DE2346021A1 - Verfahren zur herstellung von ,5hexandion - Google Patents
Verfahren zur herstellung von ,5hexandionInfo
- Publication number
- DE2346021A1 DE2346021A1 DE19732346021 DE2346021A DE2346021A1 DE 2346021 A1 DE2346021 A1 DE 2346021A1 DE 19732346021 DE19732346021 DE 19732346021 DE 2346021 A DE2346021 A DE 2346021A DE 2346021 A1 DE2346021 A1 DE 2346021A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- lactone
- hexanedione
- sulfate
- product
- 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 20
- 238000004519 manufacturing process Methods 0.000 title description 8
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 150000002596 lactones Chemical class 0.000 claims description 26
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims description 23
- 229910000359 iron(II) sulfate Inorganic materials 0.000 claims description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000003513 alkali Substances 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- 230000007062 hydrolysis Effects 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- -1 iron (II) sulfate Chemical class 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 230000015556 catabolic process Effects 0.000 claims description 3
- 238000006731 degradation reaction Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- JRHWHSJDIILJAT-UHFFFAOYSA-N 2-hydroxypentanoic acid Chemical compound CCCC(O)C(O)=O JRHWHSJDIILJAT-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 27
- MWVFCEVNXHTDNF-UHFFFAOYSA-N hexane-2,3-dione Chemical compound CCCC(=O)C(C)=O MWVFCEVNXHTDNF-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000011790 ferrous sulphate Substances 0.000 description 6
- 235000003891 ferrous sulphate Nutrition 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 238000003822 preparative gas chromatography Methods 0.000 description 3
- PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical compound CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 2
- BGCOWMUXKATLBU-UHFFFAOYSA-N 5-hydroxy-2,5-dimethyloxolane-2,4-dicarbonitrile Chemical compound C(#N)C1(OC(C(C1)C#N)(C)O)C BGCOWMUXKATLBU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
- OUYLXVQKVBXUGW-UHFFFAOYSA-N 2,3-dimethyl-1h-pyrrole Chemical compound CC=1C=CNC=1C OUYLXVQKVBXUGW-UHFFFAOYSA-N 0.000 description 1
- XGKHPDUUILTQAB-UHFFFAOYSA-N 2-cyano-2-hydroxypentanoic acid Chemical compound OC(C(=O)O)(CCC)C#N XGKHPDUUILTQAB-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- WUQQVFQGWWMQLD-UHFFFAOYSA-N 3,6-dioxoheptanoic acid Chemical compound CC(=O)CCC(=O)CC(O)=O WUQQVFQGWWMQLD-UHFFFAOYSA-N 0.000 description 1
- JKHBEWLCMFXCFW-UHFFFAOYSA-N 4,5-dimethyl-2,3-dihydrofuran Chemical compound CC1=C(C)OCC1 JKHBEWLCMFXCFW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 240000007930 Oxalis acetosella Species 0.000 description 1
- 235000008098 Oxalis acetosella Nutrition 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- UETZVSHORCDDTH-UHFFFAOYSA-N iron(2+);hexacyanide Chemical compound [Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] UETZVSHORCDDTH-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00289489A US3819714A (en) | 1972-09-15 | 1972-09-15 | Process for preparing 2,5-hexanedione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2346021A1 true DE2346021A1 (de) | 1974-03-21 |
Family
ID=23111758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732346021 Pending DE2346021A1 (de) | 1972-09-15 | 1973-09-12 | Verfahren zur herstellung von ,5hexandion |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3819714A (enExample) |
| JP (1) | JPS4962406A (enExample) |
| AU (1) | AU6022773A (enExample) |
| DE (1) | DE2346021A1 (enExample) |
| FR (1) | FR2200228B1 (enExample) |
| GB (1) | GB1394764A (enExample) |
| IT (1) | IT997554B (enExample) |
| ZA (1) | ZA737318B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4898988A (en) * | 1989-03-13 | 1990-02-06 | W. R. Grace & Co.-Conn. | Process for the preparation of β-hydroxyketones |
| JP2647717B2 (ja) * | 1989-06-06 | 1997-08-27 | 宇部興産株式会社 | α―（ω―シアノアルカノイル）―γ―ブチロラクトンおよびその製法 |
| WO2013040514A1 (en) | 2011-09-16 | 2013-03-21 | Micromidas Inc. | Methods of producing para-xylene and terephthalic acid |
| US8889938B2 (en) | 2012-03-15 | 2014-11-18 | Micromidas, Inc. | Methods of producing para-xylene |
| US10392317B2 (en) | 2012-09-14 | 2019-08-27 | Micromidas, Inc. | Methods of producing para-xylene and terephthalic acid |
-
1972
- 1972-09-15 US US00289489A patent/US3819714A/en not_active Expired - Lifetime
-
1973
- 1973-09-12 DE DE19732346021 patent/DE2346021A1/de active Pending
- 1973-09-12 AU AU60227/73A patent/AU6022773A/en not_active Expired
- 1973-09-13 JP JP48102705A patent/JPS4962406A/ja active Pending
- 1973-09-14 GB GB4331473A patent/GB1394764A/en not_active Expired
- 1973-09-14 IT IT52531/73A patent/IT997554B/it active
- 1973-09-14 FR FR7333051A patent/FR2200228B1/fr not_active Expired
- 1973-09-14 ZA ZA737318A patent/ZA737318B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1394764A (en) | 1975-05-21 |
| FR2200228A1 (enExample) | 1974-04-19 |
| FR2200228B1 (enExample) | 1977-08-05 |
| JPS4962406A (enExample) | 1974-06-17 |
| US3819714A (en) | 1974-06-25 |
| IT997554B (it) | 1975-12-30 |
| AU6022773A (en) | 1975-03-13 |
| ZA737318B (en) | 1974-11-27 |
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