SE455948B - Forfarande for partiell hydrering och svavelreduktion av tallharts - Google Patents
Forfarande for partiell hydrering och svavelreduktion av tallhartsInfo
- Publication number
- SE455948B SE455948B SE8400552A SE8400552A SE455948B SE 455948 B SE455948 B SE 455948B SE 8400552 A SE8400552 A SE 8400552A SE 8400552 A SE8400552 A SE 8400552A SE 455948 B SE455948 B SE 455948B
- Authority
- SE
- Sweden
- Prior art keywords
- acid
- resin
- catalyst
- mpa
- palladium
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- 229910052717 sulfur Inorganic materials 0.000 title claims description 17
- 239000011593 sulfur Substances 0.000 title claims description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims description 16
- 239000011347 resin Substances 0.000 claims description 53
- 229920005989 resin Polymers 0.000 claims description 53
- 239000003054 catalyst Substances 0.000 claims description 33
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 32
- 238000005984 hydrogenation reaction Methods 0.000 claims description 30
- 235000008331 Pinus X rigitaeda Nutrition 0.000 claims description 29
- 235000011613 Pinus brutia Nutrition 0.000 claims description 29
- 241000018646 Pinus brutia Species 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- QUUCYKKMFLJLFS-UHFFFAOYSA-N Dehydroabietan Natural products CC1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 QUUCYKKMFLJLFS-UHFFFAOYSA-N 0.000 claims description 5
- NFWKVWVWBFBAOV-UHFFFAOYSA-N Dehydroabietic acid Natural products OC(=O)C1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 NFWKVWVWBFBAOV-UHFFFAOYSA-N 0.000 claims description 5
- NFWKVWVWBFBAOV-MISYRCLQSA-N dehydroabietic acid Chemical compound OC(=O)[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 NFWKVWVWBFBAOV-MISYRCLQSA-N 0.000 claims description 5
- 229940118781 dehydroabietic acid Drugs 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- MHVJRKBZMUDEEV-UHFFFAOYSA-N (-)-ent-pimara-8(14),15-dien-19-oic acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C1CCC(C=C)(C)C=C1CC2 MHVJRKBZMUDEEV-UHFFFAOYSA-N 0.000 claims description 3
- YPGLTKHJEQHKSS-ASZLNGMRSA-N (1r,4ar,4bs,7r,8as,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@@H](C(C)C)C[C@@H]2CC1 YPGLTKHJEQHKSS-ASZLNGMRSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- MXYATHGRPJZBNA-KRFUXDQASA-N isopimaric acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@@](C=C)(C)CC2=CC1 MXYATHGRPJZBNA-KRFUXDQASA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- NQJDHQUUJULIEJ-MWDBYQCVSA-N (1s,4ar,4bs,7s)-7-ethyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid Chemical compound C1([C@@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@@](CC)(C)CC2=CC1 NQJDHQUUJULIEJ-MWDBYQCVSA-N 0.000 claims description 2
- UZZYXZWSOWQPIS-UHFFFAOYSA-N 3-fluoro-5-(trifluoromethyl)benzaldehyde Chemical compound FC1=CC(C=O)=CC(C(F)(F)F)=C1 UZZYXZWSOWQPIS-UHFFFAOYSA-N 0.000 claims description 2
- MXYATHGRPJZBNA-UHFFFAOYSA-N 4-epi-isopimaric acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C1CCC(C=C)(C)CC1=CC2 MXYATHGRPJZBNA-UHFFFAOYSA-N 0.000 claims description 2
- MHVJRKBZMUDEEV-APQLOABGSA-N (+)-Pimaric acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@](C=C)(C)C=C2CC1 MHVJRKBZMUDEEV-APQLOABGSA-N 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 230000036571 hydration Effects 0.000 description 4
- 238000006703 hydration reaction Methods 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 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 description 2
- 241000158147 Sator Species 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 150000003464 sulfur compounds Chemical class 0.000 description 2
- 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 description 2
- MLBYBBUZURKHAW-UHFFFAOYSA-N 4-epi-Palustrinsaeure Natural products CC12CCCC(C)(C(O)=O)C1CCC1=C2CCC(C(C)C)=C1 MLBYBBUZURKHAW-UHFFFAOYSA-N 0.000 description 1
- MLBYBBUZURKHAW-MISYRCLQSA-N Palustric acid Chemical compound C([C@@]12C)CC[C@@](C)(C(O)=O)[C@@H]1CCC1=C2CCC(C(C)C)=C1 MLBYBBUZURKHAW-MISYRCLQSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/475,482 US4507228A (en) | 1983-03-15 | 1983-03-15 | Partial hydrogenation of tall oil rosin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8400552D0 SE8400552D0 (sv) | 1984-02-03 |
| SE8400552L SE8400552L (sv) | 1984-09-16 |
| SE455948B true SE455948B (sv) | 1988-08-22 |
Family
ID=23887760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8400552A SE455948B (sv) | 1983-03-15 | 1984-02-03 | Forfarande for partiell hydrering och svavelreduktion av tallharts |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4507228A (OSRAM) |
| JP (1) | JPS59187064A (OSRAM) |
| DE (1) | DE3409174A1 (OSRAM) |
| FR (1) | FR2542731B1 (OSRAM) |
| GB (1) | GB2136421B (OSRAM) |
| NL (1) | NL186181C (OSRAM) |
| SE (1) | SE455948B (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4585584A (en) * | 1985-04-08 | 1986-04-29 | Union Camp Corporation | Process for preparing rosin esters of improved color |
| JPH02145668A (ja) * | 1988-11-28 | 1990-06-05 | Harima Chem Inc | 水素添加ロジンの製造方法 |
| FI122689B (fi) * | 2003-06-05 | 2012-05-31 | Forchem Oy | Menetelmä uuteaineiden poistamiseksi selluloosamassasta |
| RU2279913C1 (ru) * | 2004-12-10 | 2006-07-20 | Александр Иванович Козлов | Высокопористый ячеистый катализатор с кислотными свойствами для модифицирования канифоли |
| KR20080012831A (ko) * | 2005-03-21 | 2008-02-12 | 벤-구리온 유니버시티 오브 더 네게브 리서치 앤드 디벨럽먼트 어쏘러티 | 식물성 또는 동물성 오일로부터 디젤 연료의 제조 |
| RU2543163C2 (ru) | 2012-12-25 | 2015-02-27 | Аризона Кемикал Кампани, ЛЛК | Способ очистки канифоли |
| CN117358314B (zh) * | 2023-08-28 | 2025-10-28 | 青岛科技大学 | 催化剂Ni-Cu/N-MCHS@MS的制备方法及其在松香加氢制备氢化松香中的应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2331915A (en) * | 1940-12-19 | 1943-10-19 | Hercules Powder Co Ltd | Hydrogenation catalyst |
| US2367287A (en) * | 1941-04-09 | 1945-01-16 | Hercules Powder Co Ltd | Hydrogenation process |
| US2346793A (en) * | 1941-10-09 | 1944-04-18 | Hercules Powder Co Ltd | Derivative of rosin and rosin compounds |
| US2540582A (en) * | 1945-06-01 | 1951-02-06 | Standard Oil Dev Co | Hydrogenation |
| US2727885A (en) * | 1951-10-24 | 1955-12-20 | Hercules Powder Co Ltd | Process for producing tall oil alcohol |
| US2776276A (en) * | 1953-08-18 | 1957-01-01 | Hercules Powder Co Ltd | Rosin hydrogenation |
| US3489740A (en) * | 1966-02-21 | 1970-01-13 | Robinette Research Lab Inc | Removing sulfur containing or bearing compounds from organic compounds and resulting products |
| US3595887A (en) * | 1968-08-12 | 1971-07-27 | Gen Mills Inc | Hydrogenation of polymeric fat acids |
| US3655635A (en) * | 1969-01-28 | 1972-04-11 | Hercules Inc | Tall oil rosin of low sulfur content |
| GB1578122A (en) * | 1976-02-11 | 1980-11-05 | Johnson Matthey Co Ltd | Catalytic hydrogenation of fatty oils |
-
1983
- 1983-03-15 US US06/475,482 patent/US4507228A/en not_active Expired - Lifetime
-
1984
- 1984-02-03 SE SE8400552A patent/SE455948B/sv unknown
- 1984-02-08 GB GB08403287A patent/GB2136421B/en not_active Expired
- 1984-03-09 NL NLAANVRAGE8400772,A patent/NL186181C/xx not_active IP Right Cessation
- 1984-03-13 JP JP59048928A patent/JPS59187064A/ja active Granted
- 1984-03-13 DE DE19843409174 patent/DE3409174A1/de active Granted
- 1984-03-14 FR FR8403958A patent/FR2542731B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB8403287D0 (en) | 1984-03-14 |
| SE8400552L (sv) | 1984-09-16 |
| NL8400772A (nl) | 1984-10-01 |
| GB2136421B (en) | 1986-07-16 |
| JPS6326793B2 (OSRAM) | 1988-05-31 |
| GB2136421A (en) | 1984-09-19 |
| FR2542731B1 (fr) | 1988-03-11 |
| NL186181B (nl) | 1990-05-01 |
| JPS59187064A (ja) | 1984-10-24 |
| FR2542731A1 (fr) | 1984-09-21 |
| US4507228A (en) | 1985-03-26 |
| NL186181C (nl) | 1990-10-01 |
| DE3409174A1 (de) | 1984-09-20 |
| SE8400552D0 (sv) | 1984-02-03 |
| DE3409174C2 (OSRAM) | 1992-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NAL | Patent in force |
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