DE2337813C3 - Verfahren zur Herstellung von Monoacetalen aromatischer 1,2-Diketone - Google Patents
Verfahren zur Herstellung von Monoacetalen aromatischer 1,2-DiketoneInfo
- Publication number
- DE2337813C3 DE2337813C3 DE2337813A DE2337813A DE2337813C3 DE 2337813 C3 DE2337813 C3 DE 2337813C3 DE 2337813 A DE2337813 A DE 2337813A DE 2337813 A DE2337813 A DE 2337813A DE 2337813 C3 DE2337813 C3 DE 2337813C3
- Authority
- DE
- Germany
- Prior art keywords
- benzil
- thionyl chloride
- aromatic
- acetal
- monoacetals
- 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
- 238000000034 method Methods 0.000 title claims description 22
- 125000003118 aryl group Chemical group 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 40
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 claims description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 244000028419 Styrax benzoin Species 0.000 claims description 14
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 14
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 14
- 235000019382 gum benzoic Nutrition 0.000 claims description 14
- 229960002130 benzoin Drugs 0.000 claims description 9
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 3
- 125000005594 diketone group Chemical group 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 238000001816 cooling Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 8
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000001241 acetals Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- -1 benzoin acetal Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- BDUPRNVPXOHWIL-UHFFFAOYSA-N dimethyl sulfite Chemical compound COS(=O)OC BDUPRNVPXOHWIL-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 229960005323 phenoxyethanol Drugs 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- 238000006359 acetalization reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- OTPHIMSEPGVYHC-UHFFFAOYSA-N 1,2-bis(2,4-dimethylphenyl)-2-hydroxyethanone Chemical compound CC1=CC(C)=CC=C1C(O)C(=O)C1=CC=C(C)C=C1C OTPHIMSEPGVYHC-UHFFFAOYSA-N 0.000 description 1
- ZKERBBAYDZRNID-UHFFFAOYSA-N 1,2-bis(2,4-dimethylphenyl)ethane-1,2-dione Chemical compound CC1=CC(C)=CC=C1C(=O)C(=O)C1=CC=C(C)C=C1C ZKERBBAYDZRNID-UHFFFAOYSA-N 0.000 description 1
- QGVJJXJRGYQAST-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)ethane-1,2-dione Chemical compound CC1=CC=CC=C1C(=O)C(=O)C1=CC=CC=C1C QGVJJXJRGYQAST-UHFFFAOYSA-N 0.000 description 1
- KOVLYVFCYREWLS-UHFFFAOYSA-N 1,2-bis(3-bromophenyl)-2-hydroxyethanone Chemical compound C=1C=CC(Br)=CC=1C(O)C(=O)C1=CC=CC(Br)=C1 KOVLYVFCYREWLS-UHFFFAOYSA-N 0.000 description 1
- UCXPESOPEKJXJR-UHFFFAOYSA-N 1,2-bis(4-chlorophenyl)-2-hydroxyethanone Chemical compound C=1C=C(Cl)C=CC=1C(O)C(=O)C1=CC=C(Cl)C=C1 UCXPESOPEKJXJR-UHFFFAOYSA-N 0.000 description 1
- XMAWUPHYEABFDR-UHFFFAOYSA-N 1,2-bis(4-chlorophenyl)ethane-1,2-dione Chemical compound C1=CC(Cl)=CC=C1C(=O)C(=O)C1=CC=C(Cl)C=C1 XMAWUPHYEABFDR-UHFFFAOYSA-N 0.000 description 1
- BCWCEHMHCDCJAD-UHFFFAOYSA-N 1,2-bis(4-methylphenyl)ethane-1,2-dione Chemical compound C1=CC(C)=CC=C1C(=O)C(=O)C1=CC=C(C)C=C1 BCWCEHMHCDCJAD-UHFFFAOYSA-N 0.000 description 1
- LVSZQGATCLRLCP-UHFFFAOYSA-N 1,2-bis(4-propan-2-ylphenyl)ethane-1,2-dione Chemical compound C1=CC(C(C)C)=CC=C1C(=O)C(=O)C1=CC=C(C(C)C)C=C1 LVSZQGATCLRLCP-UHFFFAOYSA-N 0.000 description 1
- VIFFKTKUPYOXJM-UHFFFAOYSA-N 1,2-diphenyl-2,2-dipropoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)(OCCC)C(=O)C1=CC=CC=C1 VIFFKTKUPYOXJM-UHFFFAOYSA-N 0.000 description 1
- ZBYYVDATVABBCF-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-(4-methylphenyl)ethane-1,2-dione Chemical compound C1=CC(C)=CC=C1C(=O)C(=O)C1=CC=C(Cl)C=C1Cl ZBYYVDATVABBCF-UHFFFAOYSA-N 0.000 description 1
- OJSVMWSVJDRPNZ-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-hydroxy-2-(4-methylphenyl)ethanone Chemical compound C1=CC(C)=CC=C1C(O)C(=O)C1=CC=C(Cl)C=C1Cl OJSVMWSVJDRPNZ-UHFFFAOYSA-N 0.000 description 1
- BHVXATXMHZWDFK-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(4-phenylphenyl)ethane-1,2-dione Chemical compound C1=CC(Cl)=CC=C1C(=O)C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 BHVXATXMHZWDFK-UHFFFAOYSA-N 0.000 description 1
- HCYLAXXZSZZQKD-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-hydroxy-2-(4-phenylphenyl)ethanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(O)C(=O)C1=CC=C(Cl)C=C1 HCYLAXXZSZZQKD-UHFFFAOYSA-N 0.000 description 1
- FPUIVHKZDVPMBS-UHFFFAOYSA-N 1-[4,4-di(propan-2-yl)cyclohexa-1,5-dien-1-yl]-2-hydroxy-2-phenylethanone Chemical compound C1=CC(C(C)C)(C(C)C)CC=C1C(=O)C(O)C1=CC=CC=C1 FPUIVHKZDVPMBS-UHFFFAOYSA-N 0.000 description 1
- IMHIDILLANKTRJ-UHFFFAOYSA-N 1-phenyl-2-(2,4,6-trimethylphenyl)ethane-1,2-dione Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C(=O)C1=CC=CC=C1 IMHIDILLANKTRJ-UHFFFAOYSA-N 0.000 description 1
- YBHCENFWWFXYNH-UHFFFAOYSA-N 2,2-bis(2-butoxyethoxy)-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCOCCCC)(OCCOCCCC)C(=O)C1=CC=CC=C1 YBHCENFWWFXYNH-UHFFFAOYSA-N 0.000 description 1
- IOCJGSZCXNYSGN-UHFFFAOYSA-N 2,2-dibutoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)(OCCCC)C(=O)C1=CC=CC=C1 IOCJGSZCXNYSGN-UHFFFAOYSA-N 0.000 description 1
- GIMQKKFOOYOQGB-UHFFFAOYSA-N 2,2-diethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)(OCC)C(=O)C1=CC=CC=C1 GIMQKKFOOYOQGB-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- CKZXADVHFFKWKQ-UHFFFAOYSA-N 2-hydroxy-1,2-bis(2-methoxyphenyl)ethanone Chemical compound COC1=CC=CC=C1C(O)C(=O)C1=CC=CC=C1OC CKZXADVHFFKWKQ-UHFFFAOYSA-N 0.000 description 1
- AISGCPJYLZUZOS-UHFFFAOYSA-N 2-hydroxy-1,2-bis(2-methylphenyl)ethanone Chemical compound CC1=CC=CC=C1C(O)C(=O)C1=CC=CC=C1C AISGCPJYLZUZOS-UHFFFAOYSA-N 0.000 description 1
- NBYSFWKNMLCZLO-UHFFFAOYSA-N 2-hydroxy-1,2-bis(4-methylphenyl)ethanone Chemical compound C1=CC(C)=CC=C1C(O)C(=O)C1=CC=C(C)C=C1 NBYSFWKNMLCZLO-UHFFFAOYSA-N 0.000 description 1
- MGUZTXXISNAEDO-UHFFFAOYSA-N 2-hydroxy-1,2-bis(4-phenylphenyl)ethanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(O)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 MGUZTXXISNAEDO-UHFFFAOYSA-N 0.000 description 1
- IRUVXSCYKGFCRG-UHFFFAOYSA-N 2-hydroxy-1-(3-methoxyphenyl)-2-phenylethanone Chemical compound COC1=CC=CC(C(=O)C(O)C=2C=CC=CC=2)=C1 IRUVXSCYKGFCRG-UHFFFAOYSA-N 0.000 description 1
- ZXFSXZYDGCZLBE-UHFFFAOYSA-N 2-hydroxy-1-(4-methylphenyl)-2-phenylethanone Chemical compound C1=CC(C)=CC=C1C(=O)C(O)C1=CC=CC=C1 ZXFSXZYDGCZLBE-UHFFFAOYSA-N 0.000 description 1
- XPMBXYLYQIAAMB-UHFFFAOYSA-N 2-hydroxy-2-phenyl-1-(2,4,6-trimethylphenyl)ethanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C(O)C1=CC=CC=C1 XPMBXYLYQIAAMB-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- WBBPRCNXBQTYLF-UHFFFAOYSA-N 2-methylthioethanol Chemical compound CSCCO WBBPRCNXBQTYLF-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- KWWZHCSQVRVQGF-UHFFFAOYSA-N 2-phenylsulfanylethanol Chemical compound OCCSC1=CC=CC=C1 KWWZHCSQVRVQGF-UHFFFAOYSA-N 0.000 description 1
- ZETHHMPKDUSZQQ-UHFFFAOYSA-N Betulafolienepentol Natural products C1C=C(C)CCC(C(C)CCC=C(C)C)C2C(OC)OC(OC)C2=C1 ZETHHMPKDUSZQQ-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- NBZANZVJRKXVBH-GYDPHNCVSA-N alpha-Cryptoxanthin Natural products O[C@H]1CC(C)(C)C(/C=C/C(=C\C=C\C(=C/C=C/C=C(\C=C\C=C(/C=C/[C@H]2C(C)=CCCC2(C)C)\C)/C)\C)/C)=C(C)C1 NBZANZVJRKXVBH-GYDPHNCVSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N beta-hydroxy propionic acid Natural products OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- HEOKFDGOFROELJ-UHFFFAOYSA-N diacetal Natural products COc1ccc(C=C/c2cc(O)cc(OC3OC(COC(=O)c4cc(O)c(O)c(O)c4)C(O)C(O)C3O)c2)cc1O HEOKFDGOFROELJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- LJFIHTFNTGQZJL-UHFFFAOYSA-N methyl 2-hydroxy-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(O)(C(=O)OC)C1=CC=CC=C1 LJFIHTFNTGQZJL-UHFFFAOYSA-N 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1129572A CH575965A5 (en) | 1972-07-28 | 1972-07-28 | Aromatic 1,2-diketone monoacetals - useful as photoinitiators and cross-linking agents |
| CH941773A CH587867A5 (en) | 1973-06-28 | 1973-06-28 | Aromatic 1,2-diketone monoacetals - useful as photoinitiators and cross-linking agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2337813A1 DE2337813A1 (de) | 1974-02-07 |
| DE2337813B2 DE2337813B2 (de) | 1976-07-22 |
| DE2337813C3 true DE2337813C3 (de) | 1981-11-19 |
Family
ID=25704784
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2337813A Expired DE2337813C3 (de) | 1972-07-28 | 1973-07-25 | Verfahren zur Herstellung von Monoacetalen aromatischer 1,2-Diketone |
| DE2365497A Expired DE2365497C2 (de) | 1972-07-28 | 1973-07-25 | Benzil-monoacetale und ihre Verwendung |
| DE2365852A Expired DE2365852C3 (de) | 1972-07-28 | 1973-07-25 | Verfahren zur Herstellung von Monoacetalen aromatischen 1,2-Diketone |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2365497A Expired DE2365497C2 (de) | 1972-07-28 | 1973-07-25 | Benzil-monoacetale und ihre Verwendung |
| DE2365852A Expired DE2365852C3 (de) | 1972-07-28 | 1973-07-25 | Verfahren zur Herstellung von Monoacetalen aromatischen 1,2-Diketone |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4190602A (enExample) |
| JP (1) | JPS5756456B2 (enExample) |
| DD (1) | DD105438A5 (enExample) |
| DE (3) | DE2337813C3 (enExample) |
| DK (1) | DK152726C (enExample) |
| ES (1) | ES417307A1 (enExample) |
| FI (1) | FI60194C (enExample) |
| FR (1) | FR2194698B1 (enExample) |
| GB (1) | GB1390006A (enExample) |
| IT (1) | IT995086B (enExample) |
| NL (1) | NL7310297A (enExample) |
| SE (1) | SE417426B (enExample) |
| SU (2) | SU508173A3 (enExample) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4160794A (en) * | 1974-12-24 | 1979-07-10 | Ciba-Geigy Corporation | 1-Oxo-2,2-[dialkylphosphono(alkyl)alkyloxy]-1,2-diphenylethane |
| FR2348180A1 (fr) * | 1976-04-14 | 1977-11-10 | Basf Ag | Procede de preparation de monoacetals de 1,2-dicetones aromatiques et utilisation de ces substances comme photo-inducteurs pour des melanges durcissables sous l'action de radiations |
| DE2616408A1 (de) * | 1976-04-14 | 1977-11-03 | Basf Ag | Durch uv-bestrahlung polymerisierbare gemische |
| US4287367A (en) | 1976-04-14 | 1981-09-01 | Basf Aktiengesellschaft | Manufacture of symmetrical or unsymmetrical monoacetals of aromatic 1,2-diketones |
| CH611633A5 (enExample) * | 1977-03-16 | 1979-06-15 | Espe Pharm Praep | |
| EP0002707B1 (de) | 1977-12-22 | 1982-04-07 | Ciba-Geigy Ag | Neue Aminoalkyl-benzilketale und ihre Verwendung als Initiatoren für die Photopolymerisation ungesättigter Verbindungen |
| IT1130074B (it) * | 1979-04-20 | 1986-06-11 | Hoffmann La Roche | Composti policiclici e procedimento per la loro preparazione |
| US4351708A (en) | 1980-02-29 | 1982-09-28 | Ciba-Geigy Corporation | Photochemically or thermally polymerizable mixtures |
| DE3008411A1 (de) * | 1980-03-05 | 1981-09-10 | Merck Patent Gmbh, 6100 Darmstadt | Neue aromatisch-aliphatische ketone, ihre verwendung als photoinitiatoren sowie photopolymerisierbare systeme enthaltend solche ketone |
| FR2489336B1 (fr) * | 1980-09-04 | 1985-09-13 | Rhone Poulenc Spec Chim | Procede de preparation de polymeres ou copolymeres hydrosolubles a poids moleculaire eleve et a faible teneur en monomere(s) residuel(s), a partir de monomeres olefiniquement insatures |
| IT1147805B (it) * | 1982-01-22 | 1986-11-26 | Lamberti Flli Spa | Metodo per la preparazione di monoacetali simmetrici degli 1,2-dichetoni aromatici a partire dai corrispondenti alfa idrossi chetoni |
| US4518676A (en) * | 1982-09-18 | 1985-05-21 | Ciba Geigy Corporation | Photopolymerizable compositions containing diaryliodosyl salts |
| DE3512179A1 (de) * | 1985-04-03 | 1986-12-04 | Merck Patent Gmbh, 6100 Darmstadt | Fotoinitiatoren fuer die fotopolymerisation in waessrigen systemen |
| KR910000199B1 (ko) * | 1986-04-15 | 1991-01-23 | 시바-가이기 코오포레이숀 | 액체 광개시제 혼합물 |
| US5288917A (en) * | 1986-04-15 | 1994-02-22 | Ciba-Geigy Corporation | Liquid photoinitiator mixtures |
| GB8715435D0 (en) * | 1987-07-01 | 1987-08-05 | Ciba Geigy Ag | Forming images |
| US4950795A (en) * | 1987-08-27 | 1990-08-21 | Ciba-Geigy Corporation | Oligomeric benzil ketals and their use as photoinitiators |
| US5095044A (en) * | 1987-08-27 | 1992-03-10 | Ciba-Geigy Corporation | Oligomeric benzil ketals and their use as photoinitiators |
| DE3834029A1 (de) * | 1988-10-06 | 1990-04-12 | Basf Ag | Verfahren zur herstellung von symmetrischen und unsymmetrischen monoacetalen aromatischer 1,2-diketone |
| US5081307A (en) * | 1989-07-14 | 1992-01-14 | Kawaguchi Chemical Co., Ltd. | Process for preparing 2,2-dimethoxy-2-phenylacetophenone |
| US5167972A (en) * | 1990-09-04 | 1992-12-01 | Wm. Wrigley Jr. Company | Method of stabilizing peptide sweeteners in cinnamon-flavored chewing gums and confections |
| US5139793A (en) * | 1990-07-10 | 1992-08-18 | Wm. Wrigley Jr. Company | Method of prolonging flavor in chewing gum by the use of cinnamic aldehyde propylene glycol acetal |
| US5277919A (en) * | 1990-09-04 | 1994-01-11 | Wm. Wrigley Jr. Company | Method of stabilizing peptide sweeteners in chewing gums and confections with benzaldehyde acetals |
| AU6916394A (en) * | 1993-06-04 | 1995-01-03 | Henkel Corporation | Citral acetal ethers of alpha-hydroxy phenyl ketones and polymerizable compositions |
| US6709742B2 (en) | 1998-05-18 | 2004-03-23 | Dow Global Technologies Inc. | Crosslinked elastic fibers |
| ES2269733T3 (es) * | 2001-07-17 | 2007-04-01 | Dow Global Technologies Inc. | Fibras elasticas bicomponentes y biconstituyentes y metodos de obtenc ion de estructuras celulosicas a partir de las mismas. |
| JP4967378B2 (ja) * | 2005-03-29 | 2012-07-04 | セイコーエプソン株式会社 | インク組成物 |
| EP1951511B1 (en) * | 2005-10-26 | 2018-09-12 | Dow Global Technologies LLC | Multi-layer, elastic articles |
| US8153243B2 (en) | 2005-12-09 | 2012-04-10 | Dow Global Technologies Llc | Interpolymers suitable for multilayer films |
| EP1927633A1 (en) | 2006-11-30 | 2008-06-04 | Seiko Epson Corporation | Ink composition, two-pack curing ink composition set, and recording method and recorded matter using these |
| JP5472670B2 (ja) | 2007-01-29 | 2014-04-16 | セイコーエプソン株式会社 | インクセット、インクジェット記録方法及び記録物 |
| US8894197B2 (en) * | 2007-03-01 | 2014-11-25 | Seiko Epson Corporation | Ink set, ink-jet recording method, and recorded material |
| JP4816976B2 (ja) * | 2007-08-09 | 2011-11-16 | セイコーエプソン株式会社 | 光硬化型インク組成物 |
| EP2028241A1 (en) * | 2007-08-09 | 2009-02-25 | Seiko Epson Corporation | Photocurable ink composition, ink cartridge, inkjet recording method and recorded matter |
| JP4766281B2 (ja) * | 2007-09-18 | 2011-09-07 | セイコーエプソン株式会社 | インクジェット記録用非水系インク組成物、インクジェット記録方法および記録物 |
| JP2009269397A (ja) | 2008-02-29 | 2009-11-19 | Seiko Epson Corp | 不透明層の形成方法、記録方法、インクセット、インクカートリッジ、記録装置 |
| US8048976B2 (en) | 2008-09-04 | 2011-11-01 | Amyris, Inc. | Polyfarnesenes |
| JP2011152747A (ja) * | 2010-01-28 | 2011-08-11 | Seiko Epson Corp | 水性インク組成物、およびインクジェット記録方法ならびに記録物 |
| JP5692490B2 (ja) * | 2010-01-28 | 2015-04-01 | セイコーエプソン株式会社 | 水性インク組成物、およびインクジェット記録方法ならびに記録物 |
| JP5845196B2 (ja) | 2011-02-02 | 2016-01-20 | 東洋合成工業株式会社 | ２，２−ジメトキシ−１，２−ジ−［４−（メタ）アクリロイルオキシ］フェニルエタン−１−オン、その製造方法及びラジカル重合開始剤並びに光硬化性組成物 |
| EP2902417B1 (en) | 2012-09-28 | 2017-01-11 | Fujifilm Corporation | Curable resin composition, water-soluble ink composition, ink set, and image formation method |
| WO2015019616A1 (en) | 2013-08-07 | 2015-02-12 | Toyo Gosei Co., Ltd. | Reagent for enhancing generation of chemical species |
| EP2886595B1 (en) * | 2013-12-20 | 2016-04-20 | Borealis AG | Polyolefin composition for medium/high/extra high voltage cables comprising benzil-type voltage stabiliser |
| EP2927302B1 (de) | 2014-04-03 | 2019-03-06 | Basf Se | Flammschutzmittel auf basis von substituierten di-, tri- und tetra-arylethanverbindungen |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD75637A (enExample) * | ||||
| DD75638A (enExample) * | ||||
| DE1051269B (de) * | 1953-03-11 | 1959-02-26 | Union Carbide Corp | Verfahren zur Herstellung von 1,1,3-Tri-(2-halogen-alkoxy)-alkanen |
| DE1923266U (de) | 1965-06-11 | 1965-09-09 | Simon Fritz | Segelspreizlatte. |
| DE1923266B2 (de) * | 1969-05-07 | 1977-09-29 | Basf Ag, 6700 Ludwigshafen | Alpha-hydroxymethylbenzoinaether |
| US3689565A (en) * | 1970-05-04 | 1972-09-05 | Horst Hoffmann | {60 -methylolbenzoin ethers |
| US3728377A (en) * | 1972-06-05 | 1973-04-17 | Eastman Kodak Co | 4,4-bis(alkoxycarbonyl)benzoin ethers |
-
1973
- 1973-07-11 FI FI2211/73A patent/FI60194C/fi active
- 1973-07-12 SE SE7309792A patent/SE417426B/sv unknown
- 1973-07-24 NL NL7310297A patent/NL7310297A/xx not_active Application Discontinuation
- 1973-07-25 DE DE2337813A patent/DE2337813C3/de not_active Expired
- 1973-07-25 DE DE2365497A patent/DE2365497C2/de not_active Expired
- 1973-07-25 DE DE2365852A patent/DE2365852C3/de not_active Expired
- 1973-07-26 DD DD172542A patent/DD105438A5/xx unknown
- 1973-07-26 SU SU1953510A patent/SU508173A3/ru active
- 1973-07-27 IT IT27241/73A patent/IT995086B/it active
- 1973-07-27 ES ES417307A patent/ES417307A1/es not_active Expired
- 1973-07-27 FR FR7327634A patent/FR2194698B1/fr not_active Expired
- 1973-07-27 DK DK416373A patent/DK152726C/da not_active IP Right Cessation
- 1973-07-27 GB GB3584473A patent/GB1390006A/en not_active Expired
- 1973-07-28 JP JP48085362A patent/JPS5756456B2/ja not_active Expired
-
1974
- 1974-06-20 SU SU742035589A patent/SU751329A3/ru active
-
1978
- 1978-06-22 US US05/919,580 patent/US4190602A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DK152726B (da) | 1988-05-02 |
| DE2365852B2 (de) | 1981-02-19 |
| NL7310297A (enExample) | 1974-01-30 |
| DE2337813B2 (de) | 1976-07-22 |
| US4190602A (en) | 1980-02-26 |
| FR2194698A1 (enExample) | 1974-03-01 |
| DD105438A5 (enExample) | 1974-04-20 |
| SU751329A3 (ru) | 1980-07-23 |
| FI60194B (fi) | 1981-08-31 |
| ES417307A1 (es) | 1976-06-01 |
| DK152726C (da) | 1988-10-24 |
| GB1390006A (en) | 1975-04-09 |
| JPS5756456B2 (enExample) | 1982-11-30 |
| SE417426B (sv) | 1981-03-16 |
| DE2365497C2 (de) | 1985-03-21 |
| AU5830773A (en) | 1975-01-23 |
| FI60194C (fi) | 1981-12-10 |
| SU508173A3 (ru) | 1976-03-25 |
| DE2365852A1 (de) | 1976-08-26 |
| DE2365852C3 (de) | 1981-10-15 |
| DE2337813A1 (de) | 1974-02-07 |
| JPS4955646A (enExample) | 1974-05-30 |
| US4190602B1 (enExample) | 1987-05-19 |
| DE2365497A1 (de) | 1975-04-24 |
| FR2194698B1 (enExample) | 1976-09-17 |
| IT995086B (it) | 1975-11-10 |
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| C3 | Grant after two publication steps (3rd publication) | ||
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