CS262682B2 - Process for the alkylation of pitches - Google Patents
Process for the alkylation of pitches Download PDFInfo
- Publication number
- CS262682B2 CS262682B2 CS87473A CS47387A CS262682B2 CS 262682 B2 CS262682 B2 CS 262682B2 CS 87473 A CS87473 A CS 87473A CS 47387 A CS47387 A CS 47387A CS 262682 B2 CS262682 B2 CS 262682B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- pitch
- weight
- alkylated
- pitches
- alkylation
- Prior art date
Links
- 239000011295 pitch Substances 0.000 title claims description 83
- 230000029936 alkylation Effects 0.000 title claims description 17
- 238000005804 alkylation reaction Methods 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 5
- 239000003245 coal Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000002480 mineral oil Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 235000010446 mineral oil Nutrition 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000004939 coking Methods 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- 239000002168 alkylating agent Substances 0.000 description 6
- 229940100198 alkylating agent Drugs 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000000571 coke Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000011302 mesophase pitch Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000011301 petroleum pitch Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- 238000005574 benzylation reaction Methods 0.000 description 3
- 239000011294 coal tar pitch Substances 0.000 description 3
- 230000020335 dealkylation Effects 0.000 description 3
- 238000006900 dealkylation reaction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- XMWGTKZEDLCVIG-UHFFFAOYSA-N 1-(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1 XMWGTKZEDLCVIG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 238000009835 boiling Methods 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
- 239000004917 carbon fiber Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000011269 tar Substances 0.000 description 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000001033 granulometry Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000011331 needle coke Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000011022 opal Substances 0.000 description 1
- 239000002006 petroleum coke Substances 0.000 description 1
- 239000011312 pitch solution Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000001304 sample melting Methods 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10C—WORKING-UP PITCH, ASPHALT, BITUMEN, TAR; PYROLIGNEOUS ACID
- C10C3/00—Working-up pitch, asphalt, bitumen
- C10C3/02—Working-up pitch, asphalt, bitumen by chemical means reaction
- C10C3/026—Working-up pitch, asphalt, bitumen by chemical means reaction with organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Working-Up Tar And Pitch (AREA)
- Inorganic Fibers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863608130 DE3608130A1 (de) | 1986-03-12 | 1986-03-12 | Verfahren zur herstellung modifizierter peche und deren verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS47387A2 CS47387A2 (en) | 1988-08-16 |
| CS262682B2 true CS262682B2 (en) | 1989-03-14 |
Family
ID=6296099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS87473A CS262682B2 (en) | 1986-03-12 | 1987-01-22 | Process for the alkylation of pitches |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4943365A (pl) |
| EP (1) | EP0236675B1 (pl) |
| JP (1) | JPS62220582A (pl) |
| CS (1) | CS262682B2 (pl) |
| DE (2) | DE3608130A1 (pl) |
| PL (1) | PL152346B1 (pl) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140346085A1 (en) * | 2013-05-24 | 2014-11-27 | Gs Caltex Corporation | Method of preparing pitch for carbon fiber |
| CN104178194A (zh) * | 2013-05-27 | 2014-12-03 | Gs加德士 | 碳纤维用沥青的制备方法 |
| US9162955B2 (en) * | 2013-11-19 | 2015-10-20 | Uop Llc | Process for pyrolysis of a coal feed |
| TWI657127B (zh) * | 2017-01-20 | 2019-04-21 | 台灣中油股份有限公司 | 增密劑 |
| CN108485694B (zh) * | 2018-04-11 | 2021-01-19 | 北京化工大学 | 一种共碳化法制备优质中间相沥青的方法 |
| RU2687899C2 (ru) * | 2018-11-01 | 2019-05-16 | Чингиз Николаевич Барнаков | Способ получения пека из отходов ректификации кубового остатка стирола |
| CN114959949B (zh) * | 2022-04-27 | 2023-06-13 | 北京化工大学 | 一种稠环芳烃基碳纤维及其制备方法 |
| CN115466626B (zh) * | 2022-09-21 | 2024-01-12 | 武汉科技大学 | 一种高品质各向同性沥青的制备方法 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE549777A (pl) * | ||||
| CA891474A (en) * | 1972-01-25 | W. Walsh John | Improved petroleum pitch binder | |
| DE410419C (de) * | 1923-03-01 | 1925-03-06 | Hoechst Ag | Verfahren zur Herstellung nicht verharzender Produkte aus Urteer |
| US2247375A (en) * | 1937-12-16 | 1941-07-01 | Atlantic Refining Co | Treatment of bituminous materials |
| US2545963A (en) * | 1948-12-02 | 1951-03-20 | Standard Oil Dev Co | Process for producing asphalt compositions |
| GB899598A (en) * | 1959-12-10 | 1962-06-27 | Chemical Engineering Wiltons L | Improvements in and relating to binding materials for carbon articles |
| US3769249A (en) * | 1973-03-01 | 1973-10-30 | Brien Corp O | Thermosetting plastics and method therefor |
| JPS5140889B2 (pl) * | 1973-10-25 | 1976-11-06 | ||
| JPS5235367B2 (pl) * | 1974-01-29 | 1977-09-08 | ||
| FR2308893A1 (fr) * | 1975-04-23 | 1976-11-19 | Creusot Loire | Echangeur tubulaire a embouts, travaillant a chaud et sous pre ssion |
| US4021356A (en) * | 1975-09-10 | 1977-05-03 | Texaco Inc. | Alkoxylated asphalts as co-surfactants in surfactant oil recovery processes usable in formations containing water having high concentrations of polyvalent ions such as calcium and magnesium |
| US4317809A (en) * | 1979-10-22 | 1982-03-02 | Union Carbide Corporation | Carbon fiber production using high pressure treatment of a precursor material |
| JPS5790093A (en) * | 1980-11-27 | 1982-06-04 | Cosmo Co Ltd | Treatment of petroleum heavy oil |
| SU1022985A1 (ru) * | 1980-12-05 | 1983-06-15 | Кузнецкий Филиал Восточного Научно-Исследовательского Углехимического Института | Способ стабилизации каменноугольного пека |
| JPS57147586A (en) * | 1981-03-10 | 1982-09-11 | Nippon Carbon Co Ltd | Modification of pitch for carbon fiber |
| SU992560A1 (ru) * | 1981-04-17 | 1983-01-30 | Berdnikov Mikhail P | Способ получени модифицированного таллового пека |
| US4464248A (en) * | 1981-08-11 | 1984-08-07 | Exxon Research & Engineering Co. | Process for production of carbon artifact feedstocks |
| US4431513A (en) * | 1982-03-30 | 1984-02-14 | Union Carbide Corporation | Methods for producing mesophase pitch and binder pitch |
| US4457828A (en) * | 1982-03-30 | 1984-07-03 | Union Carbide Corporation | Mesophase pitch having ellipspidal molecules and method for making the pitch |
| US4465585A (en) * | 1982-03-30 | 1984-08-14 | Union Carbide Corporation | Cholesteric mesophase pitch |
| CA1187653A (en) * | 1983-02-25 | 1985-05-28 | Samuel Cukier | Oxidation-resistant pitches |
| US4469585A (en) * | 1983-05-09 | 1984-09-04 | Samuel Cukier | Oxidation resistant pitches |
| US4631181A (en) * | 1984-03-31 | 1986-12-23 | Nippon Steel Corporation | Process for producing mesophase pitch |
-
1986
- 1986-03-12 DE DE19863608130 patent/DE3608130A1/de not_active Withdrawn
-
1987
- 1987-01-12 DE DE8787100273T patent/DE3761984D1/de not_active Expired - Lifetime
- 1987-01-12 EP EP87100273A patent/EP0236675B1/de not_active Expired - Lifetime
- 1987-01-22 CS CS87473A patent/CS262682B2/cs not_active IP Right Cessation
- 1987-03-09 US US07/023,646 patent/US4943365A/en not_active Expired - Lifetime
- 1987-03-11 PL PL1987264563A patent/PL152346B1/pl unknown
- 1987-03-12 JP JP62055447A patent/JPS62220582A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0236675A3 (en) | 1987-12-16 |
| PL152346B1 (en) | 1990-12-31 |
| DE3608130A1 (de) | 1987-09-17 |
| CS47387A2 (en) | 1988-08-16 |
| EP0236675B1 (de) | 1990-03-21 |
| JPS62220582A (ja) | 1987-09-28 |
| US4943365A (en) | 1990-07-24 |
| EP0236675A2 (de) | 1987-09-16 |
| PL264563A1 (en) | 1988-05-12 |
| DE3761984D1 (de) | 1990-04-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| IF00 | In force as of 2000-06-30 in czech republic | ||
| MK4A | Patent expired |
Effective date: 20020122 |