CH619247A5 - Process for the preparation of hard terpene resins from an alpha-pinene-containing mixture of terpene hydrocarbons - Google Patents
Process for the preparation of hard terpene resins from an alpha-pinene-containing mixture of terpene hydrocarbons Download PDFInfo
- Publication number
- CH619247A5 CH619247A5 CH1324375A CH1324375A CH619247A5 CH 619247 A5 CH619247 A5 CH 619247A5 CH 1324375 A CH1324375 A CH 1324375A CH 1324375 A CH1324375 A CH 1324375A CH 619247 A5 CH619247 A5 CH 619247A5
- Authority
- CH
- Switzerland
- Prior art keywords
- pinene
- terpene
- weight
- isomerization
- isomerate
- Prior art date
Links
- 235000007586 terpenes Nutrition 0.000 title claims abstract description 50
- 239000011347 resin Substances 0.000 title claims abstract description 38
- 229920005989 resin Polymers 0.000 title claims abstract description 38
- 239000000203 mixture Substances 0.000 title claims abstract description 34
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 26
- -1 terpene hydrocarbons Chemical class 0.000 title claims abstract description 26
- 150000003505 terpenes Chemical class 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims description 34
- 238000002360 preparation method Methods 0.000 title claims description 5
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 title abstract 5
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 claims abstract description 51
- GQVMHMFBVWSSPF-SOYUKNQTSA-N (4E,6E)-2,6-dimethylocta-2,4,6-triene Chemical compound C\C=C(/C)\C=C\C=C(C)C GQVMHMFBVWSSPF-SOYUKNQTSA-N 0.000 claims abstract description 25
- GQVMHMFBVWSSPF-UHFFFAOYSA-N cis-alloocimene Natural products CC=C(C)C=CC=C(C)C GQVMHMFBVWSSPF-UHFFFAOYSA-N 0.000 claims abstract description 25
- IHPKGUQCSIINRJ-UHFFFAOYSA-N β-ocimene Natural products CC(C)=CCC=C(C)C=C IHPKGUQCSIINRJ-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 12
- 230000001105 regulatory effect Effects 0.000 claims abstract description 5
- 238000006317 isomerization reaction Methods 0.000 claims description 35
- 239000000178 monomer Substances 0.000 claims description 33
- 238000006116 polymerization reaction Methods 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 18
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 16
- 241000779819 Syncarpia glomulifera Species 0.000 claims description 15
- 239000001739 pinus spp. Substances 0.000 claims description 15
- 229940036248 turpentine Drugs 0.000 claims description 15
- 239000012808 vapor phase Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 10
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 claims description 9
- 230000000379 polymerizing effect Effects 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 claims description 8
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 claims description 8
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 claims description 8
- 229930006722 beta-pinene Natural products 0.000 claims description 8
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 claims description 8
- 229930006737 car-3-ene Natural products 0.000 claims description 7
- 229930007796 carene Natural products 0.000 claims description 7
- BQOFWKZOCNGFEC-UHFFFAOYSA-N carene Chemical compound C1C(C)=CCC2C(C)(C)C12 BQOFWKZOCNGFEC-UHFFFAOYSA-N 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 238000004508 fractional distillation Methods 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 238000010538 cationic polymerization reaction Methods 0.000 claims description 3
- 230000000875 corresponding effect Effects 0.000 claims description 3
- 241000196324 Embryophyta Species 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims description 2
- 239000000539 dimer Substances 0.000 claims description 2
- 239000003205 fragrance Substances 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 5
- 238000001256 steam distillation Methods 0.000 description 4
- 238000004061 bleaching Methods 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000197 pyrolysis Methods 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229930006739 camphene Natural products 0.000 description 1
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 150000001993 dienes Chemical group 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/08—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI326874A FI50537C (fi) | 1974-11-11 | 1974-11-11 | Tapa valmistaa kovia terpeenihartseja alfa-pineeniä sisältävästä terpe enihiilivetyjen seoksesta |
| FI326774A FI50536C (fi) | 1974-11-11 | 1974-11-11 | Tapa valmistaa kovia terpeenihartseja alfa-pineeniä sisältävästä terpe enihiilivetyjen seoksesta |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH619247A5 true CH619247A5 (en) | 1980-09-15 |
Family
ID=26156682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1324375A CH619247A5 (en) | 1974-11-11 | 1975-10-13 | Process for the preparation of hard terpene resins from an alpha-pinene-containing mixture of terpene hydrocarbons |
Country Status (6)
| Country | Link |
|---|---|
| CH (1) | CH619247A5 (is") |
| DD (1) | DD125134A1 (is") |
| DE (1) | DE2545643C3 (is") |
| FR (1) | FR2290456A1 (is") |
| GB (1) | GB1490606A (is") |
| SE (1) | SE403789B (is") |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4797460A (en) * | 1987-01-12 | 1989-01-10 | Arizona Chemical Company | Tackifier resin composition and process for preparing same |
| RU2202561C2 (ru) * | 2001-04-20 | 2003-04-20 | Открытое акционерное общество Ангарский завод полимеров | Способ получения светлой нефтеполимерной смолы |
| CN104693329B (zh) * | 2015-03-28 | 2018-06-19 | 罗定市星光化工有限公司 | 一种萜烯树脂的环保生产工艺 |
-
1975
- 1975-10-11 DE DE19752545643 patent/DE2545643C3/de not_active Expired
- 1975-10-13 CH CH1324375A patent/CH619247A5/de not_active IP Right Cessation
- 1975-10-15 SE SE7511549A patent/SE403789B/xx not_active IP Right Cessation
- 1975-11-07 GB GB4620175A patent/GB1490606A/en not_active Expired
- 1975-11-10 FR FR7534241A patent/FR2290456A1/fr active Granted
- 1975-11-11 DD DD18939975A patent/DD125134A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2545643B2 (de) | 1978-03-09 |
| GB1490606A (en) | 1977-11-02 |
| DD125134A1 (is") | 1977-04-06 |
| FR2290456B1 (is") | 1980-04-30 |
| SE7511549L (sv) | 1976-05-12 |
| SE403789B (sv) | 1978-09-04 |
| DE2545643C3 (de) | 1978-10-26 |
| FR2290456A1 (fr) | 1976-06-04 |
| DE2545643A1 (de) | 1976-05-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: VEITSILUOTO OY |
|
| PL | Patent ceased | ||
| PL | Patent ceased |