CA2034435A1 - Methode pour effectuer des reactions chimiques a l'aide de sel d'hexaalkylguanidinium, utilise comme catalyseur a transfert de phase - Google Patents

Methode pour effectuer des reactions chimiques a l'aide de sel d'hexaalkylguanidinium, utilise comme catalyseur a transfert de phase

Info

Publication number: CA2034435A1
Authority: CA; Canada
Prior art keywords: salt; hexaalkylguanidinium; alkali metal; compound; reaction
Prior art date: 1990-02-05
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.): Abandoned

Application number

CA 2034435

Other languages

English (en)

Inventor

Daniel J. Brunelle

Deborah A. Haitko

James P. Barren

Sunita Singh

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

General Electric Co

Original Assignee

General Electric Co

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.)

1990-02-05

Filing date

1991-01-17

Publication date

1991-08-06

1991-01-17 Application filed by General Electric Co filed Critical General Electric Co

1991-08-06 Publication of CA2034435A1 publication Critical patent/CA2034435A1/fr

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 34
150000003839 salts Chemical class 0.000 title claims abstract description 34
239000003444 phase transfer catalyst Substances 0.000 title claims abstract description 13
238000006053 organic reaction Methods 0.000 title abstract 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 44
238000006243 chemical reaction Methods 0.000 claims abstract description 37
-1 alkali metal salt Chemical class 0.000 claims abstract description 26
150000001875 compounds Chemical class 0.000 claims abstract description 24
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 13
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 12
150000001491 aromatic compounds Chemical class 0.000 claims abstract description 11
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 5
239000008096 xylene Substances 0.000 claims abstract description 5
VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical class C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 claims abstract description 4
239000003495 polar organic solvent Substances 0.000 claims abstract description 4
125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 4
ANYWGXDASKQYAD-UHFFFAOYSA-N 5-nitroisoindole-1,3-dione Chemical class [O-][N+](=O)C1=CC=C2C(=O)NC(=O)C2=C1 ANYWGXDASKQYAD-UHFFFAOYSA-N 0.000 claims abstract 4
239000002904 solvent Substances 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 9
SUHYKYPAFONDDV-UHFFFAOYSA-M bis(diethylamino)methylidene-diethylazanium;bromide Chemical group [Br-].CCN(CC)C(N(CC)CC)=[N+](CC)CC SUHYKYPAFONDDV-UHFFFAOYSA-M 0.000 claims description 6
LYWKAJZTPLXHEM-UHFFFAOYSA-M bis(diethylamino)methylidene-diethylazanium;chloride Chemical group [Cl-].CCN(CC)C(N(CC)CC)=[N+](CC)CC LYWKAJZTPLXHEM-UHFFFAOYSA-M 0.000 claims description 6
150000003949 imides Chemical class 0.000 claims description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 3
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
DZMGZZJLEGLBNJ-UHFFFAOYSA-M bis(dibutylamino)methylidene-dibutylazanium;bromide Chemical group [Br-].CCCCN(CCCC)C(N(CCCC)CCCC)=[N+](CCCC)CCCC DZMGZZJLEGLBNJ-UHFFFAOYSA-M 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
239000011591 potassium Chemical group 0.000 claims description 2
229910052700 potassium Chemical group 0.000 claims description 2
CASUWTAPYGBPLM-UHFFFAOYSA-M bis(dibutylamino)methylidene-dibutylazanium;chloride Chemical group [Cl-].CCCCN(CCCC)C(N(CCCC)CCCC)=[N+](CCCC)CCCC CASUWTAPYGBPLM-UHFFFAOYSA-M 0.000 claims 1
125000003944 tolyl group Chemical group 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 8
238000007339 nucleophilic aromatic substitution reaction Methods 0.000 abstract description 4
239000007787 solid Substances 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000000203 mixture Substances 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 14
238000010992 reflux Methods 0.000 description 12
239000000243 solution Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 8
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 7
239000003153 chemical reaction reagent Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000012071 phase Substances 0.000 description 4
150000002989 phenols Chemical class 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
UWHSPZZUAYSGTB-UHFFFAOYSA-N 1,1,3,3-tetraethylurea Chemical compound CCN(CC)C(=O)N(CC)CC UWHSPZZUAYSGTB-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
150000001450 anions Chemical group 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
ZECBPBHBGNLLMU-UHFFFAOYSA-M sodium;4-methylphenolate Chemical compound [Na+].CC1=CC=C([O-])C=C1 ZECBPBHBGNLLMU-UHFFFAOYSA-M 0.000 description 3
238000005406 washing Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
LSVBBJVITBGNFC-UHFFFAOYSA-N 2-butyl-5-nitroisoindole-1,3-dione Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(CCCC)C(=O)C2=C1 LSVBBJVITBGNFC-UHFFFAOYSA-N 0.000 description 2
FBJOJDGPSNQMMK-UHFFFAOYSA-N 3-[4-[4-(2,3-dicarboxyphenoxy)phenyl]phenoxy]phthalic acid Chemical group OC(=O)C1=CC=CC(OC=2C=CC(=CC=2)C=2C=CC(OC=3C(=C(C(O)=O)C=CC=3)C(O)=O)=CC=2)=C1C(O)=O FBJOJDGPSNQMMK-UHFFFAOYSA-N 0.000 description 2
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 2
BONIIQYTWOPUQI-UHFFFAOYSA-N 4-nitroisoindole-1,3-dione Chemical class [O-][N+](=O)C1=CC=CC2=C1C(=O)NC2=O BONIIQYTWOPUQI-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000004985 diamines Chemical class 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical group CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
238000006073 displacement reaction Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000012454 non-polar solvent Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
150000004714 phosphonium salts Chemical class 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000003880 polar aprotic solvent Substances 0.000 description 2
229920001601 polyetherimide Polymers 0.000 description 2
238000004064 recycling Methods 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
150000003457 sulfones Chemical class 0.000 description 2
POOSGDOYLQNASK-UHFFFAOYSA-N tetracosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC POOSGDOYLQNASK-UHFFFAOYSA-N 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
SNDGLCYYBKJSOT-UHFFFAOYSA-N 1,1,3,3-tetrabutylurea Chemical group CCCCN(CCCC)C(=O)N(CCCC)CCCC SNDGLCYYBKJSOT-UHFFFAOYSA-N 0.000 description 1
QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
MQXNNWDXHFBFEB-UHFFFAOYSA-N 2,2-bis(2-hydroxyphenyl)propane Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1O MQXNNWDXHFBFEB-UHFFFAOYSA-N 0.000 description 1
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
ZFXDUWYVZMVVQT-UHFFFAOYSA-N 3-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=CC(O)=CC=1C(C)(C)C1=CC=C(O)C=C1 ZFXDUWYVZMVVQT-UHFFFAOYSA-N 0.000 description 1
XZWYIEAOALEANP-UHFFFAOYSA-N 3-[4-[2-[4-(2,3-dicarboxyphenoxy)phenyl]propan-2-yl]phenoxy]phthalic acid Chemical compound C=1C=C(OC=2C(=C(C(O)=O)C=CC=2)C(O)=O)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=CC(C(O)=O)=C1C(O)=O XZWYIEAOALEANP-UHFFFAOYSA-N 0.000 description 1
RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
STIUDHAPUDGWOI-UHFFFAOYSA-N 4-(4-hydroxyphenyl)phenol;sodium Chemical compound [Na].[Na].C1=CC(O)=CC=C1C1=CC=C(O)C=C1 STIUDHAPUDGWOI-UHFFFAOYSA-N 0.000 description 1
RQCACQIALULDSK-UHFFFAOYSA-N 4-(4-hydroxyphenyl)sulfinylphenol Chemical compound C1=CC(O)=CC=C1S(=O)C1=CC=C(O)C=C1 RQCACQIALULDSK-UHFFFAOYSA-N 0.000 description 1
CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
WCUDAIJOADOKAW-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)pentan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(CCC)C1=CC=C(O)C=C1 WCUDAIJOADOKAW-UHFFFAOYSA-N 0.000 description 1
KJLPSBMDOIVXSN-UHFFFAOYSA-N 4-[4-[2-[4-(3,4-dicarboxyphenoxy)phenyl]propan-2-yl]phenoxy]phthalic acid Chemical compound C=1C=C(OC=2C=C(C(C(O)=O)=CC=2)C(O)=O)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 KJLPSBMDOIVXSN-UHFFFAOYSA-N 0.000 description 1
KGZDWASJUFIKMH-UHFFFAOYSA-N 4-[4-hydroxy-2-(3-hydroxyphenyl)phenyl]sulfonyl-3-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=C(O)C=2)S(=O)(=O)C=2C(=CC(O)=CC=2)C=2C=C(O)C=CC=2)=C1 KGZDWASJUFIKMH-UHFFFAOYSA-N 0.000 description 1
QATSOLLSVDVSAL-UHFFFAOYSA-N 4-[hydroxy(phenyl)methyl]phenol Chemical compound C=1C=C(O)C=CC=1C(O)C1=CC=CC=C1 QATSOLLSVDVSAL-UHFFFAOYSA-N 0.000 description 1
HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
239000004642 Polyimide Substances 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
150000008378 aryl ethers Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000005110 aryl thio group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
CJTDRDJUGRBDKP-UHFFFAOYSA-N bis(dibutylamino)methylidene-dibutylazanium Chemical compound CCCCN(CCCC)C(N(CCCC)CCCC)=[N+](CCCC)CCCC CJTDRDJUGRBDKP-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 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
239000004202 carbamide Substances 0.000 description 1
RYTLGWCJESCDMY-UHFFFAOYSA-N carbamimidoyl chloride Chemical class NC(Cl)=N RYTLGWCJESCDMY-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000002950 deficient Effects 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
125000006159 dianhydride group Chemical group 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011491 glass wool Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
KHARCSTZAGNHOT-UHFFFAOYSA-N naphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 KHARCSTZAGNHOT-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002931 p-cresols Chemical class 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
FUGYGGDSWSUORM-UHFFFAOYSA-N para-hydroxystyrene Natural products OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 1
125000005010 perfluoroalkyl group Chemical group 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
239000001294 propane Substances 0.000 description 1
PFZCOWLKXHIVII-UHFFFAOYSA-N pyridin-1-ium-1-amine Chemical class N[N+]1=CC=CC=C1 PFZCOWLKXHIVII-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
238000013112 stability test Methods 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Indole Compounds (AREA)

CA 2034435 1990-02-05 1991-01-17 Methode pour effectuer des reactions chimiques a l'aide de sel d'hexaalkylguanidinium, utilise comme catalyseur a transfert de phase Abandoned CA2034435A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US47486990A	1990-02-05	1990-02-05
US474,869		1990-02-05

Publications (1)

Publication Number	Publication Date
CA2034435A1 true CA2034435A1 (fr)	1991-08-06

Family

ID=23885272

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2034435 Abandoned CA2034435A1 (fr)	1990-02-05	1991-01-17	Methode pour effectuer des reactions chimiques a l'aide de sel d'hexaalkylguanidinium, utilise comme catalyseur a transfert de phase

Country Status (1)

Country	Link
CA (1)	CA2034435A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN106380426A (zh) *	2016-08-18	2017-02-08	黎明化工研究设计院有限责任公司	一种水相法制备四丁基脲的方法
CN106478461A (zh) *	2016-08-18	2017-03-08	黎明化工研究设计院有限责任公司	一种乙醇法制备四丁基脲的方法
US11279692B2 (en) *	2015-12-29	2022-03-22	Shpp Global Technologies B.V.	Methods for the manufacture of an aromatic bisimide and a polyetherimide

1991
- 1991-01-17 CA CA 2034435 patent/CA2034435A1/fr not_active Abandoned

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US11279692B2 (en) *	2015-12-29	2022-03-22	Shpp Global Technologies B.V.	Methods for the manufacture of an aromatic bisimide and a polyetherimide
CN106380426A (zh) *	2016-08-18	2017-02-08	黎明化工研究设计院有限责任公司	一种水相法制备四丁基脲的方法
CN106478461A (zh) *	2016-08-18	2017-03-08	黎明化工研究设计院有限责任公司	一种乙醇法制备四丁基脲的方法
CN106478461B (zh) *	2016-08-18	2018-03-09	黎明化工研究设计院有限责任公司	一种乙醇法制备四丁基脲的方法
CN106380426B (zh) *	2016-08-18	2018-03-09	黎明化工研究设计院有限责任公司	一种水相法制备四丁基脲的方法

Legal Events

Date	Code	Title	Description
1996-07-17	FZDE	Dead

Publication	Publication Date	Title
US5132423A (en)	1992-07-21	Method for conducting organic reactions using guanidinium salt as phase transfer catalyst
US5081298A (en)	1992-01-14	Bis(pentaalkylguanidinium) alkane salts as phase transfer catalysts
US5116975A (en)	1992-05-26	Bis(guanidinium)alkane salts as phase transfer catalysts
US4273712A (en)	1981-06-16	Method for making aromatic ether imides
US4257953A (en)	1981-03-24	Method for making bisphenoxide salts and bisimides derived therefrom
US4460778A (en)	1984-07-17	Phase transfer catalysts
US5229482A (en)	1993-07-20	Phase transfer catalyzed preparation of aromatic polyether polymers
KR910003821B1 (ko)	1991-06-12	하이드록시방향족 화합물의 프로파르길 에테르를 제조하는 방법
US4329292A (en)	1982-05-11	Continuous method for making aromatic bis(ether phthalic acid) or aromatic bis(ether anhydride)
EP0142835B1 (fr)	1989-09-06	Sels de bis-aminopyridinium et leur emploi comme catalyseur de transfert pour la préparation d'éther-imides aromatiques
EP0273159B1 (fr)	1991-08-14	Synthèse de composés aromatiques du type bis(étherphtalimide)
US4513141A (en)	1985-04-23	Method for making aromatic ethers using diorganoamino pyridinum salt catalyst
US4808731A (en)	1989-02-28	Method for making oxydiphthalic anhydride
US5359084A (en)	1994-10-25	Method of preparing aromatic ether bisimides
US4681949A (en)	1987-07-21	Bis-aminopyridinium salts as phase transfer catalysts for aromatic ether imide preparation
US4554357A (en)	1985-11-19	Bis-quaternary salts as phase transfer catalysts for aromatic ether imide preparation
US4302616A (en)	1981-11-24	Method for making alkali metal bisphenoxide salts and bisimides derived therefrom
US3850964A (en)	1974-11-26	Method for making aromatic bis(ether anhydride)s
US4605745A (en)	1986-08-12	N-neopentyl-4-diorganoamino pyridinium compounds
CA2034435A1 (fr)	1991-08-06	Methode pour effectuer des reactions chimiques a l'aide de sel d'hexaalkylguanidinium, utilise comme catalyseur a transfert de phase
CA2199669C (fr)	2008-01-22	Catalyseur d'halogenation
US4577033A (en)	1986-03-18	Heterocyclic quaternary ammonium salts as phase transfer catalysts for aromatic ether imide preparation
CA2044470A1 (fr)	1992-09-14	Methode pour effectuer des reactions organiques en utilisant du sel de guanidinium comme catalyseur de transfert de phase
EP1403303B1 (fr)	2008-08-20	Procèdès pour la preparation de poly(etherimide)s
US4471125A (en)	1984-09-11	Method for making aromatic ether imides