DD140457A5 - Verfahren zur herstellung von benzodifuranen - Google Patents

Verfahren zur herstellung von benzodifuranen Download PDF

Info

Publication number: DD140457A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; compound; compounds; alkyl; hydrogen
Prior art date: 1977-09-16

Application number

DD78207824A

Other languages

German (de)

English (en)

Inventor

Bruno Kaegi

Geza Kormany

Christian Luethi

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1977-09-16

Filing date

1978-09-14

Publication date

1980-03-05

1978-09-14 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1980-03-05 Publication of DD140457A5 publication Critical patent/DD140457A5/de

Links

238000000034 method Methods 0.000 title claims description 18
238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 61
239000003795 chemical substances by application Substances 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
239000003495 polar organic solvent Substances 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 abstract description 25
239000001257 hydrogen Substances 0.000 abstract description 23
229910052739 hydrogen Inorganic materials 0.000 abstract description 23
150000002431 hydrogen Chemical group 0.000 abstract description 18
229910052736 halogen Chemical group 0.000 abstract description 16
150000002367 halogens Chemical group 0.000 abstract description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 5
125000001424 substituent group Chemical group 0.000 abstract description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
-1 cyano, phenyl Chemical group 0.000 description 27
239000000047 product Substances 0.000 description 23
239000000243 solution Substances 0.000 description 18
125000003545 alkoxy group Chemical group 0.000 description 17
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
229920000728 polyester Polymers 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
239000000203 mixture Substances 0.000 description 12
230000003287 optical effect Effects 0.000 description 11
239000011368 organic material Substances 0.000 description 11
150000003839 salts Chemical class 0.000 description 11
238000005282 brightening Methods 0.000 description 10
229910052801 chlorine Inorganic materials 0.000 description 10
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
239000000835 fiber Substances 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
239000002253 acid Substances 0.000 description 7
125000004104 aryloxy group Chemical group 0.000 description 7
238000001816 cooling Methods 0.000 description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
125000004093 cyano group Chemical group *C#N 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000004744 fabric Substances 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
239000011734 sodium Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000009987 spinning Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000004753 textile Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
239000000654 additive Substances 0.000 description 5
229910052784 alkaline earth metal Inorganic materials 0.000 description 5
239000013078 crystal Substances 0.000 description 5
238000004043 dyeing Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
229920000915 polyvinyl chloride Polymers 0.000 description 5
239000004800 polyvinyl chloride Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000007858 starting material Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
239000004793 Polystyrene Substances 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
238000006068 polycondensation reaction Methods 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
229920002223 polystyrene Polymers 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
238000004061 bleaching Methods 0.000 description 3
239000007844 bleaching agent Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
238000000576 coating method Methods 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000000155 melt Substances 0.000 description 3
239000000049 pigment Substances 0.000 description 3
229920000137 polyphosphoric acid Polymers 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000011877 solvent mixture Substances 0.000 description 3
239000000758 substrate Substances 0.000 description 3
OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 2
AGXDTDFNRRZENA-UHFFFAOYSA-N 1-(4-acetyl-2,5-dihydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC(O)=C(C(C)=O)C=C1O AGXDTDFNRRZENA-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000003213 activating effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
125000002843 carboxylic acid group Chemical group 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
239000002131 composite material Substances 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
239000000975 dye Substances 0.000 description 2
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238000007363 ring formation reaction Methods 0.000 description 2
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239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
238000006277 sulfonation reaction Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
230000002087 whitening effect Effects 0.000 description 2
239000008096 xylene Substances 0.000 description 2
239000011592 zinc chloride Substances 0.000 description 2
235000005074 zinc chloride Nutrition 0.000 description 2
ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
229940005561 1,4-benzoquinone Drugs 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
PIWMYUGNZBJTID-UHFFFAOYSA-N 2,5-dihydroxyterephthalaldehyde Chemical compound OC1=CC(C=O)=C(O)C=C1C=O PIWMYUGNZBJTID-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-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
UMLFTCYAQPPZER-UHFFFAOYSA-N 4-(bromomethyl)benzonitrile Chemical compound BrCC1=CC=C(C#N)C=C1 UMLFTCYAQPPZER-UHFFFAOYSA-N 0.000 description 1
ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 description 1
WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
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101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical class OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
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FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
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230000029936 alkylation Effects 0.000 description 1
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AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
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239000012876 carrier material Substances 0.000 description 1
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
229920003086 cellulose ether Polymers 0.000 description 1
239000012295 chemical reaction liquid Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910001919 chlorite Inorganic materials 0.000 description 1
229910052619 chlorite group Inorganic materials 0.000 description 1
QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000004042 decolorization Methods 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
239000003599 detergent Substances 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
238000007599 discharging Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000005530 etching Methods 0.000 description 1
FYIBGDKNYYMMAG-UHFFFAOYSA-N ethane-1,2-diol;terephthalic acid Chemical compound OCCO.OC(=O)C1=CC=C(C(O)=O)C=C1 FYIBGDKNYYMMAG-UHFFFAOYSA-N 0.000 description 1
125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000011194 food seasoning agent Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
239000012760 heat stabilizer Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
239000004413 injection moulding compound Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000011872 intimate mixture Substances 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000010409 ironing Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000000990 laser dye Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
239000010985 leather Substances 0.000 description 1
239000004611 light stabiliser Substances 0.000 description 1
229910001510 metal chloride Inorganic materials 0.000 description 1
125000005395 methacrylic acid group Chemical class 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000002929 natural lacquer Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000003921 oil Substances 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000003973 paint Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
229920002959 polymer blend Polymers 0.000 description 1
229920006324 polyoxymethylene Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
150000003112 potassium compounds Chemical class 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229940048086 sodium pyrophosphate Drugs 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000019832 sodium triphosphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
230000008961 swelling Effects 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
238000009988 textile finishing Methods 0.000 description 1
238000007669 thermal treatment Methods 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
- 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
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/825—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups all hydroxy groups bound to the ring
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Detergent Compositions (AREA)
Plural Heterocyclic Compounds (AREA)

DD78207824A 1977-09-16 1978-09-14 Verfahren zur herstellung von benzodifuranen DD140457A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
LU78135A LU78135A1 (de)	1977-09-16	1977-09-16	Verfahren zur herstellung von benzodifuranen

Publications (1)

Publication Number	Publication Date
DD140457A5 true DD140457A5 (de)	1980-03-05

Family

ID=19728699

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD78207824A DD140457A5 (de)	1977-09-16	1978-09-14	Verfahren zur herstellung von benzodifuranen

Country Status (10)

Country	Link
US (1)	US4222739A (fr)
JP (1)	JPS5463129A (fr)
CA (1)	CA1097364A (fr)
DD (1)	DD140457A5 (fr)
DE (1)	DE2839595A1 (fr)
FR (1)	FR2403342A1 (fr)
GB (1)	GB2004871B (fr)
LU (1)	LU78135A1 (fr)
NL (1)	NL7809427A (fr)
SU (1)	SU837325A3 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8824108D0 (en) *	1988-10-14	1988-11-23	Unilever Plc	Bleaching & detergent compositions
WO2017159025A1 (fr) *	2016-03-15	2017-09-21	ソニー株式会社	Élément de conversion photoélectrique et dispositif de prise d'image à semi-conducteurs
HUE058789T2 (hu)	2017-06-05	2022-09-28	Senju Metal Industry Co	Forrasztó berendezés

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE787580A (fr) *	1971-08-13	1973-02-14	Hoechst Ag	Procede de preparation de derives du furanne
US3971731A (en) *	1973-02-09	1976-07-27	Bayer Aktiengesellschaft	Benzodifuran compounds
DE2306515A1 (de) *	1973-02-09	1974-08-15	Bayer Ag	Benzo-difuran-verbindungen

1977
- 1977-09-16 LU LU78135A patent/LU78135A1/de unknown
1978
- 1978-09-11 US US05/941,429 patent/US4222739A/en not_active Expired - Lifetime
- 1978-09-12 DE DE19782839595 patent/DE2839595A1/de not_active Withdrawn
- 1978-09-14 JP JP11244478A patent/JPS5463129A/ja active Pending
- 1978-09-14 CA CA311,343A patent/CA1097364A/fr not_active Expired
- 1978-09-14 DD DD78207824A patent/DD140457A5/de unknown
- 1978-09-15 FR FR7826601A patent/FR2403342A1/fr active Granted
- 1978-09-15 GB GB7837015A patent/GB2004871B/en not_active Expired
- 1978-09-15 NL NL7809427A patent/NL7809427A/xx not_active Application Discontinuation
1979
- 1979-01-03 SU SU792705007A patent/SU837325A3/ru active

Also Published As

Publication number	Publication date
FR2403342A1 (fr)	1979-04-13
LU78135A1 (de)	1979-05-23
GB2004871A (en)	1979-04-11
JPS5463129A (en)	1979-05-21
DE2839595A1 (de)	1979-03-29
CA1097364A (fr)	1981-03-10
GB2004871B (en)	1982-03-24
FR2403342B1 (fr)	1981-10-30
SU837325A3 (ru)	1981-06-07
US4222739A (en)	1980-09-16
NL7809427A (nl)	1979-03-20

Publication	Publication Date	Title
DE2733156C2 (fr)	1991-09-05
DE2262633A1 (de)	1973-07-05	Neue sulfogruppenhaltige 4,4'divinyldiphenyl-verbindungen
DE2238734A1 (de)	1973-02-22	Benzofuran-derivate, verfahren zu deren herstellung und verwendung als optische aufheller
DE1900537C2 (de)	1983-11-24	Styrylnaphthalin-Derivate, Verfahren zu deren Herstellung und deren Verwendung
DE1793482A1 (de)	1972-03-09	Neue Bis-stilben-Verbindungen,Verfahren zu deren Herstellung und Verwendung
DE1294923B (de)	1969-05-14	Optische Aufhellmittel
DE2807008A1 (de)	1978-08-24	Phenyl-benzimidazolyl-furane
DE2645301A1 (de)	1977-04-14	1,4-bis- eckige klammer auf azolyl- (2') eckige klammer zu -naphthaline
DE2209128C3 (de)	1981-10-22	Bis-Stilbenverbindungen, Verfahren zu deren Herstellung und deren Verwendung als optische Aufheller
DE1294917B (de)	1969-05-14	Optisches Aufhellmittel
EP0002042A1 (fr)	1979-05-30	Composés diaminés de 1,3,5-triazinylstilbène, leur procédé de préparation et leur emploi comme azurants optiques
DD140457A5 (de)	1980-03-05	Verfahren zur herstellung von benzodifuranen
DE2946481C2 (fr)	1991-06-06
DE2309614A1 (de)	1973-09-20	Azolverbindungen, verfahren zu deren herstellung und deren verwendung
EP0054511B1 (fr)	1987-05-13	4-Styryle-4'-vinylbiphényles, méthodes pour leur préparation et leur emploi comme azurants optiques
DE2247791A1 (de)	1973-04-12	Optische aufhellmittel
DE2212480C2 (de)	1984-03-29	Neue Triazolyl-äthenylphenylenverbindungen, deren Herstellung und Verwendung als optische Aufheller
DE2332089C2 (de)	1984-01-26	2,7-Distyryl-dibenzofurane und deren Verwendung
DE2525683A1 (de)	1976-01-02	Sulfogruppenhaltige heterocyclen
DE2306399A1 (de)	1973-08-23	4,4'-dinaphthyl-1,1',8,8'-tetracarbonsaeurediimide als optische aufhellmittel
CH650792A5 (en)	1985-08-15	Optical brighteners from bisstyrylbenzene compounds and preparation thereof
DE2750577A1 (de)	1978-09-28	Stilbenverbindungen
DE1794386C3 (de)	1975-06-19	Verwendung von Bis-stilben-Verbindungen als optische Aufhellmittel
DE1719353A1 (de)	1971-05-19	Aryloxazolderivate als optische Aufhellmittel
DE2609421A1 (de)	1976-09-16	Neue benzoxazol-styryle