BE415943A

BE415943A -

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Publication number: BE415943A
Authority: BE; Belgium
Prior art keywords: condensation; compounds; page; process according; phenol
Prior art date

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English (en)

French (fr)

Publication of BE415943A publication Critical patent/BE415943A/fr

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WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 119
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 79
235000013824 polyphenols Nutrition 0.000 claims description 57
229920005989 resin Polymers 0.000 claims description 48
239000011347 resin Substances 0.000 claims description 48
239000003921 oil Substances 0.000 claims description 45
238000006243 chemical reaction Methods 0.000 claims description 42
238000009833 condensation Methods 0.000 claims description 41
230000005494 condensation Effects 0.000 claims description 41
238000000034 method Methods 0.000 claims description 37
239000000047 product Substances 0.000 claims description 32
239000003054 catalyst Substances 0.000 claims description 29
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 26
150000004820 halides Chemical class 0.000 claims description 25
239000000126 substance Substances 0.000 claims description 24
150000001299 aldehydes Chemical class 0.000 claims description 23
150000002989 phenols Chemical class 0.000 claims description 23
150000001875 compounds Chemical class 0.000 claims description 21
238000004519 manufacturing process Methods 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 20
230000008569 process Effects 0.000 claims description 20
239000007787 solid Substances 0.000 claims description 18
238000010438 heat treatment Methods 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 13
239000007795 chemical reaction product Substances 0.000 claims description 11
150000003505 terpenes Chemical class 0.000 claims description 10
235000007586 terpenes Nutrition 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
241000779819 Syncarpia glomulifera Species 0.000 claims description 8
239000001739 pinus spp. Substances 0.000 claims description 8
239000007858 starting material Substances 0.000 claims description 8
229940036248 turpentine Drugs 0.000 claims description 8
150000001260 acyclic compounds Chemical class 0.000 claims description 7
239000011541 reaction mixture Substances 0.000 claims description 6
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 5
150000001334 alicyclic compounds Chemical class 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
230000002035 prolonged effect Effects 0.000 claims description 5
125000002015 acyclic group Chemical group 0.000 claims description 4
238000004821 distillation Methods 0.000 claims description 4
CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane Chemical compound CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 claims description 4
150000003509 tertiary alcohols Chemical class 0.000 claims description 4
FAMJUFMHYAFYNU-UHFFFAOYSA-N 1-methyl-4-(propan-2-yl)cyclohex-1-ene Chemical compound CC(C)C1CCC(C)=CC1 FAMJUFMHYAFYNU-UHFFFAOYSA-N 0.000 claims description 3
125000002723 alicyclic group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
229920003986 novolac Polymers 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000003208 petroleum Substances 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
238000012937 correction Methods 0.000 claims 4
IDPDNNXNHBEYOL-UHFFFAOYSA-N (1-methyl-4-propan-2-ylcyclohexyl)benzene Chemical compound C1CC(C(C)C)CCC1(C)C1=CC=CC=C1 IDPDNNXNHBEYOL-UHFFFAOYSA-N 0.000 claims 1
MLKXDPUZXIRXEP-UHFFFAOYSA-N 2-[6-fluoro-2-methyl-3-[(4-methylsulfinylphenyl)methylidene]-1-indenyl]acetic acid Chemical class CC1=C(CC(O)=O)C2=CC(F)=CC=C2C1=CC1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-UHFFFAOYSA-N 0.000 claims 1
241000016649 Copaifera officinalis Species 0.000 claims 1
125000001931 aliphatic group Chemical group 0.000 claims 1
ZXRCAYWYTOIRQS-UHFFFAOYSA-N hydron;phenol;chloride Chemical class Cl.OC1=CC=CC=C1 ZXRCAYWYTOIRQS-UHFFFAOYSA-N 0.000 claims 1
239000003317 industrial substance Substances 0.000 claims 1
239000007859 condensation product Substances 0.000 description 48
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
238000001035 drying Methods 0.000 description 21
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 19
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 18
239000002966 varnish Substances 0.000 description 17
239000002253 acid Substances 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
-1 pinene Chemical compound 0.000 description 11
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000011592 zinc chloride Substances 0.000 description 9
235000005074 zinc chloride Nutrition 0.000 description 9
239000004359 castor oil Substances 0.000 description 8
235000019438 castor oil Nutrition 0.000 description 8
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 8
229930195733 hydrocarbon Natural products 0.000 description 8
229920003987 resole Polymers 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000004383 yellowing Methods 0.000 description 7
GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
229910001507 metal halide Inorganic materials 0.000 description 6
150000005309 metal halides Chemical class 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
239000001293 FEMA 3089 Substances 0.000 description 5
239000002585 base Substances 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
150000002430 hydrocarbons Chemical class 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
230000009471 action Effects 0.000 description 4
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230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
239000000463 material Substances 0.000 description 4
230000020477 pH reduction Effects 0.000 description 4
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229920003023 plastic Polymers 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 3
239000005792 Geraniol Substances 0.000 description 3
GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 3
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230000007423 decrease Effects 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000010685 fatty oil Substances 0.000 description 3
229940113087 geraniol Drugs 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
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229930004725 sesquiterpene Natural products 0.000 description 3
150000004354 sesquiterpene derivatives Chemical class 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
JCHBFSBFSWWPIN-UHFFFAOYSA-N 1,2-dichloro-1-methyl-4-propan-2-ylcyclohexane Chemical compound CC(C)C1CCC(C)(Cl)C(Cl)C1 JCHBFSBFSWWPIN-UHFFFAOYSA-N 0.000 description 2
GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical compound CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 description 2
JGKJMBOJWVAMIJ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-1-methylcyclohexan-1-ol;hydrate Chemical compound O.CC(C)(O)C1CCC(C)(O)CC1 JGKJMBOJWVAMIJ-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
150000001728 carbonyl compounds Chemical class 0.000 description 2
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150000001805 chlorine compounds Chemical class 0.000 description 2
RBNWAMSGVWEHFP-UHFFFAOYSA-N cis-p-Menthan-1,8-diol Natural products CC(C)(O)C1CCC(C)(O)CC1 RBNWAMSGVWEHFP-UHFFFAOYSA-N 0.000 description 2
150000001896 cresols Chemical class 0.000 description 2
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NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
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239000000194 fatty acid Substances 0.000 description 2
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150000004665 fatty acids Chemical class 0.000 description 2
230000004927 fusion Effects 0.000 description 2
239000004312 hexamethylene tetramine Substances 0.000 description 2
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239000013067 intermediate product Substances 0.000 description 2
150000002628 limonene derivativess Chemical class 0.000 description 2
229960004011 methenamine Drugs 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 0.000 description 2
239000010665 pine oil Substances 0.000 description 2
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NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
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REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
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239000001306 (7E,9E,11E,13E)-pentadeca-7,9,11,13-tetraen-1-ol Substances 0.000 description 1
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QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
235000005747 Carum carvi Nutrition 0.000 description 1
240000000467 Carum carvi Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
239000004859 Copal Substances 0.000 description 1
XXZAOMJCZBZKPV-UHFFFAOYSA-N DL-bornyl chloride Natural products C1CC2(C)C(Cl)CC1C2(C)C XXZAOMJCZBZKPV-UHFFFAOYSA-N 0.000 description 1
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PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 1
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150000007513 acids Chemical class 0.000 description 1
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XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
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WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
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ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
IRAQOCYXUMOFCW-CXTNEJHOSA-N cedrene Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1C(C)=CC2 IRAQOCYXUMOFCW-CXTNEJHOSA-N 0.000 description 1
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FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
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UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
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