CN1636962A - Production method of multi-variety low-consumption plasticizer - Google Patents
Production method of multi-variety low-consumption plasticizer Download PDFInfo
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- CN1636962A CN1636962A CN 03113054 CN03113054A CN1636962A CN 1636962 A CN1636962 A CN 1636962A CN 03113054 CN03113054 CN 03113054 CN 03113054 A CN03113054 A CN 03113054A CN 1636962 A CN1636962 A CN 1636962A
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- acid
- phthalate
- esterification
- plasticizer
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- 239000004014 plasticizer Substances 0.000 title abstract description 9
- 238000005886 esterification reaction Methods 0.000 claims abstract description 30
- 230000032050 esterification Effects 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 16
- -1 di (2-ethyl) hexyl phthalate Chemical compound 0.000 claims abstract description 15
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims abstract description 12
- JQCXWCOOWVGKMT-UHFFFAOYSA-N diheptyl phthalate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000007670 refining Methods 0.000 claims abstract description 10
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 8
- OEIWPNWSDYFMIL-UHFFFAOYSA-N dioctyl benzene-1,4-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C=C1 OEIWPNWSDYFMIL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 7
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 claims abstract description 6
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 claims abstract description 6
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 claims abstract description 6
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 claims abstract description 6
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000002148 esters Chemical class 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 239000004902 Softening Agent Substances 0.000 claims description 18
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 7
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 5
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims description 4
- 238000005516 engineering process Methods 0.000 claims description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical group C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 125000005591 trimellitate group Chemical group 0.000 claims description 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 3
- IHLDEDLAZNFOJB-UHFFFAOYSA-N 6-octoxy-6-oxohexanoic acid Chemical compound CCCCCCCCOC(=O)CCCCC(O)=O IHLDEDLAZNFOJB-UHFFFAOYSA-N 0.000 claims description 2
- 244000248349 Citrus limon Species 0.000 claims description 2
- 235000005979 Citrus limon Nutrition 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 150000007520 diprotic acids Chemical class 0.000 claims 1
- 238000005265 energy consumption Methods 0.000 abstract description 4
- 239000012752 auxiliary agent Substances 0.000 abstract description 2
- 238000010923 batch production Methods 0.000 abstract 2
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 abstract 2
- 238000009776 industrial production Methods 0.000 abstract 1
- LNYCJZRLMAMTQW-UHFFFAOYSA-N trioctyl 2-hydroxy-4-oxopentane-1,2,3-tricarboxylate Chemical compound CCCCCCCCOC(=O)CC(O)(C(=O)OCCCCCCCC)C(C(C)=O)C(=O)OCCCCCCCC LNYCJZRLMAMTQW-UHFFFAOYSA-N 0.000 abstract 1
- APVVRLGIFCYZHJ-UHFFFAOYSA-N trioctyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCCCCCCOC(=O)CC(O)(C(=O)OCCCCCCCC)CC(=O)OCCCCCCCC APVVRLGIFCYZHJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000002932 luster Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 3
- 239000004439 Isononyl alcohol Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 description 1
- GPZYYYGYCRFPBU-UHFFFAOYSA-N 6-Hydroxyflavone Chemical compound C=1C(=O)C2=CC(O)=CC=C2OC=1C1=CC=CC=C1 GPZYYYGYCRFPBU-UHFFFAOYSA-N 0.000 description 1
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000004440 Isodecyl alcohol Substances 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a novel method for industrially producing a PVC auxiliary agent plasticizer with multiple varieties, low raw materials and energy consumption by using the same batch production equipment, wherein the varieties of the plasticizer which can be produced by the same batch production equipment comprise di (2-ethyl) hexyl phthalate (DOP), dibutyl phthalate (DBP), dioctyl terephthalate (DOTP), tri (2-ethyl) hexyl trimellitate (TOTM), diisononyl phthalate (DINP), diisodecyl phthalate (DIDP), diheptyl phthalate (DHP), dioctyl adipate (DOA), dioctyl sebacate (DOS), tributyl citrate, trioctyl citrate, tributyl acetylcitrate and trioctyl acetylcitrate, and the process route is as follows: esterification → dealcoholization → neutralization → refining → plasticizer product. Can shorten the industrial production period and reduce the production cost of the plasticizer product.
Description
The technical field that the present invention relates to be utilize same set of intermittent type softening agent equipment can many kinds, a kind of novel method of suitability for industrialized production softening agent product of low raw materials consumption, low energy expenditure.
At present both at home and abroad suitability for industrialized production softening agent Zhu is Yaoed You Even continuousization production technique and gap method production technique Even and is continued metallization processes and be characterized in that constant product quality, energy consumption province, production operation be convenient to automatization and control, but shortcoming is that the facility investment expense is bigger, and be confined to the variety production of single softening agent, can't carry out the conversion of the many kinds of softening agent.And traditional interrupter method, though can carry out the conversion of the many kinds of softening agent, the energy, raw material consumption height, production cycle are long, two kinds of routes of producing softening agent:
Even continues method technology
Esterification → dealcoholysis → neutralization → washing →
Refining → the softening agent product
Traditional batch method technology
Esterification → neutralization → washing → dealcoholysis →
Refining → the softening agent product
The present invention seeks to utilize same set of intermittent reaction equipment can produce many kinds softening agent product, and can reduce starting material, energy consumption, ultimate principle is that the thermal discharge that makes full use of esterification in synthetic ester product technological process, the generation heat of ester and the heat of thick ester liquid remove the excessive 70%-80% raw alcohol of esterification, deviate from the pure recyclable utilization of reactive system, save starting material to reach, reduce energy consumption and the purpose of shortening production cycle.
The invention concrete grammar is in the esterification reaction process of raw material acid (or acid anhydrides) and organic alcohol, when the transformation efficiency of reactant acid (or acid anhydrides) reaches 90%, stop the esterification system heat supply, utilize the heat release and the thick ester of esterification to produce the alcohol excess that latent heat removes the esterification adding, this process can play the esterification reaction process of promptly finishing the later stage, can slough the excessive raw alcohol of reaction again, and to deviate from the raw alcohol of esterification system water content few this moment, help reclaiming the utilization again of alcohol, reduce the consumption of raw alcohol, when removing 70～80% alcohol excess, this moment esterification system in acid (or acid anhydrides) transformation efficiency greater than 99%, esterification reaction temperature drops to 150 ℃～120 ℃ from 250 ℃～210 ℃, neutralizes again, the refining product that obtains softening agent is sloughed 30%～20% excessive alcohol again in treating process.Esterification, neutralization, washing, dealcoholysis, purified operational path in the traditional plasticizer production have been avoided fully.Operational path of the present invention is as follows:
Esterification → dealcoholysis → neutralization → refining → softening agent product
Be applicable to the chemical equation of principle of the invention production softening agent:
(1) Tetra hydro Phthalic anhydride and alcohol
(2) trimellitic acid 1,2-anhydride and alcohol
(3) terephthalic acid and alcohol
(4) citric acid and alcohol
(5) binary lipid acid and alcohol
R in the above-mentioned reaction formula can be C
4～C
13Fatty Alcohol(C12-C14 and C12-C18), carbochain can be that straight chain also can have side chain; N can be 4～8.
The many kinds softening agent that is suitable for the present invention's production is: phthalic acid two (2-ethyl) own ester (DOP), dibutyl phthalate (DBP), dioctyl terephthalate (DOTP), tri trimellitate (2-ethyl) own ester (TOTM), diisononyl phthalate (DINP), Di Iso Decyl Phthalate (DIDP), diheptyl phthalate (DHP), Octyl adipate (DOA), dioctyl sebacate (DOS), tributyl citrate, trioctyl lemon acid, tributyl acetylcitrate, acetyl tributyl citrate three monooctyl esters etc.
Be applicable to that esterifying catalyst of the present invention is non-sulfuric acid, aprotic acid catalyzer: mainly containing tetrabutyl titanate, titanium isopropylate, tetrabutyl titanate and titanium isopropylate composite catalyst, solid acid catalyst has tin protoxide, stannous oxalate, aluminum oxide, sodium metaaluminate, solid super-strong acid.
The esterification feed that is applicable to suitability for industrialized production of the present invention is organic acid or anhydride: Tetra hydro Phthalic anhydride, trimellitic acid 1,2-anhydride, terephthalic acid, citric acid, hexanodioic acid, sebacic acid, pentanedioic acid; The esterification raw alcohol is: propyl carbinol, 2-ethyl hexanol, n-Heptyl alcohol, nonylcarbinol, nonanol-iso-heptanol, isodecyl alcohol, isononyl alcohol.
Embodiment 1 synthetic common plasticizer phthalic acid two (2-ethyl) own ester (DOP)
At the intermittent type volume is 30M
3Have a packing tower, add 6.5 tons of anhydride phthalic acids in the stainless steel reaction kettle of the esterification of condenser, 14.5 tons of 2-Ethylhexyl Alcohols, catalyzer metatitanic acid four isopropyl ester 5KG, activated carbon 5KG, be heated between 160 ℃～230 ℃ from room temperature and carry out esterification, measure esterification liquid acid value 5.0mgKOH/g behind the reaction 3h, open vacuum system, vacuum tightness-0.72～-0.85Mpa under dealcoholysis, after 2.5 tons of 2-Ethylhexyl Alcohols were sloughed the esterification system, reacting liquid temperature was 160 ℃～110 ℃, and the thick ester acid value of esterification drops to 0.2mgKOH/g, through neutralization, after stripping 2.5h is refining, get 17.08 tons of DOP finished products.Finished product ester content: greater than 99%; Density (p): 0.982-0.988g/cm
3Weight loss on heating (125 ℃, 2 hours): 0.09%; Color and luster (APHA): 15; Finished product acid value: 0.02mgKOH/g; Flash-point (opening agar diffusion method): 195 ℃, volume resistivity: 5 * 10
11(Ω M), (180 ℃/2h) color and luster: 40 (APHA) of heating backs; (180 ℃/2h) acid value: 0.06mgKOH/g of heating backs.
Example 2 synthesizing news, 105 ℃ of level high temperature plasticizers tri trimellitate (2-ethyl) own esters (TOTM)
Be equipped with in the glass there-necked flask of stirring, thermometer, condenser, pure water separator at 500ml, add inclined to one side benzene three inclined to one side acid anhydride 0.5mol (96.0g), 2-Ethylhexyl Alcohol 2.5mol (325.0g) is with 2.0g solid super-strong acid SO
4 2-/ ZrO
2As esterifying catalyst, add the 2.0g activated carbon, behind esterification 3h under 210 ℃ of conditions, benzene three inclined to one side acid anhydride transformation efficiencys are 95.8% partially, the color and luster 80 (APHA) of thick ester switches to vacuum condition, takes off the excessive 2-Ethylhexyl Alcohol of part under-0.95Mpa, after making temperature of reaction drop to 150 ℃, separating catalyst, catalyzer can be recycled, and uses 3% NaOH solution neutralized crude esters then, after refining, obtain inclined to one side benzene three (2-ethyl) own ester (TOTM) product.The finished product acid value is 0.056mgKOH/g, and color and luster is 70 (APHA), and ester content is 99.6%, and flash-point is 245 ℃, and the volume electrostrictive coefficient is 2.0 * 10
12(Ω M).Refining back product yield is 98.2%, the selectivity 98.0% of reaction.
Example 3 synthetic 95 ℃ of special plastic auxiliary agent terephthalic acid two (2-ethyl) own esters (DOTP)
Stirring is being housed, thermometer, condenser, in the 500ml glass there-necked flask of alcohol water separator, the mol ratio that adds esterification feed 2-Ethylhexyl Alcohol and terephthalic acid is .3.5mol: 1mol, the tetrabutyl titanate catalyzer that adds total raw material charging capacity 0.3%, add the 1.0g activated carbon, behind reaction esterification 6.5h under 220 ℃ of conditions, thick ester esterification terminating point acid value is 0.5mgKOH/g, the color and luster 120 (APHA) of thick ester, after taking off the excessive alcohol of part, neutralization then, behind the stripping, the acid value of ester finished product is 0.07mgKOH/g, color and luster is 70 (APHA), ester content is 99.6%, and flash-point is 218 ℃, and the volume electrostrictive coefficient is 1.0 * 10
12(Ω M), refractive index n
25 D1.4687 refining back product yield is 98.2%, the selectivity 98.0% of reaction.
Example 4 synthetic extraordinary cold resisting type softening agent diisononyl adipates
Have in the esterification device of stirring, thermometer, condenser, pure water separator at 1000ml, add 200g hexanodioic acid, 500g isononyl alcohol, 1g activated carbon respectively, stirring adds titanium isopropylate after being warmed to 180 ℃, be warmed to 220 ℃ again, 3h measures esterification liquid acid value 2.5mgKOH/g, and the vacuum degree condition dealcoholysis is behind the recovery 84.3g isononyl alcohol, when 100 ℃ of liquid temperature, add 5% Na
2CO
3Solution, measure thick ester acid value 0.021mgKOH/g after the water phase separated, add activated carbon 0.5g, magnesium oxide 0.5g, in vacuum tightness be-the 0.9Mpa condition under stripping 0.5h, cooled and filtered ester liquid, get diisononyl adipate product 540.5g, color and luster 25 (APHA), 195 ℃ of flash-points, acid value 0.05mgKOH/g.
Claims (4)
1. utilize the same set of equipment of softening agent can many kinds, low raw materials consumption, a kind of method of suitability for industrialized production softening agent product of low energy expenditure, the softening agent kind that adopts the present invention to produce is: phthalic acid two (2-ethyl) own ester (DOP), dibutyl phthalate (DBP), dioctyl terephthalate (DOTP), tri trimellitate (2-ethyl) own ester (TOTM), diisononyl phthalate (DINP), Di Iso Decyl Phthalate (DIDP), diheptyl phthalate (DHP), Octyl adipate (DOA), dioctyl sebacate (DOS), tributyl citrate, trioctyl lemon acid, tributyl acetylcitrate, acetyl tributyl citrate three monooctyl esters etc.
2. the organic alcohol of raw material is C
4～C
13Fat alcohol compound, carbochain can be that straight chain also can have side chain in the molecular structure; Organic acid anhydride is Tetra hydro Phthalic anhydride, trimellitic acid 1,2-anhydride; Organic acid is terephthalic acid, citric acid; Diprotic acid is hexanodioic acid, sebacic acid, pentanedioic acid.
3. the esterifying catalyst of the present invention's use is tetra-n-butyl titanate, titanium isopropylate, tetrabutyl titanate and titanium isopropylate composite catalyst, tin protoxide, aluminum oxide, sodium metaaluminate, solid super-strong acid.
4. technology of the present invention is the intermittent type esterification production method, and technology characteristics is: esterification, dealcoholysis, neutralization, refining.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB031130542A CN100404496C (en) | 2003-03-26 | 2003-03-26 | Production process of plasticizer with multiple variety and low consumption |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB031130542A CN100404496C (en) | 2003-03-26 | 2003-03-26 | Production process of plasticizer with multiple variety and low consumption |
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| Publication Number | Publication Date |
|---|---|
| CN1636962A true CN1636962A (en) | 2005-07-13 |
| CN100404496C CN100404496C (en) | 2008-07-23 |
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Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1326829C (en) * | 2005-09-05 | 2007-07-18 | 吉化集团公司 | Diisodecyl phthalate preparation method |
| CN100363328C (en) * | 2005-11-08 | 2008-01-23 | 江南大学 | Trimellitic tri(C8-9 ol)ester preparation method |
| CN101139293B (en) * | 2007-08-17 | 2010-08-25 | 郭立耀 | Method for producing dioctyl terephthalate |
| CN101973884A (en) * | 2010-09-26 | 2011-02-16 | 昆山合峰化工有限公司 | Method for preparing triisononyl trimellitate (TINTM) |
| CN102219688A (en) * | 2011-05-05 | 2011-10-19 | 江南大学 | Method for improving thermal stability of dibutyl/diisobutyl phthalate |
| CN103080066A (en) * | 2010-08-27 | 2013-05-01 | 罗狄亚聚酰胺特殊品有限公司 | Method for preparing di-alpha-methyl benzyl adipate |
| CN105399625A (en) * | 2015-12-18 | 2016-03-16 | 安徽香枫新材料股份有限公司 | Preparation method for cold-resistant plasticizer dioctyl sebacate |
| CN105504347A (en) * | 2015-12-11 | 2016-04-20 | 安徽律正科技信息服务有限公司 | Light-resistant, heat-resistant and anti-aging plasticizer for plastics |
| WO2016126080A1 (en) * | 2015-02-04 | 2016-08-11 | 한화케미칼 주식회사 | Environmentally friendly plasticizer composition, and vinyl chloride resin composition containing same |
| CN109153630A (en) * | 2016-05-25 | 2019-01-04 | 沙特基础工业全球技术有限公司 | The synthesis of triphen alkyl formate |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1169420A (en) * | 1996-06-21 | 1998-01-07 | 巴陵石油化工公司鹰山石油化工厂 | Method for preparing dicyclohexyl phthalate |
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