WO2018207657A1 - 含硫黄化合物除去装置および含硫黄化合物除去方法 - Google Patents
含硫黄化合物除去装置および含硫黄化合物除去方法 Download PDFInfo
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- WO2018207657A1 WO2018207657A1 PCT/JP2018/017143 JP2018017143W WO2018207657A1 WO 2018207657 A1 WO2018207657 A1 WO 2018207657A1 JP 2018017143 W JP2018017143 W JP 2018017143W WO 2018207657 A1 WO2018207657 A1 WO 2018207657A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/11—Purification; Separation; Use of additives by absorption, i.e. purification or separation of gaseous hydrocarbons with the aid of liquids
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1456—Removing acid components
- B01D53/1468—Removing hydrogen sulfide
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1425—Regeneration of liquid absorbents
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/18—Absorbing units; Liquid distributors therefor
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- 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
- C10G29/20—Organic compounds not containing metal atoms
- C10G29/22—Organic compounds not containing metal atoms containing oxygen as the only hetero atom
- C10G29/24—Aldehydes or ketones
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
- C10L3/06—Natural gas; Synthetic natural gas obtained by processes not covered by C10G, C10K3/02 or C10K3/04
- C10L3/10—Working-up natural gas or synthetic natural gas
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
- C10L3/06—Natural gas; Synthetic natural gas obtained by processes not covered by C10G, C10K3/02 or C10K3/04
- C10L3/10—Working-up natural gas or synthetic natural gas
- C10L3/101—Removal of contaminants
- C10L3/102—Removal of contaminants of acid contaminants
- C10L3/103—Sulfur containing contaminants
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/204—Amines
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/204—Amines
- B01D2252/2041—Diamines
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/204—Amines
- B01D2252/20431—Tertiary amines
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/205—Other organic compounds not covered by B01D2252/00 - B01D2252/20494
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2258/00—Sources of waste gases
- B01D2258/02—Other waste gases
- B01D2258/0225—Other waste gases from chemical or biological warfare
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2258/00—Sources of waste gases
- B01D2258/05—Biogas
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- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/20—Characteristics of the feedstock or the products
- C10G2300/201—Impurities
- C10G2300/202—Heteroatoms content, i.e. S, N, O, P
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- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/20—Characteristics of the feedstock or the products
- C10G2300/201—Impurities
- C10G2300/207—Acid gases, e.g. H2S, COS, SO2, HCN
Definitions
- the present invention relates to a sulfur-containing compound removing device and a sulfur-containing compound removing method.
- Patent Document 1 A method using a metal oxide (Patent Document 1), a method using a low molecular weight aldehyde such as formalin and glyoxal provided as an aqueous solution (Patent Document 2), a method using a reversible absorbent such as triethanolamine, and the like are known. (Patent Document 3).
- the method using a metal oxide is regarded as a problem that waste derived from the metal oxide is generated.
- the method using a low molecular weight aldehyde has a problem of compatibility with a fluid to be treated, a problem of wastewater treatment, and the like.
- the method using a reversible absorbent requires heating to regenerate the absorbent and requires a separate processing device for treating hydrogen sulfide desorbed from the absorbent. There are problems such as excessive plant construction costs.
- Patent Documents 4 and 5 As a method for efficiently removing hydrogen sulfide, a method using an oil-soluble hydrogen sulfide removing agent has also been proposed (Patent Documents 4 and 5).
- an object of the present invention is to provide a sulfur-containing compound removing apparatus capable of reducing utilities and waste required for processing when removing a sulfur-containing compound contained in a gas, and a sulfur-containing compound removing method using the same. There is.
- the present inventors have conducted mixing in which a sulfur-containing compound absorbed agent in which a sulfur-containing compound in a gas to be treated is absorbed in a sulfur-containing compound absorbent and a nonaqueous liquid are mixed in a sulfur-containing compound removing device. It has been found that the above object can be achieved by providing a portion.
- the present invention relates to the following [1] to [5].
- a sulfur-containing compound removing unit that removes the sulfur-containing compound by bringing a gas to be treated containing the sulfur-containing compound into contact with an oil-soluble sulfur-containing compound absorbent;
- a mixing unit for mixing the sulfur-containing compound absorbed agent and the non-aqueous liquid in which the sulfur-containing compound is absorbed in the sulfur-containing compound absorbent;
- a sulfur-containing compound removing device A sulfur-containing compound removing apparatus according to [1], wherein the non-aqueous liquid contains a hydrocarbon.
- the sulfur-containing compound removing apparatus according to [1] or [2], wherein the non-aqueous liquid is a liquid generated when crude oil or natural gas is mined.
- the sulfur-containing compound removing apparatus according to any one of [1] to [3], wherein the gas to be treated is a hydrocarbon that is a gas at normal temperature.
- a method for removing a sulfur-containing compound comprising a step of removing a sulfur-containing compound from a gas to be treated containing a sulfur-containing compound using the sulfur-containing compound removing apparatus according to any one of [1] to [5].
- the sulfur-containing compound removing apparatus of the present invention includes a sulfur-containing compound removing unit that removes the sulfur-containing compound by bringing a gas to be treated containing the sulfur-containing compound into contact with an oil-soluble sulfur-containing compound absorbent, and the sulfur-containing compound. And a mixing unit that mixes the sulfur-containing compound-absorbed agent in which the sulfur-containing compound is absorbed with the absorbent and the non-aqueous liquid.
- the “sulfur-containing compound” is at least one compound selected from the group consisting of compounds containing hydrogen sulfide and —SH groups. That is, it may be only hydrogen sulfide, only a compound containing a —SH group, or a mixture thereof.
- the compound containing a —SH group is not particularly limited, and examples thereof include compounds represented by the chemical formula “R—SH” and classified as mercaptans.
- R such as methyl mercaptan, ethyl mercaptan, n-propyl mercaptan, isopropyl mercaptan, n-butyl mercaptan, isobutyl mercaptan, sec-butyl mercaptan, tert-butyl mercaptan, n-amyl mercaptan is an alkyl group.
- R is an aryl group such as phenyl mercaptan; and those in which R is an aralkyl group such as benzyl mercaptan.
- the “total amount of active components of the sulfur-containing compound absorbent” means the total amount of components excluding the solvent when the sulfur-containing compound absorbent contains a solvent, and the sulfur-containing compound absorbent contains the solvent. When not included, it means the total amount of the sulfur-containing compound absorbent.
- reducing the initial amount of the sulfur-containing compound in the gas to be treated by, for example, converting the sulfur-containing compound into another compound is also included in the “removal” of the sulfur-containing compound.
- the converted product after the sulfur-containing compound is converted into another compound by the sulfur compound absorbent is discharged from the sulfur-containing compound removal unit as the sulfur-containing compound absorbed agent, and as a result, the above-mentioned in the gas to be treated The initial amount of sulfur-containing compound is reduced.
- the gas to be treated is not particularly limited as long as it is a gas in the sulfur-containing compound removing section, but is typically a hydrocarbon that is gaseous at normal temperature (for example, normal temperature and normal pressure).
- Specific examples of the gas to be treated include natural gas, petroleum gas, oil field gas, associated gas, tail gas, dimethyl ether, synthesis gas, biogas and the like.
- the gas to be treated may be only one kind or two or more kinds.
- the sulfur-containing compound absorbent is not particularly limited as long as it is oil-soluble.
- Examples of the sulfur-containing compound absorbent include monoaldehydes such as propionaldehyde, butanal, pentanal, hexanal, heptanal, octanal, nonanal, decanal and benzaldehyde; ⁇ , ⁇ -unsaturated aldehydes such as acrolein, crotonaldehyde and senecioaldehyde; 3 -Methyl glutaraldehyde, 1,6-hexane dial, ethyl pentane dial, 1,7-heptane dial, methyl hexane dial, 1,8-octane dial, methyl heptane dial, dimethyl hexane dial, ethyl Hexane dial, 1,9-nonane dial, 2-methyl-1,8-octane dial, ethy
- triamines composed of alkanolamines having 1 to 6 carbon atoms and aldehydes having 1 to 6 carbon atoms described in US Pat. No. 8,512,449, etc .; International Publication No. 2013/181056 Mixtures of metal salts and oil-soluble amines and aldehyde compounds as described in No. 1, etc .; Hydantoins as described in WO 2015/160488, etc .; Acrylonitriles as described in WO 2016/105371, etc .; 2017/044248, International Publication No. 2017/044250, etc. Hemiformals and hemiacetals described in the above; compositions containing acetic anhydride and triacetamide as described in US Pat. No.
- a sulfur-containing compound absorbent may be used alone or in combination of two or more.
- At least one compound selected from the group consisting of ⁇ , ⁇ -unsaturated aldehydes and dialdehydes is preferable from the viewpoint of sulfur-containing compound absorption efficiency, and ⁇ , ⁇ -unsaturated aldehydes and carbons having 3 to 10 carbon atoms are preferred. More preferable is at least one compound selected from the group consisting of several to 20 dialdehydes, and acrolein, senesioaldehyde, 3-methylglutaraldehyde, 1,9-nonanedial and 2-methyl-1,8-octanedial.
- More preferable is at least one compound selected from the group consisting of: senecioaldehyde, 1,9-nonanedial and 2-, from the viewpoints of low toxicity, biodegradability, handling safety, heat resistance, low metal corrosivity, and the like.
- One compound is preferred.
- the total amount of ⁇ , ⁇ -unsaturated aldehyde and dialdehyde in the sulfur-containing compound absorbent is preferably 5% by mass or more, more preferably 10% by mass or more, and still more preferably from the viewpoint of sulfur-containing compound absorption efficiency. It is 20 mass% or more. The total amount is preferably 100% by mass or less, for example, 80% by mass or less.
- the sulfur-containing compound absorbent may consist of only ⁇ , ⁇ -unsaturated aldehyde and dialdehyde.
- the content of ⁇ , ⁇ -unsaturated aldehyde in the sulfur-containing compound absorbent is preferably 5% by mass or more, more preferably 10% by mass or more, and still more preferably from the viewpoint of sulfur-containing compound absorption efficiency. It is 20 mass% or more. Moreover, the said content becomes like this. Preferably it is 100 mass% or less, for example, is 80 mass% or less.
- the sulfur-containing compound absorbent may consist of only an ⁇ , ⁇ -unsaturated aldehyde.
- the total amount of ⁇ , ⁇ -unsaturated aldehyde and dialdehyde in the total amount of active ingredients of the sulfur-containing compound absorbent is preferably 40% by mass or more, more preferably 50% by mass, from the viewpoint of sulfur-containing compound absorption efficiency. More preferably, it is 60% by mass or more. The total amount is preferably 100% by mass or less, for example, 80% by mass or less.
- the sulfur-containing compound absorbent may consist of only ⁇ , ⁇ -unsaturated aldehyde and dialdehyde.
- the content of ⁇ , ⁇ -unsaturated aldehyde in the total amount of active ingredients of the sulfur-containing compound absorbent is preferably 40% by mass or more, more preferably 50% by mass from the viewpoint of sulfur-containing compound absorption efficiency. More preferably, it is 60% by mass or more. Moreover, the said content becomes like this. Preferably it is 100 mass% or less, for example, is 80 mass% or less.
- the sulfur-containing compound absorbent may consist of only an ⁇ , ⁇ -unsaturated aldehyde.
- 1,9-nonanedial or 2-methyl-1,8-octanedial may be used alone, but from the viewpoint of industrial availability, 1,9-nonane dial and 2-methyl-1,8-octane dial are preferably used as a mixture.
- the mixing ratio of such a mixture of 1,9-nonanedial and 2-methyl-1,8-octanediar is not particularly limited, but is usually 1,9-nonanedial / 2-methyl-1,8-octanediar.
- the mass ratio is preferably 99/1 to 1/99, more preferably 95/5 to 5/95, still more preferably 93/7 to 45/55, and 90/10 to 55 / Particularly preferred is 45.
- the sulfur-containing compound absorbent may contain any organic compound as long as the effect is not impaired.
- organic compounds include polyalkylene glycols such as polyethylene glycol, polypropylene glycol, and polybutylene glycol described in International Patent Publication No. 2016/121747, polyvalent amines (1) represented by the following general formula (1), and the like. Is mentioned.
- W represents a methylene group, a dimethylene group or a trimethylene group
- R 1 to R 5 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkenyl group having 1 to 6 carbon atoms.
- n represents an integer of 0 to 3000.
- R 1 and R 2 and R 3 and R 4 may be independently connected to each other to form a ring (that is, only R 1 and R 2 are connected to each other to form a ring).
- R 3 and R 4 may be connected to each other to form a ring, or R 1 and R 2 and R 3 and R 4 may be connected to each other to form a ring).
- One or more R 6 may be substituted (wherein R 6 is an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or 6 to 6 carbon atoms).
- R 1 to R 6 may be substituted with a hydroxy group or an alkoxy group having 1 to 6 carbon atoms, and when there are a plurality of W, R 5 or R 6 , each is the same group Need not be.
- W is preferably a dimethylene group or a trimethylene group, more preferably a dimethylene group, and particularly preferably all W present in the general formula (1) is a dimethylene group.
- R 1 to R 5 are preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and further preferably a hydrogen atom or a methyl group.
- n is preferably an integer of 0 to 1000, more preferably an integer of 0 to 100, still more preferably an integer of 0 to 10, and particularly preferably an integer of 0 to 5.
- W is a methylene group, such as N, N, N ′, N′-tetramethyldiaminomethane; Ethylenediamine, 1,2-diaminopropane, 1,2-diamino-2-methylpropane, N-methylethylenediamine, N-ethylethylenediamine, N-propylethylenediamine, N-butylethylenediamine, N-benzylethylenediamine, N-phenylethylenediamine, N, N-dimethylethylenediamine, N, N-diethylethylenediamine, N, N-dipropylethylenediamine, N, N-dibutylethylenediamine, N, N'-dimethylethylenediamine, N, N'-diethylethylenediamine, N, N'- Dipropylethylenediamine, N, N'-diisopropylethylenediamine, N, N'-diisopropylethylenediamine,
- n 1, for example, Diethylenetriamine, 2,2′-diamino-N-methyldiethylamine, N, N ′, N ′′ -trimethyldiethylenetriamine, N, N, N ′, N ′′, N ′′ -pentamethyldiethylenetriamine, N, N, N ′, N
- W is a dimethylene group, such as'-tetrabutyldiethylenetriamine
- W is a trimethylene group, such as 3,3′-diaminodipropylamine and N, N-bis [3- (dimethylamino) propyl] amine.
- the polyvalent amine (1) may be used alone or in combination of two or more.
- the polyvalent amine (1) may be a commercially available product, or may be produced from a known method, for example, a reaction between ammonia and an alkyl halide.
- the sulfur-containing compound absorbent contains at least one of polyalkylene glycol and the polyvalent amine (1) represented by the general formula (1)
- the total amount of active ingredients of the sulfur-containing compound absorbent is, for example, 1 to 50% by mass, and in one embodiment, 10 to 40% by mass.
- the total amount of the polyalkylene glycol, the polyvalent amine (1) represented by the general formula (1), the ⁇ , ⁇ -unsaturated aldehyde and the dialdehyde in the total amount of the active ingredient of the sulfur-containing compound absorbent is:
- the amount is preferably 60 to 100% by mass, more preferably 80 to 100% by mass, further preferably 90 to 100% by mass, and more preferably 95 to 100% by mass.
- the total amount of the polyalkylene glycol and the polyvalent amine (1) represented by the general formula (1) is preferably 10 to 10 parts by weight based on 100 parts by weight of the total amount of the ⁇ , ⁇ -unsaturated aldehyde and the dialdehyde. It may be 100 parts by mass, more preferably 30 to 60 parts by mass.
- the sulfur-containing compound absorbent contains the polyvalent amine (1) represented by the general formula (1)
- the sulfur-containing compound absorbent is represented by the general formula (1) in the sulfur-containing compound absorbent.
- the content of the polyvalent amine (1) is, for example, 1 to 50% by mass, and in one embodiment 10 to 40% by mass.
- the content of the polyvalent amine (1) represented by the general formula (1) is preferably 10 to 100 parts by mass with respect to 100 parts by mass of the ⁇ , ⁇ -unsaturated aldehyde. Preferably, it may be 30 to 60 parts by mass.
- Sulfur-containing compound absorbents are surfactants, corrosion inhibitors, oxygen scavengers, iron control agents, flocculants, temperature stabilizers, pH adjusters, dehydration adjusters, scale inhibitors, biocides, antifoaming agents, It may further contain optional components such as a lubricant, a nitrogen-containing compound other than the polyvalent amine (1), and a solvent.
- the sulfur-containing compound removing unit that removes the sulfur-containing compound by bringing the gas to be treated containing the sulfur-containing compound into contact with the oil-soluble sulfur-containing compound absorbent is sufficiently in contact with the sulfur-containing compound absorbent.
- the sulfur-containing compound removing unit for example, a packed tower, a spray tower, a scrubber, a bubble tower, a bubble stirring tank, a static mixer, a forced vibration type bubble tower, a vertically rising thin film device, an orifice pipe type device, and the like can be employed.
- a packed tower and a bubble tower are desirable from the viewpoint of ease of device design and low required power.
- the sulfur-containing compound absorbent When using a packed tower, the sulfur-containing compound absorbent is supplied to the upper part of the tower using a supply means such as a pump and is brought into contact with the gas to be treated.
- the sulfur-containing compound absorbent that has absorbed the sulfur-containing compound and has reached the bottom of the tower (sulfur-containing compound absorbed agent) is discharged from the sulfur-containing compound removing section, and at least a part thereof is supplied to the mixing section described later.
- part of the discharged sulfur-containing compound absorbed agent is re-supplied to the sulfur-containing compound removing section through a circulating means such as a pump, and again for absorption of the sulfur-containing compound together with the unused sulfur-containing compound absorbent. May be used.
- the amount of the sulfur-containing compound absorbent used is preferably 0.1 to 5000 parts by mass, more preferably 1 to 1 part by mass of the sulfur-containing compound in the total amount of gas to be circulated. What is necessary is just to make a to-be-processed gas and a sulfur-containing compound absorber contact so that it may become -1000 mass part.
- the temperature of the sulfur-containing compound removing part is not particularly limited, but is preferably in the range of ⁇ 30 to 150 ° C., more preferably in the range of 0 to 130 ° C.
- the pressure in the sulfur-containing compound removing portion is not particularly limited, but is preferably in the range of ⁇ 0.1 to 10 MPa, more preferably 0 to 1.0 MPa.
- the mixing part for mixing the sulfur-containing compound absorbed agent and the non-aqueous liquid is not particularly limited as long as the sulfur-containing compound absorbed agent and the non-aqueous liquid are sufficiently mixed.
- the mixing unit for example, a batch type mixing device, an inline type mixing device, or the like can be adopted.
- the non-aqueous liquid is not particularly limited as long as it can dissolve the treated sulfur-containing compound absorbent, and is an aliphatic hydrocarbon such as methane, ethane, propane, butane, pentane, n-hexane, cyclohexane; benzene, toluene
- Aromatic hydrocarbons such as xylene, mesitylene, naphthalene; monoalcohols or diols such as methanol, ethanol, 2-propanol, ethylene glycol, polyethylene glycol; petroleum products such as gasoline, naphtha, light oil, heavy oil, kerosene; biodiesel; Crude oil; liquefied natural gas; liquefied petroleum gas; condensate when natural gas is mined.
- hydrocarbons such as aliphatic hydrocarbons and aromatic hydrocarbons are preferred, and more preferably at least one of aliphatic hydrocarbons having 1 to 15 carbon atoms and aromatic hydrocarbons having 6 to 18 ring carbon atoms.
- the temperature and pressure are adjusted to form a liquid and mixed. These may be used alone or in combination of two or more.
- the sulfur-containing compound removing apparatus of the present invention When the sulfur-containing compound removing apparatus of the present invention is used at a crude oil or natural gas mining site, it is necessary to use a liquid generated as a result of the mining of crude oil or natural gas as a non-aqueous liquid. It is most preferable because it is absent. Specific examples of such liquids include crude oil, liquefied natural gas, liquefied petroleum gas, and condensate during natural gas mining.
- the sulfur content contained in the sulfur-containing compound absorbed agent is processed together with other sulfur content contained in the crude oil by a sulfur content recovery device equipped in the refinery.
- the Rukoto That is, it is not necessary to construct a large-scale processing apparatus at a crude oil or natural gas mining site, and waste is minimized.
- the sulfur-containing compound removing apparatus of the present invention the utility and waste required for the treatment can be reduced by mixing the sulfur-containing compound absorbed agent with the non-aqueous liquid.
- the sulfur-containing compound removing apparatus is: A sulfur-containing compound removing unit that removes the sulfur-containing compound by bringing a gas to be treated containing the sulfur-containing compound into contact with an oil-soluble sulfur-containing compound absorbent; A mixing unit for mixing the sulfur-containing compound absorbed agent obtained by absorbing the sulfur-containing compound in the sulfur-containing compound absorbent with a non-aqueous liquid; Supply means for supplying a gas to be treated containing a sulfur-containing compound discharged from a mining site or a refinery of crude oil or natural gas to the sulfur-containing compound removing unit; With The mixing unit may be a sulfur-containing compound removal device included in a sulfur content recovery device provided at the mining site or the refinery.
- ⁇ Test Example 1> (Preparation of hydrogen sulfide absorbing solution)
- 10 g of NL / MOL and 5 g of N, N, N ′, N′-tetramethylethylenediamine (manufactured by Wako Pure Chemical Industries, Ltd.) were charged and mixed well.
- a mixed gas having a composition of 1% by volume of hydrogen sulfide and 99% by volume of nitrogen was passed through the mixed liquid at a flow rate of 50 mL / min for 3 hours to obtain a reaction liquid that absorbed hydrogen sulfide.
- Example 1 After charging 30 g of crude oil (manufactured by Petroleum Resources Development Co., Ltd.) into a 50 mL sample bottle and adding the reaction solution prepared in Test Example 1 so as to be 2% by mass of the whole, mixing was confirmed and the reaction solution was Completely dissolved, and the mixture was uniform.
- crude oil manufactured by Petroleum Resources Development Co., Ltd.
- Example 2 When 100 g of hyperglass cylinder was charged with 30 g of propane (manufactured by Suzuki Shokan Co., Ltd.), the reaction solution prepared in Test Example 1 was added so as to be 0.5 mass% of the whole, and then mixed to confirm the state. The reaction solution was completely dissolved, and the mixed solution was uniform.
- Example 3 When 30 g of solvent naphtha (manufactured by Wako Pure Chemical Industries, Ltd.) was charged in a 50 mL sample bottle and the reaction solution prepared in Test Example 1 was added so as to be 5% by mass of the whole, it was mixed and confirmed to have a state. The reaction solution was completely dissolved and the mixed solution was uniform.
- solvent naphtha manufactured by Wako Pure Chemical Industries, Ltd.
- Example 4 After charging 30 g of crude oil (manufactured by Petroleum Resources Development) into a 50 mL sample bottle and adding the reaction solution prepared in Test Example 2 so as to be 2% by mass of the whole, mixing was confirmed and the reaction solution was Completely dissolved, and the mixture was uniform.
- the sulfur-containing compound removing apparatus and the sulfur-containing compound removing method using the sulfur-containing compound removing apparatus of the present invention are useful in that the utility and waste required for processing can be reduced when the sulfur-containing compound contained in the gas is removed. is there.
Abstract
Description
このうち金属酸化物を用いる方法は、金属酸化物に由来する廃棄物が発生することが問題視されている。また低分子量アルデヒドを用いる方法は、被処理流体との相溶性の問題や、廃水処理の問題等がある。さらに可逆的吸収剤を用いる方法は、吸収剤を再生するために加熱が必要であるとともに、吸収剤から脱離した硫化水素を処理するための別の処理装置が必要であることから、ユーティリティやプラント建設の費用が過大になる等の課題がある。
[1]含硫黄化合物を含有する被処理ガスを油溶性の含硫黄化合物吸収剤に接触させて前記含硫黄化合物を除去する含硫黄化合物除去部と、
前記含硫黄化合物吸収剤に前記含硫黄化合物を吸収させた含硫黄化合物吸収済剤と非水液体とを混合する混合部と、
を備える含硫黄化合物除去装置。
[2]前記非水液体が炭化水素を含む、[1]の含硫黄化合物除去装置。
[3]前記非水液体が、原油または天然ガスの採掘に伴い発生する液体である、[1]または[2]の含硫黄化合物除去装置。
[4]前記被処理ガスが常温で気体の炭化水素である、[1]~[3]のいずれかの含硫黄化合物除去装置。
[5]原油もしくは天然ガスの採掘現場又は製油所から排出された、含硫黄化合物を含有する被処理ガスを、前記含硫黄化合物除去部に供給する供給手段を備えており、
前記混合部は、前記採掘現場又は前記製油所に設けられた硫黄分回収装置に含まれる、[1]~[4]のいずれかに記載の含硫黄化合物除去装置。
[6][1]~[5]のいずれかの含硫黄化合物除去装置を用いて、含硫黄化合物を含有する被処理ガスから含硫黄化合物を除去する工程を含む、含硫黄化合物除去方法。
本発明において、「含硫黄化合物吸収剤の有効成分の総量」とは、含硫黄化合物吸収剤が溶媒を含む場合には当該溶媒を除く成分の総量を意味し、含硫黄化合物吸収剤が溶媒を含まない場合には含硫黄化合物吸収剤の総量を意味する。
含硫黄化合物が硫黄化合物吸収剤によって別の化合物に変換された後の変換物は、含硫黄化合物吸収済剤として含硫黄化合物除去部から排出されることで、結果として、被処理ガス中における上記含硫黄化合物の当初の量が低下される。
また、疎水性が高く使用後の非水液体への混合が容易であるという観点からは、1,9-ノナンジアールおよび2-メチル-1,8-オクタンジアールからなる群から選択される少なくとも1つの化合物が好ましい。
含硫黄化合物吸収剤中における、α,β-不飽和アルデヒドおよびジアルデヒドの総量は、含硫黄化合物吸収効率の観点からは、好ましくは5質量%以上、より好ましくは10質量%以上、更に好ましくは20質量%以上である。また、当該総量は、好ましくは100質量%以下であり、例えば80質量%以下である。また、一態様として、含硫黄化合物吸収剤は、α,β-不飽和アルデヒドおよびジアルデヒドのみからなっていてもよい。
また、含硫黄化合物吸収剤中における、α,β-不飽和アルデヒドの含有量は、含硫黄化合物吸収効率の観点からは、好ましくは5質量%以上、より好ましくは10質量%以上、更に好ましくは20質量%以上である。また、当該含有量は、好ましくは100質量%以下であり、例えば80質量%以下である。また、一態様として、含硫黄化合物吸収剤は、α,β-不飽和アルデヒドのみからなっていてもよい。
含硫黄化合物吸収剤の有効成分の総量中における、α,β-不飽和アルデヒドおよびジアルデヒドの総量は、含硫黄化合物吸収効率の観点からは、好ましくは40質量%以上、より好ましくは50質量%以上、更に好ましくは60質量%以上である。また、当該総量は、好ましくは100質量%以下であり、例えば80質量%以下である。また、一態様として、含硫黄化合物吸収剤は、α,β-不飽和アルデヒドおよびジアルデヒドのみからなっていてもよい。
また、含硫黄化合物吸収剤の有効成分の総量中における、α,β-不飽和アルデヒドの含有量は、含硫黄化合物吸収効率の観点からは、好ましくは40質量%以上、より好ましくは50質量%以上、更に好ましくは60質量%以上である。また、当該含有量は、好ましくは100質量%以下であり、例えば80質量%以下である。また、一態様として、含硫黄化合物吸収剤は、α,β-不飽和アルデヒドのみからなっていてもよい。
R1~R5は水素原子または炭素数1~6のアルキル基が好ましく、水素原子または炭素数1~4のアルキル基がより好ましく、水素原子またはメチル基がさらに好ましい。
nは0~1000の整数が好ましく、0~100の整数がより好ましく、0~10の整数がさらに好ましく、0~5の整数が特に好ましい。
N,N,N’,N’-テトラメチルジアミノメタン等のWがメチレン基である化合物;
エチレンジアミン、1,2-ジアミノプロパン、1,2-ジアミノ-2-メチルプロパン、N-メチルエチレンジアミン、N-エチルエチレンジアミン、N-プロピルエチレンジアミン、N-ブチルエチレンジアミン、N-ベンジルエチレンジアミン、N-フェニルエチレンジアミン、N,N-ジメチルエチレンジアミン、N,N-ジエチルエチレンジアミン、N,N-ジプロピルエチレンジアミン、N,N-ジブチルエチレンジアミン、N,N’-ジメチルエチレンジアミン、N,N’-ジエチルエチレンジアミン、N,N’-ジプロピルエチレンジアミン、N,N’-ジイソプロピルエチレンジアミン、N,N’-ジターシャリーブチルエチレンジアミン、N,N’-ジベンジルエチレンジアミン、N,N’-ジフェニルエチレンジアミン、N,N’-ビス(2-ヒドロキシエチル)エチレンジアミン、N,N,N’-トリメチルエチレンジアミン、N,N,N’-トリエチルエチレンジアミン、N,N-ジエチル-N’-メチルエチレンジアミン、N,N,N’,N’-テトラメチルエチレンジアミン、N,N,N’,N’-テトラエチルエチレンジアミン、N,N,N’,N’-テトライソプロピルエチレンジアミン、N,N,N’,N’-テトラメチル-1,2-ジアミノプロパン等のWがジメチレン基である化合物;
1,3-プロパンジアミン、2-メチル-1,3-プロパンジアミン、1,3-ジアミノブタン、2,2-ジメチル-1,3-プロパンジアミン、1,3-ジアミノペンタン、N-メチル-1,3-プロパンジアミン、N-エチル-1,3-プロパンジアミン、N-プロピル-1,3-プロパンジアミン、N-ブチル-1,3-プロパンジアミン、N-ベンジル-1,3-プロパンジアミン、N-フェニル-1,3-プロパンジアミン、N,N-ジメチル-1,3-プロパンジアミン、N,N-ジエチル-1,3-プロパンジアミン、N,N-ジプロピル-1,3-プロパンジアミン、N,N’-ジメチル-1,3-プロパンジアミン、N,N’-ジエチル-1,3-プロパンジアミン、N,N,N’-トリメチル-1,3-プロパンジアミン、N,N,N’,N’-テトラメチル-1,3-プロパンジアミン、N,2-ジメチル-1,3-プロパンジアミン、N,N,2,2-テトラメチル-1,3-プロパンジアミン等のWがトリメチレン基である化合物などが挙げられる。
ジエチレントリアミン、2,2’-ジアミノ-N-メチルジエチルアミン、N,N’,N”-トリメチルジエチレントリアミン、N,N,N’,N”,N”-ペンタメチルジエチレントリアミン、N,N,N’,N’-テトラブチルジエチレントリアミン等のWがジメチレン基である化合物;
3,3’-ジアミノジプロピルアミン、N,N-ビス[3-(ジメチルアミノ)プロピル]アミン等のWがトリメチレン基である化合物などが挙げられる。
トリエチレンテトラミン、1,1,4,7,10,10-ヘキサメチルトリエチレンテトラミン等のn=2である化合物;
テトラエチレンペンタミン等のn=3である化合物;
ペンタエチレンヘキサミン等のn=4である化合物などが挙げられる。
含硫黄化合物吸収剤が、ポリアルキレングリコール及び上記一般式(1)で表される多価アミン(1)の少なくとも1種を含有する場合にあっては、含硫黄化合物吸収剤の有効成分の総量中における、ポリアルキレングリコール及び上記一般式(1)で表される多価アミン(1)の総量は、例えば1~50質量%、一態様としては10~40質量%である。
また、含硫黄化合物吸収剤の有効成分の総量中における、ポリアルキレングリコール、上記一般式(1)で表される多価アミン(1)、α,β-不飽和アルデヒドおよびジアルデヒドの総量は、好ましくは60~100質量%、より好ましくは80~100質量%、さらに好ましくは90~100質量%、より好ましくは95~100質量%である。
また、ポリアルキレングリコール及び上記一般式(1)で表される多価アミン(1)の総量は、前記α,β-不飽和アルデヒドおよびジアルデヒドの総量100質量部に対して、好ましくは10~100質量部、より好ましくは30~60質量部であってもよい。
また、含硫黄化合物吸収剤が、上記一般式(1)で表される多価アミン(1)を含有する場合にあっては、含硫黄化合物吸収剤中における、上記一般式(1)で表される多価アミン(1)の含有量は、例えば1~50質量%、一態様としては10~40質量%である。
また、上記一般式(1)で表される多価アミン(1)の含有量は、前記α,β-不飽和アルデヒドの含有量100質量部に対して、好ましくは10~100質量部、より好ましくは30~60質量部であってもよい。
含硫黄化合物除去部の温度に特に制限はないが、好ましくは-30~150℃の範囲内、より好ましくは0~130℃の範囲内である。含硫黄化合物除去部の圧力に特に制限はないが、好ましくは-0.1~10MPa、より好ましくは0~1.0MPaの範囲内である。
このように本発明の含硫黄化合物除去装置では、含硫黄化合物吸収済剤を非水液体に混合して処理することにより、処理に要するユーティリティや廃棄物を低減可能である。
例えば、本発明に係る含硫黄化合物除去装置は、
含硫黄化合物を含有する被処理ガスを油溶性の含硫黄化合物吸収剤に接触させて前記含硫黄化合物を除去する含硫黄化合物除去部と;
前記含硫黄化合物吸収剤に前記含硫黄化合物を吸収させた含硫黄化合物吸収済剤と非水液体とを混合する混合部と;
原油もしくは天然ガスの採掘現場又は製油所から排出された、含硫黄化合物を含有する被処理ガスを、前記含硫黄化合物除去部に供給する供給手段と;
を備えており、
前記混合部は、前記採掘現場又は前記製油所に設けられた硫黄分回収装置に含まれる、含硫黄化合物除去装置であってもよい。
[1,9-ノナンジアール(NL)および2-メチル-1,8-オクタンジアール(MOL)の混合物の製造]
特許第2857055号明細書記載の方法によって、1,9-ノナンジアール(以下、NLと称する)および2-メチル-1,8-オクタンジアール(以下、MOLと称する)の混合物(以下、この混合物をNL/MOLと称する)を製造した。該混合物におけるNLとMOLの質量比は、NL:MOL=85:15であった。
50mL三口フラスコにNL/MOL10g、N,N,N’,N’-テトラメチルエチレンジアミン(和光純薬株式会社製)5gを仕込みよく混合させた。混合液に硫化水素1体積%、窒素99体積%の組成からなる混合ガスを50mL/minの流速で3時間流通させて、硫化水素を吸収した反応液を取得した。
50mL三口フラスコにNL/MOL5gを仕込み、硫化水素1体積%、窒素99体積%の組成からなる混合ガスを50mL/minの流速で15時間流通させて、硫化水素を吸収した反応液を取得した。
50mLのサンプル瓶に原油(石油資源開発製)30gを仕込み、試験例1で調製した反応液を全体の2質量%となるように添加した後、混合して様子を確認したところ、前記反応液は完全に溶解し、混合液は均一であった。
100mLのハイパーグラスシリンダーにプロパン(株式会社鈴木商館製)30gを仕込み、試験例1で調製した反応液を全体の0.5質量%となるように添加した後、混合して様子を確認したところ、前記反応液は完全に溶解し、混合液は均一であった。
50mLのサンプル瓶にソルベントナフサ(和光純薬株式会社製)30gを仕込み、試験例1で調製した反応液を全体の5質量%となるように添加した後、混合して様子を確認したところ、前記反応液は完全に溶解し、混合液は均一であった。
50mLのサンプル瓶に原油(石油資源開発製)30gを仕込み、試験例2で調製した反応液を全体の2質量%となるように添加した後、混合して様子を確認したところ、前記反応液は完全に溶解し、混合液は均一であった。
Claims (6)
- 含硫黄化合物を含有する被処理ガスを油溶性の含硫黄化合物吸収剤に接触させて前記含硫黄化合物を除去する含硫黄化合物除去部と、
前記含硫黄化合物吸収剤に前記含硫黄化合物を吸収させた含硫黄化合物吸収済剤と非水液体とを混合する混合部と、
を備える含硫黄化合物除去装置。 - 前記非水液体が炭化水素を含む、請求項1に記載の含硫黄化合物除去装置。
- 前記非水液体が、原油または天然ガスの採掘に伴い発生する液体である、請求項1または2に記載の含硫黄化合物除去装置。
- 前記被処理ガスが常温で気体の炭化水素である、請求項1~3のいずれかに記載の含硫黄化合物除去装置。
- 原油もしくは天然ガスの採掘現場又は製油所から排出された、含硫黄化合物を含有する被処理ガスを、前記含硫黄化合物除去部に供給する供給手段を備えており、
前記混合部は、前記採掘現場又は前記製油所に設けられた硫黄分回収装置に含まれる、請求項1~4のいずれかに記載の含硫黄化合物除去装置。 - 請求項1~5のいずれかに記載の含硫黄化合物除去装置を用いて、含硫黄化合物を含有する被処理ガスから含硫黄化合物を除去する工程を含む、含硫黄化合物除去方法。
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- 2018-04-27 WO PCT/JP2018/017143 patent/WO2018207657A1/ja active Application Filing
- 2018-04-27 EP EP18799121.1A patent/EP3623034A4/en not_active Withdrawn
- 2018-04-27 JP JP2019517568A patent/JPWO2018207657A1/ja active Pending
- 2018-04-27 BR BR112019017507-5A patent/BR112019017507A2/pt not_active Application Discontinuation
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JP2021146266A (ja) * | 2020-03-18 | 2021-09-27 | 株式会社東芝 | 酸性ガス吸収剤、酸性ガスの除去方法および酸性ガス除去装置 |
JP7273758B2 (ja) | 2020-03-18 | 2023-05-15 | 株式会社東芝 | 酸性ガス吸収剤、酸性ガスの除去方法および酸性ガス除去装置 |
Also Published As
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US20200283357A1 (en) | 2020-09-10 |
EP3623034A1 (en) | 2020-03-18 |
BR112019017507A2 (pt) | 2020-03-31 |
JPWO2018207657A1 (ja) | 2020-05-21 |
EP3623034A4 (en) | 2021-01-13 |
CN110573232A (zh) | 2019-12-13 |
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