GB474465A - A process for the preparation of condensation products - Google Patents
A process for the preparation of condensation productsInfo
- Publication number
- GB474465A GB474465A GB14431/36A GB1443136A GB474465A GB 474465 A GB474465 A GB 474465A GB 14431/36 A GB14431/36 A GB 14431/36A GB 1443136 A GB1443136 A GB 1443136A GB 474465 A GB474465 A GB 474465A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenol
- condensed
- chloride
- oil
- treated
- Prior art date
- 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
Links
- 239000007859 condensation product Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 12
- 239000003921 oil Substances 0.000 abstract 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 9
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 abstract 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 8
- 239000011592 zinc chloride Substances 0.000 abstract 7
- 235000005074 zinc chloride Nutrition 0.000 abstract 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 6
- -1 hydrogen halides Chemical class 0.000 abstract 5
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 239000011347 resin Chemical class 0.000 abstract 4
- 229920005989 resin Chemical class 0.000 abstract 4
- 235000007586 terpenes Nutrition 0.000 abstract 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- 229910052782 aluminium Inorganic materials 0.000 abstract 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 3
- 150000003505 terpenes Chemical class 0.000 abstract 3
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 abstract 2
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 abstract 2
- 241000723346 Cinnamomum camphora Species 0.000 abstract 2
- 244000304337 Cuminum cyminum Species 0.000 abstract 2
- 235000007129 Cuminum cyminum Nutrition 0.000 abstract 2
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 abstract 2
- 239000005792 Geraniol Substances 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 2
- 241000779819 Syncarpia glomulifera Species 0.000 abstract 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 2
- 229930008380 camphor Natural products 0.000 abstract 2
- 229960000846 camphor Drugs 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- 229940113087 geraniol Drugs 0.000 abstract 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 abstract 2
- 150000002628 limonene derivativess Chemical class 0.000 abstract 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 abstract 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 abstract 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 abstract 2
- 239000010665 pine oil Substances 0.000 abstract 2
- 239000001739 pinus spp. Substances 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 229940036248 turpentine Drugs 0.000 abstract 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 abstract 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 abstract 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 abstract 1
- OQOIAVUGYLDTIJ-UHFFFAOYSA-N 6-methyl-1,6-diphenyl-3-propan-2-ylcyclohexane-1,2-diol Chemical compound C=1C=CC=CC=1C1(O)C(O)C(C(C)C)CCC1(C)C1=CC=CC=C1 OQOIAVUGYLDTIJ-UHFFFAOYSA-N 0.000 abstract 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 abstract 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 abstract 1
- 241000218631 Coniferophyta Species 0.000 abstract 1
- 241000016649 Copaifera officinalis Species 0.000 abstract 1
- 239000004859 Copal Substances 0.000 abstract 1
- 241000782205 Guibourtia conjugata Species 0.000 abstract 1
- 244000179970 Monarda didyma Species 0.000 abstract 1
- 235000010672 Monarda didyma Nutrition 0.000 abstract 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001260 acyclic compounds Chemical class 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001334 alicyclic compounds Chemical class 0.000 abstract 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 abstract 1
- 229940116229 borneol Drugs 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- IRAQOCYXUMOFCW-CXTNEJHOSA-N cedrene Chemical class C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1C(C)=CC2 IRAQOCYXUMOFCW-CXTNEJHOSA-N 0.000 abstract 1
- 229940043350 citral Drugs 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000001896 cresols Chemical class 0.000 abstract 1
- 239000001941 cymbopogon citratus dc and cymbopogon flexuosus oil Substances 0.000 abstract 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 abstract 1
- IRAQOCYXUMOFCW-UHFFFAOYSA-N di-epi-alpha-cedrene Chemical class C1C23C(C)CCC3C(C)(C)C1C(C)=CC2 IRAQOCYXUMOFCW-UHFFFAOYSA-N 0.000 abstract 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 abstract 1
- 229960001867 guaiacol Drugs 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002366 halogen compounds Chemical class 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 235000001510 limonene Nutrition 0.000 abstract 1
- 229940087305 limonene Drugs 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 150000004780 naphthols Chemical class 0.000 abstract 1
- 239000000025 natural resin Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 239000012262 resinous product Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229930004725 sesquiterpene Natural products 0.000 abstract 1
- 150000004354 sesquiterpene derivatives Chemical class 0.000 abstract 1
- USDOQCCMRDNVAH-UHFFFAOYSA-N sigma-cadinene Chemical class C1C=C(C)CC2C(C(C)C)CC=C(C)C21 USDOQCCMRDNVAH-UHFFFAOYSA-N 0.000 abstract 1
- 238000010025 steaming Methods 0.000 abstract 1
- 239000003784 tall oil Substances 0.000 abstract 1
- 229940116411 terpineol Drugs 0.000 abstract 1
- CRNIHJHMEQZAAS-UHFFFAOYSA-N tert-amyl chloride Chemical compound CCC(C)(C)Cl CRNIHJHMEQZAAS-UHFFFAOYSA-N 0.000 abstract 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 abstract 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 abstract 1
- 150000003739 xylenols Chemical class 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- USDOQCCMRDNVAH-KKUMJFAQSA-N β-cadinene Chemical class C1C=C(C)C[C@H]2[C@H](C(C)C)CC=C(C)[C@@H]21 USDOQCCMRDNVAH-KKUMJFAQSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
- C08G8/30—Chemically modified polycondensates by unsaturated compounds, e.g. terpenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L93/00—Compositions of natural resins; Compositions of derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Condensation products are prepared by reacting phenols (such as phenol, cresols, naphthols, polyhydroxybenzenes or alkoxyphenols) with halogen compounds obtained from halogens or hydrogen halides and terpenes or derivatives thereof or acyclic compounds which can easily be converted into alicyclic compounds, such as the olefinic terpenes or terpenogenes or those compounds of indefinite nature which are formed from terpene compounds of high molecular weight, such as natural resins, especially copals, by a simple treatment, for example, by heating, the reaction being effected in the presence of halides of the metals aluminium, zinc or iron or substances which form the same under the reaction conditions, such as zinc dust. Suitable substances include borneol, pinene, limonene, terpineol, terpene hydrate, sesquiterpenes, cadinene, cedrene, resin acids, resin alcohols, isoprene, geraniol, citral, and readily available materials such as oil of bergamot, lemon-grass oil, oil of turpentine, technical dipentenes, camphor, oil of camphor, cumin oil, conifer oils, pine oil, colophony, neutral natural soft resins, tall oil, and resin oils. Soft or even oily products are obtained when a small amount of phenol is used and with larger amounts harder and sometimes crystalline bodies are obtained, but soft products may be converted into hard by heating. In examples: (1) technical dipentene that has been saturated with hydrogen chloride is condensed with phenol in the presence of aluminium chloride to yield a crystalline dihydroxydiphenylmenthane which is converted on heating into a resinous product that has a polymerization-delaying action on drying oils; (2) dipentene hydrochloride is condensed with o-cresol or guaiacol in the presence of zinc chloride; (3) American oil of turpentine treated with hydrogen chloride is separated by steaming into the isomeric bornyl chlorides and each isomer is condensed with phenol; (4) a mixture of m- and p-cresol p is condensed with dipentene hydrochlorides in the presence of aluminium chloride; (5) American pine oil treated with hydrogen chloride is condensed with phenol in the presence of zinc chloride, excess phenol in the product being removed or alkylated by tert-butyl chloride; (6) cumin oil treated with hydrogen chloride is condensed with phenol in the presence of zinc chloride; (7) geraniol treated with hydrogen chloride is condensed with phenol in the presence of one of the specified catalysts; (8) a mixture of xylenol and American root extraction rosin is treated with hydrogen chloride and then condensed in the presence of aluminium or zinc chloride; (9) a chlorinated dipentene dihydrochloride is condensed with phenol in the presence of aluminium or zinc chloride, excess phenol being, if desired, converted into derivatives as by treatment with methyl butyl ketone, ethyl propyl ketone, acetone, cyclohexanone or methyl cyclohexanone; (10) a mixture of phenol and dipentene is treated with a small amount of hydrogen chloride or tert-amyl chloride and then condensed in the presence of zinc chloride; (11) a mixture of phenol and copal oil is treated with hydrogen chloride and then condensed in the presence of zinc chloride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE474465X | 1935-05-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB474465A true GB474465A (en) | 1937-11-02 |
Family
ID=6541722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB14431/36A Expired GB474465A (en) | 1935-05-25 | 1936-05-21 | A process for the preparation of condensation products |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB474465A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2472125A (en) * | 1945-03-02 | 1949-06-07 | Interchem Corp | Printing inks |
| US2588821A (en) * | 1952-03-11 | Coating compositions containing a |
-
1936
- 1936-05-21 GB GB14431/36A patent/GB474465A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2588821A (en) * | 1952-03-11 | Coating compositions containing a | ||
| US2472125A (en) * | 1945-03-02 | 1949-06-07 | Interchem Corp | Printing inks |
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