CN105283430A - Alkylbenzene composition and process for producing alkylbenzene sulfonate - Google Patents
Alkylbenzene composition and process for producing alkylbenzene sulfonate Download PDFInfo
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- CN105283430A CN105283430A CN201480022351.0A CN201480022351A CN105283430A CN 105283430 A CN105283430 A CN 105283430A CN 201480022351 A CN201480022351 A CN 201480022351A CN 105283430 A CN105283430 A CN 105283430A
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- alkylbenzene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/107—Monocyclic hydrocarbons having saturated side-chain containing at least six carbon atoms, e.g. detergent alkylates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Life Sciences & Earth Sciences (AREA)
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Abstract
The invention provides an alkylbenzene composition capable of improving the hue of linear alkylbenzene sulfonates for use in detergent applications, and a process for producing alkylbenzene sulfonates. The alkylbenzene composition of the present invention is an alkylbenzene composition for producing an alkylbenzene sulfonate, wherein the alkylbenzene composition has a UV absorbance at 314nm of 2.98 or less as measured by spectroscopic analysis when the alkylbenzene composition is contained in a quartz sample holder having an optical path length of 1 cm.
Description
Technical field
The present invention relates to the manufacture method of alkyl benzene composition and benzene sulfonamide compound, described alkyl benzene composition is the alkyl benzene composition for the manufacture of benzene sulfonamide compound, and it can improve the form and aspect of the benzene sulfonamide compound using this alkyl benzene composition to manufacture.
Background technology
It is known that the wire alkylbenzene of detergent range (C15 ~ C20) uses wire monoolefine to carry out commercial-scale manufacture to the method that benzene carries out alkylating operation in the presence of acid catalyst by comprising.Generally speaking, this alkylbenzene is sulfonated further, is used to various uses as useful tensio-active agent.
As the manufacture method of benzene sulfonamide compound, such as, have: in alkylbenzene, add the vitriol oil (about 4 times moles) of oleum or surplus and alkylbenzene is carried out sulfonation and obtains the method for alkyl benzene sulphonate (ABS) by the sulphur trioxide of the method manufactured in rhythmic reaction mode, the dilution of utilization non-active gas.In addition, also known under the coexisting of alkylbenzene and alkyl benzene sulphonate (ABS), by alkylbenzene and sulphur trioxide with the continuous sulfonation of equimolar ratio, suppress the generation etc. of sulfone, obtain the method (such as with reference to patent documentation 1) of alkyl benzene sulphonate (ABS).
The improvement of the form and aspect of benzene sulfonamide compound is the problem suppressing just to exist.Propose the method for the form and aspect of several improvement azochlorosulfonate acid compounds up to now.Patent documentation 2 describes thermostability and color stability and to be improved and sludge and sulfuric acid content are minimized, comprise the alkyl aryl sulphonic acid of the alkene of at least 1 % by weight.The alkyl aryl sulphonic acid that patent documentation 2 is recorded suppresses form and aspect during long-term keeping to worsen, but the alkene such as tripolymer, the tetramer containing propylene and butene low polymers, such as propylene keeping after, need to remove olefines when loading and transporting, not only operation complicates, and safedeposit also becomes problem.
In addition, the sulfonic acid process using and there is the unsaturated hydrocarbons of the number-average molecular weight of about 600 ~ 3000 is described in patent documentation 3.But patent documentation 3 reports and can improve form and aspect in alkyl aryl sulphonic acid purifying, but does not report by contacting with unsaturated hydrocarbons structure and improve the effect of form and aspect.And then, need in patent documentation 3 to remove unsaturated hydrocarbons from alkyl aryl sulphonic acid.
And then patent documentation 4 discloses utilizing the method using alkali alumina to process as the micro-organic fluoride impurity in the alkylbenzene of the alkylation process manufacture of catalyzer HF (hydrogen fluoride).Patent documentation 4 reports and utilizes alkali alumina can remove organic fluoride impurity, and utilizes this process can suppress the rising of bromine number and be improved to the form and aspect of sulfonated bodies when utilizing the alkylbenzene of the method manufacture to carry out sulfonation.But according to the Br value rising value in embodiment, the bromine number level of patent documentation 4 is the very high value such more than 0.01, and the Klett of sulfonated bodies (Klett color) is also very high.
In addition, the coloring material precursor can being removed the alkylbenzene of the detergent range before sulfonation by multiple clay and zeolite is reported in patent documentation 5 and 6.But, be conceived to the coloring material precursor of the light absorbing 368nm wavelength in patent documentation 5 and 6, it is said that physical efficiency multiple clay and zeolite adsorption remove before this coloring material, but for absorbing the material of light of 314nm wavelength both without recording also without enlightening.
In recent years, the bromine number of the wire alkylbenzene of detergent range (C15 ~ C20) is less than 0.01 is main flow, is wherein strongly required to improve form and aspect further.But, when carrying out sulfonation for the alkylbenzene on bromine number being less than 0.01 in above-mentioned patent documentation, the impurity of form and aspect can be affected without any report.
Prior art document
Patent documentation
Patent documentation 1: Japanese Laid-Open Patent Publication 53-63346 publication
Patent documentation 2: Japanese Laid-Open Patent Publication 52-102245 publication
Patent documentation 3: Japanese Unexamined Patent Publication 5-262717 publication
Patent documentation 4: Japanese Unexamined Patent Publication 5-271115 publication
Patent documentation 5: United States Patent (USP) No. 4468476 specification sheets
Patent documentation 6: United States Patent (USP) No. 4433196 specification sheets
Summary of the invention
the problem that invention will solve
The object of the invention is to, the alkyl benzene composition of form and aspect and the manufacture method of benzene sulfonamide compound of the wire benzene sulfonamide compound especially can improving washing composition purposes is provided.
for the scheme of dealing with problems
Therefore, the present inventor etc. further investigate to solve above-mentioned problem, and found that, the alkyl benzene composition with the proterties of specified range can improve the form and aspect of benzene sulfonamide compound, thus completes the present invention.
Namely, the feature of alkyl benzene composition of the present invention is, it is the alkyl benzene composition for the manufacture of benzene sulfonamide compound, when aforesaid alkyl benzene composition carries out spectroscopic analysis in the quartz specimen retainer being contained in path length 1cm, the UV absorbancy at the wavelength 314nm place of mensuration is less than 2.98.
In addition, the feature of alkyl benzene composition of the present invention is, in the present invention as stated above, the UV absorbancy at wavelength 314nm place is 2.69 times.
In addition, the feature of alkyl benzene composition of the present invention is, in the present invention as stated above, the UV absorbancy at wavelength 314nm place is less than 2.40.
In addition, the feature of alkyl benzene composition of the present invention is, in the present invention as stated above, comprises more than the alkylbenzene 95 quality % of C16-C19.
In addition, the feature of alkyl benzene composition of the present invention is, in the present invention as stated above, bromine number is less than 0.01.
In addition, the feature of alkyl benzene composition of the present invention is, in the present invention as stated above, fluorine composition is below 0.5ppm.
In addition, the feature of the manufacture method of benzene sulfonamide compound of the present invention is, utilizes sulfate radical to carry out sulfonation to the alkyl benzene composition described in above-mentioned any one.
the effect of invention
The manufacture method of alkyl benzene composition of the present invention and benzene sulfonamide compound has following feature: carry out sulfonation by the alkyl benzene composition being below particular value to the UV absorbancy of certain wave strong point, can manufacture the alkyl benzene sulphonate (ABS) that form and aspect are improved.For the form and aspect of trace, sometimes can take to carry out with UV absorbancy the means that measure, but epoch-making: be that specific value suppresses the form and aspect after sulfonation below by making the UV absorbancy at the wavelength 314nm place of the alkylbenzene before sulfonation.
Accompanying drawing explanation
Fig. 1 is the figure of the relation of the UV absorbancy at the 314nm place that alkyl benzene composition is shown and the Klett of benzene sulfonamide compound.
Embodiment
Below, be described in detail for the present invention.
Alkyl benzene composition of the present invention can improve the form and aspect of benzene sulfonamide compound.In addition, alkyl benzene composition of the present invention easily manufactures painted few benzene sulfonamide compound.The alkyl benzene composition of the reason that the UV-Vis that these improvement can comprise wavelength 314nm place by selection absorbs and low-level impurity obtains.More specifically, when being used by alkyl benzene composition UV-Vis spectrograph to analyze, the absorbancy at this wavelength place is less than 2.98, is more preferably less than 2.69, most preferably is less than 2.40.
The wavelength of 314nm is selected in order to analyze the pure sample product (raw サ Application プ Le) of the alkyl benzene composition in " 1cm path length " colorimetric pool.Several wavelength of about 314nm are useful when the colorimetric pool of the path length of use more than 1 centimetre or 1 centimetre.The absorbancy at wavelength (314nm) place discussed in this description is the absorbancy of specified wavelength, without the need to being the absorbancy with maximum peak.The all analyses measuring UV-Vis absorption all may be used for the present invention.
In the present invention, the path length of sample retainer can change according to used analytical procedure, device.But the path length of sample retainer must be the length needed for concerned impurity fully guaranteeing to detect in alkyl benzene composition.UV-Vis spectrograph is used in the spectrograph that near ultraviolet region, typical case can operate from 200nm to 380nm.
When term " alkylbenzene " uses in this manual, refer to the mixture of the alkylbenzene of C15 ~ C20.As the article of commerce of the raw material alkylbenzene of the benzene sulfonamide compound of washing composition purposes, typical case, has the purity of more than 95 quality % in the carbon range of C16 ~ C19.Therefore, alkyl benzene composition of the present invention preferably comprises more than the alkylbenzene 95 quality % of the carbon range of C16 ~ C19.
In the present invention, alkyl benzene composition uses catalyzer to be manufactured by monoolefine and benzene, and described monoolefine utilizes platinum catalyst to carry out dehydrogenation to the normal paraffin of C9 ~ C14 and manufactures.Catalyzer uses HF, zeolite, silica-alumina etc.HF is called as DetergentAlkylation (detergent alkylation) technique as the manufacture method of the alkylbenzene of catalyzer, benzene and wire monoolefine are carried out alkylation under the existence of liquid hydrofluoric acid (HF).In addition, zeolite is called as Detal technique as the manufacture method of the alkylbenzene of catalyzer, benzene and wire monoolefine are carried out alkylation under the existence of solid catalyst zeolite.The manufacture method of alkylbenzene has multiple method, and the manufacture method of the alkyl benzene composition in the present invention is not limited to these.
Typically, when HF is manufactured alkylbenzene as catalyzer, the fluorine composition that in alkylbenzene, trace is mixed into makes the deterioration of alkylbenzene, is therefore utilizing solid alumina sorbent to process afterwards, and is making it at least become below 0.5ppm.
As solid alumina sorbent, the activated alumina etc. used in organic absorption purposes can be exemplified.They also can use suitable binding agent shaping.As long as can the sorbent material of Adsorption of fluoride composition, then basic metal, alkaline-earth metal or other metal be suitable for can be used to be impregnated in aluminum oxide with oxide compound, oxyhydroxide or other form or to utilize other method to be carried on aluminum oxide aptly and carry out the sorbent material of modification.But, typically, without the need to so load/modification especially, can use the content of the basic metal such as sodium or alkaline-earth metal be less than 0.5 % by weight aluminum oxide.
In addition, owing to utilizing monoolefine and benzene to react in the manufacture method of alkylbenzene, in alkylbenzene, be therefore mixed into the olefinic component of trace.They make the deterioration of alkylbenzene, therefore usually make it reduce utilizing the sorbent materials such as atlapulgite to carry out processing afterwards.The mixed volume of these impurity can be held by measuring bromine number.Bromine number is preferably less than 0.01, more preferably less than 0.005, be more preferably less than 0.001.
When term " benzene sulfonamide compound " uses in this manual, refer to and utilize sulfate radical to carry out the material of sulfonation to the alkyl benzene composition of C15 ~ C20.
When term " the pure sample product of alkylbenzene " uses in this manual, refer to chemical preparations (alkylbenzene), and do not comprise the material being formed by the subsequent purification (single or multiple) of the chemosynthesis of alkylbenzene and the alkylbenzene of synthesis, generated by chemosynthesis and/or purifying (single or multiple), not containing any additional artificial chemicals (single or multiple) yet.
When term " impurity " uses in this manual, when referring to reference to UV-Vis absorption spectrum, with alkylbenzene at chemically non-equivalence, but there is at wavelength 314nm place the compound of more than a kind or a kind that UV absorbs.The present inventor etc. find that these impurity can by contacting purifying with mineral compound or removing by distilling.
(distillation)
Purified alkyl benzene composition of the present invention can be distilled at any heating under pressure by the alkyl benzene composition comprising above-mentioned trace impurity, thus the UV absorbancy being purified to 314nm place is the alkyl benzene composition of less than 2.98.
The form of distillation can use the arbitrary form such as intermittent type, continous way.
(adsorbent contact process)
Purified alkyl benzene composition of the present invention can be the adsorbent contact process by the alkylbenzene and adsorbent contact making to comprise above-mentioned trace impurity, thus the UV absorbancy being purified to 314nm place is the alkyl benzene composition of less than 2.98.
Adsorbent contact processing example is as by making the alkyl benzene composition and the aluminum oxide (Al that comprise above-mentioned trace impurity
2o
3), the adsorbent contact such as atlapulgite, silicon-dioxide, zeolite carries out.In order to remove there is at wavelength 314nm place more than a kind or a kind compound that UV absorbs and the aluminum oxide that uses and atlapulgite can use in order to remove HF and alkene and aluminum oxide and atlapulgite.
The particle diameter of sorbent material used herein is generally 1 ~ 10mm, is preferably the scope of 2 ~ 4mm, and specific surface area is generally 50 ~ 500m
2/ g, preferably 200 ~ 500m
2the scope of/g.
After the alkyl benzene composition making to comprise above-mentioned trace impurity and adsorbent contact, such as, by filtering or making sorbent material precipitate and get the methods such as supernatant liquor, alkyl benzene composition and sorbent material can be separated.
Carry out above-mentioned distillation process and/or UV absorbancy that above-mentioned adsorbent contact process obtained, was purified to wavelength 314nm place be the alkyl benzene composition of less than 2.98 when used as benzene sulfonamide compound raw material, with directly use compared with commercially available alkylbenzene painted less, excellent quality.Can think this is because to the painted impurity impacted when can remove the sulfonation comprised in commercially available alkylbenzene.
(mensuration of bromine number)
Bromine number in the present invention is by measuring based on the potentiometric titration of JISK2605 (petroleum product-bromine number test method-potentiometric titration).
(mensuration of fluorine composition)
Fluorine composition in the present invention uses ion chromatograph to measure.
Embodiment
The present invention specifically described further by the following examples, the present invention is not limited to these embodiments.
(experiment 1)
Using the normal paraffin mixture of C9 ~ C14 and benzene as raw material, after catalyzer uses liquid HF to manufacture alkylbenzene, carry out aluminum oxide (AXENS Inc. PSG-A25) and clay treatment (atlapulgite: marshy land KCC Galleonite251, treatment temp 70 DEG C), implement distillation purifying, collect that 5 C16-C19 obtained thus are more than 95 quality %, molecular-weight average is 240 ~ 244 and the alkylbenzene sample (embodiment 1 ~ 3, comparative example 1 ~ 2) that bromine number is less than 0.01, fluorine composition is below 0.5ppm.For this sample, use the absorbancy of UV-Vis spectrophotometer 314nm.In addition, implement sulfonation for these alkyl benzene composition, measure Klett for the benzene sulfonamide compound obtained.Show the result in table 1.
(experiment 2)
Collect sample in the same manner as experiment 1, use the absorbancy of UV-Vis spectrophotometer 314nm.In addition, implement the sulfonation of alkylbenzene for these alkylbenzenes, measure Klett (comparative example 3) for the benzene sulfonamide compound obtained.
(experiment 3)
The sample of experiment 2 is distilled again, obtains sample light composition and heavy ingredient being eliminated separately 3%.For this sample, use the absorbancy of UV-Vis spectrophotometer 314nm.In addition, implement the sulfonation of alkylbenzene for these alkylbenzenes, measure Klett (embodiment 4) for the benzene sulfonamide compound obtained.
(experiment 4)
Do not implement clay treatment, collect sample in the same manner as experiment 1, use the absorbancy of UV-Vis spectrophotometer 314nm.In addition, implement the sulfonation of alkylbenzene for these alkylbenzenes, measure Klett (comparative example 4) for the benzene sulfonamide compound obtained.
(experiment 5)
The sample of experiment 2 is implemented process with atlapulgite repeatedly and after obtaining sample, uses the absorbancy of UV-Vis spectrophotometer 314nm.In addition, implement the sulfonation of alkylbenzene for these alkylbenzenes, implement Klett (embodiment 5) for the benzene sulfonamide compound obtained.
(UV-Vis analysis)
After the pure sample product of alkylbenzene being dropped into the quartz cuvette pond of path length 1cm, analyzed by UV-Vis spectrograph.Control group does not put into colorimetric pool, is made as air controls group.UV-Vis spectrum uses SHIMADZUUV-2550UV-VISSPECTROPHOTOMETER (UV-VIS spectrophotometer) to collect.Spectrograph record is by the UV-Vis absorption spectrum of about 200nm to about 800nm, and the numerical value generating the absorbancy of report 314nm exports.For the absorption of 314nm, there is the shoulder at the peak of obvious high strength in typical case.The absorption being absorbed as specified wavelength place mensuration of 314nm, without the need to being the absorption with maximum peak.
(sulfonation of alkylbenzene and the mensuration of Klett)
With reference to the method that the embodiment 1 of Japanese Unexamined Patent Publication 2008-94941 publication is recorded, synthesis of alkyl benzene sulfonated bodies.10% ethanolic soln of the benzene sulfonamide compound prepared, utilizes spectrophotometer by ethanol in contrast, to measure absorbancy under wavelength 420nm, sample colorimetric pool 10mm, obtains the value (Klett) that absorbance is multiplied by coefficient 1000.
The relation of the absorbancy of whole alkylbenzene sample and the Klett of benzene sulfonamide compound is shown in Fig. 1.
[table 1]
[table 2]
From table 1 obviously: be that the alkyl benzene composition of less than 2.98 is as the form and aspect step-down of the benzene sulfonamide compound of raw material using the UV absorbancy at 314nm place during alkyl benzene composition of the present invention, i.e. UV-Vis absorb.In addition, the absorbancy of 314nm is confirmed according to Fig. 1 and form and aspect have high correlation.As long as the benzene sulfonamide compound that the commercially available Klett of the benzene sulfonamide compound of washing composition purposes is less than 40 just can use, being more preferably less than 30, expecting most is less than 20.
Claims (7)
1. an alkyl benzene composition, is characterized in that, it is the alkyl benzene composition for the manufacture of benzene sulfonamide compound,
When described alkyl benzene composition carries out spectroscopic analysis in the quartz specimen retainer being contained in path length 1cm, the UV absorbancy at the wavelength 314nm place of mensuration is less than 2.98.
2. alkyl benzene composition according to claim 1, is characterized in that, the absorbancy at wavelength 314nm place is less than 2.69.
3. alkyl benzene composition according to claim 2, is characterized in that, the absorbancy at wavelength 314nm place is less than 2.40.
4. the alkyl benzene composition according to any one of claims 1 to 3, is characterized in that, comprises more than the alkylbenzene 95 quality % of C16-C19.
5. the alkyl benzene composition according to any one of Claims 1 to 4, is characterized in that, bromine number is less than 0.01.
6. the alkyl benzene composition according to any one of Claims 1 to 5, is characterized in that, fluorine composition is below 0.5ppm.
7. a manufacture method for benzene sulfonamide compound, is characterized in that, utilizes sulfate radical to carry out sulfonation to the alkyl benzene composition according to any one of claim 1 ~ 6.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013-088671 | 2013-04-19 | ||
| JP2013088671 | 2013-04-19 | ||
| PCT/JP2014/060438 WO2014171398A1 (en) | 2013-04-19 | 2014-04-10 | Method for producing alkyl-benzene composition and alkyl benzene sulfonate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105283430A true CN105283430A (en) | 2016-01-27 |
Family
ID=51731340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201480022351.0A Pending CN105283430A (en) | 2013-04-19 | 2014-04-10 | Alkylbenzene composition and process for producing alkylbenzene sulfonate |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP6283662B2 (en) |
| KR (1) | KR20150144761A (en) |
| CN (1) | CN105283430A (en) |
| TW (1) | TWI615379B (en) |
| WO (1) | WO2014171398A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113548940A (en) * | 2021-07-22 | 2021-10-26 | 杭州智华杰科技有限公司 | Preparation method of high-purity alkylbenzene |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102336437B1 (en) * | 2021-08-19 | 2021-12-07 | 에이케이켐텍 주식회사 | Method for producing reactive emulsifier for nitrile copolymer latex manufacturing |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52136205A (en) * | 1976-05-11 | 1977-11-14 | Sumitomo Chem Co Ltd | Hydrogenation and purification of alkylbenzene for detergents |
| CN101437790A (en) * | 2006-03-16 | 2009-05-20 | 西班牙石油化学公司 | Method for preparing linear alkyl benzene sulfonate with high solubility |
| CN101970388A (en) * | 2007-12-04 | 2011-02-09 | 塞普萨化学公司 | Method for obtaining monoalkylated aromatic compounds with high linearity and adjustable isomerism |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5016350B1 (en) * | 1969-07-03 | 1975-06-12 | ||
| GB1572496A (en) | 1976-02-20 | 1980-07-30 | Exxon Research Engineering Co | Stabilisation of alkylaryl sulphonic acids and sulphonates |
| JPS6045185B2 (en) | 1976-11-17 | 1985-10-08 | 丸善石油株式会社 | Method for sulfonating aromatic compounds |
| US4468476A (en) | 1982-06-25 | 1984-08-28 | Conoco Inc. | Color precursor removal from detergent alkyl benzenes |
| US4433196A (en) | 1982-06-25 | 1984-02-21 | Conoco Inc. | Color precursor removal from detergent range alkyl benzenes |
| FR2559764B1 (en) * | 1984-02-16 | 1988-01-29 | Poudres & Explosifs Ste Nale | NOVEL A-CHLORINE CARBONATES, THEIR MANUFACTURING PROCESS AND THEIR APPLICATION TO PROTECT THE AMINE FUNCTIONS OF AMINO ACIDS |
| US5185485A (en) * | 1991-06-28 | 1993-02-09 | Monsanto Company | Process for preparing alkylbenzene |
| US5344967A (en) | 1991-06-28 | 1994-09-06 | The Lubrizol Corporation | Treatment of organic sulfonic acid |
| CN101437779B (en) * | 2006-05-08 | 2013-09-25 | 塞普萨化学公司 | Method for purifying alkyl aromatics compound |
-
2014
- 2014-04-10 JP JP2015512464A patent/JP6283662B2/en not_active Expired - Fee Related
- 2014-04-10 KR KR1020157030732A patent/KR20150144761A/en not_active Withdrawn
- 2014-04-10 WO PCT/JP2014/060438 patent/WO2014171398A1/en active Application Filing
- 2014-04-10 CN CN201480022351.0A patent/CN105283430A/en active Pending
- 2014-04-18 TW TW103114234A patent/TWI615379B/en not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52136205A (en) * | 1976-05-11 | 1977-11-14 | Sumitomo Chem Co Ltd | Hydrogenation and purification of alkylbenzene for detergents |
| CN101437790A (en) * | 2006-03-16 | 2009-05-20 | 西班牙石油化学公司 | Method for preparing linear alkyl benzene sulfonate with high solubility |
| CN101970388A (en) * | 2007-12-04 | 2011-02-09 | 塞普萨化学公司 | Method for obtaining monoalkylated aromatic compounds with high linearity and adjustable isomerism |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113548940A (en) * | 2021-07-22 | 2021-10-26 | 杭州智华杰科技有限公司 | Preparation method of high-purity alkylbenzene |
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2014171398A1 (en) | 2017-02-23 |
| TWI615379B (en) | 2018-02-21 |
| KR20150144761A (en) | 2015-12-28 |
| WO2014171398A1 (en) | 2014-10-23 |
| TW201509873A (en) | 2015-03-16 |
| JP6283662B2 (en) | 2018-02-21 |
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