUPY-UHFFFAOYSA-N 0.000 description 1
- 101100141312 Mus musculus Ripk1 gene Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical class OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- APGFPQCBDNWQSB-UHFFFAOYSA-N cyclohexa-1,3-diene-1-carboxylic acid Chemical class OC(=O)C1=CC=CCC1 APGFPQCBDNWQSB-UHFFFAOYSA-N 0.000 description 1
- XRCLQGMSELDJDX-UHFFFAOYSA-N cyclohexa-2,5-diene-1,2-dicarboxylic acid Chemical compound OC(=O)C1C=CCC=C1C(O)=O XRCLQGMSELDJDX-UHFFFAOYSA-N 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- GOMCKELMLXHYHH-UHFFFAOYSA-L dipotassium;phthalate Chemical compound [K+].[K+].[O-]C(=O)C1=CC=CC=C1C([O-])=O GOMCKELMLXHYHH-UHFFFAOYSA-L 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- WEGDVNIPLOLRJC-UHFFFAOYSA-M sodium;naphthalene-1-carboxylate Chemical compound [Na+].C1=CC=C2C(C(=O)[O-])=CC=CC2=C1 WEGDVNIPLOLRJC-UHFFFAOYSA-M 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000000126 substance Substances 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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702053289 DE2053289A1 (de) | 1970-10-30 | 1970-10-30 | Verfahren zur Herstellung von Delta 2,5 Cyclohexadien dicarbonsaure 1,2 durch Reduktion wäßriger Losungen von Alkali phthalat mit Alkahamalgam |
| US191130A US3880915A (en) | 1970-10-30 | 1971-10-20 | Method for preparation of {66 {hu 2,5{b -cyclohexadiene dicarboxylic acid-1,2 by reducing aqueous solutions of alkali phthalate with alkali amalgam |
| BE774490A BE774490A (fr) | 1970-10-30 | 1971-10-26 | Procede de preparation d'acide delta 2,5-cyclohexadiene- dicarboxylique, 1,2 par reduction de solutions aqueuses d'un phtalatealcalin avec un amalgame alcalin |
| FR7138753A FR2113348A5 (enExample) | 1970-10-30 | 1971-10-28 | |
| GB5065571A GB1358703A (en) | 1970-10-30 | 1971-10-29 | Preparation of delta2,5-dihydrophthalic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702053289 DE2053289A1 (de) | 1970-10-30 | 1970-10-30 | Verfahren zur Herstellung von Delta 2,5 Cyclohexadien dicarbonsaure 1,2 durch Reduktion wäßriger Losungen von Alkali phthalat mit Alkahamalgam |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2053289A1 true DE2053289A1 (de) | 1972-05-04 |
Family
ID=5786602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702053289 Pending DE2053289A1 (de) | 1970-10-30 | 1970-10-30 | Verfahren zur Herstellung von Delta 2,5 Cyclohexadien dicarbonsaure 1,2 durch Reduktion wäßriger Losungen von Alkali phthalat mit Alkahamalgam |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3880915A (enExample) |
| BE (1) | BE774490A (enExample) |
| DE (1) | DE2053289A1 (enExample) |
| FR (1) | FR2113348A5 (enExample) |
| GB (1) | GB1358703A (enExample) |
-
1970
- 1970-10-30 DE DE19702053289 patent/DE2053289A1/de active Pending
-
1971
- 1971-10-20 US US191130A patent/US3880915A/en not_active Expired - Lifetime
- 1971-10-26 BE BE774490A patent/BE774490A/xx unknown
- 1971-10-28 FR FR7138753A patent/FR2113348A5/fr not_active Expired
- 1971-10-29 GB GB5065571A patent/GB1358703A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2113348A5 (enExample) | 1972-06-23 |
| BE774490A (fr) | 1972-02-14 |
| US3880915A (en) | 1975-04-29 |
| GB1358703A (en) | 1974-07-03 |
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