WO2004106313A1 - Procede pour la fabrication d'un compose organique comprenant au moins un groupement fonctionnel oxygene - Google Patents
Procede pour la fabrication d'un compose organique comprenant au moins un groupement fonctionnel oxygene Download PDFInfo
- Publication number
- WO2004106313A1 WO2004106313A1 PCT/EP2004/050990 EP2004050990W WO2004106313A1 WO 2004106313 A1 WO2004106313 A1 WO 2004106313A1 EP 2004050990 W EP2004050990 W EP 2004050990W WO 2004106313 A1 WO2004106313 A1 WO 2004106313A1
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- WO
- WIPO (PCT)
- Prior art keywords
- process according
- reaction
- carried out
- oxidizable
- imidoaromatic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 36
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 8
- 125000000524 functional group Chemical group 0.000 title claims abstract description 7
- 239000002243 precursor Substances 0.000 claims abstract description 20
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000012429 reaction media Substances 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 150000003998 acyclic ketones Chemical group 0.000 claims description 4
- 150000003997 cyclic ketones Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000004437 phosphorous atom Chemical group 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- UZJGVXSQDRSSHU-UHFFFAOYSA-N 6-(1,3-dioxoisoindol-2-yl)hexaneperoxoic acid Chemical compound C1=CC=C2C(=O)N(CCCCCC(=O)OO)C(=O)C2=C1 UZJGVXSQDRSSHU-UHFFFAOYSA-N 0.000 claims description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 230000000750 progressive effect Effects 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- -1 acyclic olefin Chemical class 0.000 description 7
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- HTIRHQRTDBPHNZ-UHFFFAOYSA-N Dibutyl sulfide Chemical compound CCCCSCCCC HTIRHQRTDBPHNZ-UHFFFAOYSA-N 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- AIDFJGKWTOULTC-UHFFFAOYSA-N 1-butylsulfonylbutane Chemical compound CCCCS(=O)(=O)CCCC AIDFJGKWTOULTC-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- FHUDAMLDXFJHJE-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-one Chemical compound CC(=O)C(F)(F)F FHUDAMLDXFJHJE-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- LSQARZALBDFYQZ-UHFFFAOYSA-N 4,4'-difluorobenzophenone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 LSQARZALBDFYQZ-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004832 aryl thioethers Chemical class 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 description 1
- CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- OOXWYYGXTJLWHA-UHFFFAOYSA-N cyclopropene Chemical compound C1C=C1 OOXWYYGXTJLWHA-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- SNHMUERNLJLMHN-IDEBNGHGSA-N iodobenzene Chemical group I[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 SNHMUERNLJLMHN-IDEBNGHGSA-N 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N methyl mercaptane Natural products SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propyl mercaptan Natural products CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003450 sulfenic acids Chemical class 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
Definitions
- the invention therefore relates to a process for the manufacture of an organic compound comprising at least one oxygenated functional group, according to which an organic precursor comprising an oxidizable functionality is subjected to a reaction with an idoarornatic percarboxylic acid.
- the imidoarornatic percarboxylic acid often corresponds to the formula
- the reaction is generally carried out at a temperature of at least -100 ° C. Often this temperature is at least 0 ° C. Preferably, it is at least 20 ° C. In the process according to the invention, the reaction is generally carried out at a temperature of at most 150 ° C.
- this temperature is at most 80 ° C. Preferably, it is at most 60 ° C.
- the reaction is generally carried out at a pressure of at least 0.5 bar. Preferably, this pressure is greater than or equal to about 1 bar (atmospheric pressure). In the process according to the invention, the reaction is generally carried out at a pressure of at most 100 bar. Often this pressure is at most 25 bar. Preferably, it is at most 15 bar.
- the reaction is generally carried out in a reaction medium having a content of imidoarornatic percarboxylic acid of at least 0.1% by weight relative to the total weight of the reaction medium. Often this content is at least 5%. Preferably, it is at least 7%. In the process according to the invention, this content is generally at most 90%. Often this content is at most 80%. Preferably, it is at most 70%.
- the reaction is generally carried out in a reaction medium having an organic precursor content of at least 1% by weight relative to the total weight of the reaction medium. Often this content is at least 10%. Preferably, it is at least 30%. In the process according to the invention, this content is generally at most 80%. Often this content is at most 75%. Preferably it is at most 70%.
- the process according to the invention can be carried out in the presence of an organic solvent, preferably a polar organic solvent such as for example dioxane or tetrahydrofuran.
- the process according to the invention can also be carried out in the absence of solvent, the imidoarornatic percarboxylic acid being generally soluble in the organic precursor. This allows the reaction to be carried out with a lower volume of reaction medium and a high volume productivity.
- a progressive addition of the imidoaromatic percarboxylic acid is carried out to the reaction medium.
- a continuous addition of the imidoaromatic percarboxylic acid is carried out to the reaction medium.
- the imidoaromatic percarboxylic acid can be introduced into the reaction, for example in the form of a solution in an organic solvent or in pure form.
- the reaction is generally carried out for a period of at least 10 min. Often this duration is at least 30 min. Preferably, it is at least 1 hour.
- the reaction is generally carried out for a period of at most 50 hours. Often, this duration is at most 20 hours. Preferably, it is at most 10 h. A duration of at most 5 hours is more particularly preferred. It has been found that imidoaromatic percarboxylic acid is capable of reacting quickly with the precursor.
- the reaction is carried out in the substantial absence of water.
- the reaction is generally carried out in a reaction medium having a water content of at most 10% by weight relative to the total weight of the reaction medium. Often this content is at most 5%. Preferably, it is at most 1%.
- a reaction medium having a water content of greater than or equal to about 100 mg / kg gives good results.
- the oxygenated compound can be separated from the reaction medium by techniques known per se, such as distillation or crystallization.
- the imidoaromatic carboxylic acid by-product of the reaction can optionally be removed from the reaction medium, for example, by aqueous extraction.
- the organic precursor is often chosen from cyclic or acyclic olefins substituted or not, cyclic or acyclic ketones substituted or not, compounds containing at least one oxidizable sulfur atom, compounds containing at least one oxidizable selenium atom, compounds containing at least one nitrogen atom oxidizable, compounds containing at least one oxidizable phosphorus atom and compounds containing at least one oxidizable iodine atom.
- the organic precursor is an oxidizable fluorinated compound.
- the organic precursor is an acyclic olefin
- it generally comprises from 2 to 100, preferably from 2 to 20 carbon atoms. Often, it includes a double bond in position 1 or 2. Preferably, it comprises a double bond in position 1 (terminal).
- acyclic olefins are ethylene, propylene, 1-butene, 2-butene and their substituted derivatives such as allyl chloride, allyl alcohol, vinyl choride, vinylidene chloride, vinyl fluoride, vinylidene fluoride and hexafluoropropylene.
- the organic precursor when it is a cyclic olefin, it generally comprises from 3 to 100, preferably from 4 to 20 carbon atoms. Often, it comprises a cycle comprising from 4 to 8, preferably from 5, 6 or 7 atoms.
- the cycle can be a carbocycle or a heterocycle.
- Specific examples of cyclic olefins are cyclopropene, cyclobutene, cyclopentene, cyclohexene, norbornene, dicyclopentadiene, ⁇ -pinene, and their substituted derivatives.
- the organic precursor when it is an acyclic ketone, it generally comprises from 3 to 100, preferably from 3 to 20 carbon atoms.
- acyclic ketones are acetone, butanone, pentanone, hexanone and their substituted derivatives such as for example trifluoroacetone, hexafluoroacetone or 4,4'difluorobenzophenone.
- the organic precursor when it is a cyclic ketone, it generally comprises from 4 to 100, preferably from 4 to 20 carbon atoms.
- cyclic ketones are cyclobutanone, cyclopentanone, cyclohexanone, cycloheptanone and their substituted derivatives.
- the organic precursor is chosen from compounds containing at least one oxidizable sulfur atom, it is often chosen from symmetrical or asymmetrical thioethers and mercaptatis, in particular alkyl or aryl thioethers and mercaptans, generally comprising 1 to 100, preferably from 1 to 20 carbon atoms.
- specific examples are methyl, ethyl, propyl or n-butyl mercaptan, among dimethyl, diethyl, dipropyl or di n-butyl sulfide, among methyl ethyl or methyl sulfide.
- the method according to the invention provides access to a variety of organic compounds containing sulfur, which can optionally also serve as an organic precursor, such as, for example, disulfides, sulfenic or sulfinic acids, and disulfoxides.
- organic precursor such as, for example, disulfides, sulfenic or sulfinic acids, and disulfoxides.
- the organic precursor is chosen from compounds containing at least one oxidizable nitrogen atom, it is often chosen from amines, in particular alkyl- or arylamines and imines, generally comprising from 1 to 100, preferably from 1 to 20 carbon atoms.
- Primary, secondary or tertiary amines can be used.
- the organic precursor is chosen from compounds containing at least one oxidizable phosphorus atom, it is often chosen from phosphines, in particular alkyl- or arylphosphines, phosphine oxides and phosphonates, generally comprising from 3 to 100, from preferably from 3 to 20 carbon atoms and their substituted derivatives.
- phosphines in particular alkyl- or arylphosphines, phosphine oxides and phosphonates, generally comprising from 3 to 100, from preferably from 3 to 20 carbon atoms and their substituted derivatives.
- phosphines in particular alkyl- or arylphosphines, phosphine oxides and phosphonates, generally comprising from 3 to 100, from preferably from 3 to 20 carbon atoms and their substituted derivatives.
- Specific examples are trialkylphosphines and triarylphosphines
- Example 1 A solution of peracid was previously prepared by dissolving 277 g of PAP in 700 ml of dioxane contained in a one-liter volumetric flask.
- Example 3 By following procedures analogous to Example 1 but replacing dioxane by tetiahydrofuran, glycidol was obtained from allyl alcohol. The glycidol was hydrolyzed to glycerin in the presence of sulfuric acid.
- Example 3
- the synthesis was carried out in a 25 cm 3 flask heated to 60 ° C by means of an oil bath and surmounted by a condenser cooled to -10 ° C by circulation of a water / ethylene glycol mixture. No agitation system was used.
- the synthesis of dibutylsulfone by oxidation of dibutyl sulfide was carried out in the presence of PAP dissolved in dioxane (see Example 1).
- the synthesis was carried out in a three-necked 100 cm flask maintained at 20 ° C. by immersion in a thermostatically controlled water bath.
- the flask was surmounted by a condenser cooled to -10 ° C by circulation of a water / ethylene glycol mixture.
- a CaCl 2 cartridge was located at the outlet of the condenser to avoid humidity entry.
- the reaction medium was homogenized by magnetic stirring.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Pyrane Compounds (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/558,771 US20070037990A1 (en) | 2003-06-03 | 2004-06-02 | Method of producing an organic compound comprising at least one oxygenated functional group |
EP04741703A EP1636202A1 (fr) | 2003-06-03 | 2004-06-02 | Procede pour la fabrication d un compose organique comprenan t au moins un groupement fonctionnel oxygene |
JP2006508312A JP2006526593A (ja) | 2003-06-03 | 2004-06-02 | 少なくとも1つの含酸素官能基を含む有機化合物を製造する方法 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0306718A FR2855824A1 (fr) | 2003-06-03 | 2003-06-03 | Procede pour la fabrication d'un compose organique comprenant au moins un groupement fonctionnel oxygene |
FR03.06718 | 2003-06-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2004106313A1 true WO2004106313A1 (fr) | 2004-12-09 |
Family
ID=33443125
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2004/050990 WO2004106313A1 (fr) | 2003-06-03 | 2004-06-02 | Procede pour la fabrication d'un compose organique comprenant au moins un groupement fonctionnel oxygene |
Country Status (6)
Country | Link |
---|---|
US (1) | US20070037990A1 (fr) |
EP (1) | EP1636202A1 (fr) |
JP (1) | JP2006526593A (fr) |
CN (1) | CN1802365A (fr) |
FR (1) | FR2855824A1 (fr) |
WO (1) | WO2004106313A1 (fr) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0325288A1 (fr) * | 1988-01-20 | 1989-07-26 | AUSIMONT S.p.A. | Acides percarboxyliques imido-aromatiques |
DE3906768A1 (de) * | 1989-03-03 | 1990-09-06 | Henkel Kgaa | Peroxycarbonsaeuren und deren verwendung |
WO1998027943A1 (fr) * | 1996-12-23 | 1998-07-02 | The Procter & Gamble Company | Compositions pour colorants capillaires |
GB2330358A (en) * | 1997-10-15 | 1999-04-21 | Contract Chemicals Limited | Epoxidation of Alkenes |
WO2000051651A1 (fr) * | 1999-03-05 | 2000-09-08 | The Procter & Gamble Company | Articles absorbants dotes d'un systeme d'elimination des odeurs |
WO2000065083A2 (fr) * | 1999-04-26 | 2000-11-02 | The Procter & Gamble Company | Protections periodiques feminines jetables pourvues d'un moyen de detection du sang, en tant que capteur |
-
2003
- 2003-06-03 FR FR0306718A patent/FR2855824A1/fr active Pending
-
2004
- 2004-06-02 CN CN200480015669.2A patent/CN1802365A/zh active Pending
- 2004-06-02 WO PCT/EP2004/050990 patent/WO2004106313A1/fr not_active Application Discontinuation
- 2004-06-02 EP EP04741703A patent/EP1636202A1/fr not_active Withdrawn
- 2004-06-02 US US10/558,771 patent/US20070037990A1/en not_active Abandoned
- 2004-06-02 JP JP2006508312A patent/JP2006526593A/ja active Pending
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0325288A1 (fr) * | 1988-01-20 | 1989-07-26 | AUSIMONT S.p.A. | Acides percarboxyliques imido-aromatiques |
DE3906768A1 (de) * | 1989-03-03 | 1990-09-06 | Henkel Kgaa | Peroxycarbonsaeuren und deren verwendung |
WO1998027943A1 (fr) * | 1996-12-23 | 1998-07-02 | The Procter & Gamble Company | Compositions pour colorants capillaires |
GB2330358A (en) * | 1997-10-15 | 1999-04-21 | Contract Chemicals Limited | Epoxidation of Alkenes |
WO2000051651A1 (fr) * | 1999-03-05 | 2000-09-08 | The Procter & Gamble Company | Articles absorbants dotes d'un systeme d'elimination des odeurs |
WO2000065083A2 (fr) * | 1999-04-26 | 2000-11-02 | The Procter & Gamble Company | Protections periodiques feminines jetables pourvues d'un moyen de detection du sang, en tant que capteur |
Non-Patent Citations (1)
Title |
---|
LION, CLAUDE ET AL: "A fast, mild and complete destruction of chemical pollutants is a significant criterion in chemical decontamination", COMPTES RENDUS DE L'ACADEMIE DES SCIENCES, SERIE IIC: CHIMIE, vol. 2, no. 1, 1999, pages 57 - 62, XP002271000 * |
Also Published As
Publication number | Publication date |
---|---|
CN1802365A (zh) | 2006-07-12 |
JP2006526593A (ja) | 2006-11-24 |
FR2855824A1 (fr) | 2004-12-10 |
US20070037990A1 (en) | 2007-02-15 |
EP1636202A1 (fr) | 2006-03-22 |
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