【Haichuan Project Updates】Has the Dongying million-ton aromatic lactam project started?

Located in the Dongying Port Economic Development Zone of Dongying City, Shandong Province, it was invested in by Shandong Weirui Chemical Co., Ltd. to build a 1.6 million tons per year aromatic compounds complex. Process flow: Raw materials -- Preheating -- Synthesis -- Cooling -- Separation -- Product. The total investment for the project is approximately 8 billion yuan, to be funded by the enterprise itself.

( Dongying, Shandong ) 1.2 million tons per year caprolactam project. Investors: Hengyi Petrochemical Co., Ltd. and Zhejiang Baling Hengyi Caprolactam Co., Ltd.; Designer: Hunan Baili Engineering Technology Co., Ltd. With a total investment of around 18 billion yuan, it utilizes the internationally leading Sinopec ammonia oximation technology to mainly produce caprolactam, nylon polymer chips, and fibers.

Hengyi Petrochemical Co., Ltd. and Zhejiang Baling Hengyi Caprolactam Co., Ltd. – Hengyi Petrochemical is really investing heavily!

Baili Technology is a technology-driven engineering company that starts with petrochemicals and moves towards modern coal chemical industries. It possesses **Class A qualifications for engineering consultation, engineering design, and related general contracting services; it also has advanced design and engineering management tools, as well as a comprehensive QHSE and internal control management system. Baili Technology has one wholly-owned subsidiary (Wuhan Refining and Chemical Engineering Design Co., Ltd.) and three branch companies (Shanghai Branch, Chengdu Branch, and Yueyang Branch). The predecessor of Baili Technology dates back to the Design Team of Project 2348 under the General Logistics Department of the Chinese People’s Liberation Army, which was established in 1970. It went through various development stages, including the Design Institute of Yueyang Chemical Plant and the Baling Petrochemical Design Institute, before acquiring Wuhan Refining and Chemical Engineering Design Co., Ltd. in 2011. Wuhan Refining and Chemical Engineering Design Co., Ltd. was established in 1979, originally as Wuhan Petrochemical Design Institute. For over 40 years, the company has been dedicated to technological innovation and specialized development in oil refining, petrochemicals, and modern coal chemical industries. It has undertaken more than 3,500 projects in engineering consultation, engineering design, and turnkey project management, accumulating extensive experience in these fields. In particular, it holds unique technical advantages in areas such as oil product processing, synthetic fibers, synthetic rubber, synthetic resins, material-based coal chemicals, and oil and gas storage and transportation, enabling it to provide customers with one-stop engineering services across the entire industrial chain.

The starting materials for producing CPL are mainly benzene/cyclohexane (cyclohexane is produced by the hydrogenation of benzene), followed by phenol and toluene. The proportions of the three raw materials in terms of production capacity are 78.60%, 19.90%, and 1.50% respectively. Since the 1980s, among the newly built CPL plants, only the one in Shijiazhuang, China, uses toluene as a raw material; all the others use benzene/cyclohexane as raw materials, without phenol. Currently, about 95% of CPL in the world is produced through the “homoxime” process route derived from Raschig. Their common feature is that they all go through two intermediate products: ** and oxime; ** reacts with hydroxylamine to form the oxime ； **Under the action of fuming sulfuric acid, the oxime undergoes a Beckmann rearrangement reaction to produce CPL. **It mainly comes from benzene and phenol. Besides the mainstream \"homoxime\" process, there are also the photonitrosation process developed by Japan’s Toray Company and the toluene process developed by Italy’s SNIA Company, but their application scope is very limited. Currently, the main CPL production technologies are as follows. (1) Traditional Rasifa: Its key process involves an oxime formation reaction with hydroxylamine sulfate to produce oximes, which then undergo a Beckmann rearrangement reaction in the presence of fuming sulfuric acid to yield CPL. Hydroxylamine sulfate is produced by neutralizing hydrocyanic acid with sulfuric acid to form a deesterified sulfate, which is then subjected to a hydrolysis reaction. This process uses sulfuric acid in three steps: hydroxylamine synthesis, oximation reaction, and rearrangement reaction. After neutralization with ammonia, a large amount of the by-product sulfuric an is produced, which has low economic value. Improvements to the traditional Raschig process focus mainly on reducing the by-product formation of sulfuric acid an. (2) Allied isopropylbenzene/phenol process: The main feature of this process is that phenol produced by the isopropylbenzene method is used as the raw material. Phenol is hydrogenated to form **;** this compound, together with hydroxylamine sulfate, undergoes an oxime reaction to produce **oxime**. The oxime then undergoes a Beckmann rearrangement in the presence of fuming sulfuric acid to yield CPL. Hydroxylamine sulfate is produced through a multi-step process using sulfur, ammonia, carbon dioxide, and water, and the by-product of anhydrous sulfate remains high. (3) BASF nitric oxide reduction process: In this process, hydroxylamine sulfate is used to control the oxidation of ammonia to form nitric oxide, which is then reduced using hydrogen in sulfuric acid; the by-product amount of sulfuric anhydride is much lower compared to the traditional Raschig process. (4) CAPROPOL process: This process has certain advantages in the oxidation of cyclohexane to **; it uses a palladium catalyst, which reduces the consumption of sodium hydroxide and the generation of waste alkaline solutions. **It reacts with hydroxylamine sulfate via an oxime formation reaction to produce **oximes**, which then undergo a Beckmann rearrangement reaction in the presence of fuming sulfuric acid to yield CPL. Hydroxylamine sulfate is produced using a nitric oxide reduction process. (5) DSM-HPO process: In this process, both the hydroxylamine synthesis and the oximation steps are carried out in a recycled phosphate buffer, without the generation of sulfuric acid. First, the nitrogen dioxide gas produced by ammonia oxidation is absorbed using phosphate buffer to produce nitric acid ； Then, nitrate ions in the phosphate buffer are reduced with hydrogen gas to produce hydroxylamine ； The hydroxylamine-rich phosphate buffer is then brought into **counter-current contact**, and oximes are formed through an oximation reaction. The advantage of this process is that sulfuric acid is used only during the **oxime rearrangement step, thereby reducing the by-product formation of sulfuric acid anhydride**. This process features complex equipment, numerous separation and purification steps, high difficulties in process control, and relatively expensive catalysts. (6) Toray Kōya nitrosation process: Under the irradiation of a mercury lamp, cyclohexane reacts with nitrosyl chloride and hydrogen chloride to form hydroxymochloride, which then undergoes rearrangement to produce CPL. Although some believe this process results in the lowest cost for producing CPL, to date only Toray Industries in Japan has adopted it to build two production facilities with a total capacity of 190 kt/a, and there have been no reports of capacity expansion over the years. (7) SNIA toluene process: In this process, toluene is oxidized to produce benzoic acid; benzoic acid is then hydrogenated to yield cyclohexanecarboxylic acid, which is subsequently neutralized, decarboxylated, and rearranged to form CPL. This process generates a high amount of sulfuric acid as a by-product, and it has poor atom economy, which presents significant limitations; the plants using this process in Italy have been shut down. Only one plant, designed to produce 50 kt/year, operated by Shijiazhuang Chemical Fiber Co., Ltd. in China, is still in use. 2 Progress and prospects of new CPL production technologies. Reducing production costs, adopting green processes, and minimizing environmental pollution have always been key aspects in the development of new CPL production technologies. The newly reported CPL technologies can be summarized as the butadiene process route and the “homoxime” process route. 2.1 Research on the butadiene process route: Over the past decade or so, several large international companies have actively researched process routes that use non-aromatic compounds as raw materials. DSM and DuPont have collaborated to develop a process for producing CPL using butadiene and carbon monoxide as raw materials, and BASF has also applied for similar patents. The butadiene/methane process developed in collaboration between BASF and DuPont has an industrial pilot plant with a capacity of 1 kt/a built in Germany. When the process for producing CPL using the butadiene route was first introduced, it was claimed that the production cost of CPL could be reduced by $300 per ton, which caused a significant stir in the industry at the time. In 1995, BASF and DuPont planned to build a large-scale facility in Hainan Province of China using a butadiene/methane process to produce 150 kt/a of CPL and 150 kt/a of hexamethylenediamine, but this plan has been postponed time and again and has not yet been implemented. DSM has also stated on multiple occasions its intention to expand production capacity in Nanjing using the butadiene route, but no action has been taken yet. 2.2 Research on the “homoxime” process route: The “homoxime” process, which was developed based on the Raschig process technology, has remained relatively stable over the past three decades, but significant breakthroughs have recently been achieved. **The ammonia oximation process, **oxime gas-phase rearrangement process, and cyclohexane bio-catalytic oxidation process have entered the industrial testing stage. 2.2.1 The production of the cyclohexane bio-catalytic oxidation process ** involves oxidizing cyclohexane with air to produce cyclohexanol and **, which are then separated, followed by dehydrogenation of cyclohexanol and purification processes to obtain the final product. **Currently, the cyclohexane liquid-phase air catalytic-free oxidation process is widely used in such devices. Its drawbacks include a low one-pass conversion rate of cyclohexane and poor selectivity for alcohols, which results in high material and energy consumption as well as the generation of large amounts of waste alkaline solution. The bionic catalytic oxidation process retains the advantage of using air directly as an oxygen source in current cyclohexane oxidation industrial processes. It reduces the reaction temperature and pressure, increases the one-pass conversion rate and overall yield, reduces energy consumption and waste liquid discharge. The oxidation by-products consist mainly of adipic acid instead of various complex components, and the recovery and utilization of adipic acid can improve economic efficiency. Therefore, the biocatalytic oxidation of cyclohexane to ** using this technique offers significant advantages in terms of material consumption, energy use, and environmental impact. In 2003, Sinopec Corporation conducted industrial trials of the cyclohexane bio-catalytic oxidation process at its Baling branch plant. Upon evaluation, it was determined that the industrial trials were carried out safely and reliably, that the economic and technical indicators were excellent, and that the technology was innovative. A \"Process Package for the Production of 124,000 tons per year of ** via Cyclohexane Bio-catalytic Oxidation\" was developed, and this technology is set to be implemented in industrial production facilities in the near future. 2.2.2** Ammonoximation process: This process involves placing **, ammonia, and hydrogen peroxide in the same reactor to synthesize ** oxime in a single step. Compared with other processes, it has the advantages of a short process flow, environmental friendliness, mild reaction conditions, and low equipment investment. This process has been of interest since the 1960s, but it was only recently that it became economically viable for industrial application, thanks to improvements in titanium-silica molecular sieve catalysts and hydrogen peroxide production technologies. Sinopec Corporation and the Italian company Enichem have been actively conducting research on this process in recent years; each holds relevant patents and technologies, and both have completed pilot tests. In 2003, this process was applied to a 60kt/a plant belonging to Sumitomo Corporation in Japan and a 70kt/a plant at Sinopec’s Baling Branch. 2.2.3** Oxime gas-phase rearrangement process: Under the action of a solid acid catalyst, **oximes are rearranged into CPL in the gas phase. Since sulfuric acid and ammonia are not used, no by-product of sulfuric an is generated, which allows for a significant reduction in production costs. Many foreign companies have conducted research on this process, and Sinopec is actively carrying out such research, with a focus on improving the conversion rate, selectivity, and lifespan of the catalysts. Sumitomo Chemical Company in Japan uses a fluidized-bed reactor; **oxime/methanol/nitrogen pass through a molecular sieve at high temperature, resulting in a conversion rate of 99.3% and a CPL yield of 95.3%. 2.2.4 Hexahydrobenzoic acid-**oxime co-production CPL combined process: The “Hexahydrobenzoic acid-**oxime co-production CPL combined process” makes use of the original SINA toluene-based CPL process, employing SO3-catalyzed **oxime rearrangement in the original amidation reaction mixture. With an additional load of 150%, the **oxime conversion rate reaches 99.78%, the CPL selectivity reaches 98.90%, and the loss rate of hexahydrobenzoic acid is only 0.8%. The product quality and technical parameters meet or exceed those of the original SINA toluene-based CPL process. 3. Prospects for the application of new technologies: Based on recent research and development efforts, the key breakthrough in the advancement of CPL production technology lies in the use of new catalysts and insights from reaction kinetics to significantly simplify the manufacturing process. This leads to reduced investment in equipment, lower energy and material consumption, increased production capacity, and decreased production costs. 3.1 Combined use of Enichem’s new “ammonoximation” process and Sumitomo Chemical’s gas-phase rearrangement process: Sumitomo Chemical integrated Enichem’s new hydrogen peroxide “ammonoximation” process with its own fluidized-bed-zirconia Beckmann rearrangement technology to build a 60 kt/a CPL production facility in Aioi, Japan. The new facility came online in April 2003 and is now operating at 100% capacity, with peak rates reaching 120%. **The conversion rate to **oximes is over 99.5%, and the unconverted portion is recovered for reuse. It is reported that the quality of caprolactam produced by the new unit is significantly better than that of the old unit ； The PM value of the new device product is 45,000s, with an absorbance of over 97% ； The PM value of the old device product is 30,000s, with an absorbance of 93%. Sumitomo Chemical believes that gas-phase rearrangement and recrystallization are very important for improving product quality; if the new ammonoximation process is combined with the existing rearrangement techniques, the quality of caprolactam will decline. Sumitomo Chemical is considering expanding the production capacity of the new facility, and it is also interested in building a plant in China. 3.2 Application of the hexahydrobenzoic acid-**oxime co-production with CPL combined process: The main advantage of the \"hexahydrobenzoic acid-**oxime co-production with caprolactam combined process\" is its ability to significantly increase the yield of the target product, caprolactam, without an increase in the yield of the by-product, sulfuric acid an; this thus enables a substantial improvement in economic efficiency. This combined process technology is advanced and its flow is rational, reaching international advanced levels. The successful development of this combined process provided technical support for increasing the caprolactam production capacity of Sinopec Shijiazhuang Chemical Fiber Co., Ltd. from 65 kt/a to 160 kt/a. 3.3 Application of the new CPL technology package by Sinopec Corporation. Sinopec Corporation organized various entities from the industry, academia, and research fields to develop this new CPL process package. The individual technologies involved in the new cyclohexane oxidation process, the ammonia oximation process, the oxime gas-phase rearrangement process, and the new CPL purification process are all mature and reliable; they meet the requirements for industrial application and have been integrated together, with independent intellectual property rights. Breakthrough progress has been made in the research and development of the two core technologies of Sinopec CPL: **ammonoximation for the production of oximes** and **bion mimetic catalytic oxidation of cyclohexane**. **The ammonia oximation-based production **technology has been put into industrial use at a capacity of 70 kt/a. The catalytic oxidative synthesis of **using cyclohexane has also undergone industrial trials at the facilities of Baling Co., Ltd., and the results of these applications and tests are very promising, with excellent technical and economic performance. Currently, Sinopec’s complete CPL new process is being used in the 140kt/a CPL expansion project at the Baling branch. The project initially involves constructing an industrial test unit for a **new 70kt/a ammonia oximation process, to replace the existing HPO-based oximation setup**, with the oxime rearrangement being replaced by a three-stage rearrangement. Then, proprietary technology was used to expand the benzene hydrogenation production unit to complement the 140kt/a CPL facility ； Transforming existing units using the new biocatalytic oxidation technology with cyclohexane ； By adopting new refining technologies such as amorphous alloy catalysts and magnetically stabilized bed hydrorefining processes, the plant’s capacity was increased to 140 kt/a, and the industrialization of the complete CPL technology suite was achieved. With the successful commissioning of the ammonia oximation unit and after a brief calibration period, it is able to reach its designed capacity of 70 kt/a; its consumption and quality parameters meet the design requirements. It is expected that, following some time of adjustment and optimization, it will be able to meet all the specified standards fully. By then, the production cost of CPL will be significantly reduced, thereby enhancing CPL’s core competitiveness.

I just received news from Hengyi today; it hasn’t been put into effect yet. Does the original poster have any other specific information regarding the current progress of Hengyi Dongying’s project? People from Dongying are paying attention to the projects in their hometown.

Hengyi’s focus right now is probably still on its overseas projects