CN101386587B - Production technology of methyl naphthalenesulfonic acid-methyl aldehyde condensation compound - Google Patents
Production technology of methyl naphthalenesulfonic acid-methyl aldehyde condensation compound Download PDFInfo
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- CN101386587B CN101386587B CN2007100712985A CN200710071298A CN101386587B CN 101386587 B CN101386587 B CN 101386587B CN 2007100712985 A CN2007100712985 A CN 2007100712985A CN 200710071298 A CN200710071298 A CN 200710071298A CN 101386587 B CN101386587 B CN 101386587B
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- formaldehyde
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- methylnaphthalene
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- 238000009833 condensation Methods 0.000 title claims abstract description 17
- 230000005494 condensation Effects 0.000 title claims abstract description 17
- 150000001875 compounds Chemical class 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 56
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 21
- 238000006482 condensation reaction Methods 0.000 claims abstract description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- 239000000047 product Substances 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- WODGMMJHSAKKNF-UHFFFAOYSA-N 2-methylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WODGMMJHSAKKNF-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 9
- 238000006277 sulfonation reaction Methods 0.000 claims description 9
- 239000007859 condensation product Substances 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 6
- 238000010792 warming Methods 0.000 claims description 6
- 239000008098 formaldehyde solution Substances 0.000 claims description 5
- 238000009413 insulation Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 9
- 239000007788 liquid Substances 0.000 abstract description 8
- 239000002253 acid Substances 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- 229910001424 calcium ion Inorganic materials 0.000 abstract description 3
- 229910001425 magnesium ion Inorganic materials 0.000 abstract description 3
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 abstract description 2
- NFHRENBEPWMURA-UHFFFAOYSA-N C=O.C(O)C1=C(C2=CC=CC=C2C=C1)S(=O)(=O)O Chemical compound C=O.C(O)C1=C(C2=CC=CC=C2C=C1)S(=O)(=O)O NFHRENBEPWMURA-UHFFFAOYSA-N 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- KZGQGOXKCBISME-UHFFFAOYSA-J dicalcium;disulfate Chemical compound [Ca+2].[Ca+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O KZGQGOXKCBISME-UHFFFAOYSA-J 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 abstract 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 abstract 1
- 238000005987 sulfurization reaction Methods 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000984 vat dye Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
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- Phenolic Resins Or Amino Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a method for preparing a condensation compound of methylol naphthalene sulphonic acid formaldehyde. The method comprises the following steps that methylnaphthalene is adopted as the material, and is sulfonated with 104.5 percent of fuming sulfuric acid in advance; the sulfonated product is condensed with formaldehyde; and, finally the pH is adjusted to between 6 and 9 by liquid alkali, and thus the methylol naphthalene sulphonic acid formaldehyde condensation compound is obtained. The method does not need to add an azeotrope former, and does not need to add and distill of sulfonated bodies every time. The process is simplified, the manufacturing cost is saved, and the impurity content in the product is reduced. Additionally, the 104.5 percent of fuming acid is adopted to sulfonate. Not only the efficiency of methylnaphthalene sulfuration is improved, but also the total acidity of the condensation reaction process is reduced. The subsequent process completely adopts liquid alkali. No calcium sulfate calcium offscum is produced. Compared with the adoption of concentrated sulfuric acid, the quality of the product is equivalent in dispersancy, calcium and magnesium ions are not produced, and the product is stable in heat resistance.
Description
(1) technical field
The present invention relates to the production technique of a kind of dye diffusion agent MF (condensation compound of methyl naphthalene sulfonic acid and formaldehyde).
(2) background technology
MF is the formaldehyde condensation products of methyl naphthalene sulfonic acid, is a kind of AS, mainly is used as the dispersion agent and the weighting agent of dispersed dye and vat dyes.It has mill imitates, and dispersiveness, thermotolerance, the advantage that the high temperature stably dispersing is good can be carried out composite to adapt to the commercialization requirement of various dispersed dye and vat dyes with all kinds of dispersion agents.In addition, it go back useful as concrete the dyeing of strong effect water reducer and vat dyes suspensoid staining the time dispersion agent.
Though current domestic MF production technique is various, similar, all be basically with methylnaphthalene (through or without pre-treatment) be that main raw material concentration is that 98% sulfuric acid is as sulphonating agent; Adopt the high mixture ratio sulfuric acid sulfonation, and produce with formaldehyde condensation down, so sulfuric acid consumption height by norm in high total acidity (27%~32%); Contain more excess sulfuric acid in the condensation product, need usually to neutralize with liquid caustic soda, but owing to spent acid amount in the product is big; All adopt in the liquid caustic soda and can cause that sodium sulphate content exceeds standard in the MF product, Given this, guaranteeing under the product quality premise; The part spent acid still need use calcium hydroxide to neutralize; But the calcium sulfate waste residue that produces is difficult for handling, and simultaneously, the calcium ion of introducing is difficult for Ex-all.
Patent 92105199.9 has also been introduced a kind of working method of condensation compound of methyl naphthalene sulfonic acid and formaldehyde; It is to regulate the total acidity that contracts and react through adding a kind of entrainer such as hexane or pentane etc. the vitriol oil of methylnaphthalene and 96% heating azeotropic, when adding formaldehyde carries out condensation reaction, need adding the part condensation product in a step and add water; Need to take out the part condensation reaction products after the condensation reaction and wait until next condensation; Use the method for sodium hydroxide neutralized reaction product at last.The shortcoming of this method is: need to add entrainer, also will have more the technology of one distillation entrainer at last; Need all to reserve at every turn and add recycle stock; Entire reaction course has no closed installation, has sulphur-containing exhaust gas between the reaction period and overflows, and not only causes the loss of raw material, goes back the severe contamination Working environment.
(3) summary of the invention
For addressing the above problem, the invention provides a kind of production technique of condensation compound of methyl naphthalene sulfonic acid and formaldehyde.
The technical scheme that the present invention adopts is:
A kind of production technique of condensation compound of methyl naphthalene sulfonic acid and formaldehyde, said technology comprises the steps:
(1) with the methylnaphthalene is raw material, adds 104.5% oleum, under 120~165 ℃, carry out sulfonation reaction 2~6h, vacuumize in the sulfonation reaction process and remove the water that generates in the reaction, get sulfonated products; Methylnaphthalene is 1: 1.0~1.2 with the ratio of oleum amount of substance;
(2) with sulfonated products be cooled to 80~90 ℃, adding water, to regulate total acidity be 15~20%, adds concentration and be 30~50% formaldehyde solution, under 105~150 ℃, 0.15~0.25MPa, carries out condensation reaction 2~6h, condensation product; Sulfonated products is 1: 0.7~0.8 with the ratio of formaldehyde amount of substance;
(3) after condensation reaction finished, reaction mixture was neutralized to pH value 6~9 with 20~50% sodium hydroxide solution, must contain the solution of condensation compound of methyl naphthalene sulfonic acid and formaldehyde.This solution can directly be used as dispersion agent, and use also separable purification or dry back, and this condenses is soluble in water, is suitable for the preparation of dispersed dye suspension-s, and per 100 parts of dyestuffs need about 25~400 parts of this condenses.
Preferably, said technology is following:
(1) is raw material with the methylnaphthalene, is warming up to 130 ℃, drip 104.5% oleum; Progressively be warming up to 165 ℃ in the dropping process; In 160~165 ℃ of following insulation reaction 3.5h, adopt vacuum pump to bleed in the reaction process and remove the water that generates in the reaction, get sulfonated products; Methylnaphthalene is 1: 1.1~1.15 with the ratio of oleum amount of substance;
(2) with sulfonated products be cooled to 90 ℃, adding water, to regulate total acidity be 17.5%, adds concentration and be 37% formaldehyde solution, under 130 ℃, 0.20~0.25MPa, carries out condensation reaction 3h, condensation product; Sulfonated products is 1: 0.72 with the ratio of formaldehyde amount of substance;
(3) after condensation reaction finished, reaction mixture was neutralized to pH value 7.0~7.3 with 30% sodium hydroxide solution, must contain the solution of condensation compound of methyl naphthalene sulfonic acid and formaldehyde.
Beneficial effect of the present invention is mainly reflected in: (1) need not add entrainer, does not need all to add at every turn and distillate sulfonated bodies yet, has simplified technology, has saved production cost, has reduced foreign matter content in the product; (2) fuming acid of employing 104.5% carries out sulfonation; Not only improved methylnaphthalene sulfonation efficient; And reduced the total acidity of condensation reaction, follow-up whole employing liquid caustic soda neutralize and get final product, and no calcium sulfate waste residue produces; The products obtained therefrom quality is compared with adopting the vitriol oil, and dispersion force quite, does not contain calcium ions and magnesium ions, heat-resisting stable; (3) sulphite that the small amount of exhaust gas that produces in the technology generates after the liquid caustic soda spray equipment absorbs also can be used for the production of sulfonated lignin, is suitable for heavy industrialization and uses.
(4) embodiment
Below in conjunction with specific embodiment the present invention is described further, but protection scope of the present invention is not limited in this:
Embodiment 1:
50g methylnaphthalene (Shanghai Baosteel Chemical Co., Ltd's production) is joined in the four-hole boiling flask of 500ml band stirring, be warming up to 130 ℃, Dropwise 35 g oleum (104.5%) progressively is warmed up to 165 ℃ (dripping in 40~60min) in the dropping process.In 160~165 ℃ of insulation 3.5h, and adopt vacuum pump to bleed (keeping 160~165 ℃), sulfonation is accomplished.
The material that sulfonation is good is cooled to 90 ℃, adds an amount of water, and material acidity is transferred to 17.5%, adds 37% formaldehyde solution, and wherein, sulfonated products is 1: 0.72 with formaldehyde molar weight ratio.Finish, be warming up to 130 ℃ of insulation 3h, control pressure is no more than 0.25MPa, and condensation is accomplished.
The material that condensation is good cools to 85~90 ℃, adds 45g left and right sides water, stirs, and adds liquid caustic soda (30%) again and regulates pH value 7.0~7.3, can obtain the MF finished product, solid content 38~42%, and dispersion force is more than 98%, Na
2SO
4Content 5~7%, heat-resisting 145 ℃, calcic, mg ion do not produce the calcium sulfate waste residue.
The application implementation example:
The Dispersant MF (dry weight 60g) that makes in Disperse Blue-79 filter cake (Shangyu gold hat chemical industry ltd produces) (dry weight 40g) and the foregoing description is carried out high-speed stirring mixes, add water 150g, abundant sand milling, the pH value of accent dye dispersion liquid is 5.Adopt high-temperature and high pressure dyeing process that the polyester yarn fabric is dyeed, dyeing behavior is excellent.
Claims (2)
1. production technique that contains the solution of condensation compound of methyl naphthalene sulfonic acid and formaldehyde, said technology comprises the steps:
(1) with the methylnaphthalene is raw material, adds 104.5% oleum, under 120~165 ℃, carry out sulfonation reaction 2~6h, vacuumize in the sulfonation reaction process and remove the water that generates in the reaction, get sulfonated products; Methylnaphthalene is 1: 1.0~1.2 with the ratio of oleum amount of substance;
(2) with sulfonated products be cooled to 80~90 ℃, adding water, to regulate total acidity be 15~20%, adds concentration and be 30~50% formaldehyde solution, under 105~150 ℃, 0.15~0.25MPa, carries out condensation reaction 2~6h, condensation product; Sulfonated products is 1: 0.7~0.8 with the ratio of formaldehyde amount of substance;
(3) after condensation reaction finished, reaction mixture was neutralized to pH value 6~9 with sodium hydroxide solution, must contain the solution of condensation compound of methyl naphthalene sulfonic acid and formaldehyde.
2. technology as claimed in claim 1 is characterized in that said technology is following:
(1) is raw material with the methylnaphthalene, is warming up to 130 ℃, drip 104.5% oleum; Progressively be warming up to 165 ℃ in the dropping process; In 160~165 ℃ of following insulation reaction 3.5h, adopt vacuum pump to bleed in the reaction process and remove the water that generates in the reaction, get sulfonated products; Methylnaphthalene is 1: 1.1~1.15 with the ratio of oleum amount of substance;
(2) with sulfonated products be cooled to 90 ℃, adding water, to regulate total acidity be 17.5%, adds concentration and be 37% formaldehyde solution, under 130 ℃, 0.20~0.25MPa, carries out condensation reaction 3h, condensation product; Sulfonated products is 1: 0.72 with the ratio of formaldehyde amount of substance;
(3) after condensation reaction finished, reaction mixture was neutralized to pH value 7.0~7.3 with sodium hydroxide solution, must contain the solution of condensation compound of methyl naphthalene sulfonic acid and formaldehyde.
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CN2007100712985A CN101386587B (en) | 2007-09-13 | 2007-09-13 | Production technology of methyl naphthalenesulfonic acid-methyl aldehyde condensation compound |
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CN2007100712985A CN101386587B (en) | 2007-09-13 | 2007-09-13 | Production technology of methyl naphthalenesulfonic acid-methyl aldehyde condensation compound |
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CN101386587B true CN101386587B (en) | 2012-02-01 |
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Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1081451A (en) * | 1992-07-14 | 1994-02-02 | 大连理工大学 | A kind of production method of condensation compound of methyl naphthalene sulfonic acid and formaldehyde |
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Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1081451A (en) * | 1992-07-14 | 1994-02-02 | 大连理工大学 | A kind of production method of condensation compound of methyl naphthalene sulfonic acid and formaldehyde |
Non-Patent Citations (1)
Title |
---|
曹泽环等.扩散剂MF工艺技术改革的探索.《青岛化工学院学报》.1985,(第1期),16-23. * |
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