DE2207699A1 - - Google Patents
Info
- Publication number
- DE2207699A1 DE2207699A1 DE19722207699 DE2207699A DE2207699A1 DE 2207699 A1 DE2207699 A1 DE 2207699A1 DE 19722207699 DE19722207699 DE 19722207699 DE 2207699 A DE2207699 A DE 2207699A DE 2207699 A1 DE2207699 A1 DE 2207699A1
- Authority
- DE
- Germany
- Prior art keywords
- rearrangement
- acid
- anhydride
- carried out
- ozonide
- 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.)
- Granted
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 39
- 230000008707 rearrangement Effects 0.000 claims description 38
- WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000002798 polar solvent Substances 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 235000011054 acetic acid Nutrition 0.000 claims description 14
- 150000001336 alkenes Chemical class 0.000 claims description 14
- 150000008064 anhydrides Chemical class 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 150000002978 peroxides Chemical class 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 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 claims description 7
- -1 alkali metal salt Chemical class 0.000 claims description 7
- 239000011261 inert gas Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 150000007530 organic bases Chemical class 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000001632 sodium acetate Substances 0.000 claims description 7
- 235000017281 sodium acetate Nutrition 0.000 claims description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 150000001925 cycloalkenes Chemical class 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 6
- 230000001588 bifunctional effect Effects 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- 235000011056 potassium acetate Nutrition 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- BWILYWWHXDGKQA-UHFFFAOYSA-M potassium propanoate Chemical compound [K+].CCC([O-])=O BWILYWWHXDGKQA-UHFFFAOYSA-M 0.000 claims description 2
- 239000004331 potassium propionate Substances 0.000 claims description 2
- 235000010332 potassium propionate Nutrition 0.000 claims description 2
- 229940114930 potassium stearate Drugs 0.000 claims description 2
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 235000015424 sodium Nutrition 0.000 claims 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 2
- 239000002585 base Substances 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- XKPJKVVZOOEMPK-UHFFFAOYSA-M lithium;formate Chemical compound [Li+].[O-]C=O XKPJKVVZOOEMPK-UHFFFAOYSA-M 0.000 claims 1
- 235000007686 potassium Nutrition 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000004324 sodium propionate Substances 0.000 claims 1
- 235000010334 sodium propionate Nutrition 0.000 claims 1
- 239000000243 solution Substances 0.000 description 39
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 19
- 150000001299 aldehydes Chemical class 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 229960000583 acetic acid Drugs 0.000 description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 16
- 239000001301 oxygen Substances 0.000 description 16
- 229910052760 oxygen Inorganic materials 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000006385 ozonation reaction Methods 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- HYPABJGVBDSCIT-UPHRSURJSA-N cyclododecene Chemical compound C1CCCCC\C=C/CCCC1 HYPABJGVBDSCIT-UPHRSURJSA-N 0.000 description 10
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 8
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- KGEACANGAYABKT-UHFFFAOYSA-N 12-oxododecanoic acid Chemical compound OC(=O)CCCCCCCCCCC=O KGEACANGAYABKT-UHFFFAOYSA-N 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- PNPPVRALIYXJBW-UHFFFAOYSA-N 6-oxohexanoic acid Chemical compound OC(=O)CCCCC=O PNPPVRALIYXJBW-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000012454 non-polar solvent Substances 0.000 description 3
- 238000005949 ozonolysis reaction Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000006268 reductive amination reaction Methods 0.000 description 3
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N 12-hydroxylauric acid Chemical compound OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- ADCQBLMDYBHFGK-UHFFFAOYSA-N acetyl octanoate Chemical compound CCCCCCCC(=O)OC(C)=O ADCQBLMDYBHFGK-UHFFFAOYSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 2
- 239000004913 cyclooctene Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000009533 lab test Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- IDTWXYWXRFEWNM-UHFFFAOYSA-N 13-oxotrideca-2,4-dienoic acid Chemical compound OC(=O)C=CC=CCCCCCCCC=O IDTWXYWXRFEWNM-UHFFFAOYSA-N 0.000 description 1
- UEXYJHLCLUYOFA-UHFFFAOYSA-N 8-oxooctanoic acid Chemical compound OC(=O)CCCCCCC=O UEXYJHLCLUYOFA-UHFFFAOYSA-N 0.000 description 1
- 229920001744 Polyaldehyde Polymers 0.000 description 1
- 229910020175 SiOH Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- LZLOFGMGFADIKQ-UHFFFAOYSA-N benzene;1,4-dioxane Chemical compound C1COCCO1.C1=CC=CC=C1 LZLOFGMGFADIKQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- OOYGSFOGFJDDHP-KMCOLRRFSA-N kanamycin A sulfate Chemical group OS(O)(=O)=O.O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N OOYGSFOGFJDDHP-KMCOLRRFSA-N 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011268 retreatment Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D323/00—Heterocyclic compounds containing more than two oxygen atoms as the only ring hetero atoms
- C07D323/02—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
-
- 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
- C07C45/40—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with ozone; by ozonolysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/34—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with ozone; by hydrolysis of ozonides
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)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2080271 | 1971-02-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2207699A1 true DE2207699A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-08-24 |
| DE2207699B2 DE2207699B2 (de) | 1977-09-22 |
| DE2207699C3 DE2207699C3 (de) | 1978-05-24 |
Family
ID=11172271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2207699A Expired DE2207699C3 (de) | 1971-02-19 | 1972-02-18 | Verfahren zur Herstellung von Säurealdehyden durch Umlagerung der aus den entsprechenden Ozoniden von Cycloolefinen gebildeten Peroxidderivate |
Country Status (7)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5434307A (en) * | 1993-05-21 | 1995-07-18 | Howard University | Synthesis of 12-oxododecanoic acid oxime from vernolic acid |
| WO2011160730A1 (de) | 2010-06-25 | 2011-12-29 | Evonik Degussa Gmbh | Synthese von omega-aminocarbonsäuren und deren estern aus ungesättigten fettsäurederivaten |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3979450A (en) * | 1973-02-08 | 1976-09-07 | Jury Leonidovich Moskovich | Method for preparing dicarboxylic acids |
| IT998227B (it) * | 1973-07-11 | 1976-01-20 | Snia Viscosa | Metodo per la produzione di com posti polifunzionali lineari insa turi relativi prodotti industriali insaturi e loro derivati insaturi o saturi |
| US4164508A (en) * | 1973-07-11 | 1979-08-14 | Snia Viscosa Societa' Nazionale Industria Viscosa S.p.A. | Formyl alkenoic acids |
| US4218384A (en) * | 1973-07-11 | 1980-08-19 | Snia Viscosa Societa Nazionale Industria Applicazioni Viscosa S.P.A. | Omega-amino alkenoic acids |
| US4192813A (en) * | 1973-07-11 | 1980-03-11 | Snia Viscoas Societa Nazionale Industria Applicazioni Viscosa S.p.A. | Omega-hydroxy alkenoic acid |
| IT1075949B (it) * | 1976-12-29 | 1985-04-22 | Snia Viscosa | Procedimento di preparazione di dialdeidi sature e insature |
| IT1125446B (it) * | 1979-10-05 | 1986-05-14 | Snia Viscosa | Preparazione di alfa beta-dialdeidi e di alfa beta-diacidi insaturi o saturi |
| US4612391A (en) * | 1980-09-22 | 1986-09-16 | Philip Morris Incorporated | Preparation of oxycarboxylic acids |
| FR2528179B1 (fr) * | 1982-06-03 | 1985-06-28 | Gilson Med Electr | Procede et dispositif d'analyse d'effluents pour detection de pics |
| JPS609753A (ja) * | 1983-06-30 | 1985-01-18 | Canon Inc | インク製造装置 |
| JPS609749A (ja) * | 1983-06-30 | 1985-01-18 | Canon Inc | インク製造装置 |
| JPS59199770A (ja) * | 1983-04-27 | 1984-11-12 | Canon Inc | 染料精製装置 |
| JPS59199768A (ja) * | 1983-04-27 | 1984-11-12 | Canon Inc | 染料精製装置 |
| JPS59199765A (ja) * | 1983-04-27 | 1984-11-12 | Canon Inc | 染料精製装置 |
| JPS59199769A (ja) * | 1983-04-27 | 1984-11-12 | Canon Inc | 染料精製装置 |
| JPS609750A (ja) * | 1983-06-30 | 1985-01-18 | Canon Inc | インク製造装置 |
| JPS59199766A (ja) * | 1983-04-27 | 1984-11-12 | Canon Inc | 染料精製装置 |
| JPS609752A (ja) * | 1983-06-30 | 1985-01-18 | Canon Inc | インク製造装置 |
| JPS59199767A (ja) * | 1983-04-27 | 1984-11-12 | Canon Inc | 染料精製装置 |
| JPS609751A (ja) * | 1983-06-30 | 1985-01-18 | Canon Inc | インク製造装置 |
| AT380008B (de) * | 1983-12-23 | 1986-03-25 | Chemie Linz Ag | Verfahren zur herstellung von mono- oder biscarbonylverbindungen |
| JPH0830026B2 (ja) * | 1987-05-27 | 1996-03-27 | 三井東圧化学株式会社 | グリオキシル酸類の製造法 |
| DE3722566A1 (de) * | 1987-07-08 | 1989-01-19 | Henkel Kgaa | Verfahren zur kontinuierlichen ozonisierung von ungesaettigten organischen verbindungen |
| WO1993002991A1 (en) * | 1991-08-06 | 1993-02-18 | Lion Corporation | Process for ozonizing unsaturated fatty acid or lower alkyl ester thereof and oxidative decomposition of the resulting ozonide |
| JP3062584B2 (ja) * | 1991-09-09 | 2000-07-10 | ヘンケル・コーポレーション | 触媒作用を及ぼした、不飽和化合物のオゾニドを酸化してカルボン酸を生成する方法 |
| US6423853B1 (en) * | 2001-09-24 | 2002-07-23 | E. I. Du Pont De Nemours & Comp. | Continuous ozonolysis of cycloalkenes into ozonides |
| US8895667B2 (en) | 2009-07-17 | 2014-11-25 | Tyco Electronics Corporation | Methods of making reversible crosslinked polymers and related methods |
| WO2015006360A1 (en) | 2013-07-11 | 2015-01-15 | Invista Technologies S.À R.L. | Acyclic alkenes via ozonolysis of multi-unsaturated cycloalkenes |
| CA3114469A1 (en) * | 2018-10-19 | 2020-04-23 | P2 Science, Inc. | New methods for disproportionation quenching of ozonides |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2819279A (en) * | 1950-07-22 | 1958-01-07 | Standard Oil Co | Ozonization of olefinic compounds to a carboxylic acid and an aldehyde |
| US2891988A (en) * | 1957-08-19 | 1959-06-23 | American Cyanamid Co | 5-formyl-2-oxovaleric acid, its salts and esters and a process of producing the same |
| FR1210132A (fr) * | 1957-09-09 | 1960-03-07 | Koppers Co Inc | Perfectionnements apportés aux procédés d'oxydation de mélanges d'anthracène etde phénanthrène |
| US3362971A (en) * | 1964-10-01 | 1968-01-09 | Ethyl Corp | Ozonolysis of olefins in an alkoxy-alkanol solvent |
| US3383398A (en) * | 1967-07-26 | 1968-05-14 | Union Carbide Corp | Production of carboxylic acids in the presence of pyridine |
| CH493452A (de) * | 1967-09-15 | 1970-07-15 | Givaudan & Cie Sa | Verfahren zur Herstellung von Terpenderivaten |
| US3481954A (en) * | 1968-09-18 | 1969-12-02 | Monsanto Co | Ozonolysis products of hexachlorodicyclopentadiene |
| US3691233A (en) * | 1971-01-13 | 1972-09-12 | Gulf Research Development Co | Process for producing organic acids |
-
1971
- 1971-04-16 NL NLAANVRAGE7105147,A patent/NL171808C/xx not_active IP Right Cessation
-
1972
- 1972-02-17 US US00227268A patent/US3856833A/en not_active Expired - Lifetime
- 1972-02-17 US US227203A patent/US3868392A/en not_active Expired - Lifetime
- 1972-02-18 JP JP1661472A patent/JPS5441561B1/ja active Pending
- 1972-02-18 JP JP1661372A patent/JPS5323289B1/ja active Pending
- 1972-02-18 FR FR7205594A patent/FR2125605B1/fr not_active Expired
- 1972-02-18 GB GB772072A patent/GB1378351A/en not_active Expired
- 1972-02-18 BE BE779545A patent/BE779545A/xx unknown
- 1972-02-18 DE DE2207699A patent/DE2207699C3/de not_active Expired
- 1972-02-18 FR FR7205593A patent/FR2125604B1/fr not_active Expired
- 1972-02-18 GB GB771972A patent/GB1382349A/en not_active Expired
- 1972-02-18 BE BE779544A patent/BE779544A/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5434307A (en) * | 1993-05-21 | 1995-07-18 | Howard University | Synthesis of 12-oxododecanoic acid oxime from vernolic acid |
| US5530148A (en) * | 1993-05-21 | 1996-06-25 | Howard University | Synthesis of 12-aminododecanoic acid |
| WO2011160730A1 (de) | 2010-06-25 | 2011-12-29 | Evonik Degussa Gmbh | Synthese von omega-aminocarbonsäuren und deren estern aus ungesättigten fettsäurederivaten |
| DE102010026196A1 (de) | 2010-06-25 | 2011-12-29 | Evonik Degussa Gmbh | Synthese von omega-Aminocarbonsäuren und deren Estern aus ungesättigten Fettsäurederivaten |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2207700A1 (de) | 1972-11-23 |
| BE779544A (fr) | 1972-08-16 |
| JPS5441561B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-12-08 |
| BE779545A (fr) | 1972-08-18 |
| FR2125605A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-09-29 |
| GB1382349A (en) | 1975-01-29 |
| GB1378351A (en) | 1974-12-27 |
| NL7105147A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-08-22 |
| DE2207699C3 (de) | 1978-05-24 |
| US3856833A (en) | 1974-12-24 |
| US3868392A (en) | 1975-02-25 |
| NL171808B (nl) | 1982-12-16 |
| JPS5323289B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-07-13 |
| FR2125605B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-09-02 |
| FR2125604A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-09-29 |
| DE2207699B2 (de) | 1977-09-22 |
| NL171808C (nl) | 1983-05-16 |
| FR2125604B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-12-23 |
| DE2207700B2 (de) | 1976-10-21 |
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