US3793187A - Process for removing carbonyl compounds from hydrocarbons - Google Patents
Process for removing carbonyl compounds from hydrocarbons Download PDFInfo
- Publication number
- US3793187A US3793187A US00277021A US3793187DA US3793187A US 3793187 A US3793187 A US 3793187A US 00277021 A US00277021 A US 00277021A US 3793187D A US3793187D A US 3793187DA US 3793187 A US3793187 A US 3793187A
- Authority
- US
- United States
- Prior art keywords
- hydrazinium
- hydrocarbons
- carbonyl
- hydrocarbon
- percent
- 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
Links
- 238000000034 method Methods 0.000 title claims description 32
- 230000008569 process Effects 0.000 title claims description 28
- 150000002430 hydrocarbons Chemical class 0.000 title abstract description 55
- 229930195733 hydrocarbon Natural products 0.000 title abstract description 54
- 150000001728 carbonyl compounds Chemical class 0.000 title abstract description 22
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 20
- -1 hydrazinium compound Chemical class 0.000 claims abstract description 19
- 239000012535 impurity Substances 0.000 claims abstract description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 238000000605 extraction Methods 0.000 claims description 9
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 4
- ZGCHATBSUIJLRL-UHFFFAOYSA-N hydrazine sulfate Chemical compound NN.OS(O)(=O)=O ZGCHATBSUIJLRL-UHFFFAOYSA-N 0.000 claims description 3
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 35
- 239000000203 mixture Substances 0.000 abstract description 24
- 239000012071 phase Substances 0.000 abstract description 16
- 239000007788 liquid Substances 0.000 abstract description 6
- 239000008346 aqueous phase Substances 0.000 abstract description 4
- 238000000622 liquid--liquid extraction Methods 0.000 abstract description 3
- 238000000638 solvent extraction Methods 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 238000005406 washing Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 238000005336 cracking Methods 0.000 description 6
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 3
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-O hydrazinium(1+) Chemical compound [NH3+]N OAKJQQAXSVQMHS-UHFFFAOYSA-O 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
- C10G29/06—Metal salts, or metal salts deposited on a carrier
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
- C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
- C10G21/08—Inorganic compounds only
Definitions
- This invention relates to a process for separating carbonyl compounds from hydrocarbons or hydrocarbon mixtures by treating the hydrocarbons or hydrocarbon mixtures in the liquid-liquid, two-phase system with an aqueous solution of a hydrazinium compound and subsequently separating the carbonyl-free hydrocarbon phase from the aqueous phase.
- the steam cracking of light petrols is accompanied by secondary reactions which are evidently attributable to the chemical mixture also contains carbonyl compounds, especially aldehydes and ketones (hereinafter referred to as carbonyl compounds such as ethanal, propanal, acetone and others which, because of their boiling point, enter the C or C -fraction during separation of the cracking gases.
- carbonyl compounds especially aldehydes and ketones (hereinafter referred to as carbonyl compounds such as ethanal, propanal, acetone and others which, because of their boiling point, enter the C or C -fraction during separation of the cracking gases.
- the carbonyl content depends on whether the light petrol is cracked at lower or high temperatures. Normally the content varies within the range of from a few hundred to more than 1,000 ppm, based on the hydrocarbons.
- carbonyl compounds can be fored in hydrocarbons as derivatives of compounds which are formed autoxidation of unsaturated hydrocarbons.
- the carbonyl compounds cannot be separated off by distillation because it is particularly the carbonyls of low molecular weight, such as ethanal, propanal and acetone, which from azeotropes with numerous hydrocarbons, for example ethanol with 1,3-butadiene or acetone with isoprene, cyclopentadiene and piperylene, cf. Azeotropic Data, ACS Monography No. 6 Washington 1952.
- liquid hydrocarbons or hydrocarbon mixtures containing carbonyl compounds as impurities in quantities of up to about 5,000 ppm can be purified in a simple and economic manner by subjecting the hydrocarbon or the hydrocarbon mixture to a liquid-liquid extraction with an aqueous solution of a hydrazinium compound and separating the puriified hydrocarbon phase from the aqueous phase.
- FIG. 1 is a diagrammatic view of apparatus suitable for carying out the process of the invention continuously; and I FIG. 2 is a graph of four curves showing residual carbonyl content as described in Examples 2-5 herein.
- carbonyl impurities can be removed from any hydrocarbon or hydrocarbon mixture which forms two liquid phases with the aqueous hydrazinium compound solution under the conditions according to the invention, for example from saturated and unsaturated hydrocarbons, from the C and C -fraction which accumulate during the cracking of light petrol, such as butadiene, butenes pentanes, pentenes, isoamylenes, isoprene, piperylene, cyclopentadiene or from mixtures of these compounds.
- saturated and unsaturated hydrocarbons from the C and C -fraction which accumulate during the cracking of light petrol, such as butadiene, butenes pentanes, pentenes, isoamylenes, isoprene, piperylene, cyclopentadiene or from mixtures of these compounds.
- Hydrazinium compounds suitable for use in the process according to the invention include compounds of the general formula N I-I X (wherein X is a monovalent anion) which are soluble in water.
- Specific examples of such hydrazinium compounds are hydrazinium sulphate, hydrazium chloride and preferably hydrazinium hydroxide (hydrazine hydrate).
- the hydrazinium compounds are used in an aqueous solution.
- the molar ratio of the hydrazinium compound to the carbonyls should preferably amount to at least 1 l, but more preferably to within the range 3 1 TO 10 l.
- the hydrazinium compounds are dissolved in water to form a 0.5 to 10 percent by weight solution and preferably a l to 5 by weight solution.
- the extraction temperatures can be varied within a relatively wide range, the lower limit being determined by the freezing point of the washing solution.
- the upper limit to the temperature range is imposed solely by the requirement that two liquid phases should exist alongside one another. In other words the temperature range rises with increased pressure.
- the reaction is carried out at a temperature in the range of from 5 to 50C under a pressure of from 0.5 to 5 bars, and preferably at a temperature of from 10 to 30C under normal pressure.
- a single wash with a hydrazine hydrate solution is sufficient to reduce the carbonyl content from up to several thousand ppm to considerably below ppm, based on the hydrocarbon or the hydrocarbon mixture.
- a simple subsequent wash with water is required to remove traces of hydrazinium compound dissolved in the hydrocarbons to below the detection limit.
- the process according to the invention can be used for purifying hydrocarbons by intensively contacting in a container a bath of the hydrocarbon or hydrocarbon mixture to be purified with the washing solution and, thereafter, optionally washing the hydrocarbon phase with water to remove traces of dissolved hydrazinium compound following phase separation.
- the process is carried out continuously.
- any type of conventional mixer-separators can be used for intermixing the two liquid phases and for subsequently separating them again.
- the hydrocarbons purified by the process according to the invention are washed with water and then further processed.
- washing with water can take the form of, for example, a countercurrent wash.
- the continuous procedure enables the hydrazinium compound in the washing solution to be maintained in the required concentration to remove the carbonyl compounds by in the lower part of the mixing apparatus 6.
- the intensively mixed liquid streams from the feed pipe 5 and the upper part of the mixing apparatus are guided into the lateral pipe 11 of the mixing apparatus 6.
- the mixed phase flows through the lateral pipe through a packed layer into the upper part of the mixing apparatus. From there, part of the mixed phase flows through a pipe 8 into a settling chamber 9, whilst the rest of the mixed phase is drawn downwards into the mixing pump 7 back to the mixing zone.
- the upper part of the settling chamber 9 is filled with a packing to promote phase separation.
- the purified hydrocarbon phase separated off is optionally washed by being delivered via a pipe 10 in countercurrent to a stream of water.
- the lower part of the settling chamber 9 acts as a reservoir for the recycled aqueous solution of the hydrazinium compound. This solution is again delivered to the mixing apparatus through a pipe 3 and can be replaced at any point by removing a fraction and introducing fresh solution.
- the process according to the invention has a number of advantages. For example, it enables reaction conditions such as temperature and pressure, under which the washing is carried out to be adapted to particular requirements.
- the starting material can be directly subjected to the process according to the invention in the liquid phase in an economically favourable manner.
- Another advantage is that the process of the invention functions without any loss of hydrocarbons because the hydrocarbons themselves do not react or are not prompted to react, for example to polymerise, with the substances of the washing solution.
- EXAMPLE 1 Three-hundred ml of a hydrocarbon mixture of which substantially'90% by weight consisted of cisand trans-1,3-pentadiene and substantially 10 percent by weight of other C -paraffins, -olefins, -diolefins and -acetylenes, was treated with aqueous hydrazinium hydroxide solution in accordance with Table l in a vessel mounted on a vibration machine.
- the hydrocarbon mixture had an initial carbonyl content of 2,100 ppm.
- the residual contents of carbonyl compounds in the hydrocarbon batches treated and the level of reduction (content of carbonyl compounds in the starting material/carbonyl compounds in the purified mixture), are shown in Table 1.
- the contents of carbonyl compounds were determined with hydroxylamine hydrochloride in accordance with an ASTM method, and are based on ethanal.
- the mixed phase was delivered from the upper part of the mixing apparatus through the pipe 8 into a settling chamber 9, the lower part of which acted as a reservoir for the washing solution.
- the clear hydrocarbon phase was run off from the upper part of the settling chamber through pipe 10 and subjected to a countercurrent wash.
- the hydrazinium hydroxide solution (1,300 ml in the system) was recycled.
- curve 1 shows the residual carbonyl content in the hydrocarbon mixture in dependence upon the throughput.
- the hydrazinium compound content of the purified hydrocarbon phase was below the detection limit of 1 ppm.
- EXAMPLE 3 As in Example 2, 500 ml/h of a hydrocarbon mixture with the same composition as in Example 1 (2,100 ppm of carbonyl compounds) were treated with 425 ml/h of a 2 percent aqueous hydrazinium hydroxide solution. The reaction conditions were the same as in Example 2. The residual carbonyl contents in the purified product are shown in FIG. 2, curve 2.
- EXAMPLE 4 One thousand ml/h of the same hydrocarbon mixture as in Example 1, except that it had a carbonyl compound content of only 181 ppm, were treated as in Example 2 with 330 ml/h of a 2 percent aqueous solution of hydrazinium hydroxide.
- FIG. 2 curve 3 shows the residual carbonyl content in the purified hydrocarbon mixture.
- EXAMPLE 5 One thousand ml/h of a C -hydrocarbon fraction of the kind obtained during the cracking of light petrol which consisted of (in percent by weight 30.9 percent of paraffins, 30.] percent of olefins, 38.2 percent of diolefins and 0.7 percent of acetylenes, and which contained 1,242 ppm of carbonyl compounds was treated as in Example 2 with 330 ml/h of a 2 percent aqueous hydrazinium hydroxide solution under normal pressure at a temperature of 20 C. Thereafter, the purified C fractions had a carbonyl content of only 50 60 ppm (see FIG. 2, curve 4).
- EXAMPLE 6 As in Example 2, 500 ml/h of 99.9 percent n-hexane which was contaminated by 1,200 ppm of acetone, were combined and treated with 425 ml/h of a 5 percent aqueous solution of hydrazinium hydroxide. It was not possible to detect any more acetone in the purified n-hexane by the method of detection described in Example 1.
- EXAMPLE 7 The process according to the invention was carried out in a continuous countercurrent extraction installation (rotating-plates system with an effective extraction zone of 3 metres) at a rotational speed of 520 rpm.
- 150 kg/h of a crude cyclopentene fraction consisting of 95 percent of cyclopentene, 3.2 percent of cyclopentane, l.8 percent of C -hydrocarbons and 423 ppm of carbonyl compounds were guided in countercurrent to 30 kg/h of a 4 percent aqeuous solution of hydrazinium hydroxide. Extraction was carried out at room temperature and normal pressure, the washing solution being dispersed in the hydrocarbon phase.
- the purified crude cyclopentene thus obtained has a residual carbonyl content of 18 ppm.
- Process for purifiying liquid hydrocarbons containing aldehydes and ketones as impurities in quantities of up to about 5,000 ppm. which comprises extracting said hydrocarbons with an aqueous solution of a hydrazinium compound having the formula N H X, wherein X is a monovalent anion, and separating the purified hydrocarbon phase.
- hydrazinium compound is selected from the group of hydrazinium sulphate, hydrazinium chloride and hydrazine hydrate.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19712141469 DE2141469C3 (de) | 1971-08-19 | Verfahren zur Entfernung von Carbonylverbindungen aus Kohlenwasserstoffen |
Publications (1)
Publication Number | Publication Date |
---|---|
US3793187A true US3793187A (en) | 1974-02-19 |
Family
ID=5817113
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00277021A Expired - Lifetime US3793187A (en) | 1971-08-19 | 1972-08-01 | Process for removing carbonyl compounds from hydrocarbons |
Country Status (6)
Country | Link |
---|---|
US (1) | US3793187A (fr) |
JP (1) | JPS5212681B2 (fr) |
BE (1) | BE787760A (fr) |
FR (1) | FR2149569B1 (fr) |
GB (1) | GB1368172A (fr) |
NL (1) | NL154484B (fr) |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4673489A (en) * | 1985-10-10 | 1987-06-16 | Betz Laboratories, Inc. | Method for prevention of fouling in a basic solution by addition of specific nitrogen compounds |
US4952301A (en) * | 1989-11-06 | 1990-08-28 | Betz Laboratories, Inc. | Method of inhibiting fouling in caustic scrubber systems |
WO1992013929A1 (fr) * | 1991-02-08 | 1992-08-20 | Ashchem I.P., Inc. | Procede inhibant la formation de salissures |
US5194143A (en) * | 1991-11-18 | 1993-03-16 | Betz Laboratories, Inc. | Method for inhibiting fouling in caustic scrubber systems |
US5220104A (en) * | 1992-06-15 | 1993-06-15 | Betz Laboratories, Inc. | Method for the prevention of fouling in a caustic solution |
US5264114A (en) * | 1991-03-25 | 1993-11-23 | Phillips Petroleum Company | Hydrocarbon treating process |
US5470457A (en) * | 1994-06-17 | 1995-11-28 | Phillips Petroleum Company | Stabilization of hydrocarbons by the addition of hydrazine |
WO2000069466A1 (fr) * | 1999-05-12 | 2000-11-23 | Kurokawa, Kiyoshi | Agent de piegeage de composes carbonyles sanguins |
EP1354863A1 (fr) * | 2002-04-18 | 2003-10-22 | Haldor Topsoe A/S | Procédé continu pour l'élimination d'eau de courants d'hydrocarbures |
US20040015032A1 (en) * | 2002-07-16 | 2004-01-22 | Ramaswamy Perumangode Neelakantan | Method for reducing foam in a primary fractionator |
US6919326B1 (en) | 1998-08-24 | 2005-07-19 | Toshio Miyata | Carbonyl-stress improving agent and peritoneal dialysate |
US20050205468A1 (en) * | 2004-02-13 | 2005-09-22 | Renaud Cadours | Method for processing a natural gas with extraction of the solvent contained in the purified natural gas |
US20050224394A1 (en) * | 2002-06-26 | 2005-10-13 | Dorf Ketal Chemicals India Pvt. Ltd. | Method of removal of carbonyl compounds along with acid gases from cracked gas in ethylene process |
US8118995B2 (en) | 2009-03-31 | 2012-02-21 | General Electric Company | Process for inhibiting fouling in hydrocarbon processing |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2926750A (en) * | 1955-09-06 | 1960-03-01 | Phillips Petroleum Co | Unsymmetrical dimethyl hydrazine as a solvent for acetylene |
US2966455A (en) * | 1957-08-14 | 1960-12-27 | Sun Oil Co | Refining hydrocarbons with hydrazines and hydrogenation catalysts |
US3308201A (en) * | 1966-03-08 | 1967-03-07 | Petro Tex Chem Corp | Purification of hydrocarbons |
-
1972
- 1972-08-01 US US00277021A patent/US3793187A/en not_active Expired - Lifetime
- 1972-08-16 GB GB3812972A patent/GB1368172A/en not_active Expired
- 1972-08-17 NL NL727211274A patent/NL154484B/xx unknown
- 1972-08-18 BE BE787760D patent/BE787760A/fr unknown
- 1972-08-18 JP JP47082217A patent/JPS5212681B2/ja not_active Expired
- 1972-08-18 FR FR7229686A patent/FR2149569B1/fr not_active Expired
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2926750A (en) * | 1955-09-06 | 1960-03-01 | Phillips Petroleum Co | Unsymmetrical dimethyl hydrazine as a solvent for acetylene |
US2966455A (en) * | 1957-08-14 | 1960-12-27 | Sun Oil Co | Refining hydrocarbons with hydrazines and hydrogenation catalysts |
US3308201A (en) * | 1966-03-08 | 1967-03-07 | Petro Tex Chem Corp | Purification of hydrocarbons |
Cited By (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4673489A (en) * | 1985-10-10 | 1987-06-16 | Betz Laboratories, Inc. | Method for prevention of fouling in a basic solution by addition of specific nitrogen compounds |
US4952301A (en) * | 1989-11-06 | 1990-08-28 | Betz Laboratories, Inc. | Method of inhibiting fouling in caustic scrubber systems |
US5213678A (en) * | 1991-02-08 | 1993-05-25 | Ashchem I.P., Inc. | Method for inhibiting foulant formation in organic streams using erythorbic acid or oximes |
AU650213B2 (en) * | 1991-02-08 | 1994-06-09 | Ashchem I.P., Inc. | Method for inhibiting foulant formation |
WO1992013929A1 (fr) * | 1991-02-08 | 1992-08-20 | Ashchem I.P., Inc. | Procede inhibant la formation de salissures |
US5264114A (en) * | 1991-03-25 | 1993-11-23 | Phillips Petroleum Company | Hydrocarbon treating process |
US5194143A (en) * | 1991-11-18 | 1993-03-16 | Betz Laboratories, Inc. | Method for inhibiting fouling in caustic scrubber systems |
US5220104A (en) * | 1992-06-15 | 1993-06-15 | Betz Laboratories, Inc. | Method for the prevention of fouling in a caustic solution |
US5470457A (en) * | 1994-06-17 | 1995-11-28 | Phillips Petroleum Company | Stabilization of hydrocarbons by the addition of hydrazine |
US5672793A (en) * | 1994-06-17 | 1997-09-30 | Phillips Petroleum Company | Stabilization of hydrocarbons by the addition of hydrazine |
US7745613B2 (en) | 1998-08-24 | 2010-06-29 | Toshio Miyata | Method for preparing peritoneal dialysate |
US20050267045A1 (en) * | 1998-08-24 | 2005-12-01 | Toshio Miyata | Method for preparing peritoneal dialysate |
US7297689B2 (en) | 1998-08-24 | 2007-11-20 | Kiyoshi Kurokawa | Method for preparing peritoneal dialysate |
US6919326B1 (en) | 1998-08-24 | 2005-07-19 | Toshio Miyata | Carbonyl-stress improving agent and peritoneal dialysate |
US20070020341A1 (en) * | 1998-08-24 | 2007-01-25 | Toshio Miyata; Kiyoshi Kurokawa; And Tokai University Educational System | Method for preparing peritoneal dialysate |
WO2000069466A1 (fr) * | 1999-05-12 | 2000-11-23 | Kurokawa, Kiyoshi | Agent de piegeage de composes carbonyles sanguins |
US20030199723A1 (en) * | 2002-04-18 | 2003-10-23 | Hommeltoft Sven Ivar | Continuous process for the removal of water from a hydrocarbon stream |
US7077950B2 (en) | 2002-04-18 | 2006-07-18 | Haldor Topsoe A/S | Continuous process for the removal of water from a hydrocarbon stream |
EP1354863A1 (fr) * | 2002-04-18 | 2003-10-22 | Haldor Topsoe A/S | Procédé continu pour l'élimination d'eau de courants d'hydrocarbures |
US20050224394A1 (en) * | 2002-06-26 | 2005-10-13 | Dorf Ketal Chemicals India Pvt. Ltd. | Method of removal of carbonyl compounds along with acid gases from cracked gas in ethylene process |
US7575669B2 (en) | 2002-06-26 | 2009-08-18 | Dorf Ketal Chemicals, Llc | Method of removal of carbonyl compounds along with acid gases from cracked gas in ethylene process |
US20040015032A1 (en) * | 2002-07-16 | 2004-01-22 | Ramaswamy Perumangode Neelakantan | Method for reducing foam in a primary fractionator |
US7906012B2 (en) | 2002-07-16 | 2011-03-15 | Dorf Ketal Chemicals India Pvt. Ltd. | Method for reducing foam in a primary fractionator |
US20050205468A1 (en) * | 2004-02-13 | 2005-09-22 | Renaud Cadours | Method for processing a natural gas with extraction of the solvent contained in the purified natural gas |
US7470829B2 (en) * | 2004-02-13 | 2008-12-30 | Institut Francais Du Petrole | Method for processing a natural gas with extraction of the solvent contained in the purified natural gas |
US8118995B2 (en) | 2009-03-31 | 2012-02-21 | General Electric Company | Process for inhibiting fouling in hydrocarbon processing |
Also Published As
Publication number | Publication date |
---|---|
FR2149569B1 (fr) | 1976-08-13 |
FR2149569A1 (fr) | 1973-03-30 |
NL154484B (nl) | 1977-09-15 |
GB1368172A (en) | 1974-09-25 |
JPS4829702A (fr) | 1973-04-19 |
NL7211274A (fr) | 1973-02-21 |
BE787760A (fr) | 1973-02-19 |
JPS5212681B2 (fr) | 1977-04-08 |
DE2141469A1 (de) | 1973-02-22 |
DE2141469B2 (de) | 1976-08-26 |
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