CA1292477C - Acides arylcyclobutenyl amidoalkeoiques et leurs sels - Google Patents

Acides arylcyclobutenyl amidoalkeoiques et leurs sels

Info

Publication number: CA1292477C
Authority: CA; Canada
Prior art keywords: hydrogen; compound; alkyl; amido; aryl
Prior art date: 1987-01-08
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA000526920A

Other languages

English (en)

Inventor

Robert A. Kirchhoff

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.)

Dow Chemical Co

Original Assignee

Dow Chemical 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.)

1987-01-08

Filing date

1987-01-08

Publication date

1991-11-26

1987-01-08 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1987-01-08 Priority to CA000526920A priority Critical patent/CA1292477C/fr

1991-11-26 Application granted granted Critical

1991-11-26 Publication of CA1292477C publication Critical patent/CA1292477C/fr

2008-11-26 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000002253 acid Substances 0.000 title claims abstract description 77
125000003368 amide group Chemical group 0.000 title claims abstract description 58
150000003839 salts Chemical class 0.000 title claims abstract description 19
150000007513 acids Chemical class 0.000 title description 26
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 81
150000001875 compounds Chemical class 0.000 claims abstract description 47
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 44
150000005840 aryl radicals Chemical class 0.000 claims abstract description 25
150000001408 amides Chemical class 0.000 claims abstract description 15
-1 aromatic radical Chemical class 0.000 claims description 144
229910052739 hydrogen Inorganic materials 0.000 claims description 43
239000001257 hydrogen Substances 0.000 claims description 43
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 33
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
125000003118 aryl group Chemical group 0.000 claims description 26
125000001183 hydrocarbyl group Chemical group 0.000 claims description 23
239000002585 base Substances 0.000 claims description 22
150000003254 radicals Chemical class 0.000 claims description 22
125000002947 alkylene group Chemical group 0.000 claims description 16
125000006575 electron-withdrawing group Chemical group 0.000 claims description 16
229910021529 ammonia Inorganic materials 0.000 claims description 15
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
229920000412 polyarylene Polymers 0.000 claims description 12
150000001768 cations Chemical class 0.000 claims description 11
125000000743 hydrocarbylene group Chemical group 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
150000001342 alkaline earth metals Chemical class 0.000 claims description 10
125000000732 arylene group Chemical group 0.000 claims description 10
229910052783 alkali metal Inorganic materials 0.000 claims description 9
150000001340 alkali metals Chemical class 0.000 claims description 9
125000002877 alkyl aryl group Chemical group 0.000 claims description 9
150000002431 hydrogen Chemical group 0.000 claims description 9
125000004450 alkenylene group Chemical group 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 6
125000001475 halogen functional group Chemical group 0.000 claims description 6
125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 5
125000005248 alkyl aryloxy group Chemical group 0.000 claims description 5
125000004659 aryl alkyl thio group Chemical group 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 5
HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical compound OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 claims description 5
125000005529 alkyleneoxy group Chemical group 0.000 claims description 4
125000005110 aryl thio group Chemical group 0.000 claims description 4
125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 3
CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 claims description 3
125000006356 alkylene carbonyl group Chemical group 0.000 claims description 2
125000005237 alkyleneamino group Chemical group 0.000 claims description 2
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 abstract description 12
239000002904 solvent Substances 0.000 description 57
238000000034 method Methods 0.000 description 52
235000013350 formula milk Nutrition 0.000 description 41
239000000047 product Substances 0.000 description 41
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
229960005419 nitrogen Drugs 0.000 description 39
239000000178 monomer Substances 0.000 description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
238000006243 chemical reaction Methods 0.000 description 35
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 34
239000000243 solution Substances 0.000 description 34
238000006116 polymerization reaction Methods 0.000 description 31
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 28
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
239000003054 catalyst Substances 0.000 description 27
125000000217 alkyl group Chemical group 0.000 description 26
230000008569 process Effects 0.000 description 26
239000000203 mixture Substances 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
238000002360 preparation method Methods 0.000 description 20
235000019441 ethanol Nutrition 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
229960004756 ethanol Drugs 0.000 description 17
229920000642 polymer Polymers 0.000 description 17
238000010992 reflux Methods 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000003795 chemical substances by application Substances 0.000 description 14
125000001424 substituent group Chemical group 0.000 description 14
229940076134 benzene Drugs 0.000 description 13
229940073584 methylene chloride Drugs 0.000 description 13
239000004642 Polyimide Substances 0.000 description 12
125000003277 amino group Chemical group 0.000 description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
150000001491 aromatic compounds Chemical class 0.000 description 11
125000005843 halogen group Chemical group 0.000 description 11
229920001721 polyimide Polymers 0.000 description 11
239000000758 substrate Substances 0.000 description 11
229910052751 metal Inorganic materials 0.000 description 10
239000002184 metal Substances 0.000 description 10
229910052763 palladium Inorganic materials 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
150000008064 anhydrides Chemical class 0.000 description 9
238000000576 coating method Methods 0.000 description 9
238000005481 NMR spectroscopy Methods 0.000 description 8
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
238000007792 addition Methods 0.000 description 8
229960000443 hydrochloric acid Drugs 0.000 description 8
235000011167 hydrochloric acid Nutrition 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 7
229910052799 carbon Inorganic materials 0.000 description 7
125000004122 cyclic group Chemical group 0.000 description 7
FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical compound NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 description 7
239000000376 reactant Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
125000005270 trialkylamine group Chemical group 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
229910014033 C-OH Inorganic materials 0.000 description 6
229910014570 C—OH Inorganic materials 0.000 description 6
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 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000843 powder Substances 0.000 description 6
239000012429 reaction media Substances 0.000 description 6
150000003335 secondary amines Chemical class 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000011734 sodium Substances 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
208000005156 Dehydration Diseases 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
150000007942 carboxylates Chemical class 0.000 description 5
239000011248 coating agent Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
230000018044 dehydration Effects 0.000 description 5
238000006297 dehydration reaction Methods 0.000 description 5
229940093499 ethyl acetate Drugs 0.000 description 5
235000019439 ethyl acetate Nutrition 0.000 description 5
239000000463 material Substances 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
239000007858 starting material Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 4
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
125000000392 cycloalkenyl group Chemical group 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
239000000835 fiber Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000007789 gas Substances 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
239000003999 initiator Substances 0.000 description 4
125000004430 oxygen atom Chemical group O* 0.000 description 4
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000012779 reinforcing material Substances 0.000 description 4
150000003512 tertiary amines Chemical class 0.000 description 4
229920001187 thermosetting polymer Polymers 0.000 description 4
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
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 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
241000193803 Therea Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000853 adhesive Substances 0.000 description 3
230000001070 adhesive effect Effects 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
239000003513 alkali Substances 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
125000000304 alkynyl group Chemical group 0.000 description 3
125000005001 aminoaryl group Chemical group 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
239000004305 biphenyl Substances 0.000 description 3
235000011089 carbon dioxide Nutrition 0.000 description 3
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
239000000306 component Substances 0.000 description 3
238000007906 compression Methods 0.000 description 3
238000010276 construction Methods 0.000 description 3
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 3
150000001993 dienes Chemical class 0.000 description 3
LFXFELPOGZEOQP-UHFFFAOYSA-N ethyl 3-(2-chlorophenyl)-2-cyanopropanoate Chemical compound CCOC(=O)C(C#N)CC1=CC=CC=C1Cl LFXFELPOGZEOQP-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000000945 filler Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
125000004997 halocarbonyl group Chemical group 0.000 description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
150000003949 imides Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000155 melt Substances 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
229910052759 nickel Inorganic materials 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
229940093956 potassium carbonate Drugs 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
239000010453 quartz Substances 0.000 description 3
230000036647 reaction Effects 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
241000894007 species Species 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 2
KSLANAUEYUSFCF-UHFFFAOYSA-N 3-(2-chlorophenyl)-2-cyanopropanoic acid Chemical compound OC(=O)C(C#N)CC1=CC=CC=C1Cl KSLANAUEYUSFCF-UHFFFAOYSA-N 0.000 description 2
PWWUUGALKZGDSD-UHFFFAOYSA-N 3-(2-chlorophenyl)prop-2-enenitrile Chemical compound ClC1=CC=CC=C1C=CC#N PWWUUGALKZGDSD-UHFFFAOYSA-N 0.000 description 2
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical group O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
MBCAQKCDHFRESF-UHFFFAOYSA-N 4-aminobicyclo[4.2.0]octa-1(6),2,4-triene-7-carbonitrile Chemical compound NC1=CC=C2CC(C#N)C2=C1 MBCAQKCDHFRESF-UHFFFAOYSA-N 0.000 description 2
MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 2
WARXDDCYMKLEEL-UHFFFAOYSA-N 4-nitrobicyclo[4.2.0]octa-1(6),2,4-triene-7-carbonitrile Chemical compound [O-][N+](=O)C1=CC=C2CC(C#N)C2=C1 WARXDDCYMKLEEL-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
FIQIEWYXLLEXNR-UHFFFAOYSA-N [O-][N+](=O)S(=O)(=O)[N+]([O-])=O Chemical compound [O-][N+](=O)S(=O)(=O)[N+]([O-])=O FIQIEWYXLLEXNR-UHFFFAOYSA-N 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical class C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 2
ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
230000006315 carbonylation Effects 0.000 description 2
238000005810 carbonylation reaction Methods 0.000 description 2
150000003857 carboxamides Chemical class 0.000 description 2
150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
230000006835 compression Effects 0.000 description 2
238000000748 compression moulding Methods 0.000 description 2
125000002993 cycloalkylene group Chemical group 0.000 description 2
HFPGRVHMFSJMOL-UHFFFAOYSA-N dibromomethane Chemical compound Br[CH]Br HFPGRVHMFSJMOL-UHFFFAOYSA-N 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
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229920003023 plastic Polymers 0.000 description 1
229920005575 poly(amic acid) Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920002577 polybenzoxazole Polymers 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001225 polyester resin Polymers 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
239000009719 polyimide resin Substances 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000012256 powdered iron Substances 0.000 description 1
238000012673 precipitation polymerization Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical class CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000005060 rubber Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
125000003375 sulfoxide group Chemical group 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000004804 winding Methods 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

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

CA000526920A 1987-01-08 1987-01-08 Acides arylcyclobutenyl amidoalkeoiques et leurs sels Expired - Fee Related CA1292477C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000526920A CA1292477C (fr)	1987-01-08	1987-01-08	Acides arylcyclobutenyl amidoalkeoiques et leurs sels

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000526920A CA1292477C (fr)	1987-01-08	1987-01-08	Acides arylcyclobutenyl amidoalkeoiques et leurs sels

Publications (1)

Publication Number	Publication Date
CA1292477C true CA1292477C (fr)	1991-11-26

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Application Number	Title	Priority Date	Filing Date
CA000526920A Expired - Fee Related CA1292477C (fr)	1987-01-08	1987-01-08	Acides arylcyclobutenyl amidoalkeoiques et leurs sels

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CA (1)	CA1292477C (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN115957592A (zh) *	2021-10-13	2023-04-14	中国石油化工股份有限公司	脱碱精制剂及其制备方法和在干气脱碱性杂质中的应用

1987
- 1987-01-08 CA CA000526920A patent/CA1292477C/fr not_active Expired - Fee Related

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN115957592A (zh) *	2021-10-13	2023-04-14	中国石油化工股份有限公司	脱碱精制剂及其制备方法和在干气脱碱性杂质中的应用
CN115957592B (zh) *	2021-10-13	2024-11-29	中国石油化工股份有限公司	脱碱精制剂及其制备方法和在干气脱碱性杂质中的应用

Legal Events

Date	Code	Title	Description
1994-05-28	MKLA	Lapsed

Publication	Publication Date	Title
US4826997A (en)	1989-05-02	N-Substituted arylcyclo butenyl-maleimides
CA1242833A (fr)	1988-10-04	Polymeres derives de poly(arylcyclobutenes)
EP0242033B1 (fr)	1994-01-26	Compositions contenant de l'arylcyclobutène et compositions polymères obtenues à partir de celles-ci
EP0235128B1 (fr)	1991-05-29	Procede de preparation de compositions polymeres reactives a partir de compositions monomeres d'arylcyclobutene
EP0229757B1 (fr)	1994-01-12	Procede de collage de deux substrats a l'aide de compositions monomeres d'arylcyclobutene
US4638078A (en)	1987-01-20	Arylcyclobutenyl amido alkenoic acids and salts thereof
US4724260A (en)	1988-02-09	Unsaturated alkyl monoarylcyclobutane monomers
US5198551A (en)	1993-03-30	Polyamide thermosets
US4999449A (en)	1991-03-12	Novel poly(arylcyclobutenes)
CA1292477C (fr)	1991-11-26	Acides arylcyclobutenyl amidoalkeoiques et leurs sels
EP0191858B1 (fr)	1990-11-14	MONOMERES POLY(ARYLCYCLOBUTENES)et une méthode de leur polymerisation
US2497673A (en)	1950-02-14	Reaction of alpha-beta unsaturated compounds with aromatic hydrocarbons and products obtained
US4965329A (en)	1990-10-23	N-substituted arylcyclo butenyl-unsaturated cyclic imides
JP4056194B2 (ja)	2008-03-05	カルボン酸とアミンを用いたアミド縮合物の製造方法
CA1300635C (fr)	1992-05-12	Imides cycliques insatures de type arylcyclobutenyl, a azote substitue
US4174447A (en)	1979-11-13	Process for dimerization, arylation and trifluoromethylation of aromatic and heterocyclic compounds
US5026892A (en)	1991-06-25	Novel poly(arylcyclobutenes)
US4188274A (en)	1980-02-12	Process for trifluoromethylation of aromatic and heterocyclic compounds
US3518264A (en)	1970-06-30	Process for the preparation of triacrylyl perhydro-s-triazines
US5463108A (en)	1995-10-31	Process for preparing acetoxystyrene
CA2015164A1 (fr)	1990-11-15	Anhydride dioxydiphtalique
US5493062A (en)	1996-02-20	Process for preparing 4-hydroxystyrene
JPS6341456A (ja)	1988-02-22	新規ビスマレイミド化合物およびその製造方法
US5099083A (en)	1992-03-24	Process for preparing 3-chloromethylbenzo-cyclobutene
EP0255384B1 (fr)	1991-10-16	4,4-bis(carboxyphénylsulfonyl)diphényl éthers, leur procédé de préparation et emploi de ceux-ci