CH407080A - Verfahren zur Herstellung von Epoxyalkylestern - Google Patents

Verfahren zur Herstellung von Epoxyalkylestern

Info

Publication number: CH407080A
Authority: CH; Switzerland
Prior art keywords: salts; water; esters; dependent; monocarboxylic acids
Prior art date: 1959-05-19

Application number

CH563460A

Other languages

German (de)

English (en)

Inventor

Kloos Nantko

Johan Drost Jacques Joseph

Hendrik Andreae Josephus

Frederik Kreps Robert Willem

Klootwijk Arie

Original Assignee

Shell Int Research

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.)

1959-05-19

Filing date

1960-05-17

Publication date

1966-02-15

1960-05-17 Application filed by Shell Int Research filed Critical Shell Int Research

1962-07-02 Priority to CH793862A priority Critical patent/CH450377A/de

1966-02-15 Publication of CH407080A publication Critical patent/CH407080A/de

Links

150000002148 esters Chemical class 0.000 title claims description 47
238000000034 method Methods 0.000 title claims description 40
238000002360 preparation method Methods 0.000 title claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
-1 aliphatic monocarboxylic acids Chemical class 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 25
239000000243 solution Substances 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 17
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 13
150000007513 acids Chemical class 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 11
239000000203 mixture Substances 0.000 claims description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
239000007788 liquid Substances 0.000 claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
239000007864 aqueous solution Substances 0.000 claims description 8
150000002763 monocarboxylic acids Chemical class 0.000 claims description 7
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
238000005886 esterification reaction Methods 0.000 claims description 4
150000002576 ketones Chemical class 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
230000032050 esterification Effects 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
239000000725 suspension Substances 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 2
230000007717 exclusion Effects 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 7
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims 1
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims 1
239000000839 emulsion Substances 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 24
239000002904 solvent Substances 0.000 description 18
239000003054 catalyst Substances 0.000 description 17
229920000180 alkyd Polymers 0.000 description 12
150000001735 carboxylic acids Chemical class 0.000 description 10
239000004593 Epoxy Substances 0.000 description 9
150000001734 carboxylic acid salts Chemical class 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
159000000000 sodium salts Chemical class 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000001336 alkenes Chemical class 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
238000004821 distillation Methods 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
238000009835 boiling Methods 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 5
239000007858 starting material Substances 0.000 description 5
238000005406 washing Methods 0.000 description 5
239000002585 base Substances 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000005907 alkyl ester group Chemical group 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
238000010533 azeotropic distillation Methods 0.000 description 3
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
238000001914 filtration Methods 0.000 description 3
150000005673 monoalkenes Chemical class 0.000 description 3
239000003973 paint Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
239000002966 varnish Substances 0.000 description 3
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
229910015900 BF3 Inorganic materials 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
238000000576 coating method Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 2
QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 2
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
238000002845 discoloration Methods 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
125000003700 epoxy group Chemical group 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000012535 impurity Substances 0.000 description 2
229910017053 inorganic salt Inorganic materials 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
150000002605 large molecules Chemical class 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 2
JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 2
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
SRXBOKMHGNRUSG-UHFFFAOYSA-N 2-(1-chloropropyl)-3-propyloxirane Chemical compound CCCC1OC1C(Cl)CC SRXBOKMHGNRUSG-UHFFFAOYSA-N 0.000 description 1
MMTOSBCMFDNOIY-UHFFFAOYSA-N 2-(chloromethyl)-3-methyloxirane Chemical compound CC1OC1CCl MMTOSBCMFDNOIY-UHFFFAOYSA-N 0.000 description 1
OIFAHDAXIUURLN-UHFFFAOYSA-N 2-(fluoromethyl)oxirane Chemical compound FCC1CO1 OIFAHDAXIUURLN-UHFFFAOYSA-N 0.000 description 1
WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
238000005698 Diels-Alder reaction Methods 0.000 description 1
QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
239000002879 Lewis base Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
AOIIZSJDYSLFOI-UHFFFAOYSA-L benzyl(trimethyl)azanium;sulfate Chemical compound [O-]S([O-])(=O)=O.C[N+](C)(C)CC1=CC=CC=C1.C[N+](C)(C)CC1=CC=CC=C1 AOIIZSJDYSLFOI-UHFFFAOYSA-L 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
229910002090 carbon oxide Inorganic materials 0.000 description 1
125000005588 carbonic acid salt group Chemical group 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
MMQWEMMTKXBCLU-UHFFFAOYSA-M cyclohexyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)C1CCCCC1 MMQWEMMTKXBCLU-UHFFFAOYSA-M 0.000 description 1
239000003599 detergent Substances 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
MODVWHOORBAIIW-UHFFFAOYSA-N dimethyl(diphenyl)azanium borate Chemical compound [O-]B([O-])[O-].C[N+](C)(c1ccccc1)c1ccccc1.C[N+](C)(c1ccccc1)c1ccccc1.C[N+](C)(c1ccccc1)c1ccccc1 MODVWHOORBAIIW-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
239000000446 fuel Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
150000007527 lewis bases Chemical class 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
FRQONEWDWWHIPM-UHFFFAOYSA-N n,n-dicyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)C1CCCCC1 FRQONEWDWWHIPM-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
229940055577 oleyl alcohol Drugs 0.000 description 1
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
238000003825 pressing Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
239000004753 textile Substances 0.000 description 1
238000004227 thermal cracking Methods 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
GUXFJQKRMRPFSQ-UHFFFAOYSA-M trioctyl(phenyl)azanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C1=CC=CC=C1 GUXFJQKRMRPFSQ-UHFFFAOYSA-M 0.000 description 1
ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
- C08G63/42—Cyclic ethers; Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1515—Three-membered rings
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/55—Epoxy resins
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Epoxy Compounds (AREA)

CH563460A 1959-05-19 1960-05-17 Verfahren zur Herstellung von Epoxyalkylestern CH407080A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH793862A CH450377A (de)	1960-05-17	1962-07-02	Verfahren für die Herstellung von Gemischen von Epoxyalkylestern gesättigter aliphatischer Monocarbonsäuren, in denen die Carboxylgruppen an tertiäre und/oder quaternäre Kohlenstoffatome gebunden sind

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
NL239307		1959-05-19
NL240769		1959-06-30
NL245932		1959-11-30

Publications (1)

Publication Number	Publication Date
CH407080A true CH407080A (de)	1966-02-15

Family

ID=27351016

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH563460A CH407080A (de)	1959-05-19	1960-05-17	Verfahren zur Herstellung von Epoxyalkylestern

Country Status (3)

Country	Link
CH (1)	CH407080A (da)
DK (1)	DK105865C (da)
GB (1)	GB936808A (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1012478B (it) *	1974-05-17	1977-03-10	Snam Progetti	Processo per la preparazione di epossidi di enolesteri organici
CN109608931B (zh) *	2018-12-04	2021-11-16	广东维拓化工股份有限公司	一种绿色建筑墙体用的环保涂料及其制备方法

1960
- 1960-05-17 GB GB1739060A patent/GB936808A/en not_active Expired
- 1960-05-17 CH CH563460A patent/CH407080A/de unknown
- 1960-05-19 DK DK608260A patent/DK105865C/da active

Also Published As

Publication number	Publication date
GB936808A (en)	1963-09-11
DK105865C (da)	1966-11-21

Publication	Publication Date	Title
DE69901510T2 (de)	2002-08-29	Verfahren zur herstellung von glycidylestern verzweigter carbonsäuren
DE3815826A1 (de)	1989-11-23	Verfahren zur herstellung von vicinal diacyloxysubstituierten verbindungen
DE1668500A1 (de)	1972-04-06	Verfahren zur Herstellung von Epoxiden
CH418642A (de)	1966-08-15	Verfahren zur Herstellung neuartiger Alkydharze
EP0025961B1 (de)	1983-05-25	Verfahren zur Herstellung von 1,2-Diolen höherer Kohlenstoffzahl
DE3611302A1 (de)	1987-10-08	Fluorierte, mehrwertige alkohole, verfahren zu ihrer herstellung und ihre verwendung
DE1053781B (de)	1959-03-26	Verfahren zur Herstellung von haertbaren Epoxyharzen
CH407080A (de)	1966-02-15	Verfahren zur Herstellung von Epoxyalkylestern
EP0155238A2 (de)	1985-09-18	Verfahren zur Herstellung bestimmter Glycidylverbindungen
DE2844637C2 (de)	1986-07-10	Verfahren zur Herstellung von 2,3- Dimethyl-2,3-butandiol
DD157804A5 (de)	1982-12-08	Verfahren zur herstellung von malathion
EP0008112B1 (de)	1983-01-19	Verfahren zur Herstellung von Glycidylestern aromatischer Polycarbonsäuren
EP0305925B1 (de)	1992-01-29	Verfahren zur Herstellung von Umsetzungsprodukten epoxidierter Ricinolsäureglyceride mit Schwefeltrioxid
EP0033110A1 (de)	1981-08-05	Verfahren zur Herstellung von Epoxyalkanen
EP0017832B1 (de)	1982-12-22	Verfahren zur Herstellung von 5-Brom-5-nitro-1,3-dioxan
DE3247255A1 (de)	1984-06-28	Verfahren zur herstellung von isolierung von polyglycidylverbindungen
EP0008111B1 (de)	1983-01-26	Verfahren zur Herstellung von Glycidylestern cycloaliphatischer Polycarbonsäuren
DE871449C (de)	1953-03-23	Verfahren zur Herstellung des Pentaerythrit-dichlorhydrin-monoschwefligsaeureesters
DE1493082A1 (de)	1969-02-13	Verfahren zur Herstellung von Glycidylestern von Monocarbonsaeuren
DE801991C (de)	1951-02-01	Verfahren zur Herstellung von Carbonsaeureestersulfonsaeuren
DE692927C (de)	1940-06-28	Verfahren zur Herstellung kapillaraktiver quartaerer Basen
DE1917031A1 (de)	1969-10-23	Verfahren zur Oxydation von Propylen
DE2835883A1 (de)	1980-02-28	Verfahren zur herstellung von maleinsaeureglycidylestern
AT325586B (de)	1975-10-27	Verfahren zur herstellung von bernsteinsäuredimethylester
DE1568001C3 (de)	1978-02-09	Verfahren zur Herstellung von Epoxyden