KR850003379A - 유기용매존재하에 c₄유분을 선택적으로 수소화시키는 공정 - Google Patents
유기용매존재하에 c₄유분을 선택적으로 수소화시키는 공정 Download PDFInfo
- Publication number
- KR850003379A KR850003379A KR1019840006650A KR840006650A KR850003379A KR 850003379 A KR850003379 A KR 850003379A KR 1019840006650 A KR1019840006650 A KR 1019840006650A KR 840006650 A KR840006650 A KR 840006650A KR 850003379 A KR850003379 A KR 850003379A
- Authority
- KR
- South Korea
- Prior art keywords
- hydrocarbon
- fraction
- process according
- amine compound
- weight
- Prior art date
Links
- 238000005984 hydrogenation reaction Methods 0.000 title claims 4
- 239000003960 organic solvent Substances 0.000 title 1
- -1 C 4 hydrocarbon Chemical class 0.000 claims 9
- 238000000034 method Methods 0.000 claims 7
- 239000004215 Carbon black (E152) Substances 0.000 claims 6
- 229930195733 hydrocarbon Natural products 0.000 claims 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- 150000002430 hydrocarbons Chemical group 0.000 claims 4
- 239000007791 liquid phase Substances 0.000 claims 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 1
- GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 claims 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims 1
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/107—Alkenes with six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/08—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
- C07C7/167—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation for removal of compounds containing a triple carbon-to-carbon bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/44—Palladium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
도면은 본 발명의 실시예를 도시해주는 생산공정 일람표이다.
Claims (10)
- 부틴 및 비닐아세틸렌을 가진 적어도 한 개의 아세틸렌계 탄화수소그룹과 부타디엔을 포함하는 C4탄화수소유분을 액상에서 알루미나에 침전된 팔라듐 촉매와 접촉시켜 수소화반응을 선택적으로 일으키는데 있어서, 상기 유분은 최소한 한 개의 방향족 탄화수소 및 한 개의 아민화합물과 혼합물속에서 수소로 처리된 것이며, 상기의 탄화수소는 수소화반응이 진행되는 동안에 대체적으로 불활성이 되어 나중단계에 서는 반응생성물로부터 분리될 수 있는 것을 특징으로 하여 C4탄화수소유분을 액상에서 선택적으로 수소화시키는 공정.
- 제1항에 있어서, 아민화합물은 1차 또는 2차 아민인 것을 특징으로 하는 공정.
- 제1항 또는 2항에 있어서, 아민화합물의 비율은 총액상(C4유분+희석제)의 0.01 내지 10중량%인 것을 특징으로 하는 공정.
- 제3항에 있어서, 아민화합물의 비율은 총액상(C4유분+희석제)의 0.1 내지 2중량%인 것을 특징으로 하는 공정.
- 제1항 내지 4항중 어느 한항에 있어서, 불활성 탄화수소 혼합물과 아민화합물의 비율은 C4유분의 5 내지 50%중량%인 것을 특징으로 하는 공정.
- 제1항에 있어서, 아민화합물은 메틸아민, 에틸아민, 디에틸아민, 트리에틸아민, 피페리딘, 모르폴린, 피페라진, 에틸렌디아민, 디에틸렌트리아민, 1, 3-프로파놀아민, 에타놀아민, 디에타놀아민, 비스(아미노에틸)에테르, 아닐린, 부틸아민등으로 이루어진 그룹으로부터 선택되어지는 것을 특징으로 하는 공정.
- 제1항 내지 6항중 어느 한항에 있어서, 촉매는 표면적이 5 내지 100㎡/g인 알루미나에 0.01 내지 1중량%의 팔라듐이 포함되어 있는 것을 특징으로 하는 공정.
- 제1항 내지 7항중 어느 한항에 있어서, 촉매는 0.01 내지 1중량%의 금을 포함하는 것을 특징으로 하는 공정.
- 제1항 내지 8항 중 어느 한항에 있어서, 촉매의 부피 및 시간에 대한 C4유분의 부피공급속도는 0.5-30, 온도는 20 내지 190℃, 총압력은 5 내지 50바(bars)이며 아세틸렌계 탄화수소에 대한 수소의 몰비가 1 내지 10인 작용조건을 갖는 것을 특징으로 하는 공정.
- 제9항에 있어서, 부피흐름속도는 1 내지 10이고 아세틸렌계 탄화수소에 대한 수소의 몰비는 1 내지 2인 것을 특징으로 하는 공정.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8316943A FR2553760B1 (fr) | 1983-10-25 | 1983-10-25 | Procede d'hydrogenation selective en presence de solvant des composes acetyleniques d'une coupe d'hydrocarbures c4 riche en butadiene |
FR83/16943 | 1983-10-25 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR850003379A true KR850003379A (ko) | 1985-06-17 |
KR910008366B1 KR910008366B1 (ko) | 1991-10-12 |
Family
ID=9293468
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019840006650A KR910008366B1 (ko) | 1983-10-25 | 1984-10-25 | 유기용매 존재하에 c_4유분을 선택적으로 수소화시키는 공정 |
Country Status (9)
Country | Link |
---|---|
US (1) | US4587369A (ko) |
EP (1) | EP0151356B1 (ko) |
JP (1) | JPS60109530A (ko) |
KR (1) | KR910008366B1 (ko) |
AU (1) | AU574414B2 (ko) |
BR (1) | BR8405409A (ko) |
CA (1) | CA1221109A (ko) |
DE (1) | DE3463924D1 (ko) |
FR (1) | FR2553760B1 (ko) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2552078B1 (fr) * | 1983-09-19 | 1986-05-02 | Inst Francais Du Petrole | Procede d'hydrogenation selective de l'acetylene contenu dans un melange d'acetylene et d'ethylene |
FR2603578B1 (fr) * | 1986-09-10 | 1989-02-17 | Inst Francais Du Petrole | Procede d'hydrogenation selective du phenyl-acetylene dans une coupe riche en styrene |
US4704492A (en) * | 1986-12-24 | 1987-11-03 | Mobil Oil Corporation | Selective hydrogenation of acetylenic impurities in crude butadiene |
DE19652273A1 (de) | 1996-12-16 | 1998-06-18 | Basf Ag | Monoolefinische C¶5¶-Mononitrile, Verfahren zu ihrer Herstellung und ihre Verwendung |
EP1131289B1 (en) * | 1998-08-28 | 2006-02-08 | Reilly Industries, Inc. | Processes for preparing 2-piperidineethanol compounds |
CN1097480C (zh) * | 1999-06-25 | 2003-01-01 | 中国石油化工集团公司 | 炔烃选择加氢催化剂 |
KR100601463B1 (ko) * | 2000-02-22 | 2006-07-14 | 에스케이 주식회사 | 아세틸렌알코올의 선택적 수소화 방법 |
DE10022465A1 (de) * | 2000-05-09 | 2001-11-15 | Basf Ag | Verfahren und Vorrichtung zur Aufarbeitung eines C4-Schnitts aus der Fraktionierung von Erdöl |
DE10136488A1 (de) * | 2001-07-27 | 2003-02-06 | Basf Ag | Ni(O) enthaltendes Katalysatorsystem |
DE10150285A1 (de) * | 2001-10-12 | 2003-04-17 | Basf Ag | Phosphonite |
AR036636A1 (es) * | 2001-10-12 | 2004-09-22 | Basf Ag | Fosfonita i, su uso como ligando en complejos de metal de transicion, dichos complejos, procedimiento para la obtencion de estos ultimos, uso de complejos de metal transitorio como catalizador y procedimientos para la adicion de acido cianhidrico a un doble enlace olefinico y para la isomerizacion d |
DE10150286A1 (de) * | 2001-10-12 | 2003-04-17 | Basf Ag | Phosphinite |
DE10150556A1 (de) | 2001-10-15 | 2003-04-17 | Basf Ag | Verfahren zur katalytischen Hydrierung |
DE10350999A1 (de) * | 2003-10-30 | 2005-06-02 | Basf Ag | Katalysator, umfassend wenigstens einen Nickel(O)Komplex stabilisiert durch einen sterisch anspruchsvollen Chelatphosphinitphosphitliganden, sowie ein Verfahren zur Herstellung von Nitrilen |
CN102285860B (zh) * | 2010-06-18 | 2013-11-06 | 中国石油化工股份有限公司 | 一种高炔烃含量c4物流的选择加氢工艺 |
JP5763756B2 (ja) * | 2011-05-19 | 2015-08-12 | 旭化成ケミカルズ株式会社 | 共役ジオレフィンの製造方法及び製造装置 |
CN102911714B (zh) * | 2011-08-01 | 2014-06-25 | 中国石油化工股份有限公司 | 乙烯裂解副产物c5馏分选择性加氢方法 |
CN103304360B (zh) * | 2012-03-15 | 2015-01-14 | 清华大学 | 丁二烯制品及其制备方法 |
US9957211B2 (en) | 2014-05-07 | 2018-05-01 | Sabic Global Technologies B.V. | Methods and systems for separating C4 crude streams |
US11905241B2 (en) * | 2020-12-22 | 2024-02-20 | Kellogg Brown & Root Llc | Recovery of light olefins from dry hydrocarbon gas from refinery and petrochemical production processes for production of alkylate |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2970177A (en) * | 1956-11-06 | 1961-01-31 | Phillips Petroleum Co | Olefin recovery process |
BE564339A (ko) * | 1957-02-05 | 1900-01-01 | ||
US2913405A (en) * | 1957-08-27 | 1959-11-17 | Houdry Process Corp | Desulfurization of olefinic gasoline |
GB899653A (en) * | 1958-07-25 | 1962-06-27 | British Petroleum Co | Improvements relating to the hydrogenation of gasolines |
GB865299A (en) * | 1958-12-10 | 1961-04-12 | Exxon Research Engineering Co | Purification of mono-olefins by selective hydrogenation |
NL262671A (ko) * | 1961-03-22 | |||
US3654132A (en) * | 1969-12-19 | 1972-04-04 | Gulf Research Development Co | Hydrogenation process in presence of a high boiling diluent |
FR2077907A1 (ko) * | 1970-02-23 | 1971-11-05 | Inst Francais Du Petrole | |
US3654129A (en) * | 1970-04-20 | 1972-04-04 | Universal Oil Prod Co | Hydrorefining of coke-forming hydrocarbon distillates |
US3670041A (en) * | 1970-06-10 | 1972-06-13 | Monsanto Co | Hydrogenation process |
GB1361940A (en) * | 1972-10-11 | 1974-07-30 | Sterlitamaxky O Promy Z Proizv | Process for purifying diene hydrocarbons from acetylene hydroc arbon contaminants |
IT1038403B (it) * | 1975-05-23 | 1979-11-20 | Snam Progetti | Procedimento di idrogenazione selettiva in fase gassosa di composti plurinsaturi |
US4216078A (en) * | 1976-05-17 | 1980-08-05 | Exxon Research & Engineering Co. | Hydrogenation of petroleum liquids using quinone catalysts |
FR2421858A1 (fr) * | 1978-04-05 | 1979-11-02 | Inst Francais Du Petrole | Procede d'hydrogenation selective d'une fraction d'hydrocarbures renfermant au moins un hydrocarbure diolefinique et au moins un hydrocarbure acetylenique |
DE3374666D1 (en) * | 1983-03-08 | 1988-01-07 | Dow Chemical Co | Catalyst for selective hydrogenation of alkynes in the presence of dienes |
US4447556A (en) * | 1983-04-04 | 1984-05-08 | Uop Inc. | Hydrocarbon conversion catalyst and use thereof |
FR2552078B1 (fr) * | 1983-09-19 | 1986-05-02 | Inst Francais Du Petrole | Procede d'hydrogenation selective de l'acetylene contenu dans un melange d'acetylene et d'ethylene |
-
1983
- 1983-10-25 FR FR8316943A patent/FR2553760B1/fr not_active Expired
-
1984
- 1984-10-23 EP EP84402130A patent/EP0151356B1/fr not_active Expired
- 1984-10-23 CA CA000466133A patent/CA1221109A/fr not_active Expired
- 1984-10-23 DE DE8484402130T patent/DE3463924D1/de not_active Expired
- 1984-10-24 BR BR8405409A patent/BR8405409A/pt not_active IP Right Cessation
- 1984-10-25 US US06/664,654 patent/US4587369A/en not_active Expired - Lifetime
- 1984-10-25 JP JP59225628A patent/JPS60109530A/ja active Granted
- 1984-10-25 KR KR1019840006650A patent/KR910008366B1/ko not_active IP Right Cessation
- 1984-12-13 AU AU36612/84A patent/AU574414B2/en not_active Ceased
Also Published As
Publication number | Publication date |
---|---|
JPS60109530A (ja) | 1985-06-15 |
US4587369A (en) | 1986-05-06 |
EP0151356B1 (fr) | 1987-05-27 |
AU3661284A (en) | 1986-06-19 |
CA1221109A (fr) | 1987-04-28 |
FR2553760B1 (fr) | 1986-05-02 |
EP0151356A1 (fr) | 1985-08-14 |
FR2553760A1 (fr) | 1985-04-26 |
JPH0424333B2 (ko) | 1992-04-24 |
DE3463924D1 (en) | 1987-07-02 |
BR8405409A (pt) | 1985-09-03 |
AU574414B2 (en) | 1988-07-07 |
KR910008366B1 (ko) | 1991-10-12 |
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