NL8602621A - Werkwijze voor de bereiding van esters. - Google Patents

Werkwijze voor de bereiding van esters. Download PDF

Info

Publication number: NL8602621A
Authority: NL; Netherlands
Prior art keywords: general formula; formula; process according; ammonium; mixture
Prior art date: 1985-10-18

Application number

NL8602621A

Other languages

English (en)

Dutch (nl)

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

1985-10-18

Filing date

1986-10-17

Publication date

1987-05-18

1986-10-17 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1987-05-18 Publication of NL8602621A publication Critical patent/NL8602621A/nl

Links

238000000034 method Methods 0.000 title claims description 51
150000002148 esters Chemical class 0.000 title description 42
150000001875 compounds Chemical class 0.000 claims description 21
238000002360 preparation method Methods 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
230000008569 process Effects 0.000 claims description 15
239000011541 reaction mixture Substances 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 11
239000007858 starting material Substances 0.000 claims description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
-1 iron ion Chemical class 0.000 claims description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 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 claims description 5
239000011734 sodium Substances 0.000 claims description 5
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
150000001350 alkyl halides Chemical class 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
150000001733 carboxylic acid esters Chemical class 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 4
239000002798 polar solvent Substances 0.000 claims description 4
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 claims description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
229910021645 metal ion Inorganic materials 0.000 claims description 3
239000011591 potassium Substances 0.000 claims description 3
BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
229910052782 aluminium Inorganic materials 0.000 claims description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims description 2
239000002585 base Substances 0.000 claims description 2
WGQKYBSKWIADBV-UHFFFAOYSA-O benzylaminium Chemical compound [NH3+]CC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-O 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical compound CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 claims description 2
ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 claims description 2
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 claims description 2
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 claims description 2
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 2
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims 1
229910001424 calcium ion Inorganic materials 0.000 claims 1
HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
229910001414 potassium ion Inorganic materials 0.000 claims 1
239000003586 protic polar solvent Substances 0.000 claims 1
229910001415 sodium ion Inorganic materials 0.000 claims 1
239000000203 mixture Substances 0.000 description 40
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
239000002253 acid Substances 0.000 description 12
238000000926 separation method Methods 0.000 description 11
238000004817 gas chromatography Methods 0.000 description 10
150000002576 ketones Chemical class 0.000 description 9
NFGXHKASABOEEW-LDRANXPESA-N methoprene Chemical compound COC(C)(C)CCCC(C)C\C=C\C(\C)=C\C(=O)OC(C)C NFGXHKASABOEEW-LDRANXPESA-N 0.000 description 9
NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
150000001299 aldehydes Chemical class 0.000 description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
125000004356 hydroxy functional group Chemical group O* 0.000 description 5
239000002904 solvent Substances 0.000 description 5
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
229930003633 citronellal Natural products 0.000 description 4
235000000983 citronellal Nutrition 0.000 description 4
238000001816 cooling Methods 0.000 description 4
150000002596 lactones Chemical class 0.000 description 4
229910003002 lithium salt Inorganic materials 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
150000000475 acetylene derivatives Chemical class 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000002955 isolation Methods 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000000047 product Substances 0.000 description 3
MNYBEULOKRVZKY-QQZWAFJOSA-N (2z,4e)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid Chemical compound COC(C)(C)CCCC(C)C\C=C\C(\C)=C/C(O)=O MNYBEULOKRVZKY-QQZWAFJOSA-N 0.000 description 2
UCSIFMPORANABL-SNVBAGLBSA-N (3r)-3,7-dimethyloctanal Chemical compound CC(C)CCC[C@@H](C)CC=O UCSIFMPORANABL-SNVBAGLBSA-N 0.000 description 2
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
159000000002 lithium salts Chemical class 0.000 description 2
150000002905 orthoesters Chemical class 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
150000003008 phosphonic acid esters Chemical class 0.000 description 2
150000003014 phosphoric acid esters Chemical class 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000009466 transformation Effects 0.000 description 2
238000005406 washing Methods 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
MNYBEULOKRVZKY-UHFFFAOYSA-N 11-methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(O)=O MNYBEULOKRVZKY-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical class CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
241000238631 Hexapoda Species 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
125000005396 acrylic acid ester group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910001413 alkali metal ion Inorganic materials 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
ALCHCTTXYBZTOT-DLYKSEDFSA-N azane;(2e,4e)-3,7,11-trimethyldodeca-2,4-dienoic acid Chemical compound N.CC(C)CCCC(C)C\C=C\C(\C)=C\C(O)=O ALCHCTTXYBZTOT-DLYKSEDFSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
229910001431 copper ion Inorganic materials 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
238000003912 environmental pollution Methods 0.000 description 1
QFXZANXYUCUTQH-UHFFFAOYSA-N ethynol Chemical group OC#C QFXZANXYUCUTQH-UHFFFAOYSA-N 0.000 description 1
WMYNMYVRWWCRPS-UHFFFAOYSA-N ethynoxyethane Chemical group CCOC#C WMYNMYVRWWCRPS-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
FYQGBXGJFWXIPP-UEVLXMDPSA-N hydroprene Chemical compound CCOC(=O)\C=C(/C)\C=C\CC(C)CCCC(C)C FYQGBXGJFWXIPP-UEVLXMDPSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000001261 hydroxy acids Chemical class 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Chemical group 0.000 description 1
229910052749 magnesium Chemical group 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
230000029052 metamorphosis Effects 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
YUXDLEGQKHDJGL-ORZLCKBQSA-M potassium;(2e,4e)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate Chemical compound [K+].COC(C)(C)CCCC(C)C\C=C\C(\C)=C\C([O-])=O YUXDLEGQKHDJGL-ORZLCKBQSA-M 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000003609 titanium compounds Chemical class 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/587—Monocarboxylic acid esters having at least two carbon-to-carbon double bonds
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NL8602621A 1985-10-18 1986-10-17 Werkwijze voor de bereiding van esters. NL8602621A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU402485		1985-10-18
HU854024A HU196946B (en)	1985-10-18	1985-10-18	Process for production of 2e, 4e-stereochemical unsaturated carbonic acid esthers

Publications (1)

Publication Number	Publication Date
NL8602621A true NL8602621A (nl)	1987-05-18

Family

ID=10966569

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8602621A NL8602621A (nl)	1985-10-18	1986-10-17	Werkwijze voor de bereiding van esters.

Country Status (13)

Country	Link
JP (1)	JPS62111947A (it)
BE (1)	BE905595A (it)
CS (1)	CS266596B2 (it)
DD (1)	DD252185A5 (it)
DE (1)	DE3635622A1 (it)
ES (1)	ES2002424A6 (it)
FI (1)	FI864220A (it)
FR (1)	FR2588865A1 (it)
GB (1)	GB2181733B (it)
HU (1)	HU196946B (it)
IT (1)	IT1197888B (it)
NL (1)	NL8602621A (it)
YU (1)	YU176686A (it)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8835581B2 (en) *	2012-06-08	2014-09-16	Az Electronic Materials (Luxembourg) S.A.R.L.	Neutral layer polymer composition for directed self assembly and processes thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2533033A1 (de) *	1975-07-24	1977-02-10	Zoecon Corp	Verfahren zur herstellung von fettsaeureestern
JPS5940997B2 (ja) *	1981-08-29	1984-10-03	太空機械株式会社	掘削装置

1985
- 1985-10-18 HU HU854024A patent/HU196946B/hu not_active IP Right Cessation
1986
- 1986-10-13 BE BE905595A patent/BE905595A/fr unknown
- 1986-10-15 DD DD86295296A patent/DD252185A5/de not_active IP Right Cessation
- 1986-10-17 JP JP61245660A patent/JPS62111947A/ja active Pending
- 1986-10-17 CS CS867509A patent/CS266596B2/cs unknown
- 1986-10-17 FI FI864220A patent/FI864220A/fi not_active IP Right Cessation
- 1986-10-17 GB GB8624989A patent/GB2181733B/en not_active Expired
- 1986-10-17 YU YU01766/86A patent/YU176686A/xx unknown
- 1986-10-17 ES ES8602657A patent/ES2002424A6/es not_active Expired
- 1986-10-17 IT IT22044/86A patent/IT1197888B/it active
- 1986-10-17 NL NL8602621A patent/NL8602621A/nl not_active Application Discontinuation
- 1986-10-17 FR FR8614424A patent/FR2588865A1/fr not_active Withdrawn
- 1986-10-20 DE DE19863635622 patent/DE3635622A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
JPS62111947A (ja)	1987-05-22
GB8624989D0 (en)	1986-11-19
GB2181733A (en)	1987-04-29
IT1197888B (it)	1988-12-21
CS266596B2 (en)	1990-01-12
IT8622044A0 (it)	1986-10-17
HUT41728A (en)	1987-05-28
BE905595A (fr)	1987-04-13
DE3635622A1 (de)	1987-04-23
DD252185A5 (de)	1987-12-09
ES2002424A6 (es)	1988-08-01
HU196946B (en)	1989-02-28
FR2588865A1 (fr)	1987-04-24
YU176686A (en)	1987-10-31
FI864220A (fi)	1987-04-19
CS750986A2 (en)	1989-04-14
FI864220A0 (fi)	1986-10-17
GB2181733B (en)	1989-05-10

Legal Events

Date	Code	Title	Description
1991-06-03	BV	The patent application has lapsed

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DE69307577T2 (de)	1997-07-24	Verfahren zur Herstellung eines Biphenylderivates
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EP0065354B1 (en)	1985-07-03	Process for the preparation of 1,1-bis phenyl-2-haloalkan-1-ols
SU585151A1 (ru)	1977-12-25	Способ получени -хлоркетонов
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US4219505A (en)	1980-08-26	Process for preparing tetrahalocyclohexanone
JP3371009B2 (ja)	2003-01-27	カルボン酸誘導体の製造方法
JPH0528214B2 (it)	1993-04-23
JP2003089690A (ja)	2003-03-28	２−置換チオピリミジン−４−カルボン酸エステルの製法