US3758607A - Inhibitors for olefin complexing process - Google Patents
Inhibitors for olefin complexing process Download PDFInfo
- Publication number
- US3758607A US3758607A US00259219A US3758607DA US3758607A US 3758607 A US3758607 A US 3758607A US 00259219 A US00259219 A US 00259219A US 3758607D A US3758607D A US 3758607DA US 3758607 A US3758607 A US 3758607A
- Authority
- US
- United States
- Prior art keywords
- carbon atoms
- group
- radicals
- nitrogen base
- organic nitrogen
- 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.)
- Expired - Lifetime
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- 238000000034 method Methods 0.000 title claims abstract description 31
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 21
- 230000000536 complexating effect Effects 0.000 title claims abstract description 20
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title abstract description 15
- 239000003112 inhibitor Substances 0.000 title description 4
- 125000001477 organic nitrogen group Chemical group 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- -1 alkylaryl amine Chemical group 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 22
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 13
- 239000005977 Ethylene Substances 0.000 claims description 13
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 12
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 claims description 10
- UWKQJZCTQGMHKD-UHFFFAOYSA-N 2,6-di-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=N1 UWKQJZCTQGMHKD-UHFFFAOYSA-N 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 150000003222 pyridines Chemical class 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 150000003973 alkyl amines Chemical class 0.000 claims description 5
- 239000002594 sorbent Substances 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- IFXORIIYQORRMJ-UHFFFAOYSA-N tribenzylphosphane Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)CC1=CC=CC=C1 IFXORIIYQORRMJ-UHFFFAOYSA-N 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 claims description 2
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 claims description 2
- AZUFGGNZBIWWQA-UHFFFAOYSA-N n,n,2,6-tetraethylaniline Chemical compound CCN(CC)C1=C(CC)C=CC=C1CC AZUFGGNZBIWWQA-UHFFFAOYSA-N 0.000 claims 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims 1
- 238000007086 side reaction Methods 0.000 abstract description 9
- 150000007517 lewis acids Chemical class 0.000 abstract description 8
- 239000002841 Lewis acid Substances 0.000 abstract description 6
- 125000000129 anionic group Chemical group 0.000 abstract description 3
- 239000003849 aromatic solvent Substances 0.000 abstract description 3
- 150000003003 phosphines Chemical class 0.000 abstract description 3
- 230000029936 alkylation Effects 0.000 description 22
- 238000005804 alkylation reaction Methods 0.000 description 22
- 239000000654 additive Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 10
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 9
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 7
- 239000010949 copper Substances 0.000 description 7
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 150000003378 silver Chemical class 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- NPDIDUXTRAITDE-UHFFFAOYSA-N 1-methyl-3-phenylbenzene Chemical group CC1=CC=CC(C=2C=CC=CC=2)=C1 NPDIDUXTRAITDE-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical group CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- ALLIZEAXNXSFGD-UHFFFAOYSA-N 1-methyl-2-phenylbenzene Chemical group CC1=CC=CC=C1C1=CC=CC=C1 ALLIZEAXNXSFGD-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000074 antimony hydride Inorganic materials 0.000 description 1
- RQBJDYBQTYEVEG-UHFFFAOYSA-N benzylphosphane Chemical class PCC1=CC=CC=C1 RQBJDYBQTYEVEG-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
Classifications
-
- 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
- C07C7/152—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by forming adducts or complexes
- C07C7/156—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by forming adducts or complexes with solutions of copper salts
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S585/00—Chemistry of hydrocarbon compounds
- Y10S585/949—Miscellaneous considerations
- Y10S585/952—Reaction stopping or retarding
Definitions
- the rate of alkylation in the above-described systems can be substantially reduced by adding to the c'omplexing solutions, in effective amounts, phosphine materials in combination with organic nitrogen base compounds. It is believed that the alkylation rates may be reduced in the above manner because of the neutralization of the proton donor material, which is typically l-lCl, and that such neutralization by the organic, nitrogen'bases can occur even in the presence of the Lewis acid moieties such as AlCl,, BF, and the like.
- phosphine material is believed to add stability to the overall system and allow this neutralization to occur and thereby provide long range stability for the system at a better level than the organic nitrogen additive ent invention
- moieties such as trialkyl phosphines, alkylaryl phosphines, aralkyl phosphines, benzyl phosphines and materials having the general formula R,R,R,P wherein R R, and R, are monovalent radicals independently selected from the group consisting of alkyl radicals having from one to 20 carbon atoms, preferably from two to 10 carbon atoms; phenyl radicals, alkylaryl radicals having from seven to 12 carbon atoms; preferably from seven to l0 carbon atoms; aralkyl radicals having from seven to 12 carbon atoms, preferably from from seven to 10 carbon atoms.
- useful phosphine materials include triphenyl phosphine, trioctyl phosphine, tribenzyl phosphine and tritolyl phosphine.
- organic nitrogen bases useful in the present invention are generally defined as aprotic and lack other polar functional groups, they include classes of compounds known as substituted pyridines, tertiary alkyl amines, and tertiary alkylaryl amines.
- substituted pyridines is meant any alkylated pyridine having the general formula:
- a -A are monovalent radicals independently selected from the group consisting of hydrogen radicals and alkyl groups whose total number of carbon atoms ranges from-one to 18.
- the termsubstituted pyridine includes moieties such as 2, 4-, 6-trimethyl pyridine, 2,6-ditertiary butyl pyridine, 2-methyl pyridine and the like.
- tertiary alkyl amines compounds havingthe general formula, RR'R"N wherein R, R' and R" are independently selected from the group consistingtof alkyl radicals having from one to 10 carbon atoms,-preferably from one-to five carbon atoms and having at least six carbon atoms per nitrogen;
- tertiary alkylaryl amines are materials represented by the generalformula ArRR'N wherein Ar is a substituted aryl group having at least six carbon atoms and R and R have the above designated meanings.
- minor amounts is meant from 0.1 to 15 percent, preferably from 0.5 to 10 percent based on-the number of moles of the complexing salt employed. Minor amounts of these additives are used to avoid excessive loss of complexing capacity of thecomplexing salt and moreoversince minor amounts of said additives provide sufficient stability bylowering alkylation side reactions to a minimum. 1 I
- the complexing solution may be generally described as low volatility aromatic solvents-containing cuprous or silver complexing salts such as CuPF CuBR, CuBF,Cl,.CuAlCl -CuAlBr CuTaF. and CuAlCl,Br, where x y 4.
- aromatic solvents-containing cuprous or silver complexing salts such as CuPF CuBR, CuBF,Cl,.CuAlCl -CuAlBr CuTaF. and CuAlCl,Br, where x y 4.
- temperatures and pressures at which the present invention is operable are not critical and generally will range from about 20 to 300C., preferably from 50 to 140C., and from 0.01 to 0.5 atmospheres to about to 50 atmosphere pressure.
- EXAMPLE I 55.0g of a CuAlCl -methylbiphenyl-complex, 1.10g CuCl, 0.72g triphenylphosphine and 0.53 g 2,6-di-tert.- butylpyridine are heated to 140C. under a nitrogen atmosphere in a reaction vessel equipped with magnetic stirrer, gas inlet and outlet. The input and output of gas are monitored by means of two gas meters. Ethylene is introduced through a tube ending shortly above the liquid level and a slow purge of gas is maintained to avoid vapor locking. After the initial uptake of ethylene due to complexing by the copper salt is complete, no further consumption of gas can be observed over a period of 4% hours.
- Examples Ila an d llb clearly show that the combination of an organic phosphine and an organic nitrogen base is superior in terms of the duration of an olefin EXAMPLE III
- the rate of alkylation was measured by saturating the complex with ethylene at atmospheric pressure and maintaining it under an ethylene atmosphere in a thermostated glass vessel connected to an oil-fitted wet-test meter, in such a way that any ethylene uptake following the initial saturation would be recorded in the meter.
- the alkylation rate was expressed as millimoles of ethylene per mole of CuAlCl, per hour.
- EXAMPLE V In this example the solubility of pyridine AlCl complex is compared to that of collidine AlCl in benzene solutions. To separate CuAlCh-benzene solutions was added sufficient amounts of pyridine and collidine respectively. The precipitates formed were ana' lyzed for Cu, Al, Cl and C; the results of these analyzes are found below:
- An improved process for the separation and recovery of complexible olefins from olefin-containing feedstreams by contacting said feedstreams with an aromatic sorbent solution containing cuprous salts whose anionic components are Lewis acids wherein the improvement comprises incorporating into said aromatic sorbent solution a minor amount of an organic phosphine in combination with an organic nitrogen base material selected from the group comprising alkyl amines, tertiary alkylaryl amines and substituted pyridines, to thereby substantially reduce alkylation and polymerization side reactions and stabilize said aromatic sorbent solution.
- organic phosphine has the general formula R,R,R,P wherein R R,, and R are monovalent radicals independently selected from the group consisting of alkyl radicals having from one to carbon atoms, phenyl radicals, alkylaryl radicals having from seven to 12 carbon atoms and aralkyl radicals having from seven to l2 carbon atoms.
- organic nitrogen base material is an alkyl amine having the general phenylphosphine
- R, R, and R" are independently selected from the group consisting of alkyl radicals having from one to 10 carbon atoms.
- organicnitrogen base material is a substituted pyridine having the general formula:
- a A are monovalent radicals independently selected from the group consisting of hydrogen radicals and alkyl groups whose total number of carbon atoms ranges from one to 18.
- said organic nitrogen base material is a tertiary alkylaryl amine having the general formula ArRRN wherein Ar is a substituted aryl group having at least six carbon atoms; R, and R are independently selected from the group consisting of alkyl radicals having from one to 10 carbon atoms.
- cuprous salt is one selected from the group consisting of CuPF CuBF CuBF,,Cl, CuAlCl CuAlBr CuTaF, and CuAlCl,Br,, wherein x y are integers whose sum equals 4.
- organic nitrogen base is one selected from the group consisting of 2,4,6-trimethyl pyridine, 2,6-ditertiary butyl pyridine, 2,6-diethyl N,N-diethyl amine.
- organic phosphine is one selected from the group consisting of tritrioctylphosphine, tribenzylphosphine and t'ritolylphosphine.
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)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25921972A | 1972-06-02 | 1972-06-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3758607A true US3758607A (en) | 1973-09-11 |
Family
ID=22984045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00259219A Expired - Lifetime US3758607A (en) | 1972-06-02 | 1972-06-02 | Inhibitors for olefin complexing process |
Country Status (6)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0040916A1 (en) * | 1980-05-28 | 1981-12-02 | Tenneco Resins, Inc. | The separation of complexible ligands using alkylation inhibitors |
| EP0044655A1 (en) * | 1980-07-23 | 1982-01-27 | Tenneco Resins, Inc. | Gas separation processes using liquid sorbents containing bimetallic salt complexes and alkylation inhibitors for use therein |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4525180A (en) * | 1983-03-19 | 1985-06-25 | Hidefumi Hirai | Process for recovery of ethylene from gaseous mixture |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2444945A (en) * | 1944-12-30 | 1948-07-13 | Standard Oil Dev Co | Diolefin extraction |
| US2566136A (en) * | 1943-11-06 | 1951-08-28 | Standard Oil Dev Co | Method of removing acetylenes from diolefin mixtures |
| US2566137A (en) * | 1950-03-15 | 1951-08-28 | Standard Oil Dev Co | Removing acetylenes from hydrocarbon mixtures and improvements in the separation of butadiene and acetylenes |
| US3265751A (en) * | 1964-12-17 | 1966-08-09 | Pennsalt Chemicals Corp | Inhibiting popcorn polymer formation |
| US3412173A (en) * | 1965-01-04 | 1968-11-19 | Exxon Research Engineering Co | Acetylene removal process |
-
1972
- 1972-06-02 US US00259219A patent/US3758607A/en not_active Expired - Lifetime
-
1973
- 1973-05-30 DE DE2327599A patent/DE2327599C2/de not_active Expired
- 1973-05-31 GB GB2602473A patent/GB1420446A/en not_active Expired
- 1973-06-01 CA CA173,005A patent/CA999605A/en not_active Expired
- 1973-06-01 FR FR7320105A patent/FR2186453B1/fr not_active Expired
- 1973-06-01 JP JP6176373A patent/JPS5715565B2/ja not_active Expired
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2566136A (en) * | 1943-11-06 | 1951-08-28 | Standard Oil Dev Co | Method of removing acetylenes from diolefin mixtures |
| US2444945A (en) * | 1944-12-30 | 1948-07-13 | Standard Oil Dev Co | Diolefin extraction |
| US2566137A (en) * | 1950-03-15 | 1951-08-28 | Standard Oil Dev Co | Removing acetylenes from hydrocarbon mixtures and improvements in the separation of butadiene and acetylenes |
| US3265751A (en) * | 1964-12-17 | 1966-08-09 | Pennsalt Chemicals Corp | Inhibiting popcorn polymer formation |
| US3412173A (en) * | 1965-01-04 | 1968-11-19 | Exxon Research Engineering Co | Acetylene removal process |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0040916A1 (en) * | 1980-05-28 | 1981-12-02 | Tenneco Resins, Inc. | The separation of complexible ligands using alkylation inhibitors |
| EP0044655A1 (en) * | 1980-07-23 | 1982-01-27 | Tenneco Resins, Inc. | Gas separation processes using liquid sorbents containing bimetallic salt complexes and alkylation inhibitors for use therein |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1420446A (en) | 1976-01-07 |
| JPS4948604A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-05-11 |
| FR2186453A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-01-11 |
| DE2327599A1 (de) | 1973-12-13 |
| JPS5715565B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-03-31 |
| FR2186453B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-05-06 |
| CA999605A (en) | 1976-11-09 |
| DE2327599C2 (de) | 1982-09-30 |
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