CA1045150A - Process for the preparation of trans, trans-muconic acid - Google Patents
Process for the preparation of trans, trans-muconic acidInfo
- Publication number
- CA1045150A CA1045150A CA244,301A CA244301A CA1045150A CA 1045150 A CA1045150 A CA 1045150A CA 244301 A CA244301 A CA 244301A CA 1045150 A CA1045150 A CA 1045150A
- Authority
- CA
- Canada
- Prior art keywords
- trans
- acid
- preparation
- muconic acid
- beta
- 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.)
- Expired
Links
- TXXHDPDFNKHHGW-UHFFFAOYSA-N (2E,4E)-2,4-hexadienedioic acid Natural products OC(=O)C=CC=CC(O)=O TXXHDPDFNKHHGW-UHFFFAOYSA-N 0.000 title claims abstract description 12
- TXXHDPDFNKHHGW-ZPUQHVIOSA-N trans,trans-muconic acid Chemical compound OC(=O)\C=C\C=C\C(O)=O TXXHDPDFNKHHGW-ZPUQHVIOSA-N 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000003513 alkali Substances 0.000 claims abstract description 4
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003377 acid catalyst Substances 0.000 claims abstract description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical class C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VPZFYLQMPOIPKH-UHFFFAOYSA-N 1,1,1,2-tetramethoxyethane Chemical compound COCC(OC)(OC)OC VPZFYLQMPOIPKH-UHFFFAOYSA-N 0.000 description 1
- IKAACYWAXDLDPM-UHFFFAOYSA-N 1,2,3,4,4a,5-hexahydronaphthalene Chemical compound C1=CCC2CCCCC2=C1 IKAACYWAXDLDPM-UHFFFAOYSA-N 0.000 description 1
- KTZNVZJECQAMBV-UHFFFAOYSA-N 1-(cyclohexen-1-yl)pyrrolidine Chemical compound C1CCCN1C1=CCCCC1 KTZNVZJECQAMBV-UHFFFAOYSA-N 0.000 description 1
- YQJYYLUIHJCSQN-UHFFFAOYSA-N 2,2-dimethoxyhexanedioic acid Chemical compound COC(CCCC(O)=O)(OC)C(O)=O YQJYYLUIHJCSQN-UHFFFAOYSA-N 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000002841 Lewis acid Substances 0.000 description 1
- TXXHDPDFNKHHGW-CCAGOZQPSA-N Muconic acid Natural products OC(=O)\C=C/C=C\C(O)=O TXXHDPDFNKHHGW-CCAGOZQPSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007269 dehydrobromination reaction Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- AHJWSRRHTXRLAQ-UHFFFAOYSA-N tetramethoxymethane Chemical compound COC(OC)(OC)OC AHJWSRRHTXRLAQ-UHFFFAOYSA-N 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
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/46—Preparation of carboxylic acid esters from ketenes or polyketenes
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 |
|---|---|---|---|
| DE19752503313 DE2503313C3 (de) | 1975-01-28 | Verfahren zur Herstellung von transtrans-Muconsäure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1045150A true CA1045150A (en) | 1978-12-26 |
Family
ID=5937452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA244,301A Expired CA1045150A (en) | 1975-01-28 | 1976-01-27 | Process for the preparation of trans, trans-muconic acid |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4031136A (enExample) |
| JP (1) | JPS51100022A (enExample) |
| BE (1) | BE837990A (enExample) |
| BR (1) | BR7600410A (enExample) |
| CA (1) | CA1045150A (enExample) |
| DK (1) | DK31876A (enExample) |
| ES (1) | ES444542A1 (enExample) |
| FR (1) | FR2299304A1 (enExample) |
| GB (1) | GB1528101A (enExample) |
| IT (1) | IT1054503B (enExample) |
| LU (1) | LU74242A1 (enExample) |
| NL (1) | NL7600713A (enExample) |
| SE (1) | SE7600765L (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101842344B (zh) * | 2007-10-29 | 2014-04-30 | 隆萨股份公司 | 烷基3,3-二烷氧基丙酸酯的制备工艺 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2534212A (en) * | 1948-12-09 | 1950-12-19 | Harald Frederiksen | Process for producing muconic acid and its derivatives |
| US3429949A (en) * | 1966-07-14 | 1969-02-25 | Sun Oil Co | Unsaturated polyesters prepared from alpha,alpha'-dimethyl muconic acids |
-
1976
- 1976-01-22 ES ES444542A patent/ES444542A1/es not_active Expired
- 1976-01-22 US US05/651,263 patent/US4031136A/en not_active Expired - Lifetime
- 1976-01-23 BR BR7600410A patent/BR7600410A/pt unknown
- 1976-01-23 NL NL7600713A patent/NL7600713A/xx not_active Application Discontinuation
- 1976-01-26 SE SE7600765A patent/SE7600765L/xx unknown
- 1976-01-26 LU LU74242A patent/LU74242A1/xx unknown
- 1976-01-26 IT IT19605/76A patent/IT1054503B/it active
- 1976-01-27 DK DK31876*#A patent/DK31876A/da not_active Application Discontinuation
- 1976-01-27 CA CA244,301A patent/CA1045150A/en not_active Expired
- 1976-01-27 GB GB3074/76A patent/GB1528101A/en not_active Expired
- 1976-01-27 JP JP51007186A patent/JPS51100022A/ja active Pending
- 1976-01-28 FR FR7602250A patent/FR2299304A1/fr active Granted
- 1976-01-28 BE BE163865A patent/BE837990A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE837990A (fr) | 1976-07-28 |
| SE7600765L (sv) | 1976-07-29 |
| GB1528101A (en) | 1978-10-11 |
| JPS51100022A (enExample) | 1976-09-03 |
| ES444542A1 (es) | 1977-06-01 |
| DE2503313A1 (de) | 1976-07-29 |
| DK31876A (da) | 1976-07-29 |
| FR2299304B1 (enExample) | 1979-06-22 |
| AU1057576A (en) | 1977-08-04 |
| BR7600410A (pt) | 1976-08-31 |
| US4031136A (en) | 1977-06-21 |
| NL7600713A (nl) | 1976-07-30 |
| IT1054503B (it) | 1981-11-10 |
| LU74242A1 (enExample) | 1976-12-31 |
| FR2299304A1 (fr) | 1976-08-27 |
| DE2503313B2 (de) | 1976-12-02 |
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