FR2504123A1 - Procede de production de nonenes ou de production simultanee de nonenes et de dodecenes a partir de propene - Google Patents
Procede de production de nonenes ou de production simultanee de nonenes et de dodecenes a partir de propene Download PDFInfo
- Publication number
- FR2504123A1 FR2504123A1 FR8108077A FR8108077A FR2504123A1 FR 2504123 A1 FR2504123 A1 FR 2504123A1 FR 8108077 A FR8108077 A FR 8108077A FR 8108077 A FR8108077 A FR 8108077A FR 2504123 A1 FR2504123 A1 FR 2504123A1
- Authority
- FR
- France
- Prior art keywords
- nonenes
- catalyst
- reaction
- hexenes
- liquid phase
- 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.)
- Granted
Links
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- -1 ALUMINUM COMPOUND Chemical class 0.000 claims abstract description 7
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 16
- 150000001336 alkenes Chemical class 0.000 claims description 11
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 10
- 229910052759 nickel Inorganic materials 0.000 claims description 9
- 239000012071 phase Substances 0.000 claims description 9
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000006471 dimerization reaction Methods 0.000 claims description 6
- 239000012295 chemical reaction liquid Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 abstract description 3
- 150000002816 nickel compounds Chemical class 0.000 abstract description 3
- 238000004513 sizing Methods 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000005234 alkyl aluminium group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JTXAHXNXKFGXIT-UHFFFAOYSA-N propane;prop-1-ene Chemical group CCC.CC=C JTXAHXNXKFGXIT-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- HOMQMIYUSVQSHM-UHFFFAOYSA-N cycloocta-1,3-diene;nickel Chemical compound [Ni].C1CCC=CC=CC1.C1CCC=CC=CC1 HOMQMIYUSVQSHM-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- GJTGYNPBJNRYKI-UHFFFAOYSA-N hex-1-ene;prop-1-ene Chemical compound CC=C.CCCCC=C GJTGYNPBJNRYKI-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- DVTHIMLUHWEZOM-UHFFFAOYSA-L nickel(2+);octanoate Chemical compound [Ni+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O DVTHIMLUHWEZOM-UHFFFAOYSA-L 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- WHFQAROQMWLMEY-UHFFFAOYSA-N propylene dimer Chemical group CC=C.CC=C WHFQAROQMWLMEY-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/30—Catalytic processes with hydrides or organic compounds containing metal-to-carbon bond; Metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8108077A FR2504123A1 (fr) | 1981-04-21 | 1981-04-21 | Procede de production de nonenes ou de production simultanee de nonenes et de dodecenes a partir de propene |
| DE19823213940 DE3213940A1 (de) | 1981-04-21 | 1982-04-16 | Verfahren zur herstellung von nonenen oder zur gleichzeitigen herstellung von nonenen und dodecenen aus propen |
| GB8211364A GB2097016B (en) | 1981-04-21 | 1982-04-20 | Process for producing nonenes or for simultaneously producing nonenes and dodecenes from propene |
| JP57068005A JPS57181022A (en) | 1981-04-21 | 1982-04-21 | Manufacture of nonene or mixture of nonene and dodecene |
| US06/370,322 US4404415A (en) | 1981-04-21 | 1982-04-21 | Process for producing nonenes or for simultaneously producing nonenes and dodecenes from propene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8108077A FR2504123A1 (fr) | 1981-04-21 | 1981-04-21 | Procede de production de nonenes ou de production simultanee de nonenes et de dodecenes a partir de propene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2504123A1 true FR2504123A1 (fr) | 1982-10-22 |
| FR2504123B1 FR2504123B1 (enExample) | 1984-08-17 |
Family
ID=9257692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8108077A Granted FR2504123A1 (fr) | 1981-04-21 | 1981-04-21 | Procede de production de nonenes ou de production simultanee de nonenes et de dodecenes a partir de propene |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4404415A (enExample) |
| JP (1) | JPS57181022A (enExample) |
| DE (1) | DE3213940A1 (enExample) |
| FR (1) | FR2504123A1 (enExample) |
| GB (1) | GB2097016B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4615790A (en) * | 1985-10-28 | 1986-10-07 | Shell Oil Company | Preparation of synthetic hydrocarbon lubricants |
| US5196624A (en) * | 1990-04-27 | 1993-03-23 | Chevron Research And Technology Company | Detergent grade to C10 to C28 olefins, (C10 to C28 alkyl)benzenes and C10 to C28 alkyl) benzene sulfonates and process for preparing same using a phosphine containing catalyst |
| US5196625A (en) * | 1990-04-27 | 1993-03-23 | Chevron Research & Technology Company | Detergent grade to C10 to C28 olefins, (C10 to C28 alkyl) benzenes and (C10 to C28 alkyl) benzene sulfonates and process for preparing same using a phosphite containing catalyst |
| US6281401B1 (en) * | 1999-09-16 | 2001-08-28 | Phillips Petroleum Company | Oligomerization of olefins |
| US8440871B2 (en) | 2010-03-30 | 2013-05-14 | Uop Llc | Tetramer production apparatus and process relating thereto |
| CN113426196B (zh) * | 2021-07-06 | 2022-12-27 | 大庆中蓝石化有限公司 | 壬烯生产装置高压设备切液回收系统 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB474831A (en) * | 1936-04-04 | 1937-11-04 | Ig Farbenindustrie Ag | Improvements in or relating to the polymerisation of olefines |
| DE961801C (de) * | 1947-01-29 | 1957-04-11 | Universal Oil Prod Co | Verfahren zur Herstellung fluessiger Polymere aus monomeren Olefinen |
| FR1337354A (fr) * | 1962-07-24 | 1963-09-13 | Shell Int Research | Procédé de polymérisation du propène |
| FR1385503A (fr) * | 1962-11-30 | 1965-01-15 | Shell Int Research | Procédé de dimérisation de mono-oléfines |
| US3592869A (en) * | 1968-10-03 | 1971-07-13 | Shell Oil Co | Olefin oligomerization |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3592896A (en) * | 1964-01-27 | 1971-07-13 | Chemagro Corp | Sulfoxide containing pesticides |
| FR2421159A1 (fr) * | 1978-03-28 | 1979-10-26 | Inst Francais Du Petrole | Procede de production d'oligomeres du propene et/ou du butene |
| FR2443877A1 (fr) * | 1978-12-11 | 1980-07-11 | Inst Francais Du Petrole | Nouvelle composition catalytique et sa mise en oeuvre pour l'oligomerisation des olefines |
-
1981
- 1981-04-21 FR FR8108077A patent/FR2504123A1/fr active Granted
-
1982
- 1982-04-16 DE DE19823213940 patent/DE3213940A1/de not_active Withdrawn
- 1982-04-20 GB GB8211364A patent/GB2097016B/en not_active Expired
- 1982-04-21 JP JP57068005A patent/JPS57181022A/ja active Granted
- 1982-04-21 US US06/370,322 patent/US4404415A/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB474831A (en) * | 1936-04-04 | 1937-11-04 | Ig Farbenindustrie Ag | Improvements in or relating to the polymerisation of olefines |
| DE961801C (de) * | 1947-01-29 | 1957-04-11 | Universal Oil Prod Co | Verfahren zur Herstellung fluessiger Polymere aus monomeren Olefinen |
| FR1337354A (fr) * | 1962-07-24 | 1963-09-13 | Shell Int Research | Procédé de polymérisation du propène |
| FR1385503A (fr) * | 1962-11-30 | 1965-01-15 | Shell Int Research | Procédé de dimérisation de mono-oléfines |
| US3592869A (en) * | 1968-10-03 | 1971-07-13 | Shell Oil Co | Olefin oligomerization |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3213940A1 (de) | 1982-11-25 |
| JPS57181022A (en) | 1982-11-08 |
| JPH027294B2 (enExample) | 1990-02-16 |
| GB2097016A (en) | 1982-10-27 |
| GB2097016B (en) | 1984-03-21 |
| FR2504123B1 (enExample) | 1984-08-17 |
| US4404415A (en) | 1983-09-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |